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Triphenyl phosphate

CAS No.
115-86-6
Chemical Name:
Triphenyl phosphate
Synonyms
TPP;TPPA;TRIPHENYL PHOSPHATE (TPP);PHOSPHORIC ACID TRIPHENYL ESTER;Phosflex TPP;Altal;Dymel;Wako TPP;NSC 57868;Plastifier
CBNumber:
CB9233809
Molecular Formula:
C18H15O4P
Molecular Weight:
326.28
MOL File:
115-86-6.mol

Triphenyl phosphate 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
Odor Odorless
Water Solubility insoluble
Merck 14,9742
BRN 1888236
Henry's Law Constant 5.88 at 20 °C (approximate - calculated from water solubility and vapor pressure)
Exposure limits TLV-TWA air 3 mg/m3 (ACGIH, OSHA, and NIOSH).
Stability Stable.
InChIKey XZZNDPSIHUTMOC-UHFFFAOYSA-N
Indirect Additives used in Food Contact Substances TRIPHENYL PHOSPHATE
FDA 21 CFR 175.105
CAS DataBase Reference 115-86-6(CAS DataBase Reference)
EWG's Food Scores 5
FDA UNII YZE19Z66EA
NIST Chemistry Reference Triphenylphosphate(115-86-6)
EPA Substance Registry System Triphenyl phosphate (115-86-6)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS09
Signal word  Warning
Hazard statements  H410-H400
Precautionary statements  P273-P501
Hazard Codes  Xn,N,F,Xi
Risk Statements  22-38-40-48/20/22-50/53-52/53-36/37/38-67-66-36-11-51/53
Safety Statements  36/37-61-60-24/25-22-36-26-16-24-9
RIDADR  UN 3077 9/PG 3
WGK Germany  2
RTECS  TC8400000
Autoignition Temperature >500 °C
TSCA  Yes
HazardClass  9
PackingGroup  III
HS Code  29190010
Toxicity LD50 orally in Rabbit: 3500 mg/kg LD50 dermal Rabbit > 7900 mg/kg
IDLA 1,000 mg/m3
NFPA 704
1
1 0

Triphenyl phosphate price More Price(26)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.21197 Triphenyl phosphate for synthesis 115-86-6 100g $35.1 2022-05-15 Buy
Sigma-Aldrich 8.21197 Triphenyl phosphate for synthesis 115-86-6 1kg $67.8 2022-05-15 Buy
Sigma-Aldrich 759511 Triphenyl phosphate solution NMR reference standard, 0.03357?M in chloroform-d (99.8 atom % D), NMR tube size 5?mm × 8?in. 115-86-6 1pkg $231 2022-05-15 Buy
Sigma-Aldrich 756911 Triphenyl phosphate solution NMR reference standard, 3?mM in chloroform-d (99.8 atom % D), NMR tube size 5?mm × 8?in. 115-86-6 1pkg $77.5 2022-05-15 Buy
Sigma-Aldrich 736368 Triphenyl phosphate solution NMR reference standard, 0.0485?M in acetone-d6 (99.9 atom % D), NMR tube size 5?mm × 8?in. 115-86-6 1pkg $342 2022-05-15 Buy
Product number Packaging Price Buy
8.21197 100g $35.1 Buy
8.21197 1kg $67.8 Buy
759511 1pkg $231 Buy
756911 1pkg $77.5 Buy
736368 1pkg $342 Buy

Triphenyl phosphate Chemical Properties,Uses,Production

Chemical Properties

Triphenyl 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).

Uses

Triphenyl Phosphate is used in the insecticidal composition. Also acts as a flame retardant.

Uses

Triphenyl 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).

Uses

TPP 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 Methods

Prepared 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.

Definition

ChEBI: An aryl phosphate resulting from the formal condensation of phosphoric acid with 3 mol eq. of phenol.

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 Hazard

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).

Health Hazard

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/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 Hazard

Noncombustible solid. Incompatibility— none.

Industrial uses

1 Plasticizer.
2 Fireproofing agent, for impregnating roofing paper and upholstery.

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.]

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.

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View Lastest Price from Triphenyl phosphate manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2022-02-25 TPP
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2022-01-14 Phenyl phosphate
115-86-6
US $30.00 / ASSAYS 1ASSAYS 99% 100ton Shanghai Yunao International Trade Co., Ltd
2021-12-01 Triphenyl Phosphate (TPP)
115-86-6
US $9.60 / KG 1KG 99% 5000kg Hebei Crovell Biotech Co Ltd
  • TPP
  • US $0.00 / KG
  • 98%+
  • WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
  • Phenyl phosphate
    115-86-6
  • US $30.00 / ASSAYS
  • 99%
  • Shanghai Yunao International Trade Co., Ltd
Altal Celluflex TPP celluflextpp Disflamoll TP disflamolltp Dymel TRIPHENYL PHOSPHATE (TPP) Tripheyl phosphate Triphenyl hosphate TRIPHENYL PHOSPHATE, 99+% TRIPHENYL PHOSPHATE FREE OF PHENOL NMR REF STD, 0.0485M TRIPHENYLPHOSPHATE IN CHLOROFORM-D, 99.9 ATOM % D TRIPHENYL PHOSPHATE, 1000MG, NEAT TRIPHENYLPHOSPHATE, 1X1ML, MTBE, 500UG/M L NMR REF STD, 0.0485M TRIPHENYLPHOSPHATEIN CHLOROFORM-D,99.8 ATOM % D Tppa(TriphenylPhosphate) AURORA KA-1647 PHOSPHORIC ACID TRIPHENYL ESTER Phosphorictri phenylester TPP TRIPHENYL PHOSPHATE PLASTICIZERS FOR PRINTING INKS Triphenylphosphate,98% TRIPHENYLPHOSPHATE,REAGENT BUTYLATEDTRIPHENYLPHOSPHATEHYDRAULICFLUID Phosphorsuretriphenylester O,O,O-Trisphenylphosphate Triphenylphosp TPPa(Triphenyl phoaphate) Palamoll 654 Flame Retardant TPP Kronitex TPP Phenyl phosphate ((PhO)3PO) phenylphosphate((pho)3po) Phosflex TPP phosflextpp phosphatedetriphenyle Trifenylfosfat Triphenoxyphosphine oxide triphenoxyphosphineoxide Triphenyl phosphoric acid ester NMR reference standard, triphenylphosphate in chloroform-d Triphenyl phosphate solution Plastifier Phosphoric acid triphenyl TRIPHENYL PHOSPHATE(P) Triphenyl phosphate 5g [115-86-6] Triphenyl phosphate 10g [115-86-6] NMR REF STD, 0.0485M TRIPHENYLPHOSPHATE IN CHLOROFORM-D, 99.8 ATOM % D (10MM X 8IN TUBE, CONTAINS 3.175ML ) Triphenyl phosphate, 99+% 1KG NSC 57868 Phoscon FR 903N Reofos TPP SuMilizer TPP TPPA Wako TPP Triphenylphosphate @0.5 mg/mL in MtBE Triphenylphosphate@100 μg/mL in MeOH