Limonene Chemistry

Quote: Originally posted by GreenJames

I recently bought a bag of oranges for food, however the big reason is because I want to extract limonene from the peels. It will take me a while to eat a substantial enough amount, so in that time I am trying to look for something interesting I can do with the limonene besides just giving my glassware a nice fragrance. Does anyone have any ideas?

Orange oil is quite cheap and you can buy it in 1 liter cans and even bigger... I have 2 l of technical grade (orange oil, 95% limonene) and 1 l of pure (+) limonene (Sigma Aldrich), but still not enough time to perform all wanted experiments (already collected just all necessary info and all required reagents). But for small scale chemistry few ml obtaining from orange peel is enough (using a grater before eating the orange is the best method to prepare the peel for a steam distillation)

Here some of my ideas what to do:
Limonene -> carvone
Limonene -> alfa terpineol

for the step 2 of the carvone (elimination of HCl from limonene nitrosochloride -> carvoxime) you can probably use just urea (not yet tested)

here famous limonene.pdf by Nicodem:
http://www.sciencemadness.org/scipics/Nicodem/Limonene.pdf
a lot of pdf attached



Attachment: (+)-alfa-terpineol_from_(+)-limonene_baptistella2009.pdf (185kB)
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Attachment: (+)-Limonene to (-)-Carvone.pdf (2.5MB)
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Attachment: bordenca1951.pdf (386kB)
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Attachment: royals1951.pdf (293kB)
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Attachment: US3293301.pdf (377kB)
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[Edited on 29-2-2020 by Fery]