Triphenylphosphat

Bezeichnung:Triphenylphosphat

CAS-Nr115-86-6

Englisch Name:Triphenyl phosphate

CBNumberCB9233809

SummenformelC18H15O4P

Molgewicht326.28

MOL-Datei115-86-6.mol

Synonyma

Triphenylphosphat

Phosphors?uretriphenylester

TPP

Triphenylphosphat physikalisch-chemischer Eigenschaften

Schmelzpunkt	48-50 °C (lit.)
Siedepunkt	244 °C/10 mmHg (lit.)
Dichte	1.2055
Dampfdichte	11.3 (vs air)
Dampfdruck	1.3 mm Hg ( 200 °C)
Brechungsindex	1.563
Flammpunkt	435 °F
storage temp.	Store below +30°C.
Löslichkeit	H2O: soluble0.0019g/L at 20°C
Aggregatzustand	Crystalline Flakes
Farbe	White
Geruch (Odor)	Odorless
Wasserlöslichkeit	insoluble
Merck	14,9742
BRN	1888236
Henry's Law Constant	5.88 at 20 °C (approximate - calculated from water solubility and vapor pressure)
Expositionsgrenzwerte	TLV-TWA air 3 mg/m³ (ACGIH, OSHA, and NIOSH).
Stabilität	Stable.
InChIKey	XZZNDPSIHUTMOC-UHFFFAOYSA-N
LogP	4.6 at 20℃
CAS Datenbank	115-86-6(CAS DataBase Reference)
NIST chemische Informationen	Triphenylphosphate(115-86-6)
EPA chemische Informationen	Triphenyl phosphate (115-86-6)

Sicherheit

Kennzeichnung gefährlicher	Xn,N,F,Xi
R-Sätze:	22-38-40-48/20/22-50/53-52/53-36/37/38-67-66-36-11-51/53
S-Sätze:	36/37-61-60-24/25-22-36-26-16-24-9
RIDADR	UN 3077 9/PG 3
OEB	B
OEL	TWA: 3 mg/m3
WGK Germany	2
RTECS-Nr.	TC8400000
Selbstentzündungstemperatur	>500 °C
TSCA	Yes
HazardClass	9
PackingGroup	III
HS Code	29190010
Giftige Stoffe Daten	115-86-6(Hazardous Substances Data)
Toxizität	LD50 orally in Rabbit: 3500 mg/kg LD50 dermal Rabbit > 7900 mg/kg
IDLA	1,000 mg/m3

Gefahreninformationscode (GHS)

Triphenyl phosphate Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
FARBLOSES KRISTALLINES PULVER MIT CHARAKTERISTISCHEM GERUCH.
CHEMISCHE GEFAHREN
Beim Erhitzen bilden sich giftige Rauche.
ARBEITSPLATZGRENZWERTE
TLV: 3 mg/m?(als TWA); Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); (ACGIH 2008).
MAK: IIb (MAK nicht festgelegt, aber Informationen vorhanden) (DFG 2008).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation.
INHALATIONSGEFAHREN
Verdampfung bei 20°C vernachlässigbar; eine gesundheitsschädliche Partikelkonzentration in der Luft kann jedoch beim Versprühen oder Dispergieren schnell erreicht werden, vor allem als Pulver.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Möglich sind Auswirkungen auf das periphere Nervensystem mit nachfolgenden Funktionsstörungen.
LECKAGE
Verschüttetes Material in Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgfältig sammeln. An sicheren Ort bringen. Persönliche Schutzausrüstung: Atemschutzgerät, P2-Filter für schädliche Partikel. NICHT in die Umwelt gelangen lassen.
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R38:Reizt die Haut.
R40:Verdacht auf krebserzeugende Wirkung.
R48/20/22:Gesundheitsschädlich: Gefahr ernster Gesundheitsschäden bei längerer Exposition durch Einatmen und durch Verschlucken.
R50/53:Sehr giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R52/53:Schädlich für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S22:Staub nicht einatmen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S16:Von Zündquellen fernhalten - Nicht rauchen.
Chemische Eigenschaften
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).
Verwenden
Triphenyl phosphate is known as a product with manifold fields of applications regarding its qualities in particular as a flame retardant. 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).
Definition
ChEBI: Triphenyl phosphate is an aryl phosphate resulting from the formal condensation of phosphoric acid with 3 mol eq. of phenol. It has a role as a flame retardant and a plasticiser. It is functionally related to a phenol.
Application
Triphenyl Phosphate is used in the insecticidal composition. It is also use in hydraulic liquids, and adhesives, inks, coatings, as a plasticizer in lacquers and varnishes, and as a substitute for camphor in celluloid materials to make the latter stable and fireproof.
synthetische
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.
Reaktivität anzeigen
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.
Auswirkungen auf die Gesundheit
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).
Brandgefahr
Noncombustible solid. Incompatibility— none.
Sicherheitsprofil
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.
mögliche Exposition
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)
Stoffwechsel
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).
Versand/Shipping
UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
läuterung methode
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/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.
Inkompatibilitäten
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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