4-Heptanone, 2,6-dimethyl-
- Formula: C9H18O
- Molecular weight: 142.2386
- IUPAC Standard InChIKey: PTTPXKJBFFKCEK-UHFFFAOYSA-N
- CAS Registry Number: 108-83-8
- 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: Diisobutyl ketone; s-Diisopropylacetone; DIBK; Isobutyl ketone; Isovalerone; 2,6-Dimethyl-4-heptanone; (iso-C4H9)2CO; 2,6-Dimethylheptan-4-one; Di-isobutylcetone; Diisobutilchetone; Diisobutylketon; 2,6-Dimethyl-heptan-4-on; 2,6-Dimetil-eptan-4-one; sym-Diisopropylacetone; UN 1157; Valerone; NSC 15136; 2,6-dimethyl-4-heptanone (diisobutyl ketone)
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -357.7 ± 1.2 | kJ/mol | Ccr | Seller, 1970 |
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:
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 441. ± 3. | K | AVG | N/A | Average of 15 out of 16 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 231.6 | K | N/A | Anonymous, 1958 | Uncertainty assigned by TRC = 3. K; TRC |
Tfus | 227.0 | K | N/A | Anonymous, 1955 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 227.0 | K | N/A | Doolittle, 1954 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 231.7 | K | N/A | Anonymous, 1953 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 227.11 | K | N/A | Stross, Gable, et al., 1947 | Uncertainty assigned by TRC = 0.07 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 51.0 | kJ/mol | N/A | Ambrose, Ellender, et al., 1975 | Based on data from 322. to 471. K.; AC |
ΔvapH° | 50.92 ± 0.04 | kJ/mol | C | Seller, 1970 | ALS |
ΔvapH° | 50.9 ± 0.1 | kJ/mol | C | Seller, 1970 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
38.600 | 379.3 | N/A | Svoboda, Kubes, et al., 1992 | Value corrected to 298.15 K, obtained by extrapolation.; DH |
49.8 ± 0.1 | 308. | C | Svoboda, Kubes, et al., 1992 | AC |
49.3 ± 0.1 | 313. | C | Svoboda, Kubes, et al., 1992 | AC |
48.4 ± 0.1 | 323. | C | Svoboda, Kubes, et al., 1992 | AC |
47.9 ± 0.1 | 328. | C | Svoboda, Kubes, et al., 1992 | AC |
47.1 ± 0.1 | 338. | C | Svoboda, Kubes, et al., 1992 | AC |
46.6 ± 0.1 | 343. | C | Svoboda, Kubes, et al., 1992 | AC |
46.1 ± 0.1 | 348. | C | Svoboda, Kubes, et al., 1992 | AC |
45.2 ± 0.1 | 358. | C | Svoboda, Kubes, et al., 1992 | AC |
46.8 | 351. | A,MM | Stephenson and Malanowski, 1987 | Based on data from 336. to 451. K. See also Stross, Gable, et al., 1947, 2.; AC |
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:
L - Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.01 ± 0.03 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.98 ± 0.01 | PE | Hernandez, Masclet, et al., 1977 | LLK |
9.04 ± 0.03 | PI | Vilesov, 1960 | RDSH |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1998. |
NIST MS number | 291436 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-1 | 333. | 954.7 | Hu, Lu, et al., 2006 | |
Packed | Apiezon L | 130. | 935. | Wehrli and Kováts, 1959 | Celite; Column length: 2.25 m |
Packed | Apiezon L | 190. | 943. | Wehrli and Kováts, 1959 | Celite; Column length: 2.25 m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Petrocol DH | 962.1 | Censullo, Jones, et al., 2003 | 50. m/0.25 mm/0.5 μm, He, 35. C @ 10. min, 3. K/min, 200. C @ 10. min |
Capillary | DB-1 | 951.2 | Sun and Stremple, 2003 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 40. C; Tend: 325. C |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax | 1189.5 | Censullo, Jones, et al., 2003 | 60. m/0.25 mm/0.5 μm, He, 50. C @ 10. min, 5. K/min, 250. C @ 10. min |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | DC-400 | 150. | 961. | Anderson, 1968 | Helium, Gas-Pak (60-80 mesh); Column length: 3.0 m |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 953. | Zenkevich, Eliseenkov, et al., 2011 | 25. m/0.20 mm/0.25 μm, Nitrogen, 6. K/min; Tstart: 40. C; Tend: 240. C |
Capillary | OV-101 | 956. | Zenkevich and Tsibulskaya, 1989 | Helium, 75. C @ 0. min, 6. K/min, 220. C @ 0. min; Column length: 54. m; Column diameter: 0.26 mm |
Capillary | OV-101 | 956. | Zenkevich and Tsibulskaya, 1989 | Helium, 75. C @ 0. min, 6. K/min, 220. C @ 0. min; Column length: 54. m; Column diameter: 0.26 mm |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 945. | Chen and Feng, 2007 | Program: not specified |
Capillary | Methyl Silicone | 955. | Feng and Mu, 2007 | Program: not specified |
Capillary | SE-30 | 983. | Vinogradov, 2004 | Program: not specified |
Capillary | Methyl Silicone | 955. | Estrada and Gutierrez, 1999 | Program: not specified |
Capillary | OV-1 | 999. | Ramsey and Flanagan, 1982 | Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1178. | Canuti, Conversano, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (4 min) 2.5 0C/min -> 80 0C 5 0C/min -> 110 0C 10 0C/min -> 220 0C (5 min) |
Capillary | DB-Wax | 1207. | Canuti, Conversano, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Capillary | BP-20 | 1162. | Pontes, Marques, et al., 2007 | 30. m/0.25 mm/0.25 μm, He; Program: 50C(1min) => 2.5C/min => 100C => 2C/min => 180C => 15C/min => 220C |
Capillary | Carbowax 20M | 1207. | Vinogradov, 2004 | Program: not specified |
Capillary | Carbowax 20M | 1207. | Ramsey and Flanagan, 1982 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Seller, 1970
Seller, P.,
Enthalpies of formation of some aliphatic branched ketones,
J. Chem. Thermodyn., 1970, 2, 211-219. [all data]
Anonymous, 1958
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 45, Ohio State Univ., 1958. [all data]
Anonymous, 1955
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 45, Tech. Rep. 14, No. 1, Ohio State Univ., 1955. [all data]
Doolittle, 1954
Doolittle, A.K.,
The Technology of Solvents and Plasticizers, Wiley-Inter- science, New York, 1954. [all data]
Anonymous, 1953
Anonymous, R.,
, Physical Properties of Chemical Substances, Dow Chemical Company, 1953. [all data]
Stross, Gable, et al., 1947
Stross, F.H.; Gable, C.M.; Rounds. G.C.,
The Vapor Pressures and Some Other Properties of Diisobutyl Ketone and Diisobutylcarbinol,
J. Am. Chem. Soc., 1947, 69, 1629-30. [all data]
Ambrose, Ellender, et al., 1975
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]
Svoboda, Kubes, et al., 1992
Svoboda, V.; Kubes, V.; Basarova, P.,
Enthalpies of vaporization and cohesive energies of hexan-2-one, 2-methylpentan-4-one, 2,2-dimethylbutan-3-one, 2,6-dimethylheptan-4-one and cyclohexanone,
J. Chem. Thermodynam., 1992, 24, 333-336. [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]
Stross, Gable, et al., 1947, 2
Stross, F.H.; Gable, C.M.; Rounds, G.C.,
The Vapor Pressures and Some Other Properties of Di-i-butyl Ketone and Di-i-butylcarbinol,
J. Am. Chem. Soc., 1947, 69, 7, 1629-1630, https://doi.org/10.1021/ja01199a017
. [all data]
Hernandez, Masclet, et al., 1977
Hernandez, R.; Masclet, P.; Mouvier, G.,
Spectroscopie de photoelectrons d'aldehydes et de cetones aliphatiques,
J. Electron Spectrosc. Relat. Phenom., 1977, 10, 333. [all data]
Vilesov, 1960
Vilesov, F.I.,
The photoionization of vapors of compounds whose molecules contain carbonyl groups,
Dokl. Phys. Chem., 1960, 132, 521, In original 1332. [all data]
Hu, Lu, et al., 2006
Hu, X.-F.; Lu, C.-H.; Yin, C.-S.,
Modeling Gas Chromatographic Retention Indices of Oxygen-containing Compounds by Novel Atom-type Topological Indices,
Chinese Journal of Chemical Physics, 2006, 19, 3, 243-247, https://doi.org/10.1360/cjcp2006.19(3).243.5
. [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]
Censullo, Jones, et al., 2003
Censullo, A.C.; Jones, D.R.; Wills, M.T.,
Speciation of the volatile organic compounds (VOCs) in solventborne aerosol coatings by solid phase microextraction-gas chromatography,
J. Coat. Technol., 2003, 75, 936, 47-53, https://doi.org/10.1007/BF02697922
. [all data]
Sun and Stremple, 2003
Sun, G.; Stremple, P.,
Retention index characterization of flavor, fragrance, and many other compounds on DB-1 and DB-XLB, 2003, retrieved from http://www.chem.agilent.com/cag/cabu/pdf/b-0279.pdf. [all data]
Anderson, 1968
Anderson, D.G.,
USe of Kovats retention indices and response factors for the qualitative and quantitative analysis of coating solvents,
J. Paint Technol., 1968, 40, 527, 549-557. [all data]
Zenkevich, Eliseenkov, et al., 2011
Zenkevich, I.G.; Eliseenkov, E.V.; Kasatochkin, A.N.; Zhakovskaya, Z.A.; Khoroshko, L.O.,
Gas chromatographic identification of chlorination products of aliphatic ketones,
J. Chromatogr., 2011, 1218, 21, 3291-3299, https://doi.org/10.1016/j.chroma.2010.12.056
. [all data]
Zenkevich and Tsibulskaya, 1989
Zenkevich, I.G.; Tsibulskaya, I.A.,
Influence of Relative Amounts of Mixture Components on the Precision of Measurements of Gas Chromatographic Retention Indices,
Zh. Anal. Khim. (Rus.), 1989, 44, 1, 90-96. [all data]
Chen and Feng, 2007
Chen, Y.; Feng, C.,
QSPR study on gas chromatography retention index of some organic pollutants,
Comput. Appl. Chem. (China), 2007, 24, 10, 1404-1408. [all data]
Feng and Mu, 2007
Feng, H.; Mu, L.-L.,
Quantitative structure-retention relationships for alkane and its derivatives based on electrotopological state index and molecular shape index,
Chem. Ind. Engineering (Chinese), 2007, 24, 2, 161-168. [all data]
Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]
Estrada and Gutierrez, 1999
Estrada, E.; Gutierrez, Y.,
Modeling chromatographic parameters by a novel graph theoretical sub-structural approach,
J. Chromatogr. A, 1999, 858, 2, 187-199, https://doi.org/10.1016/S0021-9673(99)00808-0
. [all data]
Ramsey and Flanagan, 1982
Ramsey, J.D.; Flanagan, R.J.,
Detection and Identification of Volatile Organic Compounds in Blood by Headspace Gas Chromatography as an Aid to the Diagnosis of Solvent Abuse,
J. Chromatogr., 1982, 240, 2, 423-444, https://doi.org/10.1016/S0021-9673(00)99622-5
. [all data]
Canuti, Conversano, et al., 2009
Canuti, V.; Conversano, M.; Li Calzi, M.; Heymann, H.; Matthews, M.A.; Ebeler, S.E.,
Headspace solid-phase microextraction - gas chromatography - mass spectrometry for profiling free volatile compounds in Cabernet Sauvignon grapes and vines,
J. Chromatogr. A., 2009, 1216, 15, 3012-3022, https://doi.org/10.1016/j.chroma.2009.01.104
. [all data]
Pontes, Marques, et al., 2007
Pontes, M.; Marques, J.C.; Camara, J.S.,
Screening of volatile composition from Portuguese multifloral honeys using headspace solid-phase microextraction-gas chromatography-quadrupole mass spectrometry,
Talanta, 2007, 74, 1, 91-103, https://doi.org/10.1016/j.talanta.2007.05.037
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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