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Author: Subject: Cinnamic acid extraction from shea butter
Antiswat
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shocked.gif posted on 10-9-2021 at 06:13
Cinnamic acid extraction from shea butter


having come across a truckload of shea kernels i decided to try to extract the shea butter myself, looking into the composition of shea butter one chemical stood out: cinnamic acid, as high as 6%, but really less than that. however shea butter isnt super expensive if you buy like a kg. from the kernels its roughly 50% "shea butter"
1kg shea butter is about 13 euros, lets call that maybe 60g of cinnamic acid
now cinnamic acid is interesting as it can be turned into benzaldehyde by permanganate in low concentration HClO4

https://realizebeauty.wordpress.com/2016/07/13/the-chemistry...

im just lost as for how to seperate out the different components? shea butter is sometimes purified by shortpath distillation, cinnamic acid iirc boils at about 300*C- fractional distillation??

as for the shea butter extraction process im not sure yet, its surprisingly difficult, grind it too fine and you just get a mud when trying to seperate it in hot water, but i have gathered more than 100kg so i potentially have 50kg of shea butter at hand, might have to shoot for a diy oil press with a bit of preheating of the shea kernels




~25 drops = 1mL @dH2O viscocity - STP
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https://en.wikipedia.org/wiki/Solubility_table
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Amos
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[*] posted on 11-9-2021 at 04:57


Well the cinnamic acid exists as heavy, waxy esters, so there's no way you're getting it out without saponification with base. But then it would exist in a mix with lots of other free fatty acids, and separating those might prove very hard.
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[*] posted on 11-9-2021 at 08:11


You might be able to esterify everything with methanol, and then steam distil out the methyl cinnamate.
This would be a better route to of biodiesel than to cinnamic acid.
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[*] posted on 11-9-2021 at 08:18


and methyl cinnamate has a nice scent, but for me only very weak, I have this compound as a commercial product
http://www.thegoodscentscompany.com/data/rw1417571.html




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DraconicAcid
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[*] posted on 11-9-2021 at 09:23


L made some methyl cinnamate a few years ago. I found that if I wanted to smell it, I had to put a little bit into a beaker of hot water. That would volatilize it enough that I could smell the strawberries.



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Antiswat
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[*] posted on 12-9-2021 at 02:00


so i could try fractionally distilling it out
then reacting each fraction with sodium hydroxide- or doing that before distilling on it
either way esterification with ethanol or methanol and then maybe pull that with a solvent or distill it again?


Methyl Cinnamate XlogP3 2.6
Ethyl Cinnamate XLogP3 3



XlogP3 of solvents relatively close
1.5 - DCM | Benzaldehyde | Phenol, hydroxybenzene
1.6 - Amyl alcohol, Pentanol
1.8 - Propane | Butyl acetate | Amyl Nitrite
1.9 - Hexanoic acid
2.0 - Benzyl Acetate | Hexanol
2.1 - Benzene | Methyl benzoate
2.3 - Benzyl chloride | Methyl salicylate | Chloroform
2.5 - Toluene | Xylene | Heptanoic acid
2.6 - Chloropentane | Ethyl benzoate
2.9 - Butane | Styrene | Glyceryl trimethacrylate
3.0 - Ethyl salicylate
3.2 - EthylHexyl Acetate | Benzyl salicylate
3.3 - Diphenyl carbonate
3.4 - Cyclohexane
3.6 - Chlorohexane
3.7 - Limonene

Butane could work to pull out both, maybe.

reacting methyl cinnamate would grant sodium cinnamate with methyl alcohol, sodium cinnamate has a BP of 265*C
Solubility: Sodium cinnamate (CAS NO . 538-42-1) is soluble in hot water, slightly soluble in alcohol.

Methyl cinnamate: Solubility insoluble in water, boiling point 261.899 °C
Cinnamic acid: It is very slightly soluble in water (25 ℃: 0.1; 98 ℃: 0.588), soluble in ethanol (25 ℃: 23), chloroform (15 ℃: 5.9), easily soluble in benzene, ether, acetone, acetic acid (concentration?) and carbon disulfide.

at some point, working in bulk with fractions it should be possible to pull out cinnamic acid.

so to cap off: NaOH shea butter, sodium cinnamate soluble in hot water, ppt out cinnamic acid
or
MeOH shea butter, fractionally distill, NaOH the MeCinnamate, seperate with hot water or solvent, butane?- acidify to acquire cinnamic acid




~25 drops = 1mL @dH2O viscocity - STP
Truth is ever growing - but without context theres barely any such.

https://en.wikipedia.org/wiki/Solubility_table
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