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Ketene

HCID 10038
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Basic information

CAS
12071-23-7
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

EthenoneKETENECarbometheneKeto-ethylene463-51-4LEP3SM032ADTXSID1052113CHEBI:48003KETOETHYLENERefChem:794269DTXCID3030682CHEBI:48002
Show more names
carbometeneEthen-1-oneketene ISO 9001:2015 REACH
207-336-9EthylenoneKETEN12071-23-7HSDB 633EINECS 207-336-9UNII-LEP3SM032Aoxoethylene

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 · 2 items

Toxic Gases & Vapors -> Other Toxic Gases & Vapors

Flammable agents - 3rd degree

SpringerMaterials PropertiesCoriolis coupling
Odor · 2 items

PENETRATING ODOR

Penetrating odor.

TasteDISAGREEABLE TASTE
Density1.45(relative gas density)
Color/Form · 2 items

COLORLESS GAS

Colorless gas.

Solubility · 5 items

Reacts with water (NIOSH, 2024)

SLIGHTLY SOL IN ETHER

Fairly sol in acetone

Solubility in water: reaction

Reacts

Flash Point · 2 items

Flammable gas

NA (Gas)

Boiling Point · 5 items

-69 °F at 760 mmHg (NIOSH, 2024)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

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 · 3 items

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.)

DOT LabelPoison Inhalation Hazard Flammable Liquid
Fire Hazards · 2 items

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic; polymerization hazard]:

Extremely flammable. Gas/air mixtures are explosive.

Health HazardsExcerpt from NIOSH Pocket Guide for Ketene:
Hazards Summary · 1 item

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]

Chemistry & industry

Uses & manufacturing

Uses · 5 items

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 · 2 items

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.

General Manufacturing InformationEthenone: ACTIVE
Applications · 4 items

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

Related reactions

49 records
New reaction record
HRID 64739 reaction equation
HRID 64739As reactantuspto-grants-1986_09
HRID 64740 reaction equation
HRID 64740As reactantuspto-grants-1986_09
HRID 64741 reaction equation
HRID 64741As productuspto-grants-1986_09
HRID 121068 reaction equation
HRID 121068As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 123836 reaction equation
HRID 123836As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 127734 reaction equation
HRID 127734As reactantuspto-grants-1981_03
HRID 151544 reaction equation
HRID 151544As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 192488 reaction equation
HRID 192488As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Page 1 of 7

Compound notes

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-56 °C

-56 °C

-49.8 °C @760 [mm Hg]

-69 °F

Melting Point · 5 items

-238 °F (NIOSH, 2024)

-150 °C

-150 °C

-151 °C

-238 °F

Vapor Density · 3 items

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 · 4 items

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
Reactive GroupKetones
Reactivity AlertsHighly Flammable
OSHA Standards · 2 items

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.

Reactivity ProfileKETENE is extremely flammable. Mixtures with air are explosive. Reacts violently with water; reacts vigorously with alcohols, ammonia. Readily polymerizes and cannot be shipped or stored. Is obtained instead as needed from diketene.
Atmospheric Standards · 1 item

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.

Chemical DangersThe substance may readily polymerize. Reacts violently with many organic compounds. Reacts with water. This produces acetic acid. Decomposes in alcohol and ammonia.
Flammable LimitsFlammable Gas

Safety & protection

Fire Fighting · 2 items

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 · 3 items

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 · 2 items

Excerpt from NIOSH Pocket Guide for Ketene:

(General first aid procedures)

Safe StorageThe substance cannot be stored or shipped.
Storage Conditions · 2 items

...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 · 1 item

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.

Nonfire Spill ResponseExcerpt from ERG Guide 131 [Flammable Liquids - Toxic; polymerization hazard]:
Spillage DisposalEvacuate danger area! Consult an expert! Ventilation. Personal protection: gas-tight chemical protection suit including self-contained breathing apparatus.
Preventive Measures · 1 item

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.

Isolation and EvacuationExcerpt from ERG Guide 131 [Flammable Liquids - Toxic; polymerization hazard]:
Eye PreventionWear safety goggles or eye protection in combination with breathing protection.
Fire PreventionNO open flames, NO sparks and NO smoking. Closed system, ventilation, explosion-proof electrical equipment and lighting.

Toxicology

Target OrgansEyes, skin, respiratory system
Adverse EffectsToxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.
Exposure Routes · 2 items

The substance can be absorbed into the body by inhalation.

inhalation, skin and/or eye contact

Signs and Symptoms · 4 items

Cough. Shortness of breath. Symptoms may be delayed.

Redness.

Redness. Pain.

irritation eyes, skin, nose, throat, respiratory system; pulmonary edema

Human Toxicity Excerpts · 5 items

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 · 4 items

/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.

Probable Routes of Human ExposureInhalation, eye and skin contact.
Toxicity DataLCLo (mouse) = 23 ppm/30min
Non-Human Toxicity ValuesLC50 MOUSE INHALATION 17 PPM/10 MIN

Regulatory information

Atmospheric Standards · 1 item

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)
PIPE
Silica gel
Carbon monoxide
Triethyl phosphate
4-Chlorobenzaldehyde
Flow Cell
methylketene
Phenoxatellurin

Downstream products

Acetyl keteneLinalyl acetateButyric anhydrideAcetoacetamideSorbic acidAcetylacetoneMachetteAcetic anhydrideHEXANOIC ANHYDRIDEAcephateEthyl acetateMethyl acrylateWL 108477Citric acid2,2,6-Trimethyl-4H-1,3-dioxin-4-oneDichloroacetyl chloride

Additional notes

DefinitionChEBI: Ethenone is a ketene.