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Chloral is produced commercially by the chlorination of acetaldehyde in the presence of hydrochloric acid, producing chloral hydrate. Ethanol can also be used as a feedstock. This reaction is catalyzed by antimony trichloride: H 3 CCHO + 3 Cl 2 + H 2 O → Cl 3 CCH(OH) 2 + 3 HCl. The chloral hydrate is distilled from the reaction mixture.
Chloral hydrate is a geminal diol with the formula Cl 3 C−CH(OH) 2. It was first used as a sedative and hypnotic in Germany in the 1870s. Over time it was replaced by safer and more effective alternatives but it remained in usage in the United States until at least the 1970s. [ 4 ]
Melzer's reagent is an aqueous solution of chloral hydrate, potassium iodide, and iodine.Depending on the formulation, it consists of approximately 2.50-3.75% potassium iodide and 0.75–1.25% iodine, with the remainder of the solution being 50% water and 50% chloral hydrate.
Chloroethane is produced by hydrochlorination of ethylene: [11]. C 2 H 4 + HCl → C 2 H 5 Cl. At various times in the past, chloroethane has also been produced from ethanol and hydrochloric acid, from ethane and chlorine, or from ethanol and phosphorus trichloride, but these routes are no longer economical.
Similarly, the conversion of chloral (Cl 3 C)HC =O to chloral hydrate is strongly favored by influence of the trichloromethyl group. In some cases, such as decahydroxycyclopentane and dodecahydroxycyclohexane, the geminal diol is stable while the corresponding ketone is not.
The pharmacological effects of this compound in humans are similar to those of its prodrug chloral hydrate, and of chlorobutanol. Historically, it has been used as a sedative hypnotic. [3] The hypnotic drug triclofos (2,2,2-trichloroethyl phosphate) is metabolized in vivo to 2,2,2-trichloroethanol. Chronic exposure may result in kidney and ...
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Because this reaction is highly exothermic (238 kJ/mol), the temperature is monitored, to guard against thermal degradation of the catalyst. The reaction is as follows: CH 2 =CH 2 + 2 CuCl 2 → 2 CuCl + ClH 2 C-CH 2 Cl. The copper(II) chloride is regenerated by sequential reactions of the cuprous chloride with oxygen and then hydrogen chloride: