Sciencemadness Discussion Board - Dry distillation of Tabacco

Dry distillation of Tabacco

Chemistry Alchemist - 24-11-2011 at 06:18

Ok so i know cigarettes are bad and i personally HATE them but all websites that say to stop smoking say that there are thousands of chemicals in the cigarette... so this is a science forum so science with cigarettes? Now the most common chemicals i have found so far on sites are these;

Ammonia: Household cleaner
Angelica root extract: Known to cause cancer in animals
Arsenic: Used in rat poisons
Benzene: Used in making dyes, synthetic rubber
Butane: Gas; used in lighter fluid
Carbon monoxide: Poisonous gas
Cadmium: Used in batteries
Cyanide: Deadly poison
DDT: A banned insecticide
Ethyl Furoate: Causes liver damage in animals
Lead: Poisonous in high doses
Formaldehyde: Used to preserve dead specimens
Methoprene: Insecticide
Megastigmatrienone: Chemical naturally found in grapefruit juice
Maltitol: Sweetener for diabetics
Napthalene: Ingredient in mothballs
Methyl isocyanate: Its accidental release killed 2000 people in Bhopal, India in 1984
Polonium: Cancer-causing radioactive element

Most common out of these would be benzene, Ammonia, Acetone, Nicotine, Formaldehyde and Naphthalene...

Most of this would be useless for home chemistry and a lot would be as salts which for the procedure suggested below wont be good for solids but for the liquids it will be great... Now the procedure i thought of is Distillation? the products are normally released in the smoke as vapors and others will stay in the reaction flask... The inorganic compounds most likely wouldn't come over, while most of the organic's will unless they are a solid... say we had a few packets of the strongest packet of smokes and the worst glassware (worst as on old - the smell may wreck the glassware a bit)... what chemicals do u think would come over when the tobacco is heated up and smoke is produced? (the final distill would have to be re distilled to separate the chemicals if there is enough...) after the smoke has stopped, are there any useful chemicals among the chard tobacco?

Now I'm not sure where this post belongs but you can move it if it needs to be. I'm also most likely not even going to preform this due to the toxicity of the chemicals and the reactions as well as most likely the high temperatures needed, I'm only asking theoretically what would happen if this was done...

ScienceSquirrel - 24-11-2011 at 06:30

The most common chemical isolated from tobacco is nicotine.
It is pretty toxic as the free base and it's salts and it is readily absorbed through the skin.
It was used as an insecticide but it's use has been discontinued due to it's toxicity and general unpleasantness.
http://en.wikipedia.org/wiki/Nicotine

Chemistry Alchemist - 24-11-2011 at 06:44

in a single packet (say it was a 50 pack) how much could be recovered? could any other chemical be isolated or are they so minute that not even a ml comes over?

ScienceSquirrel - 24-11-2011 at 07:05

You would not distill the tobacco but digest it with something like dilute hydrochloric acid. Filter off the acid solution from the leaf material, boil with charcoal, filter through celite. concentrate and then add sodium hydroxide. Extract with ether, concentrate and distill.
Really you would want to start with about half a kg of tobacco or so which would be about EUR150 worth where I live if you bought it and this would yield about 3 - 15g.
It is not illegal to grow tobacco here but it is illegal to process or prepare it without paying duty.
All the things that you mention are present in tobacco smoke in vanishingly small quantities and can sometimes be made pure by other means eg carbon monoxide can be made by adding formic acid to concentrated sulphuric acid.

Chemistry Alchemist - 24-11-2011 at 07:12

true, i kinda new that most of those chemicals would be in tiny quantities (0.001g) or smaller for some if they say there are 4000 chemicals in a cigarette... so if one to way 4 grams then the proportion of the amounts would be tiny... and the cost to get a good yeild of stuff would be heaps aswell as the mess and all

ScienceSquirrel - 24-11-2011 at 07:22

One interesting property of cigarette ash is that if you rub some on the corner of a sugar cube it can easily be set on fire with a cigarette lighter.
Without the ash it is almost impossible to light the cube. This was an old bar trick when everybody smoked, drank coffee, wine, beer, pastis, etc and ate in the same bar room with a large number of dogs on the floor and on one memorable occasion a goat. One place had several cats draped over the bar as well as a few checking out the kitchen. Through the screen you could see them sitting on the counter where the chicken, etc was being prepared for the plat de jour.

Neil - 24-11-2011 at 16:56

tobacco is curiously designed to produce tar filled smoke to carry the nicotine. nicotine is too fragile to be vaporised and has to hitch a ride in the vapours produced by the pyrolysis of the tobacco leaves.

So really, you are just looking at pyrolysis of plant leaves. Grab fistfuls of dry plant matter and char them till they stop fuming, collect and condense the off gasses and you'll have more chemicals then you could quantify in several life times - it doesn't have to be tobacco, they've just spent the most life times trying to quantify everything in tobacco smoke.

Mining cigarette smoke would be like trying to extract the bucky balls from diesel soot...

However, there are lots of intentional useful things you can get by producing wood gas, for example methanol.

Mildronate - 27-11-2011 at 08:25

Its propoganda for nonsmoking, of course there is many chemicals like in other plants.

turd - 27-11-2011 at 11:16

Quote: Originally posted by ScienceSquirrel

You would not distill the tobacco but digest it with something like dilute hydrochloric acid.

Actually the classic method is to basify, steam distill and isolate via the oxalate: https://www.sciencemadness.org/whisper/viewthread.php?tid=34...

ScienceSquirrel - 27-11-2011 at 14:17

I was suggesting it as a possible general approach. Methods like it are widely used to get alkaloids from plant material.

Charles Boyle - 16-12-2011 at 20:09

Quote: Originally posted by Mildronate

Its propoganda for nonsmoking, of course there is many chemicals like in other plants.

Name one other plant material considered by governments worldwide to be "Safe for human consumption" that is known to contain: arsenic, ammonium, benzyne, cadmium, cyanide, DDT, lead, formaldehyde, and polonium.

As for the topic of the thread, good luck to you sir, I think Neil's analogy for mining cigarette smoke is spot on.

unionised - 17-12-2011 at 07:47

Quote: Originally posted by Charles Boyle

Quote: Originally posted by Mildronate

Its propoganda for nonsmoking, of course there is many chemicals like in other plants.

Any food will contain those materials (give or take your spelling errors). It's a matter of how hard you look for them.

MagicJigPipe - 17-12-2011 at 20:45

Unionised is correct. Charles Boyle has fallen for the propaganda hook, line and sinker. Of course smoking cigarettes is bad for you. But only mildly more so than regularly inhaling any sort of smoke produced from pyrolysis of organic materials (especially plants). With some exceptions, whatever is in the soil will be in the plant. OF COURSE those compounds and elements you mention are in other plants.

How the hell do you suspect that tobacco is so fundamentally different from other plants? How would that happen? Human modification? Sure. But to what extent? Not much (especially when it comes to the heavy and radioactive metals).

Reexamine the situation when your head has leveled out a bit and you've acquired a taste for rational, rather than emotional, thought.

[Edited on 12-18-2011 by MagicJigPipe]

Neil - 18-12-2011 at 15:05

Some plants do concentrate heavy metals (Eg. alfalfa, hemp, iris) so they will contain more heavy metals then other plants when grown in the same soil, but I have yet to see a paper documenting such behavior in tobacco.

Cigaret tobacco is designed to produce certain amounts of tar at certain air flows (there is an equation for this is you search for it) , but beyond that it's not much different then tomatoes or potatoes.

MagicJigPipe - 18-12-2011 at 16:17

Are you trying to contradict what I said? I think that if you will read it again you will see that I never said anything contrary to your statement(s).

If not, disregard this.

Neil - 19-12-2011 at 12:10

Nope, no argument. I was trying to add to what you had said

Also apparently tobacco does concentrate heavy metals (I amened my previous statement about it not)
http://www.agr.uth.gr/labs/soil/pdfs/pdf14.pdf

But then;
http://www.pjoes.com/pdf/12.6/779-784.pdf
hemp does it to a far greater degree

Apparently tomato does not accumulate cadmium
http://www.sciencedirect.com/science/article/pii/S0304423807...

But potatoes do;
http://www.ncbi.nlm.nih.gov/pubmed/7219518

and of course a write up about gold from plants...

http://economicgeology.org/content/74/4/902.abstract