A methodical selection process for the development of ketones and esters as bio-based replacements for traditional hydrocarbon solvents

TY - JOUR

T1 - A methodical selection process for the development of ketones and esters as bio-based replacements for traditional hydrocarbon solvents

AU - Byrne, Fergal Patrick

AU - Forier, Bart

AU - Bossaert, Greet

AU - Hoebers, Charly

AU - Farmer, Thomas James

AU - Hunt, Andrew

N1 - © The Royal Society of Chemistry, 2018.

PY - 2018/9/7

Y1 - 2018/9/7

N2 - A “top down” approach to the development of sustainable, greener, low-polarity solvents is presented. Methyl butyrate, ethyl isobutyrate, methyl pivalate and pinacolone were identified as potential target solvents from trends in Hansen solubility parameters and known physical properties. Solubility, flammability and physical properties were determined which showed their potential to replace traditional, hazardous, volatile, non-polar solvents such as toluene. Each new candidate then demonstrated their suitability to replace these traditional solvents in solubility tests, despite being esters and ketones, each candidate demonstrated their similarity to traditional volatile non-polar solvents in terms of their solubility properties by their ability to dissolve natural rubber, a particularly low-polarity solute. This was reinforced by their performance in a model Menschutkin reaction and a radical-initiated polymerisation for the production of pressure-sensitive adhesives, where their performance was found to be similar to that of toluene. Importantly, a preliminary toxicity test (Ames test) suggested non-mutagenicity in all candidates. Each of the four candidates can be synthesised via a catalytic route from potentially renewable resources, thus enhancing their green credentials.

AB - A “top down” approach to the development of sustainable, greener, low-polarity solvents is presented. Methyl butyrate, ethyl isobutyrate, methyl pivalate and pinacolone were identified as potential target solvents from trends in Hansen solubility parameters and known physical properties. Solubility, flammability and physical properties were determined which showed their potential to replace traditional, hazardous, volatile, non-polar solvents such as toluene. Each new candidate then demonstrated their suitability to replace these traditional solvents in solubility tests, despite being esters and ketones, each candidate demonstrated their similarity to traditional volatile non-polar solvents in terms of their solubility properties by their ability to dissolve natural rubber, a particularly low-polarity solute. This was reinforced by their performance in a model Menschutkin reaction and a radical-initiated polymerisation for the production of pressure-sensitive adhesives, where their performance was found to be similar to that of toluene. Importantly, a preliminary toxicity test (Ames test) suggested non-mutagenicity in all candidates. Each of the four candidates can be synthesised via a catalytic route from potentially renewable resources, thus enhancing their green credentials.

UR - http://www.scopus.com/inward/record.url?scp=85052750983&partnerID=8YFLogxK

U2 - 10.1039/c8gc01132j

DO - 10.1039/c8gc01132j

M3 - Article

SN - 1463-9262

VL - 20

SP - 4003

EP - 4011

JO - Green Chemistry

JF - Green Chemistry

IS - 17

ER -