1330-78-5

Basic information

• Product Name: Tritolyl phosphate
• Synonyms: Tris(hydroxymethylbenzol)phosphate (containing o-isomers ;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 NO: 1330-78-5
• Molecular Formula: C21H21O4P
• Molecular Weight: 368.36
• EINECS: 215-548-8
• Product Categories: Phosphates (Plasticizer);Plasticizer;Organic Building Blocks;Organic Phosphates/Phosphites;Phosphorus Compounds;Organic synthesis;Functional Materials
• Mol File: 1330-78-5.mol
• Article Data: 0

Chemical Properties

• Melting Point: -33℃
• Boiling Point: 265 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White to off-white/Powder
• Density: 1.143 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.03 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.555(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: organic solvents: miscible(lit.)
• Water Solubility: INSOLUBLE
• Stability: Stable. Incompatible with strong oxidizing agents. May soften some plastics. Hydrolyzes slowly under alkaline conditions.
• Merck: 14,9763
• CAS DataBase Reference: Tritolyl phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: Tritolyl phosphate(1330-78-5)
• EPA Substance Registry System: Tritolyl phosphate(1330-78-5)

Safety Data

• Hazard Codes: Xn,N,T
• 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
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 1330-78-5(Hazardous Substances Data)

Usage

Description

Tricyl phosphate, also known as tricresyl phosphate, is an isomeric mixture of phosphoric acid esters of cresols. It is an odorless and colorless oily liquid with a molar mass of 368.4 g/mol and a melting point of -33°C.

Uses

Used in Plastics Industry:
Tricyl phosphate is used as a plasticizer in vinyl plastics manufacturing, imparting flexibility and workability to the material.
Used in Coatings Industry:
Tricyl phosphate is used as a binder for resins and nitrocellulose, improving the toughness, elasticity, and polishing properties of coatings.
Used in Lubricants Industry:
Tricyl phosphate is used as an antiwear and antifriction additive in numerous synthetic lubricants, enhancing their performance and longevity.
Used in Gasoline Industry:
When incorporated in gasoline, tricyl phosphate counteracts the harmful effects of lead deposits, improving engine performance and reducing emissions.
Used in Hydraulic Systems:
Tricyl phosphate is used as a nonflammable fluid in hydraulic systems, providing a safe and efficient means of transferring power.
Used in Flame Retardants:
Tricyl phosphate is used as a flame retardant in various industries, reducing the risk of fire and improving safety.
Used in Spectacle Frames:
Tricyl phosphate is used in the manufacturing of spectacle frames, providing flexibility and durability.
Used in Cosmetics:
Tricyl phosphate is used as an emulsifying agent in cosmetics, helping to create stable and effective formulations.
Used in Medical Instruments:
Tricyl phosphate is used to sterilize certain surgical instruments, ensuring cleanliness and safety during medical procedures.
Used in Solvents:
Tricyl phosphate is used as a solvent for nitrocellulose, cellulose-molding compositions, and common organic solvents and thinners, providing a versatile and effective means of dissolving various substances.
Used in Uranium-sensitive Electrode:
Tricyl phosphate is used as a mediator in the preparation of uranium-sensitive electrodes based on membranes containing uranium di-(4-octylphenyl)phosphate as a sensor, enabling the detection and measurement of uranium levels.

Preparation

Tricresyl 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 Hazard

The 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 Profile

Moderately 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 Exposure

According 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 Methods

Dry 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 evaluation

Tricresyl 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.

InChI:InChI=1/3C21H21O4P/c1-16-4-10-19(11-5-16)23-26(22,24-20-12-6-17(2)7-13-20)25-21-14-8-18(3)9-15-21;1-16-10-4-7-13-19(16)23-26(22,24-20-14-8-5-11-17(20)2)25-21-15-9-6-12-18(21)3;1-16-11-13-19(14-12-16)23-26(22,24-20-9-6-7-17(2)15-20)25-21-10-5-4-8-18(21)3/h3*4-15H,1-3H3