115-86-6 Usage
Chemical Description
Triphenyl phosphate is an ester of phosphoric acid with three phenyl groups attached to the phosphate group.
Uses
Used in Electrical and Automobile Industries:
Triphenyl phosphate is used as a flame retardant in phenolicand phenylene oxide-based resins for the manufacture of electrical and automobile components. It provides nonflammable properties to these components, enhancing their safety and performance.
Used in Textile Industry:
Triphenyl phosphate is used as a flame retardant for auto upholstery, ensuring the safety and fire resistance of vehicle interiors.
Used in Plastics Industry:
Triphenyl phosphate is used as a nonflammable plasticizer in cellulose acetate for photographic films, improving the flexibility and workability of the material while maintaining its fire-resistant properties.
Used in Construction Industry:
Triphenyl phosphate has been used to impregnate roofing paper, providing additional fire protection to the roofing material.
Used in Coatings and Adhesives:
Triphenyl phosphate is used as a plasticizer in various lacquers and varnishes, enhancing their flexibility and workability.
Used in Lubricants and Hydraulic Fluids:
Triphenyl phosphate is used as a component of lubricating oil and hydraulic fluids, improving their performance and reducing wear.
Used in Insecticidal Compositions:
Triphenyl phosphate is used in the insecticidal composition, providing additional benefits to the formulation.
Used in Hydraulic Liquids, Adhesives, Inks, and Coatings:
Triphenyl phosphate is used as a plasticizer in these applications, improving the flexibility and workability of the materials.
Used as a Substitute for Camphor in Celluloid Materials:
Triphenyl phosphate is used as a substitute for camphor in celluloid materials to make them stable and fireproof, enhancing their safety and performance.
Preparation
Triphenyl phosphate is prepared by reacting phosphorus pentoxide and phenol (Budavari, 2001), or by reacting phosphorus oxychloride and phenol (Snyder, 1990). 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.
Reactivity Profile
Organophosphates, 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.
Hazard
Toxic by inhalation. Cholinesterase
inhibitor. Questionable carcinogen.
Health effects
Non-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).
Fire Hazard
Noncombustible solid. Incompatibility— none.
Safety Profile
Poison 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 Exposure
Triphenyl 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.
Source
Triphenyl 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 fate
Chemical/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)
Metabolism
Rat 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).
Shipping
UN3077 Environmentally hazardous substances,
solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous
material, Technical Name Required.
Purification Methods
Crystallise 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.]
Toxicity evaluation
Triphenyl phosphate(TPP) 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/kgLD50 value, subcutaneous (cats): 100 mg/kgCleveland 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.
Incompatibilities
Incompatible with strong oxidizers;
strong acids; nitrates may cause fire or explosions.
Phosphates are incompatible with antimony pentachloride,
magnesium, silver nitrate, zinc acetate.
Waste Disposal
Incinerate in furnace
equipped with alkaline scrubber.
Check Digit Verification of cas no
The CAS Registry Mumber 115-86-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 5 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 115-86:
(5*1)+(4*1)+(3*5)+(2*8)+(1*6)=46
46 % 10 = 6
So 115-86-6 is a valid CAS Registry Number.
InChI:InChI=1/C18H15O4P/c19-23(20-16-10-4-1-5-11-16,21-17-12-6-2-7-13-17)22-18-14-8-3-9-15-18/h1-15H
115-86-6Relevant articles and documents
Stereospecific Deoxygenation of Aliphatic Epoxides to Alkenes under Rhenium Catalysis
Nakagiri, Takuya,Murai, Masahito,Takai, Kazuhiko
, p. 3346 - 3349 (2015)
The combination of a catalytic amount of Re2O7 and triphenyl phosphite as a reductant is effective for the deoxygenation of unactivated aliphatic epoxides to alkenes. The reaction proceeds stereospecifically with variously substituted epoxides under neutral conditions and is compatible with various functional groups. Protection and deprotection of a double bond functionality using an epoxide are shown as an example of the current rhenium-catalyzed deoxygenation protocol. The effect of reductants for the stereoselectivity has also been studied, indicating that the use of electron-deficient phosphines or phosphites is the key for the stereospecific deoxygenation. (Chemical Equation Presented).
CHEMILUMINESCENCE UPON DECOMPOSITION OF THE OZONIDE OF TRIPHENYLPHOSPHITE
Shereshovets, V. V.,Ostakhov, S. S.,Korotaeva, N. M.,Sharipov, G.L.,Kazakov, V. P.,et al.
, p. 2460 - 2462 (1989)
We have studied the spectral composition of luminescence and the kinetics of attenuation of chemiluminescence upon thermal decomposition of the ozonide of triphenylphosphite.We have established that the emitter of chemiluminescence in the IR region is singlet oxygen, and the emitter of chemiluminescence in the visible region is triphenylphosphate.
PROPERTIES OF TRIPHENYLPHOSPHITE-MODIFIED RHODIUM CARBONYL CATALYSTS FOR THE HYDROFORMYLATION OF 2-BUTENES
Slivinskii, E. V.,Markova, N. A.,Teleshev, A. T.,Korneeva, G. A.,Butkova, O. L.,et al.
, p. 2457 - 2461 (1990)
The factor responsible for the deactivation of a carbonyl triphenylphosphite rhodium hydroformylation catalyst appears to be the formation of a chelate-structure complex with diphenylphosphite, which is the product of partial hydrolysis of the organophosphorus ligand.The deactivating effect of diphenylphosphite can be supressed upon interaction of the H(O)P(OPh)2 and P(OPh)3-modified complex with 2-butenes under hydroformylation reaction conditions.
Aerobic Oxidation of Phosphite Esters to Phosphate Esters by Using an Ionic-Liquid-Supported Organotelluride Reusable Catalyst
Mihoya, Aya,Shibuya, Yuga,Ito, Akane,Toyoda, Anna,Oba, Makoto,Koguchi, Shinichi
, p. 2043 - 2045 (2020)
We describe the synthesis of an ionic-liquid (IL)-supported organotelluride catalyst and its application as a recyclable catalyst for the aerobic oxidation of phosphite esters to phosphate esters. This method shows high conversion rates, allows the ready isolation and purification of the resulting products, and exhibits good reusability of the catalyst.
VOLTAMMETRIC STUDY OF REACTIONS OF TRIPHENYLPHOSPHITE OZONIDE
Rusakov, I. A.,Shereshovets, V. V.,Abramova, N. A.,Maistrenko, V. N.,Murinov, Yu. I.
, p. 65 - 67 (1992)
The electrochemical characteristics of reduction of triphenylphosphite ozonide at a stationary platinum electrode were determined in acetonitrile at between -30 and -11 deg C.The feasibility of employing voltammetric methods to investigate the reactions of phosphite ozonides was demonstrated in a model study of the kinetics of the thermal decomposition of (C6H5O)3PO3 and its reaction with triphenylphosphite. Keywords: kinetics, decomposition, ozonide, triphenylphosphite, ozonation, voltammetry.
Tellurium tetrachloride as an efficient chlorinating agent for di- or trialkyl phosphites: Novel synthesis of dialkyl chlorophosphates
Koh,Oh
, p. 1771 - 1774 (1993)
Various dialkyl chlorophosphates are prepared by the reaction of TeCl4 with di- or trialkyl phosphites in good yields.
Iodosobenzene and iodoxybenzene as reagents for oxygen transfer in organophosphorus chemistry
Mielniczak,Lopusiński
, p. 505 - 508 (2001)
The application of iodosobenzene (1) and iodoxybenzene (2) for the oxidation reaction of phosphorous, phosphorothiono and phosphoroseleno compounds into the corresponding ≡P(O) analogs is demonstrated. Retention of configuration at the phosphorus atom and full stereoselectivity of these reactions in model diastereoisomeric cis- and trans-2-phenylamino-2-thiono-4-methyl-1.3.2-dioxaphosphorinans (30) as well cis- and trans-2-phenylamino-2-seleno-4-methyl-1.3.2-dioxaphosphorinans (31) systems, are demonstrated.
A Reexamination of the Ozone-Triphenyl Phosphite System. The Origin of Triphenyl Phosphate at Low Temperatures
David Mendenhall,Priddy, Duane B.
, p. 5783 - 5786 (1999)
The reaction of ozone with triphenyl phosphite (P) at -78°C affords a labile 1:1 complex (PO3) together with small amounts of triphenyl phosphate (PO) (Q. E. Thompson, J. Am. Chem. Soc. 1961, 83, 845). In this work we found that the amount of PO present initially after complete ozonation of P in toluene was 12 ± 2% at -78°C and 11 ± 2% at -95°C. Partial ozonation of solutions of P in toluene at -78°C gave mixtures of P, PO, and PO3 whose composition changed with time as a result of the reaction of P with PO3 to give additional PO. Between -25 and -60 °C, the rate constant of the latter reaction is given by the expression log k (M-1 s-1) = (8.64 ± 0.04) - (11.44 ± 0.74) kcal/AT. This reaction at -78°C is too slow to account for the PO formed during the ozonation, which is proposed to arise instead by competitive reactions of an intermediate. The solubility of PO in toluene at -78°C was measured as 0.06 M, and that of PO3 about 6 times greater.
Preparation of Flame-Resistant Liquids Based on Mixed Tri(phenyl, p-tert-butylphenyl) Phosphates by Transesterification of Triphenyl Phosphate with p-tert-Butylphenol
Karchevskaya, O. G.,Korneeva, G. A.,Kron, T. E.,Noskov, Yu. G.
, p. 1237 - 1243 (2020)
Abstract: The possibility of controlling the composition of a mixture of triphenyl phosphate, p-tert-butylphenyl diphenyl phosphate, di(p-tert-butylphenyl)phenyl phosphate, and tri(p-tert-butylphenyl) phosphate, formed by transesterification of triphenyl phosphate with p-tert-butylphenol, was demonstrated. The amount of p-tert-butylphenol necessary for transesterification of triphenyl phosphate to yield a mixture of phosphates of required composition was determined. If necessary, the composition of the phosphates can be adjusted by selective distillation of triphenyl phosphate in a vacuum.
Zero-Valent Amino-Olefin Cobalt Complexes as Catalysts for Oxygen Atom Transfer Reactions from Nitrous Oxide
Gianetti, Thomas L.,Rodríguez-Lugo, Rafael E.,Harmer, Jeffrey R.,Trincado, Monica,Vogt, Matthias,Santiso-Quinones, Gustavo,Grützmacher, Hansj?rg
, p. 15323 - 15328 (2016)
The synthesis and characterization of several zero-valent cobalt complexes with a bis(olefin)-amino ligand is presented. Some of these complexes proved to be efficient catalysts for the selective oxidation of secondary and allylic phosphanes, as well as diphosphanes, even with a direct P?P bond. With 5 mol % catalyst loadings the oxidations proceed under mild conditions (25–70 °C, 7–22 h, 2 bar N2O) and afford good to excellent yields (65–98 %). In this process, the greenhouse gas N2O is catalytically converted into benign N2and added-value organophosphorus compounds, some of which are difficult to obtain otherwise.
