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CAS NO:78-32-0
EC NO:201-105-6
Tricresyl phosphate (TCP), is a mixture of three isomeric organophosphate compounds most notably used as a fire retardant and in manufacturing for lacquers and varnishes as a plasticizer.
Tricresyl phosphate is a colorless, viscous liquid, although commercial samples are typically yellow.
Tricresyl phosphate is virtually insoluble in water, but easily soluble in organic solvents like toluene, hexane, and diethylether among others.
Tricresyl phosphate was synthesized by Alexander Williamson in 1854 upon reacting phosphorus pentachloride with cresol (a mixture of para-, ortho-, and meta- isomers of methylphenol), though today's manufacturers can prepare TCP by mixing cresol with phosphorus oxychloride or phosphoric acid as well.
Tricresyl phosphate, especially the all-ortho isomer, is the causative agent in a number of acute poisonings.
Tricresyl phosphates chronic toxicity is also of concern. The ortho-isomer is rarely used on its own due to its extremely toxic nature outside of laboratory studies that require isomeric purity, and is generally excluded from commercial products where Tricresyl phosphate is involved.
Properties
Chemical formula C21H21O4P
Molar mass 368.37 g/mol
Appearance colourless liquid
Melting point −40 °C (−40 °F; 233 K)
Boiling point 255 °C (491 °F; 528 K) (10 mmHg)
A mixture of isomeric tritolyl phosphates. Used in the sterilization of certain surgical instruments and in many industrial processes.
USES
-Plasticizer in vinyl plastics manufacture, flame-retardant, solvent for nitrocellulose, in cellulosic molding compositions, as additive to extreme pressure lubricants, non-flammable fluid in hydraulic systems, as lead scavenger in gasoline, to sterilize certain surgical instruments /Isomeric mixture/
-Aryl phosphates such as tricresyl phosphate ... when added in small percentages to the gasoline, combat misfires. /Aryl phosphates/
-The commercial tricresyl phosphate product is essentially a meta, para-isomer mixture. Tricresyl phosphate is used in flexible PVC, cellulose nitrate, ethylcellulose coatings, and various rubbers. Typical applications are vinyl tarpaulins, mine conveyer belts, air ducts, cable insulation, and vinyl films ... usually used in blends with phthalates.
Tricresyl phosphate is used as a plasticizer in vinyl plastic manufac- ture, as a flame-retardant, a solvent for nitrocellulose, in cellulosic molding compositions, as an additive to extreme pressure lubricants, and as a non-flammable fluid in hydraulic systems .
Tricresyl Phosphate (TCP), also called tricresylphosphate, tritolyl phosphate, tolyl phosphate, or tri-o-tolyl ester of phosphoric acid, is an organic compound, an organophosphate, an ester of phosphoric acid.
Leather cloth (PVC): Upholstery, Book binding. Seat covers
Utility articles: Footwear, Raincoats, Handbags, Fiberglass, cellulose acetate
Extruded articles: Cables (PVC & rubber), hoses, flexible pipe, coal mining, conveyor belts
Coatings: Nitrocellulose lacquers, phenolic resins, lube oils
APPLICATIONS
Tricresyl Phosphate is used plasticizers for vinyl films in agriculture due to its weather resistance property
Insulator compounds for electric cables and also in the synthetic rubber compounds.
Lubricant additive and has been proven effective as mild extreme pressure addictive for synthetic oil.
Based oil for fire-retardant hydraulic fluid for minimizing fire-risk from heat source or electric sparks.
Tricresyl Phosphate is useful in the clear and dark coloured flame-retardant sheeting where pigmenting or opecifying flame retardants are undesirable
Specifications
Melting Point -30°C
Boiling Point 265°C
Quantity 1L
Color Yellow
Density 1.160g/cm³
Vapor Density 12.70g/mol
Identification Pass Test
Packaging Glass Bottle
Vapor Pressure 0.03mmHg at 25°C
Linear Formula (CH3C6H4O)3PO
Where is tricresyl phosphate found?
Tricresyl phosphate is a plasticizer used in lacquers, varnishes, and as a flame retardant in plastics and rubbers.
Tricresyl phosphate is used as a gasoline additive, in waterproofing materials, in hydraulic fluids, and lubricants.
Chemical Properties
Tricresyl 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 phosphates were used as flame retardants and plasticisers in PVC, nitrocellulose and acrylates.
Uses
Tricresyl phosphate (TCP) is used as a solvent for nitrocellulose esters and numerous natural resins.
Tricresyl phosphat 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.
Tricresyl phosphat 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.
Uses
Tricresyl 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.
Uses
Tricresyl 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.
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.
Uses:
Tricresyl phosphate is used as a plasticizer in vinyl plastics manufacturing, in spectacle frames, as a flame-retardant, as a solvent for nitrocellulose and in cellulose molding compositions.
Tricresyl phosphate is also used as an additive to extreme-pressure lubricants, as a nonflammable fluid in hydraulic systems, as a lead scavenger in gasoline, to sterilize certain surgical instruments, in polystyrene, in waterproofing, in common organic solvents and thinners, in linseed oil, as emulsifying agent in cosmetics, in china wood oil and in castor oil
Uses
Extreme pressure lubricant
Flame retarder
Lead scavenger in gasoline
Plasticizer in vinyl plastics, spectacle frames
Solvent for nitrocellulose
Sterilizer for certain surgical instruments
Chemical Properties
Formula
(CH3C6H4O)3P(O)
Formula Weight
368.37
Form
Liquid
Boiling Point
265°/10mm
Flash Point
250°(482°F)
Density
1.167
Storage & Sensitivity
Ambient temperatures.
Applications
Plasticizer, flame-retardant, nitrocellulose solvent
The name tricresyl phosphate is used as a common name for the ten substances and for mixtures of these. The relative content of the different cresyl moieties depends on the cresols used in the production of tricresyl phosphate. Industrial-grade tricresyl phosphate contains predominately the meta- and para-isomers and modern mixtures contain less than 1% of the ortho-isomer.
Colorless or pale yellow, oily liquid. Tricresyl phosphate is used as a solvent and plasticizer in Polyvinyl chloride, Cellulose nitrate, Mastic and some commercial lacquer formulations. It is also used industrially as a flame retardant, a Lead Scavenger in Gasoline, and a waterproofing agent.
Tricresyl Phosphate (TCP) is widely used as an anti-wear additive for lubrication and hydraulic fluid technology in aerospace propulsion systems. However, there is no clear description of the chemistry involved in the conversion of TCP to an anti-wear film on metal surfaces.
Tricresyl phosphate, abbreviated TCP, is an organophosphate compound.
Tricresyl phosphate is a derived from cresol and phosphoric acid. This viscous liquid is colourless when pure, but commercial samples are typically yellow.
Tricresyl phosphate is nonflammable and virtually insoluble in water.
Uses
Tricresyl phosphate is used as a plasticizer in nitrocellulose, acrylate lacquers, varnishes, and in polyvinyl chloride.
Tricresyl phosphate is a flame retardant in plastics and rubbers.
Tricresyl phosphate is used as a gasoline additive as a lead scavenger for tetra-ethyl lead.
Tricresyl phosphate is a hydraulic fluid and a heat exchange medium. Exploiting its hydrophobic properties, it is used in waterproofing of materials.
Tricresyl phosphate is a solvent for extractions, a solvent for nitrocellulose and other polymers.
Tricresyl phosphate is also used as an AW additive and EP additive in lubricants, and in hydraulic fluids. As a gasoline additive, it also helps preventing engine misfires.
Tricresyl phosphate is an oily flame-resistant mixture of isomeric inorganic esters (CH3C6H4)3PO4 made from cresols or cresylic acid and usually phosphorus oxychloride and used chiefly as a plasticizer and solvent, as a fire retardant, and as a lead scavenger in gasoline : tritolyl phosphate —not used systematically
Tricresyl Phosphate is a colorless, odorless liquid that is a mixture of three different isomers.
Tricresyl Phosphate is used as an additive in lubricating oils and a plasticizer, and as a fire retardant.
Tricresyl Phosphate is an odorless, colorless, industrial, and organophosphorus chemical.
Tricresyl Phosphate is used in lacquers and varnishes as a plasticizer and also in hydraulic fluid.
Tricresyl phosphate (TCP), also called tricresylphosphate, tri-o-cresyl phosphate (TOCP), tritolyl phosphate, tolyl phosphate, or tri-o-tolyl ester of phosphoric acid, is an organic compound, an organophosphate, an ester of phosphoric acid.
Tricresyl phosphate is a colorless or pale yellow viscous virtually nonflammable liquid insoluble in water, with melting point at -40 °C and boiling point at 240-255 °C.
Tricresyl phosphates flash point is above 225 °C. Its chemical formula is C21H21O4P.
Tricresyl Phosphate is a known neurotoxin. Liquid tricresyl phosphate is irritiating to skin and eyes. At high temperatures, vapors are irritating to eyes.
Tricresyl phosphate is manufactured by reaction of cresols with phosphorus oxychloride.
In alkaline medium it undergoes hydrolysis to cresol and dicresyl phosphate.
Uses
Tricresyl phosphate is used as a plasticizer in nitrocellulose and acrylate lacquers and varnishes and in polyvinyl chloride, a flame retardant in plastics and rubbers, as a gasoline additive as a lead scavenger for tetra-ethyl lead, in hydraulic fluids, as a heat exchange medium, for waterproofing of materials, as a solvent for extractions, a solvent for nitrocellulose and other polymers, and an intermediate in organic synthesis.
Tricresyl phosphate is also used as an AW additive and EP additive in lubricants, and as a hydraulic fluid. As a gasoline additive, it also helps preventing engine misfires.
Tricresyl phosphate (TCP) is a non-flammable, viscous clear liquid; insoluble in water,
Tricresyl phosphate is stable in neutral and acidic media at normal temperatures. But it is readily hydrolysed in an alkaline medium, producing dicresyl phosphate and cresol. Commercial TCP is the mixture of isomers (ortho-, meta-, and para-isomers).
Tricresyl phosphate is produced by the reaction of cresols (or cresylic acid) with phosphorus oxychloride.
Tricresyl phosphate is used;
as a solvent and thinner for nitrocellulose, paints acrylate lacquers, and varnishes.
as a plasticizer for PVC processing
as an ingredient for flame-retardant in plastics, rubbers and in hydraulic systems.
as a heat exchange media
as an additive in high-pressure cooling lubricants
as a lead scavenger in gasoline.
The chemistry, mechanism and function of tricresyl phosphate (TCP) as an anti-wear lubricant additive
Tricresyl phosphate (TCP) is a widely used and effective antiwear additive for a variety of lubricants used in aerospace military applications. However, for a high-temperature gas turbine engine oil (GTO) application, volatility and thermo-oxidative stability limitations preclude the use of TCP. For this GTO application, high molecular weight, and thermally and thermo-oxidatively stable groups were incorporated into a phosphate-based additive.
IUPAC names
Phosphoric acid, tris(4-methylphenyl) ester
Tri-p-cresyl Phosphate
Tri-p-tolyl phosphate
tri-p-tolyl phosphate
tricresyl phosphate (m-m-m-, m-m-p-, m-p-p-, p-p-p-)
Tricresyl Phosphate （Mixed isomer)
tris(4-methylphenyl) phosphate
tritolyl phosphate (m-m-m-, m-m-p-, m-p-p-, p-p-p-)
SYNONYMS:
1330-78-5 [RN]
201-105-6 [EINECS]
Phosphate de tris(4-méthylphényle) [French] [ACD/IUPAC Name]
Phosphoric acid, tri-p-tolyl ester (8CI)
Phosphoric acid, tris(4-methylphenyl) ester [ACD/Index Name]
Tricresyl phosphate (Tritolyl phosphate)
TRI-P-CRESYL PHOSPHATE
Tris(4-methylphenyl) phosphate [ACD/IUPAC Name]
Tris(4-methylphenyl)phosphat [German] [ACD/IUPAC Name]
[1330-78-5]
[78-32-0]
1336-40-9 [RN]
4-06-00-01979 (Beilstein Handbook Reference) [Beilstein]
4-methylphenyl di4-methylphenyl phosphate
EINECS 201-103-5
EINECS 201-105-6
hydroxy-tris(2-methylphenoxy)phosphanium
hydroxy-tris(2-methylphenoxy)phosphonium
MFCD00041908 [MDL number]
MFCD02102116 [MDL number]
o-Cresyl phosphate
o-tolyl phosphate
o-Trikesylphosphate
o-Trikresylphosphate [German]
Phosflex 179C
Phosphoric Acid Tricresyl Ester
phosphoric acid tri-p-cresyl ester
phosphoric acid tri-p-tolyl ester
Phosphoric acid tris(2-methylphenyl) ester
Phosphoric Acid Tris(4-methylphenyl) Ester
Phosphoric Acid Tris(4-​methylphenyl) Ester
Phosphoric acid tris(4-methylphenyl) ester
