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CAPLUS COPYRIGHT 2011 ACS
||Preparation of chlorohydrin by hydrochlorination of glycerin with reduced volatile chlorinated hydrocarbon by-products and chloracetone levels
||Kruper, William J.; Arrowood, Tina; Bell, Bruce Michael; Briggs, John; Campbell, Robert M.; Hook, Bruce D.; Nguyen, Anh; Theriault, Curt; Fitschen, Ralf
||Dow Deutschland GmbH & Co. OHG, Germany; Dow Global Technologies Inc.
||U.S. Pat. Appl. Publ., 27 pp., Cont.-in-part of U.S. Ser. No. 628,269. CODEN: USXXCO
The invention relates to a process for converting a multihydroxylated-aliphatic hydrocarbon or ester to a chlorohydrin, by contacting the multihydroxylated-aliphatic hydrocarbon or ester with hydrogen chloride at superatmospheric, atmospheric and subatmospheric pressure conditions for a sufficient time and at a sufficient temperature, preferably wherein such contracting step is carried out without substantial removal of water, to produce the desired chlorohydrin product; wherein the desired product or products can be made in high yield without substantial formation of undesired overchlorinated byproducts; said process carried out without a step undertaken to specifically remove volatile chlorinated hydrocarbon byproducts or chloroacetone, wherein the combined concentration of volatile chlorinated hydrocarbon byproducts and chloroacetone is <2000 ppm throughout any stage of the said process. Thus, glycerol 30.0 and glacial acetic acid 4.5 g was mixed with anhydroous hydrogen chloride gas in a 100 mL Parr reactor at pressure of 90 psig, and heated at 93ｰ for 90 min to give 65.9 g product comprising 1,3-dichloropropan-2-ol and its acetate ester 92.6 mol%, 2,3-dichloropropan-1-ol and its acetate ester 1.7 mol%. The invention also relates to a process for preparing an epoxide comprising the steps of: (a) contacting glycerin, an ester glycerin, or a mixture thereof with hydrogen chloride source at superatmospheric pressure to produce a chlorohydrin, said contacting step carried out without substantial removal of water; and (b) contacting the chlorohydrin formed in step (a) above with a base to form an epoxide; wherein the combined concentration of volatile chlorinated hydrocarbon byproducts and chloroacetone is less than 2000 ppm throughout any stage of the said process.
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