Diketene

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  • Identifiers

    CAS number
    674-82-8

    Molecular formula
    C4H4O2

    SMILES
    C=C1CC(=O)O1

    Safety labels

    Flammable
    Flammable

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Nutty 41.73%
    Sweet 38.46%
    Burnt 37.81%
    Caramellic 33.68%
    Buttery 31.59%
    Coumarinic 29.88%
    Odorless 29.56%
    Tobacco 29.35%
    Spicy 28.92%
    Coconut 28.71%

     

    Flavor
    Caramel 23.53%
    Buttery 21.43%
    Sweet 21.08%
    Cotton candy 21.08%
    Extremely sweet 20.73%
    Fenugreek 20.72%
    Seedy 20.48%
    Maple syrup 20.04%
    Toffee 20.02%
    Odorless 19.97%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.3

    pKa est.
    8.61 (weak base)

    Molecular weight
    84.07 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Melting point expt.

    • -6.5 °C
    • Heat of Fusion at Melting Point = 1.44X10+7 Joules kmol
    • -7 °C

    Boiling point

    • 127 °C

    Flash point

    • 46.77 ˚C est.
    • 93 °F (NFPA, 2010)
    • 90 °F
    • 93.2 °F (34 °C) - closed cup
    • 93 °F (33.9 °C) - open cup
    • 93 °F (34 °C) - closed cup
    • 33 °C c.c.

    Solubility expt.

    • Very slightly soluble in water in which it decomposes slowly
    • Miscible with most organic solvents. Miscible with hexane
    • Slightly soluble in aliphatic hydrocarbons such as hexane (ca. 12.5 wt% at 23 °C), octane, cyclohexane, and methyl cyclohexane
    • Soluble in common organic solvents
    • Solubility in water at 25 °C: slowly hydrolyzes

  • Synonyms

    • Diketene
    • 674-82-8
    • 2-Oxetanone, 4-methylene-
    • 4-Methylene-2-oxetanone
    • Ethenone, dimer
    • 4-methyleneoxetan-2-one
    • 4-methylideneoxetan-2-one
    • Diketen
    • But-3-en-3-olide
    • Ketene dimer
    • Ethenone, dimer (VAN)
    • HSDB 2063
    • EINECS 211-617-1
    • UNII-0DZ97C3Z7D
    • NSC 93783
    • BRN 0104541
    • CCRIS 8887
    • DIKETENE [MI]
    • NSC-93783
    • Vinylaceto-.beta.-lactone
    • ACETYL KETENE [HSDB]
    • 0DZ97C3Z7D
    • DTXSID9027289
    • EC 211-617-1
    • 5-17-09-00115 (Beilstein Handbook Reference)
    • Ketene, dimer
    • 3-Buteno-beta-lactone
    • Vinylaceto-beta-lactone
    • UN2521
    • 4-Methylene-oxetan-2-one
    • 3-Butenoic acid, 3-hydroxy-, beta-lactone
    • But3en3olide
    • 3Butenobetalactone
    • Diketene, inhibited
    • Vinylacetobetalactone
    • 4Methylene2oxetanone
    • 2Oxetanone, 4methylene
    • 4-Methylidene-2-oxetanone
    • DIKETENE, STABILIZED
    • WLN: T4VOY DHJ CU1
    • DTXCID107289
    • 3-BUTENO-.BETA.-LACTONE
    • 3-Butenoic acid, .beta.-lactone
    • NSC93783
    • 3Butenoic acid, 3hydroxy, betalactone
    • AKOS000121393
    • Diketene, inhibited [UN2521] [Poison]
    • NS00003079
    • EN300-21170
    • 3-Butenoic acid, 3-hydroxy-, .beta.-lactone
    • Diketene, contains copper sulfate as stabilizer
    • Q418541

  • Applications

    Diketene (CAS 674-82-8) is primarily used as an acetoacetylating agent to form beta-keto esters (for example, ethyl acetoacetate and methyl acetoacetate), which are important intermediates in flavor and fragrance chemistry. These acetoacetates are widely used as aroma precursors in flavors and perfumery and also serve as building blocks in cosmetic formulations. In polymer and coating technology, diketene-derived acetoacetylates are used to prepare acetoacetylated monomers and resins, enabling crosslinking and performance-enhancing modifications in coatings, adhesives, and plastics. Additionally, diketene itself is used as a reactive intermediate in general organic synthesis to access a range of specialty chemicals for industrial manufacturing.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 118.75
    methanol 194.31
    isopropanol 95.22
    water 63.32
    ethyl acetate 70.06
    n-propanol 83.61
    acetone 179.98
    n-butanol 67.4
    acetonitrile 147.24
    DMF 504.13
    toluene 6.72
    isobutanol 58.27
    1,4-dioxane 115.82
    methyl acetate 108.71
    THF 141.78
    2-butanone 89.43
    n-pentanol 54.57
    sec-butanol 68.23
    n-hexane 2.97
    ethylene glycol 132.17
    NMP 282.99
    cyclohexane 1.55
    DMSO 250.33
    n-butyl acetate 28.95
    n-octanol 42.21
    chloroform 27.18
    n-propyl acetate 47.4
    acetic acid 262.47
    dichloromethane 28.94
    cyclohexanone 60.36
    propylene glycol 149.71
    isopropyl acetate 40.34
    DMAc 373.4
    2-ethoxyethanol 151.55
    isopentanol 54.83
    n-heptane 2.61
    ethyl formate 71.15
    1,2-dichloroethane 24.4
    n-hexanol 36.57
    2-methoxyethanol 288.53
    isobutyl acetate 28.62
    tetrachloromethane 3.71
    n-pentyl acetate 26.13
    transcutol 345.52
    n-heptanol 23.1
    ethylbenzene 7.3
    MIBK 45.29
    2-propoxyethanol 131.17
    tert-butanol 102.97
    MTBE 43.43
    2-butoxyethanol 67.1
    propionic acid 110.98
    o-xylene 9.51
    formic acid 175.08
    diethyl ether 43.17
    m-xylene 8.56
    p-xylene 9.81
    chlorobenzene 11.91
    dimethyl carbonate 74.95
    n-octane 1.42
    formamide 194.13
    cyclopentanone 102.39
    2-pentanone 66.43
    anisole 47.54
    cyclopentyl methyl ether 48.24
    gamma-butyrolactone 154.65
    1-methoxy-2-propanol 225.33
    pyridine 46.62
    3-pentanone 49.42
    furfural 153.12
    n-dodecane 2.68
    diethylene glycol 170.72
    diisopropyl ether 13.27
    tert-amyl alcohol 69.64
    acetylacetone 99.35
    n-hexadecane 2.78
    acetophenone 50.48
    methyl propionate 84.99
    isopentyl acetate 26.3
    trichloroethylene 42.56
    n-nonanol 37.87
    cyclohexanol 38.88
    benzyl alcohol 45.36
    2-ethylhexanol 21.27
    isooctanol 19.22
    dipropyl ether 24.73
    1,2-dichlorobenzene 14.93
    ethyl lactate 62.16
    propylene carbonate 82.71
    n-methylformamide 217.18
    2-pentanol 46.26
    n-pentane 2.74
    1-propoxy-2-propanol 82.93
    1-methoxy-2-propyl acetate 58.35
    2-(2-methoxypropoxy) propanol 117.31
    mesitylene 6.51
    ε-caprolactone 69.31
    p-cymene 7.49
    epichlorohydrin 112.42
    1,1,1-trichloroethane 21.06
    2-aminoethanol 148.21
    morpholine-4-carbaldehyde 270.98
    sulfolane 158.19
    2,2,4-trimethylpentane 2.29
    2-methyltetrahydrofuran 70.34
    n-hexyl acetate 53.19
    isooctane 2.09
    2-(2-butoxyethoxy)ethanol 147.43
    sec-butyl acetate 29.14
    tert-butyl acetate 45.36
    decalin 2.51
    glycerin 223.73
    diglyme 188.65
    acrylic acid 130.76
    isopropyl myristate 24.77
    n-butyric acid 88.22
    acetyl acetate 56.51
    di(2-ethylhexyl) phthalate 30.77
    ethyl propionate 54.32
    nitromethane 410.84
    1,2-diethoxyethane 54.88
    benzonitrile 38.83
    trioctyl phosphate 22.22
    1-bromopropane 11.3
    gamma-valerolactone 179.13
    n-decanol 30.09
    triethyl phosphate 22.46
    4-methyl-2-pentanol 30.75
    propionitrile 67.9
    vinylene carbonate 81.75
    1,1,2-trichlorotrifluoroethane 120.49
    DMS 59.59
    cumene 8.33
    2-octanol 18.51
    2-hexanone 50.92
    octyl acetate 34.83
    limonene 10.03
    1,2-dimethoxyethane 192.88
    ethyl orthosilicate 19.75
    tributyl phosphate 28.19
    diacetone alcohol 93.88
    N,N-dimethylaniline 40.68
    acrylonitrile 100.13
    aniline 29.62
    1,3-propanediol 144.69
    bromobenzene 7.04
    dibromomethane 13.92
    1,1,2,2-tetrachloroethane 36.67
    2-methyl-cyclohexyl acetate 26.88
    tetrabutyl urea 43.23
    diisobutyl methanol 14.61
    2-phenylethanol 36.31
    styrene 8.34
    dioctyl adipate 40.94
    dimethyl sulfate 113.36
    ethyl butyrate 31.02
    methyl lactate 110.14
    butyl lactate 43.1
    diethyl carbonate 26.79
    propanediol butyl ether 119.69
    triethyl orthoformate 24.93
    p-tert-butyltoluene 7.76
    methyl 4-tert-butylbenzoate 60.41
    morpholine 138.45
    tert-butylamine 47.11
    n-dodecanol 23.87
    dimethoxymethane 193.32
    ethylene carbonate 58.45
    cyrene 104.71
    2-ethoxyethyl acetate 46.54
    2-ethylhexyl acetate 18.88
    1,2,4-trichlorobenzene 22.85
    4-methylpyridine 51.87
    dibutyl ether 29.92
    2,6-dimethyl-4-heptanol 14.61
    DEF 103.52
    dimethyl isosorbide 124.82
    tetrachloroethylene 19.44
    eugenol 72.26
    triacetin 75.89
    span 80 84.72
    1,4-butanediol 74.96
    1,1-dichloroethane 23.74
    2-methyl-1-pentanol 43.19
    methyl formate 175.95
    2-methyl-1-butanol 52.73
    n-decane 3.51
    butyronitrile 51.99
    3,7-dimethyl-1-octanol 36.76
    1-chlorooctane 13.86
    1-chlorotetradecane 7.94
    n-nonane 2.91
    undecane 3.01
    tert-butylcyclohexane 3.23
    cyclooctane 0.91
    cyclopentanol 58.39
    tetrahydropyran 51.95
    tert-amyl methyl ether 38.41
    2,5,8-trioxanonane 164.92
    1-hexene 10.41
    2-isopropoxyethanol 93.31
    2,2,2-trifluoroethanol 107.71
    methyl butyrate 63.74

    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