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Author: Subject: Toluene from Natural Sources
Hawkguy
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[*] posted on 9-12-2015 at 20:20
Toluene from Natural Sources


At the moment, I've been working on various projects that generally involve natural sources. These projects include the extraction of Oxalic acid from Rhubarb or Skunk cabbage, Salicylic Acid from Willow bark, Iodine from seaweed, Sulfur from pyrite deposits (took me awhile to find), Methanol from wood, Ethanol from sugar, Nitrate from compost, well, you get the idea. One thing I recently found out about was Toluene occuring in natural oils, from pine trees. Has anybody tried this extraction? My plan was to just distill in a shitty apparatus, and dry with Calcium Oxide. Anyone got any advice? I checked stuff out online already, and the only big issues I think I'll run into is low yields and questionable purity.
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[*] posted on 9-12-2015 at 20:47


Look up diistilation of turpintune from pine sap
Also distillation of rosin




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[*] posted on 9-12-2015 at 20:50


Quote: Originally posted by Dark Alchemist  
Look up diistilation of turpintune from pine sap
Also distillation of rosin

I think the toluene is in the pine needle essential oil, not the resin.
Otherwise, turpentine would be full of it.

Actually, other than this mention in the Wikipedia article:
Quote:
The compound was first isolated in 1837 through a distillation of pine oil by a Polish chemist named Filip Walter, who named it rétinnaphte.

...I can't find anything to suggest that pine trees of the sort that grow in Canada produce toluene in any meaningful amount.
@Hawkguy: Where did you read that?

I did find a couple of references to the production of toluene from turpentine, using red-hot iron or aluminum trichloride catalysts, the latter of which sounds a lot like the laboratory preparation given in the Wikipedia article.

[Edited on 10-12-2015 by MolecularWorld]




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[*] posted on 9-12-2015 at 20:52


My mistake



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[*] posted on 9-12-2015 at 21:41


Nice work by the way I have been interested in natural sources of chems for a while now.
I myself have successfully made both KNO3 and NaNO3 from urine inriched soil.




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[*] posted on 9-12-2015 at 21:42


Nice work by the way I have been interested in natural sources of chems for a while now.
I myself have successfully made both KNO3 and NaNO3 from urine inriched soil.




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[*] posted on 9-12-2015 at 21:52


Quote: Originally posted by Dark Alchemist  
Nice work by the way I have been interested in natural sources of chems for a while now.
I myself have successfully made both KNO3 and NaNO3 from urine inriched soil.


How long did it take you? Assuming you started off with raw plant matter that is... My last pile of compost took 6months or so, and the yields (Sodium Nitrate) were pretty minimal. I also had to deal with all this black shit that made the extraction difficult...
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[*] posted on 9-12-2015 at 21:55


Quote: Originally posted by MolecularWorld  
Quote: Originally posted by Dark Alchemist  
Look up diistilation of turpintune from pine sap
Also distillation of rosin

I think the toluene is in the pine needle essential oil, not the resin.
Otherwise, turpentine would be full of it.

Actually, other than this mention in the Wikipedia article:
Quote:
The compound was first isolated in 1837 through a distillation of pine oil by a Polish chemist named Filip Walter, who named it rétinnaphte.

...I can't find anything to suggest that pine trees of the sort that grow in Canada produce toluene in any meaningful amount.
@Hawkguy: Where did you read that?

I did find a couple of references to the production of toluene from turpentine, using red-hot iron or aluminum trichloride catalysts, the latter of which sounds a lot like the laboratory preparation given in the Wikipedia article.

[Edited on 10-12-2015 by MolecularWorld]


I'm not finding much good stuff online on Toluene from Turpentine, it looks like a lot is produced from crude oil. I found the Toluene comment somewhere I can't locate now. Not a huge loss, as the article was pretty badly done.
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[*] posted on 9-12-2015 at 21:57


I tried distilling oils and resins from most plants that grow near me in large amounts, but most of the stuff I get is Phenol related stuff, Methanol, water, and various oils that I cannot identify.

I put the pieces of wood/bark/whatever in a small can from paint or whatever, (after a glass flask broke because I was stupid), I poke a hole, and the stuff condenses in a tube, and if it doesn't catch on fire, I can collect it.

[Edited on 10-12-2015 by Hawkguy]
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[*] posted on 9-12-2015 at 22:01


About 9 months for the first one when I was finishing of the process however I used the wrong kind of wood ash so got mostly sodium nitrate
Which turned out a slightly brown color until 3rd recrystallisation.

Second one took a year and gave much higher yeild about 400 grams once purified and dried in the oven.

I was so proud of that black powder
If you were wondering it was carried out in black sack filled with straw and chicken manure as well as some ash from an oak.




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[*] posted on 9-12-2015 at 22:08


Opps 400 grams my ass I ment 40 grams.
On the note of nitrates how do I naturally convert it to ammonium nitrate?

[Edited on 10-12-2015 by Dark Alchemist]




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[*] posted on 9-12-2015 at 22:41


Quote: Originally posted by Dark Alchemist  
On the note of nitrates how do I naturally convert it to ammonium nitrate?


I don't know what you mean by "naturally", but here's How to Make Ammonium Nitrate from Sodium Nitrate.




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[*] posted on 9-12-2015 at 22:50


Thank you for you reply.
When I said naturally I meant from naturally sourced materials no shop bought or mass produced chemicals

Nonetheless the video was informative and helpful paticulary with the bans on An cold packs in my area.

[Edited on 10-12-2015 by Dark Alchemist]




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[*] posted on 9-12-2015 at 22:51


As far as toluene itself goes, you could make uvitic acid by the self-condensation of pyruvic acid in the presence of strong base and then decarboxylate it. But that is a fairly insane approach.
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[*] posted on 10-12-2015 at 20:10


Quote: Originally posted by UC235  
As far as toluene itself goes, you could make uvitic acid by the self-condensation of pyruvic acid in the presence of strong base and then decarboxylate it. But that is a fairly insane approach.


That is very insane yes.
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[*] posted on 10-12-2015 at 20:55


While it may be hideously impractical, I did once manage to make toluene from cinnamic acid via fermentation with yeast under (high) osmotic stress. It was quite a surprise.

O3




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[*] posted on 11-12-2015 at 04:58


Destructive distillation of coal- Some toluene comes off along with the heavy crud/coal tar.

You also get a little bit of toluene and xylene along with the methanol from destructive distillation of wood.




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