Oxirane, (phenoxymethyl)-
- Formula: C9H10O2
- Molecular weight: 150.1745
- IUPAC Standard InChI: InChI=1S/C9H10O2/c1-2-4-8(5-3-1)10-6-9-7-11-9/h1-5,9H,6-7H2
- IUPAC Standard InChIKey: FQYUMYWMJTYZTK-UHFFFAOYSA-N
- CAS Registry Number: 122-60-1
- 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. - Other names: Propane, 1,2-epoxy-3-phenoxy-; γ-Phenoxypropylene oxide; (Phenoxymethyl)oxirane; Glycidol phenyl ether; Glycidyl phenyl ether; Phenol glycidyl ether; Phenyl glycidyl ether; Phenyl 2,3-epoxypropyl ether; 1-Phenoxy-2,3-epoxypropane; 1,2-Epoxy-3-phenoxypropane; 2,3-Epoxypropyl phenyl ether; 3-Phenoxy-1,2-epoxypropane; 3-Phenoxy-1,2-propylene oxide; 3-Phenyloxy-1,2-epoxypropane; (.+/-.)-1,2-Epoxy-3-phenoxypropane; Benzene, (2,3-epoxypropoxy)-; Ether, phenylglycidyl; Ether, 2,3-epoxypropyl phenyl; Fenyl-glycidylether; Phenoxypropene oxide; Phenoxypropylene oxide; Phenylglycydyl ether; PGE; Ageflex pge; Phenol-glycidaether; 3-Phenyloxy-1,2-epoxypropanel-, (.+/-.)-; 2,3-Epoxy-1-phenoxypropane; 2,3-Epoxypropoxybenzene; Oxirane, 2-(phenoxymethyl)-; NSC 53476; (.+/-.)-(Phenoxymethyl)oxirane; 2-(Phenoxymethyl)oxirane
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -99.7 ± 1.1 | kJ/mol | Ccb | Steele, Chirico, et al., 1997 | |
| ΔfH°gas | -116.4 ± 2.1 | kJ/mol | Ccb | Van-Chin-Syan and Kachurina, 1987 | |
| ΔfH°gas | -116. ± 2. | kJ/mol | Ccb | Kuznetsova, Miroshnichenko, et al., 1976 |
Condensed 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -169.53 ± 0.78 | kJ/mol | Ccb | Steele, Chirico, et al., 1997 | ALS |
| ΔfH°liquid | -182. ± 2. | kJ/mol | Ccb | Kuznetsova, Miroshnichenko, et al., 1976 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -4801.21 ± 0.64 | kJ/mol | Ccb | Steele, Chirico, et al., 1997 | Corresponding ΔfHºliquid = -169.53 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -4785. ± 2. | kJ/mol | Ccb | Kuznetsova, Miroshnichenko, et al., 1976 | Corresponding ΔfHºliquid = -186. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 274.9 | J/mol*K | N/A | Lebedev, Bykova, et al., 1988 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 276.0 | 298.15 | Lebedev, Bykova, et al., 1988 | T = 5 to 330 K.; DH |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 278.7 | 298. | Lesbats and Lichanot, 1987 | T = 225 to 400 K.; DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
=
+
By formula: C15H17NO2 = C9H10O2 + C6H7N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 113. ± 2. | kJ/mol | Cm | Kuznetsova, Rakova, et al., 1975 | solid phase; solvent: DMF |
+
=
By formula: C7H5NO + C9H10O2 = C16H15NO3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -196.7 | kJ/mol | Cm | Lebedev, Bykova, et al., 1988, 2 | liquid phase |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Steele, Chirico, et al., 1997
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Knipmeyer, S.E.; Nguyen, A.,
Thermodynamic properties and ideal-gas enthalpies of formation for 2-aminoisobutyric acid (2-methylalanine), acetic acid, (4-methyl-3-penten-2-one), 4-methylpent-1-ene, 2,2'-bis(phenylthio)propane, and glycidyl phenyl ether (1,2-epoxy-3-phenoxypropane),
J. Chem. Eng. Data, 1997, 42, 1052-1066. [all data]
Van-Chin-Syan and Kachurina, 1987
Van-Chin-Syan, Yu.Ya.; Kachurina, N.S.,
Thermochemical properties of oxirane derivatives,
Russ. J. Phys. Chem. (Engl. Transl.), 1987, 61, 622-624. [all data]
Kuznetsova, Miroshnichenko, et al., 1976
Kuznetsova, V.P.; Miroshnichenko, E.A.; Zelenetskii, A.N.; Rakova, G.V.; Lebedev, Yu.A.; Enikolopyan, N.S.,
Enthalpies of reactions of epoxides with primary amines,
Dokl. Phys. Chem. (Engl. Transl.), 1976, 226, 147-150, In original 1109. [all data]
Lebedev, Bykova, et al., 1988
Lebedev, B.V.; Bykova, T.A.; Kiparisova, Y.G.; Frenkel, Ts.M.; Fainleib, A.M.; Pankratov, V.A.,
Thermodynamics of phenyl glycidyl ether and its reactions with diphenylcarbodiimide and phenyl isocyanate with the formation of iminooxazolidinone and oxazolidinone in the range 0-330 K, Izvest. Akad. Nauk SSSR,
Ser. Khim., 1988, (6), 1232-1237. [all data]
Lesbats and Lichanot, 1987
Lesbats, C.; Lichanot, A.,
Capacites calorifiques de durcisseurs amines et resines epoxydes,
Thermochim. Acta, 1987, 109, 317-329. [all data]
Kuznetsova, Rakova, et al., 1975
Kuznetsova, V.P.; Rakova, G.V.; Miroshnichenko, E.A.; Lebedev, Yu.A.; Enikolopyan, N.S.,
Thermochemical study of the interaction of epoxy compounds with primary amines,
Dokl. Phys. Chem. (Engl. Transl.), 1975, 225, 1231-1234. [all data]
Lebedev, Bykova, et al., 1988, 2
Lebedev, B.V.; Bykova, T.A.; Kiparisova, E.G.; Frenkel, Ts.M.; Fainleib, A.M.; Pankratov, V.A.,
Thermodynamics of phenyl glycidyl ether and its reactions with diphenylcarbodiimide and phenyl isocyanate with the formation of iminooxazolidine and oxazolidinone in the 0-330 K range,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, 1082-10. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Cp,solid Constant pressure heat capacity of solid S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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