Sciencemadness Discussion Board

Nicotine Extraction and purification

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Cheapskate - 16-2-2005 at 12:29

This has been discussed and dropped for lack of information many times over the years so I've been reopening the discussion on various forums with the hope of actually managing to do it. I want to extract nicotine from tobacco and purify it.

Now, before the more annoying......er uh, helpful of you start telling me how it's easier to just smoke the darn cigarettes, how toxic it is, how it can be absorbed through the skin, how it can cause cancer, etc. I've already experimented with the material and I know exactly how to handle it. One can expound about how it's the most poisonous substance known (untrue), it has no treatment for overdose (untrue), or how the LD50 in rats is 50mg (true), but that isn't helpful. And, no I'm not a terrorist or murderer that wants the stuff to kill people with. That's mostly a bunch of TV supported hype anyway.

I've tried acid base extractions with naptha/water, choloroform/water, toluene/water all have resulted in something, but not much, and very unpure. I tried steam extraction, but this results in a bunch of water and very little alkaloid.

Does anyone know or have a way to get the solubility of nicotine in various solvents? Or maybe one of the easy derivitives like nicotine sulfate, hydrochloride, citrate? No need suggesting a web search, I've done that ad nauseum. The libraries I have easy access to have practically nothing to offer.

No, removing it from the patches is not a good option. The goo they mix it into is hard to deal with. Especially with the small quantities involved. The inhalers are easy, but too darn little for too much money. I don't have access to the nasal devices. The lozenges have similar problems in that the additives to slow the intake are impossible to remove; they're also expensive.

I have discovered a number of things. Don't start off with water, the tobacco swells up and absorbs the water leaving you with tobacco jelly that is tough to deal with.

Nicotine disolves in everything, additionally, it seems to dissolve anything as well.

Being water soluble it is tough to get out of water, but forming a hcl or sulfate salt will move it to a non polar.

Every extraction seems to loose a bunch of it. Even with extremely heavy salting.

Most of the patents don't work as advertised, they lead to mostly blind alleys.

The schoolbook extractions don't work well, there are so many washes and extractions that you run out of nicotine before you finish. The mechanical losses are too big.

Kerosene (yuck) is a really efficient extraction solvent.

Suggestions? Solubility data?

I already have the Merck entry (not very helpful) and have reviewed about 700 patents.

In answer to a question that I’m sure will come up since it has in every single thread I've found about it. About three years ago I tried to quit smoking (for the 17th time) and used the patches and inhalers. The patches gave me trouble and the inhalors were too darn expensive for a tiny hit. Did you know they allow one to use up to 40 of these things a day. So I reverse engineered the inhalers and created my own that I can refill all I want for 1/1000th of the cost. I've also created nasal sprays, lollipops, lozenges, etc. none of them FDA approved.

Now before someone starts advising me about the risks of nicotine, keep in mind that for three years I've controlled the dosage myself and handled this substance without mishap. The reality is that it's not nearly as toxic as one would be led to believe based on the hype out there. My methodology is more sophisticated and safe than buying X from a guy on the corner or in a booth at a bar.

Now, I want to extract it myself rather than order it from chemical suppliers since the patriot act may flag me as a suspicious person. Additionally, a lecture on why don't I just wean off the substance will fall on deaf ears since I've been trying that for three years as well. We don't all have the same makeup and it seems to be harder for me. But I don't smoke anymore and no one cares if I suck on a lollipop or have a lozenge in my mouth. Snuff and chewing tobacco are not options, they’re as dangerous and offensive as smoking.

neutrino - 16-2-2005 at 14:05

Remember that it’s also used as a pesticide. You might be able to get it from that. There is a thread at RS about this here, if it helps.

Cheapskate - 16-2-2005 at 14:52

Thank you for the pointer. I went and looked at that thread and it is typical of all the threads I've looked over the years.

Someone asks how is it possible and then they spend days explaining why they want to do it. While people rail at them about how dangerous it is and how they shouldn't do it.

I've been lurking on this board for a few weeks and I've found this board really good and the folks here not as prone to attack as many other places.

However, the thread on RS did point out a problem with my posting. (actually 2 but I'll get to the second one later). I didn't tell you what I've already found out.

Like I said most of the patents just don't work; at least in smaller quantities. For example to create Nicotine Sulfate the industrial process is to percolate a non-polar through tobacco and then pump it into the bottom of a container of dilute sulfuric acid. As the non polar rises (note the density requirement here) it releases some of the nicotine to the acid to produce nicotine sulfate in the water. The non polar is pumped back into the percolator.

This process proceeds until the dilute sulfuric is neutralized, and behold, you have nicotine sulfate in water. This used to be known as Black Leaf 40. 40% because at concentrations over that it would precipitate out.

However, doing this at home is tough. Maybe a fuel pump and a coffee pot or something could be employed, but it has evaded my skills so far. I have succeeded in making some interesting messes though.

Another method is to extract the tobacco with MEK then extract with acidic brine If you basify the brine and heat it, a separation happens that is purported to be a separate phase of nicotine. Well, they lied and didn't consider the solubility of MEK in water. What you get is MEK and junk floating on top that is mostly sugars, fats and such. I wasted more than a month on that method.

An extraction of tobacco with kerosene followed by an extraction with acidic water rinsed with naptha, ether, naptha. Basify, salt and extract with naptha on evaporation will give you pretty pure nicotine, but the washes worry me about losses. Also, I can't seem to get rid of all the naptha. There always seems to be a bit of it in there.

How the heck do you evaporate the solvents from a tiny quantity of liquid product.

Final purification? Don't get enough of this stuff to distill. Even so, I'm worried about degradation due to heat. I could possibly steam distill it, but how the heck do I get it out of the water?

Now, to the mistake I made above. If you acidify it it will force most of it into the water, not the non-polar! I can't believe I messed that up.

Cheapskate - 16-2-2005 at 15:00

Oh, thanks for the pointer to insecticide. However that form of insecticide has been discontinued in the US for several years. There's tiny amounts in a few products, but not enough to try to use. There (apparently) is only one product left that has nicotine sulfate in it and that is only commercially available for hothouse fumigation.

I tried to get it through chemical suppliers. What a joke, they all thought they should report me to homeland security except for one that was willing to sell it to me for U$5 a gram in 100g quantities. Quite a mark up from the U$86 dollars that acros sells it for. That supplier would probably have called homeland security as soon as the check cleared.

Eclectic - 16-2-2005 at 15:20

You could try a butane extraction like I've seen on the Internet for cannabis...

Cheapskate - 16-2-2005 at 16:00

Regarding butane. I did this one with a piece of pvc pipe and about 100g of tobacco. The extraction worked exactly as described for THC, but it produced a grease that wasn't active. I think I took out oils and such and left the nicotine behind. Tried this twice and got the same results.

There is a possibility that I haven't tried. Nicotine is held in the tobacco leaves as various salts as well as the freebase. If one were to dampen the tobacco, add lye and mush it all together it could be that this process would release more of the freebase to be liberated by the butane.

The commercial process for this uses CO2, but I don't understand how to do that at home.

I did find a french procedure that used picric acid to form a picrate with nicotine that (apparently) precipitates from water. I haven't tried it since I would then have to find a way of disposing of the picric acid.

If I could find a salt of nicotine and a solvent it was insoluble in.......

Geomancer - 16-2-2005 at 16:51

I see you've already checked usenet, so I won't regurgitate what I read there. The zinc chloride double salt thing sounded interesting, though. Your best bet would be to rig equipment to do the industrial procedure. What's so hard about a pump, anyway?

Polverone - 16-2-2005 at 17:42

From <A HREF="http://bcis.pacificu.edu/~polverone/alkaloids-jbig2.pdf">The Plant Alkaloids</A>:
Quote:
Nicotine, C10H14N2. The pure alkaloid is a colourless oil, b.p. 246.1 °/
730-5 mm. It can be purified
through the crystalline zincichloride, B,ZnCl2,2HCl,H20, the regenerated
base being distilled under reduced pressure (20-40 mm.) in presence of
nitrogen or hydrogen. It distils unchanged in a current of steam and is
readily soluble in alcohol, ether or light petroleum. The behaviour of
nicotine with water has been studied by several workers.19 It is miscible
in all proportions with water below 60° and above 210°; at intervening
temperatures soluble hydrates are not formed and miscibility is limited.
According to Kelly et al.19 an azeotrope is formed, which contains 2.45 per
cent, of nicotine and boils at 99-6°/760 mm. The salts are readily soluble
in water, do not crystallise easily and are dextrorotatory.

...

The acid d-tartrate,
B . 2H2C4H4O8 . 2H2O, m.p. 88-9° (hydrated), and
the neutral d-tartrate, m.p. 68-5° (hydrated), , both
crystallise from alcohol on addition of ether. The dipicrate,
B . 2C6H2(NO2)3OH, short yellow prisms, m.p. 224°, and the tetrachloriodide,
22 C10H14N2.2(HICl4), orange prisms, m.p. 150° (dec.), are
characteristic.


That's probably nothing new to you, but it does confirm that there are limited options for purifying nicotine. Try forming the dipicrate. Picric acid can easily enough be disposed of by conversion to its ammonium salt and burning. There is little in risk in disposing of limited amounts of picric acid this way.

Eclectic - 16-2-2005 at 19:13

Isopropylamine should be a good alkaline extraction solvent for free alkaloids. I believe the boiling point is in the same range as that of ether. Diisopropylamine boils in the 70's if you want something that evaporates more slowly.
Either one should be fairly simple to make from acetone, an ammonium salt, and a dissolving metal such as amalgamated aluminum, zinc dust, nickle salt treated aluminum or zinc, magnesium turnings, ect.

Gattermann-Wieland, will scan...eventually

S.C. Wack - 16-2-2005 at 20:32

Commercial tobacco extract (300 c.c, d. 1.8), which can also be prepared by concentration of the faintly acidified dilute extract to be had in any cigar factory, is made strongly alkaline with concentrated sodium hydroxide solution. Steam is passed through the hot solution and the free nicotine bases pass over. About 1.5 L of distillate are collected, made faintly acid to Congo red with solid oxalic acid (a weighed quantity), and concentrated to a syrup. When the syrup cools nicotine oxalate contaminated with some ammonium oxalate separates. The crystalline sludge is transferred to a separating funnel into which is poured rather more potassium hydroxide solution (1:1) than corresponds to the oxalic acid used. Heat is developed, and after some time the crude nicotine rises to the surface as a brown oil, which is separated from the cooled mixture by repeated extraction with ether. The concentrated ethereal solution is dried with a few pieces of solid potassium hydroxide and then the ether is evaporated. The residue is fractionally distilled in a vacuum from a small Claisen flask. Since rubber stoppers are attacked by nicotine air-tight corks are used instead.

By repeated distillation of the higher boiling fraction the pure base is obtained as a colourless liquid of boiling point 114°/10 mm., 120°/14 mm. At atmospheric pressure nicotine boils without decomposition at 240°. The yield varies from 4 to 6 g.

The specimen turns brown very soon if exposed to the air, and must be kept in a sealed glass tube.

Cheapskate - 17-2-2005 at 00:04

I'm in a densly populate area and a little reluctant to deal with picric acid (no experience with that substance). The oxalic acid idea doesn't sound bad at all, that may be my next try, but I'll have to figure out how to get it into alcohol.

Alcohol is as bad as water in the extraction, the tobacco swells up and clogs everything.

The problem with a pumped percolator is that it clogs up. I haven't found a way to screen the tobacco without stopping fluid flow. This stuff just falls apart when made basic to release the salts of nicotine into a freebase and clogs up everything.

I also tried vaporization. Heating the tobacco to 200C with a cold finger. This condensed some acrid water, but not much else.

Oh, I've tried several different sources of tobacco, Marlboros, cigars, pipe tobacco, and even the dust used in organic gardening. It seems that the cheaper it is, the easier it is to extract.

Any clues on how to isolate the .hcl salts or sulfates?

Cheapskate - 17-2-2005 at 14:38

Just to let you know that I take your suggestions and ideas seriously, I looked really closely at the Gattermann-Wieland isolation above.

I thought this was a great possibility until I finally discovered that the "commercial tobacco extract" was actually referring to the nicotine sulfate insecticide that used to be sold all over the world. This is 40% nicotine sulfate and it would be easy to get product out of something that concentrated. The idea of boiling tobacco down to a slurry was one of the first things I tried, but nicotine would escape with the vapors.

However, the oxalic acid is still a real possibility.

BromicAcid - 17-2-2005 at 17:05

Assorted Nasties by Harber has a step by step cookbook method for extracting nicotine, the basic outline is to thoughly dry your starting material, powder it, a lenthy process of heating with lime and water and letting sit for periods, filtering, boiling, filtering, boiling, and finally distillation, followed by a liquid/liquid extration of the resulting azeotrope and evaporation of the ether used for the extration to yield "a very good grade of nicotine."

[Edited on 2/18/2005 by BromicAcid]

Cheapskate - 18-2-2005 at 13:39

Thanks BromicAcid. I've looked at about 7 of the water methods an they all have the same problem absorption into the tobacco. Let's say you take 100 grams of tobacco and add 300ml of water to it with some NaOH. You will get swollen tobacco that won't release the water. It can't be filtered or screened. You can wrap it up in a rag and squeeze which will give you back around a hundred ml of dark solution that still won't filter.

If you try to extract this it will form an emulsion that just won't separate. I've left these setting for days with no luck.

Using a brine to soak helps some, but there is little solubility in brine (that's, after all, the point) and I don't believe the extraction actually works.

I've had the best luck with a non polar solvent for the first extraction. Much less swelling an it can be filtered....sort of.

Eclectic - 18-2-2005 at 14:14

How about just steam distilling from tobacco in alkaline water?
You might want to have a really tight distillation setup and good ventilation.
:o

S.C. Wack - 18-2-2005 at 14:22

Why not just use a lot of acidic water and then boil it down?

Cheapskate - 18-2-2005 at 16:12

I took 50 grams of tobacco and steam distilled 1.5 liters of water through it. I then acidified and reduced the volume to around 100ml and extracted. Nothing active came out.

I then took the same tobacco (I figured something had to be in there) and based it to ph14 in 100ml of water. Yes, it turned into goo and distilled another 1.5 liters of water through it. Distilled that down to around 150ml and extracted. Got some actives, but it was bound in a large amount of black goo. I acidified the goo with hcl and washed with ether then based and extracted. I got maybe a drop of dark brown oil that was just barely active.

I have not tried the idea of using a LOT of water for extraction. The idea I'm going to try is to extract 100g of tobacco with about a gallon of basic water ph>14. This will give a messy black liquid. This I'll screen a couple of times and then press in a coffee can with holes to get as much of it as possible.

Then acidify it to ph < 3 and distill it all through a column to keep the solids and whatever else remains. I'll then wash the residue with ether before a normal acid base extraction. Save the ether though in case nothing comes out.

this will be a pain since distilling that much water takes time in a small setup, but it should prove that I can get something out.

Any suggestions would be welcome, I'm going to start this tomorrow.

Sandmeyer - 18-2-2005 at 16:51

Quote:
Originally posted by Cheapskate
I took 50 grams of tobacco and steam distilled 1.5 liters of water through it. I then acidified and reduced the volume to around 100ml and extracted. Nothing active came out.


If you add acid you proptonate it, the result is soluble in water and insoluble in non-polar solvents. What phase did you save? If you saved non-polar phase there is wonder that you got nothing.

Authors seem to have limited lab-experience, but the method nontheless could give you some idea of how this A/B extraction could be done (what layers to save and so on):

http://mapage.cybercable.fr/awebster/nicotine/method.htm

[Edited on 19-2-2005 by Sandmeyer]

Eclectic - 18-2-2005 at 19:49

Na2CO3, or even NaHCO3, should be good enough as a base. for the initial hydrodistillation.
If you start with the pH too high, you are going to get all kinds of degradations, condensations, hydrolysis reactions.
Use fractionating column, slowly distill H2O/nicotine azeotrope, make alkaline, extract,THEN concentrate.

[Edited on 19-2-2005 by Eclectic]

Cheapskate - 18-2-2005 at 23:56

Sandmeyer, Thanks for the pointer to the workup. I found that about a month back and read it in great detail. Notice that the kids didn't get anything substantial. I loved the part about having to keep going back for more solvents.

Let me assure you, I've had the same problem. When one is extracting directly from the natural products there is a TON of stuff that you have to deal with. The fats turn into soap and allow normally non-polar materials into the non polar solvents. So you can wash essentially forever and just keep getting trash out.

It may be that Eclectic is right, that I'm destroying the nicotine with a solution that is too basic, but I can't tell. There may well be an azeotrope of nicotine and water, but I can't tell that either. If you distill water and tobacco, how the heck do you tell if you've run enough water through the system. Like I said, I put 1500ml through a hundred grams and it was still coming over yellow. ...and I didn't get anything.

There were some lorillard papers that indicated that steam distillation under high pressure was the common way of commercial water extraction. That would explain my lack of success. However, my personal experience has been that nicotine is very soluble in water so a straight water extraction seems to be the best first step if I can somehow get the darn water back, it just wants to stay in the tobacco.

JohnWW - 19-2-2005 at 01:12

Re possible uses of nicotine, which consists of a N-methyl-tetrahydropyrrole ring attached at its 2-position to the 3-position of a pyridine molecule:
as well as an insecticide, it can be also oxidized with concentrated HNO3 (and some other oxidants) to obtain nicotinic acid, or pyridine-3-carboxylic acid, which is vitamin B1 (which is incorporated into the coenzyme nicotinamide adenine dinucleotide.).

Because of the polarity of the molecule, the best solvents for a nicotine solvent extraction should be non-acid polar organic compounds, especially aromatic ones like pyridine.

sparkgap - 19-2-2005 at 03:02

John, yes, nicotine can be oxidized to niacin and is incorporated into NAD, but niacin is NOT, I repeat, NOT Vitamin B1. That's thiamine. Just wanted to point that out.

Cheapskate, have you tried extracting with ligroin?

sparky (^_^)

Eclectic - 19-2-2005 at 16:02

For your own personal use in very small quantities, have you considered using an expresso machine for the initial extraction?
You might have to do a run once a week or once a month, but nicotine oxidizes very easily anyway. You could acidify the initial extraction water with citric, abscorbic, or acetic acid to avoid machine damage.

Sandmeyer - 19-2-2005 at 16:30

Quote:
Originally posted by Cheapskate
It may be that Eclectic is right, that I'm destroying the nicotine with a solution that is too basic, but I can't tell.


I can see nothing in the structure of nicotine suggesting it can be "destroyed" by a base (nucleophile).. The only site where a hypothetical nucleophilic attack might take place in nicotine is the C=N fragment of the pyridine ring. Not only is this site not sufficiently electrophilic, but if the attack was to happen it would destroy the aromacity of the pyridine ring - a highly unfavorable situation. In other words this would not happen, not even a organo-metallic reagent would add like that , let alone the OH...


Quote:
Originally posted by Eclectic If you start with the pH too high, you are going to get all kinds of degradations, condensations, hydrolysis reactions.


Really? Cool...

[Edited on 20-2-2005 by Sandmeyer]

Eclectic - 19-2-2005 at 17:43

Side reactions due to everything other than nicotine that is in the tobacco.



You don't think the pyrrolidene ring is subject to attack? I'm thinking that some of those carbons could give up H+ .

[Edited on 20-2-2005 by Eclectic]

[Edited on 20-2-2005 by Eclectic]

Cheapskate - 20-2-2005 at 00:09

Holy Cow, using an expresso machine never occurred to me. Right now I have the large volume of water extraction running, but the old expresso machine will come out for the next try.

Talk about high pressure steam extraction! Thank you very much, I'll report back on both of the current ideas.

Sandmeyer - 20-2-2005 at 03:41

Quote:
Originally posted by Eclectic
Side reactions due to everything other than nicotine that is in the tobacco.



You don't think the pyrrolidene ring is subject to attack? I'm thinking that some of those carbons could give up H+ .


N-methyl-pyrrolidine has no acidic hydrogens. If there was a hydrogen instead of the methyl group on the nitrogen, then it would have been another story, but it would still take BuLi or simillar to deprotonate it.

Eclectic - 20-2-2005 at 10:05

Pull hydrogen from the attachment point to the pyridine ring: nitrogen ylide/imine, resonance stabilized with pyridine ring.
I think that pyrrolidene ring is going to fall right apart if you look at it crosseyed under strongly alkaline conditions.
http://clem.mscd.edu/~wiederm/401chp/unit3chp/ylideschp/page...
We already know that nicotine is very easily oxidized under pH neutral conditions.

[Edited on 20-2-2005 by Eclectic]

[Edited on 20-2-2005 by Eclectic]

Sandmeyer - 20-2-2005 at 10:56

Quote:
Originally posted by Eclectic
Pull hydrogen from the attachment point to the pyridine ring: nitrogen ylide/imine, resonance stabilized with pyridine ring.


Huh?


Quote:
I think that pyrrolidene ring is going to fall right apart if you look at it crosseyed under strongly alkaline conditions.
http://clem.mscd.edu/~wiederm/401chp/unit3chp/ylideschp/page...
We already know that nicotine is very easily oxidized under pH neutral conditions.

[Edited on 20-2-2005 by Eclectic]

[Edited on 20-2-2005 by Eclectic]


In the link that you provided there is a positive charge on the nitrogen, this is the reason why the base react as it does, since the resulting negative charge can be stabilized (lone pair forms on the nitrogen). Do you see a +1 charge on any nitrogen in nicotine?

Eclectic - 20-2-2005 at 12:01

The imine should form with no problem.
You aren't going to be happy without experimental verification, are you?
Reflux some nicotine with NaOH, assorted carbohydrates and other biologicals while exposing to air and see how much of the nicotine you can recover.:)

I might be wrong, it's been many decades since my chem courses, ...but I don't think so.

[Edited on 20-2-2005 by Eclectic]

Sandmeyer - 20-2-2005 at 12:35

Quote:
Originally posted by Eclectic
The imine should form with no problem.


No, the imine will not form.


Quote:
You aren't going to be happy without experimental verification, are you?


Anything that makes sence would have been fun. I just find it hard to belive that a hydrogen attached to a carbon (pKa around 50) can be stripped off using OH (pKb ~16)... The whole discussion is getting really boring and repetative...


Quote:
Reflux some nicotine with NaOH, assorted carbohydrates and other biologicals while exposing to air and see how much of the nicotine you can recover.:)


I'm not intersted in nicotine, so I won't do that...

Quote:
I might be wrong, it's been many decades since my chem courses, ...but I don't think so.


Okidoki..

Eclectic - 20-2-2005 at 13:00

"I just find it hard to belive that a hydrogen attached to a carbon (pKa around 50) can be stripped off using OH (pKb ~16)..."

And yet that is exactly what happens in aldol and claisen condensations.

So is the number 2 carbon in the pyrrolidene ring more or less acidic than average? I was thinking more acidic, but I might have it backwards.
Methyl iodide methylates nicotine on the pyridine nitrogen if that gives any clue.

http://www.medicine.uiowa.edu/frrb/education/FreeRadicalSp01...
(page 5)




[Edited on 20-2-2005 by Eclectic]

Sandmeyer - 20-2-2005 at 18:14

Quote:
Originally posted by Eclectic
And yet that is exactly what happens in aldol and claisen condensations.


In such reactions this is possible since you have a carbonyl group alpha to the carbon atom bearing the acidic hydrogens (that's the reason they're acidic). When you deprotonate the alpha carbon, the negative charge can be stabilized, ending up on the oxygen and you get an enol.

Quote:
So is the number 2 carbon in the pyrrolidene ring more or less acidic than average?


Since you have an electon donationg group (an amine with a lone pair of electrons) this would lead to even further destabilization of the negative charge that might result from deprotonation of the adjecent carbon. For instance the base streangth of BuLi goes: tert-BuLi > sec-BuLi > n-BuLi.. Reason for this is that methyl groups are electron donating, this destabilize the negative charge on carbon and the tertiary base is stronger (the more electron-donating groups around the carbanion - the less stable it is). This is opposite for carbocations (acids), electron-donating groups stabilize the positive charge, hence acids and bases are eachothers opposites..

Quote:
Methyl iodide methylates nicotine on the pyridine nitrogen if that gives any clue.


Yes, and that product would be reactive toward nucleophiles as it would contain C=N-Me (+), this would make it electrophilic as Nu: (-) ---> C=N-Me (+) gives Nu-C-N-Me.. The positive charge makes a lot of difference as it is powerfully electron-withrawing, comparable to a nitro group...

But admittedly there is a reaction in Vogel's third ED where pyridine itself reacts with NaNH2 (very strong base), so it is possible but NaOH is not powerful enough...

Eclectic - 20-2-2005 at 22:05

I yield. I mistakenly thought the amine and pyridine ring were electron withdrawing, and the lone pair on the nitrogen would stabilize the imine.
:)

Cheapskate - 21-2-2005 at 23:56

OK, so it doesn't appear that I ruined it by being over zealous with the NaOH.

My experiments with a LOT of water are proceeding, but I suspect I just wasted a bunch of materials. There is a bad problem with emulsions. Looks like the alkaline nature of the raw material and the fats don't mix well. I get a soapy mess if I mix a non-polar with the water extraction.

Now, I've seen emulsions before, but this one is terrible. If you wait long enough, it solidifies. Not quite into a wafer, but currently I have a two inch emulsion in my sep funnel that resists gentle shaking.

So, not only does one have to deal with the swelling tobacco that just won't filter worth a damn, you get the emulsion from hell. No, adding more solvent doesn't help, nor does adding more water. No wonder all the schoolroom extractions start with something besides water.

I tried the idea of an expresso machine. I loaded 20grams of tobacco in it with 4 cups of water and let it go. I got about two cups out before it plugged the filter in the expresso machine. I vented the machine and pulled the coffee holder off and broke up the tobacco cake and fed another two cups of water through the cake. I now have an extremely dark 500ml of water and tobacco extract. Interesting smell, but not much different from a normal water extraction. This is just setting on a shelf waiting for me to do something with it.

However while I was setting there staring at it I had an idea. I took a few grams of tobacco and put it in a tube with maybe 10 ml of acetone. I heated this to boiling after adding a chunk of NaOH. The idea is to extract what I can out with the acetone. I expected the acetone to turn black like the water since it's polar as well, but it only took on a yellowish color.

This, when evaporated, left a yellow tar. I dissolved as much as I could of the tar into 10 ml of water. This left an insoluble resin like substance and gave me some slightly yellow water. Now I know there isn't enough nicotine in this water to actually do anything with, but I was flat amazed that the acetone didn't pick up more from the tobacco.

Could this be a clue? Dry some acetone, use more tobacco and see if I've found a way to leave most of the undesirables behind? My experience has been that nicotine is extremely solubile in acetone so I should have gotten it out of the small sample of tobacco.

I suspect I'll still acidify the bunch of water extract I have and reduce the volume to see what's in it, but what a mess that will be.

More thoughts, ideas? Keep em coming, I'm listening.

Polverone - 22-2-2005 at 01:52

Heating acetone with NaOH and nothing else save traces of water will give you colored condensation products, though I don't know what that'll yield on evaporation. I would run a comparison with acetone and a bit of NaOH, sans tobacco, to get an idea of how much gunk you're introducing this way.

Swelling and emulsions seem to be major problems, and swelling will (presumably) not be triggered by nonpolar solvents. Soxhlet extraction with a low BP nonpolar? Grinding it to dust, then heating the tar (ha ha) out of it in a highish-BP hydrocarbon like toluene or xylene? Maybe ball-milling it with dry NaOH before mixing and heating with hydrocarbons?

Or here's an odd idea: use p-dichlorobenzene (mothballs) as your hot extraction solvent. It has a highish 174 BP but sublimes readily, so can be separated from your extract more easily than xylene or toluene. I'm going to make the unsubstantiated guess that, all else being equal, higher solvent temperatures will give you better extraction of the plant matter. I imagine the real trouble would be keeping it hot while filtering, and not being choked by all those mothball fumes when working with it hot and in the open.

Hmm, make some sort of "teabag" to hold the tobacco? Tobacco and mothballs go in sealed jar, sealed jar goes in sandbath, tobacco is extracted by molten p-dichlorobenzene, jar is afterward allowed to cool to room temperature, jar is smashed and solid p-DCB mechanically separated from the teabag, p-DCB is sublimed away with moderate heat or maybe vacuum. For that matter naphthalene could probably do the same trick, depending on what sort of mothballs you find.

Or if you don't like high temperatures, what about ball-milling it with your solvent for an extended period of time?

What about dry distillation in inert gas? It's probably not something you'd like to use good glassware for. Maybe actually dissolve/dry-distill the tobacco in NaOH/KOH eutectic? I'm sure it will take apart the plant material like nobody's business, but it's a powerful oxidizing environment if you can't exclude air (even then I'm not sure).

Dry distillation variation: mix dry, clean sand, table salt, or anhydrous MgSO4 with powdered tobacco, place in a tube or jar, purge jar with inert gas, and heat. What can you (nonpolar) solvent extract from the mixture of sand and cooked tobacco afterward? With a tube, can you stick the tobacco at the bottom, dry powder over it, and heat only at the bottom so that products are trapped in the progressively-cooler solids above the heated region? Do you pour solvent over the whole mess and heat it again after the really high-temperature phase? I'm imagining ways to trap volatile products of dry distillation without actually using good glassware or custom apparatus.

Maybe get a secondhand centrifuge and use it to overcome the difficulties with aqueous solutions?

Are there any microorganisms that would attack the leaf matter yet leave the nicotine intact, so that there's nothing left to swell and clog filtering attempts?

Well, that's my grab-bag of wild ideas for the night.

Eclectic - 22-2-2005 at 03:55

Well yes, you probably didn't destroy the nicotine with NaOH, but the idea of making all kinds of crud with everthing else in the tobacco is still valid. pH9-11 is plenty basic to free up most of the nicotine.
With the expresso machine run, did you acidify the water with anything? Maybe try white vinegar as extractant. 1-2 cups will probably extract the bulk of the nicotine. Your initial water extract needs to be acidic to extract soluble nicotine salts. If you want to steam distill the free nicotine, you would make the water alkaline, 1-3% Na2CO3 would have a pH 11-11.5. I think there would be serious risk of poisoning from the vapors if you tried that with the expresso machine.
(If you boil baking soda and water you end up with a sodium carbonate solution)




[Edited on 22-2-2005 by Eclectic]

sparkgap - 22-2-2005 at 06:41

Eclectic,

QUOTE:

...I think there would be serious risk of poisoning from the vapors if you tried that with the expresso machine...

Now that would be a novel method of nicotine administration. :D

Polverone:

Use p-dichlorobenzene? Seeing that he intends to consume the nicotine thus extracted, would it really be worth it to attempt extraction with a suspect carcinogen? Now naphthalene, hmm...

Cheapskate:

Just to confirm, do you do these extractions with fresh tobacco leaves or dried tobacco leaves?

sparky (^_^)

S.C. Wack - 22-2-2005 at 10:23

If you cant filter it, then you shouldn't grind so finely, or you should change your filter to something like mesh or cloth. I had no problems in my experience making my own insecticide years ago.

I'm not so sure that adding a strong base to plant material is a good idea.

The extract you have should already be acidic, although Merck says that nicotine is soluble in water below 60C, I'd still add a little acid as suggested before.



[Edited on 22-2-2005 by S.C. Wack]

Cheapskate - 22-2-2005 at 10:45

Every attempt has been done with dried tobacco products. I'm currently working my way through a bag of tobacco dust that was designed as an insecticide. I don't have access to fresh tobacco leaves.

Even though they're dried and powdered, they have a water content. My attempts at dry distillation using a cold finger turned up a lot of water.

Mothballs are a compelling idea because they are so out-of-the-box, but I suspect they would be the same as using a low temperature solvent such as ether and just letting it evaporate off. There is the advantage of being able to heat it, but wouldn't that be the same as an ether reflux? Actually, I started to try the ether idea, but chickened out due to the flamability problem. DCM would be a possibility since it's non polar and has a low boiling point, but I have to distill that stuff out of paint remover to get it. A painful, long, tedious process that I wanted to avoid if possible. The school book extractions often start with methanol as the first extraction, but my experience with alcohol (95%) was that I had a swollen ball of tobacco and couldn't get the alcohol loose. Now that may have been the 5% water, but I suspect it worked like water and caused swelling. I haven't actually tried methanol yet since I don't know what it its solubility is with other solvents. It could be a problem separating from something else. I guess I could just evaporate it away.

I used to have a link to a solubility chart of various solvents in other solvents. It got lost somewhere. Does anyone have such a thing?

unionised - 22-2-2005 at 12:33

Well, everyone else has had a go so here's my 2c worth.
The fats are a pain in the neck if you do an alkaline extraction, they make soaps and the emusions never settle.
A couple of thoughts, 1 use calcium hydroxide and make insoluble soaps that are much less effective emulsifiers. or
2 Don't do an extraction. I read that the commercial process uses steam distillation of an alkaline extract.
Not many of the compounds present in plants will steam distil.
If you take a flask, put the tobacco in it and wet it with slightly alkaline (you don't want to get things too alkaline, god knows what other reactions you might get) water saturated with salt, then distill this you should get steam, at a higher temperature than normal because of the salt, (and, because of the salt, the soaps won't dissolve so well so it will foam less). This should carry over the nicotine (You may need to add a dropping funnel to the aparatus so you can add more water to get all the product over.)
That should give a crude distillate with the prduct in water. Acidify it (again, there's no point in overdoing it) and boil it down. That should remove a lot of the other organic trash that is not an alkaloid, but is steam volatile. Re basify it and re distill over the nicotine (and other steam-volatile alkaloids).
If all the assumptions I have made all work you should end up with crude nicotine in water. Add HCl and leave it somewhere warm for the water and excess HCl to evaporate, you should end up with nicotine hydrochloride.
It won't be very clean, but it should do the job.

JohnWW - 22-2-2005 at 12:35

Besides nicotine, tobacco also contains other alkaloids similar to nicotine, for example, isomers in which the tetrahydropyrrole ring is attached at the 2- or 4- position to the pyridine ring and/or via the 2-position on the tetrahydropyrrole, and/or the N-CH3 group is replaced by --NH or N-CH2CH3 or others, and/or there are substitutents on the pyridine or tetrahydropyrrole rings. Besides nicotine, nornicotine ("nor" meaning without the -CH3 group), anatabine and anabasine are the principal minor alkaloids present. Another is nicotyrine. They are all chiral, having optically active enantiomers, which may react differently with some reagents. Although the raw tobacco alkaloids are 98% nicotine, the minor ones would have to be somehow taken into account, or removed e.g. by chromatography, if one wanted to use raw nicotine extracted from tobacco as a reagent for syntheses.

See http://www.tobaccopedia.info/leaf_chemistry/alkaloid_biosynt... , http://www.tobaccopedia.info/leaf_chemistry/the_influence_of... , http://www.ash.org.uk/html/regulation/html/additives.html , http://www.trdrp.org/research/PageGrant.asp?grant_id=2142 , http://www.sensir.com/newsensir/AppNotes/app030.pdf , http://pages.towson.edu/jsaunder/Saunders%20Publications/15.... , http://www.shaman-australis.com/~auxin/tobacco.html , http://www.ndp.govt.nz/tobacco/cigaretteaddictiveness.PDF , http://www.ndp.govt.nz/tobacco/cigaretteaddictiveness_final%... , http://www.ash.org.nz/pdf/Smoking/Tobacco/Nicotine.pdf , http://www.foodstandards.gov.au/_srcfiles/P278_Nicotine_&... , http://www.cdc.gov/tobacco/sgr/sgr_1988/1988SGR-Chapter%202.... , http://doi.wiley.com/10.1002/(SICI)1520-636X(1999)11:1%3C82::AID-CHIR14%3E3.0.CO;2-C , http://doi.wiley.com/10.1002/(SICI)1520-636X(1996)8:4%3C295::AID-CHIR1%3E3.0.CO;2-F , http://tobaccodocuments.org/product_design/2022157406-7416.h... , http://arjournals.annualreviews.org/doi/pdf/10.1146/annurev.... , http://www.hc-sc.gc.ca/hecs-sesc/tobacco/pdf/T-301e4.PDF (Determination Of Alkaloids in Tobacco) , http://www.isc-newsletter.com/newsletter/nov04/lin/art3.pdf (Determination Of Alkaloids in Tobacco by Extraction).

Nicotine alkaloids are also found in the leaves of the coca plant, see http://www.answers.com/topic/nicotine .

They become carcinogenic through the formation of nitrosamines, e.g. N-nitrosonornicotine , http://www.smoke-free.ca/factsheets/pdf/TSNAfactsheet.PDF .

[Edited on 22-2-2005 by JohnWW]

ethanol alkaloid extraction

wallbanger - 22-2-2005 at 20:14

Hey guys,
This has already been mildly discussed, but I think is the simplist way.

Matierials:
1.75 liters of greater than 150 proof ethanol (everclear, moonshine)
2 mason jars
1 mason jar lid
a non-gas stove
cheesecloth or old T-shirt
3 or 4 packs of cigarettes

Procedure:
Start by butchering your lovely cancer inducing cigarettes by creating an incision at the top and work your way down to the filter. Extract and chop the resulting tobacco with a knife untill it is very fine. Put all of this tobacco into the mason jar and pour in you ethanol solution of choice. Don't fill the jar, just put enough in so the tobacco particles float around freely.(Sorry for lack of definitive measurments) Let this solution sit for approx. 30-60 minutes. The longer this is done the better. I do three myself.

After you feel the solution has sat long enough, place the cheesecloth or T-shirt over the other mason jar. Pour the contents of jar one into jar two through your filter. Pick up your filter and SQUEEZE all the liquid you can from the tobacco pulp. Repeat the process as much as you want.

Once your second mason jar has been filled to the amount of your liking, pour it into a wide bottomed pot or pan and place over a non-gas stove at a low to medium-low heat. Ok, I can't stress this enough, DO NOT USE A GAS STOVE!!! The ethanol vapors WILL combust in your FACE! Agitate the solution with a utensil of choice for 1.5 hours or untill the solution is thick and doesn't smell of alcohol. If you have gotten this far and didn't screw up, congratulations! You now have around 72% pure tobacco alkaloid extract and according to JohnWW, 98% of the alkaloids are nicotine. So your final product should be approx. 66.24% pure.

Not bad for a bad procedure for higschool freshman eh?

Cheapskate - 23-2-2005 at 10:42

I, sort of, tried this. What happened to me was: I used everclear 95%, not the 73% stuff in California and extracted about 50 grams of tobacco three times with it. I didn't squeeze it until the last extraction. I just let it drain through as best it could.

The idea was that I didn't want to lose much of the chopped up tobacco to the filtering cloth. That may have been a mistake since it took forever to get the alcohol to drain out. I did this extraction three times. I filtered the combined solutions three or four times to remove as much of the solids as possible.

Now I had a dark solution of alcohol that I evaporated down slowly to a syrup and raised the temperature on the syrup to 100C to be sure all the alcohol was evaporated away. This I then acidified to make nicotine.hcl and washed with ether to remove fats, oils and such.

I was in the middle of emulsion hell. Notice that there wasn't any base addition to create soaps, it just came on its own. I separated the ether as best I could and evaporated it to see what I got. There wasn't anything in the ether worth bothering with. I then raised the temp on the original extraction back to 100C to get rid of the ether.

I based it and extracted with toluene. I did get nicotine, but it was heavily laced with tars and other stuff. The heavily poluted nicotine was put in a tube where I was collecting the results of my various experiments and dissolved in acetone.

After a number of relative failures using various techniques I did an acid base extraction on the combined results and got a few grams of nicotine that is still somewhat impure, but not at all bad.

What I'm searching for (the holy grail) is a method that avoids the darn emulsions, gets at least half the available nicotine and doesn't take a week per session. Part of this has to be treating the extraction with a strong base to free the nicotine from the various salts formed by nature.

I'm going to go back to the alcohol method eventually and see if I can avoid the emulsion by taking the remains up in a non-polar solution after drying to a tar. I suspect it will leave the nicotine salts behind though.

Eclectic - 23-2-2005 at 11:32

You don't need a really strong base. Sodium carbonate is good enough.
Use acidic water (vinegar) expreso machine extraction, make alkaline with sodium carbonate, distill off 1/2 the amount of your initial aqueous extract, extract the distillate with nonpolar solvent, maybe brake cleaner (perchloroethene). Nicotine is in the perc. layer (bottom).
Hydrodistillation leaves all the organic crud from the initial aqueous extraction behind.

Also, if you are still using the tobacco insecticide dust, it may have soaps and other things added to it to help it stick to damp plants. Start with cigarette or pipe tobacco. If you never plan to kick the nicotine habit, you might try growing your own Nicotina rustica. It's supposed to be MUCH more potent than commercial tobacco.



[Edited on 23-2-2005 by Eclectic]

Cheapskate - 23-2-2005 at 13:31

One thing I'm going to start a separate thread on in the organic chemistry forum is micro distillation. At some point in this effort I will succeed and actually have some of this stuff. It would be good to distill it, but there won't be a half liter to mess with, I'll be looking at distilling, say 10ml.

Now I know how to do this if the lower boiling fraction is the part I want, but what if I want the higher fraction? I know that I'll have to use vacuum, but what kind of set up will I need. My 24/40 set up is just too darn big.

You don't need to answer here, I'll be putting it over there and I don't want to mess folks up by double posting.

Eclectic - 23-2-2005 at 16:06

Anyone have the vapor pressure of nicotine at 100C? I have 17mm-hg at 125C. I'm guessing at least 7.6 mm at 100C, so 100ml water as steam should carry over ~1 gram nicotine. Probably at most 2% nicotine in commercial tobacco, so 50g tobacco would have about 1 gram.

unionised - 24-2-2005 at 02:00

I have a couple of refs that gives 1mm at 68C and 12 mm at 116C
To a fair approximation, the log of the pressure is proportional to the absolute temperature. That should be good enough to interpolate.

fritz - 24-2-2005 at 05:27

I researched some old sources and found the following :

Nicotine is found especially in the leaves and seeds of the various tobaccos (0.68-8%). There it is bond to malic acid.
EXTRACTION:
Tobacco leaves are mixed with water for one day. The mixture is heated to 160-180 °C (by introduction of steam or over free flame) The warm mass is squeezed out and the mixture is treated again as above. The extracts are then evaporated to 1/3 of their original volume. CaO (10% of the leaves´ weight) is added and the mixture is steam-distilled. The end of the distillation is reached when the distillate lost its characteristic smell of nicotine (this is a better way then checking with indicators). The distillate is acidified with a measured amount of oxalic acid and evaporated to dryness. The residue is treated with an equivalent (referring to the acid) amount of KOH (as concentrated solution). The crude nicotine separates as an oily layer on top. The oil is separated and the aqueous phase is extracted with Et2O. Both Fractions are united and distilled under H2. The destillate is again acidified with oxalic acid and the salt is washed with Et2O, treated with KOH and distilled (again under H2). To remove most of the impurities (mainly. Et2O and NH3) the mixture is heated slowly for 2-3 °h to 210 °C. The fraction from 230-250 °C is again distilled and pure nicotine should come over at 240-242°C.
QUALITATIVE REACTIONS:
 solution in CHCl3 gives a precipitate with oxalic acid wich is soluble in EtOH (ammonium oxalate is not)
 HgCl2 gives a white precipitate which is soluble in HCl
 I2/KI gives a yellow precipitate
 Picric acid gives a yellow precipitate (m.p. 218 °C) soluble in HCl
[translated from: Einführung in das Studium der Alkaloide, Dr. Icilio Guaresci; 1896]

PURIFICATION OF (CRUDE) NICOTINE:
Crude nicotine is dissolved in an excess of H2SO4. The solution is shaken with Et2O and the nicotine is freed by KOH.
QUANTITATIVE DETERMINATION (in tobacco):
Tobacco is dried for 1-2 h at 50-60 °C. 20 g of it are ground with 10l NaOH-solution (6 g NaOH, 40 ml water and 60 ml EtOH 95%). The mixture is extracted in a ´TOLLEN´s appartus´ (never heared of this!) with Et2O. The the ether is carefully (but not completely) evaporated. The residue is mixed with 50 ml 0.1 n NaOH and steam distilled until only 25 ml remains in the flask. 100 ml of the distillate are titrated with H2SO4.
[translated from Beilstein]

SOME SOLUBILITIES:
water EtOH Et2O other
nicotine ∞ ∞ ∞ soluble in:
n-pentanol; CHCl3; petrol ether
-hydrochloride soluble soluble soluble
-salicylate
(m.p. 117.5 °C) soluble soluble soluble
-tartrate
(m.p. 88-90 °C) soluble soluble soluble

Beilstein gave the same method for extraction as the first source. The first source also gave some other slightly different methods (H2SO4 instead of oxalic acid, precipitation from Et2O-solution with oxalic acid). Also there are mentioned some other qualitative reactions but these are the typical methods of precipitating various alkaloids (PtCl2; AuCl3, etc.)
An interesting discovery is that tobaccos of poor quality should have the highest nicotine content and reverse.

To Cheapskate:
You mentioned difficulties with water/tobacco-mixtures. I didn´t make this experience when I extracted tobacco (nearly dry, from cigarettes) with some acidified water. I got something similar to tea. Otherwise if you are going to distil the extract its consistency doesn’t matter.
Very at the beginning you mentioned problems with getting solvents off the nicotine. In general this should not be a serious problem. If you have access to liquid nitrogen and some kind of vacuum-pump you may try to ´degas´ the nicotine: take the flask with the nicotine (should be round-bottom with ground joint) and connect to the vacuum pump. After reaching minimal pressure carefully cool with liquid nitrogen until the whole mass solidifies. Take the flask out of the nitrogen and wait (still the flask under vacuum) until its content is liquefied again and no more gas is bubbling out of the liquid. Repeating this a few times you should get rid of nearly every impurities (with lower b.p. than nicotine). Another method (perhaps more suitable for amateur-labs) is again to apply vacuum to the flask and then carefully heating the contents. Nicotine with a b.p. of about 250 °C will boil at 75 °C at a pressure of 1.33 mbar/1 mmHg. With a common water jet pump you should reach between 13 and 26 mbar (10-20 mmHg) and the nicotine boils between 115-140 °C in this range of pressure. Again: repeating this step a few times (or one long-time drying) will remove all solvents (especially the hydrocarbons you used). This method (as well as the above) are also suitable for handling small amounts.
For controlling purity (as well as for purification itself) I would suggest using chromatography. If you have the equipment and some experience column-chromatography should be your first choice for purification!
Here some Rf-values:

mobile phase (v/v) Rf
EtOAc/MeOH/conc. NH3 (85/10/5) 0.61
MeOH/conc. NH3 (100/1.5) 0.54
CHCl3/MeOH (9/1) 0.43-0.45
MeOH 0.39
acetone 0.13
n-hexane/acetone (8/2) 0.04
Toluene/acetone (95/5) 0.01
adsorbent in all cases is silica

One great disadvantage is: you will need LOTS of solvents/! But this would need only one perhaps expensive investment as you may redistill (and reuse) all solvents.
For controlling purity (or checking the fractions during column-chromatography) TLC may be useful. Detection of the nicotine may be carried out by viewing the plate under UV-light or by spraying with ´DRAGENDOFF-MUNIER-reagent´. This consists of two stock-solutions:
A: bismuth-subnitrate: 17 g; tartaric acid: 200 g; water: 800 ml
B: KI: 160 g; water: 400 ml
Before using both solutions are mixed in the ratio 1:1 and 50 ml of the mixture are diluted with 100 g tartaric acid and 500 ml water. Nicotine should be visible as red spots.
BUT: this is a common reagent for alkaloids! So it is important to check the Rf-values of the determined spots. These should be approximately as given above.

[Edited on 24/2/2005 by fritz]

Eclectic - 24-2-2005 at 06:52

Looks like my estimate is in the ballpark for the vapor pressure of nicotine at 100C then. I forgot to correct for molar weight though, so it may take as little as 15ml water to steam distill 1 gram nicotine. 100ml should be more than enough to carry over all traces of nicotine. That makes hydrodistillation look very atractive for the inital purification. No need to inject steam, just make the initial extract alkaline (ph 11 or higher) and distill off 1/2 the water.

[Edited on 24-2-2005 by Eclectic]

Cheapskate - 24-2-2005 at 11:49

liquid nitrogen would be difficult. I don't have the equipment to handle it. I could probably slurry acetone and dry ice if that would get cold enough.

Help me a understand something though. Almost all the patents talk about using ammonium hydroxide to free the nicotine salts before any extraction. The claim is that this brings it back to a base oil that can be extracted with solvents. The latest suggestions have been to use an acidic water solution to extract it.

I've (mostly) used a basic solution of water for the initial extraction in those instances where I try water. I have used an acidic solution (both brine and normal) to extract from non polar.

It does make sense that acidic water would take the salts of nicotine and convert any base to a salt. It might even be that an acidic extract won't take as much from the tobacco. My experience has been that neutral water will turn black when you try to extract 100grams of tobacco with 300-400 ml of water. The tobacco will also swell up and the entire mess will resist filtering. The water will become basic and soaps will form that cause emulsions that can't be separated.

Acidic water may help this, but when it is taken basic to extract with a non polar the same thing will happen, just delayed a bit.

Eclectic - 24-2-2005 at 15:43

If you want to extract into water you use acidified or neutral water. If you want to extract free nicotine into a nonpolar solvent, or steam distill directly from tobacco floating in water, you need to get the pH higher than 9-10. What was wrong with using the expresso machine? 1-2 cups extract is all you need to extract practically all of the nicotine in 50 grams tobacco. You could also use a french press (or a wine press for large amounts).

Ich habe eine idae!

wallbanger - 24-2-2005 at 19:38

Hey again,

I just had and idea! Is it possible to find what temperature nicotine evaperates at? If you know that, then couldn't you heat some water-extracted nicotine solution to that temp and collect it in a seperate container. Then heat the resulting liquid 2 degrees or so lower than previously to eliminate the impurities that evaporated with the nicotine to get a somewhat pure sample? I realize you may lose a bit of the nicotine but it does sound a lot easier than converting it to all these things that I only have a vague idea of what they even are.

neutrino - 24-2-2005 at 20:38

The problem here is that you would get appreciable losses. Chemicals evaporate at temperatures lower than their boiling points, so you final purification step would lead to very large losses.

uh huh...

wallbanger - 24-2-2005 at 21:32

I 'spose your right but...

The 2 degrees lower temp is an appoximation. The lower you do it the higher the yields will be but less pure the extracted product and instead of a test tube use a flat bottomed container to heat the second stage at a more average tempurature throughout the mixture so you don't get higher tempuratures towards the bottom. Another thing you could do is have your thermometer acctually touching the bottom so it reads higher than the real temp.

unionised - 3-3-2005 at 12:56

"Is it possible to find what temperature nicotine evaperates at?"

No.

It evaporates at every temperature. That's what the vapour pressure and temperature data mean. More will evaporate when it's hotter.

How many chemists does it take....?

Hermes_Trismegistus - 4-3-2005 at 09:12

I am really suprised at all of the difficult and complicated responses to this question.

I am almost astounded that no-one has recommended chromatography to this poor guy.

Above is a tutorial, if you can get a buret, kitty litter and common solvents you can fractionate pretty much any complex mixture you will ever find in nature.

It's fun, it's easy and they often use it (as paper chromatography) to separate out the various inks in a pen for a grade 3 science experiment.

God bless Tswett!

Hermes.

Esplosivo - 4-3-2005 at 09:28

As far as you're talking about nicotine extraction by chromotography I disagree with you. I find the filling up of the column, in column chromotography, quite a hedious job. It takes a lot of time of tapping slowly and filling, paying attention for cracks not to develop in the column. As far as I know, very fine powders, usually being of Al2O3 or SiO2 (but other lesser known 'fillers' exist, such as starch) are used. I don't think the kitty litter is fine enough. Paper chromotography, TLC and HPLC can be used to test the purity of the same collected, but surely not to obtain any amount of nicotine. Just my opinion anyways, but steam distillation seems a route which can give you quite a larger yield with 'lesser' trouble.

[Edited on 4-3-2005 by Esplosivo]

Cheapskate - 4-3-2005 at 10:29

It took me this long to finish the extractions on two water based experiments. Not very encouraging results.

In one of them I extracted using a LARGE volume of water. I used about a gallon on 100g of tobacco. The water had been acidified to ph3 and I gently evaporated it down to about 200 ml to extract. I never let the water boil and it was more viscous, but not syrupy. This was washed with 50ml of naptha twice to remove fats. Washing was a wasted effort, very little of anything was removed from the water.

Based above 11 and extracted with 2x50ml of naptha. On evaporation of the naptha I got about .5 grams of nicotine.

The expresso machine held 20g of tobacco and I ran 4 cups of water through it. I reduced the volume to around 150ml and extracted as above. Again, the wash didn't do much good and the extraction gave me an amount of nicotine that was too small to measure. A few milligrams.

In both cases there were horrible emulsions to deal with. I filtered these through steel wool and then paper filters to remove solids and such so I could get separations.

Basically any technique that involves water as the first extraction solvent is going to waste a ton of time dealing with emulsions. I'm sure that the emulsions were where mechanical losses ate up my yield.

Regarding steam distilation. This seems to carry something over into the distillate, but there is, again, a huge amount of solvent to deal with. Strangely, there is an emulsion in dealing with this distillate also. Something is carrying over that just doesn't want to cooperate. There is some promise for this technique and I may experiment with a fractional distillation of the distillate. It looks like I'll have to use a long column and do it slowly to keep the nicotine in the still bottom while moving most of the water out.

However, it's a real pain to distill a gallon and a half of water slowly to keep the nicotine from going over.

On the other front, yes I have three or four of these experiments going at a time, acetone holds promise.

Take 100g of tobacco, add 300ml of acetone and stir. The acetone takes on a yellow color and the tobacco doesn't swell up. Add a little NaOH to the stirring mix to basify the small amount of water in there and let it set stirring for a few hours.

Let the mixture set to settle and decant off as much as you can through a coffee filter. Return the solids and add a second 300ml of acetone and start stirring. You can start evaporating the first batch while the second is stirring.

After a few hours settle and decant the second batch. The second batch is more red in color than the first was. Add the second batch to the evaporating first batch and let the combination evaporate until very little is left. Add about 50ml of water and heat until the mixture reaches 95C and cool. This will remove all the acetone and leave you with a yellow mixture that has oils and some solids floating in it.

Now, acidify to ph < 2 and wash twice with naptha. I used equal volumes of naptha to water and the first wash wash was yellow with the second being clear. Then I based to ph > 11 and extracted with two equal volumes of naptha.

Evaporating the naptha gave me a relatively pure 1.5ml of nicotine. I took this up in acetone so I could pour it into a tube and then evaporated the acetone away with gentle warming. This stuff is hard to pour from one container to another.

I know I'm not done, I will need to get this even purer, and somehow, figure out how to move it from one container to another without losing a bunch of it. Maybe combining the result of several runs so the losses are easier to take would help.

Eclectic - 4-3-2005 at 15:00

I does not matter how slowly you distill basified nicotine/water: 100 ml of water as steam should carry over more than 1 gram free nicotine. Try extracting 200-300 ml distillate with (3) 30ml portions perchloroethene (brake cleaner). The free nicotine itself may be acting as an emulsifier. It's fairly soluble in water below 60C. Try bringing the concentration of Na2CO3 up to 20% to make the aqueous phase strongly ionic if you are using an extractant lighter than water.







[Edited on 6-3-2005 by Eclectic]

neutrino - 4-3-2005 at 16:48

Basifying acetone will cause polymerization products. Are you sure that your ‘nicotine’ isn’t just a large quantity of byproducts and a only a little actual nicotene?

unionised - 5-3-2005 at 08:49

Have you thought about freezing the water out of an extract?

Cheapskate - 5-3-2005 at 16:07

Regarding the acetone, yes, I'm sure it's nicotine. Remember, I'm very familiar with this substance. I can actually taste it.

I don't recommend the beginner do this for obvious reasons.

I don't use much NaOH, and I don't heat it. Most of it doesn't dissolve, it just sets in there during the extractions. There is some water in the tobacco, so what little there is is probably absorbed by the NaOH.

The brake cleaner idea is compelling. This stuff evaporates quickly so I could tell if I got anything pretty fast.

Eclectic - 5-3-2005 at 16:37

http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1...

Sodium hydroxide will also cause this reaction.
Do NOT use sodium hydroxide with chlorinated solvents!
You can make a saturated sodium carbonate solution by adding baking soda (sodium bicarbonate) to boiling water.



[Edited on 6-3-2005 by Eclectic]

Cheapskate - 6-3-2005 at 09:34

OK, I'll check it. I just took 50ml of acetone and added a few grams of NaOH to it. It's stirring right now. In a couple of hours I'll strain it then evaporate it with a few ml of water to see what happens to the water. Depending on the results, I may evaporate the water to see what is left.

I'm reluctant to add a saturated solution of water and anything to the acetone extraction. Remember the emulsion problem? These things are so bad they actually harden if left long enough.

sparkgap - 6-3-2005 at 09:41

Oh my!!! Wouldn't basicified acetone just add to your headaches by contamination with oligomerization products????

sparky (°_°)

Nicotine Evaporation

wallbanger - 10-3-2005 at 17:50

i think we should look at all the simpler methods we have here and combine them. Cheepskate is already having problems with the yeilds. th thing about nicotine in tobacco is that there isn't very much. Although the .5 grams of nicotine from 100g of raw bio-matter is pretty bad i'd say. By combining verious methods such as the ethanol and evaporating methods. start with the ethanol method and reprosses it again, then take the product of that. using ethanol i found results with a lot less emulsified plant matter. after this heat the matter to 100C with a simple distilation device and a heat source so you can get as much as you can of the remaining nicotine. add it to the ethanol extracted liquid and boil it down without acctually boiling it. 80C is recommended. from what was said some of the nicotine will be lost but this should be expected.

Uh yea, thats all i got to say.

fritz - 11-3-2005 at 15:51

I fully agree with Explosivo in the point that Column-chromatography could be a very labor-intensive method. In fact the work you have to do for obtaining rather few of the desired product is a shit! and as mentioned the packing material and the solvents are quite expensive. And I would not suggest to use crude or self-made materials for obtaining satisfactory results!
BUT:
to defend :) this method I could say from my own experience this may be better than repeated recrystallisations or destillations. Especially if you need some really pure product. And with repeated destillations you wouldn´t have less work and you risk losses of products (e.g. in decopmposition processes). Also I think especially for extractions of substances from plants where you may have lots of unwanted derivatives or just shit which could be difficult to remove and the yields are very poor (only some percents) this may be a good and effective method:P;)

mick - 11-3-2005 at 17:22

Although the .5 grams of nicotine from 100g of raw bio-matter is pretty bad i'd say.

I am curious about how much nicotine can be extracted from tobacco. Considering the toxicty of pure nicotine I would have thought 0.5g in a 100g is a lot. I think 20g of tea has 0.1 to 0.2g of caffeine and caffeine is no where near as toxic as nicotine

mick

Remeber dosages

blazter - 12-3-2005 at 11:15

Looking from a potency standpoint, seemingly small yeilds of 500mg nicotine isn't really that bad. The commerical Rx nasal inhalers give something like .5mg per squirt, and the gum comes in 2 or 4mg dose units. Granted these doses are probably a bit less than a desireable recreational dose, they are still effective doses. Consider, that with a 2mg serving size, that measly .5g of nicotine should give about 250 servings.

On a side note, I remember reading some figures where a standard serving of tea contained about 50mg of caffiene. Tea also contains other bioactive principals.

Cheapskate - 13-3-2005 at 11:09

Steam distillation just doesn't seem to work. If you distill it slowly, it takes a lot, liters, of water to get the yellow to stop coming over. If you distill it fast recommended) it burns the tobacco to the sides of the flask.

I took the 3.5 liters of water I had and distilled it again with a 400m reflux column to concentrate the nicotine int a much smaller amount of water. The distillate was clear, smelled slightly of tobacco. The bottom was a viscous dark tarry looking mess. However, I extracted this with 2x50 of naptha and evaporated.

Nice black tar was my reward. Inactive and full of hydrocarbons. As to expected yields, the literature quotes 3% to 10% depending on the article, so if I get half of it I should be able to pull 1.5 grams out of 100grams of tobacco. It just isn't happening.

I haven't seriously tried alcohol since I would have to distill to get it, but it may be more selective than the acetone. Strangely, my best results were with an MEK extraction, but this stuff dissolves in water 1 part to 4 so it's difficult to separate without losing a bunch.

I like the idea of combining the various techniques. Maybe an extraction with MEK, evaporate this. Then dissolve what's left in alcohol (denatured should be fine) to separate what will dissolve in a polar from what will dissolve in a non polar. Evaporate that and do an acid base on the result.

Different tack

Minus459F - 14-3-2005 at 14:52

Wow. OK, you guys are an order of magnitude more skilled in chemistry than what little I remember from college. But I did have a different idea on this topic. I am in the middle of an experiment. I made some tea out of a half pound of pipe tobacco. The idea was to flocculate out the organics. I added aluminum sulfate and tried to get the ph up with sodium bicarb (I didn't know the trick of boiling it to get NaCO. Thanks, I'll try that to up the ph). I got some substantial flocculation but not enough to begin to clarify the product. I'm going to try to distill this goo and then try my flocculation on the distillate and see what happens.

If I'm barking up the wrong tree, feel free to tell me so :)

alkaloids

wallbanger - 14-3-2005 at 19:39

Just remember people, nictine is an alkaloid. so just use processes to extract alkaloids. what we need to find is a solvent that dissolves nictine, and not much (preferably any) of the byproducts. Ive used both ethanol and methanol extractions and have gotten large yields of around 2g to 100g with it being approx. 60% pure nicotine. The alchohol solvents dissovle all alkaloids (THC, nicotine, CBNs) and evaporate at low temperatures. things like tar and other carcinogens stay behind while the alkaloids stay in the extracted solution. acetone works ok and evaporates at higher temperatures, not to mention it smells like shit. thats my 2 cents.

nicotine extraction

Randall Rose - 15-3-2005 at 11:38

I started thinking about this a year ago. I remembered that nicotine absorbs into plants and thought maybe this could be used to separate nicotine. I boiled three cans of smokeless tobacco in enough water to cover a apple that I would later be used to separate the nicotine. After cooling I put the apple in a container with the tobacco juice. I covered it and left it there for one week.
Then I washed the apple, cut it up and put it in the blender. I separated the juice and filtered it. Next, I took one drop and put it on my skin to make a patch. Whow! One drop turned out to be a overdose. I started showing all the signs of a small overdose. Since then I have continued to separate in this way. Only now I only use one can of tobacco and I am much more carefull. Anyone who tries this must remember to use rubber gloves to prevent absorbsion though the skin.
I have also found that boiling the final product stops it from breaking down as fast. Please be very careful doing this! It only takes about 60 ml nicotine to kill and this has much more than that. Extreem danger

Minus459F - 16-3-2005 at 09:40

Are you serious?

A minor correction

blazter - 16-3-2005 at 13:22

I couldn't help but notice a couple posts earlier THC being confused with being an alkaloid. This seems to be a fairly common bit of misinformation that I cant stand to listen to. THC contains no nitrogen atoms, not polar and is NOT ALKALINE (basic).

Also, I suppose it may be possible to use a peeled apple to absorb nicotine. I've heard that the Russian army used to drink radiator fluid which was soaked in potatoes to spposidly absorb the denaturatants from the alcohol. Though this method does seem sort of ineffecient and time consuming, and still has the same issue of boiling tobacco in water which seems to swell up, and not leave much water behind. The method that seems the bost promising so far is the acetone extraction followed by some sort of acid/base extraction on the first extracts.

unionised - 16-3-2005 at 14:28

Well, it's not an alkaloid, it's not really basic, but it is quite polar, its the phenolic group that does it.
Anyway, the idea of using an apple is weird but plausible. The nicotine will difuse through the oily layer on skin of the apple and react with the (mainly malic) acid to give a salt which will not difuse back.

Cheapskate - 16-3-2005 at 14:37

An APPLE! That is way cool. I never, ever, would have thought of using a fruit to absorb nicotine.

In defense of the idea, I do know for a fact that nicotine will absorb rapidly into substances. I once used raw nicotine oil from a commercial supplier to permeate a damp paper towel. This is a method of making poor-man's lozenges. If you use a little bicarbonate of soda in the water it will help keep the nicotine from decomposing. Keep the towel pieces sealed from the air since the nicotine and water will evaporate away in a short amount of time.

My experiments are continuing. The one running now is an extraction with MEK. I put 100ml of MEK in a flask with 100g of tobacco and stirred overnight. Filtered the MEK and recovered about 50ml after multiple filterings to remove as much of the solids as I could. To this I added 50ml acidified water and set aside to evaporate. After as much of the MEK as would reasonably depart I heated the water to just under 100C to force off the remaining MEK then cooled. This left yellow water and an incredibly sticky tar. The tar would stick to anything that touched it, glass, fingers, stirbar, etc. I filtered this cleaned the glassware and filtered again. Brake cleaner from the other experiments works well to remove the tar.

I washed the acidic water twice with 25ml of naptha to remove any unseen remains, and then back extracted the naptha with 25ml of acidic water just in case some nicotine sneaked out that way.

Now I'm going to basify, salt and extract to see what I get.

frog - 16-3-2005 at 16:46

Yes! This is reverse osmosis and you get pure nicotine. Nicotine is odorless and this does not smell like tobacco. All the other parts of tobacco are filtered out. If you would like to know exactly how I do it e-mail me.
The biggest problem I have is that the nicotine breaks down and only lasts about two weeks. Maybe someone has an idea to stabilize it.
I have two daughters who both smoked and gave up smoking by using this like a patch. I use it for enjoyment.

Cheapskate - 16-3-2005 at 16:49

Crap, I think I may know why the yields are so damn low. Evaporation. It came to me thinking about the paper towel above.

If you put a drop of raw nicotine on a piece of paper it will make a yellowish brown spot. If the nicotine is pure, the spot will disapear in about a day. If I'm using naptha and evaporating it to get the nicotine, how much am I losing to normal evaporation? If I heat it because I'm impatient, how much more do I lose?

I'll bet that if I go to ether for the last extraction and then evaporate it I'll get more yield, but I would have to set there and watch it to grab the nicotine as soon as it goes away.

Damn I wish I could precipitate one of the salts out of solvent! It would be way easier to purify through recrystalization than setting watching ether evaporate. I also hate distilling ether to get rid of the hydrocarbons they add to starting fluid. Same thing with brake cleaner, they add stuff that forces distillation to clean it up.

Yes, I know how to make chloroform! But you have to distill this stuff as well to get it clean enough. Not that distillation is that big a problem, it's just setting up the equipment and tearing it down to get clean solvents is such a pain. I guess doing it in large batches would make it somewhat easier...and smellier.

oops!

wallbanger - 16-3-2005 at 16:54

Yea, blazter ist right. THC is not an alkaloid. It is though, basic and pretty polar but this does not pertain to this discusion board. nicotine however, is. a question for cheepskate, what is naptha? is it naphthamine, the stuff from moth balls? and what are its chemical properties?

[Edited on 17-3-2005 by wallbanger]

wallbanger - 16-3-2005 at 17:00

heyfrog, whats your email man? i checked your profile and its not there. im pretty interested in the reverse osmosis of nicotine. the thing with the apple isnt reverse osmois though, its plain osmosis. reverse osmosis it when a substance is forced from a area of low concentration to lhigh concentration with regular osmosis being the other way around. at least thats what ive been told.

[Edited on 17-3-2005 by wallbanger]

Cheapskate - 16-3-2005 at 17:10

Naptha is a petroleum distillate. Basically what they do is distill crude oil and take off the products at different temperatures and call them things. The lowest boiling fractions are butane and propane, then petroleum ether, naptha, gasoline, kerosene etc.

There are several things called naptha some boil at temps higher than water. The one I'm using is VM&P naptha (Varnish Makers and Painters) this stuff boils around 80C so it goes away faster than water.

Yes, I know this is incredibly simplified, but it gets the idea across.

solvents

wallbanger - 17-3-2005 at 19:19

ethanol and other alcohol solvents also boil around 80C, so why naptha? there are other petrolium distilates like ether that biol below room temperature. My phrasing may have benn a little off, but the point of the question was to acertain why you use naptha. is it personal preferance? I use ethanol as my primary extraction solvent due to its ease to create (moonshine) and other various "uses".

Cheapskate - 18-3-2005 at 12:29

Oh, I understand now. I use a non-polar as the initial solvent because I started this process by dumping some basified water in the tobacco to convert the nicotine salts back to the base and to free up the nicotine from the solids. But, since I couldn't get the water back (it got hung up in tobacco jelly that formed) I would add a non polar to the mix to take up nicotine.

I started with Kerosene because it has an incredibly good partition coeficient. It actually takes nicotine from water. However, the darn kerosene left a really bad pollution of high boiling point hydrocarbons that I couldn't find a way to get rid of. Hence, naptha.

See when the target product is for consumption you want a clean evaporating solvent that separates well from water and then evaporates completely. That's why kerosene is off my list for now, you just can't get rid of that stuff. It's also why I have to distill commercially available ether, the "top cylinder oil" they put in there has a boiling point over 200C, it's almost impossible to get rid of also.

I wound up with acetone because I thought it would be easier to evaporate since there are significant losses to extractions. With only a few grams available, every little loss is a big deal. I'm about ready to go back to kerosene and try dealing with the hydrocarbons as a separate problem.

Cheapskate - 15-4-2005 at 11:52

OK, to close this off and leave something for others attempting this same item, I finally did it. There were a large (really large) number of problems as detailed previously, but I've found a way of getting the nicotine out of tobacco on a small scale that can be handled at home.

First though, the tobacco chosen is important. For example, good old rolling tobacco you buy in bulk at the discount cigarette store works great. Marlboros have too many additives that mess up the works. Tobacco dust sold in four pound bags works well, but there is actually very little nicotine in it. Something in the processing is removing the nicotine.

So go get the cheap rolling tobacco that has already been ground up.

The initial extraction is to use around 100 grams of tobacco and 300ml of kerosene. Yes, I know that I swore off this stuff because it left a taint to the nicotine, but I found a way to remove it later. Also add 50ml of 40% sodium hydroxide solution to the mix. This frees the nicotine from the salts in the tobacco and helps break down the cellular walls.

Let this set with occasional stirring for 24 hours. The tobacco will swell some and the mix will increase in viscosity. Filter and squeeze through cloth to get all the liquid you can and put the tobacco back in the container for another kerosene extraction with 200 ml this time. Note that you won't get the 300ml back, you'll be lucky if you get 200ml out of the tobacco and the water will have disapeared. 24 hours later filter and squeeze what you can out of the tobacco and just throw it away. Further extractions are an exercise in futility.

Combine the kerosene fractions and set them aside while you prepare a solution of 20ml 30% hydrochloride and 80 ml of water. Just use the old driveway cleaner from the local building supply. Extract once with 50ml of the acidic water and a LOT of stirring, shaking, whatever. The kerosene layer will be on top and will turn a milky yellow color. The water layer, bottom, will turn an amber color; separate and repeat the extraction with the other 50ml of acidic water.

The kerosene can now be discarded or set aside (just in case). The amber water needs to be washed with a little VM&P naptha. Use about 30ml and mix well so it can take up all the left over kerosene. This is the stage where you get rid of the nasty kerosene. Basify to ph>10 with 40% water solution of NaOH and add enough salt so no more will dissolve.

This is where it gets interesting. The basic salt-saturated solution will cause the nicotine to separate at temperatures over 60C. So, just for fun take the temperature up to around 70C and you'll see the oil separate and rise to the top as a separate (very small)layer. This isn't pure nicotine, but includes all the alkaloids and some other contaminants. But it does give one a good idea what you're going to get.

Cool, filter out the solids, and extract twice with 30ml of naptha. Evaporate the naptha at room temperature and you have a small amount of relatively pure nicotine. There isn't enough here to do much with, so dissolve in acetone and save. Repeat the entire procedure saving the nicotine in acetone until you have enough to deal with. I use 4 of the full extractions to get enough nicotine to further purify.

Further purification. The right way to do this is a vacuum distillation under an inert gas, but most of us don't have the equipment to do that so.... First evaporate the acetone at room temperature and dissolve the nicotine in basic water (ph> 11). Extract with pure (distilled) ether. This is important since the ether one can get at the auto parts stores has contaminants in it. You can find instructions on distilling ether on the web, just be sure to keep flames away and use good ventilation. Evaporate most of the ether and use the small amount left to help you pour the fluids into a container for storage. Evaporate the last of the ether from your container by warming slightly and you're done.

If you have the equipment, you can scale this up to larger amounts of tobacco and cut down the effort. One can even arrange a pump to pump the kerosene through the tobacco to extract on a continuing basis and do an acidic water extraction in line by letting the kerosene bubble up through the acidic water before being returned to the tobacco. With a little screening and filtering this could be set up to produce reasonable quantities of high percentage nicotine. The surprising part is how little nicotine there actually is in tobacco. One would think there's 4 or 5 grams in each 100 grams of tobacco, but I just couldn't find it. I did get as much as 3 grams on the first pass, but that was as good as it got and only happened once. So, keep your expectations in check and proceed.

Archimede - 13-5-2005 at 17:37

I remember a friend of mine that at a bar was blowing the smoke of his cigarette in a glass of water with a straw. After a while the water was really nasty....
Maybe burning tobacco and having the smoke go thru a cold liquid of your choice (I don't know chemistry) then you can try to extract it from there.

[Edited on 14-5-2005 by Archimede]

HNO3 - 13-5-2005 at 17:54

Yikes! I'm doing something I never thought I would...

I didn't read the entire thread, but has anybody suggested using "Rabbit Repeller" or something like that from a garden center? I saw some today that said it had 0.35% nicotine in it.

lordmagnus - 4-3-2006 at 23:01

The easiest way would be to use the liquid co2 method, the FOLGERS plant in Houston does it that way, they run liquid co2 thorugh a filter membrane with processed coffee in it, the co2 pulls out all the caffeine, they then vacuum distill the co2 off and recompress, the result is caffeine base wich they sell to the makers of VIVARIN, and No DOZE (seriously they do!). but the mechaincs is hard to setup on a household scale., even in a small lab setup, were talking some quality copper pipe, flare fittings, a compressor/vacuum pump capable of comrpessing co2 to a liquid state, etc.

neutrino - 5-3-2006 at 08:28

That's supercritical CO<sub>2</sub>, not liquid CO<sub>2</sub>. There is a huge difference.

wallbanger - 6-3-2006 at 09:24

Anyone ever try vaporizing the nicotine out of the tobacco? It'd be pretty impure but it would be easier to do that then wait 48 hours if it worked.

thedestroyer5150 - 15-4-2006 at 04:54

All I have to say is: http://www.chemistry.ohio-state.edu/~mathews/Ohio_Project/re...

The entire SFE/Solvent extraction process is described in general terms for nicotine and caffeine.

JohnWW - 15-4-2006 at 10:15

A point that has been overlooked is: how pure is the nicotine that can be extracted from tobacco? As well as nicotine, I am sure that tobacco would contain structurally-related alkaloids having similar physiological properties, consisting of nicotine with, for example, added methyl or methoxy groups. There must be some literature on this somewhere.

Mr. Wizard - 15-4-2006 at 16:34

I know tobacco is common and available, but I obtained some seeds and I'm growing some. The seeds are very tiny, smaller than the period at the end of this sentence. Anyway you have to plant them on top of the soil and keep them moist for a month, and then water them for another month until the leaves get 1 cm in diameter. They then can be placed outdoors. They are very labor intensive. The plants are supposed to get over 6 feet tall ( about 2 meters). If anyone is interested I'll post some photos. Has anyone else ever cultivated any?

The_Davster - 15-4-2006 at 17:06

I worked at a greenhouse one summer and saw the plants, a good 5ft tall, the leaves are very large. They got them from their supliers as little plants so I never had to cultivate them from seed.

JohnWW - 15-4-2006 at 17:47

Can anyone post the names and addresses of suppliers of tobacco seed? I would like to grow some for their nicotine, as a source of chemicals and particularly for an organic insecticide.

jarynth - 6-9-2008 at 19:26

Googling "tobacco seeds" will turn up a plethora of sellers.

Precipitation from water with picric acid seems to be the only lab route to isolation of nicotine. Check for instance the very detailed account in the following paper:

http://www.publish.csiro.au/?act=view_file&file_id=CH951...

[Edited on 6-9-2008 by jarynth]

Attachment: NicotineIsolation.pdf (265kB)
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Isolation of nicotine

tapira1 - 7-9-2008 at 08:30

Look in here. Beware pure nicotine is highly toxic and may kill you

Attachment: IndianJPharmSci68188-4495678_122916.pdf (97kB)
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Nicotine and nicotinic acid

tapira1 - 7-9-2008 at 08:35

There is plenty of li. This may help

Attachment: JBC Nicotine.pdf (387kB)
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jarynth - 7-9-2008 at 14:18

Quote:
Originally posted by tapira1
Look in here. Beware pure nicotine is highly toxic and may kill you


This doesn't say much more than that the methanol extract "was
subjected to separation of alkaloids by reported standard
procedure12 with slight modification" and that "problems with purification in method 1 prompted us to follow conventional distillation used for the separation of volatile alkaloids12."

[Edited on 7-9-2008 by jarynth]

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