无溶剂体系中固定化脂肪酶Candida sp. 99-125催化合成油酸低碳醇酯

doi:10.3724/SP.J.1095.2013.20496

摘要/Abstract

摘要： 采用固定化脂肪酶Candida sp.99-125在无溶剂体系中催化合成油酸低碳醇酯，考察了加酶量、温度、酸醇摩尔比和醇结构对油酸酯化率的影响。结果表明,加酶量为底物质量的3%，最适温度为20 ℃，酸与醇摩尔比为1∶1，甲醇对该酶有一定的毒性，由于空间位阻效应，该酶对伯醇具有高选择性，对仲醇、叔醇的选择性低，且对长链脂肪酸催化活性高，对带支链的多元酸、多元醇活性低。该酶重复使用5次，酶活性基本没有降低。与传统的化学法相比，用该酶催化合成酯类化合物的色泽更浅。

关键词: 生物催化, 固定化脂肪酶, 酯化, 油酸低碳醇酯, 无溶剂体系

Abstract: The esterification between oleic acid and alkyl alcohols in solvent-free systems were catalyzed by an immobilized lipase from Candida sp.99-125. The effects of several factors including enzyme concentration, temperature, molar ratio of oleic acid to alkyl alcohols, and structure of alcohols have been also investigated. The results indicated that the reactions catalyzed by lipase at 20 ℃ with the presence of 3%(mass fraction) lipase, a 1∶1 molar ratio of oleic acid to alcohols, afforded products in high yields. Methanol has certain toxicity on the activity of the lipase. The enzyme showed high selectivity to primary alcohols and low selectivity to secondary and tertiary alcohols because of the sterical effect. It showed high activity to long chain fatty acids and low activity to polybasic acids and polyhydric alcohols with branched chain. The lipase showed no appreciable loss in activity after being continuously operated for 5 times. The enzymatic synthesis gave purer products, compared with the conventional chemical system.

Key words: enzymatic catalysis, immobilized lipase, esterification, oleates, solvent-free system

中图分类号:

O629.8

仲蕙, 方正, 邹宝华, 李昕, 郭凯. 无溶剂体系中固定化脂肪酶Candida sp. 99-125催化合成油酸低碳醇酯[J]. 应用化学, DOI: 10.3724/SP.J.1095.2013.20496.

ZHONG Hui1, FANG Zheng1, ZOU Baohua1, LI Xin2, GUO Kai2*. Immobilized-Lipase(Candida sp.99-125)-Catalyzed Esterification of Alkyl Oleates in Solvent-free Systems[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2013.20496.

参考文献

[１] He X L,Chen B Q,Tan T W. Enzymatic Synthesis of 2-Ethylhexyl Esters of Fatty Acids by Immobilized Lipase from Candida sp.99-125[J]. J Mol Catal B:Enz,2002,18(4/6):333-339.

[２] Kobayashi T. Lipase-Catalyzed Syntheses of Sugar Esters in Non-Aqueous Media[J]. Biotechnol Lett,2011,33(10):1911-1919.

[３] Sarney D B,Barnard M J,MacManus D A,et al. Application of Lipase to the Regioselective Synthesis of Sucrose Fatty Acid Monoesters[J]. J Am Oil Chem Soc,1996,73(11):1481-1487.

[４] Valivety R H,Johnston G A,Suckling C J,et al. Solvent Effects on Biocatalysis in Organic Systems:Equilibrium Position and Rates of Lipase Catalyzed Reactions[J]. Biotechnol Bioeng,1991,38(10):1137-1143.

[５] Ferrer M,Cruces M A,Plou F J,et al. A Simple Procedure for the Regioselective Synthesis of Fatty Acid Esters of Maltose, Leucrose, Maltotriose and n-Dodecyl Maltosides[J]. Tetrahedron,2000,56(24):4053-4061.

[６] Tan T W,Chen B Q,Ye H. Enzymatic Synthesis of 2-Ethylhexyl Palmitate by Lipase Immobilized on Fabric Membranes in the Batch Reactor[J]. Biochem Eng J,2006,29(1/2):41-45.

[７] Neta N A S,Santos J C,Sancho S O,et al. Enzymatic Synthesis of Sugar Esters and Their Potential as Surface-active Stabilizers of Coconut Milk Emulsions[J]. Food Hydrocolloids,2012,27(2):324-331.

[８] NI Wanxing,ZHANG Xiaoming. Lipase-Catalyzed Synthesis of Bio-Diesel in Solvent Free System[J]. Food and Machinery[JP],2007,23(1):25-28(in Chinese).

倪婉星,张晓鸣. 非水相脂肪酶催化合成生物柴油[J]. 食品与机械,2007,23(1):25-28.

[９] JING Liang,XU Yan,CAO Guangqun. Biosynthesis of Oleyl Oleate by Whole-Cell Lipase from Rhizopus Chinensis[J]. Chinese J Catal,2006,27(7):611-614(in Chinese).

金亮,徐岩,曹光群. 华根霉全细胞脂肪酶催化合成油酸油醇酯[J]. 催化学报,2006,27(7):611-614.

[１０] DENG Li,TAN Tianwei,WANG Fang. Studies of Enzymatic Synthesis of Biodiesel[J]. Chinese J Biotechnol,2003,19(1):97-101(in Chinese).

邓力,谭天伟,王芳. 脂肪酶催化合成生物柴油的研究[J]. 生物工程学报,2003,19(1):97-101.

[１１] Nie K L,Xie F,Wang F. Lipase Catalyzed Methanolysis to Produce Biodiesel:Optimization of the Biodiesel Production[J]. J Mol Catal B:Enz,2006,43(1/4):142-147.

[１２] Lu J K,Nie K L,Xie F,et al. Enzymatic Synthesis of Fatty Acid Methyl Esters from Lard with Immobilized Candida sp.99-125[J]. Process Biochem,2007,42(9):1367-1370.

[１３] Drm N,Bélafi-Bakó K,Bartha L,et al. Manufacture of an Environmental-safe Biolubricant from Fusel Oil by Enzymatic Esterification in Solvent-free System[J]. Biochem Eng J,2004,21(3):229-234.

编辑推荐 0

Metrics

阅读次数

全文

491

HTML			PDF

最新录用	在线预览	正式出版	最新录用	在线预览	正式出版
0	0	0	491	0	0

来源	本网站	其他网站

次数	461	30
比例	94%	6%

摘要

409

最新录用	在线预览	正式出版

409	0	0

	来源	本网站

	次数	409
	比例	100%

[1]	陈丽燕, 谈东兴, 韩福社. 三［（S）-α，α-二（4-甲基苯基）-2-吡咯烷甲醇］膦酰胺催化链状酮酯化合物的不对称还原反应[J]. 应用化学, 2022, 39(3): 425-438.
[2]	史红玲, 王文杰, 李祥, 焦铸锦, 刘钺, 唐存多, 阚云超, 姚伦广. D-扁桃酸脱氢酶和L-亮氨酸脱氢酶级联催化的L-苯甘氨酸对映选择性生物合成[J]. 应用化学, 2020, 37(2): 168-174.
[3]	郭炜, 王亚明, 蒋丽红, 郑燕娥, 刘壁莹. 磺酸化手性向列型介孔二氧化硅的制备及其催化合成龙脑[J]. 应用化学, 2020, 37(12): 1447-1456.
[4]	陈红云,杨方红,李宇鹏,何佳玉,车梦琴,王美晨,程传杰. 水溶性Fe₃O₄磁性纳米催化剂的合成及应用[J]. 应用化学, 2019, 36(2): 188-194.
[5]	赖华, 刘兴, 朱小明, 龙婉君, 李想, 熊平生. 阻燃剂9,10-二氢-9-氧杂-10-膦杂菲-10-氧化物合成中酯化反应和酰基化反应的优化[J]. 应用化学, 2017, 34(2): 151-157.
[6]	李科, 张教强, 康拴艳, 石绘敏, 周宏玉, 豆荣荣. 二茂铁甲酸(2-丙烯酰氧乙基)酯的合成及优化[J]. 应用化学, 2015, 32(7): 765-770.
[7]	李亚男, 何文军, 俞峰萍, 陈梁锋, 戈军伟. 离子交换树脂在有机催化反应中的应用进展[J]. 应用化学, 2015, 32(12): 1343-1357.
[8]	李斌, 王晶, 裘立群, 宋少芳. 十六烷基三甲基溴化铵/聚乙二醇辛基苯基醚微乳液凝胶固定化脂肪酶催化水解消旋布洛芬辛酯[J]. 应用化学, 2014, 31(09): 1044-1049.
[9]	潘佳佳, 张贝克, 卢秉南. 强酸性阳离子交换树脂催化酯化丙烯酸和甲醇合成丙烯酸甲酯的反应动力学[J]. 应用化学, 2014, 31(02): 171-176.
[10]	苏策, 夏淑娇, 王蕊. N-杂环卡宾催化下对硝基苯甲醛的氧化酯化[J]. 应用化学, 2014, 31(02): 165-170.
[11]	李连贵, 李洋, 叶冲, 张强, 姜敏, 周光远. 聚2,5-呋喃二甲酸1,8-辛二酯的聚合反应[J]. 应用化学, 2013, 30(06): 661-666.
[12]	王军, 胡小丽, 文伟河, 杨雷雷, 朱玉亮. 甘草次酸3位氨基酸衍生物的合成及其抑菌活性[J]. 应用化学, 2012, 29(08): 873-877.
[13]	刘茜, 姜敏, 周光远, 张强, 叶冲, 熬玉辉. 直接酯化法合成聚2,5-呋喃二甲酸乙二酯[J]. 应用化学, 2012, 29(07): 751-756.
[14]	朱文帅, 吴沛文, 时花, 李华明, 黄卫红, 闫永胜, 王志高. 微波促进酸性离子液体催化水杨酸酯化[J]. 应用化学, 2011, 28(09): 1096-1098.
[15]	饶蔚兰, 潘志权, 向守信. 稀土固体超强酸的制备及其对硬脂肪酸酯化反应的催化[J]. 应用化学, 2011, 28(08): 907-912.