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 Copy

  
• IUPAC Standard InChIKey: SQYNKIJPMDEDEG-UHFFFAOYSA-N Copy
• 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:
  • cis-2,4,6-Trimethyl-1,3,5-trioxane
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change 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

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

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:
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

Enthalpy of vaporization

Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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 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

= 3

By formula: C₆H₁₂O₃ = 3C₂H₄O

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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]

Grimm and Patrick, 1923
Grimm, F.V.; Patrick, W.A., The Dielectric Constastants of Organic Liquids at the Boilin Point, J. Am. Chem. Soc., 1923, 45, 2794. [all data]

Paul and Schantz, 1919
Paul, T.; Schantz, K., The boiling point as indicator of purity and a new apparatus for its determination without thermometer correction., Arch. Pharm. (Weinheim, Ger.), 1919, 257, 87. [all data]

Hollmann, 1903
Hollmann, R., Physical and natural equilibria between the modifications of aldehyde, Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1903, 43, 129-59. [all data]

Von Reis, 1881
Von Reis, M.A., IV. The Specific Heat of Liquid Organic Compounds and its Relation to Molecular Weight., Ann. Phys. (Leipzig), 1881, 13, 447. [all data]

Bruhl, 1880
Bruhl, J.W., The Chemical Constitution of Organic Compounds in Relation to their Density and their Ability to Propagate Light, Justus Liebigs Ann. Chem., 1880, 203, 1. [all data]

Biltz, Fischer, et al., 1930
Biltz, W.; Fischer, W.; Wunnenberg, E., Molecular and Atomic Volumes. The Volume Requirements of Crystalline Organic Compounds and Low Temperatures, Z. Phys. Chem., Abt. A, 1930, 151, 13-55. [all data]

Cooper, 1928
Cooper, D.L., The Heat Cpacities of Acetaldehyde and Paraldehyde, and the Heat of Transformation of Acetaldehyde into Paraldehyde, Proc. Trans. N. S. Inst. Sci., Pt. 1, 1928, 17. 82-90. [all data]

Louguinine and Dupont, 1911
Louguinine, W.; Dupont, G., The heat of fusion of substances which melt at ordinary temperatures., Bull. Soc. Chim. Fr., 1911, 9, 219-224. [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]

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]

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, Phase change 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
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  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
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  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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