Tricresyl phosphate

Tricresyl phosphate

Names
Other names tricresylphosphate, tri-o-cresyl phosphate, TOCP, tritolyl phosphate, tolyl phosphate, tri-o-tolyl ester of phosphoric acid
Identifiers
CAS Number	1330-78-5 Y
3D model (Jmol)	Interactive image
ChemSpider	21106216 Y
ECHA InfoCard	100.014.136
InChI InChI=1S/C21H21O4P/c1-16-10-4-7-13-19(16)23-26(22,24-20-14-8-5-11-17(20)2)25-21-15-9-6-12-18(21)3/h4-15H,1-3H3 Y Key: YSMRWXYRXBRSND-UHFFFAOYSA-N Y InChI=1/C21H21O4P/c1-16-10-4-7-13-19(16)23-26(22,24-20-14-8-5-11-17(20)2)25-21-15-9-6-12-18(21)3/h4-15H,1-3H3 Key: YSMRWXYRXBRSND-UHFFFAOYAP
SMILES Cc3ccccc3OP(=O)(Oc1ccccc1C)Oc2ccccc2C
Properties
Chemical formula	C21H21O4P
Molar mass	368.37 g/mole
Appearance	colourless liquid
Melting point	−40 °C (−40 °F; 233 K)
Boiling point	255 °C (491 °F; 528 K) (10 mmHg)
Hazards
Flash point	> 225 °C (437 °F; 498 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

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

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

The cresol is a mixture of three isomers (ortho, meta, and para). 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.

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

In the body, it is metabolized in part by hydroxylation to give a catecholate derivative, which is the bio-active agent responsible for its neurotoxicity.

Tricresyl phosphate is used as a plasticizer in nitrocellulose, acrylate lacquers, varnishes, and in polyvinyl chloride. It is a flame retardant in plastics and rubbers. It is used as a gasoline additive as a lead scavenger for tetraethyllead. It is a hydraulic fluid and a heat exchange medium. It is also used by the U.S. Navy in its pure form as a lubricant in cryogenic liquid pumps. Exploiting its hydrophobic properties, it is used for the waterproofing of materials. It is a solvent for extractions, a solvent for nitrocellulose and other polymers. It is used as an antiwear and extreme pressure additive in lubricants and hydraulic fluids.