1,3-Dioxolane

• Formula: C₃H₆O₂
• Molecular weight: 74.0785
• IUPAC Standard InChI:
  

  InChI=1S/C3H6O2/c1-2-5-3-4-1/h1-3H2 Download the identifier in a file.

• IUPAC Standard InChIKey: WNXJIVFYUVYPPR-UHFFFAOYSA-N
• CAS Registry Number: 646-06-0
• 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: Ethylene glycol formal; Formal glycol; Glycolformal; 1,3-Dioxacyclopentane; 1,3-Dioxolan; 1,3-Dioxole, dihydro-; Dioxolan; Dioxolane
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • Gas phase ion energetics data
  • Gas Chromatography
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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
fH°gas	-301.7 ± 2.2	kJ/mol	Ccb	Pihlaja and Heikklia, 1969	ALS
Quantity	Value	Units	Method	Reference	Comment
S°gas	310.5 ± 4.1	J/mol*K	N/A	Clegg G.A., 1969	This calorimetric value of S(298.15 K) is 10.8 J/mol*K larger than that obtained by statistical calculation [ Dorofeeva O.V., 1992]. However, statistical value agrees well with estimation by difference method [ Dorofeeva O.V., 1992].; GT

Constant pressure heat capacity of gas

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
fH°liquid	-337.2 ± 1.4	kJ/mol	Ccb	Pihlaja and Heikklia, 1969	ALS
Quantity	Value	Units	Method	Reference	Comment
cH°liquid	-1700.8 ± 1.4	kJ/mol	Ccb	Pihlaja and Heikklia, 1969	Corresponding «DELTA»fHºliquid = -337.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
cH°liquid	-1700.	kJ/mol	Ccb	Fletcher, Mortimer, et al., 1959	Corresponding «DELTA»fHºliquid = -338. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
cH°liquid	-1705.	kJ/mol	Ccb	Skuratov, Strepikheev, et al., 1957	Combustion for liq at 293 K; Corresponding «DELTA»fHºliquid = -333. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°liquid	280.2	J/mol*K	N/A	Clegg and Melia, 1969	DH

Constant pressure heat capacity of liquid

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, Kenneth Kroenlein director
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
Tboil	347.7	K	N/A	Aldrich Chemical Company Inc., 1990	BS
Tboil	348.75	K	N/A	Anonymous, 1968	TRC
Quantity	Value	Units	Method	Reference	Comment
Tfus	175.85	K	N/A	Anonymous, 1968	TRC
Tfus	175.9	K	N/A	Anonymous, 1955	Uncertainty assigned by TRC = 0.6 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Ttriple	175.93	K	N/A	Clegg and Melia, 1969	Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Quantity	Value	Units	Method	Reference	Comment
vapH°	35.5	kJ/mol	N/A	Pihlaja and Heikklia, 1969	DRB
vapH°	36. ± 0.4	kJ/mol	V	Fletcher, Mortimer, et al., 1959	ALS

Enthalpy of vaporization

vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
34.6	326.	A	Wu and Sandler, 1989	Based on data from 305. - 347. K.; AC
35.8	295.	A	Stephenson and Malanowski, 1987	Based on data from 280. - 323. K.; AC
33.7	339.	N/A	Castellari, Francesconi, et al., 1982	Based on data from 321. - 357. K.; AC
33.7	326.	N/A	Francesconi, Castellari, et al., 1980	Based on data from 306. - 346. K.; AC
34.1	296.	N/A	Cherkasskaya, Tur, et al., 1968	Based on data from 280. - 355. K. See also Boublik, Fried, et al., 1984.; AC

Antoine Equation Parameters

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

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Enthalpy of fusion

fusH (kJ/mol)	Temperature (K)	Reference	Comment
6.57	175.9	Domalski and Hearing, 1996	AC

Entropy of fusion

fusS (J/mol*K)	Temperature (K)	Reference	Comment
18.8	142.4	Domalski and Hearing, 1996	CAL
37.33	175.9

Enthalpy of phase transition

Htrs (kJ/mol)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
2.677	142.4	crystaline, II	crystaline, I	Clegg and Melia, 1969	DH
6.567	175.93	crystaline, I	liquid	Clegg and Melia, 1969	DH

Entropy of phase transition

Strs (J/mol*K)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
18.8	142.4	crystaline, II	crystaline, I	Clegg and Melia, 1969	DH
37.3	175.93	crystaline, I	liquid	Clegg and Melia, 1969	DH

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

Gas Phase Spectrum

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Additional Data

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

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), Notes

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

Pihlaja and Heikklia, 1969
Pihlaja, K.; Heikklia, J., Enthalpies of formation of cyclic acetals. 1,3-dioxolane, 2-methyl-1,3-dioxolane, and 2,4-dimethyl-1,3-dioxolanes, Acta Chem. Scand., 1969, 23, 1053-1055. [all data]

Clegg G.A., 1969
Clegg G.A., Thermodynamics of polymerization of heterocyclic compounds. Part V. The heat capacity, entropy, enthalpy and free energy of 1,3-dioxolan and poly-1,3-dioxolan, Polymer, 1969, 10, 912-922. [all data]

Dorofeeva O.V., 1992
Dorofeeva O.V., Ideal gas thermodynamic properties of oxygen heterocyclic compounds. Part 1. Three-membered, four-membered and five-membered rings, Thermochim. Acta, 1992, 194, 9-46. [all data]

Fletcher, Mortimer, et al., 1959
Fletcher, S.E.; Mortimer, C.T.; Springall, H.D., Heats of combustion and molecular structure. Part VII. 1:3-dioxa- and 1:3:5-trioxa-cycloalkanes, J. Chem. Soc., 1959, 580-584. [all data]

Skuratov, Strepikheev, et al., 1957
Skuratov, S.M.; Strepikheev, A.A.; Shtekhter, S.M.; Volokhina, A.V., About the enthalpies of polymerization of cyclic formales, Dokl. Akad. Nauk SSSR, 1957, 117, 263-265. [all data]

Clegg and Melia, 1969
Clegg, G.A.; Melia, T.P., Thermodynamics of polymerization of heterocyclic compounds. Part V. The heat capacity, entropy, enthalpy and free energy of 1,3-dioxolan and poly-1,3-dioxolan, Polymer, 1969, 10(12), 912-922. [all data]

Inglese, Castagnolo, et al., 1981
Inglese, A.; Castagnolo, M.; Dell'Atti, A.; DeGiglio, A., Thermochim. Acta, 1981, 77-87. [all data]

Conti, Gianni, et al., 1976
Conti, G.; Gianni, P.; Matteoli, E.; Mengheri, M., Capacita termiche molari di alcuni composti organici mono- e bifunzionali nel liquido puro e in soluzione acquosa a 25C, Chim. Ind. (Milan), 1976, 58, 225. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Anonymous, 1968
Anonymous, X., Chemicals and Plastics Physical Properties, 1968, Union Carbide Corp., product bulletin, 1968. [all data]

Anonymous, 1955
Anonymous, R., , Am. Pet. Inst. Res. Proj. 45, Tech. Rep. 14, No. 1, Ohio State Univ., 1955. [all data]

Wu and Sandler, 1989
Wu, Huey S.; Sandler, Stanley I., Vapor-liquid equilibrium of 1,3-dioxolane systems, J. Chem. Eng. Data, 1989, 34, 2, 209-213, https://doi.org/10.1021/je00056a019 . [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]

Castellari, Francesconi, et al., 1982
Castellari, Carlo; Francesconi, Romolo; Comelli, Fabio, Vapor-liquid equilibriums in binary systems containing 1,3-dioxolane at isobaric conditions. 3. Binary mixtures of 1,3-dioxolane with o-, m-, and p-xylenes, J. Chem. Eng. Data, 1982, 27, 2, 156-158, https://doi.org/10.1021/je00028a017 . [all data]

Francesconi, Castellari, et al., 1980
Francesconi, Romolo; Castellari, Carlo; Arcelli, Antonio; Comelli, Fabio, Vapor-liquid equilibrium in mixtures of 1,3 dioxolane-water, Can. J. Chem. Eng., 1980, 58, 1, 113-121, https://doi.org/10.1002/cjce.5450580116 . [all data]

Cherkasskaya, Tur, et al., 1968
Cherkasskaya, E.L.; Tur, A.M.; Petrenkova, Z.F.; Lyubomilov, V.I., Zh. Prikl. Khim., 1968, 41, 11, 2553. [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]

Cherkaskaya, Petrenkova, et al., 1968
Cherkaskaya, E.L.; Petrenkova, Z.E.; Tur, A.M.; Lubinova, V.I., Phase Equilibrium of Liquid-Steam in System of Dioxolane-Water, Zh. Prikl. Khim. (Leningrad), 1968, 41, 2553-2554. [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]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  S°gas	Entropy of gas at standard conditions
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Htrs	Enthalpy of phase transition
  Strs	Entropy of phase transition
  cH°liquid	Enthalpy of combustion of liquid at standard conditions
  fH°gas	Enthalpy of formation of gas at standard conditions
  fH°liquid	Enthalpy of formation of liquid at standard conditions
  fusH	Enthalpy of fusion
  fusS	Entropy of fusion
  vapH	Enthalpy of vaporization
  vapH°	Enthalpy of vaporization at standard conditions

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