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Ethyl acetoacetate

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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.

Quantity Value Units Method Reference Comment
Deltafgas-586.2 ± 1.5kJ/molCcbRibeiro da Silva, Ferrao, et al., 1995ALS
Deltafgas-558.0kJ/molN/AVilcu and Perisanu, 1979Value computed using «DELTA»fHliquid° value of -612.2±5.4 kj/mol from Vilcu and Perisanu, 1979 and «DELTA»vapH° value of 54.2 kj/mol from Ribeiro da Silva, Ferrao, et al., 1995.; DRB
Deltafgas-507.5kJ/molN/AVilcu, Perisanu, et al., 1975Value computed using «DELTA»fHliquid° value of -561.7 kj/mol from Vilcu, Perisanu, et al., 1975 and «DELTA»vapH° value of 54.2 kj/mol from Ribeiro da Silva, Ferrao, et al., 1995.; DRB

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

Quantity Value Units Method Reference Comment
Deltafliquid-640.4 ± 1.1kJ/molCcbRibeiro da Silva, Ferrao, et al., 1995ALS
Deltafliquid-612.2 ± 5.4kJ/molCcbVilcu and Perisanu, 1979ALS
Deltafliquid-561.70kJ/molCcbVilcu, Perisanu, et al., 1975ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3149.76 ± 0.76kJ/molCcbRibeiro da Silva, Ferrao, et al., 1995Corresponding «DELTA»fliquid = -640.45 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-3178.1 ± 7.7kJ/molCcbVilcu and Perisanu, 1979Corresponding «DELTA»fliquid = -612.08 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-3153.kJ/molCcbGuinchant, 1918Corresponding «DELTA»fliquid = -637.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
250.2297.5Kolosovskii and Udovenko, 1934DH
246.9297.5de Kolossowsky and Udowenko, 1933DH
241.8298.von Reis, 1881T = 288 to 455 K.; DH

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil453.8 ± 0.5KAVGN/AAverage of 10 out of 11 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus230.15KN/AAnonymous, 1968TRC
Quantity Value Units Method Reference Comment
Deltavap54.18 ± 0.96kJ/molCRibeiro da Silva, Ferrao, et al., 1995ALS
Deltavap54.2kJ/molN/ARibeiro da Silva, Ferrao, et al., 1995DRB
Deltavap54.2 ± 1.0kJ/molCRibeiro da Silva, Ferrao, et al., 1995AC
Deltavap50.54kJ/molVVilcu, Perisanu, et al., 1975ALS

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
347.20.019Weast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
52.5316.AStephenson and Malanowski, 1987Based on data from 301. - 454. K.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
301.7 - 454.05.163272189.547-29.184Stull, 1947Coefficents calculated by NIST from author's data.

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

Ethanol + 2-Oxetanone, 4-methylene- = Ethyl acetoacetate

By formula: C2H6O + C4H4O2 = C6H10O3

Quantity Value Units Method Reference Comment
Deltar-127.0kJ/molKinLopatin, Popov, et al., 1992liquid phase; solvent: Solution

Ethyl acetoacetate = 2-Butenoic acid, 2-hydroxy-, ethyl ester

By formula: C6H10O3 = C6H10O3

Quantity Value Units Method Reference Comment
Deltar-13.3 ± 1.0kJ/molEqkFolkendt, Weiss-Lopez, et al., 1985gas phase; NMR

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)

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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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Mass 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 Japan AIST/NIMC Database- Spectrum MS-NW-1297
NIST MS number 227788

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Dayton, 1954
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 3015
Instrument n.i.g.
Melting point -45
Boiling point 180.8

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, NIST Free Links, 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

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Column type Active phase Temperature (C) I Reference Comment
CapillarySE-30100.903.0Tudor, 199740. m/0.35 mm/0.35 «mu»m
PackedSE-30150.910.Tiess, 1984Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m

Kovats' RI, polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryCarbowax 20M150.1496.Tudor, Moldovan, et al., 1999Phase thickness: 0.08 «mu»m

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

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Column type Active phase I Reference Comment
CapillaryHP-5MS954.Pino, Mesa, et al., 200530. m/0.25 mm/0.25 «mu»m, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min
CapillaryHP-5944.David, Scanlan, et al., 200050. m/0.32 mm/1.05 «mu»m, He, 2. K/min; Tstart: 50. C; Tend: 290. C

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

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Column type Active phase I Reference Comment
CapillarySupelcowax-101466.Bianchi, Careri, et al., 200730. m/0.25 mm/0.25 «mu»m, He; Program: 35C(8min) => 4C/min => 60C => 6C/min => 160C => 20C/min => 200C(1min)

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryDB-1907.Peppard, 199230. m/0.25 mm/1.0 «mu»m, He, 3. K/min, 250. C @ 30. min; Tstart: 40. C

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

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Column type Active phase I Reference Comment
CapillaryRTX-5910.Ádámová, Orinák, et al., 200530. m/0.25 mm/0.25 «mu»m, N2; Program: not specified
CapillarySE-30907.Vinogradov, 2004Program: not specified
CapillaryHP-5944.4David, Scanlan, et al., 200250. m/0.32 mm/1.05 «mu»m, He; Program: not specified
CapillaryHP-5943.Jordán, Goodner, et al., 200230. m/0.25 mm/0.25 «mu»m; Program: not specified
CapillaryHP-5930.Jordán, Goodner, et al., 200230. m/0.25 mm/0.25 «mu»m; Program: not specified

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryCarbowax 20M1427.Vinogradov, 2004Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, Notes

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]

Guinchant, 1918
Guinchant, M.J., Etude sur la fonction acide dans les derives metheniques et methiniques, Ann. Chem., 1918, 10, 30-84. [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]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Anonymous, 1968
Anonymous, X., Chemicals and Plastics Physical Properties, 1968, Union Carbide Corp., product bulletin, 1968. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

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]

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]

Dayton, 1954
Dayton, P.G., L'absorption dans l'ultraviolet moyen de certains esters «beta»-cetoniques et de certains de leurs derives azotes, Compt. Rend., 1954, 238, 2316-2318. [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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References