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Glymes "Glycol Diethers" and Specialty Solvents

Glymes, also known as glycol diethers, are some of the most powerful solvents available today for an incredibly wide variety of industrial processes and products. Glymes are saturated polyethers with no functional groups; hence, they are aprotic compounds that are relatively inert chemically. These features account for their excellent solvent properties. For example, most glymes are completely miscible with both water and hydrocarbon solvents. Like other oxygen-containing solvents, they tend to solvate cations. This leaves anions active, so that for reactions involving basic reagents, the use of glymes as solvents and reaction media can greatly enhance reaction rates.

This all-ether structure produces only weak associations between glyme molecules and is responsible for the low viscosity of these materials, an important plus in many applications.

A further structural feature of the glymes that contributes significantly to their usefulness involves the arrangement of oxygen atoms, as ether linkages, at small and regular intervals. The structure (pictured below) illustrates this periodic recurrence of oxygen atoms separated by two carbon atoms. This stearic arrangement, analogous to that of interesting but expensive crown ethers, give glymes the ability to form complexes with many cations.

In general, glymes are most frequently used in reactions involving metals, inorganic salts and organometallics. Common examples are grignard reactions, reactions of alkali metals, anionic polymerization, metal hydride reactions and hydrobrominations.