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Acetyl ketene

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Acetyl ketene

EINECS 211-617-1
CAS No. 674-82-8 Density 1.10 g/cm3
Solubility soluble in water and organic solvents Melting Point -7.5 °C
Formula C4H4O2 Boiling Point 127.4 °C at 760 mmHg
Molecular Weight 84.07 Flash Point 97.9 °C
Transport Information UN 2929 6.1/PG 2 Appearance colorless liquid
Safety 3-36/37-33-24/25-23-16 Risk Codes 10-20-40
Molecular Structure Molecular Structure of 674-82-8 (2-Oxetanone,4-methylene-) Hazard Symbols HarmfulXn

3-Butenoicacid, 3-hydroxy-, b-lactone (6CI,7CI);4-Methylene-2-oxetanone;Diketene;Ethenone, dimer;Ketene dimer;NSC 93783;


Acetyl ketene Consensus Reports

Reported in EPA TSCA Inventory.

Acetyl ketene Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid, Poison

Acetyl ketene Specification

The Ketene dimer with CAS registry number of 674-82-8 is also known as 2-Oxetanone, 4-methylene-. The IUPAC name is 4-Methylideneoxetan-2-one. It belongs to product categories of Pharmaceutical Intermediates; Aromatic amine products. Its EINECS registry number is 211-617-1. In addition, the formula is C4H4O2 and the molecular weight is 84.07. This chemical is a colorless liquid and should be stored in sealed containers in cool, dry place and away from oxidizing agents, acids, bases and amines.

Physical properties about Ketene dimer are: (1)ACD/LogP: 0.27; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.27; (4)ACD/LogD (pH 7.4): 0.27; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 33.28; (8)ACD/KOC (pH 7.4): 33.28; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.449; (13)Molar Refractivity: 19.91 cm3; (14)Molar Volume: 74.1 cm3; (15)Surface Tension: 28.5 dyne/cm; (16)Density: 1.13 g/cm3; (17)Flash Point: 97.9 °C; (18)Enthalpy of Vaporization: 36.8 kJ/mol; (19)Boiling Point: 127.4 °C at 760 mmHg; (20)Vapour Pressure: 11.1 mmHg at 25 °C.

Preparation of Ketene dimer: it is prepared by thermal decomposition by acetic acid, acetone, acetic anhydride and acetate. Acetic pyrolysises at 750-780 °C in the presence of triethyl phosphate to get ketene, then polymerizes at 8-10 °C to get the product.


Uses of Ketene dimer: it is used to produce N-acetoacetyl-N'-cyclohexylsulfamide by reaction with cyclohexyl-sulfamide. The reaction occurs with reagent aq.NaOH at ambient temperature for 2 hours. The yield is about 36%. This chemical is also used as raw materials of fine chemicals, dyes, pharmaceuticals, pesticides, food and feed additives, additives and others.

Ketene dimer is used to produce N-acetoacetyl-N'-cyclohexylsulfamide by reaction with cyclohexyl-sulfamide.

When you are using this chemical, please be cautious about it. As a chemical, it is flammable and harmful by inhalation. There is limited evidence of a carcinogenic effect. During using it, wear suitable protective clothing and gloves. Avoid contact with skin and eyes. What's more, take precautionary measures against static discharges and do not breathe gas/fumes/vapour/spray. After using it, keep it in a cool place and keep away from sources of ignition.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C=C1CC(=O)O1
2. InChI: InChI=1S/C4H4O2/c1-3-2-4(5)6-3/h1-2H2

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LC50 inhalation 3gm/m3/2H (3000mg/m3)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 301, 1986.
guinea pig LDLo skin 10mL/kg (10mL/kg)   Kodak Company Reports. Vol. 21MAY1971,
mouse LDLo oral 800mg/kg (800mg/kg)   Kodak Company Reports. Vol. 21MAY1971,
rabbit LD50 skin 2830uL/kg (2.83mL/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.
rat LCLo inhalation 20000ppm/1H (20000ppm)   Industrial Hygiene Foundation of America, Chemical and Toxicological Series, Bulletin. Vol. 6, Pg. 1, 1967.
rat LD50 oral 560uL/kg (0.56mL/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.

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