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Triphenyl phosphate

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Triphenyl phosphate Basic information
Triphenyl phosphate Chemical Properties
  • Melting point:48-50 °C (lit.)
  • Boiling point:244 °C/10 mmHg (lit.)
  • Density 1.2055
  • vapor density 11.3 (vs air)
  • vapor pressure 1.3 mm Hg ( 200 °C)
  • refractive index 1.563
  • Flash point:435 °F
  • storage temp. Store below +30°C.
  • solubility H2O: soluble0.0019g/L at 20°C
  • form Crystalline Flakes
  • color White
  • OdorOdorless
  • Water Solubility insoluble
  • Merck 14,9742
  • BRN 1888236
  • Henry's Law Constant5.88 at 20 °C (approximate - calculated from water solubility and vapor pressure)
  • Exposure limitsTLV-TWA air 3 mg/m3 (ACGIH, OSHA, and NIOSH).
  • Stability:Stable.
  • InChIKeyXZZNDPSIHUTMOC-UHFFFAOYSA-N
  • CAS DataBase Reference115-86-6(CAS DataBase Reference)
  • NIST Chemistry ReferenceTriphenylphosphate(115-86-6)
  • EPA Substance Registry SystemTriphenyl phosphate (115-86-6)
Safety Information
MSDS
Triphenyl phosphate Usage And Synthesis
  • Chemical PropertiesTriphenyl phosphate (TPP) is a colorless crystalline powder with a faint, phenol-like odor. Triphenyl phosphate is practically insoluble in water at 1.9 × 10 7 mg/l at 24 °C (Yalkowsky et al., 2010). It is very soluble in carbon tetrachloride (Haynes, 2010) and is soluble in most lacquers, solvents, thinners, and oils, as well as in alcohol, benzene, ether, chloroform, and acetone (Lewis, 1996). It begins to decompose at about 600 °C in inert gas, and in a large excess of air, complete combustion to carbon dioxide occurs in the range 800–900 °C (Lhomme et al., 1984). Hydrolysis of TPP occurs very slowly in acidic or neutral solutions, but occurs rapidly in alkaline solutions (Barnard et al., 1966).
  • UsesTriphenyl Phosphate is used in the insecticidal composition. Also acts as a flame retardant.
  • UsesTriphenyl phosphate is prepared by reacting phosphorus pentoxide and phenol (Budavari, 2001), or by reacting phosphorus oxychloride and phenol (Snyder, 1990). One primary use is as a flame retardant in phenolic- and phenylene oxide-based resins for the manufacture of electrical and automobile components, for auto upholstery, and as a nonflammable plasticizer in cellulose acetate for photographic films. It has also been used to impregnate roofing paper. Triphenyl phosphate occurs as a plasticizer in various lacquers and varnishes (O’Neil, 2006), and as a component of lubricating oil and hydraulic fluids (ACGIH, 2012).
  • UsesTPP is used in fireproofing, in impregnating roofing paper, as a plasticizer in lacquers and varnishes, and as a substitute for camphor in celluloid materials to make the latter stable and fireproof..
  • Production MethodsPrepared by reacting phosphorus pentoxide and phenol and by reaction of triethyl phosphate and chloramine-T. On a larger scale phosphorus oxychloride and phenol are reacted in an esterification tank with heating. The HCL formed is trapped and condensed, while the crude triphenyl phosphate runs into a large tank where it is purified.
  • DefinitionChEBI: An aryl phosphate resulting from the formal condensation of phosphoric acid with 3 mol eq. of phenol.
  • Reactivity ProfileOrganophosphates, such as Triphenyl phosphate, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.
  • HazardToxic by inhalation. Cholinesterase inhibitor. Questionable carcinogen.
  • Health HazardNon-industrial:
    An allergic reaction in a 67-year old woman to spectacle frames containing triphenyl phosphate was reported. Patch tests with analytical grade triphenyl phosphate in that individual indicated a reaction at concentrations as low as 0.05%. This observation was confirmed in another male patient (Carlsen et al 1986). Industrial:
    Occupational exposure of men engaged in manufacturing triphenyl phosphate produced a statistically significant reduction in erythrocyte acetylcholinesterase activity and plasma cholinesterase activity. There was no evidence of adverse clinical effects in men exposed to triphenyl phosphate for as long as 10 years. Exposure was to triphenyl phosphate mist, vapor, and dust at a weighted average air concentration of 3.5 mg/m3 (Sutton et al 1960).
  • Health HazardTPP is neurotoxic, causing paralysis at high dosages. Like tri-o-cresyl phosphate (TOCP), it is a cholinesterase inhibitor. The acute oral toxicity is low. The acute toxicity via subcutaneous administration is low to moderate. The toxic symptoms from high dosages in test animals were tremor, diarrhea, muscle weakness, and paralysis.
    LD50 value, oral (mice): 1320 mg/kg
    LD50 value, subcutaneous (cats): 100 mg/kg
    Cleveland et al. (1986) investigated the acute and chronic toxicity to various species of freshwater fish of phosphate ester compounds containing TPP. The adverse toxic effects occurred at exposure concentrations of 0.38–1.0 mg/L..
  • Fire HazardNoncombustible solid. Incompatibility— none.
  • Industrial uses1 Plasticizer.
    2 Fireproofing agent, for impregnating roofing paper and upholstery.
  • Safety ProfilePoison by subcutaneous route. Moderately toxic by ingestion. Absorbed slowly, particularly by skin contact. Not a potent cholinesterase inhibitor. Combustible when exposed to heat or flame. To fight fire, use CO2, dry chemical. When heated to decomposition it emits toxic fumes of POx. See also TRITOLYL PHOSPHATE.
  • Potential ExposureTriphenyl phosphate is used to impregnate roofing paper and as a fire-resistant plasticizer in plastics; for cellulose esters in lacquers and varnishes. Used in making adhesives, gasoline additives; flotation agents; insecticides, surfactants, antioxidants, and stabilizers. A substitute for camphor.
  • SourceTriphenyl phosphate was identified as a component in outer covers of brand-new computer video display units. Concentrations were estimated to be 8 to 10 and 0.3 to 0.5 wt % in 4 and 6 video display units, respectively. The concentrations of triphenyl phosphate in the remaining 8 video display units were <0.02 wt % (Carlsson et al., 2000).
  • Environmental FateChemical/Physical. When an aqueous solution containing triphenyl phosphate (0.1 mg/L) and chlorine (3 to 1,000 mg/L) was stirred in the dark at 20 °C for 24 h, the benzene ring was substituted with one to three chlorine atoms (Ishikawa and Baba, 1988). The reported hydrolysis half-lives at pH values of 8.2 and 9.5 were 7.5 and 1.3 d, respectively (Howard and Doe, 1979).
    Decomposes at temperatures greater than 410 °C (Dobry and Keller, 1957)
  • MetabolismRat liver microsomal enzymes degraded triphenyl phosphate in the presence of NADPH, but also in the absence of NADPH. The product of incubation was diphenyl phosphate. It was clear that the reaction was cytochrome P-450-linked since the reaction was inhibited by carbon monoxide (Sasaki et al 1984). Goldfish liver microsomes metabolized only about 10% of triphenyl phosphate (Sasaki et al 1985). Houseflies treated with triphenyl phosphate were analyzed after 24 h and the presence of diphenyl p-hydroxyphenyl phosphate was confirmed (Eto et al 1975).
  • ShippingUN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
  • Purification MethodsCrystallise the phosphate from EtOH or pet ether (b 60-80o)/EtOH. [Cox & Westheimer J Am Chem Soc 80 5441 1958, Krishnakumar & Sharma Synthesis 558 1983, Cherbuliez in Organo Phosphorus Compounds (Kosolapoff & Maier eds) Wiley Vol 6 pp 211-577 1973, Beilstein 6 III 658, 6 IV 720.]
  • IncompatibilitiesIncompatible with strong oxidizers; strong acids; nitrates may cause fire or explosions. Phosphates are incompatible with antimony pentachloride, magnesium, silver nitrate, zinc acetate.
  • Waste DisposalIncinerate in furnace equipped with alkaline scrubber.
Triphenyl phosphate Preparation Products And Raw materials
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