Paraldehyde
- Formula: C6H12O3
- Molecular weight: 132.1577
- IUPAC Standard InChI: InChI=1S/C6H12O3/c1-4-7-5(2)9-6(3)8-4/h4-6H,1-3H3
- IUPAC Standard InChIKey: SQYNKIJPMDEDEG-UHFFFAOYSA-N
- CAS Registry Number: 123-63-7
- 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. - Stereoisomers:
- Other names: 1,3,5-Trioxane, 2,4,6-trimethyl-; s-Trioxane, 2,4,6-trimethyl-; s-Trimethyltrioxymethylene; Acetaldehyde trimer; Elaldehyde; Paraacetaldehyde; Paracetaldehyde; Paral; Pcho; 1,3,5-Trimethyl-2,4,6-trioxane; 2,4,6-Trimethyl-s-trioxane; 2,4,6-Trimethyl-1,3,5-trioxane; 2,4,6-Trimethyl-1,3,5-trioxan; Paraldehyd; Paraldeide; Triacetaldehyde; 2,4,6-Trimethyl-1,3,5-trioxaan; 2,4,6-Trimethyl-1,3,5-trioxacyclohexane; 2,4,6-Trimetil-1,3,5-triossano; Rcra waste number U182; UN 1264; Trimethyl trioxane; NSC 9799
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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:
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 | -636. ± 3. | kJ/mol | Ccb | Pihlaja and Tuomi, 1970 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°gas | 374.4 ± 5.0 | J/mol*K | N/A | Clegg G.A., 1969 | GT |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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:
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 |
|---|---|---|---|---|---|
| ΔfH°liquid | -681.8 ± 2.6 | kJ/mol | Ccb | Pihlaja and Tuomi, 1970 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -3394.2 ± 2.6 | kJ/mol | Ccb | Pihlaja and Tuomi, 1970 | Corresponding ΔfHºliquid = -681.82 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -3389. | kJ/mol | Ccb | Fletcher, Mortimer, et al., 1959 | Corresponding ΔfHºliquid = -687.0 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -3390. ± 2. | kJ/mol | Ccb | Cass, Springall, et al., 1955 | Corresponding ΔfHºliquid = -686.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 289.4 | J/mol*K | N/A | Clegg and Melia, 1969 | Extrapolation below 80 K, 61.1 J/mol*K.; DH |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 257.3 | 298.15 | Clegg and Melia, 1969 | T = 80 to 310 K.; DH |
| 254.0 | 306.6 | Phillip, 1939 | DH |
| 250.2 | 298. | von Reis, 1881 | T = 293 to 400 K.; DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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 by: 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
3 =
By formula: 3C2H4O = C6H12O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -87. ± 6. | kJ/mol | Cm | Krasnov, Ozherel'eva, et al., 1983 | liquid phase; solvent: Nonaqueous; Trimerization |
| ΔrH° | -98.1 | kJ/mol | Eqk | Busfield, Lee, et al., 1973 | gas phase |
= 3
By formula: C6H12O3 = 3C2H4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 98.1 | kJ/mol | Eqk | Busfield, Lee, et al., 1973 | gas phase; At 292-313 K |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Pihlaja and Tuomi, 1970
Pihlaja, K.; Tuomi, M.,
Bond-Bond interactions in organic oxygen compounds. Part II. Anomalous stablization in cis-2,4,6-trimethyl-1,3,5-trioxane,
Suom. Kemistil., 1970, 43, 224-226. [all data]
Clegg G.A., 1969
Clegg G.A.,
Thermodynamics of polymerization of heterocyclic compounds. Part IV. The heat capacity, entropy, enthalpy and free energy of paraldehyde,
Makromol. Chem., 1969, 123, 194-202. [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]
Cass, Springall, et al., 1955
Cass, R.C.; Springall, H.D.; White, T.R.,
The anomalous heat of combustion of paraldehyde,
Chem. Ind. (London), 1955, 387-388. [all data]
Clegg and Melia, 1969
Clegg, G.A.; Melia, T.P.,
Thermodynamics of polymerization of heterocyclic compounds. Part IV. The heat capacity, entropy, enthalpy and free energy of paraldehyde,
Makromol. Chem., 1969, 123, 194-202. [all data]
Phillip, 1939
Phillip, N.M.,
Adiabatic and isothermal compressibilities of liquids,
Proc. Indian Acad. Sci., 1939, A9, 109-120. [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]
Krasnov, Ozherel'eva, et al., 1983
Krasnov, V.L.; Ozherel'eva, N.K.; Trub, E.P.; Tsvetkov, V.G.; Bodrikov, I.V.,
Trimerization of aldehydes under the action of sulfur dioxide,
J. Gen. Chem. USSR, 1983, 53, 2135-2138. [all data]
Busfield, Lee, et al., 1973
Busfield, W.K.; Lee, R.M.; Merifold, D.,
Gas phase equilibrium between acetaldehyde and paraldehyde, thermodynamic values for the trimerisation of acetaldehyde and the polymerisability of paraldehyde,
J. Chem. Soc. Faraday Trans. 1, 1973, 69, 936-940. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°gas Entropy of gas at standard conditions S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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