2-Chloro-l-propanol

In the synthesis of AGE with an acid as the catalyst, aHyl alcohol is added to the epoxy group of epichlorohydrin, yielding 3-aHyloxy-l-chloro-2-propanol [4638-03-3], which then undergoes cyclization with alkaU to yield AGE. Catalysts such as H2SO4, SnCl, BE (C2H )20 (33), heteropolyacids, HQO, andy -CH CgH SO H (34) are used. 

The l-chloro-2-propanol isomer represents about 85% of the chlorohydrin produced. In order to minimise the formation of dichlotide coproduct and ether, the reactant compositions are chosen such that the effluent Hquid contains 4—5 wt % propylene chlorohydrin. Under these conditions, the yield of chlorohydrin, dichloride, and ether from the reactants is reported to be 87—90, 6—9, and 2%, respectively (109,110,112). 

Hydrogen hahdes normally add to form 1,2-dihaLides, though an abnormal addition of hydrogen bromide is known, leading to 3-bromo-l-chloropropane [109-70-6], the reaction is beUeved to proceed by a free-radical mechanism. Water can be added by treatment with sulfuric acid at ambient or lower temperatures, followed by dilution with water. The product is l-chloro-2-propanol [127-00-4]. 

Table 2 gives physical property data for propylene chlorohydrins. 2-Chloro-l-propanol [78-89-7] HOCH2CHCICH2, is also named 2-propylene chlorohydrin, 2-chloropropyl alcohol, or 2-chloro-l-hydroxypropane. l-Chloro-2-propanol [127-00-4] CICH2CHOHCH2, also known as j -propjlene chlorohydrin, 1-chloroisopropyl alcohol, and l-chloro-2-hydroxypropane, is a colorless Hquid, miscible in water, ethanol, and ethyl ether. 

Hydrolysis to Glycols. Ethylene chlorohydrin and propylene chlorohydrin may be hydrolyzed ia the presence of such bases as alkaU metal bicarbonates sodium hydroxide, and sodium carbonate (31—33). In water at 97°C, l-chloro-2-propanol forms acid, acetone, and propylene glycol [57-55-6] simultaneously the kinetics of production are first order ia each case, and the specific rate constants are nearly equal. The relative rates of solvolysis of... 

Formation of Cyclic Carbonates. In the absence of water, chlorohydrins such as 2-chloroethanol and l-chloro-2-propanol react with an alkah carbonate or bicarbonate to produce cycHc carbonates such as ethylene carbonate [96-49-1] and propylene carbonate [108-32-7] ia yields of up to 80%... 

Ghlorohydrination in Chlorine and Water. The hypochlotination of propylene gives two isomers 90% l-chloro-2-propanol and 10% 2-chloro-1-propanol. 

Synthesis of the intermediate aminonitrile for methadone by (I r giospecific route served to confirm the structure. Alkyla-I Lon of diphenylacetonitrile with l-chloro-2-propanol affords the. ilcohol, 120, free of isomeric products (although it is possible here, too, to imagine cyclization of the halide prior to alkyla-lion). The hydroxyl is then converted to the bromide (121) by... 

The one general exception to the rule that ethers don t typically undergo Sn2 reactions occurs with epoxides, the three-membered cyclic ethers that we saw in Section 7.8. Epoxides, because of the angle strain in the three-membered ring, are much more reactive than other ethers. They react with aqueous acid to give 1,2-diols, as we saw in Section 7.8, and they react readily with many other nucleophiles as well. Propene oxide, for instance, reacts with HC1 to give l-chloro-2-propanol by Snj2 backside attack on the less hindered primary carbon atom. We ll look at the process in more detail in Section 18.6. 

Jacobsen (1999) has carried out carbomethoxylation of asymmetric epoxides. Thus, the carbomethoxylation of (R)-propylene oxide with CO and methanol yields 92% of (3R)-hydroxybutanoic acid in greater than 99% ee. Similarly, the reaction of (/ )-epichlorohydrin gives 96% of 4-chloro-(3R)-hydroxybutanoic acid in greater than 99% ee. The catalyst consists of dicobalt octacarbonyl and 3-hydroxy pyridine. A continuous process for making enantiomeric 1-chloro-2-propanol has been suggested. With a suitable catalyst propylene reacts with O2, water, cupric and lithium chloride to give 78% of (S)-l-chloro-2-propanol in 94% ee. 

C12 to C20, primarily Ci6 to ( is), used as surface lubricants in the manufacture of food-contact articles. The method, which uses ethyl palmitate (Eastman Chemicals No. 1575 Red Label) as an internal standard, has been validated at 200 ppm total FAME [185]. Other FAME standards (methyl palmitate, methyl stearate, methyl oleate, methyl linoleate and methyl linolenate) are available (Applied Science Laboratories) [116], Worked out examples of additive determinations are given in the Food Additives Analytical Manual [116], which also describes a great many of indirect food additives, such as BHA, BHT, TBHQ, l-chloro-2-propanol, DLTDP, fatty acid methyl esters, w-heptyl-p-hydroxybenzoate, propyl-gallate, sodium benzoate, sodium stearoyl-2-lactylate, sorbitol and phenolic antioxidants. EPA methods 606 and 8060 describe the CGC separation of phthalate esters (direct injection) (cf. Figure 4.2). 

Chemical/Physical. Hydrolysis in distilled water at 25 °C produced l-chloro-2-propanol and HCl. The reported half-life for this reaction is 23.6 yr (Milano et al., 1988). The hydrolysis rate constant for 1,2-dichloropropane at pH 7 and 25 °C was determined to be 5 x 10 Vh, resulting in a half-life of 15.8 yr. The half-life is reduced to 24 d at 85 °C and pH 7.15 (Ellington et al., 1987). A volatilization half-life of 50 min was predicted from water stirred in an open container of depth 6.5 cm at 200 rpm (Dilling et al., 1975). Ozonolysis yielded carbon dioxide at low ozone concentrations (Medley and Stover, 1983). 

Steele, W.V., Chirico, R.D., Knipmeyer, S.E., and Nguyen, A. Vapor pressure, heat capacity, and density along the saturation line measurements for benzenamine,butylbenzene, sec-butylbenzene, ferf-butylbenzene, 2,2-dimethylbutanoic acid, trideca-fluoroheptanoic acid, 2-butyl-2-ethyl-l, 3-propanediol, 2,2,4-trimethyl-l, 3-pentanediol, and l-chloro-2-propanol, J. Chem. Eng. Data, 47(4) 648-666, 2002a. 

Betanechol Betanechol, 2-carbamoyloxy-l-(A,A,iV-trimethyl)propyl ammonium chloride (13.1.8), is made by either the subsequent reaction of l-(iV,A,A-trimethylammonium) propan-2-ol with phosgene, followed by ammonia, or by a completely analogous synthesis of carbachol by the reaction of l-chloro-2-propanol with phosgene followed by consequent reactions with ammonia, and then with trimethylamine, giving betanechol (13.1.8) [14,15],... 

The preparation of l-azido-2-propanol (0.49 mole) from l-chloro-2-propanol and sodium azide (0.51 mole) in 33% aqueous methanol (by volume) has been reported to give a 55 % yield [9a]. 

In an older version of the synthesis, propylene and chlorine react in an aqueous solution to form propylene chlorohydrin.192-194 The slightly exothermic reaction maintains the 30-40°C reaction temperature to yield isomeric propylene chlorohy-drins (l-chloro-2-propanol/2-chloro-1-propanol = 9 1). The main byproduct is 1,2-dichloropropane formed in amounts up to 10%. The product propylene chlorohydrin then undergoes saponification to propylene oxide with calcium hydroxide or sodium hydroxide. 

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). 

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