Triphenyl phosphate

1.1 Name

Triphenyl phosphate

1.2 Synonyms

Altal Celluflex TPP celluflextpp Disflamoll TP disflamolltp Dymel EINECS 204-112-2 MFCD00003031 Phenyl phosphate Phosflex TPP Phosphoric Acid Triphenyl Ester Phosphoric acid,triphenyl ester TPP tricresyl phosphate Triphenoxyphosphine oxide TRIPHENYL PHOSPHATE (TPP) Triphenylphosphate Tripheyl phosphate

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1.3 CAS No.

115-86-6

1.4 CID

8289

1.5 EINECS(EC#)

204-112-2

1.6 Molecular Formula

C18H15O4P (isomer)

1.7 Inchi

InChI=1S/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

1.8 InChkey

XZZNDPSIHUTMOC-UHFFFAOYSA-N

1.9 Canonical Smiles

C1=CC=C(C=C1)OP(=O)(OC2=CC=CC=C2)OC3=CC=CC=C3

1.10 Isomers Smiles

C1=CC=C(C=C1)OP(=O)(OC2=CC=CC=C2)OC3=CC=CC=C3

2.1 Density

247

2.1 Melting point

47-53℃

2.1 Boiling point

370℃

2.1 Refractive index

1.563

2.1 Flash Point

220℃

2.2 Precise Quality

326.07100

2.2 PSA

54.57000

2.2 logP

5.33150

2.2 Solubility

H2O: soluble0.0019g/L at 20°C

2.3 VaporDensity

1.19 (Air = 1)

2.4 Appearance

Triphenyl phosphate appears as colorless crystals. (NTP, 1992)

2.5 Storage

Ambient temperatures.

2.6 Color/Form

CRYSTALS FROM ABSOLUTE ALCOHOL-LIGROIN, PRISMS FROM ALCOHOL, NEEDLES FROM ETHER-LIGROIN
Colorless, crystalline powder
WHITE PLATELETS

2.7 Decomposition

Hazardous decomposition products: Toxic gases and vapors (such as phosphoric acid fume and carbon monoxide) may be released in a fire involving triphenyl phosphate.

2.8 Odor

Odorless

2.9 Water Solubility

H2O: insoluble

2.10 Spectral Properties

Index of refraction: 1.550 @ 60 deg C
Intense mass spectral peaks: 65 m/z (100%), 77 m/z (83%), 326 m/z (67%), 325 m/z (62%)
IR: 18528 (Sadtler Research Laboratories IR Grating Collection)
UV: 3-682 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
NMR: 10231 (Sadtler Research Laboratories Spectral Collection)
MASS: 26529 (NIST/EPA/MSDC Mass Spectra Database, 1990 Version)

2.11 Stability

Stable.

2.12 StorageTemp

Store below +30°C.

3.1 Definition

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

3.2 Potential Exposure

Triphenyl phosphate is used toimpregnate roofing paper and as a fire-resistant plasticizerin plastics; for cellulose esters in lacquers and varnishes.Used in making adhesives, gasoline additives; flotationagents; insecticides, surfactants, antioxidants, and stabilizers.A substitute for camphor.

3.3 Produe Method

Prepared by reacting phosphorus pentoxide and phenol and by reaction of triethylphosphate and chloramine-T. On a larger scale phosphorus oxychloride andphenol are reacted in an esterification tank with heating. The HCL formed istrapped and condensed, while the crude triphenyl phosphate runs into a large tankwhere it is purified.

3.4 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.]

3.5 Shipping

UN3077 Environmentally hazardous substances,solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardousmaterial, Technical Name Required.

3.6 Usage

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

3.7 Waste Disposal

Incinerate in furnaceequipped with alkaline scrubber. Triphenyl phosphate Preparation Products And Raw materials Raw materials

4.1 Symbol

GHS09

4.1 Hazard Codes

N

4.1 Signal Word

Warning

4.1 Risk Statements

R50/53

4.1 Safety Statements

S60;S61

4.1 Exposure Standards and Regulations

Triphenylphosphate is an indirect food additive for use only as a component of adhesives.

4.2 Packing Group

III

4.2 Octanol/Water Partition Coefficient

log Kow = 4.59

4.3 Other Preventative Measures

...Handle... with caution, prevent contact with skin, and keep air concentration below recommended values.

4.4 Hazard Class

9

4.4 Hazard Declaration

H410

4.4 Cleanup Methods

If triphenyl phosphate is spilled ... : ventilate area of spill. For small quantities, sweep onto paper or other suitable material, place in appropriate container and burn in a safe place (such as a fume hood). Large quantities may be reclaimed; however, if this is not practical, dissolve in a flammable solvent (such as alcohol) and atomize in a suitable combustion chamber equipped with an appropriate effluent gas cleaning device.

4.5 DisposalMethods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/
Group II Containers: Non-combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple-rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in adesignated landfill. /Organic or metallo-organic pesticides/
1. By making packages of triphenyl phosphate in paper or other flammable material and burning in a suitable combustion chamber... with an appropriate effluent gas cleaning device. 2. By dissolving... in a flammable solvent... and atomizing in a suitable combustion chamber... with an... effluent gas cleaning device.

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4.6 RIDADR

UN 3077

4.6 Fire Fighting Procedures

To fight fire, use carbon dioxide or dry chemical.

4.7 FirePotential

Combustible when exposed to heat or flame.

4.8 Safety Profile

Poison bysubcutaneous route. Moderately toxic byingestion. Absorbed slowly, particularly byskin contact. Not a potent cholinesteraseinhibitor. Combustible when exposed toheat or flame. To fight fire, use CO2, drychemical. When heated to decomposition itemits toxic fumes of POx. See alsoTRITOLYL PHOSPHATE.

4.9 Caution Statement

P273-P501

4.9 Formulations/Preparations

Technical
Trade Name: Phosflex

4.10 Incompatibilities

Incompatible with strong oxidizers;strong acids; nitrates may cause fire or explosions.Phosphates are incompatible with antimony pentachloride,magnesium, silver nitrate, zinc acetate.

4.11 WGK Germany

2

4.11 RTECS

TC8400000

4.11 Protective Equipment and Clothing

Respirator Recommendations: Up to 15 mg/cu m: (Assigned protection factor = 5) Any dust respirator.
Respirator Recommendations: Up to 30 mg/cu m: (Assigned protection factor = 10) Any air-purifying respirator with a high-efficiency particulate filter/ (Assigned protection factor = 10) Any dust rrespirator except single-use and quarter-mask respirators/ (Assigned protection factor = 10) Any supplied-air respirator.
Respirator Recommendations: Up to 75 mg/cu m: (Assigned protection factor = 25) Any supplied-air respirator operated in a continuous flow mode/ (Assigned protection factor = 25) Any powered, air-purifying respirator with a dust and mist filter.
Respirator Recommendations: Up to 150 mg/cu m: (Assigned protection factor = 50) Any air-purifying, full-facepiece respirator with a high-efficiency particulate filter/ (Assigned protection factor = 50) Any supplied-air respirator that has a tight-fitting facepiece and is operated in a continuous-flow mode/ (Assigned protection factor = 50) Any powered, air-purifying respirator with a tight-fitting facepiece and a high-efficiency particulate filter/ (Assigned protection factor = 50) Any self-contained breathing apparatus with a full facepiece/ (Assigned protection factor = 50) Any supplied-air respirator with a full facepiece.
Respirator Recommendations: Up to 1000 mg/cu m: (Assigned protection factor = 1000) Any supplied-air respirator operated in a pressure-demand or other positive-pressure mode.
Respirator Recommendations: Emergency or planned entry into unknown concentrations or IDLH conditions: (Assigned protection factor = 10,000) Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive pressure mode/ (Assigned protection factor = 10,000) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.
Respirator Recommendations: Escape: (Assigned protection factor = 50) Any air-purifying, full-facepiece respirator with a high-efficiency particulate filter/ Any appropriate escape-type, self-contained breathing apparatus.
Wear rubber gloves, self-contained breathing apparatus and overalls.
Respiratory protection (supplied-air respirator with full facepiece or self-contained breathing apparatus) should be available where these compounds are manufactured or used and should be worn in case of emergency and overexposure. /Phosphorus compounds/

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4.12 Reactivities and Incompatibilities

A marked change is noted in the taste and smell of solns stored in containers made of etrol, which has been plasticized with TPP.

4.13 Toxicity

LD50 orally in Rabbit: 3500 mg/kg LD50 dermal Rabbit > 7900 mg/kg

9.0 Merck

14,9742

9.1 BRN

1888236

9.2 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).

9.3 Uses

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

9.4 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).

9.5 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..

9.6 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.

9.7 Definition

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

9.8 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.

9.9 Hazard

Toxic by inhalation. Cholinesterase inhibitor. Questionable carcinogen.

9.10 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).

9.11 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..

9.12 Fire Hazard

Noncombustible solid. Incompatibility— none.

9.13 Industrial uses

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

9.14 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.

9.15 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.

9.16 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).

9.17 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)

9.18 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).

9.19 Shipping

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

9.20 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.]

9.21 Incompatibilities

Incompatible with strong oxidizers; strong acids; nitrates may cause fire or explosions. Phosphates are incompatible with antimony pentachloride, magnesium, silver nitrate, zinc acetate.

9.22 Waste Disposal

Incinerate in furnace equipped with alkaline scrubber.

9.23 Storage features

Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

9.24 Usage

Triphenyl phosphate is used as an internal standard in the screening and quantification of agrochemical residues in vegetables and fruits. It is used in plastic processing and molding of plastic flow and performance.

• Molecular Weight: 326.283061g/mol
• Molecular Formula: C₁₈H₁₅O₄P
• Compound Is Canonicalized: True
• XLogP3-AA: null
• Exact Mass: 326.07079595
• Monoisotopic Mass: 326.07079595
• Complexity: 325
• Rotatable Bond Count: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Topological Polar Surface Area: 44.8
• Heavy Atom Count: 23
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• Isotope Atom Count: 0
• Covalently-Bonded Unit Count: 1
• CACTVS Substructure Key Fingerprint: AAADccB4OAIAAAAAAAAAAAAAAAAAAAAAAAAwYMAAAAAAAAABUAAAGgAAACAACASAkAAwBoAAARCAQCBCAIACAAAgIAAIiAAGCIgIJiKAERKAMAAkwBEIiAeAQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==