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

Saimeng Jin; Fergal Byrne; James Hanley Clark; Rob McElroy; Alex Quinn; James Richard Sherwood; Andrew John Hunt

doi:10.1039/D1RA07322B

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

Saimeng Jin, Fergal Byrne, James Hanley Clark, Rob McElroy, Alex Quinn, James Richard Sherwood, Andrew John Hunt

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	39412-39419
Journal	RSC Advances
Volume	11
DOIs	https://doi.org/10.1039/D1RA07322B
Publication status	Published - 10 Dec 2021

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d1ra07322b
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Cite this

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title = "3-Methoxybutan-2-one as 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.",

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T1 - 3-Methoxybutan-2-one as a sustainable bio-based alternative to chlorinated solvents

AU - Jin, Saimeng

AU - Byrne, Fergal

AU - Clark, James Hanley

AU - McElroy, Rob

AU - Quinn, Alex

AU - Sherwood, James Richard

AU - Hunt, Andrew John

PY - 2021/12/10

Y1 - 2021/12/10

N2 - 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.

AB - 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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DO - 10.1039/D1RA07322B

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