AvBaeyer
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Registered: 25-2-2014
Location: CA
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Some Chemistry Based on Turpentine
While searching for information related to the pinenes, I ran across the attached J Chem Ed article which suggests some interesting and challenging
organic chemistry starting from alpha-pinene. Alpha-pinene is the major component of gum turpentine and can be obtained by fractional distillation.
The second attached article describes in the experimental section the isolation and purification of alpha-pinene. It looks like this could be a bit of
challenging fun for those so inclined.
AvB
Attachment: Pinene experiments JChemEd dominguez1963.pdf (2MB)
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Attachment: Interaction of a-Pinene with Carboxylic Acids valkanas1976.pdf (581kB)
This file has been downloaded 394 times
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Fery
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Registered: 27-8-2019
Location: Czechoslovakia
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Hi AvBayer, thank you for sharing interesting ideas. 1 year ago I've bought 5 L canister of alfa pinene very cheaply.
I performed addition of hydrochloride gas to produce bornyl chloride https://www.sciencemadness.org/whisper/viewthread.php?tid=15...
I also performed the D-limonene -> ...nitrosochloride -> ...carvoxime -> carvone, my starting material was D-limonene so the carvone produced
with mint scent (the other carvone isomer has scent like cumin) https://www.sciencemadness.org/whisper/viewthread.php?tid=15...
Reaction with aliphatic acids seems to be promissing... the only thing which worries me is the separation of products (fenchyl, bornyl, terpynyl
compounds) - but certainly even their mixture should have pleasant scent.
And yes, the pinene ring undergoes rearragements very easily...
I have a lot of synthetic camphor so looking forward P2O5 dehydratation (to p-cymene) and dil. HNO3 oxidation (to camphoric acid) described in the
first pdf you attached - I hope during winter there will be some time to perform that.
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