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Author: Subject: Nicotine Extraction and purification
blazter
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[*] posted on 16-3-2005 at 13:22
A minor correction


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.
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[*] posted on 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.
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Cheapskate
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[*] posted on 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.
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frog
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[*] posted on 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.
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Cheapskate
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[*] posted on 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.
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wallbanger
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[*] posted on 16-3-2005 at 16:54
oops!


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]




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[*] posted on 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]




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Cheapskate
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[*] posted on 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.
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[*] posted on 17-3-2005 at 19:19
solvents


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".



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[*] posted on 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.
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[*] posted on 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.
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[*] posted on 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]
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[*] posted on 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.




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[*] posted on 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.



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[*] posted on 5-3-2006 at 08:28


That's supercritical CO<sub>2</sub>, not liquid CO<sub>2</sub>. There is a huge difference.
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[*] posted on 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.



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[*] posted on 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.




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[*] posted on 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.
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[*] posted on 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?
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The_Davster
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[*] posted on 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.



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[*] posted on 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.
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[*] posted on 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]

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[*] posted on 7-9-2008 at 08:30
Isolation of nicotine


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

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[*] posted on 7-9-2008 at 08:35
Nicotine and nicotinic acid


There is plenty of li. This may help

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jarynth
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[*] posted on 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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