碱性离子液体催化甘油合成1,2-甘油碳酸酯

doi:10.1016/S1872-2067(14)60036-X

催化学报 ›› 2014, Vol. 35 ›› Issue (5): 757-762.DOI: 10.1016/S1872-2067(14)60036-X

碱性离子液体催化甘油合成1,2-甘油碳酸酯

易宇轩^a, 申越^a, 孙建奎^a, 王波^a, 许凤^a, 孙润仓^a,b

a 北京林业大学材料科学与技术学院, 林木生物质化学北京市重点实验室, 北京100083;
b 华南理工大学制浆造纸工程国家重点实验室, 广东广州510640

收稿日期:2013-11-14 修回日期:2014-01-03 出版日期:2014-04-18 发布日期:2014-04-24
通讯作者: 王波
基金资助:
十二五国家科技计划项目（2012BAD32B06）；中央高校基本科研业务费专项资金（TD2011-11）；国家自然科学基金（31170556）；教育部新世纪优秀人才支持（NCET-13-0671）；北京高等学校“青年英才计划”（YETP0765）；中国博士后科学基金（2012T50051）；国家重点基础研究发展计划（973计划，2010CB732204）.

Basic ionic liquids promoted the synthesis of glycerol 1,2-carbonate from glycerol

YuxuanYi^a, Yue Shen^a, Jiankui Sun^a, Bo Wang^a, Feng Xu^a, Runcang Sun^a,b

a Beijing Key Laboratory of Lignocellulosic Chemistry, College of Materials Science and Technology, Beijing Forestry University, Beijing 100083, China;
b State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510640, Guangdong, China

Received:2013-11-14 Revised:2014-01-03 Online:2014-04-18 Published:2014-04-24
Supported by:
This work was supported by the National Science and Technology Program of the Twelfth Five-Year Plan Period (2012BAD32B06), Fundamental Research Funds for the Central Universities (TD2011-11), the National Natural Science Foundation of China (31170556), New Century Excellent Talents in University (NCET-13-0671), Beijing Higher Education Young Elite Teacher Project (YETP0765), China Postdoctoral Science Special Foundation (2012T50051), and the National Basic Research Program of China (973 Program, 2010CB732204).

摘要/Abstract

摘要：

以离子液体为催化剂，在无溶剂体系中，考察了生物质平台化合物甘油转化1，2-甘油碳酸酯的反应. 与酸性离子液体和常用无机碱性催化剂相比，碱性离子液体咪唑基1-丁基-3-甲基咪唑（[Bmim]Im）、氢氧化1-丁基-3-甲基咪唑（[Bmim]OH）、咪唑基1-烯丙基-3-甲基咪唑（[Amim]Im）、氢氧化1-烯丙基-3-甲基咪唑（[Amim]OH）在甘油与碳酸二甲酯的酯交换反应中表现出优异的活性. 其中，以[Bmim]Im离子液体为催化剂时甘油转化率为98.4%和甘油碳酸酯选择性接近100%. 另外，该离子液体可以回收重复利用3次后甘油转化率仍可达92%，甘油碳酸酯选择性可近100%. 此碱性离子液体催化方法具有反应结果较好、产物分离简单、条件温和以及环境友好等特点.

关键词: 酯交换, 甘油, 甘油碳酸酯, 碱性离子液体, 二烷基碳酸酯, 平台化合物

Abstract:

Glycerol has been subjected to a transesterification process with dialkyl carbonate to generate glycerol 1,2-carbonate (GC) using different ionic liquids as catalysts under solvent-free conditions. The basic ionic liquids 1-butyl-3-methylimidazolium imidazolium ([Bmim]Im), 1-butyl-3-methylimidazolium hydroxide ([Bmim]OH), 1-allyl-3-methylimidazolium imidazolium ([Amim]Im), and 1-allyl-3-methylimidazolium hydroxide ([Amim]OH) worked well as catalysts compared with acidic ionic liquid and inorganic basic catalysts. Subsequent optimization of the reaction conditions using [Bmim]Im as a catalyst led to 98.4% glycerol conversion and up to 100% GC selectivity at 70 ℃ under ambient pressure. The recovery and reuse of these ionic liquids were also satisfactory. [Bmim]Im could be reused three times (i.e., 92.0% glycerol conversion and near 100% GC selectivity). This method exhibited several special features including a simple product isolation procedure, high product yield, exclusive selectivity, and mild conditions, as well as avoiding the use of any toxic catalysts.

Key words: Transesterification, Glycerol, Glycerol carbonate, Basic ionic liquid, Dialkyl carbonate, Platform chemcial

易宇轩, 申越, 孙建奎, 王波, 许凤, 孙润仓. 碱性离子液体催化甘油合成1,2-甘油碳酸酯[J]. 催化学报, 2014, 35(5): 757-762.

YuxuanYi, Yue Shen, Jiankui Sun, Bo Wang, Feng Xu, Runcang Sun. Basic ionic liquids promoted the synthesis of glycerol 1,2-carbonate from glycerol[J]. Chinese Journal of Catalysis, 2014, 35(5): 757-762.

×
扫码分享

导出引用管理器 EndNote|Ris|BibTeX

链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(14)60036-X

https://www.cjcatal.com/CN/Y2014/V35/I5/757

参考文献

[1] Corma A, Iborra S, Velty A. Chem Rev, 2007, 107: 2411
[2] Basha S A, Gopal K R, Jebaraj S. Renew Sust Energ Rev, 2009, 13: 1628
[3] Huber G W, Iborra S, Corma A. Chem Rev, 2006, 106: 4044
[4] Leung D Y C, Wu X, Leung M K H. Appl Energ, 2010, 87: 1083
[5] Zhang X Y, Ma Q, Cheng B B, Wang J, Li J S, Nie F D. J Nat Gas Chem, 2012, 21: 774
[6] Behr A, Eilting J, Irawadi K, Leschinski J, Lindner F. Green Chem, 2008, 10: 13
[7] Zheng Y G, Chen X L, Shen Y C. Chem Rev, 2008, 108: 5253
[8] Wang L, Liu Q, Zhou M H, Xiao G M. J Nat Gas Chem, 2012, 21: 25
[9] Pagliaro M, Ciriminna R, Kimura H, Rossi M, Della Pina C. Angew Chem Int Ed, 2007, 46: 4434
[10] Xia S X, Nie R F, Lu X Y, Wang L N, Chen P, Hou Z Y. J Catal, 2012, 296: 1
[11] Zhang M Y, Liang D, Nie R F, Lu X Y, Chen P, Hou Z Y. Chin J Catal (张梦媛, 梁丹, 聂仁峰, 吕秀阳, 陈平, 侯昭胤. 催化学报), 2012, 33: 1340
[12] Kovvali A S, Sirkar K K. Ind Eng Chem Res, 2002, 41: 2287
[13] Randall D, De Vos R. EP Patent 419114. 1991
[14] Plasman V, Caulier T, Boulos N. Plast Addit Compd, 2005, 7(2): 30
[15] Weuthen M, Hees U. DE Patent 4335947. 1995
[16] Rousseau J, Rousseau C, Lynikaite B, Sackus A, de Leon C, Rollin P, Tatibouët A. Tetrahedron, 2009, 65: 8571
[17] Chen C H, Hyung Y E, Vissers D R, Amine K. US Patent 2000157413 A1. 2003
[18] Ochoa-Gómez J R, Gómez-Jiménez-Aberasturi O, Ramírez-López C, Belsue M. Org Process Res Dev, 2012, 16: 389
[19] Sonnati M O, Amigoni S, Taffin de Givenchy E P, Darmanin T, Choulet O, Guittard F. Green Chem, 2013, 15: 283
[20] Zhou C H, Beltramini J N, Fan Y X, Lu G Q. Chem Soc Rev, 2008, 37: 527
[21] Alvarez M G, Segarra A M, Contreras S, Sueiras J E, Medina F, Figueras F. Chem Eng J, 2010, 161: 340
[22] Rokicki G, Rakoczy P, Parzuchowski P, Sobiecki M. Green Chem, 2005, 7: 529
[23] Li J B, Wang T. J Chem Thermodyn, 2011, 43: 731
[24] Li J B, Wang T. React Kinet, Mech Catal, 2011, 102: 113
[25] Du M M, Li Q X, Dong W T, Geng T, Jiang Y J. Res Chem Intermed, 2012, 38: 1069
[26] Takagaki A, Iwatani K, Nishimura S, Ebitani K. Green Chem, 2010, 12: 578
[27] Bai R X, Wang S, Mei F M, Li T, Li G X. J Ind Eng Chem, 2011, 17: 777
[28] Malyaadri M, Jagadeeswaraiah K, Sai Prasad P S, Lingaiah N. Appl Catal A, 2011, 401: 153
[29] Pan S Y, Zheng L P, Nie R F, Xia S X, Chen P, Hou Z Y. Chin J Catal (潘赛勇, 郑丽萍, 聂仁峰, 夏水鑫, 陈平, 侯昭胤. 催化学报), 2012, 33: 1772
[30] Ochoa-Gómez J R, Gómez-Jiménez-Aberasturi O, Ramírez-López C, Maestro-Madurga B. Green Chem, 2012, 14: 3368
[31] Aresta M, Dibenedetto A, Nocito F, Pastore C. J Mol Catal A, 2006, 257: 149
[32] Tudorache M, Protesescu L, Coman S, Parvulescu V I. Green Chem, 2012, 14: 478
[33] Lee K H, Park C H, Lee E Y. Bioprocess Biosyst Eng, 2010, 33: 1059
[34] Tudorache M, Protesescu L, Negoi A, Parvulescu V I. Appl Catal A, 2012, 437-438: 90
[35] Chiappe C, Rajamani S, Iapac C. Pure Appl Chem, 2012, 84: 755
[36] Naik P U, Petitjean L, Refes K, Picquet M, Plasseraud L. Adv Synth Catal, 2009, 351: 1753
[37] Tan S S Y, MacFarlane D R. Top Curr Chem, 2009, 290: 311
[38] Yoshizawa M, Hirao M, Ito-Akita K, Ohno H. J Mater Chem, 2001, 11: 1057
[39] Ochoa-Gómez J R, Gómez-Jiménez-Aberasturi O, Maestro-Madurga B, Pesquera-Rodríguez A, Ramírez-López C, Lorenzo-Ibarreta L, Torrecilla-Soria J, Villarán-Velasco M C. Appl Catal A, 2009, 336: 315
[40] Lin L Z, Yamaguchi H, Suzuki A. RSC Adv, 2013, 3: 14379
[41] Simanjuntak F S H, Kim T K, Lee S D, Ahn B S, Kim H S, Lee H. Appl Catal A, 2011, 401: 220
[42] Ochoa-Gómez J R, Gómez-Jiménez-Aberasturi O, Ramírez-López C A, Nieto-Mestre J, Maestro-Madurga B, Belsué M. Chem Eng J, 2011, 175: 505

碱性离子液体催化甘油合成1,2-甘油碳酸酯

Basic ionic liquids promoted the synthesis of glycerol 1,2-carbonate from glycerol

PDF

可视化

被引次数

摘要/Abstract

引用本文

使用本文

扫码分享

参考文献

相关文章 15

编辑推荐

Metrics

[1]	师凯, 司娣, 滕雪, 陈立松, 施剑林. 用于高效电催化甘油氧化的CuCoN_0.6/CP催化剂[J]. 催化学报, 2023, 53(10): 143-152.
[2]	吴建祥, 杨雪晶, 龚鸣. 甘油电催化氧化的研究进展：催化剂、机理和应用[J]. 催化学报, 2022, 43(12): 2966-2986.
[3]	Steffen Cychy, Sebastian Lechler, Zijian Huang, Michael Braun, Ann Cathrin Brix, Peter Blümler, Corina Andronescu, Friederike Schmid, Wolfgang Schuhmann, Martin Muhler. 甘油氧化的光谱电化学傅里叶变换衰减全反射谱红外光谱薄膜流动池中硼酸镍层厚度的优化[J]. 催化学报, 2021, 42(12): 2206-2215.
[4]	姜媛媛, 周茹茹, 赵怀远, 叶柏镛, 龙奕华, 王正宝, 侯昭胤. 有机-无机复合型固体酸催化剂的制备及其催化甘油乙酸甲酯酯交换反应[J]. 催化学报, 2021, 42(10): 1772-1781.
[5]	王佳, 杨曼, 王爱琴. Pt-W催化剂上甘油选择性氢解制备1,3-丙二醇研究进展[J]. 催化学报, 2020, 41(9): 1311-1319.
[6]	雷念, 苗治理, 刘菲, 王华, 潘晓丽, 王爱琴, 张涛. 甘油氢解反应中Pt/WO₃/Al₂O₃催化剂的失活行为[J]. 催化学报, 2020, 41(8): 1261-1267.
[7]	杨丽华, 何天衢, 赖楚钧, 陈平, 侯昭胤. 氮掺杂碳负载Sb@PtSb₂催化剂的制备及其在甘油选择性氧化反应中的应用[J]. 催化学报, 2020, 41(3): 494-502.
[8]	杨丽华, 黎学文, 陈平, 侯昭胤. 无碱溶液中的甘油选择性氧化:简短的综述[J]. 催化学报, 2019, 40(7): 1020-1034.
[9]	孔康, 李迪帆, 马文保, 周青青, 唐国平, 侯震山. Al(CF₃SO₃)₃催化选择性氧化甘油转化为甲酸[J]. 催化学报, 2019, 40(4): 534-542.
[10]	杨超军, 张帆, 雷念, 杨曼, 刘菲, 苗治理, 孙永南, 赵晓晨, 王爱琴. Au促进Pt/WO₃催化甘油氢解制1,3-丙二醇[J]. 催化学报, 2018, 39(8): 1366-1372.
[11]	李闯, 何博, 凌雨, 曾志荣, 梁长海. Zr-Al复合氧化物负载Pt催化甘油氢解制正丙醇[J]. 催化学报, 2018, 39(6): 1121-1128.
[12]	杨曼, 赵晓晨, 任煜京, 王佳, 雷念, 王爱琴, 张涛. Pt/Nb-WO_x催化甘油选择氢解制1,3-丙二醇:Nb掺杂抑制WO_x的过度还原[J]. 催化学报, 2018, 39(6): 1027-1037.
[13]	杜洪仪, 陈飔, 王恒伟, 路军岭. 酸性Al₂O₃层包裹Pt纳米颗粒:增强的金属-酸性双功能协同效应提高其甘油氢解反应催化性能[J]. 催化学报, 2017, 38(7): 1237-1244.
[14]	俞卫华, 王朋朋, 周春晖, 赵汉彬, 童东绅, 张浩, 杨慧敏, 季生福, 王浩. 催化甘油脱水反应的酸活化蒙脱石负载WO_x催化剂的研究[J]. 催化学报, 2017, 38(6): 1087-1100.
[15]	张晨, 王涛, 丁云杰. Pb-Pt/AC催化甘油一步法制备丙酮酸[J]. 催化学报, 2017, 38(5): 928-938.