2-Butanone

• Formula: C₄H₈O
• Molecular weight: 72.1057
• IUPAC Standard InChI: InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: ZWEHNKRNPOVVGH-UHFFFAOYSA-N Copy
• 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)
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Vibrational and/or electronic energy levels
  • References
  • Notes
• Other data available:
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

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

Constant pressure heat capacity of liquid

Phase change 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    T_r = reduced temperature (T / T_c)

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Antoine Equation Parameters

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

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Enthalpy of fusion

Entropy of fusion

Reaction 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar

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

C₄H₉O⁺ +  = (C₄H₉O⁺ • )

By formula: C₄H₉O⁺ + C₄H₈O = (C₄H₉O⁺ • C₄H₈O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₅H₁₁O⁺ +  = (C₅H₁₁O⁺ • )

By formula: C₅H₁₁O⁺ + C₄H₈O = (C₅H₁₁O⁺ • C₄H₈O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₄H₇O^- +  =

By formula: C₄H₇O^- + H⁺ = C₄H₈O

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + C₄H₈O = (C₃H₉Sn⁺ • C₄H₈O)

Free energy of reaction

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₄H₈O = (CH₆N⁺ • C₄H₈O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Free energy of reaction

 +  = ( • )

By formula: Cl^- + C₄H₈O = (Cl^- • C₄H₈O)

 +  =

By formula: H₂ + C₄H₈O = C₄H₁₀O

C₄H₇O^- +  =

By formula: C₄H₇O^- + H⁺ = C₄H₈O

 +  = ( • )

By formula: NO^- + C₄H₈O = (NO^- • C₄H₈O)

C₄H₇O^- +  =

By formula: C₄H₇O^- + H⁺ = C₄H₈O

(CAS Reg. No. 35730-33-7 • 4294967295) +  = CAS Reg. No. 35730-33-7

By formula: (CAS Reg. No. 35730-33-7 • 4294967295C₄H₈O) + C₄H₈O = CAS Reg. No. 35730-33-7

=  + 

By formula: C₄H₁₀O = H₂ + C₄H₈O

 +  = ( • )

By formula: Mg⁺ + C₄H₈O = (Mg⁺ • C₄H₈O)

 +  = 2 + 

By formula: C₆H₁₄O₂ + H₂O = 2CH₄O + C₄H₈O

 +  =  + 

By formula: HI + C₄H₇IO = I₂ + C₄H₈O

 +  =

By formula: H₂ + C₄H₆O = C₄H₈O

 +  = ( • )

By formula: Na⁺ + C₄H₈O = (Na⁺ • C₄H₈O)

Henry's Law 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 by: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₄H₈O⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H₇O^- +  =

By formula: C₄H₇O^- + H⁺ = C₄H₈O

C₄H₇O^- +  =

By formula: C₄H₇O^- + H⁺ = C₄H₈O

C₄H₇O^- +  =

By formula: C₄H₇O^- + H⁺ = C₄H₈O

Ion clustering 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
RCD - Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₄H₈O = (CH₆N⁺ • C₄H₈O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Free energy of reaction

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + C₄H₈O = (C₃H₉Sn⁺ • C₄H₈O)

Free energy of reaction

C₄H₉O⁺ +  = (C₄H₉O⁺ • )

By formula: C₄H₉O⁺ + C₄H₈O = (C₄H₉O⁺ • C₄H₈O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₅H₁₁O⁺ +  = (C₅H₁₁O⁺ • )

By formula: C₅H₁₁O⁺ + C₄H₈O = (C₅H₁₁O⁺ • C₄H₈O)

Bond type: Hydrogen bonds of the type OH-O between organics

 +  = ( • )

By formula: Cl^- + C₄H₈O = (Cl^- • C₄H₈O)

 +  = ( • )

By formula: Mg⁺ + C₄H₈O = (Mg⁺ • C₄H₈O)

 +  = ( • )

By formula: NO^- + C₄H₈O = (NO^- • C₄H₈O)

 +  = ( • )

By formula: Na⁺ + C₄H₈O = (Na⁺ • C₄H₈O)

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• GAS (23 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); BECKMAN IR-9 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm^-1 resolution
• SOLUTION (10% IN CCl4 FOR 3800-1300, 10% IN CS2 FOR 1300-650, AND 10% CCl4 FOR 650-250 CM^-1) VERSUS SOLVENT; PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: Tanya L. Myers, Russell G. Tonkyn, Ashley M. Oeck, Tyler O. Danby, John S. Loring, Matthew S. Taubman, Stephen W. Sharpe, Jerome C. Birnbaum, and Timothy J. Johnson

• liquid; Bruker Tensor 27 FTIR; 0.4821395 cm^-1 resolution

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

• gas

Data compiled by: Pamela M. Chu, Franklin R. Guenther, George C. Rhoderick, and Walter J. Lafferty

• gas; IFS66V (Bruker); 3-Term B-H Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); Boxcar Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); Happ Genzel Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); NB Strong Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); Triangular Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution

Mass spectrum (electron ionization)

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

Spectrum

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Additional Data

Vibrational and/or electronic energy levels

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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 by: Takehiko Shimanouchi

Trans form     Symmetry:   C_s     Symmetry Number σ = 1

Source: Shimanouchi, 1972

Notes

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

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

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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
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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]

Wilhoit, Chao, et al., 1985
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Andon, Counsell, et al., 1968, 2
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, 1968, 1894-7. [all data]

Sinke and Oetting, 1964, 2
Sinke, G.C.; Oetting, F.L., The Chemical Thermodynamic Properties of Methyl Ethyl Ketone, J. Phys. Chem., 1964, 68, 1354-8. [all data]

Parks, Kennedy, et al., 1956, 2
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, J. Am. Chem. Soc., 1956, 78, 56-9. [all data]

Kobe, Crawford, et al., 1955
Kobe, K.A.; Crawford, H.R.; Stephenson, R.W., Critical Properties and Vapor Pressures of Some Ketones, Ind. Eng. Chem., 1955, 47, 1767-72. [all data]

Rosenbaum, 1951
Rosenbaum, M., , M.S. Thesis, Univ. Tex., Austin, TX, 1951. [all data]

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Stephenson and Malanowski, 1987
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Ambrose, D.; Ellender, J.H.; Lees, E.B.; Sprake, C.H.S.; Townsend, R., Thermodynamic properties of organic oxygen compounds XXXVIII. Vapour pressures of some aliphatic ketones, The Journal of Chemical Thermodynamics, 1975, 7, 5, 453-472, https://doi.org/10.1016/0021-9614(75)90275-X . [all data]

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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]

Di Cave, Chianese, et al., 1978
Di Cave, Sergio; Chianese, Angelo; Prantera, Antonio, Vapor-liquid equilibrium of the system methylethylketone-sec-butyl alcohol, J. Chem. Eng. Data, 1978, 23, 4, 279-281, https://doi.org/10.1021/je60079a013 . [all data]

Geiseler, Quitzsch, et al., 1973
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Nickerson, Kobe, et al., 1961
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Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Larson and McMahon, 1982
Larson, J.W.; McMahon, T.B., Formation, Thermochemistry, and Relative Stabilities of Proton - Bound dimers of Oxygen n - Donor Bases from Ion Cyclotron Resonance Solvent - Exchange Equilibria Measurements, J. Am. Chem. Soc., 1982, 104, 23, 6255, https://doi.org/10.1021/ja00387a016 . [all data]

Grimsrud and Kebarle, 1973
Grimsrud, E.P.; Kebarle, P., Gas Phase Ion Equilibria Studies of the Solvation of the Hydrogen Ion by Methanol, Dimethyl Ether and Water. Effect of Hydrogen Bonding, J. Am. Chem. Soc., 1973, 95, 24, 7939, https://doi.org/10.1021/ja00805a002 . [all data]

Lias, Liebman, et al., 1984
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Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  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
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy 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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