One-pot synthesis of styrene carbonate from styrene in tetrabutylammonium bromide

Jianmin Sun; Shin Ichiro Fujita; Bhalchandra M. Bhanage; Masahiko Arai

doi:10.1016/j.cattod.2004.06.105

One-pot synthesis of styrene carbonate from styrene in tetrabutylammonium bromide

Jianmin Sun
, Shin Ichiro Fujita
, Bhalchandra M. Bhanage
, Masahiko Arai^*

^*Corresponding author for this work

Hokkaido University

Research output: Contribution to journal › Conference article › peer-review

88 Scopus citations

Abstract

Styrene carbonate is synthesized by a direct benign route in the presence of tetrabutylammonium bromide (TBAB) from styrene, compressed CO₂ and tert-butyl hydroperoxide (TBHP) as oxidant, in which two sequential reactions of epoxidation and cycloaddition are coupled for a one-pot synthesis. Various reaction parameters, such as CO₂ pressure, reaction temperature and time, TBAB concentration, molar ratio of TBHP to styrene and oxidant types, were investigated. CO₂ pressure was found to play a crucial role in achieving the high yield of styrene carbonate. A plausible reaction mechanism was also proposed.

Original language	English
Pages (from-to)	383-388
Number of pages	6
Journal	Catalysis Today
Volume	93-95
DOIs	https://doi.org/10.1016/j.cattod.2004.06.105
State	Published - 1 Sep 2004
Externally published	Yes
Event	Selections from the Presentations of the 3rd Asia-Pacific Congress - Dalian, China Duration: 12 Oct 2003 → 12 Oct 2003

Keywords

Carbon dioxide
One-pot synthesis
Styrene
Styrene carbonate
Tert-Butyl hydroperoxide
Tetrabutylammonium bromide

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10.1016/j.cattod.2004.06.105

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title = "One-pot synthesis of styrene carbonate from styrene in tetrabutylammonium bromide",

abstract = "Styrene carbonate is synthesized by a direct benign route in the presence of tetrabutylammonium bromide (TBAB) from styrene, compressed CO2 and tert-butyl hydroperoxide (TBHP) as oxidant, in which two sequential reactions of epoxidation and cycloaddition are coupled for a one-pot synthesis. Various reaction parameters, such as CO2 pressure, reaction temperature and time, TBAB concentration, molar ratio of TBHP to styrene and oxidant types, were investigated. CO2 pressure was found to play a crucial role in achieving the high yield of styrene carbonate. A plausible reaction mechanism was also proposed.",

keywords = "Carbon dioxide, One-pot synthesis, Styrene, Styrene carbonate, Tert-Butyl hydroperoxide, Tetrabutylammonium bromide",

author = "Jianmin Sun and Fujita, \{Shin Ichiro\} and Bhanage, \{Bhalchandra M.\} and Masahiko Arai",

year = "2004",

month = sep,

day = "1",

doi = "10.1016/j.cattod.2004.06.105",

language = "英语",

volume = "93-95",

pages = "383--388",

journal = "Catalysis Today",

issn = "0920-5861",

publisher = "Elsevier B.V.",

note = "Selections from the Presentations of the 3rd Asia-Pacific Congress ; Conference date: 12-10-2003 Through 12-10-2003",

}

TY - JOUR

T1 - One-pot synthesis of styrene carbonate from styrene in tetrabutylammonium bromide

AU - Sun, Jianmin

AU - Fujita, Shin Ichiro

AU - Bhanage, Bhalchandra M.

AU - Arai, Masahiko

PY - 2004/9/1

Y1 - 2004/9/1

N2 - Styrene carbonate is synthesized by a direct benign route in the presence of tetrabutylammonium bromide (TBAB) from styrene, compressed CO2 and tert-butyl hydroperoxide (TBHP) as oxidant, in which two sequential reactions of epoxidation and cycloaddition are coupled for a one-pot synthesis. Various reaction parameters, such as CO2 pressure, reaction temperature and time, TBAB concentration, molar ratio of TBHP to styrene and oxidant types, were investigated. CO2 pressure was found to play a crucial role in achieving the high yield of styrene carbonate. A plausible reaction mechanism was also proposed.

AB - Styrene carbonate is synthesized by a direct benign route in the presence of tetrabutylammonium bromide (TBAB) from styrene, compressed CO2 and tert-butyl hydroperoxide (TBHP) as oxidant, in which two sequential reactions of epoxidation and cycloaddition are coupled for a one-pot synthesis. Various reaction parameters, such as CO2 pressure, reaction temperature and time, TBAB concentration, molar ratio of TBHP to styrene and oxidant types, were investigated. CO2 pressure was found to play a crucial role in achieving the high yield of styrene carbonate. A plausible reaction mechanism was also proposed.

KW - Carbon dioxide

KW - One-pot synthesis

KW - Styrene

KW - Styrene carbonate

KW - Tert-Butyl hydroperoxide

KW - Tetrabutylammonium bromide

UR - https://www.scopus.com/pages/publications/4344562067

U2 - 10.1016/j.cattod.2004.06.105

DO - 10.1016/j.cattod.2004.06.105

M3 - 会议文章

AN - SCOPUS:4344562067

SN - 0920-5861

VL - 93-95

SP - 383

EP - 388

JO - Catalysis Today

JF - Catalysis Today

T2 - Selections from the Presentations of the 3rd Asia-Pacific Congress

Y2 - 12 October 2003 through 12 October 2003

ER -

One-pot synthesis of styrene carbonate from styrene in tetrabutylammonium bromide

Abstract

Keywords

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