Tris(chloropropyl) phosphate

Tris(chloropropyl) phosphate (commonly abbreviated TCPP) is a chlorinated organophosphate flame retardant commonly added to polyurethane foams.[1] Comparatively minor amounts are used in PVC and EVA.[2]

Tris(chloropropyl) phosphate
Names
IUPAC name
Tris(2-chloro-1-methylethyl) phosphate
Other names
  • Tris(1-chloro-2-propyl)phosphate
  • Tris(2-chloroisopropyl)phosphate
  • Tris(monochloroisopropyl) phosphate (TMCP)
  • Tris(2-chloroisopropyl) phosphate (TCIP)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.033.766 Edit this at Wikidata
EC Number
  • 237-158-7
UNII
  • InChI=1S/C9H18Cl3O4P/c1-7(4-10)14-17(13,15-8(2)5-11)16-9(3)6-12/h7-9H,4-6H2,1-3H3
    Key: KVMPUXDNESXNOH-UHFFFAOYSA-N
  • O=P(OC(CCl)C)(OC(CCl)C)OC(CCl)C
Properties
C9H18Cl3O4P
Molar mass 327.56 g·mol−1
Appearance Liquid
Melting point 20 °C (68 °F; 293 K)
Boiling point 290 °C (554 °F; 563 K) decomposes
1,080 mg/l at 20°C
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302
P264, P270, P301+P312, P330
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Synthesis

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TCPP is prepared industrially by the reaction of propylene oxide with phosphoryl chloride. In practise this produces a range of products, of which the tris(2-chloro-1-methylethyl) isomer tends to dominate (50-85% w/w).[3]

References

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  1. ^ Yadav, Anilkumar; de Souza, Felipe M.; Dawsey, Tim; Gupta, Ram K. (19 October 2022). "Recent Advancements in Flame-Retardant Polyurethane Foams: A Review". Industrial & Engineering Chemistry Research. 61 (41): 15046–15065. doi:10.1021/acs.iecr.2c02670. S2CID 252832072.
  2. ^ "European Union Risk Assessment Report: TCPP". ECHA. Retrieved 1 March 2024.
  3. ^ Truong, Jimmy W.; Diamond, Miriam L.; Helm, Paul A.; Jantunen, Liisa M. (December 2017). "Isomers of tris(chloropropyl) phosphate (TCPP) in technical mixtures and environmental samples". Analytical and Bioanalytical Chemistry. 409 (30): 6989–6997. doi:10.1007/s00216-017-0572-7. PMID 29147747. S2CID 24611076.