The driving effect of substituent size changes on reaction: a novel reaction for direct production of triacetylglycerol from oils and fats

Lijuan Su; Xianglin Hou; Xiaojing Cui; Xingchen Liu; Hongliang Wang; Jiaojiao Zhang; Jinlong Li; Yingxiong Wang; Tiansheng Deng

doi:10.1039/D0GC02485F

The driving effect of substituent size changes on reaction: a novel reaction for direct production of triacetylglycerol from oils and fats†

Lijuan Su,^abc Xianglin Hou,^abc Xiaojing Cui,^bd Xingchen Liu,^bd Hongliang Wang,^e Jiaojiao Zhang,^abc Jinlong Li,^abc Yingxiong Wang^abc and Tiansheng Deng

*^abc

Author affiliations

* Corresponding authors

^a Shanxi Engineering Research Center of Biorefinery, Institute of Coal Chemistry, Chinese Academy of Sciences, 27 South Taoyuan Road, Taiyuan 030001, China
E-mail: dts117@sxicc.ac.cn

^b Center of Materials Science and Optoelectronics Engineering, University of Chinese Academy of Sciences, Beijing 100049, China

^c CAS Key Laboratory of Carbon Materials, Institute of Coal Chemistry, Chinese Academy of Sciences, 27 South Taoyuan Road, Taiyuan 030001, China

^d State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, 27 South Taoyuan Road, Taiyuan 030001, China

^e Center of Biomass Engineering/College of Agronomy and Biotechnology, China Agricultural University, Beijing, China

Abstract

The existing triacetylglycerol (TAG) production method involves esterification of oil (fat)-derived glycerol with acetic acid, forming a mixture of mono-, di- and tri- acetylglycerols. Herein, a new acyl exchange reaction is developed to directly and efficiently produce TAG from waste oils and fats by the driving effect of substituent size changes. Small-sized acetic acids easily replace large long-chain fatty acids of oils. This release in the intramolecular tension and diminishing of steric hindrance make TAG both thermodynamically and dynamically the most favorable product. Pure TAG was obtained with a high yield of 94.9%.

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DOI: https://doi.org/10.1039/D0GC02485F
Article type: Communication
Submitted: 20 Jul 2020
Accepted: 03 Sep 2020
First published: 03 Sep 2020

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Green Chem., 2020,22, 6345-6350

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The driving effect of substituent size changes on reaction: a novel reaction for direct production of triacetylglycerol from oils and fats

L. Su, X. Hou, X. Cui, X. Liu, H. Wang, J. Zhang, J. Li, Y. Wang and T. Deng, Green Chem., 2020, 22, 6345 DOI: 10.1039/D0GC02485F

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Green Chemistry

The driving effect of substituent size changes on reaction: a novel reaction for direct production of triacetylglycerol from oils and fats†

Abstract

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The driving effect of substituent size changes on reaction: a novel reaction for direct production of triacetylglycerol from oils and fats

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