A scale-up procedure to dialkyl carbonates; evaluation of their properties, biodegradability, and toxicity
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In: Sustainable Chemistry and Pharmacy, Vol. 26, 100639, 01.05.2022.
Research output: Journal contributions › Journal articles › Research › peer-review
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TY - JOUR
T1 - A scale-up procedure to dialkyl carbonates; evaluation of their properties, biodegradability, and toxicity
AU - Trapasso, Giacomo
AU - Salaris, Claudio
AU - Reich, Marco
AU - Logunova, Evgenia
AU - Salata, Cristiano
AU - Kümmerer, Klaus
AU - Figoli, Alberto
AU - Aricò, Fabio
N1 - Publisher Copyright: © 2022 Elsevier B.V.
PY - 2022/5/1
Y1 - 2022/5/1
N2 - In this work, we explored a scale-up procedure to non-commercially available or expensive dialkyl carbonates via transcarbonylation reaction of an alcohol with dimethyl carbonate promoted by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). DACs selected for this study include symmetrical and unsymmetrical compounds incorporating alkyl, alkoxyalkyl, aminoalkyl, and thioalkyl moieties. Compared to previously published works, the proposed procedure was customized for large-scale production of DACs (up to 100 mL); purification of the products was achieved by distillation, and recycling of the exceeding reagents was addressed. Furthermore, the role of the catalyst was investigated, and a possible reaction mechanism proposed. The chemical-physical properties of the new DACs were evaluated employing softwares and models based on quantitative structure-activity relationships (QSAR). Biodegradability and toxicity tests have also been carried out both experimentally and by computational studies so to investigate the effect of the sulfur, nitrogen, or oxygen-containing moieties on the greenness of these – in some cases new –solvents and reagents.
AB - In this work, we explored a scale-up procedure to non-commercially available or expensive dialkyl carbonates via transcarbonylation reaction of an alcohol with dimethyl carbonate promoted by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). DACs selected for this study include symmetrical and unsymmetrical compounds incorporating alkyl, alkoxyalkyl, aminoalkyl, and thioalkyl moieties. Compared to previously published works, the proposed procedure was customized for large-scale production of DACs (up to 100 mL); purification of the products was achieved by distillation, and recycling of the exceeding reagents was addressed. Furthermore, the role of the catalyst was investigated, and a possible reaction mechanism proposed. The chemical-physical properties of the new DACs were evaluated employing softwares and models based on quantitative structure-activity relationships (QSAR). Biodegradability and toxicity tests have also been carried out both experimentally and by computational studies so to investigate the effect of the sulfur, nitrogen, or oxygen-containing moieties on the greenness of these – in some cases new –solvents and reagents.
KW - Chemistry
KW - carbonates
KW - Preparative-scale synthesis
KW - Organic catalyst
KW - Green chemistry
KW - reaction mechanism
KW - diakyl carbonates
KW - Sustainability Science
KW - Toxicity
UR - http://www.scopus.com/inward/record.url?scp=85124536971&partnerID=8YFLogxK
UR - https://www.mendeley.com/catalogue/125bed9a-1be4-3c09-be81-834c513d9c87/
U2 - 10.1016/j.scp.2022.100639
DO - 10.1016/j.scp.2022.100639
M3 - Journal articles
VL - 26
JO - Sustainable Chemistry and Pharmacy
JF - Sustainable Chemistry and Pharmacy
SN - 2352-5541
M1 - 100639
ER -