Ethyl ether

Formula: C₄H₁₀O
Molecular weight: 74.1216
IUPAC Standard InChI: InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3
IUPAC Standard InChIKey: RTZKZFJDLAIYFH-UHFFFAOYSA-N
CAS Registry Number: 60-29-7
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: Ethane, 1,1'-oxybis-; Anaesthetic ether; Anesthesia ether; Anesthetic ether; Diethyl ether; Diethyl oxide; Ethoxyethane; Pronarcol; Solvent ether; 1,1'-Oxybisethane; (C2H5)2O; Aether; Diaethylaether; Dwuetylowy eter; Etere etilico; Ether ethylique; Ether, ethyl; Ethyl ether, tech.; Ethyl oxide; Oxyde d'ethyle; Rcra waste number U117; UN 1155; 3-Oxapentane; Ether; Ethyl ether anhydrous A.C.S.; Sulfuric ether; NSC 100036
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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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-252.7 ± 2.0	kJ/mol	Ccb	Pihlaja and Heikkil, 1968	Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -250.3 ± 1.8 kJ/mol; ALS
Δ_fH°_gas	-252.2 ± 0.79	kJ/mol	Cm	Pilcher, Skinner, et al., 1963	ALS
Δ_fH°_gas	-244.	kJ/mol	Ccb	Murrin and Goldhagen, 1957	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_gas	-2726.3 ± 1.8	kJ/mol	Ccb	Pihlaja and Heikkil, 1968	Corresponding Δ_fHº_gas = -276.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_gas	-2751.1 ± 0.75	kJ/mol	Cm	Pilcher, Skinner, et al., 1963	Corresponding Δ_fHº_gas = -252.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_gas	342.2	J/mol*K	N/A	Counsell J.F., 1971	Other third-law entropy values at 298.15 K are 342.46 [ Cope C.S., 1959], 342.33 [ Stull D.R., 1969], and 342.60 J/mol*K [ Chao J., 1986].; GT

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
62.50	100.	Chao J., 1986	p=1 bar.; GT
84.80	150.
99.70	200.
114.30	273.15
119.46 ± 0.15	298.15
119.86	300.
142.81	400.
165.77	500.
186.35	600.
204.35	700.
220.04	800.
233.74	900.
245.68	1000.
256.08	1100.
265.12	1200.
272.97	1300.
279.81	1400.
285.76	1500.

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
121.94	309.98	Counsell J.F., 1971	Other experimental values of heat capacity [ Jennings W.H., 1934, Jatkar S.K.K., 1939, Valentin F.H.H., 1950] are believed to be less reliable (see [ Chao J., 1986]).; GT
126.57	329.99
131.32	350.00
137.21	375.00
143.27	400.01
149.10	424.99
155.11	450.04

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, References, Notes

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	-271.2 ± 1.9	kJ/mol	Ccb	Murrin and Goldhagen, 1957	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-2732.1 ± 1.9	kJ/mol	Ccb	Murrin and Goldhagen, 1957	Corresponding Δ_fHº_liquid = -271.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	253.5	J/mol*K	N/A	Counsell, Lee, et al., 1971	DH
S°_liquid	252.7	J/mol*K	N/A	Parks, Kelley, et al., 1929	Extrapolation below 90 K, 58.6 J/mol*K. Revision of previous data.; DH
S°_liquid	283.3	J/mol*K	N/A	Parks and Huffman, 1926	Extrapolation below 90 K, 88.70 J/mol*K.; DH

Constant pressure heat capacity of liquid

C_p,liquid (J/mol*K)	Temperature (K)	Reference	Comment
172.5	298.15	Counsell, Lee, et al., 1971	T = 15 to 300 K.; DH
171.88	293.15	Mazur, 1939	T = -112 to 20°C.; DH
172.0	293.	Mazur, 1939, 2	T = -110 to 20°C.; DH
167.4	290.	Kurnakov and Voskresenskaya, 1936	DH
164.8	255.2	Aoyama and Kanda, 1935	T = 80 to 255 K. Value is unsmoothed experimental datum.; DH
179.9	308.	Bennewitz and Wendroth, 1927	T = 308 to 488 K. Value is unsmoothed experimental datum. Pressure 40 atmospheres.; DH
170.7	290.0	Parks and Huffman, 1926	T = 76 to 290 K. Value is unsmoothed experimental datum.; DH
179.1	286.6	Keyes and Beattie, 1924	T = 274, 286 K.; DH

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Notes

Pihlaja and Heikkil, 1968
Pihlaja, K.; Heikkil, J., Heats of combustion. Diethyl ether and 1,1-diethoxyethane, Acta Chem. Scand., 1968, 22, 2731-2732. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

Pilcher, Skinner, et al., 1963
Pilcher, G.; Skinner, H.A.; Pell, A.S.; Pope, A.E., Measurements of heats of combustion by flame calorimetry. Part 1.-Diethyl ether, ethyl vinyl ether and divinyl ether, Trans. Faraday Soc., 1963, 59, 316-330. [all data]

Murrin and Goldhagen, 1957
Murrin, J.W.; Goldhagen, S., Determination of the C-O bond energy from the heats of combustion of four aliphatic ethers, NAVORD Report No. 5491, U.S. Naval Powder Factory Res. & Dev. Dept., 1957, 1-14. [all data]

Counsell J.F., 1971
Counsell J.F., Thermodynamic properties of organic oxygen compounds. Part XXVI. Diethyl ether, J. Chem. Soc. A, 1971, 313-316. [all data]

Cope C.S., 1959
Cope C.S., Equilibria in the hydration of ethylene at elevated pressures and temperatures, A. I. Ch. E. Journal, 1959, 5, 10-16. [all data]

Stull D.R., 1969
Stull D.R., Jr., The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [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]

Jennings W.H., 1934
Jennings W.H., Specific heat of furan and ethyl ether vapors, J. Phys. Chem., 1934, 38, 747-751. [all data]

Jatkar S.K.K., 1939
Jatkar S.K.K., Supersonic velocity in gases and vapors. V. Heat capacity of vapors of acetone, benzene, cyclohexane, hexane and methyl, ethyl and propyl ethers, J. Indian Inst. Sci., 1939, A22, 19-37. [all data]

Valentin F.H.H., 1950
Valentin F.H.H., Equilibrium and thermodynamic relation in the vapor-phase catalytic dehydration of ethyl alcohol to ethyl ether, J. Chem. Soc., 1950, 498-500. [all data]

Counsell, Lee, et al., 1971
Counsell, J.F.; Lee, D.A.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part XXVI. Diethyl ether, 1971, J. [all data]

Parks, Kelley, et al., 1929
Parks, G.S.; Kelley, K.K.; Huffman, H.M., Thermal data on organic compounds. V. A revision of the entropies and free energies of nineteen organic compounds, J. Am. Chem. Soc., 1929, 51, 1969-1973. [all data]

Parks and Huffman, 1926
Parks, G.S.; Huffman, H.M., Thermal data on organic compounds. IV. The heat capacities, entropies and free energies of normal propyl alcohol, ethyl ether and dulcitol, J. Am. Chem. Soc., 1926, 48, 2788-2793. [all data]

Mazur, 1939
Mazur, J., Über die spezifische Wärme des Äthyläthers, Acta Phys. Pol., 1939, 7, 318-326. [all data]

Mazur, 1939, 2
Mazur, J., Über die spezifische Wärme des Äthyläthers, des Nitrobenzols und des Schwefelkohlenstoffs, Z. Physik., 1939, 113, 710-720. [all data]

Kurnakov and Voskresenskaya, 1936
Kurnakov, N.S.; Voskresenskaya, N.K., Calorimetry of liquid binary systems, Izv. Akad. Nauk SSSR, Otdel. Mat. i Estestv. Nauk. Ser. Khim, 1936, 1936, 439-461. [all data]

Aoyama and Kanda, 1935
Aoyama, S.; Kanda, E., Studies on the heat capacities at low temperature. Report I. Heat capacities of some organic substances at low temperature, Sci. Rept. Tohoku Imp. Univ. [1]24, 1935, 107-115. [all data]

Bennewitz and Wendroth, 1927
Bennewitz, K.; Wendroth, H., Untersuchungen im kritischen Gebiet. II. Bestimmung der wahren spezifischen Wärme Cp des flüssigne Äthyläthers oberund unterhalb der kritischen Temperatur, Z. Phys. Chem., 1927, 125, 111-134. [all data]

Keyes and Beattie, 1924
Keyes, F.G.; Beattie, J.A., A calorimeter for measuring specific heats and heats of vaporization of liquids. The specific heat and heat of vaporization of liquid ethyl ether at 0° and 12°, J. Am. Chem. Soc., 1924, 46, 1753-1760. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References

Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
S°_gas	Entropy of gas at standard conditions
S°_liquid	Entropy of liquid at standard conditions
Δ_cH°_gas	Enthalpy of combustion of gas at standard conditions
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

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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