Jin, Saimeng and Byrne, Fergal P. and Clark, James H. and McElroy, Con Robert and Quinn, Alex and Sherwood, James and Hunt, Andrew 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
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.
| Item Type: |
Article
|
| Additional Information: |
Cite as: Jin, S., Byrne, F.P., Clark, J.H., McElroy, C.R., Quinn, A., Sherwood, J. & Hunt, A.J. 2021, "3-Methoxybutan-2-one as a sustainable bio-based alternative to chlorinated solvents", RSC advances, vol. 11, no. 62, pp. 39412-39419. |
| Keywords: |
Acylation;
Alkylation;
Carcinogens;
Chemistry;
Dichloromethane;
Mutagenicity;
Solubility parameters;
Solvents; |
| Academic Unit: |
Faculty of Science and Engineering > Chemistry |
| Item ID: |
17375 |
| Identification Number: |
https://doi.org/10.1039/d1ra07322b |
| Depositing User: |
Fergal Byrne
|
| Date Deposited: |
29 Jun 2023 13:08 |
| Journal or Publication Title: |
RSC Advances |
| Publisher: |
ACS Publications |
| Refereed: |
Yes |
| URI: |
|
| Use Licence: |
This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available
here |
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