1990•Journal of Polymer Science Part A Polymer ChemistryRequires access

On the synthesis of pure (meth) acrylate esters and their corresponding homopolymers

Stacy B. Evans, J. E. Mulvaney, Henry Kingston Hall

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Abstract

Abstract We have observed that homopolymers of certain (meth)acrylate esters, prepared by the Schotten–Baumann method of (meth)acryloyl chloride and desired alcohol, in the presence of triethylamine or pyridine, formed gels. The mechanism of gelation was investigated and found to be due to a diene impurity, (meth)acrylic anhydride, which cannot be easily separated from many (meth)acrylate esters. For preparation of pure (meth)acrylate esters, the SN2 displacement reaction of (meth)acrylate anion with the desired chloro compound is recommended. The yields of the two reactions are comparable, and even t‐butoxycarbonylmethyl methacrylate is produced in 73% yield by the recommended method.

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Abstract We have observed that homopolymers of certain (meth)acrylate esters, prepared by the Schotten–Baumann method of (meth)acryloyl chloride and desired alcohol, in the presence of triethylamine or pyridine, formed gels. The mechanism of gelation was investigated and found to be due to a diene impurity, (meth)acrylic anhydride, which cannot be easily separated from many (meth)acrylate esters. For preparation of pure (meth)acrylate esters, the SN2 displacement reaction of (meth)acrylate anion with the desired chloro compound is recommended. The yields of the two reactions are comparable, and even t‐butoxycarbonylmethyl methacrylate is produced in 73% yield by the recommended method.

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Available abstract

Abstract We have observed that homopolymers of certain (meth)acrylate esters, prepared by the Schotten–Baumann method of (meth)acryloyl chloride and desired alcohol, in the presence of triethylamine or pyridine, formed gels. The mechanism of gelation was investigated and found to be due to a diene impurity, (meth)acrylic anhydride, which cannot be easily separated from many (meth)acrylate esters. For preparation of pure (meth)acrylate esters, the SN2 displacement reaction of (meth)acrylate anion with the desired chloro compound is recommended. The yields of the two reactions are comparable, and even t‐butoxycarbonylmethyl methacrylate is produced in 73% yield by the recommended method.

Key concepts: Meth-, Acryloyl chloride, Acrylate, Triethylamine, Chemistry, Polymer chemistry, Methacrylate, Acrylate polymer

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