Butylene chlorohydrin

Alkenes are converted to halohydrins by the treatment of halides and water. When halohydrins are treated with a strong base (NaOH), an intramolecular cyclization occurs and epoxides are formed. For example, 1-butene can be converted to butylene oxide via butylene chlorohydrin. 

See Butylenes Chlorohydrins Ethylene oxide Olefins Propylene oxide Styrenes. 

Chloro-2-butanol a-Butylene chlorohydrin C4H9CIO 1873-25-2 108.566 141 1.068" 1.4400 " s EtOH, eth... 

Bromphenol Blue 1315 a-Butylene chlorohydrin 1932 Capric alcohol 2758... 

Butylene Oxide. Butylene oxides are prepared on a small scale by Dow by chlorohydrin technology. There appears to be no technical reason why they could not be prepared by the propylene oxide Oxirane process (see Chlorohydrins). 

Isobutylene oxide is produced in a way similar to propylene oxide and butylene oxide by a chlorohydrination route followed by reaction with Ca(OH)2. Direct catalytic liquid-phase oxidation using stoichiometric amounts of thallium acetate catalyst in aqueous acetic acid solution has been reported. An isobutylene oxide yield of 82% could be obtained. 

A method of considerable industrial importance for the large-scale preparation of ethylene oxide is direct oxidation of ethylene at elevated temperatures over a suitably prepared metallic silver catalyst. Although the reaction may be written aa indicated in Eq. (09), in actual practice only about half the ethylene is converted into ethylene oxide, the remainder being oxidized further to carbon dioxide and water. In spite of this seeming disadvantage, catalytic oxidation appears at present to bo economically competitive with chlorohydrin formation aa a means for the commercial production of ethylene oxide.MM Unfortunately, other olefins, such as propylene and mo-butylene for example, apparently give only carbon dioxide and water under the usual oxidation conditions,1310 so that until now the patent hu balance ethylene oxide has been the only representative accessible by tins route. 

Smaller uses of 1-butene are in 1,2-butylene oxide, butyl mercaptan, and butyl phenols. Butylene oxide, produced by the chlorohydrin process, is used as a corrosion inhibitor in chlorinated solvents. Butyl mercaptan is a precursor for organophosphate herbicides, pharmaceutical intermediates, and is used as a gas odorant. 

Propylene oxide and 1,2-butylene oxide cyclic ethers find their largest use as chemical intermediates. Both oxides react readily with dilute amounts of mineral acids (e.g., hydrochloric acid) to form the chlorohydrin addition product. This reactivity with acid make these epoxy solvents valuable acid acceptor-type stabilizers for several chlorinated solvents. Trace amounts of hydrogen chloride from chlorinated solvent degradation is immediately neutralized by reaction with the propylene or 1,2-butylene oxide stabilizer. Reaction of propylene oxide with an alcohol or phenol in the presence of an acid catalyst yields the monoether of propylene glycol (see Chapter 13 for the glycol ethers). 

Butylene oxide, or 1,2-epoxybutane, is produced in the United States by Dow Chemical Company. The current production is about 8 million pounds (3,640 metric tons) per year by a chlorohydrin process similar to that used to make propylene oxide. It is available as 1,2-butylene oxide or as an 80-90/10-20 mixture of 1,2-and 2,3-butylene oxide. In Europe, 1,2-butylene oxide is manufactured principally by BASF. 

During the same period Universal Oil Products developed olefin polymerization and hydrogenation processes and the Shell Chemical Company became interested in olefin chemistry and petrochemicals. Shell opened its Emeryville, California, research center in 1928 and developed methods for the production of alcohols, ketones, and esters from propylene and butylenes, as well as synthetic chlorohydrins, glycols, and glycerol. Many of these petroleum chemicals were produced in Martinez, California, from 1933 and the use of petrochemical catalysts became established. 

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