Transesterification of Glycerol with Dimethyl Carbonate to Glycerol Carbonate over Na-Based Zeolites

doi:10.1016/S1872-2067(11)60450-6

Abstract

Abstract: Glycerol carbonate (GC) was synthesized via transesterification of glycerol with dimethyl carbonate under mild conditions over a series of base zeolites. It was found that the NaY zeolite exhibited a higher selectivity for GC (100%) than heterogeneous bases (such as CaO and SrO) or homogeneous catalysts (such as NaOH and K₂CO₃). Further experiments over different base zeolites disclosed that this transesterification reaction depended strongly on catalyst structure. Base zeolites with small pore diameter such as 3A, 4A, and NaZSM-5 were inactive, while NaY and Naβ with larger pore diameter exhibited excellent GC yields under mild conditions.

Key words: glycerol carbonate, glycerol, dimethyl carbonate, zeolite, NaY, transesterification

PAN Sai-Yong, ZHENG Li-Ping, NIE Ren-Feng, XIA Shui-Xin, CHEN Ping, HOU Zhao-Yin. Transesterification of Glycerol with Dimethyl Carbonate to Glycerol Carbonate over Na-Based Zeolites[J]. Chinese Journal of Catalysis, 2012, 33(11): 1772-1777.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(11)60450-6

https://www.cjcatal.com/EN/Y2012/V33/I11/1772

References

1 Dodds D R, Gross R A. Science, 2007, 318: 1250
2 Huber G W, Iborra S, Corma A. Chem Rev, 2006, 106: 4044
3 Pagliaro M, Ciriminna R, Kimura H, Rossi M, Della Pina C. Angew Chem, Int Ed, 2007, 46: 4434
4 Zhou C H, Beltramini J N, Fan Y X, Lu G Q. Chem Soc Rev, 2008, 37: 527
5 Sabourin-Provost G, Hallenbeck P C. Bioresource Technol, 2009, 100: 3513
6 Yuan Z L, Wang J H, Wang L, Xie W H, Chen P, Hou Z Y, Zheng X M. Bioresource Technol, 2010, 101: 7088
7 Zope B N, Hibbitts D D, Neurock M, Davis R J. Science, 2010, 330: 74
8 Liang D, Gao J, Sun H, Chen P, Hou Z, Zheng X. Appl Catal B, 2011, 106: 423
9 Yuan Z L, Xia S X, Chen P, Hou Z Y, Zheng X M. Energy Fu-els, 2011, 25: 3186
10 Melero J A, Vicente G, Paniagua M, Morales G, Muñoz P. Bioresource Technol, 2011, 103: 142
11 Corma A, Abd Hamid S B, Iborra S, Velty A. J Catal, 2005, 234: 340
12 Behr A, Eilting J, Irawadi K, Leschinski J, Lindner F. Green Chem, 2008, 10: 13
13 Schaffner B, Schaffner F, Verevkin S P, Borner A. Chem Rev, 2010, 110: 4554
14 Bozell J J, Petersen G R. Green Chem, 2010, 12: 539
15 Shaikh A A G, Sivaram S. Chem Rev, 1996, 96: 951
16 George J, Patel Y, Pillai S M, Munshi P. J Mol Catal A, 2009, 304: 1
17 Vieville C, Yoo J W, Pelet S, Mouloungui Z. Catal Lett, 1998, 56: 245
18 Aresta M, Dibenedetto A, Nocito F, Pastore C. J Mol Catal A, 2006, 257: 149
19 Climent M J, Corma A, De Frutos P, Iborra S, Noy M, Velty A, Concepcion P. J Catal, 2010, 269: 140
20 Aresta M, Dibenedetto A, Nocito F, Ferragina C. J Catal, 2009, 268: 106
21 Wang L G, Ma Y B, Wang Y, Liu S M, Deng Y Q. Catal Commun, 2011, 12: 1458
22 Hammond C, Lopez-Sanchez J A, Ab Rahim M H, Dimitratos N, Jenkins R L, Carley A F, He Q, Kiely C J, Knight D W, Hutchings G J. Dalton Trans, 2011, 40: 3927
23 Hu J L, Li J J, Gu Y L, Guan Z H, Mo W L, Ni Y M, Li T, Li G X. Appl Catal A, 2010, 386: 188
24 Mizuno T, Nakai T, Mihara M. Heteroatom Chem, 2010, 21: 541
25 Cho H J, Kwon H M, Tharun J, Park D W. J Ind Eng Chem, 2010, 16: 679
26 Alvarez M G, Segarra A M, Contreras S, Sueiras J E, Medina F, Figueras F. Chem Eng J, 2010, 161: 340
27 Álvarez M G, Plíšková M, Segarra A M, Medina F, Figueras F. Appl Catal B, 2012, 113-114: 212
28 Gordillo A, Lloyd-Jones G C. Chem Eur J, 2012, 18: 2660
29 Zhang X, Wei H. J Nat Gas Chem, 2011, 20: 299
30 范燕平, 王庆印, 杨先贵, 姚洁, 王公应. 催化学报 (Fan Y P, Wang Q Y, Yang X G, Yao J, Wang G Y. Chin J Catal), 2010, 31: 38
31 Rokicki G, Rakoczy P, Parzuchowski P, Sobiecki M. Green Chem, 2005, 7: 529
32 Kim S C, Kim Y H, Lee H, Yoon D Y, Song B K. J Mol Catal B, 2007, 49: 75
33 Naik P U, Petitjean L, Refes K, Picquet M, Plasseraud L. Adv Synth Catal, 2009, 351: 1753
34 Ochoa-Gomez J R, Gomez-Jimenez-Aberasturi O, Maestro- Madurga B, Pesquera-Rodriguez A, Ramirez-Lopez C, Lorenzo-Ibarreta L, Torrecilla-Soria J, Villaran-Velasco M C. Appl Catal A, 2009, 366: 315
35 Simanjuntak F S H, Kim T K, Lee S D, Ahn B S, Kim H S, Lee H. Appl Catal A, 2011, 401: 220
36 Malyaadri M, Jagadeeswaraiah K, Prasad P S S, Lingaiah N. Appl Catal A, 2011, 401: 153
37 Takagaki A, Iwatani K, Nishimura S, Ebitani K. Green Chem, 2010, 12: 578
38 Xia S X, Yuan Z L, Wang L, Chen P, Hou Z Y. Appl Catal A, 2011, 403: 173
39 Yuan Z, Wang L, Wang J, Xia S, Chen P, Hou Z, Zheng X. Appl Catal B, 2011, 101: 431
40 Busca G. Chem Rev, 2010, 110: 2217
41 Gao J, Guo J Z, Liang D, Hou Z Y, Fei J H, Zheng X M. Int J Hydrog Energy, 2008, 33: 5493
42 Zhu J H, Chun Y, Qin Y, Xu Q H. Microporous Mesoporous Mater, 1998, 24: 19
43 Maris E P, Davis R J. J Catal, 2007, 249: 328
44 Lahr D G, Shanks B H. Ind Eng Chem Res, 2003, 42: 5467
45 Levchenko A A, Jain P, Trofymluk O, Yu P, Navrotsky A, Sen S. J Phys Chem B, 2010, 114: 3070

[1]	Lu Cheng, Xuning Chen, P. Hu, Xiao-Ming Cao. Advantages and limitations of hydrogen peroxide for direct oxidation of methane to methanol at mono-copper active sites in Cu-exchanged zeolites [J]. Chinese Journal of Catalysis, 2023, 51(8): 135-144.
[2]	Duozheng Ma, Xiangcheng Li, Chuang Liu, Caroline Versluis, Yingchun Ye, Zhendong Wang, Eelco T. C. Vogt, Bert M. Weckhuysen, Weimin Yang. SCM-36 zeolite nanosheets applied in the production of renewable p-xylene from ethylene and 2,5-dimethylfuran [J]. Chinese Journal of Catalysis, 2023, 47(4): 200-213.
[3]	Runze Liu, Xue Shao, Chang Wang, Weili Dai, Naijia Guan. Reaction mechanism of methanol-to-hydrocarbons conversion: Fundamental and application [J]. Chinese Journal of Catalysis, 2023, 47(4): 67-92.
[4]	Changcheng Wei, Wenna Zhang, Kuo Yang, Xiu Bai, Shutao Xu, Jinzhe Li, Zhongmin Liu. An efficient way to use CO₂ as chemical feedstock by coupling with alkanes [J]. Chinese Journal of Catalysis, 2023, 47(4): 138-149.
[5]	Longkang Zhang, Yue Ma, Changcheng Liu, Zhipeng Wan, Chengwei Zhai, Xin Wang, Hao Xu, Yejun Guan, Peng Wu. Demetallation and reduction induced ultra-dispersed PtZn alloy confined in zeolite for propane dehydrogenation [J]. Chinese Journal of Catalysis, 2023, 55(12): 241-252.
[6]	Peerapol Pornsetmetakul, Ferdy J. A. G. Coumans, Rim C. J. van de Poll, Anna Liutkova, Duangkamon Suttipat, Brahim Mezari, Chularat Wattanakit, Emiel J. M. Hensen. Post-synthesis metal (Sn, Zr, Hf) modification of BEA zeolite: Combined Lewis and Brønsted acidity for cascade catalysis [J]. Chinese Journal of Catalysis, 2023, 55(12): 200-215.
[7]	Kai Shi, Di Si, Xue Teng, Lisong Chen, Jianlin Shi. Enhanced electrocatalytic glycerol oxidation on CuCoN_0.6/CP at significantly reduced potentials [J]. Chinese Journal of Catalysis, 2023, 53(10): 143-152.
[8]	Chuncheng Liu, Evgeny A. Uslamin, Sophie H. van Vreeswijk, Irina Yarulina, Swapna Ganapathy, Bert M. Weckhuysen, Freek Kapteijn, Evgeny A. Pidko. An integrated approach to the key parameters in methanol-to-olefins reaction catalyzed by MFI/MEL zeolite materials [J]. Chinese Journal of Catalysis, 2022, 43(7): 1879-1893.
[9]	Wenhao Cui, Dali Zhu, Juan Tan, Nan Chen, Dong Fan, Juan Wang, Jingfeng Han, Linying Wang, Peng Tian, Zhongmin Liu. Synthesis of mesoporous high-silica zeolite Y and their catalytic cracking performance [J]. Chinese Journal of Catalysis, 2022, 43(7): 1945-1954.
[10]	Jianxiang Wu, Xuejing Yang, Ming Gong. Recent advances in glycerol valorization via electrooxidation: Catalyst, mechanism and device [J]. Chinese Journal of Catalysis, 2022, 43(12): 2966-2986.
[11]	Kaipeng Cao, Dong Fan, Shu Zeng, Benhan Fan, Nan Chen, Mingbin Gao, Dali Zhu, Linying Wang, Peng Tian, Zhongmin Liu. Organic-free synthesis of MOR nanoassemblies with excellent DME carbonylation performance [J]. Chinese Journal of Catalysis, 2021, 42(9): 1468-1477.
[12]	Qifeng Lei, Chang Wang, Weili Dai, Guangjun Wu, Naijia Guan, Michael Hunger, Landong Li. Tandem Lewis acid catalysis for the conversion of alkenes to 1,2-diols in the confined space of bifunctional TiSn-Beta zeolite [J]. Chinese Journal of Catalysis, 2021, 42(7): 1176-1184.
[13]	Sen Wang, Zhikai Li, Zhangfeng Qin, Mei Dong, Junfen Li, Weibin Fan, Jianguo Wang. Catalytic roles of the acid sites in different pore channels of H-ZSM-5 zeolite for methanol-to-olefins conversion [J]. Chinese Journal of Catalysis, 2021, 42(7): 1126-1136.
[14]	Xiaoling Liu, Lei Chen, Hongzhong Xu, Shi Jiang, Yu Zhou, Jun Wang. Straightforward synthesis of beta zeolite encapsulated Pt nanoparticles for the transformation of 5-hydroxymethyl furfural into 2,5-furandicarboxylic acid [J]. Chinese Journal of Catalysis, 2021, 42(6): 994-1003.
[15]	Huimin Luan, Chi Lei, Ye Ma, Qinming Wu, Longfeng Zhu, Hao Xu, Shichao Han, Qiuyan Zhu, Xiaolong Liu, Xiangju Meng, Feng-Shou Xiao. Alcohol-assisted synthesis of high-silica zeolites in the absence of organic structure-directing agents [J]. Chinese Journal of Catalysis, 2021, 42(4): 563-570.