Production of Diethyl Terephthalate from Biomass-Derived Muconic Acid

被引：107

作者：

Lu, Rui ^{[1
,2
]}

Lu, Fang ^{[1
]}

Chen, Jiazhi ^{[1
,2
]}

Yu, Weiqiang ^{[1
]}

Huang, Qianqian ^{[1
,2
]}

Zhang, Junjie ^{[1
,2
]}

Xu, Jie ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Natl Lab Clean Energy, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 01期

基金：

中国国家自然科学基金;

关键词：

biomass; catalysis; cycloaddition; muconic acid; terephthalic acid; ADIPIC ACID; P-XYLENE; CATALYZED DEOXYDEHYDRATION; AEROBIC OXIDATION; LACTIC-ACID; ETHYLENE; CONVERSION; CYCLOADDITION; AROMATICS; CHEMICALS;

D O I：

10.1002/anie.201509149

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a cascade synthetic route to directly obtain diethyl terephthalate, a replacement for terephthalic acid, from biomass-derived muconic acid, ethanol, and ethylene. The process involves two steps: First, a substituted cyclohexene system is built through esterification and Diels-Alder reaction; then, a dehydrogenation reaction provides diethyl terephthalate. The key esterification reaction leads to improved solubility and modulates the electronic properties of muconic acid, thus promoting the Diels-Alder reaction with ethylene. With silicotungstic acid as the catalyst, nearly 100% conversion of muconic acid was achieved, and the cycloadducts were formed with more than 99.0% selectivity. The palladium-catalyzed dehydrogenation reaction preferentially occurs under neutral or mildly basic conditions. The total yield of diethyl terephthalate reached 80.6% based on the amount of muconic acid used in the two-step synthetic process.

引用

页码：249 / 253

页数：5

共 41 条

[1]

[Anonymous], 2012, Angew. Chem., Int. Ed.

[2] CYCLOADDITION .8. ETHYLENE AS A DIENOPHILE . A MINUTE AMOUNT OF 1,2 CYCLOADDITION OF ETHYLENE TO BUTADIENE [J].