Trixylyl phosphate

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Trixylyl phosphate
Names
Other names
  • tris(dimethylphenyl) phosphate
  • Tri-dimethyl phenyl phosphate
  • Tri-xylenyl phosphate
Identifiers
ECHA InfoCard 100.042.419 Edit this at Wikidata
EC Number
  • 246-677-8
Properties
C24H27O4P
Molar mass 410.450 g·mol−1
Appearance Viscous liquid
Density 1.142
Melting point −20 °C (−4 °F; 253 K)
Boiling point 394 °C (741 °F; 667 K)
20 µg/L
Hazards
GHS labelling:
GHS08: Health hazard
Danger
H360F
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Trixylyl phosphate (TXP) is an aromatic phosphate ester. It was historically used as a flame retardant for acetate plastics (cellulose nitrate and cellulose acetate) and PVC. It also saw significant use as a fire-resistant hydraulic fluid.

Trixylyl phosphate is now banned or restricted in several jurisdictions, due to its poor safety profile. Short term exposure can cause organophosphate-induced delayed neuropathy,[1] but it is also regarded as a reproductive toxin. In the EU is classified as a substance of very high concern, requiring authorisation to be used.

Synthesis

Trixylyl phosphate is prepared industrially by the reaction of phosphoryl chloride with mixed xylenols. In practise this produces a range of products.

References

  1. ^ Mortensen, A; Ladefoged, O (1992). "Delayed neurotoxicity of trixylenyl phosphate and a trialkyl/aryl phosphate mixture, and the modulating effect of atropine on tri-o-tolyl phosphate-induced neurotoxicity". Neurotoxicology. 13 (2): 347–54. PMID 1436754.


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