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Frontiers of Chemical Science and Engineering

ISSN 2095-0179

ISSN 2095-0187(Online)

CN 11-5981/TQ

邮发代号 80-969

2019 Impact Factor: 3.552

Frontiers of Chemical Engineering in China  2009, Vol. 3 Issue (3): 310-313   https://doi.org/10.1007/s11705-009-0168-7
  RESEARCH ARTICLE 本期目录
Selective epoxidation of linear terminal olefins with metalloporphyrins under mild conditions
Selective epoxidation of linear terminal olefins with metalloporphyrins under mild conditions
Xiaoguang BAI, Yuanbin SHE()
Institute of Green Chemistry and Fine Chemicals, Department of Chemistry and Chemical Engineering, College of Environmental and Energy Engineering, Beijing University of Technology, Beijing 100124, China
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Abstract

The epoxidation of linear terminal olefins with metalloporphyrins in the presence of dioxygen and isobutyraldehyde under ambient temperature and atmospheric pressure was investigated. The results show that all olefins could be smoothly converted to epoxides with high selectivities (70%-90%). For the metalloporphyrins with different catalytic activities within 1-hexene epoxidation in the order of Fe>Mn>Co, T(o-Cl)PPFe(Ⅲ)Cl was most effective, with a 41.7% yield and 80.2% selectivity of 1,2-epoxyhexane. Various amounts of catalyst were investigated, and it was found that with only 10 ppm catalyst the yield of 1,2-epoxyhexane and turnover number (TON) could reach up to 41.9% and 41859, respectively.

Key wordsmetalloporphyrins    olefins    dioxygen    epoxidation
收稿日期: 2008-09-20      出版日期: 2009-09-05
Corresponding Author(s): SHE Yuanbin,Email:sheyb@bjut.edu.cn   
 引用本文:   
. Selective epoxidation of linear terminal olefins with metalloporphyrins under mild conditions[J]. Frontiers of Chemical Engineering in China, 2009, 3(3): 310-313.
Xiaoguang BAI, Yuanbin SHE. Selective epoxidation of linear terminal olefins with metalloporphyrins under mild conditions. Front Chem Eng Chin, 2009, 3(3): 310-313.
 链接本文:  
https://academic.hep.com.cn/fcse/CN/10.1007/s11705-009-0168-7
https://academic.hep.com.cn/fcse/CN/Y2009/V3/I3/310
Fig.1  
entryn1-hexene/nisobutyraldehydeselectivity/%yield/%TON
11∶172.923.62357
21∶369.235.53550
31∶571.039.23923
41∶772.939.83978
5b)1∶770.210.6
6c)no aldehyde000
Tab.1  
Fig.2  
entrycatalystselectivity/%yield/%
1T(o-Cl)PPFeCl80.241.7
2T(o-Cl)PPMnCl68.437.5
3T(p-Cl)PPMnCl62.128.5
4T(o-Cl)PPCoCl54.028.3
Tab.2  
entryamount of catalyst/ppmselectivity/%yield/%TON
11088.241.941859
210071.039.23923
3100075.625.7257
Tab.3  
entrysubstrateselectivity/%yield/%
11-hexene70.838.5
21-octene73.926.4
31-decene90.234.2
41-dodecene89.520.9
Tab.4  
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