Sciencemadness Discussion Board
Not logged in [Login - Register]
Go To Bottom

Printable Version  
Author: Subject: Phenylacetone from decarboxylation of cinnamaldehyde?
Kratom3million
Harmless
*




Posts: 13
Registered: 3-10-2017
Member Is Offline

Mood: No Mood

[*] posted on 4-10-2017 at 00:20
Phenylacetone from decarboxylation of cinnamaldehyde?


Possible Synthesis Of Phenylacetone from Cinnamaldehyde (Cinnamaldehyde > Allylbenzene > Phenylacetone)

A possible synthesis of Phenylacetone from Cinnamaldehyde. My theory is that the decarboxylation of cinnamaldehyde will result with allylbenzene and then the allylbenzene can be furthered to phenylacetone using various methods; such as esterification, ketone addition, and acetone addition (acetonization?). We are going to say that esterification would be the simplest method.
So, this cinnamaldehyde is boiled at between 300-350F for 15 to 20 minutes, which will do a theoretical decarboxylation- no solvent is needed since it is already a liquid, is the theory. This would then theoretically yield allylbenzene of around 90% purity (if starting from cinnamon oil, since cinnamon essential oil is said to contain around 90% cinnamaldehyde). Cinnamaldehyde's boiling point is around 478F according to wikipedia.
The next and final step- ester addition (esterification) to/of the allylbenzene. This is done by mixing the theoretical allylbenzene with a molar equal amount of ethyl acetate.

Sources:

1. https://en.wikipedia.org/wiki/Cinnamaldehyde
2. https://en.wikipedia.org/wiki/Decarboxylation
3. https://en.wikipedia.org/wiki/Phenylpropene


Need criticisms/opinions please!!!!!

4. https://en.wikipedia.org/wiki/Ester#Preparation
5. https://en.wikipedia.org/wiki/Ethyl_acetate
View user's profile View All Posts By User
Melgar
International Hazard
*****




Posts: 1848
Registered: 23-2-2010
Location: NYC
Member Is Offline

Mood: Aromatic

[*] posted on 4-10-2017 at 03:42


You posted poorly-researched questions in the wrong folder, and the second a mod sees this thread it's going to get canned anyway. Anyway, you need to drop the idea of using cinnamaldehyde, since there are much easier, cheaper precursors out there. Styrene, for example, can be purchased at boat supply stores as "resin thinner". Or better yet, you can get it by destructively distilling polystyrene! Doesn't that sound fun?



The first step in the process of learning something is admitting that you don't know it already.
View user's profile View All Posts By User
JJay
International Hazard
*****




Posts: 2924
Registered: 15-10-2015
Location: Western Hemisphere
Member Is Online

Mood: :cool:

[*] posted on 4-10-2017 at 04:35


The obvious route to phenylacetone from allylbenene would be isomerization to alpha-methylstyrene followed by Wacker oxidation. But it would require a palladium catalyst.

I somehow doubt you can decarboxylate cinnemaldehyde so easily....

Discussion of this sort of thing usually ends up in Detritus unless there is some actual yield or photos of the product.




This is my YouTube channel: Extreme Red Cabbage. I don't have much posted, but I try to do nice writeups once in a while.
View user's profile View All Posts By User
Texium (zts16)
Super Moderator
*******




Posts: 2859
Registered: 11-1-2014
Location: San Marcos, TX
Member Is Offline

Mood: Organiking

[*] posted on 4-10-2017 at 04:37


Discussion of this sort always ends up in Detritus, and people who keep starting new threads that are identical despite that tend to get banned...



View user's profile Visit user's homepage View All Posts By User
Texium (zts16)
Super Moderator
Thread Moved
4-10-2017 at 04:37

  Go To Top