Abstract
Cyrene™ as a bio-alternative dipolar aprotic solvent: a waste minimizing and molar efficient protocol for the synthesis of amides from acid chlorides and primary amines in the bio-available solvent Cyrene™ is disclosed. This protocol removed the use of toxic solvents, such as dimethylformamide and dichloromethane. A simple aqueous work-up procedure for the removal of the high boiling solvent Cyrene™ resulted in up to a 55-fold increase in molar efficiency (Mol E.%) versus standard operating procedures. In order to rapidly compare the molar efficiency of this process against other methodologies an Excel based Mol. E% calculator was developed that automates many of the calculations. An investigation into the hydration of Cyrene™ found that it readily hydrates to form a geminal diol in the presence of water and that this process is exothermic.
| Original language | English |
|---|---|
| Pages (from-to) | 3675-3681 |
| Number of pages | 7 |
| Journal | Green Chemistry |
| Volume | 21 |
| Issue number | 13 |
| Early online date | 17 Jun 2019 |
| DOIs | |
| Publication status | Published - 7 Jul 2019 |
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Profiles
Athanasios Angelis-Dimakis
- Department of Chemical Sciences - Senior Lecturer in Chemical Engineering
- School of Applied Sciences
- Biorefinery Engineering and Bioprocessing Research Centre - Member
- Technical Textiles Research Centre - Member
- Chemical Synthesis and Design Centre - Associate Member
- Centre for Human and Physical Geography - Associate Member
Person: Academic
Cite this
Bousfield, T., Pearce, K., Nyamini, S., Angelis-Dimakis, A., & Camp, J. (2019). Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene™. Green Chemistry, 21(13), 3675-3681. https://doi.org/10.1039/c9gc01180c