3- Chloro-l,2-propanediol

HVP products prepared by hydrolysis with HCl contain varying amounts of glycerol chlorohydrins, such as 3-chloro-l,2-propanediol [96-24-2] and l,3-dichloro-2-propanol [96-23-1J, depending on reaction conditions and Hpid contents of the starting material (135). As a result of their toxicides, regulating agencies in many countnes have restncted the contents of these compounds in food. 

Chloro-l,2-propanediol [96-24-2] HOCH2CHOHCH2CI, a liquid with = 1.4831 (6), boils at 213°C and 101.3 kPa (1 atm) with decomposition. It can be distilled at 114—120°C at 1.87 kPa (14 mm Hg). Synonyms for this compound include 3-chloro-l,2-dihydroxypropane, glycerol monochlorohydrin, a-chlorohydrin, and 3-chloropropylene glycol. It is miscible in water, ethanol, ethyl ether, and acetone [67-64-1] (8) and is soluble in hot... 

From Glycerol. A procedure for synthesizing alph a-m on ochl orohydrin (3-chloro-l,2-propanediol) in 85—88% yields by the reaction of glycerol [56-81-5] with aqueous hydrochloric acid in the presence of a catalytic amount of acetic acid has been developed (59). An anhydrous procedure that involves the reaction of glycerol and HCl gas in the presence of acetic acid has also been described (60). 

The merchant market for chi orohydrin s is small, primarily for specialty appHcations. Ethylene chlorohydrin is sold ia the United States by BASF Corp., Parsippany, N.J., available ia 230 kg net lined steel dmms. Glycerol monochlorohydrin (3-chloro-l,2-propanediol) is available from Dixie Chemical Co., Houston, Tex., in lined steel dmms (227.3 kg net) from Raschig Corp., Richmond, Va. and from Henley Chemicals, Inc., Montvale, N.J., ia steel dmms (240 kg net). Glycerol dichi orohydrin (l,3-dichloro-2-propanol) is not currentiy being produced for the U.S. merchant market but has been available ia the past at a selling price of 5—6/kg. 

Degradation of epichlorohydrin (l-chloro-2,3-epoxypropane) may proceed by hydrolysis of the epoxide to 3-chloro-l,2-propanediol that is then converted successively into... 

Chloro-l,2-propanediol [96-24-2] C1CH2CH0HCH20H Perchloric acid See Perchloric acid Glycols, etc. (reference 1) C3H7C102... 

Reactions catalyzed by enzymes or enzyme systems exhibit far greater specificities than more conventional organic reactions. Among these specificities which enzymatic reactions possess, stereospecificity is one of the most excellent. To overcome the disadvantage of a conventional synthetic process, i.e., the troublesome resolution of a racemic mixture, microbial transformation with enzymes possessing stereospecificities has been appHed to the asymmetric synthesis of optically active substances [1-10]. C3- and C4-synthetic units (synthons, building blocks), such as epichlorohydrin (EP), 2,3-dichloro-l-propanol (2,3-DCP), glycidol (GLD), 3-chloro-l,2-propanediol (3-CPD), 4-chloro-... 

The absorption and elimination of epichlorohydrin in mice are rapid after oral administration. The diol metabolite, 3-chloro-l,2-propanediol, was detected in plasma (Rossi et al., 1983a). 

For alcohols, EHOMO decreases as the number of chlorines increases. The dataset is l-chloro-2-propanol 2,2/2-trichloro-l/l-ethanediol 2,2,2-trichloro-ethanol 2,2-dichloroethanol 2-chloroethanol 3-chloro-l,2-propanediol 3-chloropropanol and 4-chloro-l-butanol. HOMO represents 94.4% of the variance in the linear regression equation therefore, the probability of getting a correlation of -0.9721 for a sample size of eight is less than 1% (see Figure 5.17). 

S-(+)-3-Chloro-l,2-propanediol Methanesulfonyl chloride Potassium t-butoxide 4-Nitrobenzenesulfonyl chloride Hydrochloric acid Diisopropylethylamine Benzyl chloroformate... 

Tetrahydrofuran (3.2 ml) and S-(+)-3-chloro-l,2-propanediol (0.299 ml, 3.58 mmol, 1.19 eq) are mixed. The mixture of THF (3.2 ml) and S-(+)-3-chloro-1,2-propanediol (0.299 ml, 3.58 mmol, 1.19 eq) is cooled to -16°C and potassium t-butoxide (3.2 ml, 1.0 M) in THF (3.2 mmol, 1.07 eq) is added at less than -10°C. The resulting slurry is stirred at -14-0°C for 1 hour. Then added to the lithium anion mixture while maintaining both mixtures at 0°C, then rinsed in with THF (2 ml). The resultant slurry is stirred at 20-23°C for 2 hour and then cooled to 6°C and a mixture of citric acid monohydrate (0.4459 g, 2.122 mmol, 0.705 eq) in water (10 ml) is added. The resultant liquid phases are separated and the lower aqueous phase is washed with ethyl acetate (12 ml). The organic layers are combined and solvent is removed under reduced pressure until a net weight of 9.73 g remains. Heptane (10 ml) and water (5 ml) are added and solvent is removed 4-nitrobenzenesulfonyl chloride y reduced pressure until a total volume of 5 ml remains. The precipitated product is collected by vacuum filtration and washed with water (7 ml). The solids are dried in a stream of nitrogen to give (R)-[N-3-(3-fluoro-4-(4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methanol. 

The hydrolysis product of ECH in neutral and acidic aqueous media is 3-chloro-l,2-propanediol and at high pH values the reaction proceeds up to the formation of glycerine (Fig. 10-14). 

CHLOROPROPANE-l,2-DIOL see CDT750 3-CHLORO-l,2-PROPANEDIOL see CDT750 CHLOROPROPANEDIOL CYCUC SULFITE see CKQ750... 

Monothioglycerol is prepared by heating an ethanolic solution of 3-chloro-l,2-propanediol with potassium bisulfide. 

N. Kasai, T. Suzuki, Production of Chiral C3 and C4 Units via Microbial Resolution of 2,3-Dichloro-l-propanol, 3-Chloro-l,2-propanediol and Related Halohydrins, in H. U. Blaser, E. Schmidt (Eds.), Asymmetric Catalysis on Industrial Scale,Wiley-VCH,Weinheim, 2004,... 

Production of Chiral C3 and C4 Units via Microbial Resolution of 2,3-Dichloro-l-propanol, 3-Chloro-l,2-propanediol and Related Halohydrins... 

The study and development of microbial methods for the industrial-scale production of C3 and C4 chiral synthetic units such as 2,3-dichloro-l-propanol (DCP), epichloro-hydrin (EP), 3-chloro-l,2-propanediol (CPD), glycidol (GLD), 4-chloro-3-hydroxy-butyrate (CHB), 3-hydroxy-y-butyrolactone (HL) is described. The following points are emphasized overall strategy screening, isolation, and cultivation of bacteria control of fermentation reactions and transfer from lab- to production-scale. 

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