Ethyl acetoacetate

• Formula: C₆H₁₀O₃
• Molecular weight: 130.1418
• IUPAC Standard InChI: InChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: XYIBRDXRRQCHLP-UHFFFAOYSA-N Copy
• CAS Registry Number: 141-97-9
• 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: Butanoic acid, 3-oxo-, ethyl ester; Acetoacetic acid, ethyl ester; Active acetylacetate; Diacetic ether; Ethyl acetylacetate; Ethyl 3-oxobutanoate; Ethyl 3-oxobutyrate; EAA; Acetoctan ethylnaty; Ethylacetacetat; Ethylester kyseliny acetoctove; 3-Oxobutanoic acid ethyl ester; 1-Ethoxybutane-1,3-dione; NSC 8657
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• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
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  • 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
DRB - Donald R. Burgess, Jr.

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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

 +  =

By formula: C₂H₆O + C₄H₄O₂ = C₆H₁₀O₃

=

By formula: C₆H₁₀O₃ = C₆H₁₀O₃

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, polar column, isothermal

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

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Van Den Dool and Kratz RI, polar column, custom temperature program

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Normal alkane RI, non-polar column, temperature ramp

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

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Normal alkane RI, polar column, custom temperature program

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References

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

Ribeiro da Silva, Ferrao, et al., 1995
Ribeiro da Silva, M.A.V.; Ferrao, M.L.C.C.H.; Jiye, F., Standard molar enthalpy of formation and of vaporization of ethyl 3-oxobutanoate, J. Chem. Eng. Data, 1995, 40, 426-428. [all data]

Vilcu and Perisanu, 1979
Vilcu, R.; Perisanu, S., The standard enthalpies of formation of some C, H, O containing compounds, Rev. Roum. Chim., 1979, 24, 237-243. [all data]

Vilcu, Perisanu, et al., 1975
Vilcu, R.; Perisanu, S.; Ciocazanu, I., Heats of formation in the ideal gas state of some substances containing carbon, hydrogen and oxygen, Conf. Int. Thermodyn. Chim. C.R. 4th, 1975, 1, 105-112. [all data]

Lopatin, Popov, et al., 1992
Lopatin, E.B.; Popov, V.V.; Epshtein, N.A.; Mikhaleva, L.M.; Makarov, Yu.N., Kinetic and thermochemical characteristics of diketene-based reactions, Khim.-Farm. Zh., 1992, 26, 76-78. [all data]

Folkendt, Weiss-Lopez, et al., 1985
Folkendt, M.M.; Weiss-Lopez, B.E.; Chauvel, J.P., Jr.; True, N.S., Gas-phase ¹H NMR studies of keto-enol tautomerism of acetylacetone, methyl acetoacetate, and ethyl acetoacetate, J. Phys. Chem., 1985, 89, 3347-3352. [all data]

Tudor, 1997
Tudor, E., Temperature dependence of the retention index for perfumery compounds on a SE-30 glass capillary column. I. Linear equations, J. Chromatogr. A, 1997, 779, 1-2, 287-297, https://doi.org/10.1016/S0021-9673(97)00453-6 . [all data]

Tiess, 1984
Tiess, D., Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30, Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [all data]

Tudor, Moldovan, et al., 1999
Tudor, E.; Moldovan, D.; Zârna, N., Temperature dependence of the retention index for perfumery compounds on two carbowax-20M glass capillary columns with different film thickness. 2, Rev. Roum. Chim., 1999, 44, 7, 665-675. [all data]

Pino, Mesa, et al., 2005
Pino, J.A.; Mesa, J.; Muñoz, Y.; Martí, M.P.; Marbot, R., Volatile components from mango (Mangifera indica L.) cultivars, J. Agric. Food Chem., 2005, 53, 6, 2213-2223, https://doi.org/10.1021/jf0402633 . [all data]

David, Scanlan, et al., 2000
David, F.; Scanlan, F.; Sandra, P., Retention time locking in flavor analysis, Proceedings 23rd ISCC; CD-ROM, 2000, retrieved from http://www.richrom.com/assets/CD23PDF. [all data]

Bianchi, Careri, et al., 2007
Bianchi, F.; Careri, M.; Mangia, A.; Musci, M., Retention indices in the analysis of food aroma volatile compounds in temperature-programmed gas chromatography: Database creation and evaluation of precision and robustness, J. Sep. Sci., 2007, 39, 4, 563-572, https://doi.org/10.1002/jssc.200600393 . [all data]

Peppard, 1992
Peppard, T.L., Volatile flavor constituents of Monstera deliciosa, J. Agric. Food Chem., 1992, 40, 2, 257-262, https://doi.org/10.1021/jf00014a018 . [all data]

Ádámová, Orinák, et al., 2005
Ádámová, M.; Orinák, A.; Halás, L., Retention indices as identification tool in pyrolysis-capillary gas chromatography, J. Chromatogr. A, 2005, 1087, 1-2, 131-141, https://doi.org/10.1016/j.chroma.2005.01.003 . [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

David, Scanlan, et al., 2002
David, F.; Scanlan, F.; Sandra, P.; Szelewski, M., Analysis of essential oil compounds using retention time locked methods and retention time databases, 2002, retrieved from http://www.chem.agilent.com. [all data]

Jordán, Goodner, et al., 2002
Jordán, M.J.; Goodner, K.L.; Shaw, P.E., Characterization of the aromatic profile in aqueous essence and fruit juice of yellow passion fruit (Passiflora edulis Sims F. Flavicarpa degner) by GC-MS and GC/O, J. Agric. Food Chem., 2002, 50, 6, 1523-1528, https://doi.org/10.1021/jf011077p . [all data]

Notes

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• Symbols used in this document:
  

  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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