PMID- 35492443 OWN - NLM STAT- PubMed-not-MEDLINE LR - 20220716 IS - 2046-2069 (Electronic) IS - 2046-2069 (Linking) VI - 11 IP - 62 DP - 2021 Dec 6 TI - 3-Methoxybutan-2-one as a sustainable bio-based alternative to chlorinated solvents. PG - 39412-39419 LID - 10.1039/d1ra07322b [doi] 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. CI - This journal is (c) The Royal Society of Chemistry. FAU - Jin, Saimeng AU - Jin S AUID- ORCID: 0000-0001-8056-2043 AD - Green Chemistry Centre of Excellence, Department of Chemistry, University of York York YO10 5DD UK. FAU - Byrne, Fergal P AU - Byrne FP AD - Green Chemistry Centre of Excellence, Department of Chemistry, University of York York YO10 5DD UK. FAU - Clark, James H AU - Clark JH AUID- ORCID: 0000-0002-5860-2480 AD - Green Chemistry Centre of Excellence, Department of Chemistry, University of York York YO10 5DD UK. FAU - McElroy, Con Robert AU - McElroy CR AUID- ORCID: 0000-0003-2315-8153 AD - Green Chemistry Centre of Excellence, Department of Chemistry, University of York York YO10 5DD UK. FAU - Quinn, Alex AU - Quinn A AD - Green Chemistry Centre of Excellence, Department of Chemistry, University of York York YO10 5DD UK. FAU - Sherwood, James AU - Sherwood J AUID- ORCID: 0000-0001-5431-2032 AD - Green Chemistry Centre of Excellence, Department of Chemistry, University of York York YO10 5DD UK. FAU - Hunt, Andrew J AU - Hunt AJ AUID- ORCID: 0000-0003-3983-8313 AD - Materials Chemistry Research Center, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University Khon Kaen 40002 Thailand andrew@kku.ac.th. LA - eng PT - Journal Article DEP - 20211210 PL - England TA - RSC Adv JT - RSC advances JID - 101581657 PMC - PMC9044657 COIS- There are no conflicts to declare. EDAT- 2022/05/03 06:00 MHDA- 2022/05/03 06:01 PMCR- 2021/12/10 CRDT- 2022/05/02 06:10 PHST- 2021/10/01 00:00 [received] PHST- 2021/11/23 00:00 [accepted] PHST- 2022/05/02 06:10 [entrez] PHST- 2022/05/03 06:00 [pubmed] PHST- 2022/05/03 06:01 [medline] PHST- 2021/12/10 00:00 [pmc-release] AID - d1ra07322b [pii] AID - 10.1039/d1ra07322b [doi] PST - epublish SO - RSC Adv. 2021 Dec 10;11(62):39412-39419. doi: 10.1039/d1ra07322b. eCollection 2021 Dec 6.