Lipase-catalyzed Synthesis of Caffeic Acid Phenethyl Ester in Ionic Liquids：Effect of Specific Ions and Reaction Parameters

doi:10.1016/S1004-9541(13)60563-7

Chin.J.Chem.Eng. ›› 2013, Vol. 21 ›› Issue (12): 1376-1385.DOI: 10.1016/S1004-9541(13)60563-7

• BIOTECHNOLOGY AND BIOENGINEERING • Previous Articles Next Articles

Lipase-catalyzed Synthesis of Caffeic Acid Phenethyl Ester in Ionic Liquids：Effect of Specific Ions and Reaction Parameters

WANG Jun¹, LI Jing¹, ZHANG Leixia¹, GU Shuangshuang¹, WU Fuan^1,2

1 School of Biology and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212018, China;
2 Sericultural Research Institute, Chinese Academy of Agricultural Sciences, Zhenjiang 212018, China

Received:2012-11-12 Revised:2013-02-28 Online:2013-12-27 Published:2013-12-28
Contact: WANG Jun, WU Fuan
Supported by:
Supported by the Natural Science Foundation of Jiangsu Province (BK2009213), China Postdoctoral Science Foundation funded Project (2012M510124), Qing Lan Project of Jiangsu Province, National Natural Science Foundation of China (21206061), Research Project of Jiangsu University of Science and Technology (35211002), and Modern Agro-industry Technology Research System of China (CARS-22).

Lipase-catalyzed Synthesis of Caffeic Acid Phenethyl Ester in Ionic Liquids：Effect of Specific Ions and Reaction Parameters

王俊¹, 李晶¹, 张磊霞¹, 顾双双¹, 吴福安^1,2

1 School of Biology and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212018, China;
2 Sericultural Research Institute, Chinese Academy of Agricultural Sciences, Zhenjiang 212018, China

通讯作者: WANG Jun, WU Fuan
基金资助:
Supported by the Natural Science Foundation of Jiangsu Province (BK2009213), China Postdoctoral Science Foundation funded Project (2012M510124), Qing Lan Project of Jiangsu Province, National Natural Science Foundation of China (21206061), Research Project of Jiangsu University of Science and Technology (35211002), and Modern Agro-industry Technology Research System of China (CARS-22).

Abstract

Abstract: Caffeic acid phenethyl ester (CAPE) is a rare, naturally occurring phenolic food additive. This work systematically reported fundamental data on conversion of caffeic acid (CA), yield of CAPE, and reactive selectivity during the lipase-catalyzed esterification process of CA and phenylethanol (PE) in ionic liquids (ILs). Sixteen ILs were selected as the reaction media, and the relative lipase-catalyzed synthesis properties of CAPE were measured in an effort to enhance the yield of CAPE with high selectivity. The results indicated that ILs containing weakly coordinating anions and cations with adequate alkyl chain length improved the synthesis of CAPE. [Emim][Tf₂N] was selected as the optimal reaction media. The optimal parameters were as follows by response surface methodology (RSM): reaction temperature, 84.0 ℃; mass ratio of Novozym 435 to CA, 14:1; and molar ratio of PE to CA, 16:1. The highest reactive selectivity of CAPE catalyzed by Novozym 435 in [Emim][Tf₂N] reached 64.55% (CA conversion 98.76% and CAPE yield 63.75%, respectively). Thus, lipase-catalyzed esterification in ILs is a promising method suitable for CAPE production.

Key words: biocatalysis, caffeic acid phenethyl ester, esterification, ionic liquid, lipase, response surface methodology

摘要： Caffeic acid phenethyl ester (CAPE) is a rare, naturally occurring phenolic food additive. This work systematically reported fundamental data on conversion of caffeic acid (CA), yield of CAPE, and reactive selectivity during the lipase-catalyzed esterification process of CA and phenylethanol (PE) in ionic liquids (ILs). Sixteen ILs were selected as the reaction media, and the relative lipase-catalyzed synthesis properties of CAPE were measured in an effort to enhance the yield of CAPE with high selectivity. The results indicated that ILs containing weakly coordinating anions and cations with adequate alkyl chain length improved the synthesis of CAPE. [Emim][Tf₂N] was selected as the optimal reaction media. The optimal parameters were as follows by response surface methodology (RSM): reaction temperature, 84.0 ℃; mass ratio of Novozym 435 to CA, 14:1; and molar ratio of PE to CA, 16:1. The highest reactive selectivity of CAPE catalyzed by Novozym 435 in [Emim][Tf₂N] reached 64.55% (CA conversion 98.76% and CAPE yield 63.75%, respectively). Thus, lipase-catalyzed esterification in ILs is a promising method suitable for CAPE production.

关键词: biocatalysis, caffeic acid phenethyl ester, esterification, ionic liquid, lipase, response surface methodology

WANG Jun, LI Jing, ZHANG Leixia, GU Shuangshuang, WU Fuan. Lipase-catalyzed Synthesis of Caffeic Acid Phenethyl Ester in Ionic Liquids：Effect of Specific Ions and Reaction Parameters[J]. Chin.J.Chem.Eng., 2013, 21(12): 1376-1385.

王俊, 李晶, 张磊霞, 顾双双, 吴福安. Lipase-catalyzed Synthesis of Caffeic Acid Phenethyl Ester in Ionic Liquids：Effect of Specific Ions and Reaction Parameters[J]. Chinese Journal of Chemical Engineering, 2013, 21(12): 1376-1385.

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Lipase-catalyzed Synthesis of Caffeic Acid Phenethyl Ester in Ionic Liquids：Effect of Specific Ions and Reaction Parameters

Lipase-catalyzed Synthesis of Caffeic Acid Phenethyl Ester in Ionic Liquids：Effect of Specific Ions and Reaction Parameters

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