Synthesis and Catalytic Activity of Novel Heternuclear Dication Brønsted Acidic Ionic Liquids

doi:10.6023/cjoc201409040

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (4): 890-897.DOI: 10.6023/cjoc201409040 Previous Articles Next Articles

Notes

新型异核双阳离子型磺酸功能化离子液体的合成及其催化活性

崔文辉^a,b, 张有明^b, 贾如琰^a, 王昱^a, 魏太保^,b

a 陇南师范高等专科学校生化系成县 742500;
b 西北师范大学化学化工学院教育部生态环境相关材料重点实验室甘肃省高分子材料重点实验室兰州 730070

收稿日期:2014-09-24 修回日期:2014-12-01 发布日期:2015-01-06
通讯作者: 崔文辉 E-mail:cwh0939@126.com
基金资助:
甘肃省自然科学基金(No. 1107RJZK243)资助项目.

Synthesis and Catalytic Activity of Novel Heternuclear Dication Brønsted Acidic Ionic Liquids

Cui Wenhui^a,b, Zhang Youming^b, Jia Ruyan^a, Wang Yu^a, Wei Taibao^,b

a Department of Biology & Chemistry, Longnan Normal College, Chengxian 742500;
b Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education of China, Key Laboratory of Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received:2014-09-24 Revised:2014-12-01 Published:2015-01-06
Supported by:
Project supported by the Natural Science Foundation of Gansu Province (No. 1107RJZK243).

1. Synthesis and Catalytic Activity of Novel Heternuclear Dication Brønsted Acidic Ionic Liquids.PDF(1161KB)

Abstract

Three new Brøsted-acidic task-specfic ionic liquids (TSILS) that bear two butane sulfonic acid groups based on 1-(morpholinyl-4-yl)-3-(imidazolyl-1-yl)propane (mip) heternuclear dication: 1-[4-(4-sulfobutyl)morpholinium-4-yl]-3-[3-(4- sulfobutyl)-1H-imidazolium-1-yl]propane bis(trifluoromethane sulfonate) {A, [(C₄SO₃H)m(C₄SO₃H)i]p(OTf)₂}, 1-[4-(sul- fobutyl)morpholinium-4-yl]-3-[3-(4-sulfobutyl)-1H-imidazolium-1-yl]propane bis(hydrogen sulfate) {B, [(C₄SO₃H)m(C₄SO₃- H)i]p(HSO₄)₂} and 1-[4-(4-sulfobutyl)morpholinium-4-yl]-3-[3-(4-sulfobutyl)-1H-imidazolium-1-yl]propane bis(bihydrogen phosphate) {C, [(C₄SO₃H)m(C₄SO₃H)i]p(H₂PO₄)₂} were synthesized and characterized by NMR and FT-IR. The imidazolium-based and morpholinium-based single-SO₃H functionalized acidic ionic liquids were used for comparison. Their catalytic activities were investigated in crossed-aldol condensation between cycloalkanone and various aromatic aldehydes. Hammett method has been used to determine the acidity order of these ionic liquids (ILs). The experiment results have shown that the catalytic activities of the three bi-SO₃H-functionalized ILs were stronger than those of single SO₃H functionalized ILs. Their acidity orders were consistent with their catalytic activities. Good adaptability to the reaction substrate and maximum product yield of 90% was observed when [(C₄SO₃H)m(C₄SO₃H)i]p(OTf)₂ was used as catalyst and the catalyst can be reused at least ten times without obvious activity loss.

Key words: bi-SO₃H-functionalized ionic liquids, synthesis, catalytic activity, crossed aldol reaction, Hammett method, reusability

Cite this article

Cui Wenhui, Zhang Youming, Jia Ruyan, Wang Yu, Wei Taibao. Synthesis and Catalytic Activity of Novel Heternuclear Dication Brønsted Acidic Ionic Liquids[J]. Chin. J. Org. Chem., 2015, 35(4): 890-897.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Wilkes, J. S. Green Chem. 2002, 4, 73.
[2] Wasserscheid, P.; Keim, w. Angew. Chem., Int. Ed. 2000, 39, 3772.
[3] Huddleston, J. G.; Visser, A. E.; Reichert, W. M.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Green. Chem. 2001, 3, 156.
[4] Zhang, C. Y.; Shi, R. B.; Chen, C. Y.; Jin, C. M. Chin. J. Org. Chem. 2013, 33, 611 (in Chinese).
(张传越, 石若冰, 陈才元, 金传明, 有机化学, 2013, 33, 611.)
[5] Song, C. H.; Liu, H.; Li, Y.; Ge, S.; Wang, H. W.; Zhu, W. S.; Chang, Y. H.; Han, C. R.; Li, H. M. Chin. J. Chem. 2014, 32, 434.
[6] Wu, W. J.; Zhang, X. Y.; Hu, Y.; Jin, B.; Hua, J. L. Chin. J. Chem. 2013, 31, 388.
[7] Kuang, M.; Zhang, Y.; Yang, P. Y.; Lu, H. J. Acta Chim. Sinica 2013, 71, 1007 (in Chinese).
(匡敏, 张莹, 杨芃原, 陆豪杰, 化学学报, 2013, 71, 1007.)
[8] Li, Y. P.; Qi, L.; Shen, Y.; Zhang, H. Z; Ma, H. M. Chin. J. Chem. 2014, 32, 619.
[9] Gao, X.; Fan, J.; Wang, X. L.; Zhang, Y. S. Acta Chim. Sinica 2013, 71, 1411 (in Chinese).
(高霞, 樊静, 王小龙, 张艳树, 化学学报, 2013, 71, 1411.)
[10] Sheng, W. L.; Tian, F. L.; Du, Y. Y.; Wu, C. Y. Chin. J. Org. Chem. 2013, 33, 835 (in Chinese).
(盛万里, 田福利, 杜玉英, 吴春雨, 有机化学, 2013, 33, 835.)
[11] Song, Y. L.; Wang, X. C.; Huang, C. P.; Liang, F. B.; Yu, Z. C.; Chen, B. H. Chin. J. Org. Chem. 2013, 33, 1715 (in Chinese).
(宋彦磊, 王新承, 黄崇品, 梁凤兵, 毓志超, 陈标华, 有机化学, 2013, 33, 1715.)
[12] Zhao, D. W.; Wu, Y. T.; Chen, T. T.; Dai, L. Y.; Wang, Y. Y. Chin. J. Org. Chem. 2013, 33, 1791 (in Chinese).
(赵东旺, 吴悦彤, 陈婷婷, 戴立益, 王媛媛, 有机化学, 2013, 33, 1791.)
[13] Cole, A C.; Jensen, J. L.; Ntai, L.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, J. H. Jr. J. Am. Chem. Soc. 2002, 124, 5962.
[14] Xing, H. B.; Wang, T.; Zhou, Z. H.; Dai, Y. Y. J. Mol. Catal. A: Chem. 2007, 264, 53.
[15] Huang, B. H.; Wang, Y. F.; Zhang, K.; Fang, Y. X.; Zou, B. L. Chin. J. Catal. 2007, 28, 743 (in Chinese).
(黄宝华, 汪艳飞, 张焜, 方岩雄, 周蓓蕾, 催化学报, 2007, 28, 743.)
[16] Wang, Y. Y.; Wu, Y. T.; Liu, K.; Dai, L. Y. Chin. Chem. Lett. 2012, 23, 1031.
[17] Gui, J. Z.; Cong, X. H.; Liu, D.; Zhang, X. T.; Hu, Z.; Sun, Z. L. Catal. Commun. 2004, 5, 473.
[18] Fang, D.; Zhou, X. L.; Ye, Z. W.; Liu, Z. L. Ind. Eng. Chem. Res. 2006, 45, 7982.
[19] Huang, B. H.; Wang, Y. F.; Du, Z. Y.; Zhang, K.; Fang, Y. X.; Zou, B. L.; Li, Z. J. J. Instrum. Anal. 2007, 26, 478 (in Chinese).
(黄宝华, 汪艳飞, 杜志云, 张焜, 方岩雄, 周蓓蕾, 黎子进, 分析测试学报, 2007, 26, 478.)
[20] Huang, B. H.; Li, Z. J.; Xu, X. L.; Zhang, K.; Fang, Y. X. Chin. J. Org. Chem. 2009, 29, 770 (in Chinese).
(黄宝华, 黎子进, 史娜, 徐效陵, 张焜, 方岩雄, 有机化学, 2009, 29, 770.)
[21] Ling, X. Z.; Gao, S.; Yang, J. G.; He, M. Y. Catal Lett. 2008, 125, 396.
[22] Xu, D. Q.; Wu, J.; Luo, Sh. P.; Zhang, J. X.; Wu, J. Y.; Du, X. H.; Xu, Z. Y. Green Chem. 2009, 11, 1239.
[23] Liu, X. F.; Xiao, L. F.; Wu, H. G. J. L. T.; Li, Z.; Chen, J.;Xia, C. G. J. Catal. Commun. 2009, 10, 424.
[24] Liu, X. F.; Zhao, Y. W.; Li, Z.; Chen, J. Xia, C. G. Chin. J. Chem. 2010, 28, 2003.
[25] Zeng, H. Y.; Ying, S. F.; Li, Y. Chin. J. Org. Chem. 2007, 27, 528 (in Chinese).
(曾鸿耀, 尹述凡, 李颖, 有机化学, 2007, 27, 528.)
[26] Das, B.; Thirupathi, P.; Mahender, I.; Reddy, K. R. J. Mol. Catal. A: Chem. 2006, 247, 182.
[27] Yang, W. Z.; Li, H. Y.; Huang, S. S. Li, J. T.; Wang, S. X.; Cao, Y. Q. Chin. J. Org. Chem. 2005, 25, 994 (in Chinese).
(杨文智, 李海鹰, 黄顺升, 李记太, 王书香, 曹玉庆, 有机化学, 2005, 25, 994).
[28] Kang, L. Q.; Wei, B. G. Chemistry 2007, 70, 801 (in Chinese).
(康丽琴, 魏邦国, 化学通报, 2007, 70, 801.)
[29] An, L. T.; Zou, J. P.; Zhang, L. L. Catal. Commun. 2008, 9, 349.
[30] Ma, F.; Li, L. Q.; Hao, H. E.; Su, Y.; Liu, W. Y. Chin. J. Org. Chem. 2010, 30, 419 (in Chinese).
(马峰, 李立强, 郝海娥, 苏艳, 刘万毅, 有机化学, 2010, 30, 419.)
[31] Lin, P.; Li, B. L.; Li, J. T.;Wang, H. C.; Bian, X. B.; Wang, X. M. Catal. Lett. 2011, 141, 459.
[32] Zhang, X. Y.; Fan, X. S.; Niu, H. Y.; Wang, J. J. Chin. Chem. Lett. 2003, 14, 1005.
[33] Zheng, X. L.; Zhang, Y. M. Synth. Commun. 2003, 33, 161.
[34] Liu, B. Y.; Zhao, D. S.; Xu, D. Q.; Xu, Z. Y. Chem. Res. Chin. Univ. 2007, 23, 549.
[35] Liu, Y.; Zhang, Y. M.; Hua, M. T.; Liu, M. X.; Wei, T. B. Chin. J. Inorg. Chem. 2011, 27, 1569 (in Chinese).
(刘勇, 张有明, 华茂堂, 刘明霞, 魏太保, 无机化学学报, 2011, 27, 1569.)
[36] Wei, T. B.; Dang, J. P.; Lin, Q.; Yao, H.; Liu, Y.; Zhang, W. Q.; Ming, J. J.; Zhang, Y. M. Sci. China Chem. 2012, 55, 2554.
[37] Zhang, Y. M.; Liu, Y.; Lin, Q.; Hua, M. T.; Wang, W. F.; Ma, Y. J.; Wei, T. B. Sci. China Chem. 2011, 41, 869 (in Chinese).
(张有明, 刘勇, 林奇, 华茂堂, 王伟峰, 马永钧, 魏太保, 中国科学: 化学, 2011, 41, 869.)
[38] Zhang, Y. M.; Cui, W. H.; Wai, T. B. Chin. J. Org. Chem. 2007, 27, 893 (in Chinese).
(张有明, 崔文辉, 魏太保, 有机化学, 2007, 27, 893.)
[39] Wai, T. B, Shi, H. X.; Zhang, Z. R.; Cui, W. H.; Zang, Y. M. Chin. J. Org. Chem. 2007, 27, 1116 (in Chinese).
(魏太保, 师海雄, 张治仁, 崔文辉, 张有明, 有机化学, 2007, 27, 1116.)
[40] Liu, X. F.; Chen, J.; Xia, C. G. J. Mol. Catal. 2008, 22, 392 (in Chinese).
(刘晓飞, 陈静, 夏春谷, 分子催化, 2008, 22, 392.)
[41] Kore, R.; Srivastava, R. J. Mol. Catal. A: Chem. 2011, 345, 117.
[42] Yang, L.; Lu, J.; Bai, Y. J. Chin. J. Org. Chem. 2003, 23, 659 (in Chinese).
(杨玲, 路军, 白银娟, 有机化学, 2003, 23, 659.)
[43] Mohammadi ziarani, G.; Badiei, A.; Abbasi, A.; Farahani, Z. Chin. J. Chem. 2009, 27, 1537.

新型异核双阳离子型磺酸功能化离子液体的合成及其催化活性

Synthesis and Catalytic Activity of Novel Heternuclear Dication Brønsted Acidic Ionic Liquids

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[2]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[3]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[4]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[7]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[8]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[9]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[10]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[11]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[12]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[13]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[14]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[15]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.