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New high-yield, one-step synthesis of polyglycolide from haloacetic acids

✍ Scribed by Pinkus, A. G. ;Subramanyam, Ravi

Publisher
John Wiley and Sons
Year
1984
Weight
594 KB
Volume
22
Category
Article
ISSN
0360-6376

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✦ Synopsis

Abstract

In a new, one‐step synthesis, polyglycolide was prepared by the reaction of bromo‐ or chloroacetic acid with triethylamine in a nitromethane solution. It was discolored, by iodoacetic acid possibly as a result of iodine formed by the decomposition of triethylammonium iodide. The structure of polyglycolide was characterized by hydrolysis, ^1^H‐NMR and IR spectra, and x‐ray powder diffraction, which indicated partial crystallinity. A mechanism is proposed for the formation of polyglycolide. A lower limiting value of the number‐average molecular weight of 10^4^ was determined by cryoscopy in 1,3‐dinitrobenzene for polyglycolide prepared from bromoacetic acid; the measurement was inaccurate because of the low solubility of the polymer. No significant effect of solvent (acetone, ether, or chloroform) on yield or melting point was observed; a higher yield was obtained in nitromethane. The polymer obtained with tri‐n‐propylamine and bromoacetic acid had properties similar to that obtained with triethylamine. No polymer was obtained with N,N‐dimethylaniline and bromoacetic acid or with triethylamine and bromoacetic acid in aqueous solution.

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