Benzene, ethoxy-

Formula: C₈H₁₀O
Molecular weight: 122.1644
IUPAC Standard InChI: InChI=1S/C8H10O/c1-2-9-8-6-4-3-5-7-8/h3-7H,2H2,1H3
IUPAC Standard InChIKey: DLRJIFUOBPOJNS-UHFFFAOYSA-N
CAS Registry Number: 103-73-1
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: Phenetole; Ethoxybenzene; Ethyl phenyl ether; Phenyl ethyl ether; Ether, ethyl phenyl-; Phenoxyethane; Benzyl methyl ether
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-24.28 ± 0.28	kcal/mol	Ccb	Fenwick, Harrop, et al., 1975	Author was aware that data differs from previously reported values; ALS
Δ_fH°_gas	-29.8	kcal/mol	Ccb	Gray and Williams, 1959	Private communication; ALS
Δ_fH°_gas	-25.91	kcal/mol	N/A	Badoche, 1941	Value computed using Δ_fH_liquid° value of -159.4 kj/mol from Badoche, 1941 and Δ_vapH° value of 51.0 kj/mol from Fenwick, Harrop, et al., 1975.; DRB

Condensed phase thermochemistry data

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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
Δ_fH°_liquid	-36.48 ± 0.28	kcal/mol	Ccb	Fenwick, Harrop, et al., 1975	Author was aware that data differs from previously reported values; ALS
Δ_fH°_liquid	-38.10	kcal/mol	Ccb	Badoche, 1941	Author's hf298-condensed=-41.22 kcal/mol; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1057.50	kcal/mol	Ccb	Fenwick, Harrop, et al., 1975	Author was aware that data differs from previously reported values; Corresponding Δ_fHº_liquid = -36.482 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-1055.89	kcal/mol	Ccb	Badoche, 1941	Author's hf298-condensed=-41.22 kcal/mol; Corresponding Δ_fHº_liquid = -38.09 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
54.61	298.15	Fenwick, Harrop, et al., 1975, 2	DH

Phase change data

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

Quantity	Value	Units	Method	Reference	Comment
T_boil	443.4 ± 0.4	K	AVG	N/A	Average of 11 out of 12 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	243.63	K	N/A	Dreisbach and Martin, 1949	Uncertainty assigned by TRC = 0.05 K; TRC
T_fus	243.68	K	N/A	Olson, Hipsher, et al., 1947	Uncertainty assigned by TRC = 0.3 K; TRC
T_fus	243.48	K	N/A	Boord, Greenlee, et al., 1945	Uncertainty assigned by TRC = 0.3 K; TRC
T_fus	242.95	K	N/A	Timmermans, 1921	Uncertainty assigned by TRC = 0.3 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_c	647.0	K	N/A	Guye and Mallet, 1902	Uncertainty assigned by TRC = 2. K; TRC
T_c	647.15	K	N/A	Guye and Mallet, 1902, 2	Uncertainty assigned by TRC = 2.5 K; accompanied by some decomposition; TRC
Quantity	Value	Units	Method	Reference	Comment
P_c	33.75	atm	N/A	Guye and Mallet, 1902	Uncertainty assigned by TRC = 0.8000 atm; TRC
P_c	33.9000	atm	N/A	Guye and Mallet, 1902, 2	Uncertainty assigned by TRC = 0.99995 atm; TRC
P_c	33.7000	atm	N/A	Guye and Mallet, 1902, 2	Uncertainty assigned by TRC = 0.99995 atm; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	12.20	kcal/mol	N/A	Majer and Svoboda, 1985
Δ_vapH°	12.1	kcal/mol	N/A	Ambrose, Ellender, et al., 1976	Based on data from 390. to 454. K.; AC
Δ_vapH°	12.20 ± 0.029	kcal/mol	C	Fenwick, Harrop, et al., 1975	Author was aware that data differs from previously reported values; ALS
Δ_vapH°	12.2	kcal/mol	N/A	Fenwick, Harrop, et al., 1975	DRB
Δ_vapH°	12.2 ± 0.02	kcal/mol	C	Fenwick, Harrop, et al., 1975	AC

Reduced pressure boiling point

T_boil (K)	Pressure (atm)	Reference	Comment
333.2	0.01	Weast and Grasselli, 1989	BS

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
10.6	405.	A	Stephenson and Malanowski, 1987	Based on data from 390. to 454. K. See also Ambrose, Ellender, et al., 1976.; AC
9.73	443.	N/A	Ambrose, Ellender, et al., 1976	Based on data from 390. to 454. K.; AC
10.5	415.	N/A	Collerson, Counsell, et al., 1965	Based on data from 400. to 454. K. See also Boublik, Fried, et al., 1984.; AC

Antoine Equation Parameters

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

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Temperature (K)	A	B	C	Reference
390.58 to 453.8	4.1390	1507.267	-78.793	Collerson, Counsell, et al., 1965, 2

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	C78, Branched paraffin	130.	978.5	Dallos, Sisak, et al., 2000	He; Column length: 3.3 m
Packed	OV-101	100.	976.3	Righezza, Hassani, et al., 1996	N2, Chromosorb G HP; Column length: 5. m
Packed	OV-101	110.	981.3	Righezza, Hassani, et al., 1996	N2, Chromosorb G HP; Column length: 5. m
Packed	OV-101	80.	971.6	Righezza, Hassani, et al., 1996	N2, Chromosorb G HP; Column length: 5. m
Packed	OV-101	90.	973.3	Righezza, Hassani, et al., 1996	N2, Chromosorb G HP; Column length: 5. m
Packed	OV-101	120.	980.5	Hassani and Meklati, 1992	N2, Chromosorb G HP; Column length: 5. m
Packed	C78, Branched paraffin	130.	978.1	Reddy, Dutoit, et al., 1992	Chromosorb G HP; Column length: 3.3 m
Packed	Apolane	130.	980.	Dutoit, 1991	Column length: 3.7 m
Packed	SE-30	180.	995.	Oszczapowicz, Osek, et al., 1985	N2, Chromosorb A AW; Column length: 3. m
Packed	SE-30	180.	995.	Oszczapowicz, Osek, et al., 1984	N2, Chromosorb W AW; Column length: 3. m
Packed	SE-30	150.	984.	Tibor and Anna, 1971	N2, Chromosorb W-AW; Column length: 2. m
Packed	SE-30	170.	995.	Tibor and Anna, 1971	N2, Chromosorb W-AW; Column length: 2. m
Packed	Squalane	100.	953.7	Evans and Smith, 1967	H2/N2=3/1, Celite; Column length: 2. m
Packed	Squalane	100.	953.	Evans and Smith, 1967	H2/N2=3/1, Celite; Column length: 2. m
Packed	Apiezon L	130.	996.	Wehrli and Kováts, 1959	Celite; Column length: 2.25 m

Kovats' RI, polar column, isothermal

View large format table.

Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	PEG-20M	150.	1437.	Tibor and Anna, 1971	N2, Chromosorb W-AW; Column length: 2. m
Packed	PEG-20M	170.	1442.	Tibor and Anna, 1971	N2, Chromosorb W-AW; Column length: 2. m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-5	988.8	Song, Lai, et al., 2003	30. m/0.25 mm/0.25 μm, He, 2. K/min; T_start: 40. C; T_end: 310. C
Capillary	DB-5	991.1	Song, Lai, et al., 2003	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 40. C; T_end: 310. C
Capillary	DB-5	992.4	Song, Lai, et al., 2003	30. m/0.25 mm/0.25 μm, He, 6. K/min; T_start: 40. C; T_end: 310. C
Capillary	OV-1	970.8	Gautzsch and Zinn, 1996	8. K/min; T_start: 35. C; T_end: 300. C
Capillary	DB-5	988.8	Lai and Song, 1995	30. m/0.25 mm/0.25 μm, He, 2. K/min; T_start: 40. C; T_end: 310. C
Capillary	DB-5	991.1	Lai and Song, 1995	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 40. C; T_end: 310. C
Capillary	DB-5	992.4	Lai and Song, 1995	30. m/0.25 mm/0.25 μm, He, 6. K/min; T_start: 40. C; T_end: 310. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	OV-101	980.	Ebrahimi and Hadjmohammadi, 2006	Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, Notes

Fenwick, Harrop, et al., 1975
Fenwick, J.O.; Harrop, D.; Head, A.J., Thermodynamic properties of organic oxygen compounds. 41. Enthalpies of formation of eight ethers, J. Chem. Thermodyn., 1975, 7, 943-954. [all data]

Gray and Williams, 1959
Gray, P.; Williams, A., Chemistry of free radicals containing oxygen. Part 3.- Thermochemistry and reactivity of the higher alkoxyl radicals RO·, Trans. Faraday Soc., 1959, 55, 760-777. [all data]

Badoche, 1941
Badoche, M., No 19. - Chaleurs de combustion du phenol, du-m-cresol et del leurs ethers; par M. Marius BADOCHE., Bull. Soc. Chim. Fr., 1941, 8, 212-220. [all data]

Fenwick, Harrop, et al., 1975, 2
Fenwick, J.O.; Harrop, D.; Head, A.J., Thermodynamic properties of organic oxygen compounds. 41. Enthalpies of formation of eight ethers, J. Chem. Thermodynam., 1975, 7, 944-954. [all data]

Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A., Physical Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 2875-8. [all data]

Olson, Hipsher, et al., 1947
Olson, W.T.; Hipsher, H.F.; Buess, C.M.; Goodman, I.A.; Hart, I.; Lamneck, J.H.; Gibbons, L.C., The Synthesis and Purification of Ethers, J. Am. Chem. Soc., 1947, 69, 2451-4. [all data]

Boord, Greenlee, et al., 1945
Boord, C.E.; Greenlee, K.W.; Perilstein, W.L., , Am. Pet. Inst. Res. Proj. 45, Seventh Annu. Rep., Ohio State Univ., June 30, 1945. [all data]

Timmermans, 1921
Timmermans, J., The Freezing Points of Organic Substances IV. New Exp. Determinations, Bull. Soc. Chim. Belg., 1921, 30, 62. [all data]

Guye and Mallet, 1902
Guye, P.A.; Mallet, E., Critical Constant and Molecular Complexity of Several Organic Compds., C. R. Hebd. Seances Acad. Sci., 1902, 133, 168. [all data]

Guye and Mallet, 1902, 2
Guye, P.A.; Mallet, E., Measurement of Critical Constants, Arch. Sci. Phys. Nat., 1902, 13, 274-296. [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]

Ambrose, Ellender, et al., 1976
Ambrose, D.; Ellender, J.H.; Sprake, C.H.S.; Townsend, R., Thermodynamic properties of organic oxygen compounds XLIII. Vapour pressures of some ethers, The Journal of Chemical Thermodynamics, 1976, 8, 2, 165-178, https://doi.org/10.1016/0021-9614(76)90090-2 . [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

Collerson, Counsell, et al., 1965
Collerson, R.R.; Counsell, J.F.; Handley, R.; Martin, J.F.; Sprake, C.H.S., 677. Thermodynamic properties of organic oxygen compounds. Part XV. Purification and vapour pressures of some ketones and ethers, J. Chem. Soc., 1965, 3697, https://doi.org/10.1039/jr9650003697 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Collerson, Counsell, et al., 1965, 2
Collerson, R.R.; Counsell, J.F.; Handley, R.; Martin, J.F.; Sprake, C.H.S., Thermodynamic Properties of Organic Oxygen Compounds. Part XV. Purification and Vapour Pressures of Some Ketones and Ethers, J. Chem. Soc., 1965, 3697-3700, https://doi.org/10.1039/jr9650003697 . [all data]

Dallos, Sisak, et al., 2000
Dallos, A.; Sisak, A.; Kulcsár, Z.; Kováts, E., Pair-wise interactions by gas chromatography VII. Interaction free enthalpies of solutes with secondary alcohol groups, J. Chromatogr. A, 2000, 904, 2, 211-242, https://doi.org/10.1016/S0021-9673(00)00908-0 . [all data]

Righezza, Hassani, et al., 1996
Righezza, M.; Hassani, A.; Meklati, B.Y.; Chrétien, J.R., Quantitative structure-retention relationships (QSRR) of congeneric aromatics series studied on phenyl OV phases in gas chromatography, J. Chromatogr. A, 1996, 723, 1, 77-91, https://doi.org/10.1016/0021-9673(95)00816-0 . [all data]

Hassani and Meklati, 1992
Hassani, A.; Meklati, B.Y., Gas chromatographic behaviour of monosubstituted benzenes, benzaldehydes and acetophenones on OV polymethylphenyl-silicone stationary phases, Chromatographia, 1992, 33, 5/6, 267-271, https://doi.org/10.1007/BF02276193 . [all data]

Reddy, Dutoit, et al., 1992
Reddy, K.S.; Dutoit, J.-Cl.; Kovats, E. sz., Pair-wise interactions by gas chromatography. I. Interaction free enthalpies of solutes with non-associated primary alcohol groups, J. Chromatogr., 1992, 609, 1-2, 229-259, https://doi.org/10.1016/0021-9673(92)80167-S . [all data]

Dutoit, 1991
Dutoit, J., Gas chromatographic retention behaviour of some solutes on structurally similar polar and non-polar stationary phases, J. Chromatogr., 1991, 555, 1-2, 191-204, https://doi.org/10.1016/S0021-9673(01)87179-X . [all data]

Oszczapowicz, Osek, et al., 1985
Oszczapowicz, J.; Osek, J.; Ciszkowski, K.; Krawczyk, W.; Ostrowski, M., Retention Indices of Dimethylbenzamidines and Benzylideneamines on a Non-Polar Column, J. Chromatogr., 1985, 330, 79-85, https://doi.org/10.1016/S0021-9673(01)81964-6 . [all data]

Oszczapowicz, Osek, et al., 1984
Oszczapowicz, J.; Osek, J.; Dolecka, E., Retention indices of dimethylformamidines, dimethylacetamidines and tetramethylguanidines on a non-polar column, J. Chromatogr., 1984, 315, 95-100, https://doi.org/10.1016/S0021-9673(01)90727-7 . [all data]

Tibor and Anna, 1971
Tibor, T.; Anna, B., Gázkromatográfiás retenció és a kémiai szerkezet, I., Magy. Kem. Foly., 1971, 77, 576-587. [all data]

Evans and Smith, 1967
Evans, M.B.; Smith, J.F., Gas chromatography in qualitative analysis. IV. An investigation of the changes in relative rentention data accompanying the oxidation of apolar stationary phases, J. Chromatogr., 1967, 28, 277-284, https://doi.org/10.1016/S0021-9673(01)85968-9 . [all data]

Wehrli and Kováts, 1959
Wehrli, A.; Kováts, E., Gas-chromatographische Charakterisierung ogranischer Verbindungen. Teil 3: Berechnung der Retentionsindices aliphatischer, alicyclischer und aromatischer Verbindungen, Helv. Chim. Acta, 1959, 7, 7, 2709-2736, https://doi.org/10.1002/hlca.19590420745 . [all data]

Song, Lai, et al., 2003
Song, C.; Lai, W.-C.; Madhusudan Reddy, K.; Wei, B., Chapter 7. Temperature-programmed retention indices for GC and GC-MS of hydrocarbon fuels and simulated distillation GC of heavy oils in Analytical advances for hydrocarbon research, Hsu,C.S., ed(s)., Kluwer Academic/Plenum Publishers, New York, 2003, 147-193. [all data]

Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P., Use of incremental models to estimate the retention indexes of aromatic compounds, Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946 . [all data]

Lai and Song, 1995
Lai, W.-C.; Song, C., Temperature-programmed retention indices for g.c. and g.c.-m.s. analysis of coal- and petroleum-derived liquid fuels, Fuel, 1995, 74, 10, 1436-1451, https://doi.org/10.1016/0016-2361(95)00108-H . [all data]

Ebrahimi and Hadjmohammadi, 2006
Ebrahimi, P.; Hadjmohammadi, M.R., Simultaneous modeling of the Kovats retention indices on phenyl OV stationary phases with different polarity using MLR and ANN, QSAR Comb. Sci., 2006, 25, 10, 836-845, https://doi.org/10.1002/qsar.200530145 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References

Symbols used in this document:

C_p,liquid	Constant pressure heat capacity of liquid
P_c	Critical pressure
T_boil	Boiling point
T_c	Critical temperature
T_fus	Fusion (melting) point
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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