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2-Oxetanone, 4-methylene-

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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

Quantity Value Units Method Reference Comment
Deltafgas-190.2 ± 0.54kJ/molCcrMansson, Nakase, et al., 1968ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
36.2750.Thermodynamics Research Center, 1997p=1 bar. Selected entropy and heat capacity at 298.15 K are in close agreement with statistical values calculated by [ Joshi R.M., 1970]. However entropy values at 600 and 1000 K obtained by [ Joshi R.M., 1970] are about 27 J/mol*K lower than selected ones. Estimations by difference method [ Dorofeeva O.V., 1997] give preference for data [ Thermodynamics Research Center, 1997].; GT
42.49100.
50.94150.
61.35200.
78.44273.15
84.41298.15
84.84300.
107.35400.
126.33500.
141.71600.
154.21700.
164.49800.
173.06900.
180.271000.
186.41100.
191.61200.
196.01300.
199.91400.
203.21500.

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

Quantity Value Units Method Reference Comment
Deltafliquid-233.1 ± 0.46kJ/molCcrMansson, Nakase, et al., 1968 
Quantity Value Units Method Reference Comment
Deltacliquid-1912.5 ± 0.42kJ/molCcrMansson, Nakase, et al., 1968Corresponding «DELTA»fliquid = -233.1 kJ/mol (simple calculation by NIST; no Washburn corrections)

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, Kenneth Kroenlein 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
Tboil400.6KN/AWeast and Grasselli, 1989BS
Tboil399.2KN/AMajer and Svoboda, 1985 
Tboil400.15KN/AAnonymous, 1968TRC
Quantity Value Units Method Reference Comment
Tfus266.15KN/AAnonymous, 1968Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Deltavap42.9kJ/molN/AMajer and Svoboda, 1985 
Deltavap42.9 ± 0.1kJ/molCMansson, Nakase, et al., 1968ALS
Deltavap42.9kJ/molN/AMansson, Nakase, et al., 1968DRB
Deltavap42.9 ± 0.1kJ/molCMansson, Nakase, et al., 1968AC

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
342.70.133Aldrich Chemical Company Inc., 1990BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
36.8399.2N/AMajer and Svoboda, 1985 
42.9312.AStephenson and Malanowski, 1987Based on data from 297. - 388. K.; AC

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

2-Oxetanone, 4-methylene- + Ammonia = acetoacetamide

By formula: C4H4O2 + H3N = acetoacetamide

Quantity Value Units Method Reference Comment
Deltar-173.0kJ/molKinLopatin, Popov, et al., 1992liquid phase; solvent: Solution

2-Oxetanone, 4-methylene- + Water = Butanoic acid, 3-oxo-

By formula: C4H4O2 + H2O = C4H6O3

Quantity Value Units Method Reference Comment
Deltar-118.5kJ/molKinLopatin, Popov, et al., 1992liquid phase; solvent: Solution

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

Urea + 2-Oxetanone, 4-methylene- = N-(aminocarbonyl)-3-oxobutyramide

By formula: CH4N2O + C4H4O2 = N-(aminocarbonyl)-3-oxobutyramide

Quantity Value Units Method Reference Comment
Deltar-106.4kJ/molKinLopatin, Popov, et al., 1992liquid phase; solvent: Solution

22-Oxetanone, 4-methylene- = Dehydroacetic Acid

By formula: 2C4H4O2 = C8H8O4

Quantity Value Units Method Reference Comment
Deltar-91.9kJ/molKinLopatin, Popov, et al., 1992liquid phase; solvent: Solution

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 compiled by: Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

Ionization energy determinations

IE (eV) Method Reference
9.6 ± 0.02EIOlivares, Flesch, et al., 1984

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H4O+10.0 ± 0.04COEIOlivares, Flesch, et al., 1984 

IR 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: Coblentz Society, Inc.

Condensed Phase Spectrum

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IR spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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Owner COBLENTZ SOC.
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin DOW CHEMICAL COMPANY
Source reference COBLENTZ NO. 07595
Date 1965/02/10
Name(s) 4-methylene-2-oxetanone
State SOLUTION (CS2 FOR 3800-400 CM-1)
Instrument BECKMAN IR-9 (GRATING)
Instrument parameters ORDER CHANGES: 670, 1200, 2000 CM-1
Path length 0.10 CM
SPECTRAL CONTAMINATION DUE TO CS2 AROUND 2800, 2300, 1600-1400, 850, 650 CM-1
Resolution 2
Sampling procedure TRANSMISSION
Data processing DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY

This IR spectrum is from the Coblentz Society's evaluated infrared reference spectra collection.


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 NIST Mass Spectrometry Data Center
NIST MS number 334003

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.


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

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

View large format table.

Column type Active phase I Reference Comment
CapillaryVF-5MS709.2Tret'yakov, 200730. m/0.25 mm/0.25 «mu»m, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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.

Mansson, Nakase, et al., 1968
Mansson, M.; Nakase, Y.; Sunner, S., The enthalpies of combustion and formation of diketene, Acta Chem. Scand., 1968, 22, 171-174. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Joshi R.M., 1970
Joshi R.M., Thermodynamic properties of some monomeric compounds in the standard ideal gas state, J. Polym. Sci., Part A-2, 1970, 8, 679-687. [all data]

Dorofeeva O.V., 1997
Dorofeeva O.V., Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [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]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

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

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 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]

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]

Olivares, Flesch, et al., 1984
Olivares, J.A.; Flesch, G.D.; Svec, H.J., Mass spectrometry of five ketene dimers, Int. J. Mass Spectrom. Ion Processes, 1984, 56, 293. [all data]

Tret'yakov, 2007
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]


Notes

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