ABSTRACT
Cl Cl CASRN: 72-54-8; DOT: 2761; DOT label: Poison; molecular formula: C14H10Cl4; FW: 320.05; RTECS: KI0700000; Merck Index: 12, 3111 Physical state and color: Crystalline white solid Melting point (°C): 107-109 (Aldrich, 1990) Boiling point (°C): 193 (Sax, 1985) Density (g/cm3): 1.476 at 20 °C (Weiss, 1986) Diffusivity in water (x 10-5 cm2/sec): 0.45 at 20 °C using method of Hayduk and Laudie (1974) Flash point (°C): Not pertinent (Weiss, 1986) Lower explosive limit (%): Not pertinent (Weiss, 1986) Upper explosive limit (%): Not pertinent (Weiss, 1986) Henry’s law constant (x 10-6 atm⋅m3/mol): 6.62 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) 3.27 at 5 °C, 5.63 at 15 °C, 7.30 at 20 °C, 9.47 at 25 °C, 20.7 at 35 °C; in 3% NaCl solution: 3.95
at 5 °C, 7.70 at 15 °C, 15.8 at 25 °C, 27.6 at 35 °C (gas stripping-GC, Cetin et al., 2006) Bioconcentration factor, log BCF: 4.92 (fish, microcosm) (Garten and Trabalka, 1983) 2.79 (alga), 3.65 (snail), 3.43 (carp) (quoted, Verschueren, 1983)
oc 5.12 (Taichung soil: pH 6.8, % sand: 25, % silt: 40, % clay: 35) (Ding and Wu, 1995) 5.38 (Jury et al., 1987) 6.6 (average using 9 suspended sediment samples from the St. Clair and Detroit Rivers, Lau et al.,
1989) Octanol/water partition coefficient, log Kow: 5.99 (Callahan et al., 1979) 5.061 (Rao and Davidson, 1980) 5.80 (estimated using HPLC, DeKock and Lord, 1987) 6.217 at 25 °C (shake flask-GLC, de Bruijn et al., 1989) Solubility in water (ppb): 20 at 25 °C (extraction-GLC, Weil et al., 1974) 50 at 15 °C, 90 at 25 °C, 150 at 35 °C, 240 at 45 °C (particle size ≤5 µm, Biggar and Riggs, 1974) Vapor density: 17.2 ng/L at 30 °C (Spencer and Cliath, 1972) Vapor pressure (x 10-6 mmHg): 1.02 at 30 °C (Spencer and Cliath, 1972) 4.68 at 25 °C (estimated-GC, Bidleman, 1984) 8.25, 12.2 at 25 °C (subcooled liquid vapor pressure calculated from GC retention time data,
Hinckley et al., 1990) Environmental fate: Biological. It was reported that p,p′-DDD, a major biodegradation product of p,p′-DDT, was degraded by Aerobacter aerogenes under aerobic conditions yielding 1-chloro-2,2-bis(pchlorophenyl)ethylene, 1-chloro-2,2-bis(p-chlorophenyl)ethane, and 1,1-bis(p-chlorophenyl)ethylene. Under anaerobic conditions, however, four additional compounds were identified: bis(pchlorophenyl)acetic acid, p,p′-dichlorodiphenylmethane, p,p′-dichlorobenzhydrol, and p,p′- dichlorobenzophenone (Fries, 1972). Under reducing conditions, indigenous microbes in Lake Michigan sediments degraded DDD to 2,2-bis(p-chlorophenyl)ethane and 2,2-bis(pchlorophenyl)ethanol (Leland et al., 1973). Incubation of p,p′-DDD with hematin and ammonia gave 4,4′-dichlorobenzophenone, 1-chloro-2,2-bis(p-chlorophenyl)ethylene, and bis(p-chlorophenyl)acetic acid methyl ester (Quirke et al., 1979). Using settled domestic wastewater inoculum, p,p′-DDD (5 and 10 mg/L) did not degrade after 28 d of incubation at 25 °C (Tabak et al., 1981). Soil: In Hudson River, NY sediments, the presence of adsorbed p,p′-DDD in core samples suggests it is very persistent in this environment. The estimated half-life ranged from 4.2 to 4.5 yr (Bopp et al., 1982). Chemical/Physical. The hydrolysis rate constant for p,p′-DDD at pH 7 and 25 °C was determined to be 2.8 x 10-6/h, resulting in a half-life of 28.2 yr (Ellington et al., 1987). At 85 °C, the hydrolysis half-lives were 5.3 d, 43 min, and 130 min at pH values 7.22, 9.67, and 10.26, respectively (Ellington et al., 1987). 2,2-Bis(4-chlorophenyl)-1-chloroethene and HCl were reported as hydrolysis products (Kollig, 1993). Toxicity: EC50 (48-h) for Daphnia pulex 3.2 µg/L (Sanders and Cope, 1966), Simocephalus serrulatus 4.5 µg/L, Cypridopsis vidua 45 µg/L (Johnson and Finley, 1980), Daphnia magna 9.0 µg/L (Mayer and Ellersieck, 1986). EC50 (96-h) for Xenopus laevis 14.9 µM (Saka, 2004).
