Chlorohydrines

HOCHj CHjOH. Colourless, odourless, rather viscous hygroscopic liquid having a sweet taste, b.p. 197 C. Manufactured from ethylene chlorohydrin and NaHC03 solution, or by the hydration of ethylene oxide with dilute sulphuric acid or water under pressure at 195°C. Used in anti-freezes and coolants for engines (50 %) and in manufacture of polyester fibres (e.g. Terylene) and in the manufacture of various esters used as plasticizers. U.S. production 1979 1 900 000 tonnes. 

CH3 CH0H CH20H, a colourless, almost odourless liquid. It has a sweet taste, but is more acrid than ethylene glycol b.p. 187. Manufactured by heating propylene chlorohydrin with a solution of NaHCO under pressure. It closely resembles dihydroxyethane in its properties, but is less toxic. Forms mono-and di-esters and ethers. Used as an anti-freeze and in the preparation of perfumes and flavouring extracts, as a solvent and in... 

Glycerol (i-monochlorohydrin, 2-chloru-trimelhylene glycol, 1,3-dihydroxy-2-chlorO propane, CH2 0H CHC1 CH2 0H. Colourless liquid b.p. 146"C/18mm. It is obtained in small amounts in the preparation of the x-chlorohydrin. 

Both of these chlorohydrins are converted to 1,2-dihydroxypropane by heating with solutions of sodium hydrogen carbonate when heated with solid sodium hydroxide they give 1,2-epoxypropane. U.S. production 1976 4400 tonnes. 

BrCHisCHjBr + 2NaOH —> HOCHjCHisOH + 2NaBr Industrially, it is produced directly from ethylene by the addition of hypo, chlorous acid, followed by treatment of the resulting ethylene chlorohydrin with sodium bicarbonate solution ... 

ClCHjCHjOH + NaHCOj —> HOCHjCHjOH + COj + NaCl When ethylene chlorohydrin is heated with sodium hydroxide solution, the highly reactive cyclic ether, ethylene oxide, is formed ... 

Methyl acrylate is usually prepared from ethylene chlorohydrin thus ... 

Chlorohydrin 61 is formed by the nucleophilic addition to ethylene with PdCl2 and CuCl2[103,104]. Regioselective chlorohydroxylation of the allylic amine 62 is possible by the participation of the heteroatom to give chlorohydrin 63. Allylic sulfides behave similarly[105]. 

Tetrahydrofurfuryl alcohol is used in elastomer production. As a solvent for the polymerization initiator, it finds appHcation in the manufacture of chlorohydrin mbber. Additionally, tetrahydrofurfuryl alcohol is used as a catalyst solvent-activator and reactive diluent in epoxy formulations for a variety of apphcations. Where exceptional moisture resistance is needed, as for outdoor appHcations, furfuryl alcohol is used jointly with tetrahydrofurfuryl alcohol in epoxy adhesive formulations. 

In the early versions, ethylene cyanohydrin was obtained from ethylene chlorohydrin and sodium cyanide. In later versions, ethylene oxide (from the dkect catalytic oxidation of ethylene) reacted with hydrogen cyanide in the presence of a base catalyst to give ethylene cyanohydrin. This was hydrolyzed and converted to acryhc acid and by-product ammonium acid sulfate by treatment with about 85% sulfuric acid. 

---