Basic information
- Standard SMILES
C=C=O- InChIKey
CCGKOQOJPYTBIH-UHFFFAOYSA-N- Molecular formula
- C2H2O
- Average molar mass
- 42.04 g/mol
- Monoisotopic mass
- 42.01056468
Overview
Ketene appears as a colorless highly reactive gas with a penetrating odor. mp: -150 °C, bp: -56 °C. Reacts violently with water. Soluble in diethyl ether and acetone. Severely irritates the eyes, the skin and the respiratory tract. Used is the manufacture of acetic anhydride, sorbic acid, cinnamic acids, chloroacetyl chloride and other materials. Readily polymerizes and cannot be shipped or stored. Is obtained instead as needed from diketene. DIKETENE (CAS: 674-82-8; Formula: C4H2O2 ) is a colorless liquid with a pungent odor. mp: -6.5 °C; bp: 127 °C. Density 1.08 g/cm3. Reacts violently with water. Is obtained from the dimerization of ketene and can be stored and transported under refrigeration. A severe lachrymator (irritates the eyes, the respiratory tract, and the skin as well). Depolymerizes at 650 °C to give ketene.
Names & identifiers
- Preferred name
- Ketene
- IUPAC
- ethenone
- English name
- ketene
- Molecular formula
- C2H2O
- Molecular weight
- 42.04
Names & synonyms
Show more names
Database identifiers
- CAS
12071-23-7、463-51-4- PubChem CID
- 10038
- DTXSID
DTXSID1052113- ChEBI
CHEBI:48003- UNII
- LEP3SM032A
- EC Number
- 207-336-9
- Nikkaji
- J2.590I
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 3
- Formal charge
- 0
- Complexity
- 25.8
Experimental & physicochemical properties
Chemical Classes
Toxic Gases & Vapors -> Other Toxic Gases & Vapors
Flammable agents - 3rd degree
Odor
PENETRATING ODOR
Penetrating odor.
Color/Form
COLORLESS GAS
Colorless gas.
Solubility
Reacts with water (NIOSH, 2024)
SLIGHTLY SOL IN ETHER
Fairly sol in acetone
Solubility in water: reaction
Reacts
Flash Point
Flammable gas
NA (Gas)
Boiling Point
-69 °F at 760 mmHg (NIOSH, 2024)
-56 °C
-56 °C
-49.8 °C @760 [mm Hg]
-69 °F
Melting Point
-238 °F (NIOSH, 2024)
-150 °C
-150 °C
-151 °C
-238 °F
Vapor Density
1.45 (NIOSH, 2024) - Heavier than air; will sink (Relative to Air)
1.45 (AIR= 1)
Relative vapor density (air = 1): 1.4
Vapor Pressure
greater than 1 atm (NIOSH, 2024)
1.04X10+4 mm Hg @ 25 °C /calculated from experimentally derived coefficients/
750 [mm Hg] @-50 °C
>1 atm
Physicochemical properties
- Melting point
- -150 ° · -150°
- Boiling point
- -56 ° · bp -56°
- Density
- 0.66 · 0.6600
- refractive index
- 1.304 · 1.3040 (estimate)
- form
- Gas
- Exposure limits
- 0.05 ppmOSHA:PEL-TWA · ACGIH:TLV-CEILING 0.05ppmOSHA:PEL-TWA 0.5 ppm (0.9 mg/m3)NIOSH:REL-TWA 0.5 ppm; REL-STEL 1.5 ppm
- FDA UNII
- 3 SM032A · LEP3SM032A
- EPA Substance Registry System
- Ketene (463-51-4)
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 315 · H315-H220-H330-H335-H318
- Precautionary statements
- 264 · P264-P280-P302+P352-P321-P332+P313-P362-P280-P305+P351+P338-P310-P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501-P210-P377-P381-P403
- RIDADR
- 1955 · 1955
- OEB
- C
- OEL
- 0.5 ppm · TWA: 0.5 ppm (0.9 mg/m3), STEL: 1.5 ppm (3 mg/m3)
- TSCA
- TSCA listed
- HazardClass
- 2.3 · 2.3
- Hazardous Substances Data
- 463 · 463-51-4(Hazardous Substances Data)
- IDLA
- 5 ppm · 5 ppm
Safety & regulation
GHS classification
GHS Classification
Danger
H220 (100%): Extremely flammable gas [Danger Flammable gases]
P203, P210, P222, P260, P261, P264, P264+P265, P271, P280, P284, P302+P352, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P332+P317, P362+P364, P377, P381, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 111 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H220: Extremely flammable gas [Danger Flammable gases]
Hazard information
Regulatory Information
Chemical: Ethenone
Ketene: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Excerpt from ERG Guide 131 [Flammable Liquids - Toxic; polymerization hazard]:
Extremely flammable. Gas/air mixtures are explosive.
Hazards Summary
TLV Basis is pulmonary edema, lung damage, and eye irritation. Animal studies show that ketene is an inhalation irritant with toxicity similar to that of phosgene. [ACGIH] A severe irritant of the skin, eyes, and respiratory tract; [CAMEO] Reacts violently with water producing acetic acid; A skin, eye, and respiratory tract irritant; Inhalation may cause pulmonary edema; Chronic or repeated exposure may cause emphysema and fibrosis; [ICSC] Causes acute pulmonary edema, other changes in lungs, thorax, or respiration, convulsions, and dyspnea in lethal-concentration inhalation studies of rodents; [RTECS]
OSHA Standards
Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 0.5 ppm (0.9 mg/cu m).
Vacated 1989 OSHA PEL TWA 0.5 ppm (0.9 mg/cu m); STEL 1.5 ppm (3 mg/cu m) is still enforced in some states.
Atmospheric Standards
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. Ketene is produced, as an intermediate or a final product, by process units covered under this subpart.
Safety & protection
Fire Fighting
Excerpt from ERG Guide 131 [Flammable Liquids - Toxic; polymerization hazard]:
Use powder, carbon dioxide. NO water. In case of fire: keep cylinder cool by spraying with water. NO direct contact with water.
First Aid Measures
Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
First Aid
Excerpt from NIOSH Pocket Guide for Ketene:
(General first aid procedures)
Storage Conditions
...CANNOT BE...STORED IN A GASEOUS STATE.
Protect containers against physical damage by shock. Outdoor or detached storage is preferable. For indoor storage, use standard combustible liquid storeroom or cabinet.
Cleanup Methods
PERSONS NOT WEARING PROTECTIVE EQUIPMENT AND CLOTHING SHOULD BE RESTRICTED FROM AREAS OF LEAKS UNTIL CLEANUP HAS BEEN COMPLETED. IF KETENE IS LEAKED, THE FOLLOWING STEPS SHOULD BE TAKEN: 1. REMOVE ALL IGNITION SOURCES. 2. VENTILATE THE AREA OF LEAK. 3. STOP FLOW OF GAS. DISPOSAL METHODS: KETENE MAY BE DISPOSED OF BY BURNING AT A SAFE LOCATION OR IN A SUITABLE COMBUSTION CHAMBER.
Preventive Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Toxicology
Exposure Routes
The substance can be absorbed into the body by inhalation.
inhalation, skin and/or eye contact
Signs and Symptoms
Cough. Shortness of breath. Symptoms may be delayed.
Redness.
Redness. Pain.
irritation eyes, skin, nose, throat, respiratory system; pulmonary edema
Human Toxicity Excerpts
SEVERE PULMONARY IRRITANT CAUSING PULMONARY EDEMA IF INHALED.
STRONG IRRITANT TO SKIN & MUCOUS MEMBRANES.
TOXIC BY ... INHALATION ... .
KETENE IS ONE OF THE MOST HIGHLY IRRITANT GASES TO THE RESP TRACT; ITS TOXICITY APPEARS TO BE OF THE SAME ORDER OF MAGNITUDE AS THAT OF PHOSGENE AND ALSO RESEMBLES PHOSGENE IN ITS DELAYED ACTION ON THE RESPIRATORY SYSTEM.
For more Human Toxicity Excerpts (Complete) data for KETENE (8 total), please visit the HSDB record page.
Non-Human Toxicity Excerpts
/IN MICE AND RATS/ CONCN OF OVER 100 PPM ... PROVED FATAL WITH DEATH OCCURRING RAPIDLY WITH ... MARKED EYE, NOSE, THROAT, & PULMONARY IRRITATION. AUTOPSIES SHOWED THAT THERE WAS DILATATION OF THE RIGHT HEART & MAJOR DAMAGE TO ALVEOLAR WALLS WITH PULMONARY EDEMA.
... REPEATED INHALATIONS AT 1 PPM IN THE RAT, CAT, & MONKEY ... SHOWED EVIDENCE OF LUNG DAMAGE ... INTERSTITIAL FIBROSIS, CELLULAR INFILTRATION, ATELECTASIS, & EMPHYSEMA /ON AUTOPSY/.
EXPOSURE OF MONKEYS TO 23 PPM IN AIR FOR FOUR HOURS CAUSED THE ANIMALS TO RUB THEIR EYES, COUGH, & BECOME LETHARGIC.
/IN GUINEA PIGS/ CONCN OF OVER 100 PPM ... PROVED FATAL WITH DEATH OCCURRING RAPIDLY WITH ... MARKED EYE, NOSE, THROAT, & PULMONARY IRRITATION. AUTOPSIES SHOWED THAT THERE WAS DILATATION OF THE RIGHT HEART & MAJOR DAMAGE TO ALVEOLAR WALLS WITH PULMONARY EDEMA.
Regulatory information
Atmospheric Standards
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. Ketene is produced, as an intermediate or a final product, by process units covered under this subpart.
Safety data
- OEB
- C
- OEL
- TWA: 0.5 ppm (0.9 mg/m3), STEL: 1.5 ppm (3 mg/m3)
- IDLA
- 5 ppm
- tsca
- TSCA listed
- ridadr
- 1955
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS06
- hazard_class
- 2.3
- Hazard statements
- H315-H220-H330-H335-H318
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P280-P305+P351+P338-P310-P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501-P210-P377-P381-P403
- Hazardous Substances Data
- 463-51-4(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used in the synthesis of acetic anhydride and other organic chemicals; [ACGIH] Polymerizes readily and cannot be stored. Obtained from diketene; [CAMEO]
CONVERSION OF HIGHER ACIDS INTO THEIR ANHYDRIDES
ACETYLATION IN MFR OF CELLULOSE ACETATE & ASPIRIN
PRINCIPALLY CHEM INT FOR ACETIC ANHYDRIDE FROM ACETIC ACID; FOR DEHYDROACETIC ACID AND ACETOACETIC ESTERS; FOR ACETOACETANILIDE & N,N-DIALKYLACETOACETAMIDES
Acetylating agent, generally reacting with compounds having an active hydrogen atom; reacts with ammonia to give acetamide. Starting point for making various commercially important products, especially acetic anhydride and acetate esters.
Methods of Manufacturing
BY THERMAL DECOMPOSITION OF ACETONE, DIKETENE OR ACETIC ANHYDRIDE.
PYROLYSIS OF ACETONE OR ACETIC ACID BY PASSING ITS VAPOR THROUGH A TUBE AT 500-600 °C.
Applications
DescriptionKetene is a flammable, colorless gas with asharp, disagreeable odor. Molecular weight = 42.04;Boiling point = 054.4℃; Freezing/Melting point =-148.3℃; Relative vapor density (air = 1): 1.45; Vaporpressure =
UsesOrganic chemical syntheses; conversion of higher acids into their anhydrides; for acetylation in the manufacture of cellulose acetate and aspirin
UsesKetene is used as an acetylating agent inthe production of cellulose acetate, aspirin,acetic anhydride, and in various organicsyntheses.
UsesFor the conversion of higher acids into their anhydrides; for acetylation in the manufacture of cellulose acetate and aspirin.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers6 total
Additional notes
DefinitionChEBI: Ethenone is a ketene.
Related reactions
Linked notes
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