TRICRESYL PHOSPHATE

TRICRESYL PHOSPHATE

CAS NO: 1330-78-5
EC/LIST: 246-983-1

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. 
Pure tricresyl phosphate is a colorless, viscous liquid, although commercial samples are typically yellow. 
Tricresyl phosphateis virtually insoluble in water, but easily soluble in organic solvents like toluene, hexane, and diethylether among others. 
Tricresyl phosphatewas 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 Tricresyl phosphate 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 phosphate 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.

Tritolyl phosphate was used as a mediator in the preparation of uranium-sensitive electrode based on membrane containing uranium di-(4-octylphenyl)phosphate as sensor.

Tricresyl phosphate, abbreviated Tricresyl phosphate 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. 
Commercial tricresyl phosphate is a mixture of ortho, meta, and para-cresyl phosphates , the m- isomer 

Tricresyl phosphate (TCP) is an organophosphorous neurotoxin that has been detected in water, soil and air. 
Exposure to Tricresyl phosphate in cockpit and cabin air poses a severe threat to flight safety and the health of the aircraft cabin occupants. 
Conventional methods for the detection of Tricresyl phosphate in various samples are gas or liquid chromatography coupled to mass spectrometry, which are complex and expensive. 
To develop a simple low-cost methodology for the real-time monitoring of Tricresyl phosphate in the environment, an effective catalyst is demanded for the hydrolysis of Tricresyl phosphate under neutral condition. 
In this study, Ruthenium (III) hydroxide and Iron (III) hydroxide are found to facilitate the production of the alcoholysis and hydrolysis products of Tricresyl phosphate, suggesting their role as a catalyst. 
With this finding, these metal hydroxides provide new potential to realize not only simple colorimetric or electrochemical detection of Tricresyl phosphate, but also a simple detoxication strategy for Tricresyl phosphate in environment. 
In addition, the catalytic capability of Ru (III) or Fe (III) hydroxide for Tricresyl phosphate gives a hint that they can potentially serve as catalysts for the hydrolysis of alcolyolysis of many other organophosphate compounds.

TricresyI 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.

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.

This chemical is used as a softener in plastics manufacturing and as a flame retardant. 
Tricresyl phosphate can be found in spectacle frames, high-pressure lubricants, hydraulic fluids, gasoline, thinners, linseed oil, castor oil and in some cosmetics. 
Further research may identify additional product or industrial usages of this chemical

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 phosphate flash point is above 225 °C. 
Tricresyl phosphate 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 CAS number is [78-30-8] and its SMILES structure is O=P(Oc2ccccc2C)(Oc3ccccc3C)Oc1ccccc1C.

Commercial tricresyl phosphate is a mixture of ortho, meta, and para cresyl isomers. 
The mixture has CAS number [1330-78-5], the m- isomer is [563-04-2], the p- isomer is [78-32-0].

Tricresyl phosphate is manufactured by reaction of cresols with phosphorus oxychloride.

In alkaline medium it undergoes hydrolysis to cresol and dicresyl phosphate.

Tricresyl phosphate is manufactured by reaction of cresols with phosphorus oxychloride:

OPCl3 + 3 HOC6H4CH3 → OP(OC6H4CH3)3 + 3 HCl

In alkaline medium it undergoes hydrolysis to cresol and dicresyl phosphate.

OP(OC6H4CH3)3 + NaOH → + HOC6H4CH3 + NaO2P(OC6H4CH3)2

Parameters    :TCP
Structure    :(CH3 C6 H4 O)3 P
CAS No    :1330 – 78 – 5
Category    :Flame retardant,
Form    :Colorless to Pale Yellow Liquid
Specific gravity at 25 °C    :1.165 – 1.175
Acidic Value, mg KOH / gm    :0.5 max
Refractive Index at 25 °C    :1.540 – 1.560
Phosphorous Content %    :8.4 – 8.5 %

Appearance :Viscous
Physical State :Liquid
Solubility :Insoluble in cold water, hot water, methanol with all common organic solvents and thinners.
Storage :Store at room temperature
Melting Point :-33° C
Boiling Point :255° C (lit.) at 0.5 kPa
Density :1.14 g/cm3 at 25° C (lit.)

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.

Tricresyl Phosphate is one of industrial product, which is widely used in various industrial sectors. 
The initial design plant of Tricresyl Phosphate from cresoland phosphorus oxychloride planned in Gresik, East Java, in the area of ​​land is 12,310 m2 with capacity 15,000 tons/year. 
This plant will be operated for 330 days or 24 hours a day with 135 employees.
Tricresyl Phosphate made from 1,841,600kg/hour of cresol and820,148kg/hour of phosphorus oxychloride using a Continous Stirred Tank Reactor. 
The process of this reaction will be operated at temperature 150oC and pressure at 10 atm, the conversion of reaction is 80%. 
The utility needs 183,567kg/hour of water, 33,734.867 kg/hour of steam, and 235.55 kWelectricity provided by PLN and generator as a back up. 
The economic analysis shows the value of Fixed Capital Investment (FCI) is Rp 1,538,271,112,456.6; Working Capital Investment (WCI) is Rp 522,181,062,057.96;
Profit before tax is Rp 183,783,685,385.99; Profit after tax (50%) is Rp 91,891,842,692.9; 
Return On Investment before tax (ROI)b is 56.63% and Return On Investment after tax (ROI)a is 28.31%. 
Pay Out Time before tax (POT)b is 1.50 years and Pay Out Time after tax (POT)a is 2.61 years. 
Break Event Point (BEP) is 54.51% and Shut Down Point (SDP) is 44.06%. 
Discounted Cash Flow Rate (DCFR) 18.35%. 
Based on the evaluation results, this Tricresyl Phosphate plant with capacity of 15,000 tons/year was worthy for further analysis.

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.

The most dangerous isomers are considered to be those containing ortho isomers, such as tri-ortho-cresyl phosphate, TOCP. 
The World Health Organization stated in 1990 that "Because of considerable variation among individuals in sensitivity to TOCP, it is not possible to establish a safe level of exposure" and "TOCP are therefore considered major hazards to human health."
Therefore, strenuous efforts have been made to reduce the content of the ortho isomers in commercial Tricresyl phosphate if there is a risk of human exposure.
However, researchers at the University of Washington found that non-ortho Tricresyl phosphate isomers present in synthetic jet engine oils do inhibit certain enzymes

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

Tricresyl phosphate (TCP) is used as a solvent for nitrocellulose esters and numerous natural resins. 
Tricresyl phosphate 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 phosphate is also employed as a hydraulic fluid. When incorporated in gasoline, tricresyl phosphate counteracts the harmful effects of lead deposits. 
In addition, Tricresyl phosphate 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.

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.

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.

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 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 Tricresyl phosphate 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. Its 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.

Tricresyl phosphate, abbreviated TCP, is an organophosphate compound that is used as a plasticizer and diverse other applications. 
Tricresyl phosphate is a colourless, viscous liquid, although commercial samples are typically yellow. 
Tricresyl phosphate is virtually insoluble in water.

Tricresyl phosphates should be stored in a cool, well ventilated area, protected from direct sunlight and away from open flames. 
Containers should be made of galvanized steel; these should be effectively sealed and their contents clearly marked. 

Tricresyl phosphate (TCP) is a non-flammable, viscous clear liquid; insoluble in water, It is stable in neutral and acidic media at normal temperatures. 
But Tricresyl phosphate is readily hydrolysed in an alkaline medium, producing dicresyl phosphate and cresol. 
Commercial Tricresyl phosphate 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.
Esters of phosphoric acid (called organophosphates)  are used in industrial applications as flame-retardants and plasticizers (affording some flame retardancy) in plastics, rubbers and varnishes. 

Organophosphates are the most commonly used flame-retardants in that group. 
Hydraulic fluids and lubricants also contain organophosphates such as tricresyl phosphates, triaryl or trialkyl phosphates to enhance their properties in use. 
Organophosphates are used as defoamers in antifreze solutions, in pulp and paper production and for oil field drilling needs. 
They can be used as antifoam agents in detergent solutions, and in various emulsions, paints, and adhesives. 
Some alkyl phosphates are used as adhesive promoters and for corrosion protection in coatings. 
Phosphoric acid alkyl esters produced generally by the reaction of either alcohols, alcohol ethoxylates or phenyl ethoxylates with polyphosphoric acid or phosphorous pentoxide are anionic surfactants which have the main feature of the stability in alkaline conditions over other surfactants.

They have a wide range of properties including outstanding wetting, emulsification, lubrication, coupling activity and detergency. 
They exhibit the properties of anti-wear and corrosion inhibition either as free esters or in the forms of metal and amine salts.  
They are also used as alkylation agent for nitrogen heterocyclic compounds and as catalysts to produce phenolic and urea resins. 
They are used as solvents in liquid-liquid extractants or separation agent of metals. 
They are is used as heat exchange media and as pigment grinding assistants and antifoam agents.

Synthetic high-temperature lubricating oil consisting of tri-o-cresyl phosphate 2%, tri-m-cresyl phosphate 42%, tri-p-cresyl phosphate 31%, tris(dimethylphenyl) phosphates 18%, tris(ethylphenyl) phosphate 6%, other triaryl phosphates 1%.

IUPAC NAME:

fosforan trójtolilu
 
Reaction mass of tri-o-tolyl phosphate and tri-p-tolyl phosphate and tri-m-tolyl phosphate
 
TRICRESYL PHOSPHATE
 
Tricresyl Phosphate
 
Tricresyl phosphate
 
Tricresyl Phosphate (mixture of isomers)
 
Tricresylphosphate
 
tricresylphosphate
 
Tris(2-methylphenyl) phosphate
 
tris(2-methylphenyl) phosphate
 
tris(2-methylphenyl)phosphate

SYNONYMS:

1330-78-5  
201-105-6  
Phosphate de tris(4-méthylphényle)  
Phosphoric acid, tri-p-tolyl ester (8CI)
Phosphoric acid, tris(4-methylphenyl) ester   
Tricresyl phosphate (Tritolyl phosphate)
TRI-P-CRESYL PHOSPHATE
Tris(4-methylphenyl) phosphate  
Tris(4-methylphenyl)phosphat