Selective epoxidation and allylic oxidation of olefins catalyzed by BEA-Ti and porphyrin catalysts

Tingting Ma; Chao Xu; Fengyang Liu; Yirong Feng; Wenyan Zhang; Weiwei Tang; Haoyu Zhang; Xiaowei Li; Yingying Nie; Shuangfei Zhao; Yuguang Li; Dong Ji; Zheng Fang; Wei He; Kai Guo

doi:10.1016/j.mcat.2023.113074

Selective epoxidation and allylic oxidation of olefins catalyzed by BEA-Ti and porphyrin catalysts

Tingting Ma, Chao Xu, Fengyang Liu, Yirong Feng, Wenyan Zhang, Weiwei Tang, Haoyu Zhang, Xiaowei Li, Yingying Nie, Shuangfei Zhao, Yuguang Li, Dong Ji, Zheng Fang, Wei He, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

Selective epoxidation and allylic oxidation of cyclohexene were realized in the presence of BEA-Ti and (metallo)porphyrin catalysts. The integration of BEA-Ti and porphyrin H₂MTPP afforded cyclohexene oxide with excellent selectivity (cyclohexene oxide/ 2-cyclohexen-1-one=85:15). BEA-Ti and metalloporphyrin MnMTPP yielded 2-cyclohexen-1-one with high selectivity (cyclohexene oxide/ 2-cyclohexen-1-one=12:88). Resulting active species involving of (metallo)porphyrin, Ti^IV sites and tert-butyl hydroperoxide (TBHP) promoted the oxidation process of cyclohexene. A possible mechanism resulting in the formation cyclohexene oxide and 2-cyclohexen-1-one was proposed. The outer-sphere effect constructed by (metallo)porphyrin, Ti^IV sites and TBHP on the surface of BEA-Ti framework improved the epoxidation and allylic oxidation both in the conversion and selectivity.

Original language	English
Article number	113074
Journal	Molecular Catalysis
Volume	541
DOIs	https://doi.org/10.1016/j.mcat.2023.113074
State	Published - 15 Apr 2023

Keywords

Allylic oxidation
BEA-Ti
Epoxidation
Outer-sphere effect
Porphyrin

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10.1016/j.mcat.2023.113074

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@article{cba936c07b4a4e4ab099039865795448,

title = "Selective epoxidation and allylic oxidation of olefins catalyzed by BEA-Ti and porphyrin catalysts",

abstract = "Selective epoxidation and allylic oxidation of cyclohexene were realized in the presence of BEA-Ti and (metallo)porphyrin catalysts. The integration of BEA-Ti and porphyrin H2MTPP afforded cyclohexene oxide with excellent selectivity (cyclohexene oxide/ 2-cyclohexen-1-one=85:15). BEA-Ti and metalloporphyrin MnMTPP yielded 2-cyclohexen-1-one with high selectivity (cyclohexene oxide/ 2-cyclohexen-1-one=12:88). Resulting active species involving of (metallo)porphyrin, TiIV sites and tert-butyl hydroperoxide (TBHP) promoted the oxidation process of cyclohexene. A possible mechanism resulting in the formation cyclohexene oxide and 2-cyclohexen-1-one was proposed. The outer-sphere effect constructed by (metallo)porphyrin, TiIV sites and TBHP on the surface of BEA-Ti framework improved the epoxidation and allylic oxidation both in the conversion and selectivity.",

keywords = "Allylic oxidation, BEA-Ti, Epoxidation, Outer-sphere effect, Porphyrin",

author = "Tingting Ma and Chao Xu and Fengyang Liu and Yirong Feng and Wenyan Zhang and Weiwei Tang and Haoyu Zhang and Xiaowei Li and Yingying Nie and Shuangfei Zhao and Yuguang Li and Dong Ji and Zheng Fang and Wei He and Kai Guo",

note = "Publisher Copyright: {\textcopyright} 2023",

year = "2023",

month = apr,

day = "15",

doi = "10.1016/j.mcat.2023.113074",

language = "英语",

volume = "541",

journal = "Molecular Catalysis",

issn = "2468-8231",

publisher = "Elsevier B.V.",

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TY - JOUR

T1 - Selective epoxidation and allylic oxidation of olefins catalyzed by BEA-Ti and porphyrin catalysts

AU - Ma, Tingting

AU - Xu, Chao

AU - Liu, Fengyang

AU - Feng, Yirong

AU - Zhang, Wenyan

AU - Tang, Weiwei

AU - Zhang, Haoyu

AU - Li, Xiaowei

AU - Nie, Yingying

AU - Zhao, Shuangfei

AU - Li, Yuguang

AU - Ji, Dong

AU - Fang, Zheng

AU - He, Wei

AU - Guo, Kai

PY - 2023/4/15

Y1 - 2023/4/15

N2 - Selective epoxidation and allylic oxidation of cyclohexene were realized in the presence of BEA-Ti and (metallo)porphyrin catalysts. The integration of BEA-Ti and porphyrin H2MTPP afforded cyclohexene oxide with excellent selectivity (cyclohexene oxide/ 2-cyclohexen-1-one=85:15). BEA-Ti and metalloporphyrin MnMTPP yielded 2-cyclohexen-1-one with high selectivity (cyclohexene oxide/ 2-cyclohexen-1-one=12:88). Resulting active species involving of (metallo)porphyrin, TiIV sites and tert-butyl hydroperoxide (TBHP) promoted the oxidation process of cyclohexene. A possible mechanism resulting in the formation cyclohexene oxide and 2-cyclohexen-1-one was proposed. The outer-sphere effect constructed by (metallo)porphyrin, TiIV sites and TBHP on the surface of BEA-Ti framework improved the epoxidation and allylic oxidation both in the conversion and selectivity.

AB - Selective epoxidation and allylic oxidation of cyclohexene were realized in the presence of BEA-Ti and (metallo)porphyrin catalysts. The integration of BEA-Ti and porphyrin H2MTPP afforded cyclohexene oxide with excellent selectivity (cyclohexene oxide/ 2-cyclohexen-1-one=85:15). BEA-Ti and metalloporphyrin MnMTPP yielded 2-cyclohexen-1-one with high selectivity (cyclohexene oxide/ 2-cyclohexen-1-one=12:88). Resulting active species involving of (metallo)porphyrin, TiIV sites and tert-butyl hydroperoxide (TBHP) promoted the oxidation process of cyclohexene. A possible mechanism resulting in the formation cyclohexene oxide and 2-cyclohexen-1-one was proposed. The outer-sphere effect constructed by (metallo)porphyrin, TiIV sites and TBHP on the surface of BEA-Ti framework improved the epoxidation and allylic oxidation both in the conversion and selectivity.

KW - Allylic oxidation

KW - BEA-Ti

KW - Epoxidation

KW - Outer-sphere effect

KW - Porphyrin

UR - http://www.scopus.com/inward/record.url?scp=85150382306&partnerID=8YFLogxK

U2 - 10.1016/j.mcat.2023.113074

DO - 10.1016/j.mcat.2023.113074

M3 - 文章

AN - SCOPUS:85150382306

SN - 2468-8231

VL - 541

JO - Molecular Catalysis

JF - Molecular Catalysis

M1 - 113074

ER -

Selective epoxidation and allylic oxidation of olefins catalyzed by BEA-Ti and porphyrin catalysts

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Keywords

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