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3-Methoxybutan-2-one as a sustainable bio-based alternative to chlorinated solvents

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JournalRSC Advances
DateSubmitted - 1 Oct 2021
DateAccepted/In press - 23 Nov 2021
DatePublished (current) - 10 Dec 2021
Volume11
Pages (from-to)39412-39419
Original languageEnglish

Abstract

Methylation of acetoin with dimethyl carbonate was performed in a sustainable one-step process, with improved process mass intensity (PMI) and atom economy compared to previously published methods. The resulting product, 3-methoxybutan-2-one (MO) was successfully evaluated as a bio-based solvent, while both Kamlet–Taft solvatochromic parameters and Hansen solubility parameters demonstrate its potential viability in the substitution of chlorinated solvents. MO exhibited a low peroxide forming potential and a negative Ames mutagenicity test and was successfully used as a solvent in a Friedel–Crafts acylation (79% yield compared to 77% in dichloromethane) and for N-alkylations. MO is a renewable oxygenated solvent, with the potential ability to substitute carcinogenic halogenated solvents in some applications.

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© The Royal Society of Chemistry 2021.

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