Trioctylphosphine oxide

Trioctylphosphine oxide
Names
	Preferred IUPAC name Trioctyl-λ5-phosphanone
	Other names Tri-n-octylphosphine oxide
Identifiers
CAS Number	78-50-2 ;
3D model (JSmol)	Interactive image;
Abbreviations	TOPO
Beilstein Reference	1796648
ChemSpider	59020 ;
ECHA InfoCard	100.001.020
EC Number	201-121-3;
MeSH	Trioctyl+phosphine+oxide
PubChem CID	65577;
RTECS number	SZ1662500;
UNII	EXU8U2AM5A ;
UN number	3077
CompTox Dashboard (EPA)	DTXSID1052537 ;
	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/h4-24H2,1-3H3 Key: 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/h4-24H2,1-3H3 Key: ZMBHCYHQLYEYDV-UHFFFAOYAY;
	SMILES CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC;
Properties
Chemical formula	C24H51OP
Molar mass	386.645 g·mol−1
Appearance	White, opaque crystals
Melting point	50 to 54 °C (122 to 129 °F; 323 to 327 K)
Boiling point	411.2 °C (772.2 °F; 684.3 K) at 760 mmHg
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H315, H318
Precautionary statements	P264, P280, P302+P352, P305+P351+P338, P310, P332+P313, P362
NFPA 704 (fire diamond)	3 1 0
Flash point	110 °C (230 °F; 383 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Trioctylphosphine oxide (TOPO) 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[edit]

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.^[3] The high lipophilicity and high polarity are properties 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.^[4]

In the research laboratory, both trioctylphosphine 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.^[5]

References[edit]

^ Nakhutin, I. E. (1971). Zhurnal Obshchei Khimii. 41 (5): 940–943. {{cite journal}}: Missing or empty |title= (help)
^ "C&L Inventory". echa.europa.eu.
^ Kumar, Jyothi Rajesh; Kim, Joon-Soo; Lee, Jin-Young; Yoon, Ho-Sung (18 February 2011). "A Brief Review on Solvent Extraction of Uranium from Acidic Solutions". Separation & Purification Reviews. 40 (2): 77–125. doi:10.1080/15422119.2010.549760. S2CID 95358600.
^ 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
^ García-Rodríguez, Raúl; Hendricks, Mark P.; Cossairt, Brandi M.; Liu, Haitao; Owen, Jonathan S. (2013). "Conversion Reactions of Cadmium Chalcogenide Nanocrystal Precursors". Chemistry of Materials. 25 (8): 1233–1249. doi:10.1021/cm3035642.

[1] Nakhutin, I. E. (1971). Zhurnal Obshchei Khimii. 41 (5): 940–943. {{cite journal}}: Missing or empty |title= (help)

[2] "C&L Inventory". echa.europa.eu.

[3] Kumar, Jyothi Rajesh; Kim, Joon-Soo; Lee, Jin-Young; Yoon, Ho-Sung (18 February 2011). "A Brief Review on Solvent Extraction of Uranium from Acidic Solutions". Separation & Purification Reviews. 40 (2): 77–125. doi:10.1080/15422119.2010.549760. S2CID 95358600.

[4] 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

[5] García-Rodríguez, Raúl; Hendricks, Mark P.; Cossairt, Brandi M.; Liu, Haitao; Owen, Jonathan S. (2013). "Conversion Reactions of Cadmium Chalcogenide Nanocrystal Precursors". Chemistry of Materials. 25 (8): 1233–1249. doi:10.1021/cm3035642.

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