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Butanedioic acid, dimethyl ester

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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
Deltacsolid-2959.kJ/molCcbVerkade, Coops, et al., 1926Heat of combustion at 15°C; Corresponding «DELTA»fsolid = -831.8 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
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil470. ± 3.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus292. ± 1.KAVGN/AAverage of 11 values; Individual data points
Quantity Value Units Method Reference Comment
Deltavap61.0 ± 0.3kJ/molGSVerevkin, Kozlova, et al., 2006Based on data from 286. - 340. K.; AC
Deltavap61.7 ± 0.4kJ/molN/AKatayama, 1992Based on data from 342. - 468. K. See also Verevkin, Kozlova, et al., 2006.; AC
Deltavap60.9 ± 0.4kJ/molEBDaubert, Jalowka, et al., 1987Based on data from 367. - 460. K. See also Verevkin, Kozlova, et al., 2006.; AC
Deltavap62.4kJ/molEBVlasov, Granzhan, et al., 1963Based on data from 398. - 468. K. See also Verevkin, Kozlova, et al., 2006.; AC

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
353.20.015Weast and Grasselli, 1989BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
49.3364.AStephenson and Malanowski, 1987Based on data from 340. - 470. 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

Hydrogen + 2-Butenedioic acid (Z)-, dimethyl ester = Butanedioic acid, dimethyl ester

By formula: H2 + C6H8O4 = C6H10O4

Quantity Value Units Method Reference Comment
Deltar-446.9kJ/molChydVeselova and Sul'man, 1980liquid phase

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

Gas Phase Spectrum

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

Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


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

View image of digitized spectrum (can be printed in landscape orientation).

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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 291372

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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillarySE-54140.1029.Grigor'eva, Vasil'ev, et al., 199315. m/0.28 mm/2.4 «mu»m, Ar
CapillarySE-54160.1027.Grigor'eva, Vasil'ev, et al., 199315. m/0.28 mm/2.4 «mu»m, Ar
CapillarySE-54180.1026.Grigor'eva, Vasil'ev, et al., 199315. m/0.28 mm/2.4 «mu»m, Ar
CapillaryUltra-1100.997.Herrmann, Dufka, et al., 198625. m/0.20 mm/0.32 «mu»m, N2
CapillaryUltra-1125.995.Herrmann, Dufka, et al., 198625. m/0.20 mm/0.32 «mu»m, N2
CapillaryUltra-1150.994.Herrmann, Dufka, et al., 198625. m/0.20 mm/0.32 «mu»m, N2
CapillaryUltra-175.999.Herrmann, Dufka, et al., 198625. m/0.20 mm/0.32 «mu»m, N2

Kovats' RI, polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryPEG-40M120.1566.Grigor'eva, Vasil'ev, et al., 199340. m/0.25 mm/0.10 «mu»m, Ar
CapillaryPEG-40M120.1580.Grigor'eva, Vasil'ev, et al., 199340. m/0.25 mm/0.10 «mu»m, Ar

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

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Column type Active phase I Reference Comment
CapillaryOV-11004.Tan, Holland, et al., 1988He, 8. K/min, 280. C @ 10. min; Column length: 25. m; Column diameter: 0.32 mm; Tstart: 40. C
CapillaryDB-51034.Rostad and Pereira, 198630. m/0.26 mm/0.25 «mu»m, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min
PackedSE-301000.van den Dool and Kratz, 1963Celite; Tstart: 75. C; Tend: 228. C

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

View large format table.

Column type Active phase I Reference Comment
CapillaryVF-5MS1035.5Tret'yakov, 200830. m/0.25 mm/0.25 «mu»m, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C

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

View large format table.

Column type Active phase I Reference Comment
CapillaryZB-Wax1595.Ledauphin, Saint-Clair, et al., 200430. m/0.25 mm/0.15 «mu»m, He, 35. C @ 5. min, 5. K/min, 220. C @ 10. min
PackedCarbowax 20M1576.van den Dool and Kratz, 1963Celite 545, 4.6 K/min; Tstart: 75. C; Tend: 228. C

Normal alkane RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryOV-101120.1012.Lipp, Krasnykh, et al., 2008Helium; Column length: 50. m; Column diameter: 0.25 mm
CapillaryOV-101130.1014.Lipp, Krasnykh, et al., 2008Helium; Column length: 50. m; Column diameter: 0.25 mm
CapillaryOV-101140.1015.Lipp, Krasnykh, et al., 2008Helium; Column length: 50. m; Column diameter: 0.25 mm
CapillaryOV-101150.1017.Lipp, Krasnykh, et al., 2008Helium; Column length: 50. m; Column diameter: 0.25 mm

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryUltra-ALLOY-51034.Tsuge, Ohtan, et al., 201130. m/0.25 mm/0.25 «mu»m, 40. C @ 2. min, 20. K/min, 320. C @ 13. min
CapillaryHP-11004.Peters, de Leer, et al., 199425. m/0.2 mm/0.33 «mu»m, He, 50. C @ 5. min, 8. K/min, 300. C @ 10. min
CapillaryUltra-11000.Okumura, 199125. m/0.32 mm/0.25 «mu»m, He, 3. K/min; Tstart: 80. C; Tend: 260. C
CapillaryOV-101996.Pinkston, Spiteller, et al., 1981H2, 80. C @ 7. min, 2. K/min; Column length: 30. m; Column diameter: 0.3 mm; Tend: 275. C
CapillaryOV-101996.Spiteller and Spiteller, 1979He, 75. C @ 7. min, 2. K/min; Column length: 25. m; Tend: 280. C

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

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Column type Active phase I Reference Comment
CapillaryNonpolar1030.Staples and Zeiger, 2008Program: not specified
CapillaryNonpolar1032.Staples and Zeiger, 2008Program: not specified
CapillaryNonpolar1034.Staples and Zeiger, 2008Program: not specified
CapillaryDB-5 MS1035.Watanabe, Ueda, et al., 200830. m/0.32 mm/1.0 «mu»m, Helium; Program: -10 0C (3 min) 50 0C/min -> 40 0C 5 0C/min -> 290 0C (5 min)
CapillarySE-301002.Vinogradov, 2004Program: not specified
CapillaryHP-11009.Rowland, Blackman, et al., 199525. m/0.25 mm/0.25 «mu»m; Program: 30 0C (4 min) 6 K/min -> 200 0C 15 K/min -> 250 0C (20 min)

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1526.Guo, Wu, et al., 200830. m/0.25 mm/0.25 «mu»m, Helium, 60. C @ 2. min, 10. K/min, 250. C @ 10. min
CapillaryTC-Wax1568.Suhardi, Suzuki, et al., 200260. m/0.25 mm/0.25 «mu»m, He, 40. C @ 10. min, 3. K/min, 230. C @ 10. min

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryCarbowax 20M1558.Vinogradov, 2004Program: not specified

Lee's RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryDB-5169.29Rostad and Pereira, 198630. m/0.26 mm/0.25 «mu»m, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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.

Verkade, Coops, et al., 1926
Verkade, P.E.; Coops, J.; Hartman, H., Calorimetric researches. XIII. Heats of combustion of successive terms of homologous series: Dimethyl esters of the oxalic acid series. A general survey of the oscillation phenomena, Recl. Trav. Chim. Pays-Bas, 1926, 45, 585-606. [all data]

Verevkin, Kozlova, et al., 2006
Verevkin, Sergey P.; Kozlova, Svetlana A.; Emel'yanenko, Vladimir N.; Nikitin, Eugene D.; Popov, Alexander P.; Krasnykh, Eugen L., Vapor Pressures, Enthalpies of Vaporization, and Critical Parameters of a Series of Linear Aliphatic Dimethyl Esters of Dicarboxylic Acids, J. Chem. Eng. Data, 2006, 51, 5, 1896-1905, https://doi.org/10.1021/je0602418 . [all data]

Katayama, 1992
Katayama, Hirotake, Measurement and estimation of vapor pressures of dimethyl, diethyl, diisopropyl and dibutyl succinates at reduced pressure., J. Chem. Eng. Japan / JCEJ, 1992, 25, 4, 366-372, https://doi.org/10.1252/jcej.25.366 . [all data]

Daubert, Jalowka, et al., 1987
Daubert, T.E.; Jalowka, J.W.; Goren, V., AIChE Symp. Ser., 1987, 83, 128. [all data]

Vlasov, Granzhan, et al., 1963
Vlasov, O.N.; Granzhan, V.A.; Savenko, L.M., Zh. Prikl. Khim., 1963, 36, 2311. [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]

Veselova and Sul'man, 1980
Veselova, M.E.; Sul'man, E.M., Effect of the chemical structure of «alpha»,«beta»-unsaturated esters and ketones on the selectivity of their hydrogenation, Svoistva Veshchestv i Stroenie Molekul, Kalinin, 1980, 140-143. [all data]

Grigor'eva, Vasil'ev, et al., 1993
Grigor'eva, D.N.; Vasil'ev, A.V.; Golovnya, R.V., Effect of the temperature on the retention indices in homologous series of bifunctional compounds under capillary gas chromatography conditions, J. Anal. Chem. USSR (Engl. Transl.), 1993, 48, 7, 817-822. [all data]

Herrmann, Dufka, et al., 1986
Herrmann, F.; Dufka, O.; Churacek, J., Fused-Silica Capillary Gas Chromatography-Mass Spectrometry of Some Dicarboxylic Acids Present in Condensation-Type Polymers I. Dimethyl Esters, J. Chromatogr., 1986, 360, 79-88, https://doi.org/10.1016/S0021-9673(00)91653-4 . [all data]

Tan, Holland, et al., 1988
Tan, S.-T.; Holland, P.T.; Wilkins, A.L.; Molan, P.C., Extractives from New Zealand honeys. 1. White clovers, manuka, and kanuka unifloral honeys, J. Agric. Food Chem., 1988, 36, 3, 453-460, https://doi.org/10.1021/jf00081a012 . [all data]

Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E., Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603 . [all data]

van den Dool and Kratz, 1963
van den Dool, H.; Kratz, P. Dec., A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography, J. Chromatogr., 1963, 11, 463-471, https://doi.org/10.1016/S0021-9673(01)80947-X . [all data]

Tret'yakov, 2008
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2008. [all data]

Ledauphin, Saint-Clair, et al., 2004
Ledauphin, J.; Saint-Clair, J.-F.; Lablanquie, O.; Guichard, H.; Founier, N.; Guichard, E.; Barillier, D., Identification of trace volatile compounds in freshly distilled calvados and cognac using preparative separations coupled with gas chromatography-mass spectrometry, J. Agric. Food Chem., 2004, 52, 16, 5124-5134, https://doi.org/10.1021/jf040052y . [all data]

Lipp, Krasnykh, et al., 2008
Lipp, S.V.; Krasnykh, E.L.; Levanova, S.V., Retention indices of symmetrical dicarboxylic acid esters, Rus. J. Anal. Chem., 2008, 63, 4, 349-352, https://doi.org/10.1134/S1061934808040072 . [all data]

Tsuge, Ohtan, et al., 2011
Tsuge, S.; Ohtan, H.; Watanabe, C., Pyrolysis - GC/MS Data Book of Synthetic Polymers, Elsevier, 2011, 420. [all data]

Peters, de Leer, et al., 1994
Peters, R.J.D.; de Leer, E.W.B.; Versteegh, J.F.M., Identification of Halogenated Compounds Produced by Chlorination of Humic Acid in the Presence of Bromide, J. Chromatogr. A, 1994, 686, 2, 253-261, https://doi.org/10.1016/0021-9673(94)00719-5 . [all data]

Okumura, 1991
Okumura, T., retention indices of environmental chemicals on methyl silicone capillary column, Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333 . [all data]

Pinkston, Spiteller, et al., 1981
Pinkston, D.; Spiteller, G.; von Henning, H.; Matthaei, D., High-resolution gas chromatography-mass spectrometry of the methyl esters of organic acids from uremic hemofiltrates, J. Chromatogr., 1981, 223, 1, 1-19, https://doi.org/10.1016/S0378-4347(00)80063-8 . [all data]

Spiteller and Spiteller, 1979
Spiteller, M.; Spiteller, G., Trennung und charakterisierung saurer harnbest and- teile, J. Chromatogr., 1979, 164, 3, 253-317, https://doi.org/10.1016/S0378-4347(00)81232-3 . [all data]

Staples and Zeiger, 2008
Staples, E.; Zeiger, K., On-Site Measurements of VOCs and Odors from Metal Casting Operations Using an Ultra-Fast Gas Chromatograph, 2008, retrieved from http://www.estcal.com/TechPapers/Industrial/FoundryOdors.doc. [all data]

Watanabe, Ueda, et al., 2008
Watanabe, A.; Ueda, Y.; Higuchi, M.; Shiba, N., Analysis of volatile compounds in beef fat by dinamic-headspace solid phase microextraction combined with gas chromatography - mass spectrometry, J. Food Sci., 2008, 73, 5, 420-425, https://doi.org/10.1111/j.1750-3841.2008.00764.x . [all data]

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

Rowland, Blackman, et al., 1995
Rowland, C.Y.; Blackman, A.J.; D'Arcy, B.R.; Rintoul, G.B., Comparison of organic extractives found in leatherwood (Eucryphia lucida) honey and leatherwood flowers and leaves, J. Agric. Food Chem., 1995, 43, 3, 753-763, https://doi.org/10.1021/jf00051a036 . [all data]

Guo, Wu, et al., 2008
Guo, L.; Wu, J.-Z.; Han, T.; Cao, T.; Rahman, K.; Qin, L.-P., Chemical composition, antifungal and antitumor properties of ether extracts of Scapania verrucosa Heeg. and its endophytic fungus Chaetomium fusiforme, Molecules, 2008, 13, 9, 2114-2125, https://doi.org/10.3390/molecules13092114 . [all data]

Suhardi, Suzuki, et al., 2002
Suhardi, S.; Suzuki, M.; Yoshida, K.; Muto, T.; Fujita, A.; Watanbe, N., Changes in the volatile compounds and in the chemical and physical properties of snake fruit (Salacca edulis Reinw) Cv. Pondoh during maturation, J. Agric. Food Chem., 2002, 50, 26, 7627-7633, https://doi.org/10.1021/jf020620e . [all data]


Notes

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