Intelligent Approach to Solvent Substitution: The Identification of a New Class of Levoglucosenone Derivatives

Pacheco, Ana Alves Costa; Sherwood, James; Zhenova, Anna; McElroy, Con Robert; Hunt, Andrew J.; Parker, Helen L.; Farmer, Thomas J.; Constantinou, Andri; bruyn, Mario De; Whitwood, Adrian C.; Raverty, Warwick D.; Clark, James H.

doi:10.1002/cssc.201600795

Cited by 43 publications

(26 citation statements)

References 46 publications

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“…Dihydrolevoglucosenone was one of 164 compounds derivable from levoglucosenone. Clark and colleagues (Pacheco et al 2016 ) subjected this set to a coarse selection method, based on melting point, and Hansen and Kamlet–Taft (K-T) solubility parameters. Fifteen of the 164 were considered as possible replacements for dichloromethane and N- methylpyrrolidone .…”

Section: Solvents and Sustainabilitymentioning

confidence: 99%

The green solvent: a critical perspective

Winterton

2021

Clean Techn Environ Policy

138

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Solvents are important in most industrial and domestic applications. The impact of solvent losses and emissions drives efforts to minimise them or to avoid them completely. Since the 1990s, this has become a major focus of green chemistry, giving rise to the idea of the ‘green’ solvent. This concept has generated a substantial chemical literature and has led to the development of so-called neoteric solvents. A critical overview of published material establishes that few new materials have yet found widespread use as solvents. The search for less-impacting solvents is inefficient if carried out without due regard, even at the research stage, to the particular circumstances under which solvents are to be used on the industrial scale. Wider sustainability questions, particularly the use of non-fossil sources of organic carbon in solvent manufacture, are more important than intrinsic ‘greenness’. While solvency is universal, a universal solvent, an alkahest, is an unattainable ideal.

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Section: Solvents and Sustainabilitymentioning

confidence: 99%

The green solvent: a critical perspective

Winterton

2021

Clean Techn Environ Policy

138

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“…471 and 487) with aL D 50 > 2000 mg kg À1 (OECD No. [44] In related6 ,8-dioxabicyclo[3.2.1]octanone ring systemsi nw hich there is as ubstituent at the b-position, such as alcohol 24 [45] or pyrazole 25, [46] the ketal form can be isolated and characterized. [42] Althoughith as been given ah azard warning for being an eyei rritant (E319), Cyrene has received ECHA level 7c ertification.…”

Section: Use Of Cyrene As Abio-available Solventmentioning

confidence: 99%

Bio‐available Solvent Cyrene: Synthesis, Derivatization, and Applications

2018

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The development of green solvents is one of the key tenets of Green Chemistry as solvents account for the majority of waste stemming from the production of the chemicals on which we have all come to rely. An important class of solvents is the dipolar aprotics, which include N,N-dimethylformamide (DMF) and N-methyl-2-pyrrolidone (NMP). In addition to being derived from non-renewable resources, these solvents are also under increased regulatory pressures that will limit their industrial applications. This Concept concerns the bio-available solvent Cyrene (dihydrolevoglucosenone) as a potential replacement for toxic dipolar aprotic solvents. An emphasis is placed on examining the strengths and weaknesses of Cyrene as a solvent and is accomplished by looking at the synthesis, derivatization, and application in synthetic protocols of Cyrene. With respect to the Twelve Principles of Green Chemistry, this Concept describes a bio-available solvent that should have a disruptive effect on the use of traditional industrial dipolar aprotic solvents.

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“…( c ) The ten solvents with the highest predicted rate constants, annotated with practical issues and molecular schemes. Cygnet 0.0 is spiro-6,8-dioxabicyclo[3.2.1]octane-4,2′-[1,3]dioxolane [35], and Cyrene™ is dihydrolevoglucosenone [33].…”

Section: Figures Schemes and Tablementioning

confidence: 99%

A Method of Calculating the Kamlet–Abboud–Taft Solvatochromic Parameters Using COSMO-RS

et al. 2019

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There is demand for safer and bio-based solvents, brought on by legislation and sustainability objectives. The prediction of physical properties is highly desirable to help design new molecules. Here we present an in silico approach to obtain calculated Kamlet–Abboud–Taft solvatochromic parameters using virtual experiments. The tautomerisation equilibrium of methyl acetoacetate and dimedone was calculated in different solvents with COSMO-RS theory and converted into estimates of solvent dipolarity and hydrogen bond accepting ability, respectively. Hydrogen bond donating ability was calculated as a function of the electron deficient surface area on protic solvents. These polarity descriptors correlate with rate constants and equilibria, and so ability of calculated Kamlet–Abboud–Taft solvatochromic parameters to recreate experimental free energy relationships was tested with sixteen case studies taken from the literature. The accuracy of the calculated parameters was also satisfactory for solvent selection, as demonstrated with a 1,4-addition reaction and a multicomponent heterocycle synthesis.

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Intelligent Approach to Solvent Substitution: The Identification of a New Class of Levoglucosenone Derivatives

Cited by 43 publications

References 46 publications

The green solvent: a critical perspective

The green solvent: a critical perspective

Bio‐available Solvent Cyrene: Synthesis, Derivatization, and Applications

A Method of Calculating the Kamlet–Abboud–Taft Solvatochromic Parameters Using COSMO-RS

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