603-35-0
Triphenylphosphine
CAS: 603-35-0
Molecular Formula: C18H15P
603-35-0 - Names and Identifiers
| Name | Triphenylphosphine |
| Synonyms | PPh3 PP-360 trifenylfosfin triarylphosphines Triphenylphosphine triphenylphosphide triphenylphosphane triaryl phosphines PHOSPHORUSTRIPHENYL triphenyl phosphine Trisphenylphosphine Triphenyl phosphine Triphenylphosphorus TRIPHENYL PHOSPHOROUS triphenyl phosphorous LPO Assay Triphenylphosphine |
| CAS | 603-35-0 |
| EINECS | 210-036-0 |
| InChI | InChI=1/C18H15P.BrH/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h1-15H;1H |
| InChIKey | RIOQSEWOXXDEQQ-UHFFFAOYSA-N |
603-35-0 - Physico-chemical Properties
| Molecular Formula | C18H15P |
| Molar Mass | 262.29 |
| Density | 1.132 |
| Melting Point | 79-81°C(lit.) |
| Boling Point | 377°C(lit.) |
| Flash Point | 181 °C |
| Water Solubility | Insoluble |
| Solubility | water: soluble0.00017 g/L at 22°C |
| Vapor Presure | 5 mm Hg ( 20 °C) |
| Vapor Density | 9 (vs air) |
| Appearance | Crystals, Crystalline Powder or Flakes |
| Specific Gravity | 1.132 |
| Color | White |
| Merck | 14,9743 |
| BRN | 610776 |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Incompatible with oxidizing agents, acids. |
| Sensitive | 8: reacts rapidly with moisture, water, protic solvents |
| Refractive Index | 1.6358 |
| Physical and Chemical Properties | Density 1.132 melting point 78.5-81.5°C boiling point 377°C flash point 181°C water-soluble insoluble |
| Use | Used in organic synthesis, also used as polymerization initiator, antibiotic drug clindamycin and other raw materials |
603-35-0 - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R43 - May cause sensitization by skin contact R53 - May cause long-term adverse effects in the aquatic environment R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R48/20/22 - |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | 3077 |
| WGK Germany | 2 |
| RTECS | SZ3500000 |
| FLUKA BRAND F CODES | 9 |
| TSCA | Yes |
| HS Code | 29310095 |
| Toxicity | LD50 orally in Rabbit: 700 mg/kg LD50 dermal Rabbit > 4000 mg/kg |
603-35-0 - Upstream Downstream Industry
| Raw Materials | Phosphorus trichloride |
603-35-0 - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | triphenylphosphine has a molecular formula of C18H15P and a molecular weight of 262.30. It is white to white crystalline powder; soluble in alcohol, benzene and chloroform, insoluble in water; melting point is 78.5~81.5 ℃. Triphenylphosphine is an important ligand for homogeneous catalysts used in petrochemical and fine chemical production, and new uses are constantly being developed, and the demand is increasing year by year. |
| Molecular structure | The triphenylphosphine molecule is a non-centrosymmetric tetrahedral structure, with a pair of lone pairs of electrons The phosphorus atom and the three benzene molecules occupy four vertices respectively, and have a clear tendency to form enantiomeric crystals, triphenylmethane with similar molecular structure has been reported to form orthorhombic crystals with an enantiomeric space group of P212121, while triphenylphosphine has only been found to form a monoclinic structure with a centrosymmetric space group of P21/a. |
| Industrial use | Triphenylphosphine has a wide range of uses in the chemical industry. It is an important fine chemical synthesis catalyst, and it can be better applied through technological improvement New petroleum processing catalysts; new biocatalytic technologies and catalysts; new and high-efficiency catalysts for environmental protection; new catalysts for organic synthesis; new high-efficiency catalysts for polyolefins; new materials for catalyst carriers and various new catalytic materials; it can also be used as functional fine chemicals, new papermaking chemicals; new oilfield chemicals suitable for protective mining and improved oil recovery; new surfactants; High-performance, water-based functional coatings and additives; new textile dyeing and finishing additives; high-performance environmentally friendly adhesives; new safe and environmentally friendly pigments and dyes; high-performance environmentally friendly leather chemicals. Triphenylphosphine can also be used as an intermediate for the synthesis of various important chemical products, such as β-carotene, cefprozil, and cefdinir. |
| application field | triphenylphosphine is a triphenyl substituent of phosphine, which mainly shows reducibility and nucleophilicity. the application fields are as follows: 1. important ligands of homogeneous catalysts used in petrochemical and fine chemical production. 2. The basic raw material of rhodium phosphine complex catalyst. 3. It plays an important role in the reaction of drugs such as vitamin D2, vitamin A, chlorosamycin and plant pigments. 4, the dye industry in the light agent, heat stabilizer, light stabilizer, antioxidant, flame retardant, antistatic agent, rubber anti-ozone agent, analytical reagent. |
| reference quality standard | appearance white crystalline triphenylphosphine content wt%≥ 99.7 triphenylphosphine oxide content wt%≤ 0.3 sulfur (S)PPM <5 chlorine (Cl)PPM <15 sodium (Na)PPM <5 magnesium (Mg)PPM <5 iron (Fe)PPM <10 ash PPM <100 loss on drying <0.5 melting point ≥ 78.5-81.5 solubility dissolved in chloroform, acetic acid and benzene 4% carbon tetrachloride solution light transmittance% ≥ 95 |
| Friedel-Kraffts method | The best reaction conditions are: catalyst dosage 48g, reaction time 8h, reaction temperature 400 ℃, yield 63.5%. Sulfur, phosphorus trichloride and benzene are directly refluxed to form triphenylphosphine compounds, which are then reduced by iron powder to obtain triphenylphosphine. |
| Use | It is used for the synthesis of organophosphorus intermediate trimethyl phosphite by transesterification on pesticides, and then a series of organophosphorus pesticides such as dichlorvos, monocrotophos, and phosphamine can be obtained. In addition, it can be used as a stabilizer for synthetic rubber and resin, an antioxidant for polyvinyl chloride, and a raw material for synthetic alkyd resin and polyester resin. Triphenylphosphine can be used as a raw material for organic synthesis, polymerization initiator, antibiotic drug chlorpyrithromycin, and standard sample for determination of phosphorus by organic microanalysis. It is widely used in medicine, petrochemical, coating, rubber and other industries. It can be used as catalyst, accelerator, inhibitor, photothermal stabilizer, lubricating oil antioxidant, etc. It is also used as a raw material for polymerization initiators, antibiotic drugs chlorectomycin, etc. |
| Production method | Bromobenzene After the format reaction, phosphinization with phosphorus trichloride is used to obtain triphenylphosphine. The preparation method is based on phenol and phosphorus trichloride as raw materials, after esterification reaction and then distillation under reduced pressure to obtain the product triphenyl phosphite. 3C6H5OH PCl3[15~20 ℃]→(C3H5O)3P 3HCl The specific process is divided into batch method and continuous method. (1) Add phenol to the reactor by batch method, add phosphorus trichloride after warm melting, and start reacting with phenol at 70~90 ℃. After adding phosphorus trichloride, the temperature of the reaction mixture will rise to about 150 ℃; Remove dissolved hydrogen chloride and unreacted phenol under reduced pressure at high temperature to obtain the product. (2) A tower reactor is used to allow phenol to enter from under the upper condenser of the tower, and phosphorus trichloride to enter from above the lower receiver of the tower. The two react in the tower, the product is collected in the receiver, and the by-product hydrogen chloride is introduced into the absorption tower through the upper end of the condenser. The crude ester is distilled and other treatments to obtain the product. |
| category | toxic substances |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 700 mg/kg; Oral-mouse LD50: 1000 mg/kg |
| stimulation data | skin-rabbit 500 mg/24 hours severe; Eye-rabbit 500 mg/24 hours mild |
| flammability hazard characteristics | thermal decomposition of toxic phosphides |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from food raw materials storage and transportation |
| fire extinguishing agent | carbon dioxide, sand, water, foam |
| spontaneous combustion temperature | 425°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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