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, Condensed phase thermochemistry data, Phase change 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 | -348.2 ± 0.79 | kJ/mol | Cm | Pilcher and Fletcher, 1969 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°gas | -1975.7 ± 0.75 | kJ/mol | Cm | Pilcher and Fletcher, 1969 | Corresponding ΔfHºgas = -348.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 335.72 ± 0.62 | J/mol*K | N/A | McEachern D.M., 1964 | GT |
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 |
---|---|---|---|---|---|
S°liquid | 244.01 | J/mol*K | N/A | McEachern and Kilpatrick, 1964 |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
161.42 | 298.15 | McEachern and Kilpatrick, 1964 | T = 15 to 300 K. |
163.6 | 298. | von Reis, 1881 | T = 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 |
---|---|---|---|---|---|
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, 2 | 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 | 39.50 | bar | N/A | Kobe and Mathews, 1970 | Uncertainty assigned by TRC = 0.7092 bar; 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° | 29.6 | kJ/mol | N/A | Albert, Hahnenstein, et al., 2001 | Based on data from 273. to 357. K.; AC |
ΔvapH° | 28.89 ± 0.21 | kJ/mol | V | McEachern and Kilpatrick, 1964, 3 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
28.886 | 298.15 | N/A | McEachern and Kilpatrick, 1964 | P = 53.14 kPa; DH |
31.2 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 316. K.; AC |
29.8 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 318. K.; AC |
30.3 | 305. | N/A | Brazhnikov, Peshchenko, et al., 1976 | Based on data from 296. to 314. K.; AC |
30.1 | 288. | N/A | Nicolini and Laffitte, 1949 | Based on data from 273. to 308. K.; AC |
Entropy of vaporization
ΔvapS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
96.9 | 298.15 | McEachern and Kilpatrick, 1964 | P; DH |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
273. to 308. | 4.03675 | 1068.35 | -50.409 | Nicolini and Laffitte, 1949, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.3316 | 168.01 | McEachern and Kilpatrick, 1964 | DH |
8.33 | 168. | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
49.59 | 168.01 | McEachern and Kilpatrick, 1964 | DH |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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, Condensed phase thermochemistry data, Phase change 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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Due to licensing restrictions, this spectrum cannot be downloaded.
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, Condensed phase thermochemistry data, Phase change 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, Condensed phase thermochemistry data, Phase change 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]
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, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure S°gas Entropy of gas at standard conditions S°liquid Entropy of liquid 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 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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