Articles & Issues
- Language
- English
- Conflict of Interest
- In relation to this article, we declare that there is no conflict of interest.
- Publication history
-
Received October 5, 2013
Accepted December 28, 2013
- This is an Open-Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/bync/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
Copyright © KIChE. All rights reserved.
All issues
Comparative catalytic activity of supported ZnBr2-containing ionic liquid catalysts for preparation of glycerol carbonate by glycerolysis of urea
School of Chemical and Biomolecular Engineering, Pusan National University, Busan 609-735, Korea
dwpark@pusan.ac.kr
Korean Journal of Chemical Engineering, June 2014, 31(6), 972-980(9), 10.1007/s11814-013-0296-0
Download PDF
Abstract
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.
References
Behr A, Enilting J, Irawadi K, Leschinski J, Lindner F, Green Chem., 10, 13 (2008)
Kovvali AS, Sirkar KK, Ind. Eng. Chem. Res., 41(9), 2287 (2002)
Rousseau J, Rousseau C, Tetrahedron, 65, 8571 (2009)
Selva M, Fabris M, Green Chem., 11, 1161 (2009)
Ghandi M, Mostashari A, Karegar M, Barzegar MJ, Am. Oil Chem. Soc., 84, 681 (2007)
Rokicki G, Rokoczy P, Parzuchowski P, Sobiecki M, Green Chem., 7, 529 (2005)
Mouloungui Z, Yoo JW, Gachen CA, Gaset A, EP 0739888 (1996)
Teles JH, Rieber N, Harder W, US 5359094 (1994)
Dibenedetto A, Pastore C, Aresta M, Catal. Today, 115(1-4), 88 (2006)
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)
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)
Leadbeater NE, Marco M, Chem. Rev., 102(10), 3217 (2002)
McNamara CA, Dixon MJ, Bradley M, Chem. Rev., 102(10), 3275 (2002)
Bhattacharyya S, Comb. Chem. High Throughput Screen., 3, 65 (2000)
Frenzel T, Solodenko W, Kirschning A, in: R. Buchmeiser (Ed.), Polymeric Materials in Organic Synthesis and Catalysis, Wiley-VCH, Weinheim, 201-240 (2003)
Guo Z, Xing R, Liu S, Zhong Z, Li P, Carbohydr. Polym., 73, 173 (2008)
Kresge CT, Leonowicz ME, Roth WJ, Vartuli JC, Beck JS, Nature, 359, 710 (1992)
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)
Kim DW, Park DW, J. Nanosci. Nanotechno., 14, 4632 (2014)
Kim DW, Park MS, Park GA, Lee SD, Selvaraj M, Park DW, Res. Chem. Intermed., 37, 1305 (2011)
Yu JI, Choi HJ, Selvaraj M, Park DW, React. Kinet. Mech. Catal., 102, 353 (2011)
Kathalikkattil AC, Tharun J, Roshan R, Soek R, Park DW, Appl. Catal. A. Gen., 447, 107 (2012)
Krishnan GR, Sreekurnar K, Appl. Catal. A: Gen., 353(1), 80 (2009)
Qi C, Ye J, Zeng W, Jiang H, Adv. Synth. Catal., 352, 1925 (2010)
Sun J, Cheng WG, Fan W, Wang YH, Meng ZY, Zhang SJ, Catal. Today, 148(3-4), 361 (2009)
Tharun J, Hwang YS, Roshan R, Ahn SH, Kathalikkattil AC, Park DW, Catal. Sci. Technol., 2, 1674 (2012)
Vallapa N, Wiarachai O, Thongchul N , Pan J, Tangpasuthadol V, Kiatkamjornwong S, Hoven VP, Carbohydr. Polym., 83, 868 (2011)
Niedermaier I, Kolbeck C, Taccardi N, Schulz PS, Li J, Drewello T, Wasserscheid P, Steinruck HP, Maier F, Chem. Phys. Chem., 13, 1725 (2012)
Abry S, Thibon A, Albela B, Delichere P, Banse F, Bonneviot L, New J. Chem., 33, 484 (2009)
Derouet D, Forgeard S, Brosse JC, Emery J, Buzare JY, J. Polym. Sci. A: Polym. Chem., 36(3), 437 (1998)
Silva SS, Santos MI, Coutinho OP, Mano JF, Reis RL, J. Mater. Sci. Mater. Med., 16, 575 (2005)
Kim DW, Park KA, Kim MJ, Kang DH, Yang JG, Park DW, Appl. Catal. A. Gen., 473, 31 (2014)
Kovvali AS, Sirkar KK, Ind. Eng. Chem. Res., 41(9), 2287 (2002)
Rousseau J, Rousseau C, Tetrahedron, 65, 8571 (2009)
Selva M, Fabris M, Green Chem., 11, 1161 (2009)
Ghandi M, Mostashari A, Karegar M, Barzegar MJ, Am. Oil Chem. Soc., 84, 681 (2007)
Rokicki G, Rokoczy P, Parzuchowski P, Sobiecki M, Green Chem., 7, 529 (2005)
Mouloungui Z, Yoo JW, Gachen CA, Gaset A, EP 0739888 (1996)
Teles JH, Rieber N, Harder W, US 5359094 (1994)
Dibenedetto A, Pastore C, Aresta M, Catal. Today, 115(1-4), 88 (2006)
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)
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)
Leadbeater NE, Marco M, Chem. Rev., 102(10), 3217 (2002)
McNamara CA, Dixon MJ, Bradley M, Chem. Rev., 102(10), 3275 (2002)
Bhattacharyya S, Comb. Chem. High Throughput Screen., 3, 65 (2000)
Frenzel T, Solodenko W, Kirschning A, in: R. Buchmeiser (Ed.), Polymeric Materials in Organic Synthesis and Catalysis, Wiley-VCH, Weinheim, 201-240 (2003)
Guo Z, Xing R, Liu S, Zhong Z, Li P, Carbohydr. Polym., 73, 173 (2008)
Kresge CT, Leonowicz ME, Roth WJ, Vartuli JC, Beck JS, Nature, 359, 710 (1992)
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)
Kim DW, Park DW, J. Nanosci. Nanotechno., 14, 4632 (2014)
Kim DW, Park MS, Park GA, Lee SD, Selvaraj M, Park DW, Res. Chem. Intermed., 37, 1305 (2011)
Yu JI, Choi HJ, Selvaraj M, Park DW, React. Kinet. Mech. Catal., 102, 353 (2011)
Kathalikkattil AC, Tharun J, Roshan R, Soek R, Park DW, Appl. Catal. A. Gen., 447, 107 (2012)
Krishnan GR, Sreekurnar K, Appl. Catal. A: Gen., 353(1), 80 (2009)
Qi C, Ye J, Zeng W, Jiang H, Adv. Synth. Catal., 352, 1925 (2010)
Sun J, Cheng WG, Fan W, Wang YH, Meng ZY, Zhang SJ, Catal. Today, 148(3-4), 361 (2009)
Tharun J, Hwang YS, Roshan R, Ahn SH, Kathalikkattil AC, Park DW, Catal. Sci. Technol., 2, 1674 (2012)
Vallapa N, Wiarachai O, Thongchul N , Pan J, Tangpasuthadol V, Kiatkamjornwong S, Hoven VP, Carbohydr. Polym., 83, 868 (2011)
Niedermaier I, Kolbeck C, Taccardi N, Schulz PS, Li J, Drewello T, Wasserscheid P, Steinruck HP, Maier F, Chem. Phys. Chem., 13, 1725 (2012)
Abry S, Thibon A, Albela B, Delichere P, Banse F, Bonneviot L, New J. Chem., 33, 484 (2009)
Derouet D, Forgeard S, Brosse JC, Emery J, Buzare JY, J. Polym. Sci. A: Polym. Chem., 36(3), 437 (1998)
Silva SS, Santos MI, Coutinho OP, Mano JF, Reis RL, J. Mater. Sci. Mater. Med., 16, 575 (2005)
Kim DW, Park KA, Kim MJ, Kang DH, Yang JG, Park DW, Appl. Catal. A. Gen., 473, 31 (2014)