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Biocatalytic and solvent-free synthesis of a bio-based biscyclocarbonate
Green Chemistry ( IF 9.8 ) Pub Date : 2018-09-25 , DOI: 10.1039/c8gc02267d
D. S. Wunschik 1, 2, 3, 4, 5 , K. N. Ingenbosch 1, 2, 3, 4, 5 , M. Zähres 4, 6, 7, 8 , J. Horst 1, 2, 3, 4 , C. Mayer 4, 6, 7, 8 , M. Jäger 1, 2, 3, 4 , V. Strehmel 1, 2, 3, 4 , M. Dornbusch 1, 2, 3, 4 , K. Hoffmann-Jacobsen 1, 2, 3, 4
Affiliation  

A biocatalytic synthesis of sebacic biscyclocarbonate has been developed. Sebacic biscyclocarbonate is a monomer for non-isocyanate polyurethane (NIPU) synthesis. The synthesis was performed in neat glycerol carbonate in the presence of lipase B from Candida antarctica (CalB immo Plus). The bifunctional molecule was synthesized directly from the bio-based reactants sebacic acid and glycerol carbonate, a product of glycerol. The optimization of reaction conditions in terms of reaction time and temperature revealed a temperature optimum at room temperature in contrast to the activity optimum of the lipase. NMR analysis was used to investigate the dominant competing reactions and the mechanism of selectivity at the optimized reaction parameters. 1H- and 13C-NMR as well as mass spectrometry confirm that sebacic biscyclocarbonate can be synthesized in the highest purity by the optimized process.

中文翻译:

生物基双环碳酸酯的生物催化和无溶剂合成

已经开发了癸二酸双环碳酸酯的生物催化合成。癸二酸双环碳酸酯是非异氰酸酯聚氨酯(NIPU)合成的单体。在来自南极假丝酵母的脂肪酶B (CalB immo Plus)的存在下,在纯净的碳酸甘油酯中进行合成。双功能分子直接由生物基反应物癸二酸和甘油的产物碳酸甘油酯合成。与反应时间和温度有关的反应条件的优化揭示了在室温下与脂肪酶的活性最适相反的最适温度。NMR分析用于研究主要竞争反应以及在最佳反应参数下的选择性机理。1 H-和13 C-NMR以及质谱分析证实,通过优化工艺可以合成出最高纯度的癸二酸双环碳酸酯。
更新日期:2018-10-15
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