Reaction of Bacterial Poly-3-Hydroxybutyrate with Thionyl Chloride in the Presence of Zinc Chloride, and the Preparation of Chlorine-Containing Oligomers

Macromol Pub Date : 2023-07-02 DOI:10.3390/macromol3030025
A. Boyandin
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Abstract

The degradation patterns of bacterial poly-3-hydroxybutyrate (PHB) in chloroform solution under the action of thionyl chloride in the presence of zinc chloride were studied. When 2.5.mol of zinc chloride and 100 mmol of thionyl chloride were introduced into the solution of 25 mmol PHB, a decrease in the molecular weight of the polymer was observed. During the reaction, a relatively rapid decrease in the molecular weight of the polymer was noted in the first hour of the experiment; thus, the values of the weight-average molecular weight decreased from 840 kDa to 483, 167, 58.6, and 16.7 kDa after 1, 5, 24, and 96 h of the experiment, respectively. The polydispersity also gradually decreased from 2.69 at the beginning to 1.92 at the end of the experiment. Oligomers of PHB containing 3-chlorobutyric acid and 3-hydroxybutyryl chloride residues at the O and C ends of the polymer chain, respectively, were obtained. The results confirm the ability of thionyl chloride to interact with aliphatic esters in the presence of zinc compounds, and demonstrate the possibility of using this reaction to produce oligomeric derivatives of polyesters bearing chloralkyl and acid chloride functional groups.
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细菌聚3-羟基丁酸酯与氯化亚硫酰在氯化锌存在下的反应及含氯低聚物的制备
研究了细菌聚3-羟基丁酸酯(PHB)在氯化锌存在下,在亚硫酰氯作用下在氯仿溶液中的降解规律。当2.5。在25 mmol PHB溶液中加入mol氯化锌和100 mmol亚硫酰氯,聚合物的分子量有所下降。在反应过程中,在实验的第一个小时内,聚合物的分子量相对迅速地下降;实验1、5、24、96 h后,分子量从840 kDa分别下降到483,167,58.6,16.7 kDa。多分散度也从试验开始时的2.69逐渐下降到试验结束时的1.92。在聚合物链的O端和C端分别含有3-氯丁酸和3-羟基丁酰氯残基的PHB低聚物。结果证实了亚硫酰氯在锌化合物存在的情况下与脂肪酯相互作用的能力,并证明了利用该反应生产含有氯烷基和酸氯官能团的聚酯的低聚衍生物的可能性。
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