GreenJames
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Limonene Chemistry
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?
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Deathunter88
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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? |
You're never gonna get enough to do much with it, if you need it as a solvent just buy it on Amazon.
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Fery
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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)
This file has been downloaded 322 times
Attachment: (+)-Limonene to (-)-Carvone.pdf (2.5MB)
This file has been downloaded 1075 times
Attachment: bordenca1951.pdf (386kB)
This file has been downloaded 303 times
Attachment: royals1951.pdf (293kB)
This file has been downloaded 328 times
Attachment: US3293301.pdf (377kB)
This file has been downloaded 292 times
[Edited on 29-2-2020 by Fery]
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Amos
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Sometimes it's more fun to do things yourself, and it's not necessarily true that the OP won't get enough to play around with. The average orange
contains over a gram of limonene, so with a nice large flask and well-divided peels, you could definitely prepare a vialful.
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wg48temp9
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In the synthesis of carvone from lemonene what is the function of the DMF ?
I assume its to make the nitroso chloride more soluble. Is there a more OTC substitute? Ultimately I want to synthesis carvacrol from the carvone.
I am wg48 but not on my usual pc hence the temp handle.
Thank goodness for Fleming and the fungi.
Old codger' lives matters, wear a mask and help save them.
Be aware of demagoguery, keep your frontal lobes fully engaged.
I don't know who invented mRNA vaccines but they should get a fancy medal and I hope they made a shed load of money from it.
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Fery
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wg48temp9 removing HCl (dehydrochlorination)
it could be done with urea also (Bordenca1951.pdf)
I plan to perform the synthesis but very likely the next winter as now this winter is going to end a lot of works will begin (garden, forest, house,
...)
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GreenJames
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This actually looks like a pretty great and accessible synth, I think I'll give it a shot with urea. I'll post my results once I get around to it.
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