Methyl methacrylate
- Formula: C5H8O2
- Molecular weight: 100.1158
- IUPAC Standard InChI: InChI=1S/C5H8O2/c1-4(2)5(6)7-3/h1H2,2-3H3
- IUPAC Standard InChIKey: VVQNEPGJFQJSBK-UHFFFAOYSA-N
- CAS Registry Number: 80-62-6
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: 2-Propenoic acid, 2-methyl-, methyl ester; Methacrylic acid methyl ester; Diakon; Methyl 2-methyl-2-propenoate; Methyl 2-methylpropenoate; MMA; Pegalan; CH2=C(CH3)COOCH3; Methyl-α-methacrylate; Monocite methacrylate monomer; Metakrylan metylu; Methacrylate de methyle; Methacrylsaeuremethyl ester; Methyl α-methylacrylate; Methyl methylacrylate; Methyl-methacrylat; Methylmethacrylaat; Metil metacrilato; NCI-C50680; Paladon; 2-Methylacrylic acid, methyl ester; Acrylic acid, 2-methyl-, methyl ester; Methylester kyseliny methakrylove; Methyl methacrylate monomer; 2-Methyl-2-propenoic acid methyl ester; Rcra waste number U162; Methyl ester of 2-methyl-2-propenoic acid; 2-(Methoxycarbonyl)-1-propene; Acryester M; NSC 4769; TEB 3K; 2-Methylacrylic, methyl ester
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes
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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -348.7 | kJ/mol | N/A | Vilcu and Perisanu, 1980 | Value computed using ΔfHliquid° value of -388.8±4 kj/mol from Vilcu and Perisanu, 1980 and ΔvapH° value of 40.1 kj/mol from missing citation.; DRB |
| ΔfH°gas | -342.3 | kJ/mol | N/A | Vilcu and Perisanu, 1980 | Value computed using ΔfHliquid° value of -382.4 kj/mol from Vilcu and Perisanu, 1980 and ΔvapH° value of 40.1 kj/mol from missing citation.; DRB |
| ΔfH°gas | -331.0 | kJ/mol | Ccb | Vilcu, Perisanu, et al., 1975 | ALS |
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 |
|---|---|---|---|---|---|
| ΔfH°liquid | -382.4 | kJ/mol | Chyd | Vilcu and Perisanu, 1980 | ALS |
| ΔfH°liquid | -388.8 ± 4.0 | kJ/mol | Ccb | Vilcu and Perisanu, 1980 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -2724.6 ± 4.0 | kJ/mol | Ccb | Vilcu and Perisanu, 1980 | Corresponding ΔfHºliquid = -386.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 266.2 | J/mol*K | N/A | Lebedev and Rabinovich, 1971 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 191.09 | 298.15 | Zhang, Benson, et al., 1986 | DH |
| 215.3 | 298.15 | Karabaev, Abduzhaminov, et al., 1985 | T = 225 to 350 K. Equation only. Cp (J/kg*K) = 114.1 + 6.8299 T. Cp data calculated from equation.; DH |
| 215.3 | 298.15 | Karabaev, Saidov, et al., 1985 | T = 90 to 350 K. Cp(c) = 280.01 + 4.96T J/kg*K (103 to 212 K); Cp(liq) = 114.12 + 6.83T J/kg*K (225.6 to 350 K). Cp data calculated from equation.; DH |
| 192.4 | 300. | Lebedev and Rabinovich, 1971 | T = 60 to 300 K.; DH |
| 210.55 | 298.15 | Melia, 1962 | T = 60 to 300 K.; DH |
| 188.49 | 293. | Erds, Jger, et al., 1952 | T = 20 to 50°C.; DH |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 150.2 | 210. | Sochava and Trapeznikova, 1958 | T = 60 to 210 K.; DH |
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
+
=
By formula: H2 + C5H8O2 = C5H10O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -108. ± 5.0 | kJ/mol | Chyd | Vilcu and Perisanu, 1980 | liquid phase |
| ΔrH° | -119.8 ± 0.2 | kJ/mol | Chyd | Dolliver, Gresham, et al., 1938 | gas phase; At 355 K |
2 =
By formula: 2C5H8O2 = C10H16O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -26. | kJ/mol | Kin | Stickler and Meyerhoff, 1980 | liquid phase |
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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 831.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 800.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.7 | PE | Van Dam and Oskam, 1978 | LLK |
| 10.06 | PE | Van Dam and Oskam, 1978 | Vertical value; LLK |
| 10.28 | PE | Sustmann and Trill, 1972 | Vertical value; LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Vilcu and Perisanu, 1980
Vilcu, R.; Perisanu, S.,
The ideal gas state enthalpies of formation of some monomers,
Rev. Roum. Chim., 1980, 25, 619-624. [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]
Lebedev and Rabinovich, 1971
Lebedev, B.V.; Rabinovich, I.B.,
Heat capacities and thermodynamic functions of methyl methacrylate and poly(methyl methacrylate),
Tr. Khim. Khim. Tekhnol., 1971, 1, 8-11. [all data]
Zhang, Benson, et al., 1986
Zhang, D.; Benson, G.C.; Kumaran, M.K.; Lu, B.C.-Y.,
Excess thermodynamic properties for methyl methacrylate + methanol and + ethanol,
J. Chem. Thermodynam., 1986, 18, 149-158. [all data]
Karabaev, Abduzhaminov, et al., 1985
Karabaev, M.; Abduzhaminov, T.P.; Saidov, A.A.; Igamberdyev, Kh.T.,
Thermophysical properties of liquid methacrylic acid and its simple esters, Izv. Akad. Nauk Uzb. SSR,
Ser. Fiz.-Mat. Nauk, 1985, (4), 71-74. [all data]
Karabaev, Saidov, et al., 1985
Karabaev, M.; Saidov, A.A.; Abduzhaminov, T.P.; Kenisarin, M.M.,
Heat capacity and molecular kinetic processes of condensed phase acrylates and methacrylates, Izv. Akad. Nauk UzSSR,
Ser. Fiz.-Math., 1985, (6), 51-54. [all data]
Melia, 1962
Melia, T.P.,
Part VIII-Methylmethacrylate and polymethylmethacrylate,
Polymer, 1962, 3, 317-319. [all data]
Erds, Jger, et al., 1952
Erds, E.; Jger, L.; Pouchly, J.,
Specificka tepla methylesteru a butylesteru kyseliny methakrylove,
Chem. Listy, 1952, 46, 770. [all data]
Sochava and Trapeznikova, 1958
Sochava, I.V.; Trapeznikova, O.N.,
Internal rotation and specific heat of some polymers at low temperatures, Vestn. Leningrad. Univ. 13, No.16,
Ser. Fiz. Khim., 1958, No.3, 65-72. [all data]
Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E.,
Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds,
J. Am. Chem. Soc., 1938, 60, 440-450. [all data]
Stickler and Meyerhoff, 1980
Stickler, M.; Meyerhoff, G.,
Thermal polymerization of methyl methacrylate. 2. Formation of unsaturated dimers,
Makromol. Chem., 1980, 181, 131-147. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Van Dam and Oskam, 1978
Van Dam, H.; Oskam, A.,
He(I) and He(II) photoelectron spectra of some substituted ethylenes,
J. Electron Spectrosc. Relat. Phenom., 1978, 13, 273. [all data]
Sustmann and Trill, 1972
Sustmann, R.; Trill, H.,
Photoelektronenspektroskopische Bestimmung von Substituenten-Effekten. II. α,β-ungesattigte Carbonester,
Tetrahedron Lett., 1972, 42, 4271. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Cp,solid Constant pressure heat capacity of solid S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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