Trioctylphosphine oxide

Last updated
Trioctylphosphine oxide
Trioctylphosphine oxide.png
Names
Preferred IUPAC name
Trioctyl-λ5-phosphanone
Other names
Tri-n-octylphosphine oxide
Identifiers
3D model (JSmol)
AbbreviationsTOPO
1796648
ChemSpider
ECHA InfoCard 100.001.020 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-121-3
MeSH Trioctyl+phosphine+oxide
PubChem CID
RTECS number
  • SZ1662500
UNII
UN number 3077
  • 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 Yes check.svgY
    Key: ZMBHCYHQLYEYDV-UHFFFAOYSA-N Yes check.svgY
  • 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
  • CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC
Properties
C24H51OP
Molar mass 386.645 g·mol−1
AppearanceWhite, 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 [1]
Hazards [2]
GHS labelling:
GHS-pictogram-acid.svg
Danger
H315, H318
P264, P280, P302+P352, P305+P351+P338, P310, P332+P313, P362
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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 (230 °F; 383 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. It is lipophilic, and like other phosphine oxides serves as a Lewis base owing to a partial negative charge at the O atom.

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. [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]

Related Research Articles

The actinide or actinoid series encompasses at least the 14 metallic chemical elements in the 5f series, with atomic numbers from 89 to 102, actinium through nobelium. The actinide series derives its name from the first element in the series, actinium. The informal chemical symbol An is used in general discussions of actinide chemistry to refer to any actinide.

<span class="mw-page-title-main">Solubility</span> Capacity of a substance to dissolve in a homogeneous way

In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution.

Extractive metallurgy is a branch of metallurgical engineering wherein process and methods of extraction of metals from their natural mineral deposits are studied. The field is a materials science, covering all aspects of the types of ore, washing, concentration, separation, chemical processes and extraction of pure metal and their alloying to suit various applications, sometimes for direct use as a finished product, but more often in a form that requires further working to achieve the given properties to suit the applications.

<span class="mw-page-title-main">Nuclear reprocessing</span> Chemical operations that separate fissile material from spent fuel to be recycled as new fuel

Nuclear reprocessing is the chemical separation of fission products and actinides from spent nuclear fuel. Originally, reprocessing was used solely to extract plutonium for producing nuclear weapons. With commercialization of nuclear power, the reprocessed plutonium was recycled back into MOX nuclear fuel for thermal reactors. The reprocessed uranium, also known as the spent fuel material, can in principle also be re-used as fuel, but that is only economical when uranium supply is low and prices are high. Nuclear reprocessing may extend beyond fuel and include the reprocessing of other nuclear reactor material, such as Zircaloy cladding.

Hydrometallurgy is a technique within the field of extractive metallurgy, the obtaining of metals from their ores. Hydrometallurgy involve the use of aqueous solutions for the recovery of metals from ores, concentrates, and recycled or residual materials. Processing techniques that complement hydrometallurgy are pyrometallurgy, vapour metallurgy, and molten salt electrometallurgy. Hydrometallurgy is typically divided into three general areas:

<span class="mw-page-title-main">Phosphorus trichloride</span> Chemical compound

Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.

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.

<span class="mw-page-title-main">Cryptand</span> Cyclic, multidentate ligands adept at encapsulating cations

In chemistry, cryptands are a family of synthetic, bicyclic and polycyclic, multidentate ligands for a variety of cations. The Nobel Prize for Chemistry in 1987 was given to Donald J. Cram, Jean-Marie Lehn, and Charles J. Pedersen for their efforts in discovering and determining uses of cryptands and crown ethers, thus launching the now flourishing field of supramolecular chemistry. The term cryptand implies that this ligand binds substrates in a crypt, interring the guest as in a burial. These molecules are three-dimensional analogues of crown ethers but are more selective and strong as complexes for the guest ions. The resulting complexes are lipophilic.

<span class="mw-page-title-main">Cadmium selenide</span> Chemical compound

Cadmium selenide is an inorganic compound with the formula CdSe. It is a black to red-black solid that is classified as a II-VI semiconductor of the n-type. It is a pigment, but applications are declining because of environmental concerns.

<span class="mw-page-title-main">Methyl isobutyl ketone</span> Chemical compound

Methyl isobutyl ketone (MIBK, 4-methylpentan-2-one) is an organic compound with the condensed chemical formula (CH3)2CHCH2C(O)CH3. This ketone is a colourless liquid that is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.

<span class="mw-page-title-main">Liquid–liquid extraction</span> Method to separate compounds or metal complexes

Liquid–liquid extraction, also known as solvent extraction and partitioning, is a method to separate compounds or metal complexes, based on their relative solubilities in two different immiscible liquids, usually water (polar) and an organic solvent (non-polar). There is a net transfer of one or more species from one liquid into another liquid phase, generally from aqueous to organic. The transfer is driven by chemical potential, i.e. once the transfer is complete, the overall system of chemical components that make up the solutes and the solvents are in a more stable configuration. The solvent that is enriched in solute(s) is called extract. The feed solution that is depleted in solute(s) is called the raffinate. Liquid–liquid extraction is a basic technique in chemical laboratories, where it is performed using a variety of apparatus, from separatory funnels to countercurrent distribution equipment called as mixer settlers. This type of process is commonly performed after a chemical reaction as part of the work-up, often including an acidic work-up.

<span class="mw-page-title-main">Uranyl nitrate</span> Chemical compound

Uranyl nitrate is a water-soluble yellow uranium salt with the formula UO2(NO3)2 · n H2O. The hexa-, tri-, and dihydrates are known. The compound is mainly of interest because it is an intermediate in the preparation of nuclear fuels. In the nuclear industry, it is commonly referred to as yellow salt.

The uranyl ion is an oxycation of uranium in the oxidation state +6, with the chemical formula UO2+
2
. It has a linear structure with short U–O bonds, indicative of the presence of multiple bonds between uranium and oxygen. Four or more ligands may be bound to the uranyl ion in an equatorial plane around the uranium atom. The uranyl ion forms many complexes, particularly with ligands that have oxygen donor atoms. Complexes of the uranyl ion are important in the extraction of uranium from its ores and in nuclear fuel reprocessing.

<span class="mw-page-title-main">Hexafluorophosphate</span> Anion with the chemical formula PF6–

Hexafluorophosphate is an anion with chemical formula of [PF6]. It is an octahedral species that imparts no color to its salts. [PF6] is isoelectronic with sulfur hexafluoride, SF6, and the hexafluorosilicate dianion, [SiF6]2−, and hexafluoroantimonate [SbF6]. In this anion, phosphorus has a valence of 5. Being poorly nucleophilic, hexafluorophosphate is classified as a non-coordinating anion.

Acid–base extraction is a subclass of liquid–liquid extractions and involves the separation of chemical species from other acidic or basic compounds. It is typically performed during the work-up step following a chemical synthesis to purify crude compounds and results in the product being largely free of acidic or basic impurities. A separatory funnel is commonly used to perform an acid-base extraction.

<span class="mw-page-title-main">Superheated water</span> Pressurized liquid water at temperatures between the boiling and critical points

Superheated water is liquid water under pressure at temperatures between the usual boiling point, 100 °C (212 °F) and the critical temperature, 374 °C (705 °F). It is also known as "subcritical water" or "pressurized hot water". Superheated water is stable because of overpressure that raises the boiling point, or by heating it in a sealed vessel with a headspace, where the liquid water is in equilibrium with vapour at the saturated vapor pressure. This is distinct from the use of the term superheating to refer to water at atmospheric pressure above its normal boiling point, which has not boiled due to a lack of nucleation sites.

<span class="mw-page-title-main">Di(2-ethylhexyl)phosphoric acid</span> Chemical compound

Di(2-ethylhexyl)phosphoric acid (DEHPA or HDEHP) is an organophosphorus compound with the formula (C8H17O)2PO2H. The colorless liquid is a diester of phosphoric acid and 2-ethylhexanol. It is used in the solvent extraction of uranium, vanadium and the rare-earth metals.

<span class="mw-page-title-main">Actinide chemistry</span> Branch of nuclear chemistry

Actinide chemistry is one of the main branches of nuclear chemistry that investigates the processes and molecular systems of the actinides. The actinides derive their name from the group 3 element actinium. The informal chemical symbol An is used in general discussions of actinide chemistry to refer to any actinide. All but one of the actinides are f-block elements, corresponding to the filling of the 5f electron shell; lawrencium, a d-block element, is also generally considered an actinide. In comparison with the lanthanides, also mostly f-block elements, the actinides show much more variable valence. The actinide series encompasses the 15 metallic chemical elements with atomic numbers from 89 to 103, actinium through lawrencium.

The advanced reprocessing of spent nuclear fuel is a potential key to achieve a sustainable nuclear fuel cycle and to tackle the heavy burden of nuclear waste management. In particular, the development of such advanced reprocessing systems may save natural resources, reduce waste inventory and enhance the public acceptance of nuclear energy. This strategy relies on the recycling of major actinides and the transmutation of minor actinides in appropriate reactors. In order to fulfill this objective, selective extracting agents need to be designed and developed by investigating their complexation mechanism.

<span class="mw-page-title-main">Trioctylphosphine selenide</span> Chemical compound

Trioctylphosphine selenide(TOPSe) is an organophosphorus compound with the formula SeP(C8H17)3. It is used as a source of selenium in the preparation of cadmium selenide. TOPSe is a white, air-stable solid that is soluble in organic solvents. The molecule features a tetrahedral phosphorus center.

References

  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.