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Author: Subject: Nicotine Extraction and purification
Cheapskate
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[*] posted on 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.
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Eclectic
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[*] posted on 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).
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[*] posted on 24-2-2005 at 19:38
Ich habe eine idae!


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.




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neutrino
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[*] posted on 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.
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wallbanger
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[*] posted on 24-2-2005 at 21:32
uh huh...


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.




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[*] posted on 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.
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[*] posted on 4-3-2005 at 09:12
How many chemists does it take....?


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!

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[*] posted on 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]




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[*] posted on 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.
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[*] posted on 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]
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neutrino
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[*] posted on 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?
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[*] posted on 5-3-2005 at 08:49


Have you thought about freezing the water out of an extract?
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[*] posted on 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.
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[*] posted on 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]
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[*] posted on 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.
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[*] posted on 6-3-2005 at 09:41


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

sparky (°_°)




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[*] posted on 10-3-2005 at 17:50
Nicotine Evaporation


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.




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[*] posted on 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;)
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[*] posted on 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
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[*] posted on 12-3-2005 at 11:15
Remeber dosages


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.
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[*] posted on 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.
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[*] posted on 14-3-2005 at 14:52
Different tack


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 :)
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[*] posted on 14-3-2005 at 19:39
alkaloids


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.



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[*] posted on 15-3-2005 at 11:38
nicotine extraction


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
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[*] posted on 16-3-2005 at 09:40


Are you serious?
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