2-NITROPHENOL

CASRN: 88-75-5; DOT: 1663; DOT label: Poison; molecular formula: C6H5NO3; FW: 139.11; RTECS: SM2100000; Merck Index: 12, 6717 Physical state, color, and odor: Pale yellow crystals with an aromatic odor Melting point (°C): 45-46 (Weast, 1986) Boiling point (°C): 216 (Weast, 1986) Density (g/cm3): 1.485 at 14 °C (Weast, 1986) 1.495 at 20 °C (Sax, 1984) 1.2942 at 40 °C, 1.2712 at 60 °C, 1.2482 at 80 °C (quoted, Standen, 1967) Diffusivity in water (x 10-5 cm2/sec): At ceff = 20 µM: 0.536 at 4.0 °C, 0.977 25.0 °C, 1.663 at 50.0 °C; 1.000 (ceff = 110 µM) at 25.0 °C

(Niesner and Heintz, 2000) Dissociation constant, pKa: 7.24 at 25 °C (quoted, Rosés et al., 2000) Flash point (°C): 73.5 (Sax, 1985) Lower explosive limit (%): Not pertinent (Weiss, 1986) Upper explosive limit (%): Not pertinent (Weiss, 1986) Entropy of fusion (cal/mol⋅K): 13.11 (Poeti et al., 1982) Heat of fusion (kcal/mol): 4.17 (Poeti et al., 1982) 4.20 (Tsonopoulos and Prausnitz, 1971) Henry’s law constant (x 10-6 atm⋅m3/mol): 2.70 at 5 °C, 4.37 at 10 °C, 5.92 at 15 °C, 6.33 at 20 °C, 12.5 at 25 °C, 16.7 at 30 °C (bubble

3.57 at 8 °C, 3.91 at 11.3 °C, 5.99 at 16.3 °C, 9.17 at 20.3 °C, 11.6 at 25 °C, 15.4 at 29 °C (column

stripping, Harrison et al., 2002) 0.74 at 5 °C (average derived from six field experiments, Lüttke and Levsen, 1997) At 20 °C: 11.1 at pH 8.1, 11.0 at pH 10.2, 8.9 at pH 11.9, 6.7 at pH 13.7 (wetted-wall column-UV,

Zhang et al., 2003) Ionization potential (eV): 9.29 (Mallard and Linstrom, 1998) Bioconcentration factor, log BCF: 1.48 (activated sludge), 1.48 (algae), 1.60 (golden ide) (Freitag et al., 1985) Soil organic carbon/water partition coefficient, log Koc: 1.79 (river sediment), 2.32 (coal wastewater sediment) (Kopinke et al., 1995) 2.06 (Brookstone clay loam, Boyd, 1982) 2.21 (coarse sand), 1.75 (loamy sand) (Kjeldsen et al., 1990) Kd = 35 mL/g on a Cs+-kaolinite (Haderlein and Schwarzenbach, 1993) 2.96 (glaciofluvial, sandy aquifer, Nielsen et al., 1996) 2.043, 1.758, 1.854, 1.708, 2.283 (various European soils, Gawlik et al., 2000) Octanol/water partition coefficient, log Kow: 1.62 at pH 7 (HPLC, Unger et al., 1978) 1.79 at 25 °C (shake flask-UV spectrophotometry, Fujita et al., 1964) 1.89 in buffer solution at pH 1.5 (Schwarzenbach et al., 1988) Solubility in organics: In g/kg at 25 °C: benzene (1,472; 3,597 at 30 °C) and ethanol (460) (Windholz et al., 1983) 0.33 and 1,270 mM at 25 °C in isooctane and butyl ether, respectively (Anderson et al., 1980) Solubility in water: 3.30 g/kg at 40 °C (Palit, 1947) 1.076, 1.697, and 2.935 g/L at 15.6, 24.8, and 34.7 °C, respectively (shake flask-conductimetry,

Achard et al., 1996) 1,060 mg/L at 20 °C, 2,500 mg/L at 25 °C (quoted, Howard, 1989) 1,300 mg/L at 25 °C (Riederer, 1990) 1,079 mg/L at 20 °C (buffer solution at pH 1.5, Schwarzenbach et al., 1988) 10, 8.34, 8.70, and 8.55 mM in doubly distilled water, Pacific seawater, artificial seawater, and

35% NaCl at 20 °C, respectively (modified shake flask-fluorometry, Hashimoto et al., 1984) In g/L: 0.895 at 10.00 °C, 1.35 at 20.00 °C, 2.00 at 30 °C (shake flask-UV spectrophotometry,

Beneš and Dohnal, 1999) In mmol/kg solution: 6.5 at 12.9 °C, 7.6 at 15.5 °C, 8.4 at 17.3 °C, 9.0 at 18.6 °C, 9.7 at 19.9 °C,

10.0 at 18.7 °C, 10.4 at 21.3 °C, 12.8 at 25.2 °C, 16.4 at 30.0 °C, 17.5 at 31.2 °C, 18.6 at 32.5 °C, 22.6 at 36.8 °C, 22.9 at 37.5 °C, 23.4 at 38.6 °C, 23.5 at 38.9 °C, 24.1 at 40.2 °C, 27.9 at 48.5 °C, 28.4 at 49.5 °C, 28.6 at 49.9 °C, 28.7 at 50.2 °C, and 30.7 at 54.2 °C (light transmission technique, Jaoui et al., 2002)

Vapor pressure (x 10-2 mmHg): 1.9 at 8 °C, 12 at 25 °C (quoted, Leuenberger et al., 1985a) 9.3 at 25 °C (gas saturation-HPLC/UV spectrophotometry, Sonnefeld et al., 1983) 8.9 at 25 °C (Riederer, 1990)

Biological. A microorganism, Pseudomonas putida, isolated from soil degraded 2-nitrophenol to nitrite. Degradation by enzymatic mechanisms produced nitrite and catechol. Catechol subsequently degraded to β-ketoadipic acid (Zeyer and Kearney, 1984). When 2-nitrophenol was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, 100% biodegradation with rapid adaptation was achieved after 7 d (Tabak et al., 1981). In a similar study, 2-nitrophenol degraded rapidly from flooded alluvial and pokkali (organic matter-rich acid sulfate) soils that were inoculated with parathion-enrichment culture containing 5day-old cultures of Flavobacterium sp. ATCC 27551 and Pseudomonas sp. ATCC 29353 (Sudhaker-Barik and Sethunathan, 1978a). 2-Nitrophenol disappeared completely with the formation of nitrite, particularly in the inoculated soils rather than in the uninoculated soils. In activated sludge inoculum, 97.0% COD removal was achieved. The average rate of biodegradation was 14.0 mg COD/g⋅h (Pitter, 1976). Groundwater. Nielsen et al. (1996) studied the degradation of 2-nitrophenol in a shallow, glaciofluvial, unconfined sandy aquifer in Jutland, Denmark. As part of the in situ microcosm study, a cylinder that was open at the bottom and screened at the top was installed through a cased borehole approximately 5 m below grade. Five liters of water was aerated with atmospheric air to ensure aerobic conditions were maintained. Groundwater was analyzed weekly for approximately 3 months to determine 2-nitrophenol concentrations with time. The experimentally determined first-order biodegradation rate constant and corresponding half-life were 0.05/d and 13.86 d, respectively. Photolytic. A second-order reaction rate constant of 9 x 10-13 cm3/molecule⋅sec was reported for the reaction of 2-nitrophenol and OH radicals in the atmosphere (Atkinson, 1985). Chemical/Physical. Oxidation by Fenton’s reagent (hydrogen peroxide and Fe3+) produced nitrohydroquinone and 3-nitrocatechol (Andersson et al., 1986). In an aqueous solution (initial pH 5.0), 2-nitrophenol (100 µM) reacted with Fenton’s reagent (35 µM). After 60-min and 4-h, about 50 and 90% of the 2-nitrophenol was destroyed, respectively. The pH of the solution decreased due to the formation of nitric acid (Lipczynska-Kochany, 1991). At influent concentrations (pH 3.0) of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities were 101, 56, 31, and 17 mg/g, respectively. The GAC adsorption capacities at pH 7.0 were 99, 46, 21, and 9.6 mg/g and at pH 9.0 they were 85, 35, 14, and 5.7 mg/g (Dobbs and Cohen, 1980). Toxicity: EC50 (15-min) for Photobacterium phosphoreum 41.1 mg/L (Yuan and Lang, 1997). IC50 (24-h) for river bacteria 43.0 mg/L (Yuan and Lang, 1997). LC50 (contact) for earthworm (Eisenia fetida) 5.9 µg/cm2 (Neuhauser et al., 1985). LC50 (48-h) for red killifish 275 mg/L (Yoshioka et al., 1986). Acute oral LD50 for mice 1,300 mg/kg, rats 334 mg/kg (quoted, RTECS, 1985). Uses: Indicator; preparation of o-nitroanisole and other organic compounds.