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Author: Subject: Limonene Chemistry
GreenJames
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[*] posted on 28-2-2020 at 17:41
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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[*] posted on 28-2-2020 at 18:16


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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[*] posted on 29-2-2020 at 00:07


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

244.png - 153kB 245.png - 140kB 246.png - 84kB

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]




If there is a heaven, it seems not to be materially based. Does chemistry exist there and if yes, how does it look like? Are there good souls well supplied with laboratory equipment, glass, chemicals and information?
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Amos
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[*] posted on 29-2-2020 at 06:32


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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[*] posted on 1-3-2020 at 05:38


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.

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Fery
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[*] posted on 1-3-2020 at 07:49


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, ...)




If there is a heaven, it seems not to be materially based. Does chemistry exist there and if yes, how does it look like? Are there good souls well supplied with laboratory equipment, glass, chemicals and information?
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GreenJames
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[*] posted on 1-3-2020 at 09:00


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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