Tricresyl phosphate
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| Names | |
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| Other names
tricresylphosphate, tri-o-cresyl phosphate, TOCP, tritolyl phosphate, tolyl phosphate, tri-o-tolyl ester of phosphoric acid
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| Identifiers | |
3D model (JSmol)
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| ECHA InfoCard | 100.014.136 |
CompTox Dashboard (EPA)
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| Properties | |
| C21H21O4P | |
| Molar mass | 368.37 g/mole |
| Melting point | -40 °C |
| Boiling point | 240-255 °C |
| Hazards | |
| Flash point | > 225 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 , the p- isomer is , and the o- isomer is .
Production
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
Uses
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.[1] 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.[2] As a gasoline additive, it also helps preventing engine misfires.[3]
Safety
TCP is a known neurotoxin[4] 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.[3]
Aircraft
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.[5][6]
References
- ^ Marvel & other solutions to the lead problem, checked 2009-06-18.
- ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1016/j.chroma.2007.05.087, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
|doi=10.1016/j.chroma.2007.05.087instead. - ^ a b 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
- ^ Lack of Delayed Neurotoxic Effect after Tri-o-cresyl Phosphate Treatment in Male Fischer 344 Rats: Biochemical, Neurobehavioral and Neuropathological Studies
- ^ 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