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Benzyl butyl phthalate

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Benzyl butyl phthalate Basic information
Benzyl butyl phthalate Chemical Properties
  • Melting point:<-35°C
  • Boiling point:370°C
  • Density 1.1 g/mL at 25 °C(lit.)
  • vapor density 10.8 (vs air)
  • vapor pressure 0.16 mm Hg ( 150 °C)
  • refractive index n20/D 1.54(lit.)
  • Flash point:>230 °F
  • storage temp. Refrigerator
  • form Oily Liquid
  • color Clear
  • Specific Gravity1.1
  • Water Solubility 0.000269 g/100 mL
  • FreezingPoint -35℃
  • BRN 2062204
  • Henry's Law Constant(x 10-6 atm?m3/mol): 1.3 at 25 °C (calculated, Howard, 1989)
  • CAS DataBase Reference85-68-7(CAS DataBase Reference)
  • IARC3 (Vol. Sup 7, 73) 1999
  • NIST Chemistry ReferencePhthalic acid, benzyl butyl ester(85-68-7)
  • EPA Substance Registry SystemButyl benzyl phthalate (85-68-7)
Safety Information
  • Hazard Codes T,N
  • Risk Statements 61-50/53-62
  • Safety Statements 53-45-60-61
  • RIDADR UN 3082 9/PG 3
  • WGK Germany 2
  • RTECS TH9990000
  • Autoignition Temperature450 °F
  • TSCA Yes
  • HazardClass 9
  • PackingGroup III
  • HS Code 29173400
  • Hazardous Substances Data85-68-7(Hazardous Substances Data)
  • ToxicityAcute oral LD50 for guinea pigs 13,750 mg/kg, mice 4,170 mg/kg, rats 2,330 mg/kg (quoted, RTECS, 1985).
Benzyl butyl phthalate Usage And Synthesis
  • Chemical PropertiesBenzyl butyl phthalate is a clear, oily liquid with a slight odor.
  • UsesA phthalate metabolite with genotoxic effect.
  • Production MethodsBBP is manufactured by the sequential addition of butanol and benzyl chloride to phthalic anhydride. It is used as a plasticizer for polyvinyl chloride plastics, particularly vinyl floor tile, vinyl leather, and cloth coating.
  • General DescriptionA clear colorless liquid with a mild odor. Primary hazard is to the environment. Immediate steps should be taken to limit spread to the environment. Easily penetrates the soil to contaminate groundwater and nearby waterways.
  • Air & Water ReactionsSlightly soluble in water and slightly denser than water.
  • Reactivity ProfileBenzyl butyl phthalate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Can generate electrostatic charges. [Handling Chemicals Safely 1980. p. 250].
  • Health HazardProlonged contact with liquid causes some irritation of eyes and skin.
  • Health HazardThe acute oral toxicity of this compoundis low. It is, however, more toxic, thanthe phthalic acid dialkyl esters. The toxic symptomsinclude nausea, dizziness, somnolence, andhallucination. The oral LD50 value in mice iswithin the range of 4200 mg/kg. Oral admin istration produced reproductive toxicity inmale mice (paternal effects). At a dose of2% in diet, it caused maternal and develop mental toxicity and an increased incidence.
  • Fire HazardSpecial Hazards of Combustion Products: Irritating vapors of unburned chemical may form in fires.
  • Potential ExposureBenzyl butyl phthalate is used as a plasticizer for polyvinyl and cellulosic resins. It is also used as an organic intermediate. Incompatibilities: Incompatible with strong acids; nitrates, oxidizers. Destructive to rubber and paint.
  • CarcinogenicityThe NTP examined the carcinogenicity of BBP in rats and mice. Groups of 50 male and female rats and mice were exposed to BBP via the diet at levels of 0, 6000, or 12,000 ppm (0, 300, and 600 mg/kg for rats and 0, 780, or 1560 mg/kg for mice). Male and female mice and female rats were exposed for 103 weeks. Due to poor survival, all males were sacrificed at weeks 29–30; this part of the study was later repeated. No treatmentrelated neoplasms were observed in mice. Survival was not affected. A dose-dependent reduction in body weight in both sexes was the only treatment-related effect observed in this study. Furthermore, nonneoplastic changes were all within the normal limits of incidence for B6C3F1 mice. The NTP concluded that under the conditions of the bioassay, BBP “was not carcinogenic for B6C3F1 mice of either sex.” An increased incidence of mononuclear cell leukemias was observed in the high-dose female rats. No other treatmentrelated findings were observed. The NTP concluded that BBP was “probably carcinogenic for female F344/N rats, causing an increased incidence of mononuclear cell leukemias”. The biological significance of this finding is uncertain as the background incidence of this tumor type in F344 rats is quite high.
  • SourceDetected in distilled water-soluble fractions of new and used motor oil at concentrations of 8.6–13 and 14–17 μg/L, respectively (Chen et al., 1994)
  • Environmental FateBiological. In anaerobic sludge diluted to 10%, benzyl butyl phthalate biodegraded to monobutyl phthalate, which subsequently degraded to phthalic acid. After 40 d, >90% of applied amount degraded (Shelton et al., 1984). When benzyl butyl phthalate (5 and 10 mg/L) was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, complete biodegradation with rapid adaptation was observed after 7 d (Tabak et al., 1981). In activated sludge, the half-life was 2 h (Saeger and Tucker, 1976). Gledhill et al. (1980) reported half-lives of 2 and <4 d for benzyl butyl phthalate in river water and a lake water microcosm, respectively. Aerobic degradation of benzyl butyl phthalate by acclimated soil and activated sewage sludge microbes was studied using an acclimated shake flask CO2 evolution test. After 28 d, loss of benzyl butyl phthalate (primary degradation) was 43%, with a lag phase of 15.6 d, and ultimate biodegradation (CO2 evolution) was 43%. The half-life under these conditions was 19.4 d (Sugatt et al., 1984).
    Surface Water. The biological half-life of benzyl butyl phthalate in river water was determined to be 2 d (Saeger and Tucker, 1976).
    Photolytic. Gledhill et al. (1980) reported the photolytic half-life is >100 d.
    Chemical/Physical. Benzyl butyl phthalate initially hydrolyzes to butyl hydrogen phthalate. This compound undergoes additional hydrolysis yielding o-phthalic acid, 1-butanol, and benzyl alcohol (Kollig, 1993). Gledhill et al. (1980) reported the hydrolysis half-life is >100 d.
  • Solubility in organics4.05 (Veith et al., 1980)
    4.73 (Ellington and Floyd, 1996)
    4.80 (Hirzy et al., 1978)
    4.91 at 20 °C (shake flask-UV spectrophotometry, Leyder and Boulanger, 1983)
    4.77 (shake flask-GC, Gledhill et al., 1980)
  • ShippingUN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9—Miscellaneous hazardous material, Technical Name Required
  • Waste DisposalAtomize into an incinerator together with a flammable solvent.
Benzyl butyl phthalate Preparation Products And Raw materials
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