Divinyl ether
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| Routes of administration |
inhalation |
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| Excretion | pulmonary |
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| ECHA InfoCard | 100.003.383 |
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| Formula | C4H6O |
| Molar mass | 70.0898 g/mol |
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Vinyl ether, also known as divinyl ether, divinyl oxide, Vinethene (pharmaceutical trade name) and ethenoxyethene (IUPAC), is a clear, nearly colorless, volatile liquid which was briefly used as an inhalation anesthetic. It can be cyclopolymerized by itself and serves as a cross-linker in copolymerizations.
Much to the dismay of some pharmacologists, the synthesis and isolation of pure vinyl ether proved to be a difficult challenge for chemists; vinyl ether was suspected to be a nearly ideal anesthetic as its structure was the combination of an alkene and an ether. In practice, vinyl ether proved to have favorable properties that allowed its brief usage as an anesthetic; on the other hand, it left many unimpressed. Aggravated by the issue of potentially toxic degradation over long-term storage and possible hepatic toxicity, vinyl ether began to leave the operating theater. Today, vinyl ether is a relic in the field of anesthesiology; however, the analytical techniques used to study its pharmacology laid the groundwork for the testing of new anesthetic agents.
The first preparation of vinyl ether was reported in 1887 by Semmler. (Major, 1935) This chemist reported the production of vinyl ether from its sulfur substituted analogue, divinyl sulfide (obtained from the essential oil of Allium Ursinum L.), by reaction with silver oxide. Semmler's product which boiled at 39 °C was found to be sulfur free and molecular weight determinations were theoretically in accordance with vinyl ether.
In 1899, Knorr and Matthes attempted a synthesis of vinyl ether by exhaustive methylation of morpholine. (Major, 1935) They attained such a small quantity of product that no characterization was possible.
Cretcher et al. reported, in 1925, what would become the foundation for one industrial method used to produce vinyl ether. It was stated that the action of heated sodium hydroxide upon β,β`-dichlorodiethyl ether produced a liquid boiling at 39 °C (among other identified products). (Major, 1935) However, in a subtly modified process Hibbert et al. reported the isolation of a product boiling at 34-35 °C, "divinyl ether". Finally, in 1929, a patent issued to Merck & Co reported isolation of vinyl ether boiling ca. 28 °C. The currently accepted boiling point of vinyl ether is 28.3 °C; the Merck patent, therefore, was the first to report the isolation of a pure product.
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