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

    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

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    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:
    Depositing User: Fergal Byrne
    Date Deposited: 29 Jun 2023 13:08
    Journal or Publication Title: RSC Advances
    Publisher: ACS Publications
    Refereed: Yes
    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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