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Triphenylphosphine

description Chemical properties Name Reactions Friedel-krogh`s method Uses Production methods Hazards & Safety Information
Triphenylphosphine
Triphenylphosphine
CAS No.
603-35-0
Chemical Name:
Triphenylphosphine
Synonyms
PPh3;PP-360;Triphenyl;'LGC' (4006);Trifenylfosfin;Triphenyphosphine;Trihenylphosphine;Triphenylphosphane;triphenyl-phosphin;Triphenylphosphide
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)
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
Water Solubility 
Insoluble
Merck 
14,9743
BRN 
610776
Stability:
Stable. Incompatible with oxidizing agents, acids.
CAS DataBase Reference
603-35-0(CAS DataBase Reference)
NIST Chemistry Reference
Phosphine, triphenyl-(603-35-0)
EPA Substance Registry System
Phosphine, triphenyl-(603-35-0)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
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
TSCA  Yes
HS Code  29310095
Hazardous Substances Data 603-35-0(Hazardous Substances Data)
Symbol(GHS):
Signal word: Warning
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H317 May cause an allergic skin reaction Sensitisation, Skin Category 1 Warning P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H373 May cause damage to organs through prolonged or repeated exposure Specific target organ toxicity, repeated exposure Category 2 Warning P260, P314, P501
Precautionary statements:
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P321 Specific treatment (see … on this label).
P333+P313 IF SKIN irritation or rash occurs: Get medical advice/attention.

Triphenylphosphine price More Price(19)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.08270 Triphenylphosphine 603-35-0 1EA $22.5 2017-11-08 Buy
Sigma-Aldrich 8.08270 Triphenylphosphine 603-35-0 2EA $62.5 2017-11-08 Buy
TCI Chemical T0519 Triphenylphosphine >95.0%(T) 603-35-0 25g $18 2017-12-01 Buy
TCI Chemical T0519 Triphenylphosphine >95.0%(T) 603-35-0 100g $39 2017-12-01 Buy
Cayman Chemical 705018 LPO Assay Triphenylphosphine >98% 603-35-0 1ea $25 2017-11-08 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 solid

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.

General Description

White crystals.

Air & Water Reactions

Highly flammable. Insoluble in water.

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.

Fire Hazard

Triphenylphosphine is combustible.

Triphenylphosphine Preparation Products And Raw materials

Raw materials

Preparation Products


Triphenylphosphine Suppliers

Global( 385)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Shanghai Bojing Chemical Co.,Ltd.
+86-21-37122233
+86-21-37127788 Candy@bj-chem.com CHINA 497 55
Mainchem Co., Ltd.
0592-6210733
0592-6210733 sales@mainchem.com CHINA 1948 55
Shanghai Time Chemicals CO., Ltd.
+86-021-57951555
+86-021-57951555 jack.li@time-chemicals.com CHINA 1372 55
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3229 55
360 Reagent 025- 66028182
02557626880 yftan@aikonchem.com China 19043 55
Beijing Ouhe Technology Co., Ltd +86-10-4006331231;+86-10-51280831;+86-10-82967028
+86-10-82967029 sales@ouhechem.com China 10813 60
Hangzhou Right Chemical Co., Ltd. +86 0571 88254703
+86 0571 88254723 info@ruikechem.com China 83 58
Wuxi QianFeng Chemical Technology Co., Ltd. 0510-82860650 QQ:125867945
0510-82025215 qfhg@qianfengchem.com China 29 55
Shanghai Chang-Gen Chemical Technology Co., Ltd. +86 (21) 6910-6824
+86 (21) 6910-6814 sales@shcgchem.com China 9 60
Wuhan Greatwall chemical Co,.LTD 400-027-6116 027-86647488
027-86647499 sales@chemgreatwall.com China 1013 55

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