Methylal
- Formula: C3H8O2
- Molecular weight: 76.0944
- IUPAC Standard InChIKey: NKDDWNXOKDWJAK-UHFFFAOYSA-N
- CAS Registry Number: 109-87-5
- 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: Methane, dimethoxy-; Dimethyl formal; Anesthenyl; Dimethoxymethane; Formal; Formaldehyde dimethyl acetal; Methoxymethyl methyl ether; Methylene dimethyl ether; Methylene glycol dimethylether; (CH3O)2CH2; Methylenedioxydimethane; Metylal; UN 1234; Formaldehyde methyl ketal; 2,4-Dioxapentane; Dimethylacetal formaldehyde; Bis(methoxy)methane
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Gas phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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:
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 | -83.21 ± 0.19 | kcal/mol | Cm | Pilcher and Fletcher, 1969 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°gas | -472.20 ± 0.18 | kcal/mol | Cm | Pilcher and Fletcher, 1969 | Corresponding ΔfHºgas = -83.21 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 80.24 ± 0.15 | cal/mol*K | N/A | McEachern D.M., 1964 | 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
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 |
---|---|---|---|---|---|
Tboil | 315.3 ± 0.5 | K | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 168. | K | N/A | Timmermans, 1935 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 168.35 | K | N/A | Timmermans, 1934 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 168.15 | K | N/A | Timmermans and Martin, 1928 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 168.35 | K | N/A | Timmermans, 1911 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 168.03 | K | N/A | Wilhoit, Chao, et al., 1985 | Uncertainty assigned by TRC = 0.05 K; TRC |
Ttriple | 168.01 | K | N/A | McEachern and Kilpatrick, 1964 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 480.6 | K | N/A | Kobe and Mathews, 1970 | Uncertainty assigned by TRC = 1. K; TRC |
Tc | 488.4 | K | N/A | Bourgou, 1924 | Uncertainty assigned by TRC = 6. K; TRC |
Tc | 496.8 | K | N/A | Pawlewski, 1883 | Uncertainty assigned by TRC = 10. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 38.98 | atm | N/A | Kobe and Mathews, 1970 | Uncertainty assigned by TRC = 0.6999 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 4.69 | mol/l | N/A | Kobe and Mathews, 1970 | Uncertainty assigned by TRC = 0.39 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 7.07 | kcal/mol | N/A | Albert, Hahnenstein, et al., 2001 | Based on data from 273. to 357. K.; AC |
ΔvapH° | 6.904 ± 0.050 | kcal/mol | V | McEachern and Kilpatrick, 1964, 2 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
6.9039 | 298.15 | N/A | McEachern and Kilpatrick, 1964, 3 | P = 53.14 kPa; DH |
7.46 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 316. K.; AC |
7.12 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 318. K.; AC |
7.24 | 305. | N/A | Brazhnikov, Peshchenko, et al., 1976 | Based on data from 296. to 314. K.; AC |
7.19 | 288. | N/A | Nicolini and Laffitte, 1949 | Based on data from 273. to 308. K.; AC |
Entropy of vaporization
ΔvapS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
23.2 | 298.15 | McEachern and Kilpatrick, 1964, 3 | P; DH |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
273. to 308. | 4.03104 | 1068.35 | -50.409 | Nicolini and Laffitte, 1949, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.9913 | 168.01 | McEachern and Kilpatrick, 1964, 3 | DH |
1.99 | 168. | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.85 | 168.01 | McEachern and Kilpatrick, 1964, 3 | 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 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
By formula: H4N+ + C3H8O2 = (H4N+ • C3H8O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 29.1 | kcal/mol | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1996 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 25.2 | cal/mol*K | PHPMS | Meot-Ner (Mautner), Sieck, et al., 1996 | gas phase; M |
By formula: C3H8O2 + H2O = CH2O + 2CH4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 18.45 ± 0.12 | kcal/mol | Cm | Birley and Skinner, 1970 | liquid phase; Heat of hydrolysis; ALS |
Gas phase ion energetics data
Go To: Top, Gas 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 |
---|---|---|---|
9.7 | PE | Zverev, Villem, et al., 1982 | LBLHLM |
10.00 ± 0.05 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
10.42 | PE | Zverev, Villem, et al., 1982 | Vertical value; LBLHLM |
10.20 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
10.29 | PE | Jorgensen, 1981 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H5O+ | 10.69 ± 0.05 | CH3O | EI | Holmes and Lossing, 1984 | LBLHLM |
C2H5O+ | 11.1 | CH3O | EI | Harrison, Ivko, et al., 1966 | RDSH |
C3H7O2+ | 10.38 ± 0.03 | H | EI | Martin, Lampe, et al., 1966 | RDSH |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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 |
Gas Chromatography
Go To: Top, Gas 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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Squalane | 115. | 500. | Lafosse and Thuaud-Chourrout, 1975 | Column length: 100. m; Column diameter: 0.25 mm |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | BP-1 | 511. | Health Safety Executive, 2000 | 50. 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SPB-1 | 508. | Flanagan, Streete, et al., 1997 | 60. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C |
Capillary | SPB-1 | 508. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C |
Capillary | SPB-1 | 505. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: not specified |
Capillary | OV-1 | 505. | Ramsey and Flanagan, 1982 | Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 740. | Ramsey and Flanagan, 1982 | Program: not specified |
References
Go To: Top, Gas 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]
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
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, 2
McEachern, D.M., Jr.; Kilpatrick, J.E.,
Entropy and related thermodynamic properties of dimethoxymethane,
Ber. Bunsenges. Phys. Chem., 1964, 41, 3127. [all data]
McEachern and Kilpatrick, 1964, 3
McEachern, D.M., Jr.; Kilpatrick, J.E.,
Entropy and related thermodynamic properties of dimethoxymethane,
J. Chem. Phys., 1964, 41, 3127-3131. [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, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Pc Critical pressure S°gas Entropy of gas at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°gas Enthalpy of combustion of gas at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ΔvapS Entropy of vaporization ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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