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

Abstract

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.

Functionalized Sulfide Solid Electrolyte with Air-Stable and Chemical-Resistant Oxysulfide Nanolayer for All-Solid-State Batteries

“…In accordance with the typical properties of the sulfides that are vulnerable to highly polar solvents, the observed decrease in σ ion was ∼37% in the PriA sample and less than 8% in the OScA sample, which exhibited a σ ion ratio of 0.9. An important point is that EA has higher polarity than EP; however, the low boiling point (BP) of EA is advantageous for drying, 43 which can reduce the amount of the residual organic content. Moreover, the results of using toluene and xylene need to be noted.…”

Lead Halide Perovskite Nanocrystals: Room Temperature Syntheses toward Commercial Viability

“…There have also been investigations of the solvent properties of ketones and esters, which can be derived from potentially renewable feedstocks. [153] Multiple solvents were identified with very similar solubility parameters to toluene with boiling points between 100 and 115 °C, albeit with slightly higher polarity. These included the esters methyl pivalate, methyl butyrate, and ethyl isobutyrate.…”

Safer bio-based solvents to replace toluene and tetrahydrofuran for the biocatalyzed synthesis of polyesters

“…2,2,5,5-Tetramethyloxolane (TMO) possesses a comparable boiling point (112 °C) to toluene (111 °C) and although it is an ether, it does not form hazardous peroxides 8. Several esters and ketones have also recently been suggested as alternatives to toluene, displaying a similar solubility profile and performance in chemical reactions 9…”