| Issue |
Korean Journal of Chemical Engineering,
Vol.33, No.12, 3374-3380, 2016
Vol.33, No.12, 3374-3380, 2016
Remarkably efficient hydrolysis of cinnamaldehyde to natural benzaldehyde in amino acid ionic liquids
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].
[References]
- Wolken AMW, Tramper J, Werf VDMJ, Flavour Fragr. J., 19, 115, 2004
- Chen HY, Ji HB, Zhou XT, Xu JC, Wang LF, Catal. Commun., 10, 828, 2009
- Chen HY, Ji HB, Zhou XT, Wang LF, Tetrahedron, 66, 9888, 2010
- Chen HY, Ji HB, AIChE J., 56(2), 466, 2010
- Gao F, Lv XY, J. Chem. Eng. Chin. Univ., 20, 544, 2006
- Yang ZJ, Zeng H, Zhou XT, Ji HB, Tetrahedron, 68, 5912, 2012
- Yang ZJ, Ji HB, ACS Sustainable Chem. Eng., 1, 1172, 2013
- Yadav GD, Fernandes GP, Catal. Today, 207, 162, 2013
- Hallett JP, Welton T, Chem. Rev., 111(5), 3508, 2011
- Luo X, Guo Y, Ding F, Zhao H, Cui G, Li H, Wang C, Angew. Chem.-Int. Edit., 53, 7053, 2014
- Tao DJ, Ouyang F, Li ZM, Hu N, Yang Z, Chen XS, Ind. Eng. Chem. Res., 52(48), 17111, 2013
- Long JX, Lou WY, Wang LF, Yin BL, Li XH, Chem. Eng. Sci., 122, 24, 2015
- Armand M, Endres F, MacFarlane DR, Ohno H, Scrosati B, Nat. Mater., 8(8), 621, 2009
- Fukumoto K, Yoshizawa M, Ohno H, J. Am. Chem. Soc., 127(8), 2398, 2005
- Tao GH, He L, Liu WS, Xu L, Xiong W, Wang T, Kou Y, Green Chem., 8, 639, 2006
- Ohno H, Fukumoto K, Acc. Chem. Res., 40, 1122, 2007
- Tao DJ, Cheng Z, Chen FF, Li ZM, Hu N, Chen XS, J. Chem. Eng. Data, 58(6), 1542, 2013
- Petkovic M, Seddon KR, Rebelo LPN, Pereira CS, Chem. Soc. Rev., 40, 1383, 2011
- Jiang YY, Wang GN, Zhou Z, Wu YT, Geng J, Zhang ZB, Chem. Commun., 508, 2008
- 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).
- Chen HY, Yang ZJ, Zhou XT, Ji XB, Supramol. Chem., 24, 247, 2012
- Yang ZJ, Zeng H, Zhou XY, Ji HB, Supramol. Chem., 25, 233, 2013
- Enders D, Nguyen TV, Tetrahedron Lett., 53, 2091, 2012
- Erkkila A, Majander I, Pihko PM, Chem. Rev., 107(12), 5416, 2007
- Wolken WA, Have RT, Werf MJVD, J. Agric. Food Chem., 48, 5401, 2000
[Cited By]
참고문헌정보(참고문헌, 인용문헌)는 화학공학소재연구정보센터에 의해 제공되고 있습니다.