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Author: Subject: Extraction of cinnamaldehyde from cinnamon
Barney
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[*] posted on 17-4-2024 at 02:34
Extraction of cinnamaldehyde from cinnamon


I wanted a simple but at least somewhat interesting procedure I could use to test out my new glassware, and I settled on extracting cinnamaldehyde from cinnamon by steam distillation.



Steam distillation
A hole was drilled in the lid of a stockpot large enough to fit a still head. The stockpot was sealed by the use of a PTFE gasket made from plumbers tape and cardboard as described on the home distiller forum (1). Foldback clips were used to hold everything together.


1kg of cheap cinnamon powder was added to the stockpot along with roughly 5L of water. A small amount of dish soap was also added in an attempt to prevent foaming (this idea came from a video by Amateur Chemistry (2)). A simple distillation was then set up and heating turned on. A cloudy distillate soon began to come over. It was originally planned to collect distillate until it was clear, however after a few hours the sun was beginning to set and this had not happened, so the distillation was ended prematurely. A little over a litre of distillate ended up being collected.

Solvent extraction
The cloudy distillate was added to a separatory funnel and extracted twice with a small amount of ethyl acetate. This left the aqueous layer clear. The ethyl acetate layer containing the product was dried over calcium chloride overnight. The ethyl acetate was then distilled off in a water bath under vacuum. This gave 4.36g of yellow oil, which is crude cinnamaldehyde.

The yield corresponds to about 0.4% of the mass of starting material, which is very low, but this isn't at all surprising given that the distillation was ended so early.

I had originally planned to purify the cinnamaldehyde by converting it to its bisulfite adduct, but this process took longer than I'd expected and I couldn't really be bothered. Regardless this should be pure enough for most purposes.

The cinnamaldehyde had a very strong and somewhat irritating smell that when smelt directly didn't really smell much like cinnamon. However when smelt through the bottle it was very obviously cinnamon. I dipped my finger in it to collect a small amount of the product which I then tasted. It burnt slightly and tasted strongly of cinnamon. It was actually quite pleasant.

Anyway, I know this isn't anything too crazy but I hope this post is even a little interesting or useful for someone. I don't really have any ideas for what to do with the cinnamaldehyde so if anyone has any ideas I'd be keen to hear them.


Sources
(1) https://homedistiller.org/forum/viewtopic.php?t=24199
(2) https://www.youtube.com/watch?v=m0aTZXjXnX0

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bnull
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[*] posted on 17-4-2024 at 10:22


You can demonstrate some reactions with it. An aldol condensation with some ketone. With acetone, for example, you get a precipitate of [url=(https://www.chemedx.org/JCESoft/jcesoftSubscriber/CCA/CCA5/M...)]dicinnamalacetone[/url]. Or a Cannizzaro reaction with formaldehyde.



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B. N. Ull

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Barney
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[*] posted on 18-4-2024 at 16:39


Oh yeah cheers those look like some fun reactions to do. The aldol condensation with acetone in particular looks pretty straightforward.
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