ACETONE

CASRN: 67-64-1; DOT: 1090; DOT label: Flammable liquid; molecular formula: C3H6O; FW: 58.08; RTECS: AL3150000; Merck Index: 12, 64 Physical state, color, odor, and taste: Clear, colorless, liquid with a sweet, fragrant odor. Sweetish taste. Odor threshold concentrations ranged from 42 ppmv (Nagata and Takeuchi, 1990) to 100 ppmv (Leonardos et al., 1969). Experimentally determined detection and recognition odor threshold concentrations were 48 mg/m3 (20 ppmv) and 78 mg/m3 (33 ppmv), respectively (Hellman and Small, 1974). Melting point (°C): -95.35 (Weast, 1986) Boiling point (°C): 56.11 (Kurihara et al., 2000; Nagata and Tamura, 1996) Density (g/cm3): 0.7897 at 20 °C (Qun-Fang et al., 1997) 0.7842 at 25.00 °C (Kurihara et al., 2000) 0.77876 at 30.00 °C (Lee and Chuang, 1997) 0.8032 at 10.00 °C, 0.7982 at 15.00 °C, 0.7754 at 35.00 °C, 0.7696 at 40.00 °C, 0.7625 at 45.00

°C, 0.7562 at 50.00 °C, 0.7493 at 55.00 °C, 0.7423 at 60.00 °C (Kahl et al., 2003) Diffusivity in water (x 10-5 cm2/sec): 0.754 at 10 °C and concentration of 5.3 g/L (elution method, Gustafson and Dickhut, 1994) 1.27 at 25 °C (Landy et al., 1997) At mole fraction concentration of 10-5: 1.17 at 20 °C (Gabler et al., 1996), 1.14 at 25 °C, 1.405 at

35 °C, 1.590 at 45 °C, 1.880 at 55 °C (Tyn and Calus, 1975) Flash point (°C): -18.9 (open cup, Eastman, 1995) Lower explosive limit (%): 2.5 (NIOSH, 1997) Upper explosive limit (%): 12.8 (NIOSH, 1997) Dissociation constant, pKa: ≈ 20 (Gordon and Ford, 1972) Heat of fusion (kcal/mol): 1.366 (Dean, 1987)

3.85 at 25 °C (Snider and Dawson, 1985) 4.13 at 24.0 °C (headspace-GC, Straver and de Loos, 2005) 3.30 at 25 °C (Butler and Ramchandani, 1935) 10.3 at 25 °C (static headspace-GC, Welke et al., 1998) 3.67 at 25 °C (Buttery et al., 1969) 3.70 at 25 °C (Hoff et al., 1993) 1.40 at 10 °C, 3.46 at 25 °C, 3.61 at 30 °C, 4.52 at 35 °C, 6.10 at 45 °C (bubble column-HPLC,

Zhou and Mopper, 1990) 1.03 at 5 °C, 1.44 at 10 °C, 1.96 at 15 °C, 2.58 at 20 °C, 3.51 at 25 °C (headspace-GC, Ji and

Evans, 2007) 1.87 at 25 °C (equilibrium static cell-GC, Chatkun Na Ayuttaya et al., 2001) 89.7 at 0 °C, 3.92 at 25 °C (headspace-GC, Arp and Schmidt, 2004) 3.57 at 25 °C (Burnett, 1963) 4.00 at 25 °C (Vitenberg et al., 1975) 3.70 at 25 °C (Benkelberg et al., 1995) 2.27 at 14.9 °C, 3.03 at 25 °C, 7.69 at 35.1 °C, 11.76 at 44.9 °C (Betterton, 1991) Ionization potential (eV): 9.68 (Gibson, 1977) 9.703 ± 0.006 (Lias, 1998) Soil organic carbon/water partition coefficient, log Koc: Although experimental methods for estimation of this parameter for ketones are lacking in the documented literature, an estimated value of -0.588 was reported by Ellington et al. (1993). Its miscibility in water and low Koc and Kow values suggest that acetone adsorption to soil will be nominal (Lyman et al., 1982). Octanol/water partition coefficient, log Kow: -0.24 at 20 °C (shake flask-chemical reaction, Collander, 1951) Solubility in organics: Soluble in ethanol, benzene, and chloroform (U.S. EPA, 1985). Miscible with dimethylformaldehyde, chloroform, ether, and most oils (Windholz et al., 1983). Solubility in water: Miscible (Palit, 1947). A saturated solution in equilibrium with its own vapor had a concentration of 440.6 g/L at 25 °C (Kamlet et al., 1987). Vapor density: 2.37 g/L at 25 °C, 2.01 (air = 1) Vapor pressure (mmHg): 180 at 20 °C (ACGIH, 1986; NIOSH, 1997) 235 at 25 °C (quoted, Howard, 1990) 284.37 at 30 °C, 424.10 at 40 °C, 615.05 at 50 °C (Van Ness and Kochar, 1967) 727.2 at 55.00 °C (Nagata and Tamura, 1996a) Environmental fate: Biological. Following a lag time of 20 to 25 h, acetone degraded in activated sludge (30 mg/L) at a rate constant ranging from 0.016 to 0.020/h (Urano and Kato, 1986). Soil bacteria can

COD values of 1.85 and 1.92 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. Similarly, Heukelekian and Rand (1955) reported a 5-d BOD value of 0.85 g/g which is 38.5% of the ThOD value of 2.52 g/g. Waggy et al. (1994) reported 5, 15, and 28-d BOD values of 14, 74, and 74%, respectively. Using the BOD technique to measure biodegradation, the mean 5-d BOD value (mM BOD/mM acetone) and ThOD were 1.52 and 38.0%, respectively (Vaishnav et al., 1987). Photolytic. Photolysis of acetone in air yields carbon monoxide and free radicals, but in isopropanol, pinacol is formed (Calvert and Pitts, 1966). Photolysis of acetone vapor with nitrogen dioxide via a mercury lamp gave peroxyacetyl nitrate as the major product with smaller quantities of methyl nitrate (Warneck and Zerbach, 1992). Reported rate constants for the reaction of acetone with OH radicals in the atmosphere and in water are 2.16 x 10-13 and 1.80 x 10-13 cm3/molecule⋅sec, respectively (Wallington and Kurylo, 1987; Wallington et al., 1988a). Between 20 and 100 mmHg, reaction of acetone with OH radicals revealed no significant pressure dependence. Reaction products likely to form include acetic acid, methanol, methyl-and peroxy radicals (Wollenhaupt et al., 2000). Cox et al. (1980) reported a rate constant of 5 x 10-13 cm3/molecule⋅sec for the reaction of gaseous acetone with OH radicals based on a value of 8 x 10-12 cm3/molecule⋅sec for the reaction of ethylene with OH radicals. Chemical/Physical. Hypochlorite ions, formed by the chlorination of water for disinfection purposes, may react with acetone to form chloroform. This reaction is expected to be significant within the pH range of 6 to 7 (Stevens et al., 1976). Acetone will not hydrolyze because it has no hydrolyzable functional group (Kollig, 1993). At an influent concentration of 1,000 mg/L, treatment with GAC resulted in an effluent concentration of 782 mg/L. The adsorbability of the GAC was 43 mg/g carbon (Guisti et al., 1974). Exposure limits: NIOSH REL: TWA 250 ppm (590 mg/m3), IDLH 2,500 ppm; OSHA PEL: TWA 1,000 ppm (2,400 mg/m3); ACGIH TLV: TWA 750 ppm (1,780 mg/m3), STEL 1,000 ppm. Symptoms of exposure: Inhalation of acetone at high concentrations may produce headache, mouth dryness, fatigue, nausea, dizziness, muscle weakness, speech impairment, and dermatitis. Ingestion causes headache, dizziness, and drowsiness (Patnaik, 1992). Prolonged contact with skin may produce erythema and dryness (Windholz et al., 1983). An irritation concentration of 474.67 mg/m3 in air was reported by Ruth (1986). Toxicity: EC50 (96-h) for rainbow trout 5.54 mg/L (Mayer and Ellersieck, 1986). EC50 (48-h) for Spirostomum ambiguum 9.7 g/L (Nałecz-Jawecki and Sawicki, 1999), Pseudokirchneriella subcapitata 5.639 g/L (Hsieh et al., 2006). EC50 (24-h) for rainbow trout 6.01 mg/L (Mayer and Ellersieck, 1986), Spirostomum ambiguum 9.35 g/L (Nałecz-Jawecki and Sawicki, 1999). LC50 (14-d) for Poecilia reticulata 6,368 mg/L (Könemann, 1981), 6,100 mg/L (Majewski et al., 1978). LC50 (12-d) for grass shrimp embryos (Palaemonetes pugio) 6.94 g/L (Rayburn and Fisher, 1997). LC50 (5-d) for Japanese quail (Coturnix coturnix japonica) and ring-neck pheasants (Phasianus colcichus) >40 g/kg (Hill et al., 1975). LC50 (4-d) for grass shrimp embryos (Palaemonetes pugio) 6.78 g/L (Rayburn and Fisher, 1997). LC50 (96-h) for Pimephales promelas 8,120 mg/L (Veith et al., 1983), and rainbow trout 5.54

LC50 (48-h) for Mexican axolotl 20.0 mg/L, clawed toad 24.0 mg/L (Sloof and Baerselman, 1980). LC50 (48-h) and LC50 (24-h) values for Spirostomum ambiguum were 22.1 and 26.2 g/L, respectively (Nałecz-Jawecki and Sawicki, 1999). LC50 (24-h) for rainbow trout 6.01 mL/L at pH 7.4 and 12 °C (Mayer and Ellersieck, 1986). LC50 (8-h inhalation) for rats 50,100 mg/m3 (Possani et al., 1959). LC100 (4-h) for protozoan (Paramecium caudatum) 2.9 volume % (Rajini et al., 1989). LC100 (10-min) for protozoan (Paramecium caudatum) 2.9 volume % (Rajini et al., 1989). Acute oral LD50 for rats 5,800 mg/kg, mice 3,000 mg/kg (quoted, RTECS, 1985). Kimura et al. (1971) reported acute oral LD50 values of 1.8, 4.5, 7.3, and 6.8 g/kg for newborn, immature, young adult, and old adult rats, respectively. TLm (24-h) for brine shrimp 2,100 mg/L (Price et al., 1974) Source: Naturally occurs in blood and urine in small concentrations. Reported in cigarette smoke (1,100 ppm) and gasoline exhaust (2.3 to 14.0 ppm) (quoted, Verschueren, 1983). Acetone occurs naturally in many plant species including cuneate Turkish savory (Satureja cuneifolia), catmint (Nepeta racemosa), Guveyoto (Origanum sipyleum), and Topukcayi shoots (Micromeria myrtifolia) at concentrations of 20, 2, 2, and 0.1, respectively (Baser et al., 1992, 1993; Ozek et al., 1992; Tumen, 1991). Acetone was also detected in Turkish calamint (Calamintha nepeta ssp. glandulosa) (Kirimer et al., 1992), pineapples, cauliflower leaves, tea leaves, West Indian lemongrass, jimsonweed, soybeans, carrots, bay leaves, hop flowers, apples, tomatoes, water mint leaves, alfalfa, pears, rice plants, white mulberries, clover-pepper, and roses (Duke, 1992). Acetone also was emitted from many forest plant species (Isidorov et al., 1985). Acetone was detected in diesel fuel at a concentration of 22,000 µg/g (Schauer et al., 1999). Identified as an oxidative degradation product in the headspace of a used engine oil (10-30W) after 4,080 miles (Levermore et al., 2001). Acetone also was detected in automobile exhaust at concentrations ranging from 0.09 to 4.50 mg/m3 (Grimaldi et al., 1996) and in cigarette smoke at concentrations ranging from 498 to 869 mg/m3 (Euler et al., 1996). Gas-phase tailpipe emission rates from California Phase II reformulated gasoline-powered automobiles with and without catalytic converters were 1.19 and 42 mg/km, respectively (Schauer et al., 2002). Vereecken and Peeters (2000) reported that acetone is formed from the reaction of α-pinene and OH radicals in the atmosphere. This reaction resulted in an acetone yield of 8.5% which is consistent with available experimental data. Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission rates of acetone were 749 mg/kg of pine burned, 462 mg/kg of oak burned, and 79 mg/kg of eucalyptus burned. Uses: Intermediate in the manufacture of many chemicals including acetic acid, chloroform, diacetone alcohol, methyl isobutyl ketone, methyl isobutyl carbinol, isophorone, methacrylic acid, methyl methacrylate, bisphenol-A; formulating solvent for automotive care solvents, paints, paint removers, resins, surface coatings, varnishes, and lacquers; spinning solvent for cellulose acetate; to clean and dry parts for precision equipment; solvent for potassium iodide, potassium permanganate, cellulose acetate, nitrocellulose, acetylene; delustrant for cellulose acetate fibers; specification testing for vulcanized rubber products; extraction of principals from animal and plant substances; ingredient in nail polish remover; manufacture of rayon, photographic films, explosives; sealants and adhesives; pharmaceutical manufacturing; production of lubricating oils; organic synthesis.