Intelligent approach to solvent substitution: the identification of a new class of levoglucosenone derivatives

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


With the increasing restriction and control of hazardous solvents, safer alternatives need to be identified. Here a contemporary approach to solvent selection and substitution is presented that offers a more scientific alternative to the simple “like-for-like” exchange. A new family of levoglucosenonederived compounds is proposed, modeled to determine their solvent properties, synthesized, and tested. These new molecules show promise as replacements for polar aprotic solvents that have chronic toxicity issues, such as dichloromethane, nitrobenzene, and N-methylpyrrolidinone. The success of this approach makes it possible for academia and industry to make calculated, intelligent choices for solvent substitution in the future.

Original languageEnglish
Pages (from-to)3503-3512
Number of pages10
Issue number24
Early online date17 Nov 2016
Publication statusPublished - 20 Dec 2016

Bibliographical note

© 2016, Wiley-VCH. 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


  • biomass
  • green chemistry
  • molecular modeling
  • solvatochromism
  • solvent effects

Cite this