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9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide

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9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide
Names
Other names 3,4:5,6-Dibenzo-2H-1,2-oxaphosphorin-2-oxide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
EC Number
  • 252-813-7
PubChem CID
UNII
InChI
  • InChI=1S/C12H9O2P/c13-15-12-8-4-2-6-10(12)9-5-1-3-7-11(9)14-15/h1-8,15HKey: VBQRUYIOTHNGOP-UHFFFAOYSA-N
  • 9,10-Dihydro-9-oxa-10-phosphaphenanthrene: InChI=1S/C12H9OP/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)14-13-11/h1-8,14HKey: HDXGUOZQUVDYMC-UHFFFAOYSA-N
SMILES
  • C1=CC=C2C(=C1)C3=CC=CC=C3P(=O)O2
Properties
Chemical formula C12H9O2P
Molar mass 216.176 g·mol
Appearance white solid
Melting point 119–121 °C (246–250 °F; 392–394 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) is an organophosphorus compound that is used to produce fire retardants. From the chemistry perspective, it is a derivative of hypophosphorous acid as well as a derivative of phenanthrene. The reactivity of the P-H center allows for the conjugation of DOPO to many monomers. Such monomers are incorporated into polymers, conferring fire retardant properties. It is mainly used for nylon and polyesters, as well as epoxides.

The compound is prepared from 2-phenylphenol, which condenses with one equivalent of phosphorus trichloride. Heating that species in the presence of aluminium trichloride results in cyclization. The procedure is completed by hydrolysis.

References

  1. Qian, Xiaodong; Song, Lei; Jiang, Saihua; Tang, Gang; Xing, Weiyi; Wang, Bibo; Hu, Yuan; Yuen, Richard K. K. (2013). "Novel Flame Retardants Containing 9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide and Unsaturated Bonds: Synthesis, Characterization, and Application in the Flame Retardancy of Epoxy Acrylates". Industrial & Engineering Chemistry Research. 52 (22): 7307–7315. doi:10.1021/ie400872q.
  2. Levchik, Sergei V.; Weil, Edward D. (2006). "A Review of Recent Progress in Phosphorus-based Flame Retardants". Journal of Fire Sciences. 24 (5): 345–364. doi:10.1177/0734904106068426.
  3. Beard, Adrian; Battenberg, Christian; Sutker, Burton J. (2021). "Flame Retardants". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_123.pub2. ISBN 978-3-527-30385-4. S2CID 261178139.
  4. Salmeia, Khalifah A.; Gaan, Sabyasachi (2015). "An overview of some recent advances in DOPO-derivatives: Chemistry and Flame Retardant Applications". Polymer Degradation and Stability. 113: 119–134. doi:10.1016/j.polymdegradstab.2014.12.014.
  5. Chernyshev, E. A.; Aksenov, V. I.; Ponomarev, V. V.; Golubtsov, S. A.; Bugerenko, E. F. (1972). "Synthesis and reactions of 10-chloro-9,10-dihydro-10-phospha-9-oxaphenanthrene oxaphosphorin]". Zhurnal Obshchei Khimii. 42: 93-6.
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