Efficient organocatalytic synthesis of styrene oxide from styrene and its kinetic study in a continuous-flow microreaction system

Wu, Yuxin; Chen, Zhuo; Wang, Fajun; Xu, Jianhong; Wang, Yundong

doi:10.1016/j.ces.2021.117045

Cited by 11 publications

(6 citation statements)

References 34 publications

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“…According to our previous work, hydrogen peroxide would decompose at high temperature and in an alkali environment. In this work, an acidic environment was caused by the catalyst .…”

Section: Resultsmentioning

confidence: 99%

Kinetic Studies and Reaction Network in the Epoxidation of Styrene Catalyzed by the Temperature-Controlled Phase-Transfer Catalyst [(C₁₈H₃₇)₂(CH₃)₂N]₇[PW₁₁O₃₉]

Chen

Wang

et al. 2022

Ind. Eng. Chem. Res.

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The olefin epoxidation reaction is of great interest in recent years since epoxide is considered an important intermediate for a wide application range. H2O2-based catalytic epoxidation possesses the advantages of being cheap, green, and safe, which are quite advantageous in chemical technology. A phase-transfer catalyst, especially the phosphotungstate catalyst, has been applied in the epoxidation reaction with a high reaction rate and moderate reaction conditions. In this work, a phase-transfer catalyst, [(C18H37)2(CH3)2N]7[PW11O39], has been synthesized, and it showed high catalytic efficiency in styrene epoxidation. The influence of reaction time, temperature, oxidant concentration and amount, catalyst amount, and substrate concentration on the reaction performance was studied. A styrene conversion of 90.1% and selectivity of 90.6% could be achieved at 85 °C for 1 h with 3 equiv of H2O2 and 1.5 mol % catalyst. More importantly, kinetic models for the reaction network have been studied to optimize the reaction conditions and limit the side reactions.

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“…According to our previous work, hydrogen peroxide would decompose at high temperature and in an alkali environment. In this work, an acidic environment was caused by the catalyst .…”

Section: Resultsmentioning

confidence: 99%

Kinetic Studies and Reaction Network in the Epoxidation of Styrene Catalyzed by the Temperature-Controlled Phase-Transfer Catalyst [(C₁₈H₃₇)₂(CH₃)₂N]₇[PW₁₁O₃₉]

Chen

Wang

et al. 2022

Ind. Eng. Chem. Res.

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“…Inspired by Kokotos' work on organocatalytic alkene epoxidation, Tyablikov and coworkers developed a heterogenous catalyst, where the 2,2,2-triuoroacetophenone moiety of 3 was embedded in SBA-15 mesoporous silica, in their effort to prepare a catalyst that can be easily recycled. 23 Furthermore, two different research groups 24,25 sought to harness this protocol, for large-scale reactions. Employing continuous-ow reactor apparatus, Zheng and coworkers improved mass and heat transfer rates.…”

Section: Hydrogen Peroxide-mediated Epoxidation Reactionsmentioning

confidence: 99%

Organocatalytic activation of hydrogen peroxide: towards green and sustainable oxidations

Poursaitidis,

Gkizis,

Triandafillidi

et al. 2024

Chem. Sci.

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“…Therefore, the kinetic equation of the epoxidation reaction [Eq. ( 1)] could be simplified as Equation (4).…”

Section: Chemphotochemmentioning

confidence: 99%

“…The main drawbacks of these classic approaches are mainly contained the using of strongly oxidizing reagents and highly corrosive reactants. [4] To overcome these drawbacks, synthesis of styrene oxide through directly epoxidation of styrene using environmental-begin oxidants is therefore necessary. Among them, heterogeneous catalysts such as nitrides, [5] single-atomicsite catalysts [6][7][8] and others [9,10] have been proposed as promising alternatives for their good oxidation activity and recyclable nature.…”

Section: Introductionmentioning

confidence: 99%

Perovskite LaSrCoFeO₆ Oxide Enabled Visible Light Catalytic Aerobic Epoxidation of Styrene

Fang

Tang

et al. 2022

ChemPhotoChem

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In the search for a highly efficient heterogeneous catalyst for the epoxidation of styrene, it is still a challenge to develop a system that simultaneously possesses superior catalytic activity and selectivity under aerobic conditions. Herein, we report the use of perovskite LaSrCoFeO6 (LSCF) as a heterogeneous and visible‐light catalyst, and determine that LSCF acts as a highly efficient catalyst for the epoxidation of styrene under aerobic conditions. The formation of 1O2 species transformed from O2⋅− species were proposed as reactive oxygen species for the epoxidation of styrene over the LSCF catalyst, where the directional generation of O2⋅− species on the LSCF catalyst is the key step to yield highly selective epoxidation of styrene. The experimental results of styrene epoxidation show that when the molar ratio of styrene and LSCF catalyst is 150 : 1 and the reaction is under the conditions of visible light (440 nm) and 100 °C for 6 h, the conversion of styrene and selectivity of styrene oxide reached 99.9 % and 80.3 %, respectively. The reaction rate over LSCF catalyst is as high as 50 mmol ⋅ gcat−1 ⋅ h−1. In addition, the reaction kinetics of the epoxidation of styrene over LSCF catalyst was systematically studied.

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Efficient organocatalytic synthesis of styrene oxide from styrene and its kinetic study in a continuous-flow microreaction system

Cited by 11 publications

References 34 publications

Kinetic Studies and Reaction Network in the Epoxidation of Styrene Catalyzed by the Temperature-Controlled Phase-Transfer Catalyst [(C₁₈H₃₇)₂(CH₃)₂N]₇[PW₁₁O₃₉]

Kinetic Studies and Reaction Network in the Epoxidation of Styrene Catalyzed by the Temperature-Controlled Phase-Transfer Catalyst [(C₁₈H₃₇)₂(CH₃)₂N]₇[PW₁₁O₃₉]

Organocatalytic activation of hydrogen peroxide: towards green and sustainable oxidations

Perovskite LaSrCoFeO₆ Oxide Enabled Visible Light Catalytic Aerobic Epoxidation of Styrene

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Efficient organocatalytic synthesis of styrene oxide from styrene and its kinetic study in a continuous-flow microreaction system

Cited by 11 publications

References 34 publications

Kinetic Studies and Reaction Network in the Epoxidation of Styrene Catalyzed by the Temperature-Controlled Phase-Transfer Catalyst [(C18H37)2(CH3)2N]7[PW11O39]

Kinetic Studies and Reaction Network in the Epoxidation of Styrene Catalyzed by the Temperature-Controlled Phase-Transfer Catalyst [(C18H37)2(CH3)2N]7[PW11O39]

Organocatalytic activation of hydrogen peroxide: towards green and sustainable oxidations

Perovskite LaSrCoFeO6 Oxide Enabled Visible Light Catalytic Aerobic Epoxidation of Styrene

Contact Info

Product

Resources

About

Kinetic Studies and Reaction Network in the Epoxidation of Styrene Catalyzed by the Temperature-Controlled Phase-Transfer Catalyst [(C₁₈H₃₇)₂(CH₃)₂N]₇[PW₁₁O₃₉]

Kinetic Studies and Reaction Network in the Epoxidation of Styrene Catalyzed by the Temperature-Controlled Phase-Transfer Catalyst [(C₁₈H₃₇)₂(CH₃)₂N]₇[PW₁₁O₃₉]

Perovskite LaSrCoFeO₆ Oxide Enabled Visible Light Catalytic Aerobic Epoxidation of Styrene