Tobacco extraction using heated Ethanol

[twgbonehead]

Str8,

Since you seem to know a lot more about this than I do, I was wondering if you know if this would work.

First, you either want to do some kind of straight-water extraction and then add a base, or do an extraction with a high-ph water.
In the paper, they mentioned using lye. It's fairly commonly available, but not the safest thing to have around. I was thinking instead of the possibility of using Sodium Carbonate, either bought, or made by heating baking soda in an oven.

Anyway, once you have the extracted, alkaline "tobacco water" you distill it (perhaps using the "pot-in-pot, inverted ice-filled lid" technique.

The distilled liquid would then need to be acidified. While the paper references sulfuric acid, I was wondering whether lemon juice or (freezer-concentrated) vinegar would work? Add one of these to the distillate, and evaporate the results down to some concentration (either before crystallization, or all the way down). Then, adjust the pH back up (using the same base as for the first step) and dilute with PG to make the liquid.

If I understand correctly, the first stage should extract out all the alkaloids, leaving behind the acids and solids. The second stage should get rid of all the acids (introduced in the second stage) leaving behind mostly what was alkaloid in the first place.

Would this work? Are the bases and acids I've suggested strong enough (or otherwise appropriate) to do an efficient extraction?
(And it doesn't have to be all that efficient; in the original paper, 500g of tobacco (a little more than a pound) yielded 11g of nicotine, which would make about 650ml of 16-mg liquid.)

But, moreover, if I understand the acid/base extraction, this should get most of the alkaloids, not just the nicotine. And leave behind most of the stuff that's not really desired.

Even if we needed to use lye and sulfuric acid, these are reasonably available (just that I'd prefer to not have them in my house, and worries about neutralizing properly before vaping.)

Thoughts?

 

[Str8vision]

................I would also strongly suggest that this be done outside! If everything goes as planned this is likely to be a safe procedure, but if something goes wrong this could end up quite badly....

This method is certainly not as carefree as a room temperature PG soak. Heating ethanol near its boiling point could, if it boils, produce pressure inside the glass container which is why I prefer to use half pint canning jars, designed for heat and pressure. As when canning food, I only "lightly" seal the lid so any pressure build up can easily vent otherwise the jar might break spilling its contents into the water bath. I learned that lesson the hard way while canning food in a pressure cooker with one of the jars sealed too tightly. Cold or hot, ethanol smells terrible (to me anyway), and should be used in a well ventilated environment.

 

[twgbonehead]

Actually the part of the document where you took that text from is the intro, where they go over the existing methods that they researched.

The study is actually focused on the extraction and doesn't describe any method for concentrating or purifying the extract.

Well, you are correct about the first part, but I don't think you are correct about the second. And yes, I quoted the wrong part of the paper.
What you also need to realize is that what they are trying to do is twofold:
1. Extract the nicotine from tobacco in a way that provides useable nicotine solutions
2. Leave the tobacco in a state suitable for use in low-nicotine cigarettes (therefore involving minimal damage or contamination to the tobacco leaves).

In the detailed process (which starts on page 18) they DO perform the extraction with plain water. This apparently works, does not damage the tobacco much, but results in a very dilute nicotine solution. Goal 2 accomplished, they've created tobacco with a low-nic content, without damaging it much.

But they also accomplished Goal 1 (sorry for the formatting, this stuff cuts-and-pastes pathetically):

The fractions, lA, 2A, 3A, 4A, 5A, B, C, D and E were combined to yield 3210 ml of a dark solution . To
this was added 200 ml of 50% sodium hydroxide solution and this mixture was distilled as rapidly as possible
to yield 3250 ml of a clear yellow solution. Analysis by capillary GLC indicated 11.3g (78%) of nicotine was
recovered.
The distillate was brought to pH ti4 with concentrated sulfuric acid and evaporated on a hot plate to 25 ml.
Upon cooling the black solution partially crystallized. Addition of 10 ml of distilled water brought the solids
back into solution

(sodium hydroxide is lye). The above excerpt is from page 19.

 

[Str8vision]

Str8,

Since you seem to know a lot more about this than I do, I was wondering if you know if this would work.

First, you either want to do some kind of straight-water extraction and then add a base, or do an extraction with a high-ph water.
In the paper, they mentioned using lye. It's fairly commonly available, but not the safest thing to have around. I was thinking instead of the possibility of using Sodium Carbonate, either bought, or made by heating baking soda in an oven.

Anyway, once you have the extracted, alkaline "tobacco water" you distill it (perhaps using the "pot-in-pot, inverted ice-filled lid" technique.

The distilled liquid would then need to be acidified. While the paper references sulfuric acid, I was wondering whether lemon juice or (freezer-concentrated) vinegar would work? Add one of these to the distillate, and evaporate the results down to some concentration (either before crystallization, or all the way down). Then, adjust the pH back up (using the same base as for the first step) and dilute with PG to make the liquid.

If I understand correctly, the first stage should extract out all the alkaloids, leaving behind the acids and solids. The second stage should get rid of all the acids (introduced in the second stage) leaving behind mostly what was alkaloid in the first place.

Would this work? Are the bases and acids I've suggested strong enough (or otherwise appropriate) to do an efficient extraction?
(And it doesn't have to be all that efficient; in the original paper, 500g of tobacco (a little more than a pound) yielded 11g of nicotine, which would make about 650ml of 16-mg liquid.)

But, moreover, if I understand the acid/base extraction, this should get most of the alkaloids, not just the nicotine. And leave behind most of the stuff that's not really desired.

Even if we needed to use lye and sulfuric acid, these are reasonably available (just that I'd prefer to not have them in my house, and worries about neutralizing properly before vaping.)

Thoughts?

My work has been focused exclusively on extraction of flavor using non-toxic solvents. I haven't any experience with the process or techniques you've outlined so can't be of much help. A retired mechanical engineer, I know just enough chemistry to get myself into trouble. I will say this, two years ago I was concerned the FDA and or states might ban or excessively tax the public sale of liquid nic. After considerable research and seeing the chemicals/process used to manufacture it, I decided against pursuing nicotine extraction and instead opted for bulk storage. Considering my age, I can store enough $50 per liter 100mg liquid nic to easily see me through.

If I - had - to rely on my tobacco extractions for nic content I would likely go in a different direction. I would focus on using ethanol and or water based extraction methods exclusively since they can be easily reduced/condensed by vacuum distillation thereby concentrating the available nic. I would experiment with submicron filtration in efforts to "reduce" flavor so that I could use higher percentages of extract (and therefor nic), when mixing a vapable NET. I would also pursue obtaining Rustica, Y-1, Fumo louco and other strains of "ultra high-nicotine" tobacco to play with. I believe, but don't know for certain, that 3mg flavorful NET might be a real possibility and it could be vaped sub-ohm for TH and impact rivaling what I'm currently producing/mixing. It would take - a lot - more tobacco than what I currently use but the day may come where doing so is actually cost effective.That's just my thoughts on the matter.

 

[Bagazo]

Well, you are correct about the first part, but I don't think you are correct about the second. And yes, I quoted the wrong part of the paper.
What you also need to realize is that what they are trying to do is twofold

I also pointed that out. Extract nic and keep the leaf in usable condition.

Distillation is not acid/base extract. Acid/base is a liquid-liquid extraction.

Also you seem to be mistaking the description of how they quantified the nicotine extracted as part of the study but it reads like they only did it to the first batch and didn't bother doing the same for the rest of the water extracts.

ETA: I don't see how that changes the fact that these extracts do contain nic. I mentioned earlier, acid/base, distillation or whatever method you want to try, you cannot get more nic than what the original extract (single or multiple) contains. It only changes the concentration:

1% nic in 10ml = 10% nic in 1ml.
The amount of nic doesn't change.

 

[gt_1955]

Actually, the methods listed in the paper cited by Bagazo are an acid/base extraction (perhaps more accurately, a base/acid extraction). The water used for the extraction is alkaline (using ammonia, lime, or lye), and even so, the resulting liquid only gets to about 1% nicotine. (It extracts a high percentage of the nicotine from the tobacco, but needs a lot of water to do this, so the resulting solution is dilute). They then acidify the water, and distill it. From the paper:

Yes, perhaps ... but I was specifically referring to cold maceration over 90+ days Which I do for flavour only.

...

Acid/base extraction is used to clean up the alkaloids after the initial extraction. It won't get you more nic than what was extracted in the first soak. Actually you loose a bit every time you from acid to base or back although using less liquid in subsequent extractions can give you a higher concentration.

Surely you perform a base/acid extraction from the tobacco leaf, and not after a solvent extraction? That's how I do it (based on tceight's work) anyway.

 

[gt_1955]

Str8,

Since you seem to know a lot more about this than I do, I was wondering if you know if this would work.

First, you either want to do some kind of straight-water extraction and then add a base, or do an extraction with a high-ph water.
In the paper, they mentioned using lye. It's fairly commonly available, but not the safest thing to have around. I was thinking instead of the possibility of using Sodium Carbonate, either bought, or made by heating baking soda in an oven.

Anyway, once you have the extracted, alkaline "tobacco water" you distill it (perhaps using the "pot-in-pot, inverted ice-filled lid" technique.

The distilled liquid would then need to be acidified. While the paper references sulfuric acid, I was wondering whether lemon juice or (freezer-concentrated) vinegar would work? Add one of these to the distillate, and evaporate the results down to some concentration (either before crystallization, or all the way down). Then, adjust the pH back up (using the same base as for the first step) and dilute with PG to make the liquid.

If I understand correctly, the first stage should extract out all the alkaloids, leaving behind the acids and solids. The second stage should get rid of all the acids (introduced in the second stage) leaving behind mostly what was alkaloid in the first place.

Would this work? Are the bases and acids I've suggested strong enough (or otherwise appropriate) to do an efficient extraction?
(And it doesn't have to be all that efficient; in the original paper, 500g of tobacco (a little more than a pound) yielded 11g of nicotine, which would make about 650ml of 16-mg liquid.)

But, moreover, if I understand the acid/base extraction, this should get most of the alkaloids, not just the nicotine. And leave behind most of the stuff that's not really desired.

Even if we needed to use lye and sulfuric acid, these are reasonably available (just that I'd prefer to not have them in my house, and worries about neutralizing properly before vaping.)

Thoughts?

http://www.e-cigarette-forum.com/forum/blogs/tceight/1412-kitchen-wta-extraction-method.html

(Apologies if posting this is not permitted)

 

[gt_1955]

@Str8vision ... I bought the last piece needed today to try your heated ethanol method, but that will have to wait now until next weekend so I can keep an eye on it (it's 9:30PM Sunday night here). Cheers for sharing this mate

 

[Str8vision]

@Str8vision ... I bought the last piece needed today to try your heated ethanol method, but that will have to wait now until next weekend so I can keep an eye on it (it's 9:30PM Sunday night here). Cheers for sharing this mate

Fantastic, hope you enjoy the results as much as I have. During the past two years I've experimented with PG, VG, Ethanol, Water and various blends of these solvents using hot and cold extraction methods of varied duration and temperature combinations. I've even ran concurrent and sequential extractions (multistage), combining the attributes obtained from different solvents/extraction methods into a single extract. Many hundreds of experiments and the heated ethanol is as robust and flavorful as my best multistage efforts. It also seems to produce a very pure, accurate flavor whereas PG and VG extractions are all, to varying degrees, muddied. I hope this result continues to hold true as I extract additional, distinctly different, tobacco blends.

The amount of waxes and oils that are pulled will become apparent after the freeze cycle. The freezer I use for this step (and for storing liquid nic), is kept at -10F (-23C). One thing I found quite surprising was after filtering the cold ethanol through a coffee filter I allowed it to sit at room temperature, sealed in a glass container for a week expecting some oil to coalesce and form a film on the surface. None appeared in any of the containers. I then vacuum filtered the ethanol through 1 micron glass filter paper and was again surprised by (1); how fast it filtered, and (2); how little material was captured by the filter, it was only lightly discolored. My thought is that the freeze cycle and subsequent coffee filter pass was highly effective.

I haven't transferred any of the flavor to PG yet and likely won't. I have around 30ml of ethanol extract from each of the tobacco blends I experimented with and plan on reducing (concentrating), one of them down to 10ml and evaluate the results. I do think it's past time I stopped evaporating (losing), the ethanol and start recovering it through vacuum distillation, I have the gear so why not use it. In the past year I've likely "wasted" a hundred dollars worth of ethanol through evaporation.

My next round of experiments will focus on "fine tuning" the extraction process. I had previously ran batches at ~160F (~71C), for 2, 4, 6 and 8 hours but wasn't overly impressed with the results. I'm relatively satisfied with the temperature used for the extraction but will continue varying the processing time seeking the upper and lower limits. As always, flavor will be the determining factor.

On a lighter note, I've been using the extract of Sutliff's "Voodoo Queen" at 4 - 6% to flavor Nicoticket's "Absolut Crème Brulee" (ACB), and Charlie Noble's "Tripoli"..... Delicious.

 

[Bagazo]

Surely you perform a base/acid extraction from the tobacco leaf, and not after a solvent extraction?

Acid/base referes to the switching back and forth to polar and nonpolar solvents while at the same time using acid and bases to change the solubility of the alkaloids in each. It is called a liquid-liquid extraction because you are extracting the alkaloids from one liquid into another.

Freebase alkaloids are insoluble in polar solvents so when you use a base to turn the solutions alkaline the freebase alkaloids are absorbed by the non-polar solvent. You discard the polar solvent then use an acid to turn the solutions acidic. This turns the alkaloids into salts which are now insoulble in the non-polar solvent and soluble in the polar solvents causing them to migrate into the polar solvent.

You can't just do a simple extraction on tobacco and call it acid/base. The initial extraction can be, and usually is, the first step in acid/base extraction but without the following steps it isn't acid/base.

 

[gt_1955]

Fantastic, hope you enjoy the results as much as I have. During the past two years I've experimented with PG, VG, Ethanol, Water and various blends of these solvents using hot and cold extraction methods of varied duration and temperature combinations. I've even ran concurrent and sequential extractions (multistage), combining the attributes obtained from different solvents/extraction methods into a single extract. Many hundreds of experiments and the heated ethanol is as robust and flavorful as my best multistage efforts. It also seems to produce a very pure, accurate flavor whereas PG and VG extractions are all, to varying degrees, muddied. I hope this result continues to hold true as I extract additional, distinctly different, tobacco blends.

The amount of waxes and oils that are pulled will become apparent after the freeze cycle. The freezer I use for this step (and for storing liquid nic), is kept at -10F (-23C). One thing I found quite surprising was after filtering the cold ethanol through a coffee filter I allowed it to sit at room temperature, sealed in a glass container for a week expecting some oil to coalesce and form a film on the surface. None appeared in any of the containers. I then vacuum filtered the ethanol through 1 micron glass filter paper and was again surprised by (1); how fast it filtered, and (2); how little material was captured by the filter, it was only lightly discolored. My thought is that the freeze cycle and subsequent coffee filter pass was highly effective.

...

Thanks

I have been cold filtering my cold macerated steeps with a similar process to you ... after initial filtering, place steep into and leave in the freezer for 3 days and filter whilst still in the freezer. Bit of a slow process (no vacuum filtering here), but I have time on my side (now ). I believe it produces a cleaner steep, which I've been mixing at 4% along with my nic and PG to form my vaping liquid.

 

[twgbonehead]

I also pointed that out. Extract nic and keep the leaf in usable condition.

Distillation is not acid/base extract. Acid/base is a liquid-liquid extraction.

Also you seem to be mistaking the description of how they quantified the nicotine extracted as part of the study but it reads like they only did it to the first batch and didn't bother doing the same for the rest of the water extracts.

ETA: I don't see how that changes the fact that these extracts do contain nic. I mentioned earlier, acid/base, distillation or whatever method you want to try, you cannot get more nic than what the original extract (single or multiple) contains. It only changes the concentration:

1% nic in 10ml = 10% nic in 1ml.
The amount of nic doesn't change.

Bagazo,

I hope you will be patient with me. I really don't know much chemistry, and I have been reading up on some of these topics to try to understand better. I didn't realize that the term "acid-base extraction" referred to such a specific procedure, for example! And while I know that you can't get more nicotine out, there still is a requirement to concentrate it; The original paper estimated that the extract contained between .1%-1% of nicotine, but the experiments of others here seem to indicate that in general it's probably closer to .1% (perhaps because the starting tobaccos are lower in nicotine). But this is too dilute to use in all but the weakest of e-liquids.

If I understand what they did in the paper, it seems to be relying on something much simpler - the fact that salts won't readily evaporate. So they create a solution where the acids are all salts, and then distill the liquid. Presumably, the acids and solid particulate matter gets left behind, while the nicotine forms an azeotrope at 2.45% (from what I read elsewhere) and therefore gets carried along into the distillate. Then they acidify the solution (turning the alkoloids into salts) and evaporate it, which should leave behind only the alkoloid salts.

It's a simple procedure, and if vinegar and baking soda (or alternatively, sodium carbonate) could be used, doesn't involve anything special. I'm not sure which other alkoloids would be carried along into the distillate, though, at least in a stove-top environment.

 

[Bagazo]

I'm just an internet chemist as well.

We should refrain from highjacking this thread with this topic. I do want to start a thread but can't seem to get a method that is easy, safe and that delivers the goods as far as nic and the other alkaloids. Well at least not anything easier than the method that you linked.

Distillation seems to give you nic only (the other alkaloids don't seem to form an azeotrope with water) and I think Str8vision has a very good point, stocking up might be better than extracting, especially if your going to end up with a nic only juice, unless someone's situation makes it more difficult for them to do so.

 

[Woofer]

I am enjoying the discussion.

 

[Bunnykiller]

didnt think about the cooling process ( freezer) to remove the oils from the PGA extract..... Ive been removing them as they pool on top of the PGA during the heating process.... gonna have to give it a try thanks for the tip

 

[Kingboomer]

Interesting. I'm wondering if this would work for, say, peppermint. Reason I ask is my wife decided a couple of years ago she wanted a peppermint plant in the yard, and now it seems to be taking over lol


-Kingboomer

 

[Str8vision]

The freezing process definitely removes the oils, but judging by the color and texture of the "muck" that coalesces in the bottom half of the extract, I think it also removes waxes, resins and other plant matter. The dark sticky oil that I fully - expected - to see must be a constituent of this muck as further efforts to purify the extract failed to yield even a trace of oil. I skipped intermediate filtration and went from the cold coffee filter straining performed after freezing to the final step which in my case is using 1 micron borosilicate glass filter paper. As reported in an earlier post, the 1 micron filter paper was only slightly discolored even after processing the extract through it several times.

 

[Str8vision]

Interesting. I'm wondering if this would work for, say, peppermint. Reason I ask is my wife decided a couple of years ago she wanted a peppermint plant in the yard, and now it seems to be taking over lol


-Kingboomer

Only one way to find out and it sounds like an interesting experiment. You'd need to remove the essential oil that would be pulled but I see no reason why the flavor couldn't be extracted and condensed.

 

[Str8vision]

I extracted Cornell & Diehl "Oriental Silk No. 414" a few days ago and discovered the heating element in my slow cooker is failing. The hot water bath was at 165F when I started but was below 150F (and still dropping), at the end of the cycle so I'm not sure what the actual temperature was for this extraction. The results were still pretty good but nowhere near as robust as the last four heated ethanol extractions. I'm not familiar with this specific tobacco blend so don't know if it's just a "light" flavor or if the lower processing temperature had something to do with it. I purchased another slow cooker and will run another batch of "Oriental Silk" just to see.

I experimented with the freeze cycle by filtering the extract after only 12 hours sitting at -10F and then re-freezing it for an additional 24 hours. At the end of the second freezing cycle a small amount of gunk had formed in the bottom of the container. To me this indicates 12 hours at -10F wasn't sufficient time for - all - the oils, waxes and other undesirables to coalesce. Next time I will try a 24 hour freeze cycle and see If that is adequate. My goal is to establish the "minimum" amount of time required for the freeze cycle. I know that 36 - 48 hours at -10F is suitable but am hoping a shorter duration proves adequate. Using a centrifuge would certainly speed things up but that I don't have or want.

I've also decided to experiment with performing an extraction at temperatures equal to or slightly above the ethanol's boiling point of 173F. I will attempt 12 hours at 175F, using Cornell & Diehl "Oriental Silk No. 414" thus killing two birds with one stone.

 

[Dan Bean]

This looks great - out of interest, where do you get your ethanol from? Here in UK you need a license to get pure pharma grade ethanol. Would a high proof spirit (vodka) etc work instead for the inital stage?

Dan