2-Butanone

Formula: C₄H₈O
Molecular weight: 72.1057
IUPAC Standard InChI: InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3
IUPAC Standard InChIKey: ZWEHNKRNPOVVGH-UHFFFAOYSA-N
CAS Registry Number: 78-93-3
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: Butan-2-one; Butanone; Ethyl methyl ketone; Ketone, methyl ethyl; Methyl ethyl ketone; MEK; C2H5COCH3; Acetone, methyl-; Aethylmethylketon; 3-Butanone; Butanone 2; Ethyl methyl cetone; Ethylmethylketon; Ketone, ethyl methyl; Meetco; Methyl acetone; Metiletilchetone; Metyloetyloketon; Rcra waste number U159; UN 1193; 2-Oxobutane; 2-Butanal; 2-butanone (MEK; methyl ethyl ketone); 2-butanone (MEK)
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Gas phase thermochemistry data

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

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	-57.02 ± 0.20	kcal/mol	Cm	Chao and Zwolinski, 1976	ALS
Δ_fH°_gas	-57.05 ± 0.23	kcal/mol	Eqk	Buckley and Herington, 1965	Reanalyzed by Cox and Pilcher, 1970, Original value = -56.89 kcal/mol; ALS
Δ_fH°_gas	-56.90	kcal/mol	Ccb	Sinke and Oetting, 1964	ALS

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
13.63	100.	Chao J., 1986	p=1 bar. Recommended values agree with results of statistical calculations [ Sinke G.C., 1964, Chao J., 1976] within 0.2-1.8 J/molK. S(T) values calculated by [ Nickerson J.K., 1961] are different from selected ones by 4-5 J/molK.; GT
16.49	150.
19.17	200.
22.97	273.15
24.302 ± 0.033	298.15
24.400	300.
29.725	400.
34.668	500.
38.994	600.
42.727	700.
45.949	800.
48.736	900.
51.145	1000.
53.224	1100.
55.022	1200.
56.573	1300.
57.913	1400.
59.075	1500.

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
27.110 ± 0.055	347.15	von Geiseler G., 1973	Experimental data [ Vilcu R., 1975] differ appreciably from data selected here. Their correctness seems to be doubtful (see [ Kabo G.J., 1995]). Low accuracy is also expected for experimental value of Cp(410 K)=123.85 J/mol*K [ Bennewitz K., 1938]. Please also see Nickerson J.K., 1961.; GT
27.641 ± 0.041	358.79
28.370 ± 0.043	371.90
28.449 ± 0.057	372.15
29.099 ± 0.043	385.60
29.730 ± 0.060	397.15
29.780 ± 0.045	399.55
30.349 ± 0.045	410.70
31.479 ± 0.062	432.15
33.131 ± 0.067	467.15

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	-65.31 ± 0.29	kcal/mol	Ccb	Sinke and Oetting, 1964	ALS
Δ_fH°_liquid	-66.68	kcal/mol	Ccb	Parks, Mosley, et al., 1950	see Moore, Renquist, et al., 1940; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-584.17	kcal/mol	Ccb	Sinke and Oetting, 1964	Corresponding Δ_fHº_liquid = -65.29 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-582.80	kcal/mol	Ccb	Parks, Mosley, et al., 1950	see Moore, Renquist, et al., 1940; Corresponding Δ_fHº_liquid = -66.66 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-582.28 ± 0.37	kcal/mol	Ccb	Crog and Hunt, 1942	Corresponding Δ_fHº_liquid = -67.18 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	57.12	cal/mol*K	N/A	Andon, Counsell, et al., 1968	DH
S°_liquid	57.079	cal/mol*K	N/A	Sinke and Oetting, 1964	DH
S°_liquid	57.70	cal/mol*K	N/A	Parks, Kennedy, et al., 1956	Extrapolation below 80 K, 53.47 J/mol*K.; DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
38.0	298.15	Malhotra and Woolf, 1992	T = 278 to 338 K. p = 0.1 MPa.; DH
38.77	303.15	Reddy, 1986	T = 303.15, 313.15 K.; DH
37.86	298.15	Costas and Patterson, 1985	T = 283.15, 298.15, 313.15 K.; DH
37.86	298.15	Costas and Patterson, 1985, 2	DH
37.741	298.15	Grolier and Benson, 1984	DH
37.86	298.1	Roux, Perron, et al., 1978	T = 277 to 313 K.; DH
38.05	298.15	Grolier, Benson, et al., 1975	DH
37.93	298.15	Andon, Counsell, et al., 1968	T = 10 to 320 K.; DH
37.76	293.	Rastorguev and Ganiev, 1967	T = 293 to 353 K.; DH
37.980	298.15	Sinke and Oetting, 1964	T = 13 to 308 K.; DH
37.861	298.15	Parks, Kennedy, et al., 1956	T = 80 to 300 K.; DH
38.41	297.0	Kolosovskii and Udovenko, 1934	DH
38.41	297.0	de Kolossowsky and Udowenko, 1933	DH

References

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

Chao and Zwolinski, 1976
Chao, J.; Zwolinski, B.J., Ideal gas thermodynamic properties of propanone and 2-butanone, J. Phys. Chem. Ref. Data, 1976, 5, 319-328. [all data]

Buckley and Herington, 1965
Buckley, E.; Herington, E.F.G., Equilibria in some secondary alcohol + hydrogen + ketone systems, Trans. Faraday Soc., 1965, 61, 1618-1625. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Sinke and Oetting, 1964
Sinke, G.C.; Oetting, F.L., The chemical thermodynamic properties of methyl ethyl ketone, J. Phys. Chem., 1964, 68, 1354-1358. [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]

Sinke G.C., 1964
Sinke G.C., The chemical thermodynamic properties of methyl ethyl ketone, J. Phys. Chem., 1964, 68, 1354-1358. [all data]

Chao J., 1976
Chao J., Ideal gas thermodynamic properties of propanone and 2-butanone, J. Phys. Chem. Ref. Data, 1976, 5, 319-328. [all data]

Nickerson J.K., 1961
Nickerson J.K., The thermodynamic properties of the methyl ketone series, J. Phys. Chem., 1961, 65, 1037-1043. [all data]

von Geiseler G., 1973
von Geiseler G., The heat capacity and the heat of vaporization of isomeric butylmethylketones and propylacetates, Z. Phys. Chem. (Leipzig), 1973, 252, 170-176. [all data]

Vilcu R., 1975
Vilcu R., Determination of heat capacities of some alcohols and ketones in vapor phase, Rev. Roum. Chim., 1975, 20, 603-609. [all data]

Kabo G.J., 1995
Kabo G.J., Thermodynamic properties, conformation, and phase transitions of cyclopentanol, J. Chem. Thermodyn., 1995, 27, 953-967. [all data]

Bennewitz K., 1938
Bennewitz K., Molar heats of vapor organic compounds, Z. Phys. Chem. (Leipzig), 1938, B39, 126-144. [all data]

Parks, Mosley, et al., 1950
Parks, G.S.; Mosley, J.R.; Peterson, P.V., Jr., Heats of combustion and formation of some organic compounds containing oxygen, J. Chem. Phys., 1950, 18, 152. [all data]

Moore, Renquist, et al., 1940
Moore, G.E.; Renquist, M.L.; Parks, G.S., Thermal data on organic compounds. XX. Modern combustion data for two methylnonanes, methyl ethyl ketone, thiophene and six cycloparaffins, J. Am. Chem. Soc., 1940, 62, 1505-1507. [all data]

Crog and Hunt, 1942
Crog, R.S.; Hunt, H., Heats of combustion. II. The heats of combustion of ethyl methyl ketone and ethylene oxide, J. Phys. Chem., 1942, 46, 1162-1163. [all data]

Andon, Counsell, et al., 1968
Andon, R.J.L.; Counsell, J.F.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part XX. The low-temperature heat capacity and entropy of C₄ and C₅ ketones, J. Chem. Soc. A, 1968, 1894-1897. [all data]

Parks, Kennedy, et al., 1956
Parks, G.S.; Kennedy, W.D.; Gates, R.R.; Mosley, J.R.; Moore, G.E.; Renquist, M.L., Thermal data on organic compounds. XXVI. Some heat capacity, entropy and free energy data for seven compounds containing oxygen., Not In System, 1956, 78, 56-59. [all data]

Malhotra and Woolf, 1992
Malhotra, R.; Woolf, L.A., Thermodynamic properties of butan-2-one at temperatures from 278 to 338 K and pressures from 0.1 MPa to 280 MPa; predictions for higher ketones, J. Chem. Thermodynam., 1992, 24, 1207-1217. [all data]

Reddy, 1986
Reddy, K.S., Isentropic compressibilities of binary liquid mixtures at 303.15 and 313.15 K, J. Chem. Eng. Data, 1986, 31, 238-240. [all data]

Costas and Patterson, 1985
Costas, M.; Patterson, D., Heat capacities of water + organic-solvent mixtures, J. Chem. Soc., Faraday Trans. 1, 1985, 81, 2381-2398. [all data]

Costas and Patterson, 1985, 2
Costas, M.; Patterson, D., Self-association of alcohols in inert solvents, J. Chem. Soc., Faraday Trans. 1, 1985, 81, 635-654. [all data]

Grolier and Benson, 1984
Grolier, J.-P.E.; Benson, G.C., Thermodynamic properties of binary mixtures containing ketones. VIII. Heat capacities and volumes of some n-alkanone + n-alkane mixtures at 298.15 K, Can. J. Chem., 1984, 62, 949-953. [all data]

Roux, Perron, et al., 1978
Roux, G.; Perron, G.; Desnoyers, J.E., The heat capacities and volumes of some low molecular weight amides, ketones, esters, and ethers in water over the whole solubility range, Can. J. Chem., 1978, 56, 2808-2814. [all data]

Grolier, Benson, et al., 1975
Grolier, J-P.E.; Benson, G.C.; Picker, P., Simultaneous measurements of heat capacities and densities of organic liquid mixtures-systems containing ketones, J. Chem. Eng. Data, 1975, 20, 243-246. [all data]

Rastorguev and Ganiev, 1967
Rastorguev, Yu.L.; Ganiev, Yu.A., Study of the heat capacity of selected solvents, Izv. Vyssh. Uchebn. Zaved. Neft Gaz. 10, 1967, No.1, 79-82. [all data]

Kolosovskii and Udovenko, 1934
Kolosovskii, N.A.; Udovenko, W.W., Specific heat of liquids. II., Zhur. Obshchei Khim., 1934, 4, 1027-1033. [all data]

de Kolossowsky and Udowenko, 1933
de Kolossowsky, N.A.; Udowenko, W.W., Mesure des chaleurs specifique moleculaires de quelques liquides, Compt. rend., 1933, 197, 519-520. [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°_liquid	Entropy of liquid 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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