Kinetics of 2-Methylfuran Acylation with Fatty Acid Anhydrides for Biorenewable Surfactants

Naik, Ankita V.; Joseph, Kristeen E.; Shetty, Manish; Ardagh, M. Alexander; Dauenhauer, Paul J.

doi:10.1021/acssuschemeng.0c06847

Kinetics of 2-Methylfuran Acylation with Fatty Acid Anhydrides for Biorenewable Surfactants

Journal Article · Wed Dec 09 00:00:00 EST 2020 · ACS Sustainable Chemistry & Engineering

DOI:https://doi.org/10.1021/acssuschemeng.0c06847· OSTI ID:1865839

Naik, Ankita V. ^[1]; Joseph, Kristeen E. ^[2]; ^[3]; ^[2]; ^[2]

Univ. of Minnesota, Minneapolis, MN (United States); Univ. of Delaware, Newark, DE (United States); University of Minnesota
Univ. of Minnesota, Minneapolis, MN (United States); Univ. of Delaware, Newark, DE (United States)
Univ. of Minnesota, Minneapolis, MN (United States)

Friedel–Crafts acylation using long-chain fatty acid derivatives and biomass-derived furans is the key reaction to produce “alkyl furan ketones”, an important precursor for biorenewable oleo-furan surfactants. In this work, the steady-state acylation kinetics and reaction mechanism were investigated using a model system of 2-methylfuran and n-octanoic anhydride in a fixed-bed tubular reactor using Al-MCM-41, a mesoporous aluminosilicate. An apparent activation energy (15.5 ± 1.4 kcal mol^–1) was obtained for the formation of the acylated product, 2-octanoyl-5-methylfuran (2O5MF), for a temperature range of 348–408 K. Furthermore, the apparent reaction rate orders were ~0.6 and ~0.5 in the 2-methylfuran and anhydride concentrations, respectively, while near-zero apparent rate orders were measured in the product concentrations, indicating negligible product inhibition. An Eley–Rideal catalytic acylation mechanism was proposed to explain the experimentally observed apparent rate orders.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Minnesota, Minneapolis, MN (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: SC0001004

OSTI ID:: 1865839

Alternate ID(s):: OSTI ID: 1850655

Journal Information:: ACS Sustainable Chemistry & Engineering, Journal Name: ACS Sustainable Chemistry & Engineering Journal Issue: 50 Vol. 8; ISSN 2168-0485

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Kinetics of 2-Methylfuran Acylation with Fatty Acid Anhydrides for Biorenewable Surfactants

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