Ketene

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  • Identifiers

    CAS number
    463-51-4

    Molecular formula
    C2H2O

    SMILES
    C=C=O

    Safety labels

    Flammable
    Flammable

    Corrosive
    Corrosive

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 73.14%
    Pungent 50.07%
    Sharp 33.09%
    Burnt 23.29%
    Bitter 20.17%
    Sour 18.49%
    Fruity 16.9%
    Ethereal 16.77%
    Radish 15.98%
    Almond 15.93%

     

    Flavor
    Odorless 51.5%
    Bitter 42.19%
    Pungent 37.64%
    Mustard 33.67%
    Sulfur 26.53%
    Formyl 25.55%
    Rotten 23.91%
    Vinegar 23.29%
    Cherry 21.33%
    Decomposing cabbage 20.04%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.8

    pKa est.
    9.34 (weak base)

    Molecular weight
    42.04 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Melting point expt.

    • -238 °F (NIOSH, 2024)
    • -150 °C
    • -238 °F

    Boiling point

    • -69 °F at 760 mmHg (NIOSH, 2024)
    • -56 °C
    • -69 °F

    Flash point

    • -54.27 ˚C est.
    • Flammable gas
    • NA (Gas)

    Solubility expt.

    • Reacts with water (NIOSH, 2024)
    • SLIGHTLY SOL IN ETHER
    • Fairly sol in acetone
    • Solubility in water: reaction
    • Reacts

  • Synonyms

    • KETENE
    • Ethenone
    • Carbomethene
    • Ethylenone
    • Keto-ethylene
    • 463-51-4
    • KETEN
    • 12071-23-7
    • HSDB 633
    • EINECS 207-336-9
    • LEP3SM032A
    • KETENE [HSDB]
    • KETENE [MI]
    • DTXSID1052113
    • CHEBI:48003
    • UNII-LEP3SM032A
    • ketenes
    • oxoethylene
    • Ethylenone #
    • Ketene; (Carbomethene, Ethenone)
    • Ethenone (9CI)
    • KETOETHYLENE
    • Carbon oxide (c2o)
    • CH2CO
    • Ketene (ACGIH:OSHA)
    • KETENE (C2H2O)
    • DTXCID3030682
    • CHEBI:48002
    • DS-002706
    • NS00020820
    • A804568
    • Q421032
    • 207-336-9

  • Applications

    Ketene (CAS 463-51-4) is a highly reactive acetylating intermediate used as a key industrial building block. It acts as an efficient acetylating reagent by reacting with alcohols to form acetates, and serves as a precursor for acylation reagents entering coatings, adhesives, and polymer formulations. Ketene can be generated or consumed in situ in processes such as vinyl acetate production and related acetylation steps, and its reaction pathways provide acetyl-containing building blocks such as acetates and related derivatives. As a versatile synthetic intermediate, ketene is used to prepare acyl chlorides and amides for pharmaceutical and specialty chemical syntheses, and it underpins the production of acetylated resins and specialty polymers in the plastics and coatings industries.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 105.82
    methanol 175.14
    isopropanol 74.74
    water 47.66
    ethyl acetate 98.06
    n-propanol 61.92
    acetone 193.76
    n-butanol 54.43
    acetonitrile 163.92
    DMF 476.97
    toluene 27.64
    isobutanol 46.6
    1,4-dioxane 152.47
    methyl acetate 140.25
    THF 121.43
    2-butanone 111.58
    n-pentanol 42.63
    sec-butanol 54.16
    n-hexane 13.92
    ethylene glycol 70.04
    NMP 389.85
    cyclohexane 9.53
    DMSO 273.45
    n-butyl acetate 40.53
    n-octanol 41.66
    chloroform 80.92
    n-propyl acetate 52.96
    acetic acid 188.55
    dichloromethane 90.41
    cyclohexanone 107.3
    propylene glycol 59.54
    isopropyl acetate 51.15
    DMAc 459.41
    2-ethoxyethanol 101.02
    isopentanol 45.41
    n-heptane 8.11
    ethyl formate 81.68
    1,2-dichloroethane 62.23
    n-hexanol 33.71
    2-methoxyethanol 185.01
    isobutyl acetate 29.41
    tetrachloromethane 15.86
    n-pentyl acetate 38.07
    transcutol 307.94
    n-heptanol 20.41
    ethylbenzene 22.8
    MIBK 45.88
    2-propoxyethanol 86.93
    tert-butanol 82.76
    MTBE 69.22
    2-butoxyethanol 49.1
    propionic acid 102.84
    o-xylene 31.66
    formic acid 118.16
    diethyl ether 65.86
    m-xylene 22.71
    p-xylene 30.69
    chlorobenzene 40.24
    dimethyl carbonate 76.27
    n-octane 4.89
    formamide 148.72
    cyclopentanone 136.36
    2-pentanone 76.03
    anisole 66.07
    cyclopentyl methyl ether 65.26
    gamma-butyrolactone 175.07
    1-methoxy-2-propanol 130.95
    pyridine 92.78
    3-pentanone 73.38
    furfural 176.01
    n-dodecane 6.18
    diethylene glycol 98.79
    diisopropyl ether 23.16
    tert-amyl alcohol 67.25
    acetylacetone 112.05
    n-hexadecane 6.6
    acetophenone 67.43
    methyl propionate 104.12
    isopentyl acetate 36.75
    trichloroethylene 101.93
    n-nonanol 36.35
    cyclohexanol 48.59
    benzyl alcohol 53.67
    2-ethylhexanol 24.51
    isooctanol 18.06
    dipropyl ether 34.54
    1,2-dichlorobenzene 42.4
    ethyl lactate 43.59
    propylene carbonate 90.66
    n-methylformamide 189.67
    2-pentanol 39.35
    n-pentane 10.92
    1-propoxy-2-propanol 60.54
    1-methoxy-2-propyl acetate 58.16
    2-(2-methoxypropoxy) propanol 97.25
    mesitylene 16.47
    ε-caprolactone 106.76
    p-cymene 15.61
    epichlorohydrin 121.19
    1,1,1-trichloroethane 53.11
    2-aminoethanol 76.72
    morpholine-4-carbaldehyde 324.08
    sulfolane 193.33
    2,2,4-trimethylpentane 8.44
    2-methyltetrahydrofuran 90.12
    n-hexyl acetate 67.7
    isooctane 5.11
    2-(2-butoxyethoxy)ethanol 110.32
    sec-butyl acetate 34.65
    tert-butyl acetate 52.55
    decalin 10.02
    glycerin 93.46
    diglyme 181.58
    acrylic acid 115.13
    isopropyl myristate 31.72
    n-butyric acid 85.32
    acetyl acetate 73.53
    di(2-ethylhexyl) phthalate 35.08
    ethyl propionate 63.2
    nitromethane 354.53
    1,2-diethoxyethane 78.68
    benzonitrile 65.92
    trioctyl phosphate 22.91
    1-bromopropane 36.63
    gamma-valerolactone 208.75
    n-decanol 28.6
    triethyl phosphate 27.03
    4-methyl-2-pentanol 24.98
    propionitrile 76.18
    vinylene carbonate 95.43
    1,1,2-trichlorotrifluoroethane 114.7
    DMS 80.65
    cumene 18.79
    2-octanol 19.31
    2-hexanone 53.51
    octyl acetate 40.88
    limonene 21.9
    1,2-dimethoxyethane 182.86
    ethyl orthosilicate 25.01
    tributyl phosphate 32.53
    diacetone alcohol 74.95
    N,N-dimethylaniline 58.89
    acrylonitrile 119.6
    aniline 48.14
    1,3-propanediol 88.46
    bromobenzene 32.85
    dibromomethane 53.71
    1,1,2,2-tetrachloroethane 76.45
    2-methyl-cyclohexyl acetate 33.11
    tetrabutyl urea 49.14
    diisobutyl methanol 18.25
    2-phenylethanol 37.75
    styrene 29.92
    dioctyl adipate 49.43
    dimethyl sulfate 136.39
    ethyl butyrate 39.89
    methyl lactate 80.12
    butyl lactate 35.83
    diethyl carbonate 32.98
    propanediol butyl ether 73.29
    triethyl orthoformate 30.79
    p-tert-butyltoluene 15.37
    methyl 4-tert-butylbenzoate 61.19
    morpholine 148.09
    tert-butylamine 49.55
    n-dodecanol 23.01
    dimethoxymethane 161.68
    ethylene carbonate 71.55
    cyrene 71.98
    2-ethoxyethyl acetate 63.87
    2-ethylhexyl acetate 29.74
    1,2,4-trichlorobenzene 56.15
    4-methylpyridine 112.08
    dibutyl ether 46.65
    2,6-dimethyl-4-heptanol 18.25
    DEF 150.49
    dimethyl isosorbide 104.7
    tetrachloroethylene 52.37
    eugenol 61.33
    triacetin 91.1
    span 80 71.14
    1,4-butanediol 42.23
    1,1-dichloroethane 64.98
    2-methyl-1-pentanol 38.43
    methyl formate 151.51
    2-methyl-1-butanol 44.38
    n-decane 8.73
    butyronitrile 60.54
    3,7-dimethyl-1-octanol 38.29
    1-chlorooctane 24.29
    1-chlorotetradecane 12.9
    n-nonane 8.58
    undecane 7.19
    tert-butylcyclohexane 10.44
    cyclooctane 4.38
    cyclopentanol 58.31
    tetrahydropyran 76.52
    tert-amyl methyl ether 61.22
    2,5,8-trioxanonane 149.08
    1-hexene 29.94
    2-isopropoxyethanol 65.94
    2,2,2-trifluoroethanol 81.92
    methyl butyrate 73.46

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction