Methylal

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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-83.21 ± 0.19kcal/molCmPilcher and Fletcher, 1969ALS
Quantity Value Units Method Reference Comment
Δcgas-472.20 ± 0.18kcal/molCmPilcher and Fletcher, 1969Corresponding Δfgas = -83.21 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
gas80.24 ± 0.15cal/mol*KN/AMcEachern D.M., 1964GT

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: Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
liquid58.320cal/mol*KN/AMcEachern and Kilpatrick, 1964 

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
38.580298.15McEachern and Kilpatrick, 1964T = 15 to 300 K.
39.10298.von Reis, 1881T = 289 to 323 K.

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
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
Tboil315.3 ± 0.5KAVGN/AAverage of 10 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus168.KN/ATimmermans, 1935Uncertainty assigned by TRC = 2. K; TRC
Tfus168.35KN/ATimmermans, 1934Uncertainty assigned by TRC = 0.5 K; TRC
Tfus168.15KN/ATimmermans and Martin, 1928Uncertainty assigned by TRC = 0.4 K; TRC
Tfus168.35KN/ATimmermans, 1911Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Ttriple168.03KN/AWilhoit, Chao, et al., 1985Uncertainty assigned by TRC = 0.05 K; TRC
Ttriple168.01KN/AMcEachern and Kilpatrick, 1964, 2Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Tc480.6KN/AKobe and Mathews, 1970Uncertainty assigned by TRC = 1. K; TRC
Tc488.4KN/ABourgou, 1924Uncertainty assigned by TRC = 6. K; TRC
Tc496.8KN/APawlewski, 1883Uncertainty assigned by TRC = 10. K; TRC
Quantity Value Units Method Reference Comment
Pc38.98atmN/AKobe and Mathews, 1970Uncertainty assigned by TRC = 0.6999 atm; TRC
Quantity Value Units Method Reference Comment
ρc4.69mol/lN/AKobe and Mathews, 1970Uncertainty assigned by TRC = 0.39 mol/l; TRC
Quantity Value Units Method Reference Comment
Δvap7.07kcal/molN/AAlbert, Hahnenstein, et al., 2001Based on data from 273. to 357. K.; AC
Δvap6.904 ± 0.050kcal/molVMcEachern and Kilpatrick, 1964, 3ALS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
6.9039298.15N/AMcEachern and Kilpatrick, 1964P = 53.14 kPa; DH
7.46288.AStephenson and Malanowski, 1987Based on data from 273. to 316. K.; AC
7.12288.AStephenson and Malanowski, 1987Based on data from 273. to 318. K.; AC
7.24305.N/ABrazhnikov, Peshchenko, et al., 1976Based on data from 296. to 314. K.; AC
7.19288.N/ANicolini and Laffitte, 1949Based on data from 273. to 308. K.; AC

Entropy of vaporization

ΔvapS (cal/mol*K) Temperature (K) Reference Comment
23.2298.15McEachern and Kilpatrick, 1964P; DH

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
273. to 308.4.031041068.35-50.409Nicolini and Laffitte, 1949, 2Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
1.9913168.01McEachern and Kilpatrick, 1964DH
1.99168.Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
11.85168.01McEachern and Kilpatrick, 1964DH

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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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

NH4+ + Methylal = (NH4+ • Methylal)

By formula: H4N+ + C3H8O2 = (H4N+ • C3H8O2)

Quantity Value Units Method Reference Comment
Δr29.1kcal/molPHPMSMeot-Ner (Mautner), Sieck, et al., 1996gas phase; M
Quantity Value Units Method Reference Comment
Δr25.2cal/mol*KPHPMSMeot-Ner (Mautner), Sieck, et al., 1996gas phase; M

Methylal + Water = Formaldehyde + 2Methyl Alcohol

By formula: C3H8O2 + H2O = CH2O + 2CH4O

Quantity Value Units Method Reference Comment
Δr18.45 ± 0.12kcal/molCmBirley and Skinner, 1970liquid phase; Heat of hydrolysis; ALS

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

IE (eV) Method Reference Comment
9.7PEZverev, Villem, et al., 1982LBLHLM
10.00 ± 0.05PIWatanabe, Nakayama, et al., 1962RDSH
10.42PEZverev, Villem, et al., 1982Vertical value; LBLHLM
10.20PEKimura, Katsumata, et al., 1981Vertical value; LLK
10.29PEJorgensen, 1981Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H5O+10.69 ± 0.05CH3OEIHolmes and Lossing, 1984LBLHLM
C2H5O+11.1CH3OEIHarrison, Ivko, et al., 1966RDSH
C3H7O2+10.38 ± 0.03HEIMartin, Lampe, et al., 1966RDSH

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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


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

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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.
NIST MS number 372

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Gas Chromatography

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), References, Notes

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

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillarySqualane115.500.Lafosse and Thuaud-Chourrout, 1975Column length: 100. 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
CapillaryBP-1511.Health Safety Executive, 200050. m/0.22 mm/0.75 μm, He, 5. K/min; Tstart: 50. C; Tend: 200. C

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

View large format table.

Column type Active phase I Reference Comment
CapillarySPB-1508.Flanagan, Streete, et al., 199760. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C
CapillarySPB-1508.Strete, Ruprah, et al., 199260. m/0.53 mm/5.0 μm, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C
CapillarySPB-1505.Strete, Ruprah, et al., 199260. m/0.53 mm/5.0 μm, Helium; Program: not specified
CapillaryOV-1505.Ramsey and Flanagan, 1982Program: not specified

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryCarbowax 20M740.Ramsey and Flanagan, 1982Program: not specified

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), Gas Chromatography, Notes

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

Pilcher and Fletcher, 1969
Pilcher, G.; Fletcher, R.A., Measurements of heats of combustion by flame calorimetry. Part 5.-Dimethoxymethane, 1,1-Dimethoxyethane, Trans. Faraday Soc., 1969, 65, 2326-2330. [all data]

McEachern D.M., 1964
McEachern D.M., Jr., Entropy and related thermodynamic properties of dimethoxymethane, J. Chem. Phys., 1964, 41, 3127-3131. [all data]

McEachern and Kilpatrick, 1964
McEachern, D.M., Jr.; Kilpatrick, J.E., Entropy and related thermodynamic properties of dimethoxymethane, J. Chem. Phys., 1964, 41, 3127-3131. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Timmermans, 1935
Timmermans, J., Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds., Bull. Soc. Chim. Belg., 1935, 44, 17-40. [all data]

Timmermans, 1934
Timmermans, J., Theory of Concentrated Solutions XII., Bull. Soc. Chim. Belg., 1934, 43, 626. [all data]

Timmermans and Martin, 1928
Timmermans, J.; Martin, F., Study of the Physical Constants of Twenty Organic Compounds of the Physical Constants of Twenty Organic Compounds, J. Chim. Phys. Phys.-Chim. Biol., 1928, 25, 411. [all data]

Timmermans, 1911
Timmermans, J., Researches on the freezing point of organic liquid compounds, Bull. Soc. Chim. Belg., 1911, 25, 300. [all data]

Wilhoit, Chao, et al., 1985
Wilhoit, R.C.; Chao, J.; Hall, K.R., Thermodynamic Properties of Key Organic Compounds in the Carbon Range C1 to C4. Part 1. Properties of Condensed Phases, J. Phys. Chem. Ref. Data, 1985, 14, 1. [all data]

McEachern and Kilpatrick, 1964, 2
McEachern, D.M.; Kilpatrick, J.E., Entropy and related thermodynamic properties of dimethoxymethane., J. Chem. Phys., 1964, 41, 3127-31. [all data]

Kobe and Mathews, 1970
Kobe, K.A.; Mathews, J.F., Critical Properties and Vapor Pressures of Some Organic Nitrogen and Oxygen Compounds, J. Chem. Eng. Data, 1970, 15, 182. [all data]

Bourgou, 1924
Bourgou, A., Contribution a l'Etude du Methylal comme Solvant, Bull. Soc. Chim. Belg., 1924, 33, 101-115. [all data]

Pawlewski, 1883
Pawlewski, B., Critical temperatures of some liquids, Ber. Dtsch. Chem. Ges., 1883, 16, 2633-36. [all data]

Albert, Hahnenstein, et al., 2001
Albert, Michael; Hahnenstein, Immanuel; Hasse, Hans; Maurer, Gerd, Vapor-Liquid and Liquid-Liquid Equilibria in Binary and Ternary Mixtures of Water, Methanol, and Methylal, J. Chem. Eng. Data, 2001, 46, 4, 897-903, https://doi.org/10.1021/je000352l . [all data]

McEachern and Kilpatrick, 1964, 3
McEachern, D.M., Jr.; Kilpatrick, J.E., Entropy and related thermodynamic properties of dimethoxymethane, Ber. Bunsenges. Phys. Chem., 1964, 41, 3127. [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]

Brazhnikov, Peshchenko, et al., 1976
Brazhnikov, M.M.; Peshchenko, A.D.; Ral'ko, O.V., Zh. Prikl. Khim. (Leningrad), 1976, 49, 1041. [all data]

Nicolini and Laffitte, 1949
Nicolini, E.; Laffitte, P., Compt. Rend., 1949, 229, 757. [all data]

Nicolini and Laffitte, 1949, 2
Nicolini, E.; Laffitte, P., Tensions de Vapeur de Quelques Liquides Organiques Purs, Compt. Rend., 1949, 229, 757-759. [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]

Meot-Ner (Mautner), Sieck, et al., 1996
Meot-Ner (Mautner), M.; Sieck, L.W.; Liebman, J.F.; Scheiner, S., Complexing of the Ammonium Ion by Polyethers. Comparative Complexing Thermochemistry of Ammonium, Hydronium, and Alkali Cations, J. Phys. Chem., 1996, 100, 16, 6445, https://doi.org/10.1021/jp9514943 . [all data]

Birley and Skinner, 1970
Birley, G.I.; Skinner, H.A., Enthalpies of hydrolysis of dimethoxymethane and 1,1-dimethoxyethane, Trans. Faraday Soc., 1970, 66, 791-793. [all data]

Zverev, Villem, et al., 1982
Zverev, V.V.; Villem, Ya.Ya.; Villem, N.V.; Klimovitskii, E.N.; Arbuzov, B.A., Photoelectron spectra and intramolecular interactions of dimethoxymethane and 4,7-dihydro-1,3-dioxepin, J. Gen. Chem. USSR, 1982, 52, 1674, In original 1888. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Jorgensen, 1981
Jorgensen, F.S., Photoelectron spectrum and molecular orbital (MNDO and PRDDO) study of dimethoxymethane, J. Chem. Res. Synop., 1981, 212. [all data]

Holmes and Lossing, 1984
Holmes, J.L.; Lossing, F.P., Heats of formation of organic radicals from appearance energies, Int. J. Mass Spectrom. Ion Processes, 1984, 58, 113. [all data]

Harrison, Ivko, et al., 1966
Harrison, A.G.; Ivko, A.; Van Raalte, D., Energetics of formation of some oxygenated ions and the proton affinities of carbonyl compounds, Can. J. Chem., 1966, 44, 1625. [all data]

Martin, Lampe, et al., 1966
Martin, R.H.; Lampe, F.W.; Taft, R.W., An electron-impact study of ionization and dissociation in methoxy- and halogen- substituted methanes, J. Am. Chem. Soc., 1966, 88, 1353. [all data]

Lafosse and Thuaud-Chourrout, 1975
Lafosse, M.; Thuaud-Chourrout, N., Etude du comportement de composés halogénés et mèthoxylés en CG dans le cas de quatre phases stationnaires liquides pouvant former des liaisons de type donneur-accepteur d'électrons avec les groupes fonctionnels de ces composés, Chromatographia, 1975, 8, 4, 195-202, https://doi.org/10.1007/BF02274456 . [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]

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/technicalseries1997-01-011.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]

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), Gas Chromatography, References