3-Methoxybutan-2-one as a sustainable bio-based alternative to chlorinated solvents. Issue 62 (10th December 2021)

• Record Type: Journal Article
• Authors: Jin, Saimeng; Byrne, Fergal P.; Clark, James H.; McElroy, Con Robert; Quinn, Alex; Sherwood, James; Hunt, Andrew J.
• Is Part Of: RSC advances. Volume 11:Issue 62(2021)
• Page Start: 39412
• Page End: 39419
• Publication Date: 2021-12-10
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1ra07322b
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Methylation of acetoin with dimethyl carbonate was performed in a sustainable one-step process, with improved process mass intensity (PMI) and atom economy. 3-Methoxybutan-2-one is a sustainable bio-based alternative to chlorinated solvents. 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.