Methyl methacrylate

• Formula: C₅H₈O₂
• Molecular weight: 100.1158
• IUPAC Standard InChI: InChI=1S/C5H8O2/c1-4(2)5(6)7-3/h1H2,2-3H3 Copy

  
• IUPAC Standard InChIKey: VVQNEPGJFQJSBK-UHFFFAOYSA-N Copy
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • 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)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
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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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

Constant pressure heat capacity of liquid

Constant pressure heat capacity of solid

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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

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

2 =

By formula: 2C₅H₈O₂ = C₁₀H₁₆O₄

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

Ionization energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• GAS (30 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm^-1 resolution

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

• gas

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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Additional Data

UV/Visible 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

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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Kovats' RI, non-polar column, temperature ramp

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Kovats' RI, polar column, isothermal

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

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Normal alkane RI, non-polar column, temperature ramp

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

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Normal alkane RI, polar column, custom temperature program

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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), UV/Visible spectrum, 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.

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]

Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Knipmeyer, S.E.; Nguyen, A., Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for trans -Methyl Cinnamate, α-Methyl Cinnamaldehyde, Methyl Methacrylate, 1-Nonyne, Trimethylacetic Acid, Trimethylacetic Anhydride, and Ethyl Trimethyl Acetate, J. Chem. Eng. Data, 2002, 47, 4, 700-714, https://doi.org/10.1021/je010086r . [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]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Hull and Lu, 1984
Hull, Diane M.; Lu, Benjamin C.Y., Vapor-liquid equilibria in mixtures of cyclohexane and methyl methacrylate, J. Chem. Eng. Data, 1984, 29, 4, 417-419, https://doi.org/10.1021/je00038a014 . [all data]

Brockhaus and Jenckel, 1956
Brockhaus, Von A.; Jenckel, E., Über die kinetik des thermischen abbaues von polymethacrylsäuremethylester., Makromol. Chem., 1956, 18, 1, 262-293, https://doi.org/10.1002/macp.1956.020180124 . [all data]

Bywater, 1952
Bywater, S., Vapor pressures of methyl methacrylate and styrene, J. Polym. Sci., 1952, 9, 5, 417-422, https://doi.org/10.1002/pol.1952.120090503 . [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [all data]

Karabaev, Abduzhaminov, et al., 1985, 2
Karabaev, M.K.; Abduzhaminov, T.P.; Kenisarin, M.M.; Saidov, A.A., Thermodynamics of the crystal-liquid phase transition in acrylates and methacrylates, Izv. Akad. Nauk Uzb. SSR, Ser. Fiz.-Mat. Nauk, 1985, (5), 74-77. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]

Brunn, et al., 1976
Brunn, J., et al., J. prakt. Chem., 1976, 318, 745. [all data]

Ádámová, Orinák, et al., 2005
Ádámová, M.; Orinák, A.; Halás, L., Retention indices as identification tool in pyrolysis-capillary gas chromatography, J. Chromatogr. A, 2005, 1087, 1-2, 131-141, https://doi.org/10.1016/j.chroma.2005.01.003 . [all data]

Horna, Táborský, et al., 1985
Horna, A.; Táborský, J.; Dufka, O.; Matousek, P.; Churácek, J., Chromatography of monomers. II. Glass capillary gas chromatography of C₁-C₁₈ alkyl esters of acrylic and methacrylic acids, J. Chromatogr., 1985, 325, 367-378, https://doi.org/10.1016/S0021-9673(00)96047-3 . [all data]

Winskowski, 1983
Winskowski, J., Gaschromatographische Identifizierung von Stoffen anhand von Indexziffem und unterschiedlichen Detektoren, Chromatographia, 1983, 17, 3, 160-165, https://doi.org/10.1007/BF02271041 . [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]

Ashes and Haken, 1975
Ashes, J.R.; Haken, J.K., Gas chromatography of homologous esters. IX. Structure-retention increments of unsaturated esters, J. Chromatogr., 1975, 111, 1, 171-187, https://doi.org/10.1016/S0021-9673(01)80159-X . [all data]

Ashes and Haken, 1971
Ashes, J.R.; Haken, J.K., Gas chromatography of homologous esters. Part V. Retention of aliphatic esters on non-polar, donar and acceptor stationary phases, J. Chromatogr., 1971, 60, 33-44, https://doi.org/10.1016/S0021-9673(00)95527-4 . [all data]

Allen and Haken, 1970
Allen, I.D.; Haken, J.K., Gas chromatography of homologous esters. Part IV. Influence of stationary phase polarity on retention of unsaturated esters, J. Chromatogr., 1970, 51, 415-422, https://doi.org/10.1016/S0021-9673(01)96890-6 . [all data]

Germaine and Haken, 1969
Germaine, R.W.; Haken, J.K., Gas chromatography of homologous esters. Part 2. Unsaturated esters, J. Chromatogr., 1969, 43, 43-47, https://doi.org/10.1016/S0021-9673(00)99163-5 . [all data]

Stoev and Mladenov, 1979
Stoev, G.; Mladenov, I., A new approach in the choice of an internal standard for quantitative analysis in pyrolysis gas chromatography, C.R. Acad. Bulg. Sci., 1979, 32, 10, 1385-1388. [all data]

Pino, Mesa, et al., 2005
Pino, J.A.; Mesa, J.; Muñoz, Y.; Martí, M.P.; Marbot, R., Volatile components from mango (Mangifera indica L.) cultivars, J. Agric. Food Chem., 2005, 53, 6, 2213-2223, https://doi.org/10.1021/jf0402633 . [all data]

Xu, van Stee, et al., 2003
Xu, X.; van Stee, L.L.P.; Williams, J.; Beens, J.; Adahchour, M.; Vreuls, R.J.J.; Brinkman, U.A.Th.; Lelieveld, J., Comprehensive two-dimensional gas chromatography (GC×GC) measurements of volatile organic compounds in the atmosphere, Atmos. Chem. Phys., 2003, 3, 3, 665-682, https://doi.org/10.5194/acp-3-665-2003 . [all data]

Fischer and Kusch, 1990
Fischer, W.G.; Kusch, P., Automatic sampler for Curie-point pyrolysis-gas chromatography with on-column introduction of pyrolysates, J. Chromatogr., 1990, 518, 9-19, https://doi.org/10.1016/S0021-9673(01)93158-9 . [all data]

Haken and McKay, 1966
Haken, J.K.; McKay, T.R., The gas chromatographic analysis of N,N¹-Dialkyl anilines and vinyl monomers in polyester resins, J. Gas Chromatogr., 1966, 4, 4, 132-133, https://doi.org/10.1093/chromsci/4.4.132 . [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]

Health Safety Executive, 2000
Health Safety Executive, MDHS 96 Volatile organic compounds in air - Laboratory method using pumed solid sorbent tubes, solvent desorption and gas chromatography in Methods for the Determination of Hazardous Substances (MDHS) guidance, Crown, Colegate, Norwich, 2000, 1-24, retrieved from http://www.hse.gov.uk/pubns/mdhs/pdfs/mdhs96.pdf. [all data]

Jung, Wichmann, et al., 1999
Jung, A.; Wichmann, K.-H.; Kolb, M., VOC emission of polymeric packaging materials, LaborPraxis, 1999, 23, 9, 20-22. [all data]

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

Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technical_series₁997-01-01₁.pdf. [all data]

Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J., Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning, Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111 . [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]

Ramsey and Flanagan, 1982
Ramsey, J.D.; Flanagan, R.J., Detection and Identification of Volatile Organic Compounds in Blood by Headspace Gas Chromatography as an Aid to the Diagnosis of Solvent Abuse, J. Chromatogr., 1982, 240, 2, 423-444, https://doi.org/10.1016/S0021-9673(00)99622-5 . [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), UV/Visible spectrum, Gas Chromatography, NIST Free Links, 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
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  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
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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