Methyl vinyl ketone
- Formula: C4H6O
- Molecular weight: 70.0898
- IUPAC Standard InChIKey: FUSUHKVFWTUUBE-UHFFFAOYSA-N
- CAS Registry Number: 78-94-4
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: 3-Buten-2-one; Vinyl methyl ketone; 1-Buten-3-one; 2-Butenone; 3-Butene-2-one; CH2=CHCOCH3; Acetone, methylene-; Butenone; Ketone, methyl vinyl; Methyl ethenyl ketone; Methyl-vinyl-cetone; Methylvinylketon; Acetyl ethylene; Methylene acetone; γ-Oxo-α-butylene; UN 1251; 3-Oxobutene; 3-Butenen-2-one; But-3-en-2-one; 3-Oxo-1-butene; NSC 4853
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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 |
---|---|---|---|---|---|
ΔfH°gas | -27.4 ± 2.6 | kcal/mol | Eqk | Guthrie, 1978 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 76.563 | cal/mol*K | N/A | Kharitonov Yu.Ya., 1987 | This 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 |
---|---|---|---|---|---|
Tboil | 354.6 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 354. | K | N/A | Murata, Arai, et al., 1957 | Uncertainty assigned by TRC = 4. K; TRC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
309.8 | 0.191 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.86 | 294. | A | Stephenson and Malanowski, 1987 | Based on data from 279. to 355. K.; AC |
8.03 | 315. | A | Stephenson and Malanowski, 1987 | Based on data from 300. to 355. K.; AC |
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- + =
By formula: C4H5O- + H+ = C4H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 363.3 ± 2.1 | kcal/mol | G+TS | Bartmess and Kiplinger, 1986 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 356.5 ± 2.0 | kcal/mol | IMRE | Bartmess and Kiplinger, 1986 | gas phase; value altered from reference due to change in acidity scale; B |
(CAS Reg. No. 71695-01-7 • 4294967295) + = 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 |
---|---|---|---|---|---|
ΔrH° | 23.5 ± 4.6 | kcal/mol | N/A | Graul and Squires, 1990 | gas phase; B |
By formula: H2 + C4H6O = C4H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -131.6 | kcal/mol | Chyd | Veselova and Sul'man, 1980 | liquid 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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apiezon L | 120. | 551. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | Apiezon L | 160. | 557. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SPB-1 | 557. | Larráyoz, Addis, et al., 2001 | 30. m/0.32 mm/4. μm, He, 45. C @ 13. min, 5. K/min, 240. C @ 5. min |
Capillary | DB-1 | 568.2 | Helmig, Klinger, et al., 1999 | 60. m/0.32 mm/1. μm, -50. C @ 2. min, 6. K/min; Tend: 175. C |
Capillary | DB-1 | 568. | Kaiser and Siegl, 1994 | 60. 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-10 | 945. | Elmore, Nisyrios, et al., 2005 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 2. min, 4. K/min; Tend: 280. C |
Capillary | DB-Wax | 948. | Shimoda, Peralta, et al., 1996 | 60. 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-10 | 947. | Bianchi, Cantoni, et al., 2007 | 30. m/0.25 mm/0.25 μm; Program: 35C(8min) => 4C/min => 60C => 6C/min => 160C => 20C/min => 220C(1min) |
Capillary | Supelcowax-10 | 953. | Bianchi, Careri, et al., 2007 | 30. m/0.25 mm/0.25 μm, He; Program: 35C(8min) => 4C/min => 60C => 6C/min => 160C => 20C/min => 200C(1min) |
Capillary | Supelcowax-10 | 946. | Bianchi, Careri, et al., 2007 | 30. m/0.25 mm/0.25 μm, He; Program: 35C(8min) => 4C/min => 60C => 6C/min => 160C => 20C/min => 200C(1min) |
Capillary | Supelcowax-10 | 947. | Bianchi, Careri, et al., 2007 | 30. 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 581. | Isidorov, Purzynska, et al., 2006 | 30. 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 MS | 600. | Cajka, Hajslova, et al., 2007 | 30. 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) |
Capillary | SE-30 | 550. | Vinogradov, 2004 | Program: not specified |
Capillary | Methyl Silicone | 576. | Zenkevich, 1999 | Program: not specified |
Capillary | Polydimethyl siloxanes | 576. | Zenkevich, 1997 | Program: not specified |
Capillary | Methyl Silicone | 576. | Zenkevich, 1996 | Program: not specified |
Capillary | Methyl Silicone | 590. | Misharina, 1995 | Program: not specified |
Capillary | DB-1 | 561. | Ciccioli, Cecinato, et al., 1994 | 60. m/0.32 mm/0.25 μm; Program: not specified |
Capillary | DB-1 | 561. | Ciccioli, Brancaleoni, et al., 1993 | 60. 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Stabilwax | 961. | Watcharananun, Cadwallader, et al., 2009 | 30. m/0.25 mm/0.50 μm, Helium, 35. C @ 5. min, 6. K/min, 225. C @ 10. min |
Capillary | DB-Wax | 927. | Osorio, Duque, et al., 2002 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 4. min, 4. K/min, 220. C @ 20. min |
Capillary | DB-Wax | 932. | Osorio, Duque, et al., 2002 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 4. min, 4. K/min, 220. C @ 20. min |
Capillary | DB-Wax | 943. | Umano, Hagi, et al., 2000 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 2. min, 2. K/min; Tend: 200. C |
Capillary | DB-Wax | 938. | Horiuchi, Umano, et al., 1998 | 60. m/0.25 mm/1. μm, He, 3. K/min, 200. C @ 40. min; Tstart: 50. C |
Capillary | DB-Wax | 945. | Umano, Hagi, et al., 1995 | He, 40. C @ 2. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 200. C |
Capillary | Carbowax 20M | 932. | Kawakami and Kobayashi, 1991 | He, 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-10 | 946. | Berard, Bianchi, et al., 2007 | 30. m/0.25 mm/0.25 μm, He; Program: 35C(8min) => 6C/min => 60C => 4C/min => 160C => 20C/min => 200C(1min) |
Capillary | Supelcowax-10 | 953. | Berard, Bianchi, et al., 2007 | 30. m/0.25 mm/0.25 μm, He; Program: 35C(8min) => 6C/min => 60C => 4C/min => 160C => 20C/min => 200C(1min) |
Capillary | DB-Wax | 947. | Kim. J.H., Ahn, et al., 2004 | 60. m/0.25 mm/0.25 μm, Helium; Program: 60 0C (3 min) 2 0C/min -> 150 0C 4 0C/min -> 200 0C |
Capillary | Carbowax 20M | 995. | Vinogradov, 2004 | Program: not specified |
Capillary | Supelcowax 10 | 942. | Castioni and Kapetanidis, 1996 | 60. 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) |
Capillary | CP-Wax 52CB | 931. | Luning, de Rijk, et al., 1994 | 50. m/0.32 mm/1.5 μm; Program: 40C => 2C/min => 150C => 10C/min => 250C |
Capillary | Carbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc. | 952. | Waggott and Davies, 1984 | Hydrogen; 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,
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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
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Murata, Arai, et al., 1957
Murata, N.; Arai, H.; Tanaka, M.,
Synthesis of Methyl Vinyl Ketone,
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Aldrich Chemical Company Inc., 1990
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Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
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Bartmess and Kiplinger, 1986
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'Kinetic' vs. thermodynamic acidities of enones in the gas phase,
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Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions,
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Veselova and Sul'man, 1980
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Effect of the chemical structure of α,β-unsaturated esters and ketones on the selectivity of their hydrogenation,
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Bogoslovsky, Anvaer, et al., 1978
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Comparison of dynamic headspace and simultaneous distillation extraction techniques used for the analysis of the volatile components in three European PDO ewes milk cheeses,
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High resolution gas chromatographic determination of the atmospheric reactivity of engine-out hydrocarbon emissions from a spark-ignited engine,
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Solid phase microextraction - comprehensive two dimensional gas chromatography - time-of-flight mass spectrometry for the analysis of honey volatiles,
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New Application of the Retention Index Concept in Gas and High Performance Liquid Chromatography,
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Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References
- Symbols used in this document:
S°gas Entropy of gas at standard conditions Tboil Boiling point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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