Propylene oxide
- Formula: C3H6O
- Molecular weight: 58.0791
- IUPAC Standard InChIKey: GOOHAUXETOMSMM-UHFFFAOYSA-N
- 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:
- 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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Phase change data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, References, Notes
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 308.0 ± 0.3 | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 161.02 | K | N/A | McDonald, Shrader, et al., 1959 | Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 161.22 | K | N/A | Wilhoit, Chao, et al., 1985 | Uncertainty assigned by TRC = 0.05 K; TRC |
Ttriple | 161.25 | K | N/A | Beaumont, Clegg, et al., 1966 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 161.22 | K | N/A | Oetting, 1964 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 488.2 | K | N/A | Rutenberg and Shakhova, 1973 | Uncertainty assigned by TRC = 5. K; Visual, Vp; TRC |
Tc | 482.3 | K | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 53.69 | atm | N/A | Rutenberg and Shakhova, 1973 | Uncertainty assigned by TRC = 0.99995 atm; TRC |
Pc | 48.5847 | atm | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 0.3402 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.195 | l/mol | N/A | Rutenberg and Shakhova, 1973 | Uncertainty assigned by TRC = 0.002 l/mol; TRC |
Vc | 0.186 | l/mol | N/A | Kobe, Ravicz, et al., 1956 | Uncertainty assigned by TRC = 0.005 l/mol; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 5.15 | mol/l | N/A | Rutenberg and Shakhova, 1973 | Uncertainty assigned by TRC = 0.1 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 6.766 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 6.67 | kcal/mol | C | Sinke and Hildenbrand, 1962 | ALS |
ΔvapH° | 6.67 | kcal/mol | N/A | Sinke and Hildenbrand, 1962 | DRB |
ΔvapH° | 6.67 | kcal/mol | C | Sinke and Hildenbrand, 1962, 2 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
6.537 | 307.7 | N/A | Majer and Svoboda, 1985 | |
7.55 | 240. | A | Stephenson and Malanowski, 1987 | Based on data from 225. to 308. K. See also Dykyj, 1970.; AC |
6.81 | 307. | N/A | Bott and Sadler, 1966 | Based on data from 292. to 345. K.; AC |
7.19 | 264. | N/A | McDonald, Shrader, et al., 1959, 2 | Based on data from 249. to 308. K.; AC |
6.74 | 303. | N/A | Moor, Kanep, et al., 1937 | Based on data from 285. to 322. K.; AC |
7.86 | 273. | N/A | Kireev and Popov, 1935 | Based on data from 243. to 306. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
292. to 345.0 | 3.54475 | 802.487 | -81.348 | Bott and Sadler, 1966, 2 | Coefficents calculated by NIST from author's data. |
199.70 to 307.38 | 4.08916 | 1065.27 | -46.867 | McDonald, Shrader, et al., 1959, 2 |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.5614 | 161.22 | Oetting F.L., 1964 | DH |
1.57 | 161.3 | Domalski and Hearing, 1996 | AC |
1.570 | 161.25 | Beaumont, Clegg, et al., 1966, 2 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.685 | 161.22 | Oetting F.L., 1964 | DH |
9.737 | 161.25 | Beaumont, Clegg, et al., 1966, 2 | DH |
Gas phase ion energetics data
Go To: Top, Phase change data, Gas Chromatography, References, Notes
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 10.22 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 192.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 184.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.1 | PE | Aue and Bowers, 1979 | LLK |
10.22 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
10.44 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
10.26 | PE | McAlduff and Houk, 1977 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHO+ | 11.8 ± 0.2 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
CH2+ | 18.8 ± 0.5 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
CH2O+ | 11.6 ± 0.3 | C2H4 | EI | Gallegos and Kiser, 1961 | RDSH |
CH3+ | 13.9 ± 0.2 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
CH3O+ | 13.4 ± 0.2 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
C2H2+ | 13.9 ± 0.2 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
C2H2O+ | 12.7 ± 0.2 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
C2H3+ | 14.3 ± 0.1 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
C2H3O+ | 10.72 ± 0.05 | CH3 | EI | Burgers and Holmes, 1982 | LBLHLM |
C2H3O+ | 10.9 ± 0.2 | CH3 | EI | Gallegos and Kiser, 1961 | RDSH |
C2H4+ | 11.6 ± 0.2 | ? | EI | Gallegos and Kiser, 1961 | RDSH |
C3H5O+ | 11.5 ± 0.3 | H | EI | Gallegos and Kiser, 1961 | RDSH |
Gas Chromatography
Go To: Top, Phase change data, Gas phase ion energetics data, References, Notes
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Methyl Silicone | 60. | 447. | Cao and Zhang, 2006 | Column length: 50. m; Column diameter: 0.25 mm |
Capillary | Methyl Silicone | 70. | 447. | Cao and Zhang, 2006 | Column length: 50. m; Column diameter: 0.25 mm |
Capillary | Methyl Silicone | 80. | 448. | Cao and Zhang, 2006 | Column length: 50. m; Column diameter: 0.25 mm |
Packed | Apieson L | 120. | 460. | Kurdina, Markovich, et al., 1969 | not specified, not specified |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 477. | Farkas, Héberger, et al., 2004 | Program: not specified |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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
Sinke, G.C.; Hildenbrand, D.L.,
Heat of formation of propylene oxide,
J. Chem. Eng. Data, 1962, 7, 74. [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]
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]
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, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Vc Critical volume 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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