Methyl vinyl 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 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
Δfgas-27.4 ± 2.6kcal/molEqkGuthrie, 1978ALS
Quantity Value Units Method Reference Comment
gas76.563cal/mol*KN/AKharitonov Yu.Ya., 1987This value was calculated by statistical mechanical method. Statistically calculated thermodynamic functions of [ Anjaneyulu Y., 1988] (S(300 K)=301.65 and Cp(300 K)=79.23 J/mol*K) seem to be erroneous. Values of S(298.15 K)=316.5 and Cp(298.15 K)=92.2 J/mol*K were calculated from data for related aldehydes and ketones by difference method [ Dorofeeva O.V., 1997].; GT

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

Quantity Value Units Method Reference Comment
Tboil354.6KN/AWeast and Grasselli, 1989BS
Tboil354.KN/AMurata, Arai, et al., 1957Uncertainty assigned by TRC = 4. K; TRC

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
309.80.191Aldrich Chemical Company Inc., 1990BS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
7.86294.AStephenson and Malanowski, 1987Based on data from 279. to 355. K.; AC
8.03315.AStephenson and Malanowski, 1987Based on data from 300. to 355. 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 as indicated in comments:
B - John E. Bartmess
ALS - 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

C4H5O- + Hydrogen cation = Methyl vinyl ketone

By formula: C4H5O- + H+ = C4H6O

Quantity Value Units Method Reference Comment
Δr363.3 ± 2.1kcal/molG+TSBartmess and Kiplinger, 1986gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr356.5 ± 2.0kcal/molIMREBartmess and Kiplinger, 1986gas phase; value altered from reference due to change in acidity scale; B

(CAS Reg. No. 71695-01-7 • 4294967295Methyl vinyl ketone) + Methyl vinyl ketone = CAS Reg. No. 71695-01-7

By formula: (CAS Reg. No. 71695-01-7 • 4294967295C4H6O) + C4H6O = CAS Reg. No. 71695-01-7

Quantity Value Units Method Reference Comment
Δr23.5 ± 4.6kcal/molN/AGraul and Squires, 1990gas phase; B

Hydrogen + Methyl vinyl ketone = 2-Butanone

By formula: H2 + C4H6O = C4H8O

Quantity Value Units Method Reference Comment
Δr-131.6kcal/molChydVeselova and Sul'man, 1980liquid phase; ALS

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
PackedApiezon L120.551.Bogoslovsky, Anvaer, et al., 1978Celite 545
PackedApiezon L160.557.Bogoslovsky, Anvaer, et al., 1978Celite 545

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

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Column type Active phase I Reference Comment
CapillarySPB-1557.Larráyoz, Addis, et al., 200130. m/0.32 mm/4. μm, He, 45. C @ 13. min, 5. K/min, 240. C @ 5. min
CapillaryDB-1568.2Helmig, Klinger, et al., 199960. m/0.32 mm/1. μm, -50. C @ 2. min, 6. K/min; Tend: 175. C
CapillaryDB-1568.Kaiser and Siegl, 199460. m/0.32 mm/1. μm, -50. C @ 4. min, 6. K/min; Tend: 180. C

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

View large format table.

Column type Active phase I Reference Comment
CapillarySupelcowax-10945.Elmore, Nisyrios, et al., 200560. m/0.25 mm/0.25 μm, He, 40. C @ 2. min, 4. K/min; Tend: 280. C
CapillaryDB-Wax948.Shimoda, Peralta, et al., 199660. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 50. C; Tend: 230. C

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

View large format table.

Column type Active phase I Reference Comment
CapillarySupelcowax-10947.Bianchi, Cantoni, et al., 200730. m/0.25 mm/0.25 μm; Program: 35C(8min) => 4C/min => 60C => 6C/min => 160C => 20C/min => 220C(1min)
CapillarySupelcowax-10953.Bianchi, Careri, et al., 200730. m/0.25 mm/0.25 μm, He; Program: 35C(8min) => 4C/min => 60C => 6C/min => 160C => 20C/min => 200C(1min)
CapillarySupelcowax-10946.Bianchi, Careri, et al., 200730. m/0.25 mm/0.25 μm, He; Program: 35C(8min) => 4C/min => 60C => 6C/min => 160C => 20C/min => 200C(1min)
CapillarySupelcowax-10947.Bianchi, Careri, et al., 200730. m/0.25 mm/0.25 μm, 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
CapillaryHP-5581.Isidorov, Purzynska, et al., 200630. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 3. K/min; Tend: 200. C

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

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Column type Active phase I Reference Comment
CapillaryDB-5 MS600.Cajka, Hajslova, et al., 200730. m/0.25 mm/0.25 μm, Helium; Program: 45 0C (0.75 min) 10 0C/min -> 200 0C 30 0C/min -> 245 0C (1.25 min)
CapillarySE-30550.Vinogradov, 2004Program: not specified
CapillaryMethyl Silicone576.Zenkevich, 1999Program: not specified
CapillaryPolydimethyl siloxanes576.Zenkevich, 1997Program: not specified
CapillaryMethyl Silicone576.Zenkevich, 1996Program: not specified
CapillaryMethyl Silicone590.Misharina, 1995Program: not specified
CapillaryDB-1561.Ciccioli, Cecinato, et al., 199460. m/0.32 mm/0.25 μm; Program: not specified
CapillaryDB-1561.Ciccioli, Brancaleoni, et al., 199360. m/0.32 mm/0.25 μm; Program: 3 min at 5 C; 5 - 50 C at 3 deg/min; 50 - 220 C at 5 deg/min

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryStabilwax961.Watcharananun, Cadwallader, et al., 200930. m/0.25 mm/0.50 μm, Helium, 35. C @ 5. min, 6. K/min, 225. C @ 10. min
CapillaryDB-Wax927.Osorio, Duque, et al., 200230. m/0.25 mm/0.25 μm, He, 50. C @ 4. min, 4. K/min, 220. C @ 20. min
CapillaryDB-Wax932.Osorio, Duque, et al., 200230. m/0.25 mm/0.25 μm, He, 50. C @ 4. min, 4. K/min, 220. C @ 20. min
CapillaryDB-Wax943.Umano, Hagi, et al., 200060. m/0.25 mm/0.25 μm, He, 40. C @ 2. min, 2. K/min; Tend: 200. C
CapillaryDB-Wax938.Horiuchi, Umano, et al., 199860. m/0.25 mm/1. μm, He, 3. K/min, 200. C @ 40. min; Tstart: 50. C
CapillaryDB-Wax945.Umano, Hagi, et al., 1995He, 40. C @ 2. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 200. C
CapillaryCarbowax 20M932.Kawakami and Kobayashi, 1991He, 60. C @ 4. min, 2. K/min; Column length: 50. m; Column diameter: 0.25 mm; Tend: 180. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillarySupelcowax-10946.Berard, Bianchi, et al., 200730. m/0.25 mm/0.25 μm, He; Program: 35C(8min) => 6C/min => 60C => 4C/min => 160C => 20C/min => 200C(1min)
CapillarySupelcowax-10953.Berard, Bianchi, et al., 200730. m/0.25 mm/0.25 μm, He; Program: 35C(8min) => 6C/min => 60C => 4C/min => 160C => 20C/min => 200C(1min)
CapillaryDB-Wax947.Kim. J.H., Ahn, et al., 200460. m/0.25 mm/0.25 μm, Helium; Program: 60 0C (3 min) 2 0C/min -> 150 0C 4 0C/min -> 200 0C
CapillaryCarbowax 20M995.Vinogradov, 2004Program: not specified
CapillarySupelcowax 10942.Castioni and Kapetanidis, 199660. m/0.25 mm/0.25 μm, Helium; Program: 60 0C (10 min) 2 0C/min -> 80 0C 3 0C/min -> 100 0C 4 0C/min -> 220 0C (30 min)
CapillaryCP-Wax 52CB931.Luning, de Rijk, et al., 199450. m/0.32 mm/1.5 μm; Program: 40C => 2C/min => 150C => 10C/min => 250C
CapillaryCarbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc.952.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, Notes

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

Guthrie, 1978
Guthrie, J.P., Equilibrium constants for a series of simple aldol condensations, and linear free energy relations with other carbonyl addition reactions, Can. J. Chem., 1978, 56, 962-973. [all data]

Kharitonov Yu.Ya., 1987
Kharitonov Yu.Ya., Thermodynamic properties of methylvinylketone calculated by statistical mechanics. Deposited at ONIITEkhim, Cherkassy, Ukraine, 16.04.87, No. 417-xn 87 (From Ref. Zh. Khim. 1987, 15 B3025DP), 1987. [all data]

Anjaneyulu Y., 1988
Anjaneyulu Y., Thermodynamic functions of some acryl derivatives, J. Indian Chem. Soc., 1988, 65, 400-403. [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]

Murata, Arai, et al., 1957
Murata, N.; Arai, H.; Tanaka, M., Synthesis of Methyl Vinyl Ketone, Kogyo Kagaku Zasshi, 1957, 60, 1206-7. [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]

Bartmess and Kiplinger, 1986
Bartmess, J.E.; Kiplinger, J.P., 'Kinetic' vs. thermodynamic acidities of enones in the gas phase, J. Org. Chem., 1986, 51, 2173. [all data]

Graul and Squires, 1990
Graul, S.T.; Squires, R.R., Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions, J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007 . [all data]

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

Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

Larráyoz, Addis, et al., 2001
Larráyoz, P.; Addis, M.; Gauch, R.; Bosset, J.O., Comparison of dynamic headspace and simultaneous distillation extraction techniques used for the analysis of the volatile components in three European PDO ewes milk cheeses, Int. Dairy J., 2001, 11, 11-12, 911-926, https://doi.org/10.1016/S0958-6946(01)00144-3 . [all data]

Helmig, Klinger, et al., 1999
Helmig, D.; Klinger, L.F.; Guenther, A.; Vierling, L.; Geron, C.; Zimmerman, P., Biogenic volatile organic compound emissions (BVOCs). I. Identifications from three continental sites in the U.S., Chemosphere, 1999, 38, 9, 2163-2187, https://doi.org/10.1016/S0045-6535(98)00425-1 . [all data]

Kaiser and Siegl, 1994
Kaiser, E.W.; Siegl, W.O., High resolution gas chromatographic determination of the atmospheric reactivity of engine-out hydrocarbon emissions from a spark-ignited engine, J. Hi. Res. Chromatogr., 1994, 17, 4, 264-270, https://doi.org/10.1002/jhrc.1240170414 . [all data]

Elmore, Nisyrios, et al., 2005
Elmore, J.S.; Nisyrios, I.; Mottram, D.S., Analysis of the headspace aroma compounds of walnuts (Juglans regia L.), Flavour Fragr. J., 2005, 20, 5, 501-506, https://doi.org/10.1002/ffj.1477 . [all data]

Shimoda, Peralta, et al., 1996
Shimoda, M.; Peralta, R.R.; Osajima, Y., Headspace gas analysis of fish sauce, J. Agric. Food Chem., 1996, 44, 11, 3601-3605, https://doi.org/10.1021/jf960345u . [all data]

Bianchi, Cantoni, et al., 2007
Bianchi, F.; Cantoni, C.; Careri, M.; Chiesa, L.; Musci, M.; Pinna, A., Characterization of the aromatic profile for the authentication and differentiation of typical Italian dry-sausages, Talanta, 2007, 72, 4, 1552-1563, https://doi.org/10.1016/j.talanta.2007.02.019 . [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]

Isidorov, Purzynska, et al., 2006
Isidorov, V.; Purzynska, A.; Modzelewska, A.; Serowiecka, M., Distribution coefficients of aliphatic alcohols, carbonyl compounds and esters between air and Carboxen/polydimethylsiloxane fiber coating, Anal. Chim. Acta., 2006, 560, 1-2, 103-109, https://doi.org/10.1016/j.aca.2005.12.043 . [all data]

Cajka, Hajslova, et al., 2007
Cajka, T.; Hajslova, J.; Cochran, J.; Holadova, K.; Klimankova, E., Solid phase microextraction - comprehensive two dimensional gas chromatography - time-of-flight mass spectrometry for the analysis of honey volatiles, J. Sep. Sci., 2007, 30, 4, 534-546, https://doi.org/10.1002/jssc.200600413 . [all data]

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

Zenkevich, 1999
Zenkevich, I.G., New Application of the Retention Index Concept in Gas and High Performance Liquid Chromatography, Fresenius' J. Anal. Chem., 1999, 365, 4, 305-309, https://doi.org/10.1007/s002160051491 . [all data]

Zenkevich, 1997
Zenkevich, I.G., Influence of the Variations of Dynamics Molecular Parameterts on the Additivity of Chromatigraphic Retention Indices of Products of Organic Reactions Relative to Initial Reagents, Dokl. Akad. Nauk (Rus.), 1997, 353, 5, 625-627. [all data]

Zenkevich, 1996
Zenkevich, I.G., Informational Maitenance of Gas Chromatographic Identification of Organic Compounds in Ecoanalytical Investigations, Z. Anal. Chem., 1996, 51, 11, 1140-1148. [all data]

Misharina, 1995
Misharina, T.A., Sorption regularities of sulfur- and oxygen-containing compounds in chromatography and their application in identification of volatile organic compounds, Diss. degree of Dr. Sci. (Chemistry), 1995, 52. [all data]

Ciccioli, Cecinato, et al., 1994
Ciccioli, P.; Cecinato, A.; Brancaleoni, E.; Brachetti, A.; Frattoni, M.; Sparapani, R., Composition and Distribution of Polar and Non-Polar VOCs in Urban, Rural, Forest and Remote Areas, Eur Commission EUR, 1994, 549-568. [all data]

Ciccioli, Brancaleoni, et al., 1993
Ciccioli, P.; Brancaleoni, E.; Cecinato, A.; Sparapani, R.; Frattoni, M., Identification and determination of biogenic and anthropogenic volatile organic compounds in forest areas of Northern and Southern Europe and a remote site of the Himalaya region by high-resolution gas chromatography-mass spectrometry, J. Chromatogr., 1993, 643, 1-2, 55-69, https://doi.org/10.1016/0021-9673(93)80541-F . [all data]

Watcharananun, Cadwallader, et al., 2009
Watcharananun, W.; Cadwallader, K.R.; Huangrak, K.; Kim, H.; Lorjaroenphon, Y., Identification of predominant odorants in Thai desserts flavored by smoking with Tian Op, a traditional Thai scented candle, J. Agric. Food Chem., 2009, 57, 3, 996-1005, https://doi.org/10.1021/jf802674c . [all data]

Osorio, Duque, et al., 2002
Osorio, C.; Duque, C.; Suarez, M.; Salamanca, L.E.; Uruena, F., Free, glycosidically bound, and phosphate bound flavor constituents of badea (Passiflora quadrangularis) fruit pulp, J. Sep. Sci., 2002, 25, 3, 147-154, https://doi.org/10.1002/1615-9314(20020201)25:3<147::AID-JSSC147>3.0.CO;2-G . [all data]

Umano, Hagi, et al., 2000
Umano, K.; Hagi, Y.; Nakahara, K.; Shoji, A.; Shibamoto, T., Volatile chemicals identified in extracts from leaves of Japanese mugwort (Artemisia princeps Pamp.), J. Agric. Food Chem., 2000, 48, 8, 3463-3469, https://doi.org/10.1021/jf0001738 . [all data]

Horiuchi, Umano, et al., 1998
Horiuchi, M.; Umano, K.; Shibamoto, T., Analysis of volatile compounds formed from fish oil heated with cysteine and trimethylamine oxide, J. Agric. Food Chem., 1998, 46, 12, 5232-5237, https://doi.org/10.1021/jf980482m . [all data]

Umano, Hagi, et al., 1995
Umano, K.; Hagi, Y.; Nakahara, K.; Shyoji, A.; Shibamoto, T., Volatile chemicals formed in the headspace of a heated D-glucose/L-cysteine Maillard model system, J. Agric. Food Chem., 1995, 43, 8, 2212-2218, https://doi.org/10.1021/jf00056a046 . [all data]

Kawakami and Kobayashi, 1991
Kawakami, M.; Kobayashi, A., Volatitle constituents of greem mate and roasted mate, J. Agric. Food Chem., 1991, 39, 7, 1275-1279, https://doi.org/10.1021/jf00007a016 . [all data]

Berard, Bianchi, et al., 2007
Berard, J.; Bianchi, F.; Careri, M.; Chatel, A.; Mangia, A.; Musci, M., Characterization of the volatile fraction and of free fatty acids of Fontina Valle d'Aosta, a protected designation of origin Italian cheese, Food Chem., 2007, 105, 1, 293-300, https://doi.org/10.1016/j.foodchem.2006.11.041 . [all data]

Kim. J.H., Ahn, et al., 2004
Kim. J.H.; Ahn, H.J.; Yook, H.S.; Kim, K.S.; Rhee, M.S.; Ryu, G.H.; Byun, M.W., Color, flavor, and sensory characteristics of gamma-irradiated salted and fermented anchovy sauce, Radiation Phys. Chem., 2004, 69, 2, 179-187, https://doi.org/10.1016/S0969-806X(03)00400-6 . [all data]

Castioni and Kapetanidis, 1996
Castioni, P.; Kapetanidis, I., Volatile constituents from Brunfelsia grandiflora ssp. grandiflora: qualitative analysis by GC-MS, Scientia Pharmaceutica, 1996, 64, 83-91. [all data]

Luning, de Rijk, et al., 1994
Luning, P.A.; de Rijk, T.; Wichers, H.J.; Roozen, J.P., Gas chromatography, mass spectrometry, and sniffing port analyses of volatile compounds of fresh bell peppers (Capsicum annuum) at different ripening stages, J. Agric. Food Chem., 1994, 42, 4, 977-983, https://doi.org/10.1021/jf00040a027 . [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References