Greener route to 4-vinyl-1-cyclohexane 1,2-epoxide synthesis using batch and continuous reactors

Misbahu L. Mohammed, Rene Mbeleck, Dipesh Patel, David C. Sherrington, Basudeb Saha

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Polystyrene 2-(aminomethyl)pyridine (Ps.AMP) supported molybdenum (Mo)(VI) complex (Ps.AMP.Mo) was prepared, characterized and assessed as a catalyst for batch and continuous epoxidation of 4-vinyl-1-cyclohexene (4-VCH) using tert-butyl hydroperoxide (TBHP) as an oxidant. The effect of various parameters such as reaction temperature, feed molar ratio (FMR) of 4-VCH to TBHP and catalyst loading on the conversion of TBHP to 4-vinyl-1-cyclohexane 1,2-epoxide (4-VCH 1,2-epoxide) was studied to optimize reaction conditions in a batch reactor. The long-term stability of Ps.AMP.Mo was evaluated by recycling a sample of the catalyst several times in batch experiments. A detailed evaluation of Mo leaching from the polymer supported catalyst was investigated by isolating any residue from reaction supernatant solutions and then using these residues as potential catalysts in epoxidation reactions. The efficiency of Ps.AMP.Mo catalyst for continuous epoxidation studies was assessed using a FlowSyn continuous flow reactor by studying the effect of reaction temperature, feed flow rate and FMR of 4-VCH to TBHP on the conversion of TBHP and the yield of 4-VCH 1,2-epoxide. The experimental results confirmed very high selectivity and efficiency of Ps.AMP.Mo catalyst for batch and continuous epoxidation.
LanguageEnglish
Pages411–418
Number of pages8
JournalGreen Processing and Synthesis
Volume3
Issue number6
DOIs
Publication statusPublished - 26 Nov 2014

Fingerprint

Molybdenum
Epoxy Compounds
tert-Butylhydroperoxide
Cyclohexane
Polystyrenes
molybdenum
Epoxidation
Pyridine
catalyst
Catalysts
Temperature
Catalyst selectivity
Batch reactors
Recycling
Oxidants
Catalyst supports
Leaching
reactor
oxidant
Polymers

Keywords

  • 4-vinyl-1-cyclohexene
  • alkene epoxidation
  • continuous flow reactor
  • heterogeneous catalysis
  • polymer supported Mo(VI) catalyst

Cite this

Mohammed, Misbahu L. ; Mbeleck, Rene ; Patel, Dipesh ; Sherrington, David C. ; Saha, Basudeb. / Greener route to 4-vinyl-1-cyclohexane 1,2-epoxide synthesis using batch and continuous reactors. In: Green Processing and Synthesis. 2014 ; Vol. 3, No. 6. pp. 411–418.
@article{cac817067b0c4334be85493bc4a5f31e,
title = "Greener route to 4-vinyl-1-cyclohexane 1,2-epoxide synthesis using batch and continuous reactors",
abstract = "Polystyrene 2-(aminomethyl)pyridine (Ps.AMP) supported molybdenum (Mo)(VI) complex (Ps.AMP.Mo) was prepared, characterized and assessed as a catalyst for batch and continuous epoxidation of 4-vinyl-1-cyclohexene (4-VCH) using tert-butyl hydroperoxide (TBHP) as an oxidant. The effect of various parameters such as reaction temperature, feed molar ratio (FMR) of 4-VCH to TBHP and catalyst loading on the conversion of TBHP to 4-vinyl-1-cyclohexane 1,2-epoxide (4-VCH 1,2-epoxide) was studied to optimize reaction conditions in a batch reactor. The long-term stability of Ps.AMP.Mo was evaluated by recycling a sample of the catalyst several times in batch experiments. A detailed evaluation of Mo leaching from the polymer supported catalyst was investigated by isolating any residue from reaction supernatant solutions and then using these residues as potential catalysts in epoxidation reactions. The efficiency of Ps.AMP.Mo catalyst for continuous epoxidation studies was assessed using a FlowSyn continuous flow reactor by studying the effect of reaction temperature, feed flow rate and FMR of 4-VCH to TBHP on the conversion of TBHP and the yield of 4-VCH 1,2-epoxide. The experimental results confirmed very high selectivity and efficiency of Ps.AMP.Mo catalyst for batch and continuous epoxidation.",
keywords = "4-vinyl-1-cyclohexene, alkene epoxidation, continuous flow reactor, heterogeneous catalysis, polymer supported Mo(VI) catalyst",
author = "Mohammed, {Misbahu L.} and Rene Mbeleck and Dipesh Patel and Sherrington, {David C.} and Basudeb Saha",
year = "2014",
month = "11",
day = "26",
doi = "10.1515/gps-2014-0058",
language = "English",
volume = "3",
pages = "411–418",
journal = "Green Processing and Synthesis",
issn = "2191-9542",
number = "6",

}

Greener route to 4-vinyl-1-cyclohexane 1,2-epoxide synthesis using batch and continuous reactors. / Mohammed, Misbahu L.; Mbeleck, Rene; Patel, Dipesh; Sherrington, David C.; Saha, Basudeb.

In: Green Processing and Synthesis, Vol. 3, No. 6, 26.11.2014, p. 411–418.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Greener route to 4-vinyl-1-cyclohexane 1,2-epoxide synthesis using batch and continuous reactors

AU - Mohammed, Misbahu L.

AU - Mbeleck, Rene

AU - Patel, Dipesh

AU - Sherrington, David C.

AU - Saha, Basudeb

PY - 2014/11/26

Y1 - 2014/11/26

N2 - Polystyrene 2-(aminomethyl)pyridine (Ps.AMP) supported molybdenum (Mo)(VI) complex (Ps.AMP.Mo) was prepared, characterized and assessed as a catalyst for batch and continuous epoxidation of 4-vinyl-1-cyclohexene (4-VCH) using tert-butyl hydroperoxide (TBHP) as an oxidant. The effect of various parameters such as reaction temperature, feed molar ratio (FMR) of 4-VCH to TBHP and catalyst loading on the conversion of TBHP to 4-vinyl-1-cyclohexane 1,2-epoxide (4-VCH 1,2-epoxide) was studied to optimize reaction conditions in a batch reactor. The long-term stability of Ps.AMP.Mo was evaluated by recycling a sample of the catalyst several times in batch experiments. A detailed evaluation of Mo leaching from the polymer supported catalyst was investigated by isolating any residue from reaction supernatant solutions and then using these residues as potential catalysts in epoxidation reactions. The efficiency of Ps.AMP.Mo catalyst for continuous epoxidation studies was assessed using a FlowSyn continuous flow reactor by studying the effect of reaction temperature, feed flow rate and FMR of 4-VCH to TBHP on the conversion of TBHP and the yield of 4-VCH 1,2-epoxide. The experimental results confirmed very high selectivity and efficiency of Ps.AMP.Mo catalyst for batch and continuous epoxidation.

AB - Polystyrene 2-(aminomethyl)pyridine (Ps.AMP) supported molybdenum (Mo)(VI) complex (Ps.AMP.Mo) was prepared, characterized and assessed as a catalyst for batch and continuous epoxidation of 4-vinyl-1-cyclohexene (4-VCH) using tert-butyl hydroperoxide (TBHP) as an oxidant. The effect of various parameters such as reaction temperature, feed molar ratio (FMR) of 4-VCH to TBHP and catalyst loading on the conversion of TBHP to 4-vinyl-1-cyclohexane 1,2-epoxide (4-VCH 1,2-epoxide) was studied to optimize reaction conditions in a batch reactor. The long-term stability of Ps.AMP.Mo was evaluated by recycling a sample of the catalyst several times in batch experiments. A detailed evaluation of Mo leaching from the polymer supported catalyst was investigated by isolating any residue from reaction supernatant solutions and then using these residues as potential catalysts in epoxidation reactions. The efficiency of Ps.AMP.Mo catalyst for continuous epoxidation studies was assessed using a FlowSyn continuous flow reactor by studying the effect of reaction temperature, feed flow rate and FMR of 4-VCH to TBHP on the conversion of TBHP and the yield of 4-VCH 1,2-epoxide. The experimental results confirmed very high selectivity and efficiency of Ps.AMP.Mo catalyst for batch and continuous epoxidation.

KW - 4-vinyl-1-cyclohexene

KW - alkene epoxidation

KW - continuous flow reactor

KW - heterogeneous catalysis

KW - polymer supported Mo(VI) catalyst

U2 - 10.1515/gps-2014-0058

DO - 10.1515/gps-2014-0058

M3 - Article

VL - 3

SP - 411

EP - 418

JO - Green Processing and Synthesis

T2 - Green Processing and Synthesis

JF - Green Processing and Synthesis

SN - 2191-9542

IS - 6

ER -