Abstract
| 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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Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene™. / Bousfield, Thomas; Pearce, Katharine; Nyamini, Simbarashe; Angelis-Dimakis, Athanasios; Camp, Jason.
In: Green Chemistry, Vol. 21, No. 13, 07.07.2019, p. 3675-3681.Research output: Contribution to journal › Article
TY - JOUR
T1 - Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene™
AU - Bousfield, Thomas
AU - Pearce, Katharine
AU - Nyamini, Simbarashe
AU - Angelis-Dimakis, Athanasios
AU - Camp, Jason
PY - 2019/7/7
Y1 - 2019/7/7
N2 - 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.
AB - 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.
KW - Cyrene
KW - Green Solvents
KW - Amide
KW - Molar Efficiency
KW - Metrics Calculator
UR - http://www.scopus.com/inward/record.url?scp=85068394954&partnerID=8YFLogxK
U2 - 10.1039/c9gc01180c
DO - 10.1039/c9gc01180c
M3 - Article
VL - 21
SP - 3675
EP - 3681
JO - Green Chemistry
JF - Green Chemistry
SN - 1463-9262
IS - 13
ER -