Carbonylchlorid

Phosgene

HCID 6371CAS 75-44-5

Grundinformationen

Standard-SMILES
O=C(Cl)Cl
InChIKey
YGYAWVDWMABLBF-UHFFFAOYSA-N
Summenformel
CCl2O
Durchschnittliche Molmasse
98,91 g/mol
Monoisotopische Masse
97,93262

Namen und Bezeichner

Bevorzugter Name
Phosgene
IUPAC
carbonyl dichloride
Lokaler Name
Carbonylchlorid
Englischer Name
PHOSGENE
Summenformel
CCl2O
Molmasse
98.92

Namen und Synonyme

PHOSGENECarbonyl dichlorideCarbonic dichloridePhosgenCarbon oxychlorideChloroformyl chlorideCarbonic chloride75-44-5CarbonylchloridFosgeenFosgenCarbon dichloride oxide
Weitere Namen anzeigen
Carbonyl chloridePhosgene solution
Carbonic acid dichlorideDichloroformaldehydeFosgeneCarbone (oxychlorure de)Combat gasKoolstofoxychlorideRCRA waste number P095Carbonio (ossicloruro di)

Datenbank-Bezeichner

CAS
75-44-5
PubChem CID
6371
DTXSID
DTXSID0024260
ChEBI
CHEBI:29365
UNII
117K140075
EC Number
200-870-3
Nikkaji
J1.943G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,8
Polarare Oberfläche (TPSA)
17,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
4

Experimentelle und physikochemische Eigenschaften

Odor · 4 Einträge

Suffocating odor; when diluted with air there is an odor reminiscent of moldy hay

Odor varies from strong and stifling when concentrated to hay-like in dilute form

Characteristic odor; the odor of the gas can be detected only briefly at the time of initial exposure. At about 0.5 ppm in air, the odor has been described as pleasant and similar to that of new-mown hay or cut green corn. At high concentration, the odor may be strong, stifling, and unpleasant.

Suffocating odor like musty hay

Density · 6 Einträge

1.432 at 32 °F (EPA, 1998) - Denser than water; will sink

1.3719 at 25 °C

Density at critical point: 0.52 g/cu cm

Relative density (water = 1): 1.4

1.43 (liquid at 32 °F)

1.3719 @25 °C

Viscosity6.8488X10-4 Pa.s at 263.15 K
Color/Form · 5 Einträge

Colorless gas [Note: A fuming liquid below 47 degrees F. Shipped as a liquefied compressed gas].

Colorless to light yellow liquid or easilty liquefied gas

Colorless gas at room temperature and normal pressure

Impurities may cause discoloration of the product to pale yellow to green /liquid/

Light yellow liquid when refrigerated or compressed.

Solubility · 5 Einträge

Very slightly soluble (NTP, 1992)

Slightly sol in water; freely sol in benzene, toluene, glacial acetic acid, and most liquid hydrocarbons

Soluble in benzene, carbon tetrachloride, chloroform, toluene, and acetic acid

Solubility in water: reaction

Slight

CorrosivityPhosgene used in anhydrous equipment with reagents is not corrosive to ordinary metals. In presence of moisture, corrosive conditions will develop rapidly, in which case monel, tantalum, or glass lined equipment may be used.

Physikochemische Eigenschaften

Schmelzpunkt
-118 ° · -118°
Siedepunkt
760 · bp760 8.2°
Dichte
0.94 g/mL · 0.94 g/mL at 20 °C
Dampfdruck
1180 mm · 1180 mm Hg ( 20 °C)
Brechungsindex
1.3561 · 1.3561
Flammpunkt
4 °C · 4 °C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation];H330: Fatal if inhaled [Danger Acute toxicity, inhalation]

P260, P264, P271, P280, P284, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P320, P321, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.2% (1 of 535) of reports.

Gefahrenhinweise

Hazards IdentificationToxic/poison by inhalation (TIH/PIH)
Regulatory Information · 6 Einträge

Chemical: Carbonic dichloride

Hazard Traits - Neurotoxicity; Respiratory Toxicity;Authoritative List - CA TACs; OEHHA RELs;Report - if used as a fragrance or flavor ingredient

Regulation (EC) No 1107/2009 (amended)

Carbonic dichloride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Carbonic dichloride are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 02-08-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/20452;Status: Active Update: 08-11-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/10463

Phosgene: HSNO Approval: HSR001066 Approved with controls

Other Safety Information · 2 Einträge

IMAP assessments - Carbonic dichloride: Environment tier I assessment;IMAP assessments - Carbonic dichloride: Human health tier I assessment

- Indoor Air: Phosgene (CG) can be released into indoor air as a gas.;- Water: Phosgene is unlikely to contaminate water because it breaks down rapidly upon contact with water to produce hydrochloric acid and carbon dioxide.;- Food: Phosgene is unlikely to contaminate food because it breaks down rapidly upon contact with water to produce hydrochloric acid and carbon dioxide.;- Outdoor Air: Phosgene (CG) can be released into outdoor air as a gas.;- Agricultural: If phosgene (CG) is released as a gas, it is highly unlikely to contaminate agricultural products.

DOT LabelPoison Gas Corrosive
Fire Hazards · 3 Einträge

For information on chemical warfare choking agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024);When heated to decomposition or on contact with water or steam, it will react to produce toxic and corrosive fumes. Reacts violently with aluminum; tert-butyl azido formate; 2,4-hexadiyn-1,6-diol; isopropyl alcohol; potassium; sodium; hexafluoro isopropylidene; amino lithium; lithium. Stable in steel containers if dry. Avoid moisture. (EPA, 1998)

· Some may burn but none ignite readily.;· Vapors from liquefied gas are initially heavier than air and spread along ground.;· Some of these materials may react violently with water.;· Cylinders exposed to fire may vent and release toxic and/or corrosive gas through pressure relief devices.;· Containers may explode when heated.;· Ruptured cylinders may rocket.;· For UN1005: Anhydrous ammonia, at high concentrations in confined spaces, presents a flammability risk if a source of ignition is introduced.

Not combustible.

Fire PotentialNONCOMBUSTIBLE

Sicherheit und Schutzausrüstung

Fire Fighting · 3 Einträge

For information on chemical warfare choking agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024);If necessary to stop flow of gas, use water spray to protect the personnel effecting shutoff. Sodium hydroxide or anhydrous ammonia have been used to neutralize phosgene.;Nonflammable. For small fires, use dry chemical or carbon dioxide. Use water spray, fog, or foam for larger fires. Do not get water inside containers. Move container from fire area if you can do so without risk. Stay away from the ends of tanks, and cool exposed containers with water until well after the fire is out. Isolate the area until gas has dispersed. (EPA, 1998)

In case of fire in the surroundings, use appropriate extinguishing media. In case of fire: keep cylinder cool by spraying with water. NO direct contact with water. Combat fire from a sheltered position.

- Phosgene (CG) is non-combustible.;- When heated to decomposition, phosgene (CG) produces toxic and corrosive fumes (hydrogen chloride, carbon monoxide, and chlorine).;- For small fires, use dry chemical or carbon dioxide.;- For large fires, use water spray, fog, or regular foam. Move containers from the fire area if it is possible to do so without risk to personnel. Do not get water inside containers. Damaged cylinders should be handled only by specialists.;- For fire involving tanks, fight the fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after the fire is out. Do not direct water at the source of the leak or at safety devices; icing may occur. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tanks. Always stay away from tanks engulfed in fire.;- Run-off from fire control may cause pollution.;- If the situation allows, control and properly dispose of run-off (effluent).

First Aid Measures · 3 Einträge

Fresh air, rest. Half-upright position. Administration of oxygen may be needed. Refer immediately for medical attention.

ON FROSTBITE: rinse with plenty of water, do NOT remove clothes. Rinse skin with plenty of water or shower. Refer immediately for medical attention.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.

Accidental Release Measures · 2 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.;· Keep unauthorized personnel away.;· Stay upwind, uphill and/or upstream.;· Many gases are heavier than air and will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.).;· Ventilate closed spaces before entering, but only if properly trained and equipped.

· Do not touch or walk through spilled material.;· Stop leak if you can do it without risk.;· If possible, turn leaking containers so that gas escapes rather than liquid.;· Prevent entry into waterways, sewers, basements or confined areas.;· Do not direct water at spill or source of leak.;· Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material.;· Isolate area until gas has dispersed.

First Aid · 3 Einträge

For information on chemical warfare choking agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024);Warning: Effects may be delayed up to 24 hours. Caution is advised.;Signs and Symptoms of Acute Phosgene Exposure: Acute exposure to phosgene may result in severe irritation and burns of the skin, eyes, mucous membranes, and respiratory passages. Cough, dyspnea (shortness of breath), pain in the chest, and severe pulmonary edema may also occur. Cyanosis (blue tint to the skin and mucous membranes) and anxiety may be observed.;Emergency Life-Support Procedures: Acute exposure to phosgene may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination.;Inhalation Exposure:;1. Move victims to fresh air. Emergency personnel should avoid self-exposure to phosgene.;2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support.;3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.;4. RUSH to a health care facility.;Dermal/Eye Exposure:;1. Remove victims from exposure. Emergency personnel should avoid self- exposure to phosgene.;2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support.;3. Remove contaminated clothing as soon as possible.;4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes.;5. Wash exposed skin areas THOROUGHLY with soap and water.;6. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.;7. RUSH to a health care facility.;Ingestion Exposure: No information is available. (EPA, 1998)

General First Aid:;· Call 911 or emergency medical service.;· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.;· Move victim to fresh air if it can be done safely.;· Administer oxygen if breathing is difficult.;· If victim is not breathing:;-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance.;-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).;-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.;· Remove and isolate contaminated clothing and shoes.;· For minor skin contact, avoid spreading material on unaffected skin.;· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.;· For severe burns, immediate medical attention is required.;· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.;· Keep victim calm and warm.;· Keep victim under observation.;· For further assistance, contact your local Poison Control Center.;· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.;Specific First Aid:;· In case of contact with liquefied gas, only medical personnel should attempt thawing frosted parts.

(General first aid procedures);Eye: Irrigate immediately (liquid);Skin: Water flush immediately (liquid);Breathing: Respiratory support

Safe StorageFireproof if in building. Isolated from work area. Separated from incompatible materials. See Chemical Dangers. Cool. Dry. Ventilation along the floor.
Firefighting HazardsProlonged exposure of the cylinders or tank cars to fire or heat may result in their violent rupturing and rocketing.

Toxikologische Informationen

Interactions · 5 Einträge

Dibutyryl cyclic adenosine monophosphate, aminophylline, and B-adrenergic agonist protect against pulmonary edema produced by phosgene.

Early reports of the effectiveness of methenamine in treatment of phosgene poisoning have been disproven. While this compound has been shown to have protective effects when administered prior to exposure the administration post-exposure has no therapeutic benefit.

Drugs disrupting the neutrophil influx associated with the oxidant pathway in phosgene such as aminophylline and terbutaline, ibuprofen and colchicine have been shown to reduce edema in animal studies

A reduction of lung nonprotein sulfhydryl groups through administration of buthionine sulfoximine led to an increased edemagenic effect in the lungs of mice, rats, hamsters, guinea pigs, and rabbits exposed to 0.2 ppm phosgene for 4 hours. Nonprotein sulfhydryl may be important in the normal defense of the lung against the toxic effects of phosgene.

For more Interactions (Complete) data for PHOSGENE (7 total), please visit the HSDB record page.

Target Organs · 2 Einträge

Respiratory

Eyes, skin, respiratory system

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.2(SRC), determined from a structure estimation method(2), indicates that phosgene is expected to have very high mobility in soil(SRC). Volatilization of phosgene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.7X10-2 atm-cu m/mole(3). Phosgene is expected to hydrolyze in moist soil; hydrolysis of a 1% solution of phosgene in water is complete within 20 seconds at 0 °C(4). Phosgene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1420 mm Hg(5). Biodegradation data were not available(SRC, 2007).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.2(SRC), determined from a structure estimation method(2), indicates that phosgene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.7X10-2 atm-cu m/mole(4). Phosgene has been reported to hydrolyze rapidly in seawater(5). Hydrolysis of a 1% solution of phosgene in water is complete within 20 seconds at 0 °C(6). Measured aqueous phase hydrolysis rate constants for phosgene have ranged from 0.29 to 100 sec-1(7). The rapid hydrolysis suggests that bioconcentration will not be an important environmental fate process(SRC). Biodegradation data were not available(SRC, 2007).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phosgene, which has a vapor pressure of 1420 mm Hg at 25 °C(2), is expected to exist solely in the gas phase in the ambient atmosphere. Gas-phase phosgene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 44 years(SRC), calculated from its rate constant of 1.0X10-15 cu cm/molecule-sec at 25 °C(3). Phosgene does not absorb UV radiation at wavelengths >290 nm(4) and therefore would not be subject to direct photolysis by sunlight in the troposphere. Phosgene's hydrolytic half-life in the atmosphere, extrapolating from high temperature data, is 113 yr at sea level, assuming 10 torr of water vapor(5).

Adverse Effects · 1 Eintrag

Lacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.;Chronic Bronchitis - Chronic bronchitis is persistent coughing and production of phlegm for at least 3 months out of the year for at least two successive years. (American Thoracic Society).;Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.;Fibrogenic - Inducing tissue injury and fibrosis (scarring).

Exposure Routes · 3 Einträge

The substance can be absorbed into the body by inhalation.

inhalation, skin and/or eye contact (liquid)

Inhalation is the primary route of exposure to phosgene (CG). Ingestion is unlikely, as phosgene (CG) is a gas at room temperature. Exposure to phosgene (CG) may be irritating to the eyes and skin.

Toxicity Summary · 1 Eintrag

Human exposure in both the general population and occupational setting is primarily by inhalation. ... The primary route of exposure is by inhalation, the gas penetrates into the tissues of the respiratory tract and so only minimal amounts of phosgene are distributed in the body. The very short half-life (0.026 seconds) in aqueous solutions precludes a significant retention of phosgene in the body. ... The hydrolytic products of phosgene, i.e., hydrochloric acid and carbon dioxide, are disposed of by the body through normal physiological processes. Phosgene exerts its toxicity through acylation of proteins, as well as through the production of hydrochloric acid. The amino, hydroxyl and sulfhydryl groups in the protein appear to be the target for acylation leading to marked inhibition of several enzymes related to energy metabolism and a breakdown of the blood:air barrier. In all species studied, the lung is the major target organ. ... In all species the characteristic pathological feature is the delayed clinical manifestation of pulmonary edema, which is dose-dependent. Pathological changes in the terminal bronchioles and alveoli at low concentrations are typical of a pulmonary irritant, whereas at higher exposures pulmonary edema occurs, leading to interference with gas exchange and death. ... Phosgene exposure can result in eye and skin irritation. ... The target organ in humans, as in experimental animals, is the lung. After exposure to phosgene levels between 120 and 1200 mg/cu m-min, three distinct clinical clinicopathological phases have been reported. The initial phase consists of pain in the eyes and throat and tightness in the chest, often with shortness of breath, wheezing, and coughing; hypotension, bradycardia and rarely sinus arrhythmias can occur. The second or latent phase, which is often asymptomatic, can last as long as 24 hr depending upon the level and duration of exposure. In the third phase, pulmonary edema may develop, leading to death in some

Regulatorische Informationen

Regulatory Information · 6 Einträge

Chemical: Carbonic dichloride

Hazard Traits - Neurotoxicity; Respiratory Toxicity;Authoritative List - CA TACs; OEHHA RELs;Report - if used as a fragrance or flavor ingredient

Regulation (EC) No 1107/2009 (amended)

Carbonic dichloride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Carbonic dichloride are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 02-08-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/20452;Status: Active Update: 08-11-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/10463

Phosgene: HSNO Approval: HSR001066 Approved with controls

RCRA Requirements · 1 Eintrag

P095; As stipulated in 40 CFR 261.33, when phosgene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

Atmospheric Standards · 2 Einträge

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Phosgene is produced, as an intermediate or a final product, by process units covered under this subpart.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Phosgene is included on this list.

CERCLA Reportable Quantities · 2 Einträge

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Phosgene is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 10 lbs.

Clean Water Act Requirements · 1 Eintrag

Phosgene is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.

DHS Chemicals of Interest (COI) · 6 Einträge

Phosgene

1.00

500

0.17

15

Toxic chemical that can be released at a facility.

Sicherheitsdaten

F
3-21
OEB
C
OEL
TWA: 0.1 ppm (0.4 mg/m3), Ceiling: 0.2 ppm (0.8 mg/m3) [15-minute]
wgk
2
IDLA
2 ppm
tsca
TSCA listed

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 3 Einträge

Phosgene is a highly reactive gas capable of damaging a variety of biological macromolecules in an oxidant-like fashion. This activity potentially results from at least two separate chemical reactions: acylation and hydrolysis. Acylation, the more important and rapid mechanism, results from the reaction of phosgene with nucleophilic moieties, such as the amino, hydroxyl, and sulfhydryl groups of tissue macromolecules. Acylation causes destruction of proteins and lipids, irreversible alterations of membrane structures, and disruption of enzyme and other cell functions. Exposure to phosgene depletes lung nucleophiles, particularly glutathione, and restoration of glutathione seems to protect against phosgene-induced injury. For several days after acute phosgene exposure, tissue levels of antioxidant enzymes, such as glutathione reductase and superoxide dismutase, increase as part of the lungs' response to injury. In addition to acylation, phosgene is hydrolyzed to HCl ... The formation of HCl occurs on moist membranes and may cause irritation and tissue damage. Because of the limited water solubility of phosgene, it is unlikely that large quantities of HCl could result from the exposure of biological tissues. However, small amounts do form and may contact moist membranes of the eye, nasopharynx, and respiratory tract. Hydrolysis to HCl is the probable cause of immediate inflammation and discomfort after phosgene exposure at concentrations greater than 3 ppm (>12 mg/cu m). Pulmonary cellular glycolysis and oxygen uptake following phosgene exposure are depressed and, thus, leads to a corresponding decrease in the levels of intracellular adenosine triphosphate and cyclic adenosine monophosphate. This is associated with increased water uptake by epithelial, interstitial, and endothelial cells. The semipermeability of the blood-air barrier becomes gradually compromised as a result of fluid entering the interstitial and alveolar spaces. Later, the blood-air barrier disrupts,

The pathology of phosgene poisoning is mainly due to its acylating properties and not a result of hydrochloric acid generation upon hydrolysis, although hydrochloric acid production may play a minor role. The production of pulmonary edema following phosgene exposure has been correlated with reductions in pulmonary ATP levels and sodium-potassium ATPase activity, as well as inhibition of other pulmonary enzymes. The role of the nervous system in the toxicity of phosgene is considered to be a nonspecific effect of irritant gases.

Phosgene is only slightly soluble in water; the small amount of phosgene which dissolves is immediately hydrolyzed to CO2 and HCl. The concentration of HCl produced from a lethal dose of phosgene is </= 10R-10 M, which can be easily buffered by the lung tissue. The inhalation toxicity of phosgene is enhanced by its low water solubility, which allows it to penetrate further into the lungs than can more soluble gases. When phosgene reaches the alveolar region it reacts with NH2-, SH- or OH-groups of the bloood-air barrier. The acylating reaction of phosgene occurs much more rapidly than the reaction of phosgene with water.

Biological Half-LifeNo reports found; [TDR, p. 1030]
Metabolism/Metabolites · 4 Einträge

Cysteine inhibited in vitro covalent binding of chloroform to liver microsomal protein and trapped a reactive metabolite, presumably phosgene, as 2-oxothiazolidine-4-carboxylic acid. This suggests that the carbon-hydrogen bond of chloroform is oxidized by a cytochrome P450 monooxygenase to produce trichloromethanol, which spontaneously dehydrochlorinates to yield phosgene.

Phosgene is formed during NADPH and oxygen dependent microsomal oxidation of /carbon tetrachloride/.

Phosgene reacts rapidly with water, but more rapidly with certain chemical groups found in tissue macromolecules, such as free amines and sulfhydryls. Because of its high reactivity, it is doubtful that any unreacted phosgene will enter the general circulation even after exposure to high concentrations of the gas.

... Sensitivity to chloroform correlates with the capacity of the kidney to metabolize chloroform to the toxic metabolite phosgene. ... Kidney homogenates of sensitive male DBA/2J mice metabolized chloroform to phosgene more rapidly than did the less sensitive C57BL/6J mice. Similarly, kidney homogenates from male mice, which are sensitive to chloroform induced nephrotoxicity, metabolized chloroform to phosgene at nearly an order of magnitude more rapidly than did those from female mice. Treatment of female mice with testosterone, however, reversed this trend. Cytochrome P450 in the microsomal and mitochondrial fraction of the kidney appeared to catalyze the metabolism of chloroform to phosgene.

MeSH Pharmacological ClassificationChemicals that are used to cause the disturbance, disease, or death of humans during WARFARE.
Absorption, Distribution and Excretion · 4 Einträge

Rats were exposed to 0.1 - 1.0 ppm 14C-phosgene (0.4 - 4.1 mg/cu m) for 0.5 to 4 hr and tissue distribution of carbon-14 was investigated. Phosgene adduct concentrations (measured as nmol carbon-14/g dry weight) were highest in the lung, trachea, nasopharynx and blood, and were also highly concentrated in constituents of nasal and broncheolar lavage fluids. Lung tissue carbon-14 was distributed in lipid, macromolecule, and water-soluble fractions in a manner which was proportional to the weight contributed by each fraction.

Rabbits, guinea pigs, rats, hamsters and mice were exposed simultaneously to 1.6 ppm 14C-phosgene (6.6 mg/cu m) for 3 min in a closed Plexiglas chamber. Mean lung concentrations of carbon-14 in these animals immediately following exposure were 3.15, 2.50, 5.33, 5.05 and 11.13 nmoles/g wet weight, respectively. Blood carbon-14 ranged from 2.5% of lung concentrations in rabbits to 5.9% in mice. The nasopharyngeal fraction of total respiratory tract carbon-14 was higher in rabbits and guinea pigs (0.46 - 0.50) than in the other species (0.22 - 0.36). Tracheal carbon-14 was always about 3% of total respiratory tract carbon-14. Liver carbon-14 was about 1% of lung concentrations. Tissue binding of phosgene was shown by a large percentage of carbon-14 in trichloroacetic acid precipitates of tissue and by the presence of carbon-14 in lungs (20% of initial) 3 days post exposure.

The gas penetrates into the tissues of respiratory tract and to some extent is absorbed by the lung. ... Hydrochloric acid and carbon dioxide produced by hydrolysis of phosgene are excreted largely by kidney and lung, respectively.

Rats, mice, hamsters, guinea pigs and rabbits were exposed by inhalation to 14C-phosgene at 1.6 ppm for 3 minutes. Carbon-14 was detected at very low levels in blood and liver samples of all animals.

Verwendung und Herstellung

Uses · 6 Einträge

Phosgene is a widely used chemical intermediate, primarily manufactured in the preparation of many organic chemicals. Phosgene is used for the synthesis of isocyanate-based polymers, carbonic acid esters, and acid chlorides. It is also used in the manufacture of dyestuffs, some insecticides, and pharmaceuticals and in metallurgy. In the past, phosgene was used as a chemical warfare agent (in WWI and WWII).

Used as an intermediate in the synthesis of many organic chemicals; also produced from thermal decomposition or photodecomposition of chlorinated hydrocarbons--the heat or UV light of welding can generate phosgene from degreasing solvents; [ACGIH]

Welding [Category: Weld];Petroleum Production and Refining [Category: Industry];Firefighting [Category: Other];Burning Synthetic Polymers [Category: Burn]

Phosgene is primarily used in the polyurethane industry for the production of polymeric isocyanates. Phosgene is also used in the polycarbonate industry and in the manufacture of carbamates and related pesticides, dyes, perfumes, pharmaceuticals, and isocyanates.

For the prepn of many organic chemicals; as a war gas

INTERMEDIATE, CARBONYLATING AGENT

Impurities · 2 Einträge

Chlorine (free), max 0.1%; hydrochloric acid, max 0.2%

Undesirable impurities in the production of phosgenes are sulfur chlorides

U.S. Production · 6 Einträge

2023: 250,000,000 - <400,000,000 lb;2022: 250,000,000 - <400,000,000 lb;2021: 250,000,000 - <400,000,000 lb;2020: 250,000,000 - <400,000,000 lb

(1972) 3.21X10+11 GRAMS

(1975) 3.6X10+11 GRAMS

5.5X10+11 g

Phosgene is produced in large quantities (over 2,000 million pounds in 1987)

For more U.S. Production (Complete) data for PHOSGENE (7 total), please visit the HSDB record page.

Consumption Patterns · 5 Einträge

62% IS USED TO PRODUCE TOLUENE DIISOCYANATE; 24% TO PRODUCE POLYMETHYLENE POLYPHENYLISOCYANATE; 4% TO MAKE POLYCARBONATE RESINS; 10% IN MISC APPLICATIONS (1973)

TOLUENE DI-ISOCYANATE (52%); MDI AND POLYMER ISOCYANATES (35%); POLYCARBONATE RESIN (6%); OTHER ISOCYANATES, SPECIALTIES AGRICULTURAL AND MISC USES (6%) (1984)

CHEMICAL PROFILE: Phosgene. Toluene diisocyanate, 45%; MDI and polymeric isocyanates, 35%; polycarbonate resins, 10%; miscellaneous, including specialty isocyanates, chloroformates and ag chemicals, 10%. (1987)

CHEMICAL PROFILE: Phosgene. Demand: 1986: 1,900 million lb; 1987: 2,050 million lb; 1991 /projected/: 2,250 million lb.

For more Consumption Patterns (Complete) data for PHOSGENE (12 total), please visit the HSDB record page.

Consumer UsesIntermediate
Industry UsesIntermediate
Anwendungen · 2 Einträge

BeschreibungPhosgene 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.

VerwendenPHOSGENE 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.

Darstellung · 1 Eintrag

synthetischePhosgene is prepared by the reaction of carbon monoxide and chlorine. The mixture of these gases is passed over activated carbon: CO + Cl2 → COCl2 Alternatively, phosgene can be made by reacting carbon monoxide with nitrosyl chloride, or by treating carbon tetrachloride with oleum.

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Ergänzende Hinweise

DefinitionChEBI: An acyl chloride obtained by substitution of both hydrogens of formaldehyde by chlorine.

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