Lactonization and condensation polymerization of 5-hydroxylevulinic acid
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ZHANG Yan; WU Linbo;LI Feng;LI Bogeng
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5-羟基乙酰丙酸的内酯化与缩聚反应
张艳;吴林波;李枫;李伯耿
浙江大学化学工程与生物工程学系,化学工程国家重点联合实验室聚合反应工程实验室,浙江 杭州 310027
Abstract: 5-Hydroxylevulinic acid (5-HLA) was synthesized via modified bromination and hydrolysis using levulinic acid (LA) as starting material. Based on the hydroxyl and the carboxyl groups of the 5-HLA, poly(5-hydroxylevulinic acid), a novel aliphatic polyester, was synthesized by direct polycondensation using SnCl28226;2H2O as catalyst. In addition, 1,6,9,13-tetraoxadispiro [4.2.4.2]tetradecane-2,10-dione (or altaicadispirolactone), a dimer of the 5-HLA, was synthesized by cyclolactonization catalyzed by BF38226;OEt2. Altaicadispirolactone is one of the chemical components of Anemone altaica C.A.May, a traditional Chinese medicinal material. Structures of the dimer and the polymer were characterized with GC-MS,1H NMR, FT-IR, element analysis and GPC, respectively. Two plausible mechanisms for the cyclolactonization reaction were presented.
摘要: 以乙酰丙酸(LA)为原料,通过改进的溴化、水解反应,合成5-羟基乙酰丙酸(5-HLA).基于5-HLA的羟基和羧基,将其作为单体,氯化亚锡为催化剂,经缩聚得到了一种新的脂肪族聚酯——聚5-羟基乙酰丙酸(PHLA).另以BF38226;OEt2为催化剂,进行5-HLA的内酯化反应,得到了二聚体[BF]1,6,9,13-[BFQ]四氧双螺[4. 2. 4. 2]十四烷-2,10-二酮(又称阿尔泰内酯),它是中药九节菖蒲的化学成分之一.分别用气质联用、核磁、红外、元素分析和凝胶渗透色谱等方法对所得二聚体以及聚合物结构进行表征,讨论了有关的反应机理.
ZHANG Yan; WU Linbo;LI Feng;LI Bogeng.
张艳;吴林波;李枫;李伯耿 .
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https://hgxb.cip.com.cn/EN/Y2006/V57/I4/992