Generation and Trapping of Ketenes in Flow
Cyril Henry1, David Bolien1, Bogdan Ibanescu1, Sally Bloodworth1, David C. Harrowven1, Xunli Zhang2, Andy Craven3, Helen F. Sneddon3, Richard J. Whitby1 *
- 1 Chemistry, University of Southampton, Southampton, HANTS, SO17 1BJ, UK,
- 2 Bioengineering Group, Faculty of Engineering and the Environment, University of Southampton, Southampton, HANTS, SO17 1BJ, UK
- 3 GlaxoSmithKline R&D Ltd., Medicines Research Centre, Gunnels Wood Road, Stevenage, HERTS, SG1 2NY, UK
Read the publication that featured this abstractKetenes were generated by the thermolysis of alkoxyalkynes under flow conditions, and then trapped with amines and alcohols to cleanly give amides and esters. For a 10 min reaction time, temperatures of 180, 160, and 140 °C were required for >95 % conversion of EtO, iPrO, and tBuO alkoxyalkynes, respectively. Variation of the temperature and flow rate with inline monitoring of the output by IR spectroscopy allowed the kinetic parameters for the conversion of 1-ethoxy-1-octyne to be easily estimated (Ea = 105.4 kJ/mol). Trapping of the in-situ-generated ketenes by alcohols to give esters required the addition of a tertiary amine catalyst to prevent competitive [2+2] addition of the ketene to the alkoxyalkyne precursor.
Get in touch
For more information on flow chemistry systems and services please use the contact methods below.
Call us on +44 (0)1284 728659 or Email us
Resource Centre
R-Series

The Vapourtec R-Series is, quite simply, unrivalled for flow chemistry
- Flexible |
- Precise |
- Automatable
The R-Series is undoubtedly the most versatile, modular flow chemistry system available today.
E-Series

The Vapourtec E-Series is the perfect introductory system for flow chemistry
- Robust |
- Easy to use |
- Affordable
The E-Series is a robust and affordable, entry level flow chemistry system designed for reliability and ease of use.