Epoxidation of cyclopentene by a low cost and environmentally friendly bicarbonate/peroxide/manganese system

Hincapie, Beatriz; Llano, Sandra M.; Garces, Hector F.; Espinal, Diego; Suib, Steven L.; Garces, Luis J.

doi:10.1177/0263617417701744

Epoxidation of cyclopentene by a low cost and environmentally friendly bicarbonate/peroxide/manganese system

Journal Article · Tue Apr 25 00:00:00 EDT 2017 · Adsorption Science and Technology

DOI:https://doi.org/10.1177/0263617417701744· OSTI ID:1498901

Hincapie, Beatriz ^[1]; Llano, Sandra M. ^[2]; Garces, Hector F. ^[3]; Espinal, Diego ^[2]; Suib, Steven L. ^[4]; Garces, Luis J. ^[2]

Universidad de Antioquia (Colombia); Laboratorio de Cata´lisis Industrial, Instituto de Quı´mica, Facultad de Ciencias Exactas y Naturales, Universidad de Antioquia UdeA, Calle 70 No 52-21, Medellı´n, Colombi
Universidad de Antioquia (Colombia)
Brown Univ., Providence, RI (United States)
Univ. of Connecticut, Storrs, CT (United States)

The system hydrogen peroxide/sodium bicarbonate/manganese sulfate was used for the first time to epoxidize cyclopentene. Effects of parameters such as type and amount of solvent, ratio of hydrogen peroxide and manganese sulfate to cyclopentene, presence of additives, and reaction time and temperature on the selectivity to cyclopentene oxide were evaluated. Gas chromatography was used to quantify residual cyclopentene and produced cyclopentene oxide using the internal standard method. Type and amount of solvent, addition method, and temperature were important factors to increase the selectivity to cyclopentene oxide. Unlike previous reports on epoxidation of different substrates, additives like sodium acetate and salicylic acid did not improve the selectivity to cyclopentene oxide. One time, single-step addition of hydrogen peroxide/sodium bicarbonate to the solution of cyclopentene/solvent/manganese sulfate produced more cyclopentene oxide than stepwise addition. The maximum selectivity obtained was 56%, possibly due to the high reactivity of cyclopentene that causes the formation of oxidation products different to cyclopentene oxide, which were not detected in the analyzed phase.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Connecticut, Storrs, CT (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: FG02-86ER13622

OSTI ID:: 1498901

Journal Information:: Adsorption Science and Technology, Journal Name: Adsorption Science and Technology Journal Issue: 1-2 Vol. 36; ISSN 0263-6174

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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Epoxidation of cyclopentene by a low cost and environmentally friendly bicarbonate/peroxide/manganese system

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