Propiolactone

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  • Identifiers

    CAS number
    57-57-8

    Molecular formula
    C3H4O2

    SMILES
    C1COC1=O

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Oily 46.69%
    Fatty 45.28%
    Coconut 42.79%
    Buttery 40.28%
    Nutty 38.29%
    Sweet 37.74%
    Creamy 37.49%
    Coumarinic 37.09%
    Winey 34.34%
    Tobacco 32.49%

     

    Flavor
    Sweet 81.83%
    Fatty 55.52%
    Creamy 53.4%
    Oily 49.5%
    Coconut 46.88%
    Caramel 44.34%
    Tonka 41.93%
    Buttery 40.78%
    Herbal 34.55%
    Tobacco 34.34%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.2

    pKa est.
    7.35 (neutral)

    Molecular weight
    72.06 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Melting point expt.

    • -27 °F (EPA, 1998)
    • -33.4ºC
    • -33.4 °C
    • -28 °F

    Boiling point

    • 324 °F at 760 mmHg decomposes (EPA, 1998)
    • Decomposes (155ºC)
    • 61 °C @ 20 MM HG
    • BP: 162 °C @ 760 MM HG (DECOMP); 150 °C @ 750 MM HG (DECOMP); DIPOLE MOMENT: 3.8
    • 323 °F (decomposes)
    • 323 °F (Decomposes)

    Flash point

    • 56.29 ˚C est.
    • 158 °F (EPA, 1998)
    • 74 °C
    • 165 °F (74 °C) (closed cup)
    • 74 °C c.c.
    • 165 °F

    Solubility expt.

    • 10 to 50 mg/mL at 66 °F (NTP, 1992)
    • 370 g/L at 25ºC
    • SOL IN WATER: 37% VOL/VOL; MISCIBLE WITH ALCOHOL, ACETONE, ETHER, CHLOROFORM
    • PROBABLY MISCIBLE WITH MOST POLAR ORG SOLVENTS & LIPIDS
    • water solubility = 3.70X10+5 mg/l @ 25 °C
    • Solubility in water, g/100ml at 25 °C: 37 (good)
    • 37%

  • Synonyms

    • beta-propiolactone
    • Propiolactone
    • 2-Oxetanone
    • 57-57-8
    • Oxetan-2-one
    • Betaprone
    • Propanolide
    • 3-Propanolide
    • 1,3-Propiolactone
    • 3-Propiolactone
    • beta-Propionolactone
    • Propiolactona
    • beta-Propiolakton
    • Propiolactonum
    • Propiolattone
    • Hydracrylic acid beta-lactone
    • .beta.-Propiolactone
    • 3-Hydroxypropionic acid lactone
    • beta-Propanoic acid lactone
    • beta-Proprolactone
    • betapron
    • Caswell No. 709
    • Propiolactone, beta-
    • CCRIS 536
    • NSC 21626
    • NSC-21626
    • HSDB 811
    • UNII-6RC3ZT4HB0
    • 3-Hydroxypropionic acid beta-lactone
    • BPL
    • EINECS 200-340-1
    • Propiolactonum [INN-Latin]
    • 6RC3ZT4HB0
    • beta-lactone hydracrylic acid
    • Propiolactona [INN-Spanish]
    • EPA Pesticide Chemical Code 010901
    • BRN 0001360
    • .beta.-Proprolactone
    • DTXSID8021197
    • CHEBI:49073
    • Propanoic acid, 3-hydroxy-, beta-lactone
    • Propionic acid, 3-hydroxy-, beta-lactone
    • .beta.-Propionolactone
    • AI3-24257
    • Propiolactone .beta.-
    • NSC21626
    • MFCD00005169
    • .beta.-Propanoic acid lactone
    • DTXCID801197
    • Hydracrylic acid .beta.-lactone
    • 3-Hydroxypropionic acid, lactone
    • b-Propiolactone
    • EC 200-340-1
    • 5-17-09-00003 (Beilstein Handbook Reference)
    • NCGC00090802-01
    • Propiolactonum (INN-Latin)
    • Propiolactona (INN-Spanish)
    • PROPIOLACTONE (MART.)
    • PROPIOLACTONE [MART.]
    • BETA-PROPIOLACTONE (IARC)
    • BETA-PROPIOLACTONE [IARC]
    • Propiolattone [DCIT]
    • Propionolactone
    • Oxetanone
    • 3-Propiolacetone
    • beta-Propiolakton [Czech]
    • beta Propiolactone
    • Propiolactone [USAN:INN:BAN]
    • 3-Hydroxy-beta-lactone
    • Propanilide
    • b-Propionolactone
    • oxetan-2one
    • 2-Oxooxetane
    • beta-PL
    • 2-Oxacyclobutanone
    • Betaprone (TN)
    • .beta.-Propiolakton
    • BETRAPRONE
    • .beta.-Propriolactone
    • ? PROPIOLACTONE
    • Spectrum_000216
    • Spectrum2_001982
    • Spectrum4_001274
    • WLN: T4OVTJ
    • Hydracrylic acid ss-lactone
    • PROPIOLACTONE [INN]
    • Propiolactone (USAN/INN)
    • Hydracrylic Acid, b-Lactone
    • PROPIOLACTONE [HSDB]
    • PROPIOLACTONE [USAN]
    • KBioGR_001888
    • KBioSS_000696
    • DivK1c_001003
    • SPECTRUM1503234
    • SPBio_002163
    • Hydracylic acid, .beta.lactone
    • .beta.-lactone hydracrylic acid
    • Propanoic acid, .beta.-lactone
    • Propionic acid, .beta.-lactone
    • CHEMBL1200627
    • HMS503I07
    • KBio1_001003
    • KBio2_000696
    • KBio2_003264
    • KBio2_005832
    • Hydracrylic acid, .beta.-lactone
    • beta-Hydroxypropionic Acid Lactone
    • NINDS_001003
    • HMS1922K19
    • HMS2092P12
    • Pharmakon1600-01503234
    • .BETA.-PROPIOLACTONE [MI]
    • PROPIOLACTONE [ORANGE BOOK]
    • 3-Hydroxypropionic Acid, b-Lactone
    • BCP07366
    • HYDRACRYLIC ACID,BETA,LACTONE
    • Tox21_111026
    • CCG-39865
    • NSC758422
    • HYDRACRYLIC ACID, BETA LACTONE
    • HYDRACRYLIC ACID, BETA-LACTONE
    • AKOS015906936
    • 3-Hydroxypropionic acid .beta.-lactone
    • AT19319
    • DB09348
    • HYDROACRYLIC ACID, BETA-LACTONE
    • NSC-758422
    • beta-Propiolactone, Grade II, >=90%

  • Applications

    Propiolactone (CAS 57-57-8) is used primarily as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It is a reactive lactone that can undergo ring opening to furnish hydroxy ester derivatives, enabling the preparation of building blocks for surfactants and coatings. In polymer science, it can act as a monomer or co-monomer for the synthesis of polyesters and related biodegradable polymers, including materials for drug-delivery systems and coatings. Under controlled conditions, beta-propiolactone is employed as a sterilant or disinfectant for laboratory equipment and medical devices, subject to regulatory oversight. It is also evaluated as a precursor for specialty chemicals such as plasticizers and functional surfactants, depending on local regulations and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 274.29
    methanol 575.14
    isopropanol 165.38
    water 245.2
    ethyl acetate 96.31
    n-propanol 141.58
    acetone 300.34
    n-butanol 120.34
    acetonitrile 453.68
    DMF 647.02
    toluene 32.4
    isobutanol 114.52
    1,4-dioxane 184.04
    methyl acetate 195.6
    THF 120.94
    2-butanone 160.32
    n-pentanol 104.03
    sec-butanol 124.96
    n-hexane 8.74
    ethylene glycol 169.12
    NMP 505.65
    cyclohexane 7.35
    DMSO 708.17
    n-butyl acetate 57.09
    n-octanol 58.0
    chloroform 179.26
    n-propyl acetate 82.39
    acetic acid 921.73
    dichloromethane 286.87
    cyclohexanone 156.77
    propylene glycol 135.64
    isopropyl acetate 49.85
    DMAc 533.29
    2-ethoxyethanol 234.72
    isopentanol 114.45
    n-heptane 5.55
    ethyl formate 171.03
    1,2-dichloroethane 154.24
    n-hexanol 50.25
    2-methoxyethanol 348.79
    isobutyl acetate 37.65
    tetrachloromethane 23.22
    n-pentyl acetate 55.09
    transcutol 580.88
    n-heptanol 34.81
    ethylbenzene 30.0
    MIBK 55.67
    2-propoxyethanol 122.28
    tert-butanol 176.59
    MTBE 85.38
    2-butoxyethanol 96.75
    propionic acid 283.77
    o-xylene 37.08
    formic acid 760.68
    diethyl ether 63.69
    m-xylene 25.08
    p-xylene 47.24
    chlorobenzene 76.59
    dimethyl carbonate 78.36
    n-octane 3.53
    formamide 896.41
    cyclopentanone 191.38
    2-pentanone 89.5
    anisole 105.48
    cyclopentyl methyl ether 55.11
    gamma-butyrolactone 315.18
    1-methoxy-2-propanol 187.45
    pyridine 219.34
    3-pentanone 66.89
    furfural 446.48
    n-dodecane 4.0
    diethylene glycol 161.45
    diisopropyl ether 18.49
    tert-amyl alcohol 151.73
    acetylacetone 136.62
    n-hexadecane 4.22
    acetophenone 137.24
    methyl propionate 101.05
    isopentyl acetate 50.03
    trichloroethylene 288.19
    n-nonanol 47.52
    cyclohexanol 82.01
    benzyl alcohol 125.31
    2-ethylhexanol 33.38
    isooctanol 32.07
    dipropyl ether 25.95
    1,2-dichlorobenzene 87.88
    ethyl lactate 65.46
    propylene carbonate 156.02
    n-methylformamide 465.32
    2-pentanol 74.53
    n-pentane 8.55
    1-propoxy-2-propanol 75.35
    1-methoxy-2-propyl acetate 61.52
    2-(2-methoxypropoxy) propanol 134.44
    mesitylene 17.82
    ε-caprolactone 164.99
    p-cymene 17.99
    epichlorohydrin 244.0
    1,1,1-trichloroethane 71.03
    2-aminoethanol 218.06
    morpholine-4-carbaldehyde 460.6
    sulfolane 363.24
    2,2,4-trimethylpentane 7.19
    2-methyltetrahydrofuran 108.62
    n-hexyl acetate 87.88
    isooctane 4.04
    2-(2-butoxyethoxy)ethanol 178.44
    sec-butyl acetate 43.01
    tert-butyl acetate 49.62
    decalin 6.87
    glycerin 210.31
    diglyme 296.39
    acrylic acid 385.98
    isopropyl myristate 30.63
    n-butyric acid 189.01
    acetyl acetate 91.65
    di(2-ethylhexyl) phthalate 50.24
    ethyl propionate 67.16
    nitromethane 1079.31
    1,2-diethoxyethane 107.01
    benzonitrile 161.92
    trioctyl phosphate 29.68
    1-bromopropane 58.17
    gamma-valerolactone 334.94
    n-decanol 34.92
    triethyl phosphate 34.68
    4-methyl-2-pentanol 45.55
    propionitrile 162.81
    vinylene carbonate 202.92
    1,1,2-trichlorotrifluoroethane 270.74
    DMS 91.63
    cumene 24.94
    2-octanol 31.29
    2-hexanone 77.03
    octyl acetate 43.7
    limonene 23.44
    1,2-dimethoxyethane 283.75
    ethyl orthosilicate 29.93
    tributyl phosphate 42.98
    diacetone alcohol 98.93
    N,N-dimethylaniline 84.24
    acrylonitrile 303.95
    aniline 92.23
    1,3-propanediol 220.51
    bromobenzene 59.88
    dibromomethane 139.51
    1,1,2,2-tetrachloroethane 178.9
    2-methyl-cyclohexyl acetate 44.02
    tetrabutyl urea 63.8
    diisobutyl methanol 22.16
    2-phenylethanol 67.36
    styrene 44.95
    dioctyl adipate 58.6
    dimethyl sulfate 170.53
    ethyl butyrate 50.16
    methyl lactate 101.09
    butyl lactate 67.96
    diethyl carbonate 46.41
    propanediol butyl ether 147.37
    triethyl orthoformate 38.89
    p-tert-butyltoluene 15.78
    methyl 4-tert-butylbenzoate 93.84
    morpholine 206.52
    tert-butylamine 97.87
    n-dodecanol 26.28
    dimethoxymethane 159.26
    ethylene carbonate 133.15
    cyrene 127.66
    2-ethoxyethyl acetate 100.76
    2-ethylhexyl acetate 38.3
    1,2,4-trichlorobenzene 109.98
    4-methylpyridine 212.07
    dibutyl ether 43.21
    2,6-dimethyl-4-heptanol 22.16
    DEF 185.63
    dimethyl isosorbide 146.74
    tetrachloroethylene 130.62
    eugenol 117.17
    triacetin 123.54
    span 80 99.54
    1,4-butanediol 120.75
    1,1-dichloroethane 110.06
    2-methyl-1-pentanol 101.73
    methyl formate 337.08
    2-methyl-1-butanol 110.87
    n-decane 5.83
    butyronitrile 134.94
    3,7-dimethyl-1-octanol 53.86
    1-chlorooctane 22.35
    1-chlorotetradecane 10.07
    n-nonane 5.55
    undecane 4.69
    tert-butylcyclohexane 6.92
    cyclooctane 2.83
    cyclopentanol 95.54
    tetrahydropyran 86.38
    tert-amyl methyl ether 68.73
    2,5,8-trioxanonane 217.75
    1-hexene 30.23
    2-isopropoxyethanol 132.44
    2,2,2-trifluoroethanol 316.7
    methyl butyrate 105.44

    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