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Author: Subject: Cinnamaldehyde Decomposition?
Hazard to Self

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sad.gif posted on 10-1-2017 at 16:51
Cinnamaldehyde Decomposition?

I ended up spending all of today on just one project due to equipment failures and whatnot, and then at the end of it, there seems to be no product....

I intended to follow Nile Red's video on steam distilling cinnamaldehyde:

I only made a few differences in the procedure:
1) I didn't use an addition funnel to add another 100mL of water after the first 100mL of distillate was collected.
2) I didn't dry the organic layer with saturated salt solution, but I did dry it with CaCl2 until the layer was clear.
3) I distilled off the DCM using a heating mantle not a hot water bath, but kept it on low to medium heat.

At the end I wasn't left with an oil but some crusty off-white solid stuck to the bottom of the flask, it smelled of cinnamon but also had a slight rose/floral hint to it. Any ideas as to what happened?
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[*] posted on 10-1-2017 at 17:20

Cinnamic acid with traces of cinnamate esters and cinnamaldehyde. Cinnamic acid is highly sensitive to air oxidation and working in large volumes of solvent is a great way to end up with it oxidized. Possibly your cinnamon was already old and oxidized as well.

Edit: I should point out that what is being used in the video is cassia (Cinnamomum cassia) bark, sold in the US as cinnamon. It's essential oil is 80+% cinnamaldehyde. True or Ceylon cinnamon (Cinnamomum verum) comes in larger sticks and has a layered fibrous look to it. That essential oil is only about 50% cinnamaldehyde with a considerable amount of eugenol and a lot of other minor components).

[Edited on 11-1-2017 by UC235]
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