ChemicalBook > Product Catalog >Organic Chemistry >Alcohols,Phenols,Phenol alcohols >Acyclic alcohols >ketene

ketene

ketene Structure
CAS No.
463-51-4
Chemical Name:
ketene
Synonyms
Keten;ethenone;carbometene;Ethen-1-one;Carbomethene;ketene ISO 9001:2015 REACH
CBNumber:
CB9934768
Molecular Formula:
C2H2O
Molecular Weight:
42.04
MOL File:
463-51-4.mol
MSDS File:
SDS
Modify Date:
2024/4/15 9:04:06

ketene Properties

Melting point -150°
Boiling point bp -56°
Density 0.6600
refractive index 1.3040 (estimate)
form Gas
Exposure limits TLV-TWA 0.9 mg/m3 (0.5 ppm); STEL 3.0 mg/m3 (1.5 ppm) (ACGIH); IDLH 50 ppm (NIOSH).
EPA Substance Registry System Ketene (463-51-4)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS02,GHS05,GHS06
Signal word  Danger
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
RIDADR  1955
OEB C
OEL TWA: 0.5 ppm (0.9 mg/m3), STEL: 1.5 ppm (3 mg/m3)
HazardClass  2.3
IDLA 5 ppm

ketene Chemical Properties,Uses,Production

Chemical Properties

Colorless gas with a sharp penetrating odor;liquefies at -56°C (-68.8°F); solidifies at-151°C (-239.8°F); soluble in alcohol andacetone, decomposed by water.

Uses

For the conversion of higher acids into their anhydrides; for acetylation in the manufacture of cellulose acetate and aspirin.

Production Methods

Ketene may be prepared also by pyrolysis of acetic anhydride or phenyl acetate or diketene. Other sources are quite unsatisfactory from a standpoint of yield. Small quantities may be made conveniently by heating acetone in a “ketene lamp.” This is a glass apparatus containing a Nichrome filament, heated electrically to red heat. Larger amounts are made by passing acetone or acetic acid through a tube at 700 °C. A very brief contact time is required, so that much of the acetone is undecomposed and has to be condensed and recycled. Also, it is imperative that the reaction tube be of inert material such as porcelain, glass, quartz, copper or stainless steel. A copper tube, if used, should be protected from oxidation by an iron sheath. Inert packing may be used (glass, vanadium pentoxide, porcelain), but just as good yields are obtained with empty tubes. No catalyst is known which accelerates this decomposition at significantly lower temperatures.

Health Hazard

Ketene is a highly toxic gas. It causes severeirritation to the eyes, nose, throat, and skin.Exposure to 10–15 ppm for several minutescan injure the respiratory tract. It causespulmonary edema. A 30-minute exposure to23 ppm was lethal to mice and a 10-minuteexposure to 200 and 750 ppm caused deathto monkeys and cats.

Fire Hazard

Ketene in its gaseous state should be flammable and explosive in air. The pure compound, however, polymerizes readily and cannot be stored as a gas. Its flash point and LEL and UEL values are not reported. It can react violently with oxidizers and many organic compounds. Its small size and the olefinic unsaturation impart further reactivity to the molecule.

Purification Methods

Ketene is prepared by pyrolysis of acetic anhydride. Purify it by passing through a trap at -75o and collecting in a liquid-nitrogen-cooled trap. Ethylene is removed by evacuating the ethylene in an isopentane-liquid-nitrogen slush pack at -160o. Store it at room temperature in a suitable container in the dark or better at -80o, but do not store it under pressure as it may EXPLODE. It is a strong IRRITANT when inhaled and is as poisonous as phosgene. See diketene in “Heterocyclic Compounds”, Chapter 4. [Hurd Org Synth Coll Vol I 330 1941, Andreades & Carlson Org Synth Coll Vol V 679 1973.]

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