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        Triphenylphosphine

        description Chemical properties Name Reactions Friedel-krogh`s method Uses Production methods Hazards & Safety Information
        Triphenylphosphine
        Triphenylphosphine structure
        CAS No.
        603-35-0
        Chemical Name:
        Triphenylphosphine
        Synonyms
        PPh3;PP-360;Triphenyl;'LGC' (4006);Trifenylfosfin;Trihenylphosphine;Triphenyphosphine;Triphenylphosphane;Triphenylphosphide;triphenyl-phosphin
        CBNumber:
        CB8771461
        Molecular Formula:
        C18H15P
        Formula Weight:
        262.29
        MOL File:
        603-35-0.mol

        Triphenylphosphine Properties

        Melting point:
        79-81 °C(lit.)
        Boiling point:
        377 °C(lit.)
        Density 
        1.132
        vapor density 
        9 (vs air)
        vapor pressure 
        5 mm Hg ( 20 °C)
        refractive index 
        1.6358
        Flash point:
        181 °C
        storage temp. 
        Store at RT.
        solubility 
        water: soluble0.00017 g/L at 22°C
        form 
        Crystals, Crystalline Powder or Flakes
        color 
        White
        Specific Gravity
        1.132
        Water Solubility 
        Insoluble
        Merck 
        14,9743
        BRN 
        610776
        Stability:
        Stable. Incompatible with oxidizing agents, acids.
        InChIKey
        RIOQSEWOXXDEQQ-UHFFFAOYSA-N
        CAS DataBase Reference
        603-35-0(CAS DataBase Reference)
        NIST Chemistry Reference
        Phosphine, triphenyl-(603-35-0)
        EPA Substance Registry System
        Triphenylphosphine (603-35-0)
        SAFETY
        • Risk and Safety Statements
        Symbol(GHS) 
        GHS07,GHS08
        Signal word  Warning
        Hazard statements  H302-H317-H373
        Precautionary statements  P260-P280g-P301+P312a-P321-P501a-P280-P301+P312+P330-P333+P313
        Hazard Codes  Xn,N
        Risk Statements  22-43-53-50/53-48/20/22
        Safety Statements  36/37-60-61-36/37/39-26
        RIDADR  3077
        WGK Germany  2
        RTECS  SZ3500000
        9
        Autoignition Temperature 425 °C
        TSCA  Yes
        HS Code  29310095
        Toxicity LD50 orally in Rabbit: 700 mg/kg LD50 dermal Rabbit > 4000 mg/kg
        NFPA 704
        1
        2 0

        Triphenylphosphine price More Price(27)

        Manufacturer Product number Product description CAS number Packaging Price Updated Buy
        Sigma-Aldrich T84409 Triphenylphosphine ReagentPlus , 99% 603-35-0 1g $22.4 2019-12-02 Buy
        Sigma-Aldrich T84409 Triphenylphosphine ReagentPlus , 99% 603-35-0 1kg $171 2019-12-02 Buy
        TCI Chemical T0519 Triphenylphosphine >95.0%(T) 603-35-0 25g $19 2019-12-02 Buy
        TCI Chemical T0519 Triphenylphosphine >95.0%(T) 603-35-0 100g $41 2019-12-02 Buy
        Alfa Aesar 014112 Triphenylphosphine 99+% 603-35-0 25g $20.9 2019-12-02 Buy

        Triphenylphosphine Chemical Properties,Uses,Production

        description

        Triphenylphosphine (TPP) is used in the synthesis of organic compounds due to its nucleophilicity and its reducing character. TPP is a highly efficient product that serves successfully in many applications, for example:
        1. The important ligands of homogeneous catalysts used in petrochemicals and fine chemicals production, as a co-catalyst in isobutanol and n-butanol production.
        2. The basic raw material of rhodium phosphine complex catalyst, It is used to prepare Wilkinson's catalyst, RhCl(PPh3)3 useful to catalyze the hydrogenation of alkenes and tetrakis(triphenylphosphine)palladium(0) that is widely used to catalyze C-C coupling reactions in organic synthesis.
        3. in vitamin synthesis and production of pharmaceutical active ingredients, crop protection products and coatings, TPP is used in synthesis of vitamin D2, vitamin A, clindamycin and other drugs. Besides it plays an important role in reactions of plant pigments.
        4. as an oxidation and UV stabilizer in plastics. In the dye industry, Triphenylphosphine is used as sensitizer, heat stabilizers, light stabilizers, antioxidants, flame retardants, antistatic agents, rubber antiozonants and analytical reagent.
        5. as an initiator of several polymerization reactions, The anionic phosphine is usually isolated as the trisodium salt which reacts with rhodium to form a complex that finds use in industrial hydroformylation reactions.
        6. It is involved in the synthesis of biaryl compounds, phosphonium salts and other phosphorus compounds.
        7. As a reducing agent, it is used to prepare aromatic amines from the corresponding aromatic N-oxides.

        Chemical properties

        This product is colorless to pale yellow monoclinic crystal below the room temperature, colorless to pale yellow transparent oily liquid above the room temperature with skin irritation and a pungent odour. Its mp about 22 ℃and bp 360 ℃(0.1 MPa) , n25D of 1.589 and relative density of 1.184 (20 ℃). And it is miscible with alcohol, ether, benzene and acetone and other organic solvents, while insoluble in water.

        Name Reactions

        1. Mitsunobu reactions
          The triphenylphosphine combines with DEAD to generate a phosphonium intermediate that binds to the alcohol oxygen, activating it as a leaving group. Substitution by the carboxylate, mercaptyl, or other nucleophile completes the process.
        2. Ozonolysis reactions
          Ozonolysis allows the cleavage of alkene double bonds by reaction with ozone. Depending on the work up, different products may be isolated: reductive work-up gives either alcohols or carbonyl compounds, while oxidative work-up leads to carboxylic acids or ketones.
        3. Staudinger reactions
          Triphenylphosphine reacts with the azide to generate a phosphazide, which loses N2 to form an iminophosphorane. Aqueous work up leads to the amine and the very stable phosphine oxide.
        4. Appel reactions
          The reaction of triphenylphosphine and tetrahalomethanes (CCl4, CBr4) with alcohols is a ready method to convert an alcohol to the corresponding alkyl halide under mild conditions. The yields are normally high.
          This reaction is somewhat similar to the Mitsunobu Reaction, where the combination of a phosphine, a diazo compound as a coupling reagent, and a nucleophile are used to invert the stereochemistry of an alcohol or displace it.
        Name Reactions (Mitsunobu Ozonolysis  Staudinger Appel reactions)

        Friedel-krogh`s method

        The optimum reaction conditions: catalyst dosage 48g, reaction time 8h, the reaction temperature 400 ℃, the yield 63.5%. After sulfur, phosphorus trichloride and benzene reflux reacted directly, the generated triphenyl phosphine sulfide compound were deoxidized into triphenylphosphine by iron powder.

        Uses

        1. In pesticide industry, Triphenylphosphine is used in the synthesis of an organophosphorus intermediate, trimethyl phosphite in ester exchange method. And then a series of organophosphorus pesticides such as dichlorvos, monocrotophos and phosphamidon can be further obtained. In addition, it can be used as stabilizers in the synthesis of rubber and resins, antioxidants in polyvinyl chloride, and raw material in the synthesis of alkyd resins and polyester resins.
        2. Used in organic synthesis, polymerization initiator, raw materials of antibiotic drugs clindamycin, standard samples in organic trace analysis determination of phosphorus.
        3. Widely used in pharmaceutical, petrochemical, paint, rubber and other industries, as catalyst, accelerator, flame retardant, heat and light stabilizer, lubricant, antioxidant etc.
        4. In organic synthesis, such as synthesis of phosphorus salts and other phosphorus compounds.

        Production methods

        In this preparation method, phenol and phosphorus trichloride was used as raw materials. After esterification and vacuum distillation, the product namely triphenyl phosphite can be obtained.
        3C6H5OH + PCl3 [15~20 ℃] → (C3H5O) 3P + 3HCl
        Specific process can be classified into batch and continuous processes.
         (1) Batch process
        The phenol was added into the reactor, after warming to melt phosphorus trichloride was added to react with phenol at 70~90 ℃. After the phosphorus trichloride addition was completed, the temperature of reaction mixture was raised to about 150 ℃. After the removal of hydrogen chloride and unreacted phenol dissolved under reduced pressure at a high temperature, the product can be achieved.
        (2) The use of a tower reactor
        Phenol was feeding under the condenser located in the upper portion of the tower, while phosphorus trichloride enters above the receptacle located in the lower portion of the tower. Both reacted in the tower, and the product was collected in the receiver, meanwhile by-product hydrogen chloride was introduced into the absorber tower via the upper end of the condenser. After some process of the crude ester such as distillation, the product can be obtained.

        Hazards & Safety Information

        Category: toxic substances
        Toxicity degree: grading poisoning
        Acute toxicity: oral-rat LD50: 700 mg/kg; Oral-Mouse LD50: 1000 mg/kg
        Skin irritation Data: rabbit 500 mg/24 hours severe; Eyes-rabbit 500 mg/24 hr mild
        Flammability hazard characteristics: thermal decomposition into toxic phosphide
        Storage characteristics: ventilated, low-temperature and dry storehouse; stored and transported separately with food raw materials
        Extinguishing agent: carbon dioxide, sand, water, foam

        Chemical Properties

        White, crystalline solid. Insoluble inwater; slightly soluble in alcohol; soluble in benzene, acetone, carbon tetrachloride. Combustible.

        Uses

        Combining organic compound; microcosmic salt;phosphorous compound

        Uses

        PTC catalyst 

        Uses

        It is used in the synthesis of organic and organometallic compounds.

        Uses

        In organic synthesis; polymerization initiator.

        Production Methods

        Manufactured from phenylmagnesium bromide and phosphorus trichloride.

        Reactivity Profile

        Triphenylphosphine reacts vigorously with oxidizing materials. .

        Health Hazard

        ACUTE/CHRONIC HAZARDS: Toxic; when heated to decomposition, emits highly toxic fumes of phosphine and POx.

        Safety Profile

        Moderately toxic by ingestion. Mildly toxic by inhalation. A skin and eye irritant. Combustible when exposed to heat or flame. Slight explosion hazard in the form of vapor when exposed to flame. Can react vigorously with oxidizing materials. To fight fire, use dry chemical, fog, CO2. When heated to decomposition it emits highly toxic fumes of phosphne and POx. See also PHOSPHINE and PHENOL.

        Purification Methods

        It crystallises from hexane, MeOH, diethyl ether, CH2Cl2/hexane or 95% EtOH. Dry it at 65o/<1mm over CaSO4 or P2O5. Chromatograph it through alumina using (4:1) *benzene/CHCl3 as eluent. [Blau & Espenson et al. J Am Chem Soc 108 1962 1986, Buchanan et al. J Am Chem Soc 108 1537 1986, Randolph & Wrighton J Am Chem Soc 108 3366 1986, Asali et al. J Am Chem Soc 109 5386 1987.] It has also been crystallised twice from pet ether and 5 times from Et2O/EtOH to give m 80.5o. Alternatively, dissolve it in conc HCl, and upon dilution with H2O it separates because it is weakly basic, it is then crystallised from EtOH/Et2O. It recrystallises unchanged from AcOH. [Forward et al. J Chem Soc Suppl. p121 1949, Muller et al. J Am Chem Soc 78 3557 1956.] 3Ph3P.4HCl crystallises out when HCl gas is bubbled through an Et2O solution, it has m 70-73o, but recrystallises very slowly and is deliquescent. The hydriodide, made by adding Ph3P to hydriodic acid, is not hygroscopic and decomposes at ~100o. The chlorate (1:1) salt has m 165-167o, but decomposes slowly at 100o. All salts hydrolyse in H2O to give Ph3P [IR, UV: Sheldon & Tyree J Am Chem Soc 80 2117 1958, pK: Henderson & Streuli J Am Chem Soc 82 5791 1960, Kosolapoff, Organophosphorus Compounds, Wiley 1950]. [Beilstein 16 IV 951.] § Available commercially on a polystyrene or polyethyleneglycol support.

        Triphenylphosphine Preparation Products And Raw materials

        Raw materials

        Preparation Products


        Triphenylphosphine Suppliers

        Global( 491)Suppliers
        Supplier Tel Fax Email Country ProdList Advantage
        Anhui Jinshan Chemical Technology Co., Ltd. 18018884665
        - zhjinshanhg@163.com China 2 58
        Shandong hongchuan chemical co. LTD 0546-8339803
        13325053308@163.com CHINA 1 58
        Beijing Ouhe Technology Co., Ltd 010-82967028-
        +86-10-82967029 2355560935@qq.com China 12495 60
        Wuxi QianFeng Chemical Technology Co., Ltd. 0510-82860650-
        0510-82025215 qfhg@qianfengchem.com; China 40 55
        Shanghai Chang-Gen Chemical Technology Co., Ltd. +86 (21) 6910-6824
        +86 (21) 6910-6814 sales@shcgchem.com China 13 60
        Wuhan Greatwall chemical Co,.LTD 400-027-6116 027-86647488
        027-86647499 sales@chemgreatwall.com China 1940 55
        Shanghai Aladdin Bio-Chem Technology Co.,LTD 021-20337333/400-620-6333
        021-50323701 sale@aladdin-e.com China 24984 65
        Wuxi Henghui Chemical Co., Ltd. 0510-82328705
        webmaster@unionchems.com CHINA 26 58
        Shanghai Jinsai Pharmaceutical and Chemical Co., Ltd. 21-57362983-
        021-57362993 parkbe@hotmail.com China 10 58
        Suzhou Hengning Pharmaceutical Technology Co., Ltd. 0512-65649061-
        0512-65649061 hengningpharma@163.com; China 151 58

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        View Lastest Price from Triphenylphosphine manufacturers

        Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
        2019-08-01 Triphenylphosphine
        603-35-0
        US $1.00 / KG 1KG 99% 100MT Henan Xiangtong Chemical Co., Ltd.
        2019-05-10 Triphenylphosphin
        603-35-0
        US $8776.00 / KG 25KG 99.5% 200TONS Yunbio Tech Co.,Ltd.
        2018-08-06 Triphenylphosphine oxide
        603-35-0
        US $10.00 / KG 10KG 99% 10KG career henan chemical co

        Triphenylphosphine Spectrum


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