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Oxidation of Cyclohexanone with Peracids-A Straight Path to the Synthesis of ε-Caprolactone Oligomers.

ABSTRACT: During Baeyer-Villiger (BV) oxidation of cyclohexanone with peracids, oligo(ε-caprolactone) (OCL) may be formed. In this work, a two-step one-pot method for the synthesis of OCL involving the BV oxidation of cyclohexanone with peracids and then oligomerization of the resulting ε-caprolactone has been developed. The process was carried out in two solvents: toluene and cyclohexane. Based on the studies, it was determined that the increased temperature (45-55 °C) and the longer reaction time (4 h) favor the formation of OCls. Among the tested peracids (perC8-C12), perC10 turned out to be the most effective oxidant. Moreover, the obtained oligomers were characterized by means of NMR, MS MALDI TOF, and TGA analyses, which made it possible to determine the structure of oligomers (length and terminal groups of the chains). Additionally, the oligomers obtained after the distillation of the reaction mixture were analyzed.

SUBMITTER: Binczak J 

PROVIDER: S-EPMC9571306 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Oxidation of Cyclohexanone with Peracids-A Straight Path to the Synthesis of ε-Caprolactone Oligomers.

Bińczak Jakub J   Szelwicka Anna A   Siewniak Agnieszka A   Dziuba Krzysztof K   Chrobok Anna A  

Materials (Basel, Switzerland) 20220923 19

During Baeyer-Villiger (BV) oxidation of cyclohexanone with peracids, oligo(ε-caprolactone) (OCL) may be formed. In this work, a two-step one-pot method for the synthesis of OCL involving the BV oxidation of cyclohexanone with peracids and then oligomerization of the resulting ε-caprolactone has been developed. The process was carried out in two solvents: toluene and cyclohexane. Based on the studies, it was determined that the increased temperature (45-55 °C) and the longer reaction time (4 h)  ...[more]

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