RESEARCH ARTICLE

Ionic liquid mediated esterification of alcohol with acetic acid

  • Beilei ZHOU ,
  • Yanxiong FANG ,
  • Hao GU ,
  • Saidan ZHANG ,
  • Baohua HUANG ,
  • Kun ZHANG
Expand
  • Faculty of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510090, China

Received date: 18 Apr 2008

Accepted date: 19 Oct 2008

Published date: 05 Jun 2009

Copyright

2014 Higher Education Press and Springer-Verlag Berlin Heidelberg

Abstract

Highly efficient esterification of alcohols with acetic acid by using a Brønsted acidic ionic liquid, i.e., 1-methyl-2-pyrrolidonium hydrogen sulfate ([Hnmp]HSO4), as catalyst has been realized. The turnover numbers (TON) were able to reach up to 11000 and turnover frequency (TOF) was 846. The catalytic system is suitable for the esterification of long chain aliphatic alcohols, benzyl alcohol and cyclohexanol with good yields of esters. The procedure of separating the product and catalyst is simple, and the catalyst could be reused. [Hnmp]HSO4 had much weaker corrosiveness than H2SO4. The corrosive rate of H2SO4 was 400 times more than that of [Hnmp]HSO4 to stainless steel.

Cite this article

Beilei ZHOU , Yanxiong FANG , Hao GU , Saidan ZHANG , Baohua HUANG , Kun ZHANG . Ionic liquid mediated esterification of alcohol with acetic acid[J]. Frontiers of Chemical Science and Engineering, 2009 , 3(2) : 211 -214 . DOI: 10.1007/s11705-009-0054-3

Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (Grant No. 20376015), Guangdong Provincial Natural Science Foundation (32491), the Foundation of Scientific and technological Planning Project of Guangzhou of China (2004J1-C0151 ).
1
Larock R C. Comprehensive Organic Transformations. New York: John Wiley and Sons Inc, 1999

2
Forbes D C, Weaver K J. Brønsted acidic ionic liquids: the dependence on water of the Fischer esterification of acetic acid and ethanol. J Mol Catal A: Chem, 2004, 214: 129-132

DOI

3
Welton T. Room-temperature ionic liquids: solvents for synthesis and catalysis. Chem Rev, 1999, 99: 2071-2083

DOI

4
Wasserscheid P, Welton T, eds. Ionic Liquids in Synthesis. Weinheim: Wiley-VCH, 2003

5
Sheldon R. Catalytic reactions in ionic liquids. Chem Commun, 2001, 2399-2407

DOI

6
Holbrey J D, Seddon K R. Ionic liquid. Clean Prod Process, 1999, 1: 223-236

7
Zhang S J, Lv X M. Ionic liquid-from foundational research to industrial application. Beijing: Science Publication, 2006

8
Judeh Z M A, Shen H Y, Chi B C, Feng L C, Selvasothi S. A facile and efficient nucleophilic displacement reaction at room temperature in ionic liquids. Tetrahedron Lett, 2002, 43: 9381-9384

DOI

9
Deng Y Q, Shi F, Beng J J, Qiao K. Ionic liquid as a green catalytic reaction medium for esterifications. J Mol Catal A: Chem, 2001,165: 33-36

DOI

10
Cole A C, Jensen J L, Ntai I, Tran K L T, Weaver K J, Forbes D C, Davis J H, Novel Brønsted acidic ionic liquids and their use as dual solvent-catalysts. J Am Chem Soc, 2002, 124: 5962-5963

DOI

11
Zhu H P, Yang F, Tang J, He M Y. Brønsted acidic ionic liquid 1-methylimidazolium tetrafluoroborate: a green catalyst and recyclable medium for esterification. Green Chem, 2003, 5: 38-39

DOI

12
Gui J Z, Cong X H, Liu D, Zhang X, Hu Z, Sun Z. Novel Brønsted acidic ionic liquid as efficient and reusable catalyst system for esterification. Catal Commun, 2004, 5: 473-477

DOI

Options
Outlines

/