Oxirane, (phenoxymethyl)-
- Formula: C9H10O2
- Molecular weight: 150.1745
- 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, Phase change 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 |
Phase change data
Go To: Top, Gas 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 518.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 276.79 | K | N/A | Lebedev, Bykova, et al., 1988 | DH |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 280. | K | N/A | Lebedev, Bykova, et al., 1988, 2 | Uncertainty assigned by TRC = 0.1 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 720. | K | N/A | Steele, Chirico, et al., 1997, 2 | Uncertainty assigned by TRC = 8. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 29.50 | bar | N/A | Steele, Chirico, et al., 1997, 2 | Uncertainty assigned by TRC = 4.00 bar; derived from fit of obs. vapor pressure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.16 | mol/l | N/A | Steele, Chirico, et al., 1997, 2 | Uncertainty assigned by TRC = 0.13 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 69.85 | kJ/mol | V | Steele, Chirico, et al., 1997 | ALS |
ΔvapH° | 69.8 | kJ/mol | N/A | Steele, Chirico, et al., 1997 | DRB |
ΔvapH° | 69.9 ± 0.7 | kJ/mol | EB | Steele, Chirico, et al., 1997, 3 | Based on data from 400. to 532. K.; AC |
ΔvapH° | 65.6 ± 0.1 | kJ/mol | V | Van-Chin-Syan and Kachurina, 1987 | ALS |
ΔvapH° | 66.0 | kJ/mol | N/A | Kuznetsova, Miroshnichenko, et al., 1976 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
60.3 ± 0.5 | 400. | EB | Steele, Chirico, et al., 1997, 3 | Based on data from 400. to 532. K.; AC |
56.7 ± 0.4 | 440. | EB | Steele, Chirico, et al., 1997, 3 | Based on data from 400. to 532. K.; AC |
53.1 ± 0.4 | 480. | EB | Steele, Chirico, et al., 1997, 3 | Based on data from 400. to 532. K.; AC |
51.3 ± 0.5 | 500. | EB | Steele, Chirico, et al., 1997, 3 | Based on data from 400. to 532. K.; AC |
49.4 ± 0.6 | 520. | EB | Steele, Chirico, et al., 1997, 3 | Based on data from 400. to 532. K.; AC |
65.6 ± 0.1 | 343. to 373. | N/A | Kuznetsova, Miroshinichenko, et al., 1976 | AC |
65.61 ± 0.08 | 343. | V | Kuznetsova, Miroshnichenko, et al., 1976 | ALS |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
17.32 | 279.8 | Lebedev, Bykova, et al., 1988, 3 | AC |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change 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, 4 | liquid phase |
References
Go To: Top, Gas phase thermochemistry data, Phase change 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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]
Lebedev, Bykova, et al., 1988, 2
Lebedev, B.V.; Bykova, T.A.; Kiparisova, E.G.; Frenkel, Ts.M.; Fainleib, A.M.; Pankratov, V.A.,
Bull. Acad. Sci. USSR, Div. Chem. Sci. (Eng. Tran.), 1988, 37. [all data]
Steele, Chirico, et al., 1997, 2
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, (Z)-5-Ethylidene-2- norbornene, Mesityl Oxide (4-Methyl-3-pentene-2-one), 4-M,
J. Chem. Eng. Data, 1997, 42, 1053-66. [all data]
Steele, Chirico, et al., 1997, 3
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, ( Z )-5-Ethylidene-2-norbornene, Mesityl Oxide (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, 6, 1053-1066, https://doi.org/10.1021/je970099y
. [all data]
Kuznetsova, Miroshinichenko, et al., 1976
Kuznetsova, V.P.; Miroshinichenko, E.A.; Zelenetskii, A.Z.; Rokova, G.V.; Lebedev, Y.A.; Enikolopyan, N.S.,
Dokl. Phys. Chem., 1976, 226, 147. [all data]
Lebedev, Bykova, et al., 1988, 3
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,
Russ Chem Bull, 1988, 37, 6, 1082-1086, https://doi.org/10.1007/BF00961904
. [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, 4
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, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔrH° Enthalpy of reaction at standard conditions 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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