15-Crown-5

Chemical properties

colourless liquid

The Uses of 15-Crown-5

15-Crown-5 is used as an efficient phase transfer catalyst and as a complexing agent. It is used to isolate oxonium ion (H7O3)+ salts especially from a solution of tetrchloroauric acid. It catalyzes the O-alkylation of the sodium salts of carboxylic acids in the penicillin and cephalosporin series, thereby facilitating esterification reaction without usage of acid. It is also used to facilitate the Williamson synthesis of ethers with hindered alcohols and sodium hydride. It is used with lithium aluminum hydride, for performing reduction reactions in hydrocarbon solvents. Further, it is involved in the Horner-Wadsworth-Emmons reaction to prepare stilbenes from aldehydes.

Definition

ChEBI: A saturated organic heteromonocyclic parent that is cyclopentadecane in which the carbon atoms at positions 1, 4, 7, 10 and 13 have been replaced by oxygen atoms to give a crown ether.

General Description

15-Crown-5 is a crown ether generally used as a ligand in coordination chemistry because of its strong chelating property with certain alkali cations to form complexes. Some derivatives of 15-crown-5 are used as sensors and probes in different physical-chemical processes, phase-transfer reactions, and selective capture of ions for separation and transport.

Safety Profile

Moderately toxic by ingestion, skin contact, and intraperitoneal routes. A skin and eye . When heated to decomposition it emits acrid smoke and irritating fumes

Purification Methods

Dry it over 3A molecular sieves and distil it in a high vacuum. [Beilstein 19/12 V 252.]