1-BUTANOL

H3C OH CASRN: 71-36-3; DOT: 1120; DOT label: Flammable liquid; molecular formula: C4H10O; FW: 74.12; RTECS: EO1400000; Merck Index: 12, 1575 Physical state, color, and odor: Clear, colorless liquid with a rancid sweet odor similar to fusel oil. Experimentally determined detection and recognition odor threshold concentrations were 900 µg/m3 (300 ppbv) and 3.0 mg/m3 (1.0 ppmv), respectively (Hellman and Small, 1974). Odor threshold concentration in water is 500 ppb (Buttery et al., 1988). The least detectable odor threshold in concentration water at 60 °C was 0.2 mg/L (Alexander et al., 1982). Cometto-Muñiz et al. (2000) reported nasal pungency threshold concentrations ranging from approximately 900 to 4,000 ppm. Melting point (°C): -88.72 (Huang et al., 2003) Boiling point (°C): 117.25 (Zhu et al., 2001) 117.69 (Artigas et al., 1997) Density (g/cm3): 0.81704 at 10.00 °C, 0.81476 at 13.00 °C, 0.81324 at 15.00 °C, 0.81095 at 18.00 °C, 0.80943 at

20.00 °C, 0.80715 at 23.00 °C (Troncoso et al., 2000) 0.8095 at 20.00 °C, 0.8057 at 25.00 °C (Shan and Asfour, 1999) 0.80203 at 30.00 °C (Sekar and Naidu, 1996) 0.81324 at 15.00 °C, 0.80548 at 20.00 °C, 0.79811 at 25.00 °C, 0.79020 at 30.00 °C (Martinez et

al., 2000a) 0.8024 at 30.00 °C, 0.7947 at 40.00 °C, 0.7852 at 50.00 °C (Weng, 2000) 0.79917 at 35.00 °C, 0.79049 at 40.00 °C (George et al., 2002) Diffusivity in water (x 10-6 cm2/sec): 11.8 at 35 °C, 13.4 at 40 °C, 14.7 at 45 °C (Li and Ong, 1990) 9.6 at 25 °C (Tominaga and Matsumoto, 1990; Hao and Leaist, 1996) Dissociation constant, pKa: 20.89 (quoted, Riddick et al., 1986) Flash point (°C): 35 (Acros Organics, 2002) Lower explosive limit (%): 1.4 (NIOSH, 1997) Upper explosive limit (%): 11.2 (NIOSH, 1997)

2.240 (quoted, Riddick et al., 1986) Henry’s law constant (x 10-6 atm⋅m3/mol): 7.90 at 25 °C (Snider and Dawson, 1985) 8.81 at 25 °C (Buttery et al., 1969; Amoore and Buttery, 1978) 8.33 at 25 °C (Butler et al., 1935) 7.14 at 25 °C (Burnett, 1963) 4.99 at 25 °C (headspace-GC, Gupta et al., 2000) 9.16 at 25 °C (batch stripping method-GC, Kim et al., 2000) 12.0 at 25 °C (headspace-GC, Gupta et al., 2000) 8.58 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) 1.86 at pH 7.1 and 30 °C (headspace-GC, Friant and Suffet, 1979) 7.21 at 30 °C (headspace-GC, Chaintreau et al., 1995) 20.3 at 37 °C (static headspace-GC, van Ruth et al., 2001) 9.39 at 25 °C (static headspace-GC, Merk and Riederer, 1997) 49.2 at 50 °C, 92.0 at 60 °C, 152 at 70 °C, 243 at 80 °C (headspace-GC, Hovorka et al., 2002) Interfacial tension with water (dyn/cm): 1.8 at 25 °C (Donahue and Bartell, 1952) 1.9 at 25 °C (Murphy et al., 1957) 1.86, 1.82, 1.79, 1.74, 1.71, and 1.63 at 20, 25, 30, 35, 40, and 50 °C, respectively (Saien and

Salimi, 2004) Ionization potential (eV): 10.04 (Franklin et al., 1969) Soil organic carbon/water partition coefficient, log Koc: 0.50 (Gerstl and Helling, 1987) Kd values: 0.94, 4.43, and 1.28 were reported for Dowex 1-X2 (Cl-), Dowex 1-X2 [bis(2-ethyl-

hexyl) phthalate ion], and Dowex 1-X8 (SO4-2) resins, respectively (Small and Bremer, 1964) Octanol/water partition coefficient, log Kow: 0.692 at 0 °C, 0.740 at 10 °C, 0.787 at 20 °C, 0.842 at 30 °C, 0.907 at 40 °C, 0.930 at 50 °C, 0.873

at 60 °C (shake flask-GC, Berg and Rankin, 2005) 0.785 at 25 °C (generator column-HPLC, Tewari et al., 1982; generator column-HPLC/GC, Wasik

et al., 1981) 0.80 at 25 °C (generator column-RPLC, Schantz and Martire, 1987) 0.81 at 20 °C (shake flask-GC, Gunning et al., 2000) 0.87 at 25 °C (shake flask-GLC, Riebesehl and E. Tomlinson, 1986) Solubility in organics (mole fraction): At 4.5 °C: 0.345 in triethylenetetramine, 0.321 in hexamethylenediamine (Copley et al., 1941) Solubility in water: 77,085 mg/L at 20 °C (Mackay and Yeun, 1983) 74,700 mg/L at 25 °C in Lake Superior water having a hardness and alkalinity of 45.5 and 42.2

mg/L as CaCO3, respectively (Veith et al., 1983) 74.5 g/L at 25 °C (Stockhardt and Hull, 1931) 63.3 g/L at 25.0 °C (generator column-HPLC, Tewari et al., 1982; generator column-HPLC/GC,

Wasik et al., 1981)

74 g/kg at 25 °C (De Santis et al., 1976) In wt %: 7.497 at 22.60 °C, 7.407 at 23.70 °C, 7.318 at 24.85 °C, 7.31 at 25.00 °C, 7.202 at 26.4

°C, 7.090 at 29.18 °C, 7.016 at 29.18 °C (interferometer, Butler et al., 1933) 6,700 mg/kg at 37.7 °C (shake flask-turbidimetric, McCants et al., 1953) 73 g/kg at 25 °C (Donahue and Bartell, 1952) 73 g/kg at 26.7 °C (Skrzec and Murphy, 1954) 70 g/kg at 25 °C (Petriris and Geankopolis, 1959) 91 mL/L at 25 °C (residue-volume method, Booth and Everson, 1948) 0.9919 M at 18 °C (shake flask-turbidimetric, Fühner, 1924) 0.961 at 25 °C (shake flask-GC, Li and Andren, 1994) In wt %: 10.33 at 0 °C, 8.98 at 9.6 °C, 8.03 at 20.0 °C, 7.07 at 30.8 °C, 6.77 at 40.1 °C, 6.54 at

50.0 °C, 6.35 at 60.1 °C, 6.73 at 70.2 °C, 7.04 at 80.1 °C, 7.26 at 90.6 °C (shake flask-GC, Stephenson and Stuart, 1986)

7.2 wt % at 37.8 °C (Jones and McCants, 1954) 74.1 g/kg at 25.0 °C (Hansen et al., 1949) In g/kg: 95.5 at 5.0 °C, 89.1 at 10.0 °C, 82.1 at 15.0 °C, 78.1 at 20.0 °C, 73.5 at 25.0 °C, 70.8 at

30.0 °C, 68.3 at 35.0 °C, 66.0 at 40.0 °C, 64.6 at 45.0 °C, 65.2 at 50.0 °C, 67.3 at 55.0 °C, 68.9 at 80.0 °C, 87.4 at 97.9 °C, 127.3 at 114.5 °C, 134.6 at 116.9 °C, 197.3 at 123.3 °C, 272.6 at 124.83 °C, 328.2 at 125.1 °C, 304.4 at 125.15 °C (Hill and Malisoff, 1926)

In g/kg: 127.2 at -18.01 °C, 97.9 at -3.11 °C, 60.3 at 40.0 °C, 60.3 at 65.0 °C, 64.7 at 81.0 °C, 97.9 at 107.72 °C, 127.2 at 117.4 °C, 151.5 at 120.30 °C, 175.1 at 122.45 °C (Jones, 1929)

65 g/kg at 26 °C, 61 g/kg at 50 °C (Othmer et al., 1942) In mole fraction: 0.0725 at 4.98 at 50 °C, 0.0642 at 11.79 °C, 0.0571 at 17.43 °C, 0.0522 at 22.00

°C, 0.0491 at 25.28 °C (Ochi et al., 1996). 65,723 mg/L at 25.0 °C (shake flask-GC, Li et al., 1992) Vapor density: 3.03 g/L at 25 °C, 2.56 (air = 1) Vapor pressure (mmHg): 21.5 at 42.2 °C (Dejoz et al., 1996a) 1.5 at 5.00 °C, 3.4 at 15.00 °C, 4.9 at 20.00 °C, 7.1 at 25.00 °C, 10.0 at 30.00 °C, 13.9 at 35.00 °C,

19.0 at 40.00 °C, 34.6 at 50.00 °C (Garriga et al., 1996) 5.5 at 22.6 °C, 10.3 at 30.9 °C, 14.8 at 36.2 °C, 19.6 at 40.7 °C, 31.0 at 48.2 °C (Kemme and

Kreps, 1969) 1.03 at 0.00 °C, 2.34 at 10.01 °C, 5.02 at 19.99 °C, 10.06 at 30.01 °C, 19.33 at 39.99 °C, 35.39 at

50.16 °C (static method, Munday et al., 1980) Environmental fate: Biological. 1-Butanol degraded rapidly, presumably by microbes, in New Mexico soils releasing carbon dioxide (Fairbanks et al., 1985). Bridié et al. (1979) reported BOD and COD values of 1.71 and 2.46 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. Heukelekian and Rand (1955) reported a similar 5-d BOD value of 1.66 g/g which is 64.0% of the ThOD value of 2.59 g/g. Using the BOD technique to measure biodegradation, the mean 5-d BOD value (mM BOD/mM 1-butanol) and ThOD were 3.64 and 60.7%, respectively (Vaishnav et al., 1987). In activated sludge inoculum, following a 20-d adaptation period, 98.8% COD removal was achieved. The average rate of biodegradation was 84.0 mg COD/g⋅h (Pitter, 1976). Photolytic. An aqueous solution containing chlorine and irradiated with UV light (λ = 350 nm) converted 1-butanol into numerous chlorinated compounds which were not identified (Oliver and

Reported rate constants for the reaction of 1-butanol and OH radicals in the atmosphere: 6.8 x 10-10 cm3/molecule⋅sec at 292 K (Campbell et al., 1976), 8.31 x 10-12 cm3/molecule⋅sec (Wallington and Kurylo, 1987). Reported rate constants for the reaction of 1-butanol and OH radicals in the atmosphere: 8.3 x 10-12 cm3/molecule⋅sec at 298 K (Atkinson, 1990); with OH radicals in aqueous solution: 2.2 x 10-9 L/molecule⋅sec (OH concentration 10-17 M) (Anbar and Neta, 1967). Based on an atmospheric OH concentration of 1.0 x 106 molecule/cm3, the reported half-life of 1-butanol is 0.96 d (Grosjean, 1997). Chemical/Physical. Complete combustion in air yields carbon dioxide and water vapor. Burns with a strongly luminous flame (Windholz et al., 1983). 1-Butanol 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 466 mg/L. The adsorbability of the carbon used was 107 mg/g carbon (Guisti et al., 1974). Exposure limits: NIOSH REL: ceiling 50 ppm (150 mg/m3), IDLH 1,400 ppm; OSHA PEL: TWA 100 ppm (300 mg/m3); ACGIH TLV: ceiling 50 ppm (adopted), ceiling 25 ppm (intended change for 1999). Symptoms of exposure: Inhalation may cause irritation to eyes, nose, and throat (coughing). Chronic exposure to high concentrations may cause photophobia, blurred vision, and lacrimation (Patnaik, 1992; Windholz et al., 1983). An irritation concentration of 75.00 mg/m3 in air was reported by Ruth (1986). Toxicity: EC50 (48-h) and EC50 (24-h) values for Spirostomum ambiguum were 875 and 823 mg/L, respectively (Nałecz-Jawecki and Sawicki, 1999). EC50 (15-min) for Vibrio fischeri 3.02 g/L at pH 7.3 (Gustavson et al., 1998). LC50 (96-h) for fathead minnows 1,730 mg/L (Veith et al., 1983). LC50 (48-h) and LC50 (24-h) values for Spirostomum ambiguum were 1,097 and 3,365 mg/L, respectively (Nałecz-Jawecki and Sawicki, 1999). LC0 (24-h) and LC100 (24-h) for creek chub in Detroit river water were 1,000 and 1,400 mg/L, respectively (Gillette et al., 1952). LC50 static bioassay values for fathead minnows in Lake Superior water maintained at 18-22 °C after 1, 24, 48, and 72 h were identical at a concentration of 1,950 mg/L and after 96 h, the LC50 was 1,910 mg/L (Mattson et al., 1976). Acute oral LD50 for wild birds 2,500 mg/kg, mice 5,200 mg/kg, rats 790 mg/kg, rabbits 384 mg/kg (quoted, RTECS, 1985). TLm (24-h) for brine shrimp 3,000 mg/L (Price et al., 1974). Source: 1-Butanol naturally occurs in white mulberries and papaya fruit (Duke, 1992). Identified as one of 140 volatile constituents in used soybean oils collected from a processing plant that fried various beef, chicken, and veal products (Takeoka et al., 1996). Uses: Preparation of butyl esters (e.g., butyl acetate, di-n-butyl phthalate), glycol ethers; solvent for waxes, resins, gums, and varnishes; hydraulic fluid; ingredient in perfumes and flavors; additive in deicing fluids; polishes, floor cleaners, stain removers, and in some gasolines (antiicing); diluent for brake fluids; humectant for cellulose nitrate.