I have been using acryloyl chloride to functionalise cyclodextrin. The first two batches were fine but the last 2 attempts had a low degree of substitution. I also noticed some white solid in the bottle, so it would seem that some of the acryloyl chloride has polymerised.
Is there any point persisting with this bottle? I figured any remaining liquid acryloyl chloride will likely have some short polymer chains in there and therefore I have little confidence in the synthesis.
If you think this has been already started to polymerized, only way to recycle or obtain some pure for of the monomer is a distillation which indeed going to be a quite challange to perform under moisture free environment. Also you can double check a LCMS to see percentage purity of your reagent.
If you are ambitious - vacuum distillation will purify your acryloyl chloride.
with these highly reactive materials, often useful to purchase in small quantities so each reaction is a new bottle of the material.
Dear all, if you have acrylic acid and thionyl chloride or other chlorination reagents you can freshly prepare it. Worth to mention that commercial acryloyl chloride is stabilized with few ppm hydroquinone, which may reacts with your cyclodextrin if not eliminated prior to use the acryloyl chloride. My Regards
https://www.researchgate.net/post/How-do-I-synthesize-acryloyl-chloride
Thanks all for your input. Luckily Sigma sell it in 5g, and the synthesis requires 5 mL, so just going to use this in future.
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