Comparative catalytic activity of supported ZnBr2-containing ionic liquid catalysts for preparation of glycerol carbonate by glycerolysis of urea

Dong-Woo Kim; Min-Ji Kim; Kuruppathparambil Roshith; Moon-Il Kim; Joo-Young Kwak; Dae-Won Park

Korean Journal of Chemical Engineering, Vol.31, No.6, 972-980, June, 2014

DOI10.1007/s11814-013-0296-0 Export Citation

Comparative catalytic activity of supported ZnBr2-containing ionic liquid catalysts for preparation of glycerol carbonate by glycerolysis of urea

Dong-Woo Kim, Min-Ji Kim, Kuruppathparambil Roshith, Moon-Il Kim, Joo-Young Kwak, and Dae-Won Park^†

School of Chemical and Biomolecular Engineering, Pusan National University, Busan 609-735, Korea

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The synthesis of glycerol carbonate by glycerolysis of urea was investigated under mild conditions, using immobilized metal-containing ionic liquid catalysts. Three different catalysts were prepared, with the following supports: (1) polystyrene (PS), (2) commercial silica (CS), and (3) chitosan (CH). The glycerolysis of urea was considered to include two main reactions: carbamoylation of glycerol and carbonylation of glycerol carbamate. The approximate rate constant for PS-(Im)2ZnBr2 was higher than those of CH-(Im)2ZnBr2 and CS-(Im)2ZnBr2 probably due to its wellbalanced acid-base properties. The activation energies for PS-, CH-, and CS-(Im)2ZnBr2 were 142.9, 163.0, and 166.7 kJ mol^(-1), respectively. PS-(Im)2ZnBr2 exhibited better reuse properties than CH-(Im)2ZnBr2 and CS-(Im)2ZnBr2 catalysts.

Keywords:Glycerol Carbonate;Glycerol;Urea;Supported Catalyst;Ionic Liquid

[References]

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Li QB, Zhang WY, Zhao N, Wei W, Sun YH, Catal. Today, 115(1-4), 111 (2006)
Okutsu M, Kitsuki T, JP 039347 (2007)
Aresta M, Dubois JL, Dibenedetto A, Nocito F, Ferragina C, EP 08305653.1 (2008)
Sasa T, Okutsu M, Uno M, JP 067689 (2009)
Okutsu M, Kitsuki T, JP 050415 (2000)
Fujita S, Yamanishi Y, Arai M, J. Catal., 297, 137 (2013)
Aresta M, Dibenedetto A, Nocito F, Ferragina C, J. Catal., 268(1), 106 (2009)
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Shim HL, Udayakumar S, Yu JI, Kim I, Park DW, Catal. Today, 148(3-4), 350 (2009)
Han L, Li H, Choi SJ, Park MS, Lee SM, Kim YJ, Park DW, Appl. Catal. A Gen., 429, 67 (2012)
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Kim DW, Park KA, Kim MJ, Kang DH, Yang JG, Park DW, Appl. Catal. A. Gen., 473, 31 (2014)

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[2] Kovvali AS, Sirkar KK, Ind. Eng. Chem. Res., 41(9), 2287 (2002)

[3] Rousseau J, Rousseau C, Tetrahedron, 65, 8571 (2009)

[4] Selva M, Fabris M, Green Chem., 11, 1161 (2009)

[5] Ghandi M, Mostashari A, Karegar M, Barzegar MJ, Am. Oil Chem. Soc., 84, 681 (2007)

[6] Rokicki G, Rokoczy P, Parzuchowski P, Sobiecki M, Green Chem., 7, 529 (2005)

[7] Mouloungui Z, Yoo JW, Gachen CA, Gaset A, EP 0739888 (1996)

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[9] Dibenedetto A, Pastore C, Aresta M, Catal. Today, 115(1-4), 88 (2006)

[10] Li QB, Zhang WY, Zhao N, Wei W, Sun YH, Catal. Today, 115(1-4), 111 (2006)

[11] Okutsu M, Kitsuki T, JP 039347 (2007)

[12] Aresta M, Dubois JL, Dibenedetto A, Nocito F, Ferragina C, EP 08305653.1 (2008)

[13] Sasa T, Okutsu M, Uno M, JP 067689 (2009)

[14] Okutsu M, Kitsuki T, JP 050415 (2000)

[15] Fujita S, Yamanishi Y, Arai M, J. Catal., 297, 137 (2013)

[16] Aresta M, Dibenedetto A, Nocito F, Ferragina C, J. Catal., 268(1), 106 (2009)

[17] Hammond C, Sanchez JAL, Rahim MHA, Dimitratos N, Jenkins RL, Carley AF, He Q, Kiely CJ, Knight DW, Hutchings GJ, Dalton Trans., 40, 3927 (2011)

[18] Leadbeater NE, Marco M, Chem. Rev., 102(10), 3217 (2002)

[19] McNamara CA, Dixon MJ, Bradley M, Chem. Rev., 102(10), 3275 (2002)

[20] Bhattacharyya S, Comb. Chem. High Throughput Screen., 3, 65 (2000)

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[22] Guo Z, Xing R, Liu S, Zhong Z, Li P, Carbohydr. Polym., 73, 173 (2008)

[23] Kresge CT, Leonowicz ME, Roth WJ, Vartuli JC, Beck JS, Nature, 359, 710 (1992)

[24] Shim HL, Udayakumar S, Yu JI, Kim I, Park DW, Catal. Today, 148(3-4), 350 (2009)

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[28] Yu JI, Choi HJ, Selvaraj M, Park DW, React. Kinet. Mech. Catal., 102, 353 (2011)

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