Synthesis of Crystalline and Amphiphilic Polymers from d-Glucaric Acid

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• 作者：Yuxin Wu ; Yukiko Enomoto-Rogers ; Hisaharu Masaki ; Tadahisa Iwata
• 刊名：ACS Sustainable Chemistry & Engineering
• 出版年：2016
• 出版时间：July 5, 2016
• 年：2016
• 卷：4
• 期：7
• 页码：3812-3819
• 全文大小：476K
• 年卷期：0
• ISSN：2168-0485

文摘

d-Glucaric acid (GA), an aldaric acid isolated from various vegetables and fruits, is an important biobased building block. Glucaric acid acetate (GAA), which is acyclic, was synthesized in an acetic anhydride/sulfuric acid mixture. GAA was converted to glucaric acid chloride acetate (GACA) and then polymerized with various diols and diamines in dimethylacetamide solution or by interfacial polymerization in water and chloroform solutions. The polyesters and polyamides were amphiphilic and soluble in water and common organic solvents. The weight-average molecular weights of the polyesters were (0.4–0.7) × 10³; those of the polyamides obtained by solution and interfacial polymerizations were (5.9–8.0) × 10³ and (14.5–20.8) × 10³, respectively. Differential scanning calorimetry showed that the polyamides were thermoplastic and melted at ca. 140 °C, indicating crystallinity; the melting points increased with increasing number of diamine alkyl carbons. Novel biobased crystalline amphiphilic polymers were synthesized from GA.