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tert-butanol and hydrogen peroxide react over Amberlyst-15 to form tert-butyl hydroperoxide

Marie‐Thérèse El Kfoury, Olga V. Chub, Daria Camilla Boffito and Gregory Scott Patience

Article (2024)

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Abstract

Organic peroxides are explosive compounds that are applied as disinfectants, bleaching agents, and as initiators for polymer synthesis because of their high reactivity. Traditional homogeneous processes with H₂SO₄ catalyst produce salts, either in the neturalization step after reaction or due to the foramtion of tert-butyl hydrogen sulphate, that must be disposed of, which introduces cost and represents an environmental burden. Here, we devised a flow chemistry approach to oxidize tert-butyl alcohol (TBA) to tert-butyl hydroperoxide (TBHP) over various heterogeneous catalysts. Under acidic conditions, TBHP is the main product and di-tert-butyl peroxide (DTBP) and peroxy-ketal are by-products. The most active catalyst was Amberlyst-15, while yield of Nafion, activated carbon, and heteropoly acids (HPA) on carbon and silica matrices was less than 1% at 70°C. In in the range of 30 to 50°C, a first order kinetic expression characterizes the tert-butyl alcohol conversion well ($ {R}^2=0.99 $). The reaction rate is slow and the rate constant, $ {k}_{40^{\circ}\mathrm{C}} $, was 0.003 min⁻¹. Above 50°C, by-products reacted further to acetone, methane, ethane, and other compounds.

Uncontrolled Keywords

heterogeneous catalysis; hydrogen peroxide; kinetics; tert-butyl alcohol; tert-butylhydroperoxide

Subjects: 1800 Chemical engineering > 1800 Chemical engineering
Department: Department of Chemical Engineering
Funders: Mitacs, Arkema
Grant number: IT18514, DB/CDT 04 5959
PolyPublie URL: https://publications.polymtl.ca/56708/
Journal Title: Canadian Journal of Chemical Engineering (vol. 102, no. 4)
Publisher: Wiley-Blackwell
DOI: 10.1002/cjce.25136
Official URL: https://doi.org/10.1002/cjce.25136
Date Deposited: 29 Nov 2023 10:02
Last Modified: 08 Apr 2024 21:56
Cite in APA 7: El Kfoury, M.‐T., Chub, O. V., Boffito, D. C., & Patience, G. S. (2024). tert-butanol and hydrogen peroxide react over Amberlyst-15 to form tert-butyl hydroperoxide. Canadian Journal of Chemical Engineering, 102(4), 1583-1591. https://doi.org/10.1002/cjce.25136

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