Jin, S., Byrne, F.P., Clark, J.H. , McElroy, Con, Quinn, A., Sherwood, J. and Hunt, A.J. (2021) 3-Methoxybutan-2-one as a sustainable bio-based alternative to chlorinated solvents. RSC Advances, 11 (62). pp. 39412-39419. ISSN 2046-2069
Full content URL: https://doi.org/10.1039/d1ra07322b
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d1ra07322b.pdf - Whole Document Available under License Creative Commons Attribution-NonCommercial 4.0 International. 778kB |
| Item Type: | Article |
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| Item Status: | Live Archive |
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.
| Additional Information: | cited By 1 |
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| Keywords: | Alkylation, Dichloromethane, Halogenation, Methylation, Acetoin, Atom economy, Bio-based, Bio-based solvents, Chlorinated solvent, Dimethyl carbonate, Improved process, Kamlet-taft, One-step process, Solvatochromic parameters, Solvents |
| Subjects: | F Physical Sciences > F100 Chemistry |
| Divisions: | College of Science > School of Chemistry |
| Related URLs: | |
| ID Code: | 54733 |
| Deposited On: | 22 May 2023 10:58 |
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