EPICHLOROHYDRIN

CASRN: 106-89-8; DOT: 2023; DOT label: Flammable liquid and poison; molecular formula: C3H5ClO; FW: 92.53; RTECS: TX4900000; Merck Index: 12, 3648 Physical state, color, and odor: Clear, colorless, mobile liquid with a strong, irritating, chloroform-like odor. Odor threshold concentration is 0.93 ppm (quoted, Amoore and Hautala, 1983). Melting point (°C): -48 (Weast, 1986) Boiling point (°C): 116.5 (Weast, 1986) Density (g/cm3): 1.1820 at 20 °C (Vaidya and Naik, 2003) 1.1750 at 25 °C (Windholz et al., 1983) Diffusivity in water (x 10-5 cm2/sec): 1.02 at 20 °C using method of Hayduk and Laudie (1974) Flash point (°C): 33.9 (NIOSH, 1997) 31 (open cup, NFPA, 1984) Lower explosive limit (%): 3.8 (NIOSH, 1997) Upper explosive limit (%): 21.0 (NIOSH, 1997) Henry’s law constant (x 10-5 atm⋅m3/mol): 3.42 at 25 °C (static headspace-GC, Welke et al., 1998) Ionization potential (eV): 10.60 (NIOSH, 1997) Soil organic carbon/water partition coefficient, log Koc: 1.00 (calculated, Mercer et al., 1990) Octanol/water partition coefficient, log Kow: 0.45 (shake flask-GLC, Deneer et al., 1988)

Soluble in benzene (Weast, 1986). Miscible with alcohol, carbon tetrachloride, chloroform, ether, and tetrachloroethylene (Windholz et al., 1983). Solubility in water (g/L at 20 °C): 60 (quoted, Verschueren, 1983) 65.8 (quoted, Riddick et al., 1986) Vapor density: 3.78 g/L at 25 °C, 3.19 (air = 1) Vapor pressure (mmHg): 12.5 at 20 °C (Hawley, 1981) 16.5 at 25 °C (Lide, 1990) Environmental fate: Biological. Bridié et al. (1979) reported BOD and COD values of 0.03 and 1.16 g/g using filtered effluent from a biological sanitary waste treatment plant. These values were determined using a standard dilution method at 20 °C for a period of 5 d. When a sewage seed was used in a separate screening test, a BOD value of 0.16 g/g was obtained. The ThOD for epichlorohydrin is 1.21 g/g. Chemical/Physical. Anticipated products from the reaction of epichlorohydrin with ozone or OH radicals in the atmosphere are formaldehyde, glyoxylic acid, and ClCH2O(O)OHCHO (Cupitt, 1980). Haag and Yao (1992) reported a calculated OH radical rate constant in water of 2.9 x 108/M⋅sec. Hydrolyzes in water forming 1-chloro-2,3-hydroxypropane which may hydrolyze forming HCl and the intermediate 1-hydroxy-2,3-propylene oxide or 1-chloro-2,3-hydroxypropane. The oxide may continue to hydrolyze forming glycerol (Kollig, 1993). The estimated half-life for this reaction at 20 °C and pH 7 is 8.2 d (Mabey and Mill, 1978). Emits toxic fumes when heated to decomposition. Exposure limits: Potential occupational carcinogen. NIOSH REL: IDLH 75 ppm; OSHA PEL: TWA 5 ppm (19 mg/m3); ACGIH TLV: TWA 0.5 ppm (adopted). Symptoms of exposure: Irritation of eyes, skin, and respiratory tract (Patnaik, 1992) Toxicity: LC50 (14-d) for Poecilia reticulata 655 µg/L (Hermens et al., 1985). LC50 (96-h static bioassay) for bluegill sunfish 35 mg/L, Menidia beryllina 18 mg/L (quoted, Verschueren, 1983). LC50 (48-h) for harlequin fish 36 mg/L (static and flow through). Acute oral LD50 for guinea pigs 280 mg/kg, mice 194 mg/kg, rats 90 mg/kg, rabbits 345 mg/kg (quoted, Verschueren, 1983). Drinking water standard (final): MCLG: zero; MCL: lowest feasible limit following conventional treatment. In addition, a DWEL of 70 µg/L was recommended (U.S. EPA, 2000). Uses: Solvent for natural and synthetic resins, paints, cellulose esters and ethers, gums, paints, varnishes, lacquers, and nail enamels; manufacturing of glycerol, epoxy resins, surface active agents, pharmaceuticals, insecticides, adhesives, coatings, plasticizers, glycidyl ethers, ionexchange resins, and fatty acid derivatives; organic synthesis.