Synthesis of dicationic alkyl imidazolium peroxopolyoxotungsten-based phase transfer catalyst and its catalytic activity for olefin epoxidation

doi:10.1016/S1872-2067(12)60697-4

Chinese Journal of Catalysis ›› 2013, Vol. 34 ›› Issue (12): 2236-2244.DOI: 10.1016/S1872-2067(12)60697-4

• Research papers • Previous Articles Next Articles

Synthesis of dicationic alkyl imidazolium peroxopolyoxotungsten-based phase transfer catalyst and its catalytic activity for olefin epoxidation

Jianghao Wu, Pingping Jiang, Yan Leng, Yuanyuan Ye, Xiaojie Qin

The Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu, China

Received:2013-06-17 Revised:2013-08-21 Online:2013-11-25 Published:2013-11-25
Contact: Pingping Jiang
Supported by:
This work was supported by the National Key Technology R&D Program (2012BAD32B03) and the Cooperative Innovation Foundation of Industry, Academy and Research Institutes (BY2013015-10) in Jiangsu Province of China.

Abstract

Abstract:

Peroxopolyoxotungsten-based hybrid catalysts modified by dicationic long-chain alkyl imidazolium cations have been synthesized and characterized. The catalytic activity of the catalysts was measured for the epoxidation of olefins with H₂O₂. These catalysts proved to be high catalytic activity phase transfer catalysts. In particular, for the catalyst [D₁₂min]_1.5PW₄O₂₄ modified by the dodecyl dicationic imidazolium cation, the conversion of cyclohexene and selectivity for epoxycyclohexane were 97.7% and 96.3%, respectively. After the reaction, the catalyst could be recovered simply by filtration and reused four times. The conversion of cyclohexene and selectivity for epoxycyclohexane were still 72.4% and 97.2%, respectively, after recycling the catalyst four times. In addition, this phase transfer catalyst can be applied to the epoxidation of a wide range of olefins.

Key words: Dicationic ionic liquid, Polyoxometalate, Olefin, Epoxidation, Phase transfer catalyst

Jianghao Wu, Pingping Jiang, Yan Leng, Yuanyuan Ye, Xiaojie Qin. Synthesis of dicationic alkyl imidazolium peroxopolyoxotungsten-based phase transfer catalyst and its catalytic activity for olefin epoxidation[J]. Chinese Journal of Catalysis, 2013, 34(12): 2236-2244.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(12)60697-4

https://www.cjcatal.com/EN/Y2013/V34/I12/2236

References

[1] Espinal L, Suib S L, Rusling J F. J Am Chem Soc, 2004, 126: 7676
[2] Li N N, Liu Y M, Wu H H, Li X H, Xie W, Zhao Z L, Wu P, He M Y. Chin J Catal (李宁宁, 刘月明, 吴海虹, 李晓红, 谢伟, 赵忠林, 吴鹏, 何鸣元. 催化学报), 2008, 29: 102
[3] Lu X N, Lin H Q, Yuan Y Z. Chin J Catal (卢新宁, 林海强, 袁友珠. 催化学报), 2010, 31: 1457
[4] De Faveri G, Ilyashenko G, Watkinson M. Chem Soc Rev, 2011, 40: 1722
[5] Mizuno N, Yamaguchi K, Kamata K. Coordin Chem Rev, 2005, 249: 1944
[6] Wang Y, Jiang P P, Zhang W J, Zheng J W. Appl Surf Sci, 2013, 270: 531
[7] Balula S S, Santos I C M S, Cunha-Silva L, Carvalho A P, Pires J, Freire C, Cavaleiro J A S, de Castro B, Cavaleiro A M V. Catal Today, 2013, 203: 95
[8] Cai W J, Zhou Y, Bao R L, Yue B, He H Y. Chin J Catal (蔡雯佳, 周琰, 包任烈, 岳斌, 贺鹤勇. 催化学报), 2013, 34: 193
[9] Amini M, Haghdoost M M, Bagherzadeh M. Coordin Chem Rev, 2013, 257: 1093
[10] Saisaha P, de Boer J W, Browne W R. Chem Soc Rev, 2013, 42: 2059
[11] Gao P F, Zhang T M, Zhou Y, Zhao Y X. Chin J Catal (高鹏飞, 张铁明, 周媛, 赵永祥. 催化学报), 2011, 32: 166
[12] Ishii Y, Yamawaki K, Yoshida T, Ura T, Ogawa M. J Org Chem, 1987, 52: 1868
[13] Venturello C, Alneri E, Ricci M. J Org Chem, 1983, 48: 3831
[14] Xi Z W, Zhou N, Sun Y, Li K L. Science, 2001, 292: 1139
[15] Zhang H Y, Lü Y, Li J, Gao S, Xi Z W. Chin J Catal (张恒耘, 吕迎, 李军, 高爽, 奚祖威. 催化学报), 2010, 31: 1253
[16] Qiao Y X, Hou Z S, Li H, Hu Y, Feng B, Wang X R, Hua L, Huang Q F. Green Chem, 2009, 11: 1955
[17] Biboum R N, Doungmene F, Keita B, de Oliveira P, Nadjo L, Lepoittevin B, Roger P, Brisset F, Mialane P, Dolbecq A, Mbomekalle I M, Pichon C, Yin P C, Liu T B, Contant R. J Mater Chem, 2012, 22: 319
[18] Hua L, Qiao Y X, Chen J Z, Zhu W W, Guo L, Zhang R, Hou Z S. Chin Sciencepaper (华丽, 乔云香, 陈吉忠, 朱闻闻, 郭立, 张然, 侯震山. 中国科技论文), 2012, 7: 949
[19] Li H, Hou Z S, Qiao Y X, Feng B, Hu Y, Wang X R, Zhao X G. Catal Commun, 2010, 11: 470
[20] Venturello C, D'Aloisio R. J Org Chem, 1988, 53: 1553
[21] Duncan D C, Chambers R C, Hecht E, Hill C L. J Am Chem Soc, 1995, 117: 681
[22] Venturello C, D'Aloisio R, Bart J C J, Ricci M. J Mol Catal, 1985, 32: 107

Synthesis of dicationic alkyl imidazolium peroxopolyoxotungsten-based phase transfer catalyst and its catalytic activity for olefin epoxidation

PDF (PC)

Knowledge

Cited

Abstract

Cite this article

share this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

[1]	Lijuan Sun, Xiaohui Yu, Liyong Tang, Weikang Wang, Qinqin Liu. Hollow dodecahedron K₃PW₁₂O₄₀/CdS core-shell S-scheme heterojunction for photocatalytic synergistic H₂ evolution and benzyl alcohol oxidation [J]. Chinese Journal of Catalysis, 2023, 52(9): 164-175.
[2]	Huijie Li, Manzhou Chi, Xing Xin, Ruijie Wang, Tianfu Liu, Hongjin Lv, Guo-Yu Yang. Highly selective photoreduction of CO₂ catalyzed by the encapsulated heterometallic-substituted polyoxometalate into a photo-responsive metal-organic framework [J]. Chinese Journal of Catalysis, 2023, 50(7): 343-351.
[3]	Peigong Liu, Tiejun Lin, Lei Guo, Xiaozhe Liu, Kun Gong, Taizhen Yao, Yunlei An, Liangshu Zhong. Tuning cobalt carbide wettability environment for Fischer-Tropsch to olefins with high carbon efficiency [J]. Chinese Journal of Catalysis, 2023, 48(5): 150-163.
[4]	Zhipeng Xie, Xiubei Yang, Pei Zhang, Xiating Ke, Xin Yuan, Lipeng Zhai, Wenbin Wang, Na Qin, Cheng-Xing Cui, Lingbo Qu, Xiong Chen. Vinylene-linked covalent organic frameworks with manipulated electronic structures for efficient solar-driven photocatalytic hydrogen production [J]. Chinese Journal of Catalysis, 2023, 47(4): 171-180.
[5]	Shanfan Lin, Yuchun Zhi, Wenna Zhang, Xiaoshuai Yuan, Chengwei Zhang, Mao Ye, Shutao Xu, Yingxu Wei, Zhongmin Liu. Hydrogen transfer reaction contributes to the dynamic evolution of zeolite-catalyzed methanol and dimethyl ether conversions: Insight into formaldehyde [J]. Chinese Journal of Catalysis, 2023, 46(3): 11-27.
[6]	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.
[7]	Yingnan Zhao, Xing Qin, Xinyu Zhao, Xin Wang, Huaqiao Tan, Huiying Sun, Gang Yan, Haiwei Li, Wingkei Ho, Shun-cheng Lee. Polyoxometalates-doped Bi₂O_3-_x/Bi photocatalyst for highly efficient visible-light photodegradation of tetrabromobisphenol A and removal of NO [J]. Chinese Journal of Catalysis, 2022, 43(3): 771-781.
[8]	Zhaopeng Liu, Youming Ni, Zhongpan Hu, Yi Fu, Xudong Fang, Qike Jiang, Zhiyang Chen, Wenliang Zhu, Zhongmin Liu. Insights into effects of ZrO₂ crystal phase on syngas-to-olefin conversion over ZnO/ZrO₂ and SAPO-34 composite catalysts [J]. Chinese Journal of Catalysis, 2022, 43(3): 877-884.
[9]	Yeqin Feng, Lin Qin, Junhao Zhang, Fangyu Fu, Huijie Li, Hua Xiang, Hongjin Lv. Wheel-shaped icosanuclear Cu-containing polyoxometalate catalyst: Mechanistic and stability studies on light-driven hydrogen generation [J]. Chinese Journal of Catalysis, 2022, 43(2): 442-450.
[10]	Jinpeng Yin, Xin Jin, Hao Xu, Yejun Guan, Rusi Peng, Li Chen, Jingang Jiang, Peng Wu. Structured binder-free MWW-type titanosilicate with Si-rich shell for selective and durable propylene epoxidation [J]. Chinese Journal of Catalysis, 2021, 42(9): 1561-1575.
[11]	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.
[12]	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.
[13]	Mo Zhang, Huijie Li, Junhao Zhang, Hongjin Lv, Guo-Yu Yang. Research advances of light-driven hydrogen evolution using polyoxometalate-based catalysts [J]. Chinese Journal of Catalysis, 2021, 42(6): 855-871.
[14]	Jing Du, Yuan-Yuan Ma, Huaqiao Tan, Zhen-Hui Kang, Yangguang Li. Progress of electrochemical CO₂ reduction reactions over polyoxometalate-based materials [J]. Chinese Journal of Catalysis, 2021, 42(6): 920-937.
[15]	Dianwen Hu, Xiaojing Song, Shujie Wu, Xiaotong Yang, Hao Zhang, Xinyu Chang, Mingjun Jia. Solvothermal synthesis of Co-substituted phosphomolybdate acid encapsulated in the UiO-66 framework for catalytic application in olefin epoxidation [J]. Chinese Journal of Catalysis, 2021, 42(2): 356-366.