PHOSGENE

Base Information

• Chemical Name: PHOSGENE
• CAS No.: 75-44-5
• Deprecated CAS: 957761-04-5,1173022-33-7
• Molecular Formula: CCl2 O
• Molecular Weight: 98.9164
• Hs Code.: 2812103000
• European Community (EC) Number: 200-870-3
• ICSC Number: 0007
• UN Number: 1076
• UNII: 117K140075
• DSSTox Substance ID: DTXSID0024260
• Nikkaji Number: J1.943G
• Wikipedia: Phosgene
• Wikidata: Q189090
• NCI Thesaurus Code: C163688
• Metabolomics Workbench ID: 54060
• Mol file: 75-44-5.mol

Synonyms:Phosgene(8CI); CG; Carbon dichloride oxide; Carbon oxychloride; Carbonyl chloride;Carbonyl dichloride; Chloroformyl chloride; Dichloroformaldehyde; Phosgen

Chemical Property of PHOSGENE

Chemical Property:

• Appearance/Colour: colourless gas
• Vapor Pressure: 1180 mm Hg ( 20 °C)
• Melting Point: -118 C
• Refractive Index: 1.3561
• Boiling Point: 8.2 °C at 760 mmHg
• Flash Point: 4°C
• PSA: 17.07000
• Density: 1.523 g/cm³
• LogP: 1.58400
• Storage Temp.: 2-8°C
• Water Solubility.: slightly soluble and hydrolyzed in H2O; soluble benzene, toluene [HAW93]
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 97.9326200
• Heavy Atom Count: 4
• Complexity: 29
• Transport DOT Label: Poison Gas Corrosive

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Very toxic via inhalation, strong irritant to eyes. TLV: 0.1 ppm.
• Hazard Codes: T+,F
• Statements: 26-34-67-65-63-48/20-11-39/26
• Safety Statements: 9-26-36/37/39-45-62-28-16

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: C(=O)(Cl)Cl
• Inhalation Risk: A harmful concentration of this gas in the air will be reached very quickly on loss of containment.
• Effects of Short Term Exposure: Rapid evaporation of the liquid may cause frostbite. The substance is irritating to the eyes and respiratory tract. Inhalation of the gas may cause lung oedema and chemical pneumonitis. The effects may be delayed. Medical observation is indicated. Exposure at high levels could cause death.
• Effects of Long Term Exposure: Lungs may be affected by repeated or prolongated exposure. This may result in impaired functions and decreased resistance to infection.
• Uses: Phosgene is used mainly as an intermediate in the manufacture of many types of compounds, including barbiturates; chloroformates and thiochloroforrnates; carbamoyl chlorides, acid chlorides, and acid anhydrides; carbamates; carbonates and pyrocarbonates; urethanes; ureas; azo-urea dyes, triphenylmethane dyes, and substituted benzophenones; isocyanates and isothiocyanates; carbazates and carbohydrazides; malonates; carbodimides; and oxazolidinedions. It is also used in bleaching sand for glass manufacture and as a chlorinating agent. Phosgene is an important commodity and a major industrial chemical used in the production of pesticides and plastics. As a chemical intermediate it is used in the manufacture of dyestuffs, isocyanates and their derivatives, and many other organic chemicals. It was formerly used as a war gas and is also known by itsmilitary designation as “CG.”Much of the clinical information on phosgene poisoning has been developed in the context of its military applications. It is also used in the pharmaceutical industries and in metallurgy. Of the total phosgene produced, 62% is used to manufacture toluene diisocyanate, and varying amounts are used to manufacture related chemicals. COCl2 is a very poisonous gas that was used in combat in the early twentieth century. When not concentrated, it smells like newly cut hay or grass. PHOSGENE is an intermediate in organic synthesis, especially production of toluene diisocyanate and polymethylene polyphenylisocyanate; in metallurgy to separate ores by chlorination of the oxides and volatilization; occurs as a product of combustion whenever a volatile chlorine compound comes in contact with a flame or very hot metal; originally manufactured as an agent for chemical warfare during World War I.
• Physical Properties: Colorless gas; density 4.34 g/L; heavier than air, density in air 3.41 (air=1); liquefies at 8.3°C; liquid density 1.432 g/mL; freezes at –118°C; slightly soluble in water with slow decomposition; also decomposed by alcohol and acids; soluble in benzene, toluene and acetic acid; critical temperature 182°C; critical pressure 56.04 atm; critical volume 190 cm3/mol.
• Description: Phosgene was prepared first in 1812 by reacting carbon monoxide with chlorine. Phosgene was used historically as a military gas in warfare. At present, it is used extensively to make polyurethanes. These urethane polymers produce polycarbonates and chloroformates for making pesticides and pharmaceuticals. Phosgene is a colourless, reactive, non-flammable gas that is heavier than air with a musty hay odour. Phosgene is commonly stored under high pressure as a liquid. Phosgene reacts with water to form corrosive acids, reacts with most metals in the presence of moisture, liberating hydrogen, an extremely flammable gas, and reacts violently with alkalis. As an industrial and commercially important chemical, phosgene is a precursor material/chemical intermediate, and has extensive application in the manufacture of a wide range of products such as polymers – polyurethanes and polycarbonates – pesticides, medicines, dyestuffs, some insecticides, pharmaceuticals, and in metallurgy.
• Physical properties: Colorless gas at ambient temperature; strong, pungent odor; density of the gas 4.045 g/L at 25°C; density of the liquid 1.392 g/mL at 4°C; liquefies to a light yellow fluid at 8.2°C; freezes at -128°C; critical temperature 182°C, critical pressure 55.96 atm, critical volume 190 cm3/mol; slightly soluble in water with slow hydrolysis; soluble in benzene, toluene and acetic acid.

Technology Process of PHOSGENE

There total 457 articles about PHOSGENE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

tetrachloromethane (56-23-5) + (4-nitro-phenyl)-carbamic acid trichloromethyl ester (859807-24-2) → phosgene (75-44-5) + 4-Nitrophenyl isocyanate (100-28-7)

Guidance literature:

Reference yield:

(4-nitro-phenyl)-carbamic acid trichloromethyl ester (859807-24-2) → phosgene (75-44-5) + 4-Nitrophenyl isocyanate (100-28-7)

Guidance literature:

at 100 ℃;

Reference yield:

C7H7ClNO2(1+)*Cl(1-) → 4-methylpyridine-1-oxide (1003-67-4) + phosgene (75-44-5)

Guidance literature:

In dichloromethane; at 15 - 35 ℃; Equilibrium constant; Thermodynamic data; ΔH (at 25 deg C);

upstream raw materials:

pyridine

bis(trichloromethyl) oxalate

chlorobenzene

carbon disulfide

Downstream raw materials:

chloro-formic acid tetrahydrofurfuryl ester

4-methyl-piperazine-1-carbonyl chloride

bis(4-methylpiperazin-1-yl)methanone

benzonitrile

Refernces

• 1、 Calderazzo, Fausto,Belli Dell'Amico, Daniela. "Transition-metal-catalyzed oxidation of carbon monoxide by dichlorine to produce phosgene". . p. 3639 - 3642. Retrieved 1982.
• 2、 Armstrong. "". . p. 245. Retrieved 1870.
• 3、 Ramsperger, H. C.,Waddington, G.. "-". . p. 214 - 220. Retrieved 1933.
• 4、 Hwang, Son-Jong,Petucci, Chris,Raftery, Daniel. "In situ solid-state NMR studies of trichloroethylene photocatalysis: Formation and characterization of surface-bound intermediates". . p. 4388 - 4397. Retrieved 1998.
• 5、 Tatarova,Trofimova,Gorban',Khaliullin. "Reaction of carbon tetrachloride with hydrogen peroxide". . p. 1403 - 1406. Retrieved 2004.
• 6、 Gupta, Navneet K.,Pashigreva, Anastasia,Pidko, Evgeny A.,Hensen, Emiel J. M.,Mleczko, Leslaw,Roggan, Stefan,Ember, Erika E.,Lercher, Johannes A.. "Bent Carbon Surface Moieties as Active Sites on Carbon Catalysts for Phosgene Synthesis". . p. 1728 - 1732. Retrieved 2016.
• 7、 Pena, Laura A.,Chan, Alissa M.,Cohen, Larissa R.,Hou, Karen,Harvey, Brent M.,Hoggard, Patrick E.. "Photodecomposition of chloroform catalyzed by unmodified MCM-41 mesoporous silica". . p. 760 - 766. Retrieved 2014.
• 8、 Lyons,Dikinson. "". . p. 443. Retrieved 1935.
• 9、 Chapman, A. T.. "". . p. 419 - 422. Retrieved 1935.
• 10、 Romano, Rosana M.,Della Vedova, Carlos O.,Downs, Anthony J.,Tobon, Yeny A.,Willner, Helge. "New members of an old family: Isolation of IC(O)CI and IC(O)Br and evidence for the formation of weakly bound Br...CO". . p. 3241 - 3248. Retrieved 2005.