(107b) Guanidine/alcohol and Amidine/alcohol Switchable Solvent Mixtures

Huttenhower, H. A., Georgia Institute of Technology
Phan, L., Queen's University
Chiu, D., Queen's University
Heldebrant, D. J., Queen's University
John, E. A., Georgia Institute of Technology
Li, X., Queen's University
Pollet, P., Georgia Institute of Technology, Specialty Separations Center
Eckert, C., Georgia Institute of Technology
Liotta, C. L., Georgia Institute of Technology
Jessop, P. G., Queen's University

Organic solvents are a crucial part of chemistry on both a laboratory and an industrial scale. However, because solvents have very fixed properties, they often need to be removed and replaced between different steps of a reaction. This leads to an increase of economic cost and environmental impact for many processes. Developing a switchable solvent that can reversibly change its nature and properties at mild conditions would help solve this problem. Examples of solvents that consist of either a mixture of an amidine and alcohol or a guanidine and alcohol have been developed that form high polarity ionic liquids when exposed to CO2 at atmospheric pressure. Furthermore, these ionic liquids can be reversed back to a low polarity neutral form by exposure to nitrogen or mild heating. Such liquids have been used as a reaction medium utilizing their ?built-in? facile separation.