Tuning the acidity of sulfonic functionalized ionic liquids for highly efficient and selective synthesis of terpene esters

Duan-Jian Tao; Yan Dong; Zhi-Jun Cao; Feng-Feng Chen; Xiang-Shu Chen; Kuan Huang

Journal of Industrial and Engineering Chemistry, Vol.41, 122-129, September, 2016

DOI10.1016/j.jiec.2016.07.014 Export Citation

Tuning the acidity of sulfonic functionalized ionic liquids for highly efficient and selective synthesis of terpene esters

Duan-Jian Tao^†, Yan Dong, Zhi-Jun Cao, Feng-Feng Chen, Xiang-Shu Chen^†, and Kuan Huang¹

College of Chemistry and Chemical Engineering, Jiangxi Inorganic Membrane Materials Engineering Research Center, Jiangxi Normal University, Nanchang 330022, China
¹Department of Chemistry, University of Tennessee, Knoxville, TN 37996, USA

E-mail:,

A series of sulfonic functionalized ionic liquids (SFILs) with different acidity were designed and prepared for the synthesis of terpene esters (e.g. geranyl acetate). The effect of acidity of SFILs on their performance was investigated systematically. It is found that tuning the acidity of SFILs to an appropriate value results in not only high conversion of geraniol but also superior selectivity of geranyl acetate. The SFILs can be easily separated from products by filtration under room temperature, thus showing good reusability. Furthermore, the kinetics for SFILs in the esterification of geraniol were determined as the basis for future process design.

Keywords:Acidity;Sulfonic functionalized ionic liquids;Terpene esters;Kinetic

[References]

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[2] Chatterjee T, Bhattacharyya DK, Biotechnol. Lett., 20(9), 865 (1998)

[3] Mullen BA, U.S. Patent 2,005,002,980, 2005.

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[5] Geyer S, Zeiger W, Mayer R, Z. Chem., 6, 138 (1966)

[6] Harmer MA, Sun Q, Appl. Catal. A: Gen., 221(1-2), 45 (2001)

[7] Li L, Yu ST, Liu FS, Yang JZ, Zhaug SF, Catal. Lett., 100(3-4), 227 (2005)

[8] Lozano P, Bernal JM, Navarro A, Green Chem., 14, 2953 (2012)

[9] You PY, Su EZ, Yang XP, Mao DB, Wei DZ, J. Mol. Catal. B-Enzym., 71, 152 (2011)

[10] Liu JH, Huang YR, J. Biotechnol., 146, 215 (2010)

[11] Couto R, Vidinha P, Peres C, Ribeiro AS, Ferreira O, Oliveira MV, Macedo EA, Loureiro JM, Barreiros S, Ind. Eng. Chem. Res., 50(4), 1938 (2011)

[12] Serra S, Fuganti C, Brenna E, Trends Biotechnol., 23, 193 (2005)

[13] Olivier-Bourbigou H, Magna L, Morvan D, Appl. Catal. A: Gen., 373(1-2), 1 (2010)

[14] Hallett JP, Welton T, Chem. Rev., 111(5), 3508 (2011)

[15] Wilkes JS, Green Chem., 4, 73 (2002)

[16] Zhang Q, Zhang S, Deng Y, Green Chem., 13, 2619 (2011)

[17] Tang S, Scuto AM, Subramaniam B, J. Catal., 268, 732 (2009)

[18] Taheri A, Lai BB, Cheng C, Gu YL, Green Chem., 17, 812 (2015)

[19] Chinnappan A, Kim H, Chem. Eng. J., 187, 283 (2012)

[20] Zhang HB, Xu F, Zhou XH, Zhang GY, Wang CX, Green Chem., 9, 1208 (2007)

[21] Singh RK, Gupta P, Sharma OP, Ray SS, J. Ind. Eng. Chem., 24, 14 (2015)

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[24] Ren YM, Shao JJ, Wu ZC, Yang RC, Zhang Z, Tao TX, Synth. Commun., 44, 2529 (2014)

[25] Tao DJ, Li ZM, Cheng Z, Hu N, Chen XS, Ind. Eng. Chem. Res., 51(50), 16263 (2012)

[26] Li ZM, Zhou Y, Tao DJ, Huang W, Chen XS, Yang Z, RSC Adv., 4, 12160 (2014)

[27] Zhao Y, Long J, Deng F, Liu X, Li Z, Xia C, Peng J, Catal. Commun., 10, 732 (2009)

[28] Kore R, Srivastava R, Catal. Commun., 12, 1420 (2011)

[29] Tao DJ, Wu J, Wang ZZ, Lu ZH, Yang Z, Chen XS, RSC Adv., 4, 1 (2014)

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[34] Yang YL, Kou Y, Chem. Commun., 2, 226 (2004)

[35] Liao XY, Wang SG, Xiang XM, Zhu YL, She XC, Li YW, Fuel Process. Technol., 96, 74 (2012)

[36] Tao DJ, Wu J, Wang ZZ, Lu ZH, Yang Z, Chen XS, RSC Adv., 4, 1 (2014)

[37] Liu Y, Wang YT, Liu T, Tao DJ, RSC Adv., 4, 22520 (2014)

[38] Williams CM, Whittaker D, J. Chem. Soc. B, 672 (1971)

[39] Kolah AK, Asthana NS, Vu DT, Lira CT, Miller DJ, Ind. Eng. Chem. Res., 47(15), 5313 (2008)

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