FACTOID # 22: South Dakota has the highest employment ratio in America, but the lowest median earnings of full-time male employees.
 
 Home   Encyclopedia   Statistics   States A-Z   Flags   Maps   FAQ   About 
   
 
WHAT'S NEW
RELATED ARTICLES
People who viewed "Phosgene" also viewed:
 

SEARCH ALL

FACTS & STATISTICS    Advanced view

Search encyclopedia, statistics and forums:

 

 

(* = Graphable)

 

 


Encyclopedia > Phosgene
Phosgene
Structure and dimensions of the phosgene molecule Space-filling model of the phosgene molecule
General
Systematic name Carbonyl chloride
Other names Phosgene
CG
Carbonic acid dichloride
Carbon dichloride oxide
Carbon oxychloride
Carbonyl dichloride
Chloroformyl chloride
Dichloroformaldehyde
Molecular formula CCl2O
SMILES O=C(Cl)Cl
Molar mass 98.9 g mol-1
Appearance colorless gas
CAS number [75-44-5]
Properties
Density and phase 4.248 g dm-3, gas (15 °C)
Solubility in water hydrolysis
Other solvents chlorocarbons
Melting point −118 °C (155 K)
Boiling point 8 °C (281 K)
Structure
Molecular shape Planar
Dipole moment 1.17 D
Hazards
MSDS http://www.vngas.com/pdf/g67.pdf
EU classification Very toxic (T+)
NFPA 704
0
4
1
 
R-phrases R26, R34
S-phrases (S1/2), S9, S26,
S36/37/39, S45
Flash point non-flammable
RTECS number SY5600000
Related compounds
Other anions Carbonyl fluoride
Other cations Nitrosyl chloride
Related compounds Carbonic acid
Urea
Carbon monoxide
Chloroformic acid
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

Phosgene is a highly toxic chemical compound with the formula COCl2. Image File history File links Size of this preview: 800 × 504 pixelsFull resolution (1100 × 693 pixel, file size: 70 KB, MIME type: image/png) File historyClick on a date/time to view the file as it appeared at that time. ... Image File history File links Size of this preview: 676 × 599 pixelsFull resolution (1100 × 975 pixel, file size: 178 KB, MIME type: image/png) File historyClick on a date/time to view the file as it appeared at that time. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article or section does not cite any references or sources. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... This article does not cite any references or sources. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that this article or section be merged with Solution. ... This article describes water from a scientific and technical perspective. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... Italic text This article is about the boiling point of liquids. ... four sp³ orbitals three sp² orbitals In chemistry, hybridisation or hybridization (see also spelling differences) is the concept of mixing atomic orbitals to form new hybrid orbitals suitable for the qualitative description of atomic bonding properties. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main European Union law concerning chemical safety. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... For other uses, see Flash point (disambiguation). ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... This article is about the electrically charged particle. ... Carbonyl fluoride is a very toxic gas. ... This article is about the electrically charged particle. ... Nitrosyl chloride is the chemical compound NOCl. ... Carbonic acid (ancient name acid of air or aerial acid) has the formula H2CO3. ... Urea is an organic compound with the chemical formula (NH2)2CO. Urea is also known as carbamide, especially in the recommended International Nonproprietary Names (rINN) in use in Europe. ... Carbon monoxide, with the chemical formula CO, is a colorless, odorless, and tasteless gas. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Toxic redirects here, but this is also the name of a song by Britney Spears; see Toxic (song) Look up toxic and toxicity in Wiktionary, the free dictionary. ... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... This article or section does not cite any references or sources. ...


This gas gained infamy as a chemical weapon during World War I, but it is also a valuable industrial reagent and building block in organic synthesis. It is colourless, but can appear as a white or yellowish haze when released into air, due to refraction of light. In low concentrations, its odor resembles recently cut hay or green corn (maize); at higher concentrations, it may be strongly unpleasant. In addition to its industrial production, small amounts occur naturally from the breakdown of chlorinated compounds and the combustion of chlorine-containing organic compounds. Dressing the wounded during a gas attack by Austin O. Spare, 1918. ... “The Great War ” redirects here. ... Organic synthesis is the construction of organic molecules via chemical processes. ... Stacked hay in Romania Haystacks on stilts in Paddy fields, North Kanara, India Hay is dried grass or legumes cut, stored, and used for animal feed, particularly for grazing animals like cattle, horses, goats and sheep. ... “Corn” redirects here. ... A combustion reaction taking place in a igniting match Combustion or burning is a complex sequence of exothermic chemical reactions between a fuel and an oxidant accompanied by the production of heat or both heat and light in the form of either a glow or flames. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting of primarily carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ...

Contents

Structure and basic properties

Phosgene is a planar molecule as predicted by VSEPR theory. The C=O distance is 1.18 Å, the C---CL distance is 1.74 Å and the Cl---C---Cl angle is 111.8°.[1] Valence shell electron pair repulsion theory (VSEPR) (1957) is a model in chemistry that aims to generally represent the shapes of individual molecules [1] . To achieve this, it is necessary to construct a valid Lewis structure that shows all of the bonds within the molecule and the locations of lone... This article is about a unit of length. ...


Phosgene is the simplest and one of the most electrophilic acid chlorides. This high electrophilicity is manifested in the tendency of phosgene to react with water, that is, hydrolyze. This hydrolysis reaction releases hydrogen chloride and carbon dioxide: In chemistry, an electrophile (literally electron-lover) is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to bond to a substance. ... In organic chemistry, an acid chloride (or acyl chloride) is very reactive derivative of a carboxylic acid. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... R-phrases , S-phrases , , , , Flash point non-flammable Supplementary data page Structure and properties n, εr, etc. ... In order to meet Wikipedias quality standards, this article requires cleanup. ...

COCl2 + H2O → CO2 + 2 HCl

The toxicity of phosgene is mainly due to the HCl that is released in this hydrolysis reaction.


History

Phosgene was synthesized by the chemist John Davy (1790-1868) in 1812 by exposing a mixture of carbon monoxide and chlorine to sunlight. He named it in reference to use of light to promote the reaction; from Greek, phos (light) and gene (born).[2] It gradually became important in the chemical industry as the 19th century progressed, particularly in dye manufacturing. John Davy (1790-1868) was a British doctor and amateur chemist, and brother of the noted chemist Sir Humphry Davy. ... For the overture by Tchaikovsky, see 1812 Overture; For the wars, see War of 1812 (USA - United Kingdom) or Patriotic War of 1812 (France - Russia) For the Siberia Airlines plane crashed over the Black Sea on October 4, 2001, see Siberia Airlines Flight 1812 1812 was a leap year starting... Prism splitting light High Resolution Solar Spectrum Sunlight in the broad sense is the total spectrum of the electromagnetic radiation given off by the Sun. ... Alternative meaning: Nineteenth Century (periodical) (18th century — 19th century — 20th century — more centuries) As a means of recording the passage of time, the 19th century was that century which lasted from 1801-1900 in the sense of the Gregorian calendar. ...

Further information: Use of poison gas in World War I

Phosgene was stockpiled as part of U.S. military arsenals until well after World War II in the form of aerial bombs and mortar rounds.[3], the United States began disposing of its stockpiles in 1969. Even before then, the importance of phosgene as a weapon had declined as the more lethal nerve agents entered stockpiles. A poison gas attack in World War I. The use of poison gas was a major military innovation of the First World War. ... Combatants Allied powers: China France Great Britain Soviet Union United States and others Axis powers: Germany Italy Japan and others Commanders Chiang Kai-shek Charles de Gaulle Winston Churchill Joseph Stalin Franklin Roosevelt Adolf Hitler Benito Mussolini Hideki Tōjō Casualties Military dead: 17,000,000 Civilian dead: 33,000... Also: 1969 (Stargate SG-1) episode. ... Nerve agents (also known as nerve gases, though these chemicals are liquid at room temperature) are a class of phosphorus-containing organic chemicals (organophosphates) that disrupt the mechanism by which nerves transfer messages to organs. ...


Production

Around 2 million tons are produced annually[4] for use in the synthesis of fine chemicals and polymers. Industrially, phosgene is produced by passing purified carbon monoxide and chlorine gas through a bed of highly porous carbon, which acts as a catalyst. The chemical equation for this reaction follows: Carbon monoxide, with the chemical formula CO, is a colorless, odorless, and tasteless gas. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... General Name, symbol, number carbon, C, 6 Chemical series nonmetals Group, period, block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... It has been suggested that this article or section be merged into Catalysis. ... A chemical equation is a symbolic representation of a chemical reaction where the reactant entities are given on the left hand side and the product entities on the right hand side. ... Vapours of hydrogen chloride in a beaker and ammonia in a test tube meet to form a cloud of a new substance, ammonium chloride A chemical reaction is a process that results in the interconversion of chemical substances. ...

CO + Cl2 → COCl2

The reaction is exothermic, therefore the reactor must be cooled to carry away the heat it produces. Typically, the reaction is conducted between 50 and 150 °C. Above 200 °C, phosgene decomposes back into carbon monoxide and chlorine.


Upon ultraviolet radiation in the presence of oxygen, chloroform slowly converts into phosgene via a radical reaction. To suppress this photodegradation, chloroform is often stored in brown-tinted glass containers. “UV” redirects here. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... R-phrases , , , S-phrases , Flash point Non-flammable U.S. Permissible exposure limit (PEL) 50 ppm (240 mg/m3) (OSHA) Supplementary data page Structure and properties n, εr, etc. ... In chemistry, radicals (often referred to as free radicals) are atomic or molecular species with unpaired electrons on an otherwise open shell configuration. ...


Because of safety issues, phosgene is almost always produced and consumed within the same plant. It is listed on schedule 3 of the Chemical Weapons Convention: all production sites manufacturing more than 30 tonnes per year must be declared to the OPCW.[5] Although much less dangerous than nerve agents, phosgene is still regarded as a viable chemical warfare agent. Schedule 3 substances, in the sense of the Chemical Weapons Convention, are either toxic enough to be used as chemical weapons, or precursors of other listed substances. ... Chemical Weapons Convention Opened for signature January 13, 1993 in Paris Entered into force April 29, 1997 Conditions for entry into force Ratification by 50 states and the convening of a Preparatory Commission Parties 181 (as of Oct. ... The Organisation for the Prohibition of Chemical Weapons (OPCW) is an agency of the United Nations. ... Nerve agents (also known as nerve gases, though these chemicals are liquid at room temperature) are a class of phosphorus-containing organic chemicals (organophosphates) that disrupt the mechanism by which nerves transfer messages to organs. ...


Uses

Phosgene is used chiefly in the production of polymers including polyurethanes, polycarbonates, and polyureas. It is also valuable in the preparation of fine chemicals.[6] In the laboratory for small-scale reactions, gaseous phosgene has increasingly been supplanted by more easily handled reagents that effect comparable transformations: diphosgene (chloroformic acid ester), which is a liquid at room temperature, or triphosgene, a crystalline substance. Following are three of many useful reactions involving phosgene. A polymer (from Greek: πολυ, polu, many; and μέρος, meros, part) is a substance composed of molecules with large molecular mass composed of repeating structural units, or monomers, connected by covalent chemical bonds. ... A polyurethane is any polymer consisting of a chain of organic units joined by urethane links. ... Polycarbonates are a particular group of thermoplastic polyesters. ... The general formula for polyureas. ... A reagent or reactant is any substance used in a chemical reaction. ... Diphosgene (ClCO2CCl3) Diphosgene (Trichloromethyl chloroformate, ClCO2CCl3) is a chemical originally developed for chemical warfare, a few months after the first use of phosgene. ... Chemical Structure of Triphosgene Triphosgene (Bis(trichloromethyl) carbonate, C3Cl6O3) is a chemical compound that is used as a substitute for phosgene. ...


Synthesis of carbonates

Diols react with phosgene to give either linear or cyclic carbonates (R = H, alkyl, aryl): A diol is a chemical compound containing two hydroxyl groups (-OH groups). ...

HOCR2-X-CR2OH + COCl2 → 1/n [OCR2-X-CR2OC(O)-]n + 2 HCl

Polycarbonates are an important class of engineering thermoplastic, found for example in lenses in eye glasses. Polycarbonates are a particular group of thermoplastic polyesters. ... A thermoplastic is a material that is plastic or deformable, melts to a liquid when heated and freezes to a brittle, glassy state when cooled sufficiently. ...


Synthesis of isocyanates

The synthesis of isocyanates from amines illustrates the electrophilic character of this reagent and its use in introducing the equivalent of "CO2+" (R = alkyl, aryl): Isocyanate is the chemical group of atoms -N=C=O (1 nitrogen, 1 carbon, 1 oxygen), as opposed to cyanate, -O-C≡N, which is formed from cyanogen in the normal -ate manner. ... In chemistry, an electrophile (literally electron-lover) is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to bond to a substance. ... An alkyl is a univalent radical containing only carbon and hydrogen atoms arranged in a chain. ... In the context of organic molecules, aryl refers to any member of the set of functional groups or substituents that are derived from a simple aromatic ring. ...

RNH2 + COCl2 → RN=C=O + 2 HCl

Such reactions are conducted in the presence of a base such as pyridine that absorbs the hydrogen chloride. Pyridine is a chemical compound with the formula C5H5N. It is a liquid with a distinctively putrid odour. ... R-phrases , S-phrases , , , , Flash point non-flammable Supplementary data page Structure and properties n, εr, etc. ...


Synthesis of acid chlorides and esters

It is also used to produce acid chlorides: In organic chemistry, an acid chloride (or acyl chloride) is very reactive derivative of a carboxylic acid. ...

RCO2H + COCl2 → RC(O)Cl + HCl + CO2

Such acid chlorides react with amines and alcohols to give respectively amides and esters, which are common intermediates in the dye, pesticide, and pharmaceutical industries. Despite being an efficient method of synthesizing acyl chloride from carboxylic acids, laboratory safety issues led to the use of the less toxic thionyl chloride. In order to meet Wikipedias quality standards, this article requires cleanup. ... Look up dye in Wiktionary, the free dictionary. ... A cropduster spreading pesticide. ... Pharmacology (in Greek: pharmacon is drug, and logos is science) is the study of how chemical substances interfere with living systems. ... R-phrases , , , S-phrases , , , Flash point non flammable Supplementary data page Structure and properties n, εr, etc. ...


Safety

See MSDS. Phosgene is an insidious poison as the odor may not be noticed and symptoms may be slow to appear.[7] Like many reactive chlorides, phosgene combines with water in the tissues of the respiratory tract to form hydrochloric acid. Phosgene is stable when stored in dry steel containers.[3]. Phosgene is a member of a class of organic chemicals known as alkylating agents.[citation needed] These agents can react with both DNA and with enzymes (polymerases) that are responsible for replication of DNA in cells. An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... The chemical compound hydrochloric acid is the aqueous (water-based) solution of hydrogen chloride gas (HCl). ... Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. ... ITaq DNA polymerase A polymerase (EC 2. ...


References

  1. ^ Nakata, M.; Kohata, K.; Fukuyama, T.; Kuchitsu, K. “Molecular Structure of Phosgene as Studied by Gas Electron Diffraction and Microwave Spectroscopy. The rz Structure and Isotope Effect ” Journal of Molecular Spectroscopy 1980, Volume 83, Pages 105-117. doi:10.1016/0022-2852(80)90314-8
  2. ^ John Davy (1812). "On a Gaseous Compound of Carbonic Oxide and Chlorine". Philosophical Transactions of the Royal Society of London 102: 144-151. 
  3. ^ a b FM 3-8 Chemical Reference handbook; US Army; 1967
  4. ^ http://cbwinfo.com/Chemical/Pulmonary/CG.shtml
  5. ^ http://www.opcw.org/html/db/cwc/eng/cwc_annex_verification_part_VIII.html
  6. ^ Hamley, P. "Phosgene" Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley, New York. DOI: 10.1002/047084289X.rp149.
  7. ^ Borak J., Diller W. F. (2001). "Phosgene exposure: mechanisms of injury and treatment strategies". Journal of Occupational and Environmental Medicine 43 (2): 110-9. PMID 11227628. 

A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...

External links

This article forms part of the series
Chemical warfare
Blood agents: Cyanogen chloride (CK) – Hydrogen cyanide (AC)
Blister agents: Lewisite (L) – Sulfur mustard gas (HD, H, HT, HL, HQ) – Nitrogen mustard gas (HN1, HN2, HN3)
Nerve agents: G-Agents: Tabun (GA) – Sarin (GB) – Soman (GD) – Cyclosarin (GF) – GV | V-Agents: VEVGVMVX | Novichok agents
Pulmonary agents: ChlorineChloropicrin (PS) – Phosgene (CG) – Diphosgene (DP)
Incapacitating agents: Agent 15 (BZ) – KOLOKOL-1
Riot control agents: Pepper spray (OC) – CS gasCN gas (mace) – CR gas
v  d  e

 
 

COMMENTARY     


Share your thoughts, questions and commentary here
Your name
Your comments

Want to know more?
Search encyclopedia, statistics and forums:

 


Press Releases |  Feeds | Contact
The Wikipedia article included on this page is licensed under the GFDL.
Images may be subject to relevant owners' copyright.
All other elements are (c) copyright NationMaster.com 2003-5. All Rights Reserved.
Usage implies agreement with terms, 1022, m