Challenges in the development of bio-based solvents: A case study on methyl(2,2-dimethyl-1,3-dioxolan-4-yl)methyl carbonate as an alternative aprotic solvent

TY - JOUR

T1 - Challenges in the development of bio-based solvents

T2 - A case study on methyl(2,2-dimethyl-1,3-dioxolan-4-yl)methyl carbonate as an alternative aprotic solvent

AU - Jin, Saimeng

AU - Byrne, Fergal

AU - McElroy, Con Robert

AU - Sherwood, James

AU - Clark, James H.

AU - Hunt, Andrew J.

N1 - © Royal Society of Chemistry 2017. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

PY - 2017/9/1

Y1 - 2017/9/1

N2 - Many traditional solvents have drawbacks including sustainability and toxicity issues. Legislations such as REACH is driving the move towards less hazardous chemicals and production processes. Therefore, safer bio-based solvents need to be developed. Herein, a 10 step method has been proposed for the development of new bio-based solvents that utilise a combination of in silico modelling of Hansen solubility parameters (HSPs), experimental Kamlet-Abboud-Taft parameters, selection of green synthetic routes followed by applications testing and toxicity measurements. The challenges that the chemical industry face in the development of new bio-based solvents are highlighted through a case study on methyl (2,2-dimethyl-1,3-dioxolan-4-yl) methyl carbonate (MMC) which can be synthesised from glycerol. Although MMC is an attractive candidate as a replacement solvent, simply being bio-derived is not enough for a molecule to be regarded as green. The methodology of solvent development described here is a broadly applicable protocol that will indicate if a new bio-based solvent is functionally proficient, but will also highlight the importance of early stage Kamlet-Abboud-Taft parameters determination and toxicity testing in the development of a green solvent.

AB - Many traditional solvents have drawbacks including sustainability and toxicity issues. Legislations such as REACH is driving the move towards less hazardous chemicals and production processes. Therefore, safer bio-based solvents need to be developed. Herein, a 10 step method has been proposed for the development of new bio-based solvents that utilise a combination of in silico modelling of Hansen solubility parameters (HSPs), experimental Kamlet-Abboud-Taft parameters, selection of green synthetic routes followed by applications testing and toxicity measurements. The challenges that the chemical industry face in the development of new bio-based solvents are highlighted through a case study on methyl (2,2-dimethyl-1,3-dioxolan-4-yl) methyl carbonate (MMC) which can be synthesised from glycerol. Although MMC is an attractive candidate as a replacement solvent, simply being bio-derived is not enough for a molecule to be regarded as green. The methodology of solvent development described here is a broadly applicable protocol that will indicate if a new bio-based solvent is functionally proficient, but will also highlight the importance of early stage Kamlet-Abboud-Taft parameters determination and toxicity testing in the development of a green solvent.

UR - http://www.scopus.com/inward/record.url?scp=85029844786&partnerID=8YFLogxK

U2 - 10.1039/c7fd00049a

DO - 10.1039/c7fd00049a

M3 - Article

AN - SCOPUS:85029844786

SN - 1359-6640

VL - 202

SP - 157

EP - 173

JO - FARADAY DISCUSSIONS

JF - FARADAY DISCUSSIONS

ER -