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Tributyl phosphate

Basic information Chemical Properties Uses Potential Exposure Safety Related Supplier
Tributyl phosphate Basic information
Tributyl phosphate Chemical Properties
  • Melting point:-79 °C
  • Boiling point:289 °C
  • Density 0.979 g/mL at 25 °C(lit.)
  • vapor density 9.2 (vs air)
  • vapor pressure 27 mm Hg ( 178 °C)
  • refractive index n20/D 1.424(lit.)
  • Flash point:380 °F
  • storage temp. Store below +30°C.
  • solubility water: soluble1ml in 165ml water
  • form Liquid
  • color Clear
  • OdorOdorless
  • Water Solubility 0.6 g/100 mL
  • Merck 14,9618
  • BRN 1710584
  • Exposure limitsTLV-TWA 2.18 mg/m3 (0.2 ppm) (ACGIH), 5 mg/m3 (OSHA and NIOSH); IDLH 1300 mg/m3 (120 ppm) (NIOSH).
  • Stability:Stable. Combustible. Incompatible with strong oxidizing agents. May be water sensitive.
  • CAS DataBase Reference126-73-8(CAS DataBase Reference)
  • NIST Chemistry ReferenceTri-n-butylphosphate(126-73-8)
  • EPA Substance Registry SystemTributyl phosphate (126-73-8)
Safety Information
  • Language:EnglishProvider:TBP
  • Language:EnglishProvider:ACROS
  • Language:EnglishProvider:SigmaAldrich
  • Language:EnglishProvider:ALFA
Tributyl phosphate Usage And Synthesis
  • Chemical PropertiesTributyl phosphate is an odorless colorless to yellow liquid. The solubility of TBP is only 280 mg/L in water at 25°C. It is soluble in diethyl ether, benzene, carbon disulfide. It can be miscible with ethanol. It is stable, but it is incompatible with strong oxidizing agents.
  • UsesTBP is a trialkyl phosphate that is the tributyl ester of phosphoric acid. TBP is a toxic organophosphorous compound widely used in many industrial applications, including significant usage in nuclear processing. TBP is a solvent and plasticizer for cellulose esters such as nitrocellulose and cellulose acetate. The major uses of TBP in industry are as a component of aircraft hydraulic fluid and as a solvent for extraction and purification of rare earth metals from their ores, such as uranium and plutonium. TBP is used also in mercerizing liquids, where it improves their wetting properties. TBP is also used as a heat exchange medium. TBP is used in some consumer products such as herbicides and water thinned paints and tinting bases.
  • Potential ExposureThe industrial application of this chemical is responsible for occupational exposure and environmental pollution. Exposure to TBP can be from ingestion, inhalation, or skin or eye contact. This exposure will most often happen from occupational use of hydraulic fluid. If TBP is released to the environment, it will bind tightly to dust particles in the air. Unbound TBP will break down in air. It will move slowly through soil because it will bind with soil particles. It may volatilize slowly from moist soil and water surfaces. It may build up in aquatic organisms. It will be broken down in water by microbes.
  • DescriptionOn decomposition, TBP releases COx, toxic fumes of phosphoric acid, phosphorus oxides, and/or phosphine. TBP is incompatible with strong oxidising agents and alkalis. The major uses of TBP in industry are as a component of aircraft hydraulic fluid and as a solvent for rare earth extraction and purification. Minor uses of TBP include use as a defoamer additive in cement casings for oil wells, an anti-air entrainment additive for coatings and floor finishes, as well as a carrier for fluorescent dyes. The major uses of TBP comprise over 80% of the volume produced.
  • Chemical PropertiesStable, colorless liquid; odorless. Miscible with most solvents and diluents; soluble in water. Combustible.
  • Physical propertiesClear, colorless to pale yellow, odorless, slightly flammable, oily liquid
  • UsesTributyl phosphate is used as a plasticizer for cellulose esters, vinyl resins, and lacquers; and in making fireretardants, biocides, defoamers, and catalysts.
  • UsesExtractant for metal complexes.1
  • UsesPlasticizer for cellulose esters, lacquers, plastics, and vinyl resins.
  • DefinitionChEBI: A trialkyl phosphate that is the tributyl ester of phosphoric acid.
  • Production MethodsPrepared by the reaction of phosphorus oxychloride with butyl alcohol.
  • Air & Water ReactionsWater insoluble. Reacts slowly with water under basic conditions.
  • Reactivity ProfileTributyl phosphate is incompatible with strong oxidizing agents and strong bases. Attacks some forms of plastics and rubber .
  • Health HazardToxic by ingestion and inhalation, irritant to skin, bladder, eye and upper respiratory tract. May cause stimulation of the central nervous system.
  • Health HazardAcute
    There are no data on the toxicity of TBP to man. The TLV is established by the American Council of Governmental Industrial Hygienists on the basis of analogy with triphenyl phosphate with which it bears some similarities in its toxic properties (ACGIH 1986).
    A personal communication to ACGIH notes that workers exposed to 15 mg/m3 of TBP have complained of nausea and headache (ACGIH 1986). There are no other documented reports of deleterious effects of TBP in industrial situations.
    Inhibition of human erythrocyte and plasma cholinesterase is reported to be weak, even in vitro (Hayes and Sabine 1952; Sandmeyer and Kirwin 1981).
  • Health HazardTributyl phosphate is a neurotoxic compound and an irritant. The toxic effects are characteristic of organic phosphates. It inhibits cholinesterase activity and causes paralysis. Inaddition,itcancausedepressionofthecentralnervoussystem,aswellasirritationofthe skin,eyes,andrespiratorypassage.Inhalation toxicity data in the literature are inconsistent.
    The oral toxicity in rats was low; the LD50 value was reported as 1189 mg/kg (NIOSH 1986).
    The pure liquid instilled into rabbits’ eyes caused severe irritation but no permanent damage. The irritation effect on the skin is mild.
    Tributyl phosphate exhibited teratogenic effects in rats. There is no report on its carcinogenicity..
  • Fire HazardSpecial Hazards of Combustion Products: Toxic fumes of PO x
  • Industrial uses1. As an antifoaming agent.
    2. As a plasticizer for cellulose esters, lacquers, plastics, and vinyl resins.
    3. As a complexing agent in the extraction of heavy metals, especially for the extraction of metal ions from solutions of reactor products in nuclear fuel reprocessing.
    4. As an aircraft hydraulic fluid.
    5. As a heat exchange medium and dielectric.
    6. As a pigment-grinding agent.
  • Safety ProfilePoison by intraperitoneal and intravenous routes. Moderately toxic by ingestion, inhalation, and subcutaneous routes. Experimental reproductive effects. A skin, eye, and mucous membrane irritant. Combustible when exposed to heat or flame. To fight fire, use CO2, dry chemical, fog, mist. When heated to decomposition it emits toxic fumes of POx.
  • Environmental FateBiological. Indigenous microbes in Mississippi River water degraded tributyl phosphate to carbon dioxide. After 4 wk, 90.8% of the theoretical carbon dioxide had evolved (Saeger et al., 1979).
    Chemical/Physical. Complete hydrolysis yields 1-butanol and phosphoric acid via the intermediates dibutyl phosphate and monobutyl phosphate (Thomas and Macaskie, 1996).
  • MetabolismA system was developed utilizing isolated anterior forearm stratum corneum conjunctum of man to study skin penetrating capacity of a series of organic phosphates. TBP was tested in the system and was among the least penetrating of the compounds tested, only phosphoric acid and tri-o-cresyl phosphate penetrating less well. The value given was μmoles/cm2/min as the average maximum steady-state rate of penetration. In a comparative study with 3 living subjects, penetration was essentially the same as in the isolated skin preparation (Marzulli et al 1965).
    Rats given a single oral dose of [14C]-labeled TBP at 14 mg/kg excreted 50, 10, and 6% of the administered dose in the urine, exhaled air, and feces, respectively, within 24 h. A single intraperitoneal dose at the same rate resulted in 70,7, and 4% of the administered dose in the urine, exhaled air, and feces within the first 24 h (Suzuki et al 1984).
    Single oral administration of TBP to rats at 156 mg/kg led to its appearance in all the tissues in the first 30 min. The major amount was in the gastrointestinal tract where it was poorly absorbed and was rapidly eliminated. The total level of TBP in all other organs and tissues was 5.73%, but none was detected after 3 d (Khalturin and Andryushkeeva 1986).
    A single i.p. dose of TBP at 250 mg/kg to rats resulted in 11 phosphoruscontaining metabolites in the urine within 24 h. The principal metabolic pathway resulted in stepwise debutylation, through hydroxylated intermediates, to give dibutyl hydrogen phosphate and butyl dihydrogen phosphate. Butyl bis(3-hydroxybutyl) phosphate and small amounts of monohydroxylated butyl derivatives also were isolated. Several metabolites, presumably resulting from omegaoxidation of the ?-butyl moieties to give butyric acid derivatives, also were detected, the result of a secondary pathway. In addition, butyl 2-hydroxybutyl hydrogen phosphate was isolated and characterized. The administration of a possible intermediate, dibutyl 3-oxobutyl phosphate, gave a metabolic profile similar to that of dibutyl 3-hydroxybutyl phosphate, the major metabolite, thus supporting the view that this compound was on the major metabolic pathway. Separate direct administration of various hydroxylated metabolites supported the metabolic pathways proposed (Suzuki et al 1984).
    Rat liver microsomal preparations also metabolized TBP to mono- and dihydroxylated intermediates, giving dibutyl hydrogen phosphate as the terminal metabolite (Sasaki et al 1984). Microsomal preparations from goldfish liver and killifish also resulted in dibutyl 3-hydroxybutyl phosphate and dibutyl hydrogen phosphate (Sasaki et al 1985).
  • Purification MethodsThe main contaminants in commercial samples are organic pyrophosphates, monoand dibutyl phosphates and butanol. It is purified by washing successively with 0.2M HNO3 (three times), 0.2M NaOH (three times) and water (three times), then fractionally distilled under vacuum. [Yoshida J Inorg Nucl Chem 24 1257 1962.] It has also been purified via its uranyl nitrate addition compound, obtained by saturating the crude phosphate with uranyl nitrate. This compound is crystallised three times from n-hexane by cooling to -40o, and then decomposed by washing with Na2CO3 and water. Hexane is removed by steam distillation; the water is then evaporated under reduced pressure, and the residue is distilled under reduced pressure. [Siddall & Dukes J Am Chem Soc 81 790 1959.] Alternatively, wash it with water, then with 1% NaOH or 5% Na2CO3 for several hours, then finally with water. Dry it under reduced pressure and fractionate it carefully under vacuum. It is a stable colourless oil, sparingly soluble in H2O (1mL dissolves in 165mL of H2O), but freely miscible in organic solvents. [Kuivila & Masterton J Am Chem Soc 74 4953 1952, Cox & Westheimer J Am Chem Soc 80 5441 1958, 31P NMR: Van Wazer J Am Chem Soc 78 5715 1956, Fertig et al. J Chem Soc 1488 1957, Beilstein 1 IV 1531.]
  • Waste DisposalTributyl phosphate is dissolved in a combustible solvent and is burned in a chemical incinerator equipped with an afterburner and scrubber.
Tributyl phosphate Preparation Products And Raw materials
Tributyl phosphate(126-73-8)Related Product Information
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