The preparation and acid‐catalyzed hydrolysis of polyoxymethylene isopropyl methyl ethers

摘要

AbstractThe first four members of the polyoxymethylene ether series (CH3)2CHO(CH2O)nCH3were prepared, separated by fractional distillation and GLC, and characterized by NMR. Rate constants for the aqueous acid hydrolysis of the compounds were determined at 25°, 30°, and 35°C. Although the polyformals (n>1) in this series hydrolyzed at essentially the same rate, they all hydrolyzed three times faster than the formal (n= 1). It is proposed that a mixed polyformal, (CH3)2CHO (CH2O)n>1CH3, undergoes two concurrent fissions to yield (1) the stem (CH3)2CHOCH2with CH3O(CH2O)n−1as the leaving group and (2) the stem CH3OCH2with (CH3)2CHO(CH2O)n−1as the leaving group. Most of the fissions occur by the first path. An equation that can aid in predicting the rate of hydrolysis of a mixed polyformal was developed and