HSO3-functionalized Br?nsted acidic ionic liquids promote esterification of aromatic acid
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- 作者：FengYan Zhou (1) (2)
BingWei Xin (1)
JingCheng Hao (1) - 关键词：aromatic esters ; esterification ; aromatic acids ; alcohols ; ionic liquids
- 刊名：Chinese Science Bulletin
- 出版年：2013
- 出版时间：September 2013
- 年：2013
- 卷：58
- 期：26
- 页码：3202-3207
- 全文大小：728KB
- 参考文献：1. Larock R C. Comprehensive Organic Transformations. 2nd ed. New York: VCH, 1999
2. Arfela P M, Salmi T, Sundell M. et al. Comparison of polyvinylbenzene and polyolefin supported sulphonic acid catalysts in the esterification of acetic acid. Appl Catal A: Gen, 1999, 184: 25-2 CrossRef
3. Dijs I J, Ochten H L F, Walree C A, et al. Alkyl sulphonic acid surface-functionalised silica as heterogeneous acid catalyst in the solvent-free liquid-phase addition of acetic acid to camphene. J Mol Catal A: Chem, 2002, 188: 209-24 CrossRef
4. Gui J Z, Cong X H, Liu D, et al. Novel Br?nsted acidic ionic liquid as efficient and reusable catalyst system for esterification. Catal Comm, 2004, 5: 473-77 CrossRef
5. Welton T. Room-temperature ionic liquids. Chem Rev, 1999, 99: 2071-083 CrossRef
6. Dupont J. From molten salts to ionic liquids: A “Nano-journey. Acc Chem Res, 2011, 44: 1223-231 CrossRef
7. Angell C A, Byrne N, Belieres J. Parallel developments in aprotic and protic ionic liquids: Physical chemistry and applications. Acc Chem Res, 2007, 40: 1228-236 CrossRef
8. Zhou, L, Wang L. Chiral ionic liquid containing L-proline unit as a highly efficient and recyclable asymmetric organocatalyst for aldol reaction. Chem Lett, 2007, 36: 628-29 CrossRef
9. Wang J, Liu Z P. Ionic liquids as green reaction media for synthesis of poly(aryl ether ketone)s. Chin Sci Bull, 2013, 58: 1262-266 CrossRef
10. Yan C H, Wang L L, Gao H H. An efficient and recyclable iron(III)-containing imidazolium salt catalyst for cross-coupling of aryl Grignard reagents with alkyl halides. Chin Sci Bull, 2012, 57: 1953-958 CrossRef
11. Cole A C, Jensen J L, Ntai I, et al. Novel Br?nsted acidic ionic liquids and their use as dual solvent-catalysts. J Am Chem Soc, 2002, 124: 5962-963 CrossRef
12. Bates E D, Mayton R D, Ntai I, et al. CO2 capture by a task-specific ionic liquid. J Am Chem Soc, 2002, 124: 926-27 CrossRef
13. Dong Z Y, Yang Y, Zhang L F, et al. Inonic liquids containing the urea moiety for recognition of halides and complex anions. Chin Sci Bull, 2012, 57: 473-78 CrossRef
14. Zhang X Y, Fang S H, Zhang Z X, et al. Li/LiFePO4 battery performance with a guanidinium-based ionic liquid as the electrolyte. Chin Sci Bull, 2011, 56: 2906-910 CrossRef
15. Xing H B, Wang T, Zhou Z H, et al. Novel Br?nsted-acidic ionic liquids for esterifications. Ind Eng Chem Res, 2005, 44: 4147-150 CrossRef
16. Fang D, Zhou X L, Ye Z W, et al. Br?nsted acidic ionic liquids and their use as dual solvent-catalysts for Fischer esterifications. Ind Eng Chem Res, 2006, 45: 7982-984 CrossRef
17. Wang Y Y, Li W, Xu C, et al. Preparation and characterization of a novel benzimidazolium Br?nsted acid ionic liquid and its application in the synthesis of arylic esters. Chin J Chem, 2007, 25: 68-1 CrossRef
18. Xin B W, Zhang Y H, Liu L, et al. Water-promoted Suzuki reaction in room temperature ionic liquids. Synlett, 2005, (20): 3083-085
19. Xin B W, Zhang Y H, Cheng K. Phosphine-free Cross-Coupling reaction of arylboronic acids with carboxylic anhydrides or acyl chlorides in aqueous media. J Org Chem, 2006, 71: 5725-731 CrossRef
20. Xin B W, Zhang Y H, Cheng K. The surfactant-promoted cross-coupling reactions of arylboronic acids with carboxylic anhydrides or acyl chlorides in water. Synthesis, 2007, (13): 1970-978
21. Park S, Kazlauskas R J. Improved preparation and use of room-tem perature ionic liquids in lipase-catalyzed enantio- and regioselective acylations. J Org Chem, 2001, 66: 8395-401 CrossRef - 作者单位：FengYan Zhou (1) (2)
BingWei Xin (1)
JingCheng Hao (1)
1. Key Laboratory of Colloid and Interface, Ministry of Education, Shandong University, Jinan, 250100, China
2. Department of Chemistry, Zaozhuang College, Zaozhuang, 277160, China - ISSN：1861-9541
文摘
Esterification of aromatic acid can be promoted via HSO3-functionalized Br?nsted acidic ionic liquids (ILs). Under the optimum conditions, using 1-(3-sulfonic acid) propyl-3-methylimidazolium hydrogen sulfate ([MimC3SO3H][HSO4]) and 1-(4-sulfonic acid) butyl-3-methylimidazolium hydrogen sulfate ([MimC4SO3H][HSO4]) as dual solvent-catalysts, the conversion of esterification of aromatic acid was determined to be more than 90%, indicating that HSO3-functionalized ILs show much better catalytic ability than those of non-functionalized ionic liquids. The separation of desired product was easily performed by extraction with diethyl ether and these HSO3-functionalized ILs could be reused 7 times after vacuum drying. Our data represent an environmentally friendly method for the preparation of aromatic esters.