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Nicotine extraction theory

Discussion in 'DIY E-Liquid' started by thoqub, Dec 27, 2009.

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  1. thoqub

    thoqub Senior Member ECF Veteran

    Dec 27, 2009
    Rocky Mount, Va (U.S.)
    DISCLAIMER: I AM NOT A CHEMIST OR ANYTHING! THIS IS SIMPLY A LAYMANS PERSPECTIVE ON A WAY TO EXTRACT THE CHEMICAL! THE CHEMICALS LISTED ARE HIGHLY TOXIC AND SHOULD BE AVOIDED!!!!!!




    Nicotine ,being an alkaloid, should be able to be extracted by using a base chemical, similar to ....... or caffeine. I just finished taking Wikipedian Chemistry 101, so i believe im not totally reliable. Ether, if it is available, can be used to extract alkaloids. As far as i can understand, the raw material is soaked in the ether and the ether is allowed to evaporate completely, usually using a heat lamp. The residual remains are the nicotine and the other alkaloid derivitaves of the material used.
     
  2. Kurt

    Kurt Quantum Vapyre ECF Veteran

    Sep 16, 2009
    Philadelphia
    Plus everything else in tobacco that is soluble in ether, which will be large plant molecules, like chlorophylls, polysaccarides, proteins, LOTS of stuff. Yes, all the alkaloids will be there, but it will not be vapable because of all the other plant junk. The ether solution would then be acidified with something like HCl, which would put make the alkaloids into a water soluble form, then extracted into water. Then the water solution is basified with NaOH and the free-base alkaloids are extracted back into an organic solvent, such as DCM. Then the DCM is evaporated off.

    More to the point, it really does take serious chemical knowledge to do a full alkaloid extraction and have it be usable. Ask DVap. He's the man who did it with his WTA (whole tobacco alkaloid) extract. It is a long and involved process, requiring much specialized glassware, solvents, and reagents, to get it right. Even if your ether extraction was good enough, how would you get rid of the ether entirely? Even a minute quantity, which will linger in an extract without proper removal methods, will send you to Pluto if you vape it. It was used for centuries as a general anesthetic.

    You mention ........ The ether extraction is only the first step, with subsequent acid and base extractions to eventually give ....... hydrocloride salt, not free-base ........ Free-base coke (crack) is made by basifying coke-HCl with baking powder, making a brittle solid material that is cracked into chucks (rock).

    Alkaloid extraction if you have had a college course in organic chemistry is not difficult. You are on the right track with the ether extraction, but only about 20% of the way. DVap knows exactly what he is doing, since he is a professional chemist, and it is still a pain to do, and there is a large waste-material issue to be dealt with, even under the most careful and controlled conditions. And how will you know what you have in the end, as in strengths and contents?

    While I don't recommend Wiki for organic chemistry procedures for a novice, here is a little about what I am referring to:

    Acid-base extraction - Wikipedia, the free encyclopedia

    The thread in ECF that addresses this total alkaloid issue is:

    http://www.e-cigarette-forum.com/forum/nicotine/44958-so-we-getting-we-not-nicotine.html

    I commend your initiative to look into this, but I'm afraid this really is not something a non-chemist should take on. Nicotine and its associated alkaloids are not something you should be extracting while you learn how to do it properly. If you do get all the chemicals and glassware, and the knowledge, to do this safely, I would recommend extracting harmless caffeine from tea first. If you can do this, and prove that you have pure caffeine in the end (not by ingesting!!), then you might be good enough to try it with deadly nic.

    Let's put it this way. I'm an organic chemist with many years of post-college experience, both research and teaching college organic. I will not do this extraction. I could but I won't, because of the dangers...and I'm very experienced with hazardous chemicals. I would need a lot of practice with similar alkaloid-extractions which are harmless compounds before I would trust myself to not kill myself extracting nic. If you have no training in alkaloid extractions do not do this!!
     
  3. thoqub

    thoqub Senior Member ECF Veteran

    Dec 27, 2009
    Rocky Mount, Va (U.S.)
    I'm definately not going to try it! I thank you for your commentary. It was just a theory and you just disproved it for me. I plan on starting my college education very soon and I'm planning on becoming a chemist.

    Also, would it be possible to extract the alkaloid with ammonia? just a thought

    true freebase ....... is made from ether extraction, crack ....... is not totally pure but more like 95% and lower because ....... HCL is usually cut to atleast 75% before coming to the states. it is only put into the rock so that it can be smoked whereas, I belive, free base is almost totally pure.
     
  4. Kurt

    Kurt Quantum Vapyre ECF Veteran

    Sep 16, 2009
    Philadelphia
    thoqub, that's good news that you want to become a chemist! :D Your theory was actually quite correct! The problem was the ether will get out all sorts of stuff you don't want, in addition to the alkaloids. Its clear you will absolutely LOVE organic chemistry. Indeed it was the class that made me want to declare chemistry as a major.

    If by ammonia, you mean aqueous ammonia that you would buy at the grocery store, no, it will not extract alkaloids. They are amines and as free-bases will not be very soluble in water or basic solutions. They will be soluble into acidic solutions, however, since they will be protonated to form a water-soluble salt, like the hydrochloride salt is it is aq. HCl. Extractions are a sequential process meant to gradually separate the MANY compounds that the initial ether or DCM extraction gets, by water and organic solvent solubility differences made by turning the alkaloids into free-bases or salts. In order to understand the chemistry, you first have to understand organic-amine acid-base chemistry and the water-solubility rules for each form. If an amine is written as R-NH2, where R is some organic part, this is the free-base, and it is soluble in ether. Ether solution is shaken with HCl(aq). The free-base forms R-NH3+ Cl-, the hydrochloride salt of the free-base. This is soluble in water and will leave the ether layer and enter the HCl(aq) layer. Then the HCl layer is basified with aq. NaOH (or ammonia) until it is pH basic, and fresh ether is shaken with it. The reaction is:

    R-NH3+ Cl- + OH- ----> R-NH2 + H2O + Cl- (Na+ is a spectator ion).

    This forms the free-base, which is ether-soluble and goes into that layer. The trick is to do these steps in a particular way to selectively remove the other junk, and have the final ether layer containing only alkaloid free-base molecules and no junk. Thus this is an acid-base extraction. VERY common, and the normal way to do these things, but requires a fair amount of skills, knowledge, chemicals, and special glassware, like sep funnels. Analysis of the final extract can be done with GC-MS, NMR, or IR spectroscopy. GC-MS is best, but not widely available.

    BTW, it is my understanding that crack IS ....... free-base. Ether will get a lot of plant material from the coca leaf, which are then separated in an acid-base extraction method, yes, finally into the ether layer. ....... in sniffing form as a white powder is the HCl salt, and has an extremely high boiling point, since it is a salt. The free-base crack has a very low bp, since it is the free-base and not ionic, and so can be smoked (actually vaporized in a glass pipe, not combusted generally). Crack is pure, or close to it, but sniffing coke being a powder can be cut with any white powder.

    And BTW, I have zero interaction with ....... in any form. Never did it. Saw many friends ruined because of it.

    Since you want to be a chemist one day, I would suggest to you again to figure out all the steps needed to extract caffeine in tea away from all the other plant materials. We did it in the organic lab I teach. Procedures can probably be found online. It will be an excellent journey for you to learn the ins and outs of extractions. Who knows, maybe one day you will become a natural product chemist, who finds some alkaloid that can cure cancer or another illness. Caffeine is the typical entry-level alkaloid to learn on.

    Have fun! :)
     
  5. thoqub

    thoqub Senior Member ECF Veteran

    Dec 27, 2009
    Rocky Mount, Va (U.S.)
    Thank you so much for your posts! The only reason i haven't started classes yet is because I dont have a fundage and I am afraid to get a loan (not like I would in the state of the economy) and with no job or help from the folks I've got to go at this alone. I actually found a college thats tuition, room and board, are 7,500 a year! It is accredited from what I have heard. I had good grades in school so I am not sure of any scholarships and whether or not i am eligable.

    http://www.pcci.edu/


    BTW


    Where did you go to college?
     
  6. Kurt

    Kurt Quantum Vapyre ECF Veteran

    Sep 16, 2009
    Philadelphia
    Washington University, St. Louis. I took a look at the college you have the link for. Looks like the chemistry major is a standard curriculum. I recommend you take a visit if you are very interested in going there, and talk to chemistry majors and see if they feel they are getting a good education, with opportunities to present undergraduate posters or talks at conferences, and most important, if there is opportunity to do undergrad research in your junior and senior years, preferably with grad students. I really started getting into the good stuff when I was able to learn with grad students. A graduate program in chemistry will always make the undergraduate experience far better and more rigorous. You should also try to find summer chemistry internships for the summers after your freshman and sophomore years. I was a QC technician with Eli Lilly during those times. Chemistry skills take years to develop and hands-on experience is invaluable.

    Chemistry is a great and wonderful field, and its so huge that there are always opportunities in both academia and industry. Chemistry definitely pays the bills and for me it is never boring, always exciting, always fun and challenging.
     
  7. thoqub

    thoqub Senior Member ECF Veteran

    Dec 27, 2009
    Rocky Mount, Va (U.S.)
    Thank you very much for the conversation Kurt, feel free to PM me anything else you would like to talk about.
     
  8. DVap

    DVap Nicotiana Alchemia Verified Member ECF Veteran

    Aug 26, 2009
    Retired
    Agree with Kurt's observations.

    I won't touch ether if I can help it... explosive peroxide formation along with a frighteningly low auto-ignition temperature (170°C).

    If you're doing anything with caffeine (for example), skip the ether. The extraction and rough purification is only part of the trick. Recrystallization is an art in itself via solvent selection to dissolve the material when hot but precipitate it when cold. The technique typically involves getting the precipitate and vacuuming away the solvent via a filter paper disk in a büchner funnel/büchner flask with a water aspirator, then rinsing the precipitate with more cold solvent (sometimes multiple solvents in which the filtered product is insoluble).
     
  9. thoqub

    thoqub Senior Member ECF Veteran

    Dec 27, 2009
    Rocky Mount, Va (U.S.)
    Thank you very much. Once again its just a theory I had. Didnt know there were such qualified members of the forum. I will likely purchase the equipment for the caffeine extraction and also have it tested to make sure it is pure. One question, would it be possible to add caffeine to an eliquid? I am not willing to try it I would like to know, however. thank you in advance
     
  10. DVap

    DVap Nicotiana Alchemia Verified Member ECF Veteran

    Aug 26, 2009
    Retired
    I think it's been discussed, use the search feature for it. Not finding it an interesting proposition, I gave the topic a miss.
     
  11. Kurt

    Kurt Quantum Vapyre ECF Veteran

    Sep 16, 2009
    Philadelphia
    No problem! Happy to help as I can.

    And, DVap, I totally forgot about the peroxide issue with ethers! That and the flash point make it not a great solvent for these things. Dichloromethane (DCM) is the goto for this.

    As for vaping caffeine, I wouldn't spend much time on that one. Caffeine sublimes, which means it will redeposit all over the atty as white powder. Besides caffeine is actually more effective by drinking it, due to the mode of stimulation effect, which is partially to block cyclic-AMP forcing the body to make use up ATP energy molecules. Pure caffeine in the mucus membranes is not pleasant anyway, pretty harsh and may cause problems. You can check to see if others have tried this, but I prefer my caffeine as strong hot tea. Fact: not everything is better ingested as vapor. I read here of people considering dissolving their antidepressants in VG to vape them. NOT SMART!! Most of those compounds are actually designed to be ingested through the intestine, and their form in the pills take into account pH of the environment. Most are NOT free-base form and will not vaporize easily anyway, and there is no info on what they would do in the lungs anyway. Stick to vaping nic only at least for now.

    Also, you may find that the glassware needed for caffeine extraction, if you actually want to do it, and not just make it a research "assignment", may be rather expensive for you. recrystalization, as DVap says, is an art unto itself, but the final step in caffeine purification is generally a sublimation onto a "cold finger". I was more interested in you learning about the theory behind acid-base extractions, and it will help you understand many alkaloid extraction processes. Good luck, and have fun!
     
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