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| | Trioctylphosphine oxide Basic information |
| | Trioctylphosphine oxide Chemical Properties |
| Melting point | 50-52 °C(lit.) | | Boiling point | 201-202 °C2 mm Hg(lit.) | | density | 0,88 g/cm3 | | vapor pressure | 0.004Pa at 50℃ | | Fp | >230 °F | | storage temp. | Store below +30°C. | | solubility | <1g/l | | form | Crystalline Powder, Crystals or Flakes | | color | White to slightly yellow | | Water Solubility | Insoluble | | BRN | 1796648 | | Henry's Law Constant | 8.2×10-4 mol/(m3Pa) at 25℃, Zhang et al. (2010) | | Stability: | Stable. Incompatible with strong oxidizing agents. | | 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 | | InChIKey | ZMBHCYHQLYEYDV-UHFFFAOYSA-N | | SMILES | CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC | | LogP | 9.54 | | CAS DataBase Reference | 78-50-2(CAS DataBase Reference) | | EPA Substance Registry System | Phosphine oxide, trioctyl- (78-50-2) |
| Hazard Codes | Xi,Hazard | | Risk Statements | 38-41-50/53-34 | | Safety Statements | 26-36/39-39-61-60-45-36/37/39 | | RIDADR | 3261 | | WGK Germany | 2 | | RTECS | SZ1662500 | | Autoignition Temperature | 270 °C | | TSCA | TSCA listed | | PackingGroup | II | | HS Code | 29310095 | | HS Code | 32019090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Aquatic Chronic 3
Eye Dam. 1
Skin Irrit. 2 | | Toxicity | LD50 orally in Rabbit: > 10000 mg/kg LD50 dermal Rat 2830 mg/kg |
| | Trioctylphosphine oxide Usage And Synthesis |
| Chemical Properties | white crystalline powder | | Uses | Tri-n-octylphosphine oxide is a solvent used in the extraction of metals, especially uranium, zirconium and hafnium. It is also used as an auxiliary reagent in the solvent extraction of metals. It is also used to extract hydrogen bonding organic compounds. Further, it is useful as a capping ligand for the production of quantum dots, such as those consisting of cadmium selenide. | | Uses | Catalyst in:
- Preparation of tetradentate planar-chiral hydroxy-substituted ferrocenecarboxaldimine Schiff base ligands
- Reactions of allyl esters with hydrosilanes
- Asymmetric cyanosilylation of aldehydes
- Preparation of chlorothiol formates from thiols and phosgene
| | Uses | Trioctylphosphine oxide (TOPO) is most commonly used as the solvent due to its high boiling point and chemical stability, and its ability to prevent particle aggregation via coordination to the NP surface. trioctylphosphine oxide is a frequently used surfactant, starts to decompose at around 425℃.
| | Application | The industrial applications of trioctylphosphine oxide, make use of its complexing powers with metals and with hydrogen donor organic compounds. Commercial uses as a solvent extraction reagent are in the recovery of uranium from wet process phosphoric acid and in the recovery of byproduct acetic acid and furfural generated during sulphite wood pulping. | | Production Methods | method 1: preparing trioctylphosphine oxide from sodium hypophosphite by performing octene addition, trichlorosilane reduction, bromoalkane addition and hydrolysis in turn;
method 2: preparing the trioctylphosphine oxide from the sodium hypophosphite by performing the octene addition, the trichlorosilane reduction, the hydrolysis and the octene addition again in turn;
method 3: preparing the trioctylphosphine oxide from the sodium hypophosphite by performing the octene addition, the trichlorosilane reduction and alcoholysis in turn. | | General Description | Visit our Sensor Applications portal to learn more. | | Flammability and Explosibility | Non flammable | | reaction suitability | reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand | | Purification Methods | Mason, McCarty and Peppard [J Inorg Nuclear Chem 24 967 1962] stirred a 0.1M solution in *benzene with an equal volume of 6M HCl at 40o in a sealed flask for 48hours, then washed the *benzene solution successively with water (twice), 5% aqueous Na2CO3 (three times) and water (six times). The *benzene and water were then evaporated under reduced pressure at room temperature. Zingaro and White [J Inorg Nucl Chem 12 315 1960] treated a pet ether solution with aqueous KMnO4 (to oxidise any phosphinous acids to phosphinic acids), then with sodium oxalate, H2SO4 and HCl (to remove any manganese compounds). The pet ether solution was slurried with activated alumina (to remove phosphinic acids), filtered, evaporated and the residue was recrystallised from pet ether or cyclohexane at -20o. It can also be recrystallised from EtOH. [Beilstein 4 IV 3466.] |
| | Trioctylphosphine oxide Preparation Products And Raw materials |
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