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Trioctylphosphine oxide

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Trioctylphosphine oxide
Structural formula of trioctylphosphine oxide
Names
IUPAC name Trioctyl-λ-phosphanone
Other names Tri-n-octylphosphine oxide
Identifiers
CAS Number
3D model (JSmol)
Abbreviations TOPO
Beilstein Reference 1796648
ChemSpider
ECHA InfoCard 100.001.020 Edit this at Wikidata
EC Number
  • 201-121-3
MeSH Trioctyl+phosphine+oxide
PubChem CID
RTECS number
  • SZ1662500
UN number 3077
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C24H51OP/c1-4-7-10-13-16-19-22-26(25,23-20-17-14-11-8-5-2)24-21-18-15-12-9-6-3/h4-24H2,1-3H3Key: ZMBHCYHQLYEYDV-UHFFFAOYSA-N
  • InChI=1/C24H51OP/c1-4-7-10-13-16-19-22-26(25,23-20-17-14-11-8-5-2)24-21-18-15-12-9-6-3/h4-24H2,1-3H3Key: ZMBHCYHQLYEYDV-UHFFFAOYAY
SMILES
  • CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC
Properties
Chemical formula C24H51OP
Molar mass 386.645 g·mol
Appearance White, opaque crystals
Boiling point 238 °C (460 °F; 511 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3 1 0
Flash point 110 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Trioctylphosphine oxide is an organophosphorus compound with the formula OP(C8H17)3. Frequently referred to as TOPO, this compound is used as an extraction or stabilizing agent. It is an air-stable white solid at room temperature.

Preparation and use

TOPO is usually prepared by oxidation of trioctylphosphine, which in turn is produced by alkylation of phosphorus trichloride.

The main use of TOPO is in solvent extraction of metals, especially uranium. The high lipophilicity and high polarity are propertes key to this application. Its high polarity, which results from the dipolar phosphorus-oxygen bond, allows this compound to bind to metal ions. The octyl groups confer solubility in low polarity solvents such as kerosene.

In the research laboratory, both trioctylphosphane and TOPO are frequently useful as a capping ligand for the production of quantum dots such as those consisting of CdSe. In these cases, TOPO serves as solvent for the synthesis and solubilizes the growing nanoparticles. TOPO-coated quantum dots are typically soluble in chloroform, toluene, and (to a lesser extent) hexane.

References

  1. Watson, E. K.; Rickelton, W. A. "A review of the industrial and recent potential applications of trioctylphosphine oxide" Solvent Extraction and Ion Exchange 1992, volume 10, pp. 879-89. doi:10.1080/07366299208918141
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