Tricresyl Phosphate

Tricresyl Phosphate Basic information
Product Name:Tricresyl Phosphate
Synonyms:Tris(hydroxymethylbenzol)phosphate (containing o-isomers <3%);Tri-p-tolylphosphate 1g [1330-78-5];Tricresyl Phosphate ;Tritolyl phosphate, Mixture of isoMers, 99% 25GR;Phosphoric Acid Tritolyl Ester Phosphoric Acid Tricresyl Ester Tritolyl Phosphate;Tricresyl phosphat;Tricresyl phosphate, 99%, Mixture of isoMers;Tritolyl Phosphate, Technical
CAS:1330-78-5
MF:C21H21O4P
MW:368.36
EINECS:809-930-9
Product Categories:Organic Building Blocks;Organic Phosphates/Phosphites;Phosphates (Plasticizer);Plasticizer;Phosphorus Compounds;Organic synthesis;Functional Materials
Mol File:1330-78-5.mol
Tricresyl Phosphate Structure
Tricresyl Phosphate Chemical Properties
Melting point <-40°C
Boiling point 265 °C10 mm Hg(lit.)
density 1.143 g/mL at 25 °C(lit.)
vapor pressure 0.03 mm Hg ( 25 °C)
refractive index n20/D 1.555(lit.)
Fp >230 °F
storage temp. Store below +30°C.
solubility organic solvents: miscible(lit.)
form Powder
color White to off-white
Water Solubility INSOLUBLE
Merck 14,9763
Stability:Stable. Incompatible with strong oxidizing agents. May soften some plastics. Hydrolyzes slowly under alkaline conditions.
InChIKeyISNNXHQBIBWQHG-UHFFFAOYSA-N
LogP5.93
CAS DataBase Reference1330-78-5(CAS DataBase Reference)
EPA Substance Registry SystemTricresyl phosphate (1330-78-5)
Safety Information
Hazard Codes Xn,N,T
Risk Statements 21/22-51/53-39/23/24/25-62-50/53
Safety Statements 28-61-45-28A-20/21-60-36/37
RIDADR UN 2574 6.1/PG 2
WGK Germany 2
RTECS TD0175000
Autoignition Temperature770 °F
TSCA Yes
HS Code 2919 90 00
HazardClass 6.1
PackingGroup II
Hazardous Substances Data1330-78-5(Hazardous Substances Data)
Toxicitycat,LD50,skin,1500mg/kg (1500mg/kg),BEHAVIORAL: ATAXIAPERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE),Toxicology Letters. Vol. 1000(Sp,
MSDS Information
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Tritolyl phosphate English
SigmaAldrich English
ACROS English
ALFA English
Tricresyl Phosphate Usage And Synthesis
Chemical PropertiesTricresyl phosphate is an isomeric mixture of phosphoric acid esters of cresols. It is an odourless and colourless oily liquid (molar mass 368.4 g/mol, melting point –33°C).
Tricresyl phosphate
Tricresyl phosphates were used as flame retardants and plasticisers in PVC, nitrocellulose and acrylates.
UsesTricresyl phosphate (TCP) is used as a solvent for nitrocellulose esters and numerous natural resins. It is a plasticizer for chlorinated rubber, vinyl plastics, polystyrene and polyacrylic and polymethacrylic esters. Tricresyl phosphate also acts as a binder for resins and nitrocellulose to improve toughness, elasticity and polishing properties of coatings. Alone or associated with hydrocarbons, it is used as an antiwear and antifriction additive in numerous synthetic lubricants, incorrectly termed “oils” by reason of their appearance. It is also employed as a hydraulic fluid. When incorporated in gasoline, tricresyl phosphate counteracts the harmful effects of lead deposits. In addition, it is an excellent fire retardant in many industries.
Usually used as a mediator in the preparation of uranium-sensitive electrode based on membrane containing uranium di-(4-octylphenyl)phosphate as sensor.
UsesTricresyl Phosphate is used as plasticizer in vinyl plastics manufacture, as flame-retardant, solvent for nitrocellulose, in cellulosic molding compositions, as additive to extreme pressure lubricants, as a nonflammable fluid in hydraulic systems, as lead scavenger in gasoline: Yust, Bame, US 2889212 (1959 to Shell); to sterilize certain surgical instruments.
UsesTricresyl phosphate is used as plasticizer in vinyl plastics manufacturing; in spectacle frames; flame-retardant; solvent for nitrocellulose; in cellulose-molding compositions; additive to extreme-pressure lubricants; nonflammable fluid in hydraulic systems; lead scavenger in gasoline; used to sterilize certain surgical instruments; in polystyrene; in waterproofing; in common organic solvents and thinners; in linseed oil; emulsifying agent in cosmetics; in china wood oil; in castor oil.
PreparationTricresyl phosphate is prepared by reaction of cresols with phosphorus oxychloride, phosphoric acid, or phosphorus pentachloride:
OPCl3 + 3 HOC6H4CH3 → OP(OC6H4CH3)3 + 3 HCl
The grades of cresol commonly is a mixture of three isomers (o-, m-, p-). The fact that tricresyl phosphate is derived from a mixture and itself is a mixture ensures that it remains liquid over a wide span of temperatures.
A "refined grade" of tricresyl phosphate is prepared by vacuum distillation, or alternatively by washing with 2% sodium hydroxide and water.
Health HazardThe tricresyl phosphates (TCPs) are part of a series of organophosphorus compounds which have been shown to cause delayed neurotoxicity. The 1930 outbreak of “ginger jake” paralysis was caused by the contamination of ginger extract by cresyl phosphates, used in the processing of the spice. Since that time, there have been several incidents reported of accidental poisoning of food by tri-o-cresyl phosphate (TOCP). There are few case series reports of occupational exposure in the literature. Acute occupational exposures have been described as causing gastrointestinal symptoms followed by a latent period of days to 4 weeks, after which extremity pain and tingling progress to motor paralysis of the lower extremities up to the thighs, and of the upper extremities to the elbow. There is rarely sensory loss. Partial to total recovery may take years. Fatalities have occurred in high-dose ingestion.
Safety ProfileModerately toxic by ingestion and skin contact. Human systemic effects by ingestion: flaccid paralysis without anesthesia, motor activity changes, and muscle weakness. An experimental teratogen. Experimental reproductive effects. An eye and skin irritant. Combustible. When heated to decomposition it emits toxic fumes of POx.
Potential ExposureAccording to the World Health Organization there is no safe level of exposure to Tricresyl Phosphate(TCP).
TCP has been used as a flame retardant in fabric, plastics and rubbers and as a plasticizer in PVC, lacquers, varnishes and nitrocellulose. It is also used as a heat exchange medium and hydraulic fluid. TCP was detected in all house dust samples gathered in two different North American studies.Biomonitoring studies detected TCP in the breast milk of women in Asia and Sweden. EPA has characterized TCP to exhibit moderate persistence in the environment based on biodegradation studies.
Purification MethodsDry the ester with CaCl2, percolate it through a column of alumina, then distil it under a vacuum. Alernatively pass it through a packed column of alumina at 150o, with a counter-current stream of nitrogen, under reduced pressure, to remove residual traces of volatile impurities. It also crystallises from pet ether (b 60-80o). [Cherbuliez in Organic Phosphorus Compounds (Kosolapoff & Maier eds) Wiley-Interscience Vol 6 pp 454-457 1973.]
Toxicity evaluationTricresyl Phosphate is classified by the EPA as a high hazard for reproductive toxicity based on studies of rodents fed TCP. Adverse health effects included reduced fertility, sperm motility, number of live pups per litter, testicular and epidydimal weights, and increased incidence of interstitial cell hypertrophy and ovarian interstitial cell vacuolization.
Ovarian and adrenal gland lesions were observed in rats and liver and adrenal gland lesions in mice fed an isomer mixture of TCP for 2 years in an NTP study. Rodents fed TCP for 13 weeks developed neuropathy.
TCP has been shown to influence neurological damage in humans.
There are three tricresyl phosphate isomers, of which, the ortho isomer demonstrates the highest toxicity.
Tricresyl Phosphate Preparation Products And Raw materials
Raw materialsPhosphorus oxychloride-->Chlorine-->Xylenol
Preparation ProductsTri-o-cresyl Phosphate
ISOPROPYLPHENYLDIPHENYL PHOSPHATE 1,2,4-Trimethylbenzene Benzotrifluoride Tylosin phosphate Triethyl phosphate Trimethyl phosphate Calcium phosphate Diphenyl phosphate Trisodium phosphate Sodium Phosphate Monobasic Monohydrate Triphenyl phosphite Zinc phosphate TRITON phosphate Tri(o-tolyl)phosphine Clindamycin phosphate Tricresyl Phosphate Triphenyl phosphate

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