Propylene oxide

• Formula: C₃H₆O
• Molecular weight: 58.0791
• IUPAC Standard InChI: InChI=1S/C3H6O/c1-3-2-4-3/h3H,2H2,1H3 Copy

  
• IUPAC Standard InChIKey: GOOHAUXETOMSMM-UHFFFAOYSA-N Copy
• CAS Registry Number: 75-56-9
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Stereoisomers:
  • Oxirane, methyl-, (S)-
• Other names: Oxirane, methyl-; Epoxypropane; Methyloxirane; Propane, 1,2-epoxy-; Propene oxide; Propylene epoxide; 1,2-Epoxypropane; 1,2-Propylene oxide; 2,3-Epoxypropane; 3-Methyl-1,2-epoxypropane; 2-Methyloxiran; Methylethylene oxide; AD 6; Ethylene oxide, methyl-; NCI-C50099; Oxyde de propylene; Propane, epoxy-; UN 1280; 2-Methyl oxirane; Epihydrin; (.+/-.)-Methyloxirane; AD 6 (suspending agent); Methyloxacyclopropane; Oxirane, 2-methyl-; (.+/-.)-1,2-Epoxypropane
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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

View reactions leading to C₃H₆O⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Gas Chromatography, References, Notes

Data compiled by: Coblentz Society, Inc.

• GAS (100 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

Data compiled by: Pamela M. Chu, Franklin R. Guenther, George C. Rhoderick, and Walter J. Lafferty

• gas; IFS66V (Bruker); 3-Term B-H Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); Boxcar Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); Happ Genzel Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); NB Strong Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); Triangular Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Normal alkane RI, non-polar column, isothermal

View large format table.

Normal alkane RI, non-polar column, custom temperature program

View large format table.

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Sinke and Hildenbrand, 1962
Sinke, G.C.; Hildenbrand, D.L., Heat of formation of propylene oxide, J. Chem. Eng. Data, 1962, 7, 74. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Moureu and Dode, 1937
Moureu, H.; Dode, M., Chaleurs de formation de l'oxyde d'ethylene, de l'ethanediol et de quelques homologues, Bull. Soc. Chim. France, 1937, 4, 637-647. [all data]

Oetting F.L., 1964
Oetting F.L., Low-temperature heat capacity and related thermodynamic functions of propylene oxide, J. Chem. Phys., 1964, 41, 149-153. [all data]

Beaumont R.H., 1966
Beaumont R.H., Heat capacities of propylene oxide and some polymers of ethylene and propylene oxides, Polymer, 1966, 7, 401-416. [all data]

Chao J., 1986
Chao J., Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties, J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]

Green, 1961
Green, J.H.S., The thermodynamic properties of propylene oxide, Chem. Ind. (London), 1961, 369. [all data]

McDonald, Shrader, et al., 1959
McDonald, R.A.; Shrader, S.A.; Stull, D.R., Vapor Pressures and Freezing Points of 30 Organics, J. Chem. Eng. Data, 1959, 4, 311. [all data]

Wilhoit, Chao, et al., 1985
Wilhoit, R.C.; Chao, J.; Hall, K.R., Thermodynamic Properties of Key Organic Compounds in the Carbon Range C1 to C4. Part 1. Properties of Condensed Phases, J. Phys. Chem. Ref. Data, 1985, 14, 1. [all data]

Beaumont, Clegg, et al., 1966
Beaumont, R.H.; Clegg, B.; Gee, G.; Herbert, J.B.M.; Marks, D.J.; Roberts, R.C.; Sims, D., Heat Capacities of Propylene Oxide and of Some Polymers of Ethylene and Propylene Oxides, Polymer, 1966, 7, 401. [all data]

Oetting, 1964
Oetting, F.L., Low temperature heat capacity and related thermodynamic functions of propylene oxide, J. Chem. Phys., 1964, 41, 149-53. [all data]

Rutenberg and Shakhova, 1973
Rutenberg, O.L.; Shakhova, S.F., The p-v-t relation on the boundary curve for epoxypropane, Russ. J. Phys. Chem. (Engl. Transl.), 1973, 47, 124-5. [all data]

Kobe, Ravicz, et al., 1956
Kobe, K.A.; Ravicz, A.E.; Vohra, S.P., Critical Properties and Vapor Pressures of Some Ethers and Heterocyclic Compounds, J. Chem. Eng. Data, 1956, 1, 50. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Sinke and Hildenbrand, 1962, 2
Sinke, G.C.; Hildenbrand, D.L., Heat of Formation of Propylene Oxide., J. Chem. Eng. Data, 1962, 7, 1, 74-74, https://doi.org/10.1021/je60012a022 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Dykyj, 1970
Dykyj, J., Petrochemica, 1970, 10, 2, 51. [all data]

Bott and Sadler, 1966
Bott, T.R.; Sadler, H.N., Vapor Pressure of Propylene Oxide., J. Chem. Eng. Data, 1966, 11, 1, 25-25, https://doi.org/10.1021/je60028a005 . [all data]

McDonald, Shrader, et al., 1959, 2
McDonald, R.A.; Shrader, S.A.; Stull, D.R., Vapor Pressures and Freezing Points of Thirty Pure Organic Compounds., J. Chem. Eng. Data, 1959, 4, 4, 311-313, https://doi.org/10.1021/je60004a009 . [all data]

Moor, Kanep, et al., 1937
Moor, V.G.; Kanep, E.K.; Dobkin, I.E., Trans. Exptl. Research Lab. Khemgas, Materials on Cracking and Chemical Treatment of Cracking Products U.S.S.R., 1937, 3, 320. [all data]

Kireev and Popov, 1935
Kireev, V.A.; Popov, A.A., Russ. J. Gen. Chem., 1935, 5, 1399. [all data]

Bott and Sadler, 1966, 2
Bott, T.R.; Sadler, H.N., Vapor Pressure of Propylene Oxide, J. Chem. Eng. Data, 1966, 11, 1, 25-30, https://doi.org/10.1021/je60028a005 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Beaumont, Clegg, et al., 1966, 2
Beaumont, R.H.; Clegg, B.; Gee, G.; Herbert, J.B.M.; Marks, D.J.; Roberts, R.C.; Sims, D., Heat capacities of propylene oxide and of some polymers of ethylene and propylene oxides, Polymer, 1966, 7, 401-416. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T., Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

McAlduff and Houk, 1977
McAlduff, E.J.; Houk, K.N., Photoelectron spectra of substituted oxiranes and thiiranes. Substituent effects on ionization potentials involving σ orbitals, Can. J. Chem., 1977, 55, 318. [all data]

Gallegos and Kiser, 1961
Gallegos, E.J.; Kiser, R.W., Electron impact spectroscopy of ethylene oxide and propylene oxide, J. Am. Chem. Soc., 1961, 83, 773. [all data]

Burgers and Holmes, 1982
Burgers, P.C.; Holmes, J.L., Metastable ion studies. XIII. The measurement of appearance energies of metastable peaks, Org. Mass Spectrom., 1982, 17, 123. [all data]

Cao and Zhang, 2006
Cao, J.; Zhang, H., Inquire into qualitative analysis of epoxyalkyl isomeride, Contemporary Chem. Ind. (Chinese), 2006, 35, 5, 374-377. [all data]

Kurdina, Markovich, et al., 1969
Kurdina, Z.G.; Markovich, V.E.; Sakharov, V.M., Gas chromatography of cyclic O-containing compounds in Gas chromatography, Issue # 10, NIITEKhim, Moscow, 1969, 128-133. [all data]

Farkas, Héberger, et al., 2004
Farkas, O.; Héberger, K.; Zenkevich, I.G., Quantitative structure-retention relationships. XIV. Prediction of gas chromatographic retention indices for saturated O-, N-, and S-heterocyclic compounds, Chemom. Intell. Lab. Syst., 2004, 72, 2, 173-184, https://doi.org/10.1016/j.chemolab.2004.01.012 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  S°gas	Entropy of gas at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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