Tris(2-chloroethyl) phosphate

Last updated
Tris(2-chloroethyl) phosphate
Tris(2-chloroethyl) phosphate.svg
Names
Preferred IUPAC name
Tris(2-chloroethyl) phosphate
Other names
2-Chloroethanol phosphate; Tris(β-chloroethyl) phosphate; Tri(2-chloroethyl) phosphate; Tris(2-chloroethyl) orthophosphate; TCEP
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.744 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H12Cl3O4P/c7-1-4-11-14(10,12-5-2-8)13-6-3-9/h1-6H2
    Key: HQUQLFOMPYWACS-UHFFFAOYSA-N
  • InChI=1/C6H12Cl3O4P/c7-1-4-11-14(10,12-5-2-8)13-6-3-9/h1-6H2
    Key: HQUQLFOMPYWACS-UHFFFAOYAR
  • ClCCOP(=O)(OCCCl)OCCCl
Properties
C6H12Cl3O4P
Molar mass 285.48 g·mol−1
Density 1.39 g/mL [1]
Boiling point 192 °C (378 °F; 465 K) 10 mmHg [1]
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H302, H351, H360, H411
P201, P202, P270, P273, P301+P312, P308+P313, P391
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tris(2-chloroethyl) phosphate (TCEP) is a chemical compound used as a flame retardant, plasticizer, and viscosity regulator in various types of polymers including polyurethanes, polyester resins, and polyacrylates. [2]

Contents

Safety

Because of its suspected reproductive toxicity, it is listed as a substance of very high concern under the European Union's REACH regulations. Its use has been largely replaced by tris(chloropropyl) phosphate, which is safer. [3]

See also

Related Research Articles

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<span class="mw-page-title-main">Organophosphate</span> Organic compounds with the structure O=P(OR)3

In organic chemistry, organophosphates are a class of organophosphorus compounds with the general structure O=P(OR)3, a central phosphate molecule with alkyl or aromatic substituents. They can be considered as esters of phosphoric acid.

Tributyl phosphate, known commonly as TBP, is an organophosphorus compound with the chemical formula (CH3CH2CH2CH2O)3PO. This colourless, odorless liquid finds some applications as an extractant and a plasticizer. It is an ester of phosphoric acid with n-butanol.

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A fire retardant is a substance that is used to slow down or stop the spread of fire or reduce its intensity. This is commonly accomplished by chemical reactions that reduce the flammability of fuels or delay their combustion. Fire retardants may also cool the fuel through physical action or endothermic chemical reactions. Fire retardants are available as powder, to be mixed with water, as fire-fighting foams and fire-retardant gels. Fire retardants are also available as coatings or sprays to be applied to an object.

Tris may refer to:

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Tricresyl phosphate (TCP), is a mixture of three isomeric organophosphate compounds most notably used as a flame retardant. Other uses include as a plasticizer in manufacturing for lacquers and varnishes and vinyl plastics and as an antiwear additive in lubricants. Pure tricresyl phosphate is a colourless, viscous liquid, although commercial samples are typically yellow. It is virtually insoluble in water, but easily soluble in organic solvents like toluene, hexane, and diethylether among others. It was synthesized by Alexander Williamson in 1854 upon reacting phosphorus pentachloride with cresol, though today's manufacturers can prepare TCP by mixing cresol with phosphorus oxychloride or phosphoric acid as well. TCP, 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 outside of laboratory studies that require isomeric purity, due to its extremely toxic nature, and is generally excluded from commercial products where TCP is involved.

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Triphenyl phosphate (TPhP) is the chemical compound with the formula OP(OC6H5)3. It is the simplest aromatic organophosphate. This colourless solid is the ester (triester) of phosphoric acid and phenol. It is used as a plasticizer and a fire retardant in a wide variety of settings and products.

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<span class="mw-page-title-main">Tris(1,3-dichloro-2-propyl)phosphate</span> Chemical compound

Tris(1,3-dichloroisopropyl)phosphate (TDCPP) is a chlorinated organophosphate. Organophosphate chemicals have a wide variety of applications and are used as flame retardants, pesticides, plasticizers, and nerve gases. TDCPP is structurally similar to several other organophosphate flame retardants, such as tris(2-chloroethyl) phosphate (TCEP) and tris(chloropropyl)phosphate (TCPP). TDCPP and these other chlorinated organophosphate flame retardants are all sometimes referred to as "chlorinated tris".

<span class="mw-page-title-main">Tris(2,3-dibromopropyl) phosphate</span> Chemical compound

Tris(2,3-dibromopropyl) phosphate ("tris") is a chemical once widely used as a flame retardant in plastics and textiles.

<span class="mw-page-title-main">Aluminium diethyl phosphinate</span> Chemical compound

Aluminium diethyl phosphinate is a chemical compound with formula Al(C
4
H
10
O
2
P
)3. It decomposes above 300 °C.

Silent Spring Institute is a nonprofit organization dedicated to studying and reporting primarily on breast cancer prevention, although its research covers other health-related topics as well.

<span class="mw-page-title-main">Tris(2-ethylhexyl) phosphate</span> Chemical compound

Tris(2-ethylhexyl)phosphate (TEHP) is an organic chemical compound in the organophosphate group. It is a triakylphosphate.

<span class="mw-page-title-main">Tris(chloropropyl) phosphate</span> Chemical compound

Tris(chloropropyl) phosphate is a chlorinated organophosphate flame retardant commonly added to polyurethane foams. Comparatively minor amounts are used in PVC and EVA.

References

  1. 1 2 "Tris(2-chloroethyl) phosphate". Sigma-Aldrich . Retrieved February 25, 2013.
  2. Opinion on tris(2-chloroethyl)phosphate (TCEP) in Toys (PDF) (Report). European Commission, Scientific Committee on Health and Environmental Risks. 22 March 2012. Retrieved February 25, 2013.
  3. Krivoshiev, Boris V.; Beemster, Gerrit T.S.; Sprangers, Katrien; Blust, Ronny; Husson, Steven J. (April 2018). "A toxicogenomics approach to screen chlorinated flame retardants tris(2-chloroethyl) phosphate and tris(2-chloroisopropyl) phosphate for potential health effects". Journal of Applied Toxicology. 38 (4): 459–470. doi:10.1002/jat.3553. PMID   29143341. S2CID   3320347.