1,3-Dioxolane
- Formula: C3H6O2
- Molecular weight: 74.0785
- 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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Phase change data
Go To: Top, Gas phase ion energetics data, 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny 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 |
Quantity | Value | Units | Method | Reference | Comment |
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 |
ΔvapH° | 35.5 | kJ/mol | N/A | Pihlaja and Heikklia, 1969 | DRB |
ΔvapH° | 36. ± 0.4 | kJ/mol | V | Fletcher, Mortimer, et al., 1959 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
34.6 | 326. | A | Wu and Sandler, 1989 | Based on data from 305. to 347. K.; AC |
35.8 | 295. | A | Stephenson and Malanowski, 1987 | Based on data from 280. to 323. K.; AC |
33.7 | 339. | N/A | Castellari, Francesconi, et al., 1982 | Based on data from 321. to 357. K.; AC |
33.7 | 326. | N/A | Francesconi, Castellari, et al., 1980 | Based on data from 306. to 346. K.; AC |
34.1 | 296. | N/A | Cherkasskaya, Tur, et al., 1968 | Based on data from 280. to 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)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
280.9 to 355.3 | 4.11859 | 1237.377 | -48.735 | Cherkaskaya, Petrenkova, et al., 1968 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
6.57 | 175.9 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
18.8 | 142.4 | Domalski and Hearing, 1996 | CAL |
37.33 | 175.9 |
Enthalpy of phase transition
ΔHtrs (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
ΔStrs (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 |
Gas phase ion energetics data
Go To: Top, Phase change data, 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C3H6O2+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.9 | PE | Sweigart and Turner, 1972 | LLK |
10.02 | EI | Collin and Conde, 1966 | RDSH |
10.1 | PE | Sweigart and Turner, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H2O+ | 13.20 | ? | EI | Collin and Conde, 1966 | RDSH |
C2H3O+ | 14.14 | ? | EI | Collin and Conde, 1966 | RDSH |
C2H4O+ | 10.87 | CH2O | EI | Holmes, Terlouw, et al., 1976 | LLK |
C2H4O+ | 11.56 | ? | EI | Collin and Conde, 1966 | RDSH |
C2H5O+ | 12.45 | ? | EI | Collin and Conde, 1966 | RDSH |
C3H5O2+ | 10.38 | H | EI | Collin and Conde, 1966 | RDSH |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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, 1955
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 45, Tech. Rep. 14, No. 1, Ohio State Univ., 1955. [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]
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]
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]
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]
Sweigart and Turner, 1972
Sweigart, D.A.; Turner, D.W.,
Lone pair orbitals and their interactions studied by photoelectron spectroscopy. II. Equivalent orbitals in saturated oxygen and sulfur J. Heterocycl. Chem.,
J. Am. Chem. Soc., 1972, 94, 5599. [all data]
Collin and Conde, 1966
Collin, J.E.; Conde, G.,
L'ionisation et la dissociation des polyethers cycliques soumis a l'impact electronique,
Bull. Classe Sci. Acad. Roy. Belg., 1966, 52, 978. [all data]
Holmes, Terlouw, et al., 1976
Holmes, J.L.; Terlouw, J.K.; Lossing, F.P.,
The thermochemistry of C2H4O+ ions,
J. Phys. Chem., 1976, 80, 2860. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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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