Tricresyl phosphate

Tricresyl phosphate

Chembox new
ImageFile = Tricresyl_phosphate.png ImageSize = 250px
OtherNames = tricresylphosphate, tri-o-cresyl phosphate, TOCP, tritolyl phosphate, tolyl phosphate, tri-o-tolyl ester of phosphoric acid
Section1 = Chembox Identifiers
CASNo = 1330-78-5
PubChem =
SMILES = O=P(Oc2ccccc2C)(Oc3ccccc3C)Oc1ccccc1C

Section2 = Chembox Properties
Formula = C21H21O4P
MolarMass = 368.37 g/mole
Appearance =
Density =
MeltingPt = -40 °C
BoilingPt = 240-255 °C
Solubility =

Section3 = Chembox Hazards
MainHazards =
FlashPt = > 225 °C
Autoignition =

Tricresyl phosphate, abbreviated TCP, is an organophosphate compound. It is a derived from cresol and phosphoric acid. This viscous liquid is colourless when pure, but commercial samples are typically yellow. It is nonflammable and virtually insoluble in water. Commercial tricresyl phosphate is a mixture of ortho, meta, and para-cresyl phosphates , the m- isomer is CASREF|CAS=563-04-2, the p- isomer is CASREF|CAS=78-32-0, and the o- isomer is CASREF|CAS=78-30-8.


Tricresyl phosphate is manufactured by reaction of cresols with phosphorus oxychloride::OPCl3 + 3 HOC6H4CH3 → OP(OC6H4CH3)3 + 3 HClIn alkaline medium it undergoes hydrolysis to cresol and dicresyl phosphate.:OP(OC6H4CH3)3 + NaOH → + HOC6H4CH3 + NaO2P(OC6H4CH3)2


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 tetra-ethyl lead. It is a hydraulic fluid and a heat exchange medium. Exploiting its hydrophobic properties, it is used in waterproofing of materials. It is a solvent for extractions, a solvent for nitrocellulose and other polymers. It is also used as an AW additive and EP additive in lubricants, and in hydraulic fluids [ [ Determination of airborne trialkyl and triaryl organophosphates originating from hydraulic fluids by gas chromatography–mass spectrometry Development of methodology for combined aerosol and vapor sampling] ] . As a gasoline additive, it also helps preventing engine misfires.Jürgen Svara1, Norbert Weferling2, Thomas Hofmann "Phosphorus Compounds, Organic" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH: Wienheim. DOI: 10.1002/14356007.a19_545.pub2. Article Online Posting Date: December 15, 2006]


TCP is a known neurotoxin [ [ Lack of Delayed Neurotoxic Effect after Tri-o-cresyl Phosphate Treatment in Male Fischer 344 Rats: Biochemical, Neurobehavioral and Neuropathological Studies] ] and is of “toxicological importance” and has been responsible for many deaths. The most serious incident arose in the 1920s when TCP was used as an adulterant for Jamaican ginger.


TCP is found in the engine oil of commercial jet airliners. It has been suggested that it can contaminate the cabin air through the engine bleed air system, and could therefore cause negative health effects in crew and passengers. Tests have found raised levels of TCP in some airline cabins, although the link between cabin TCP contamination and ill health, or conditions such as Jet lag, has yet to be proved, although has been suggested. [ [ Do you know what you're breathing at 30,000 feet?] , Date = 25-2-2008, Author = Chris Ingalls, Access date = 3-12-2008] [ [ The Toxic Free Airlines website] , Date = unknown, Author = unknown, Access date = 3-12-2008]


Wikimedia Foundation. 2010.

Игры ⚽ Поможем сделать НИР

Look at other dictionaries:

  • tricresyl phosphate — noun : 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 …   Useful english dictionary

  • tricresyl phosphate — tri·cres·yl phos·phate (tri kresґəl) tritolyl phosphate …   Medical dictionary

  • tricresyl phosphate — noun An organophosphate compound derived from cresol and phosphoric acid, chemical formula CHOP, used as a plasticizer, flame retardant, waterproofer, etc …   Wiktionary

  • tritolyl phosphate — tri·tol·yl phos·phate (tri tolґəl) a mixture of isomers prepared from creosote and other organic compounds; used as a flame retardant, in the manufacture of vinyl plastics, and for other industrial purposes. One of the isomers, tri o tolyl… …   Medical dictionary

  • tritolyl phosphate — noun : tricresyl phosphate …   Useful english dictionary

  • Phosphoryl chloride — Phosphoryl chloride …   Wikipedia

  • Munisport — Landfill Superfund site Geography City North Miami County Miami Dade County State Florida …   Wikipedia

  • Plasticizer — Plasticizers are additives that increase the plasticity or fluidity of the material to which they are added, these include plastics, cement, concrete, wallboard and clay bodies. Although the same compounds are often used for both plastics and… …   Wikipedia

  • Phosphorus trichloride — Phosphorus trichloride …   Wikipedia

  • AW additive — AW additives, or antiwear additives, are additives for lubricants to prevent metal to metal contact between parts of gears.EP additives are usually used in applications such as gearboxes, while AW additives are used with lighter loads such as… …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”