Remarkably efficient hydrolysis of cinnamaldehyde to natural benzaldehyde in amino acid ionic liquids

Shu Xu; Duan-Jian Tao; Feng-Feng Chen; Yan Zhou; Xin Zhao; Li-Li Yu; Xiang-Shu Chen; Kuan Huang

Korean Journal of Chemical Engineering, Vol.33, No.12, 3374-3380, December, 2016

DOI10.1007/s11814-016-0204-5 Export Citation

Remarkably efficient hydrolysis of cinnamaldehyde to natural benzaldehyde in amino acid ionic liquids

Shu Xu, Duan-Jian Tao^†, Feng-Feng Chen, Yan Zhou, Xin Zhao, Li-Li Yu¹, Xiang-Shu Chen^†, and Kuan Huang²

College of Chemistry and Chemical Engineering, Jiangxi Inorganic Membrane Materials Engineering Research Center, Jiangxi Normal University, Nanchang 330022, China
¹Department of Pharmacy, Xi’an Medical University, Xi’an 710021, China
²Department of Chemistry, University of Tennessee, Knoxville TN 37996, U.S.A., USA

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The hydrolysis of cinnamaldehyde to natural benzaldehyde was investigated systematically using tetramethylammonium-based amino acid ionic liquids as homogeneous catalysts. The results indicated that tetramethylammonium prolinate ([N1111][Pro]) can be a powerful catalyst for the highly efficient hydrolysis of cinnamaldehyde, in which natural benzaldehyde was obtained with almost 94% yield and over 99% selectivity in 1 h. Moreover, kinetic study showed that compared with other catalysts, the catalytic system of [N1111][Pro] has a lower activation energy of 38.30 kJ·mol-1 in the hydrolysis reaction, indicating superior catalytic performance of [N1111][Pro]. Quantum-mechanical calculations further manifested that such high performance originates from the cooperative catalysis of the secondary amino and carboxyl group in the anion [Pro].

Keywords:Natural Benzaldehyde;Cinnamaldehyde;Hydrolysis;Ionic Liquids

[References]

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[Referenced By]

[1] Wolken AMW, Tramper J, Werf VDMJ, Flavour Fragr. J., 19, 115 (2004)

[2] Chen HY, Ji HB, Zhou XT, Xu JC, Wang LF, Catal. Commun., 10, 828 (2009)

[3] Chen HY, Ji HB, Zhou XT, Wang LF, Tetrahedron, 66, 9888 (2010)

[4] Chen HY, Ji HB, AIChE J., 56(2), 466 (2010)

[5] Gao F, Lv XY, J. Chem. Eng. Chin. Univ., 20, 544 (2006)

[6] Yang ZJ, Zeng H, Zhou XT, Ji HB, Tetrahedron, 68, 5912 (2012)

[7] Yang ZJ, Ji HB, ACS Sustainable Chem. Eng., 1, 1172 (2013)

[8] Yadav GD, Fernandes GP, Catal. Today, 207, 162 (2013)

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

[10] Luo X, Guo Y, Ding F, Zhao H, Cui G, Li H, Wang C, Angew. Chem.-Int. Edit., 53, 7053 (2014)

[11] Tao DJ, Ouyang F, Li ZM, Hu N, Yang Z, Chen XS, Ind. Eng. Chem. Res., 52(48), 17111 (2013)

[12] Long JX, Lou WY, Wang LF, Yin BL, Li XH, Chem. Eng. Sci., 122, 24 (2015)

[13] Armand M, Endres F, MacFarlane DR, Ohno H, Scrosati B, Nat. Mater., 8(8), 621 (2009)

[14] Fukumoto K, Yoshizawa M, Ohno H, J. Am. Chem. Soc., 127(8), 2398 (2005)

[15] Tao GH, He L, Liu WS, Xu L, Xiong W, Wang T, Kou Y, Green Chem., 8, 639 (2006)

[16] Ohno H, Fukumoto K, Acc. Chem. Res., 40, 1122 (2007)

[17] Tao DJ, Cheng Z, Chen FF, Li ZM, Hu N, Chen XS, J. Chem. Eng. Data, 58(6), 1542 (2013)

[18] Petkovic M, Seddon KR, Rebelo LPN, Pereira CS, Chem. Soc. Rev., 40, 1383 (2011)

[19] Jiang YY, Wang GN, Zhou Z, Wu YT, Geng J, Zhang ZB, Chem. Commun., 508 (2008)

[20] Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, GAUSSIAN 09 (Revision. C.01), Gaussian, Inc., Wallingford, CT (2009).

[21] Chen HY, Yang ZJ, Zhou XT, Ji XB, Supramol. Chem., 24, 247 (2012)

[22] Yang ZJ, Zeng H, Zhou XY, Ji HB, Supramol. Chem., 25, 233 (2013)

[23] Enders D, Nguyen TV, Tetrahedron Lett., 53, 2091 (2012)

[24] Erkkila A, Majander I, Pihko PM, Chem. Rev., 107(12), 5416 (2007)

[25] Wolken WA, Have RT, Werf MJVD, J. Agric. Food Chem., 48, 5401 (2000)