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
  • Reaction thermochemistry data
  • IR Spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Mass spectrum (electron ionization)
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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

Reaction 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: 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

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (2% CCl4 FOR 3800-1330, 2% CS2 FOR 1330-450 CM^-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

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

• gas

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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References

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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]

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]

Tiess, 1984
Tiess, D., Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30, Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [all data]

Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

MHA, 9999
MHA, Directorate of ForensicScience., Forensic Toxicology, 9999. [all data]

van Loon, Linssen, et al., 2005
van Loon, W.A.M.; Linssen, J.P.H.; Legger, A.; Posthumus, M.A.; Voragen, A.G.J., Identification and olfactometry of French fries flavour extracted at mouth conditions, Food Chem., 2005, 90, 3, 417-425, https://doi.org/10.1016/j.foodchem.2004.05.005 . [all data]

Berdague, Denoyer, et al., 1991
Berdague, J.-L.; Denoyer, C.; Le Quéré, J.-L.; Semon, E., Volatile components of dry-cured ham, J. Agric. Food Chem., 1991, 39, 7, 1257-1261, https://doi.org/10.1021/jf00007a012 . [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [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/technical_series₁997-01-01₁.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]

Vernin, Metzger, et al., 1993
Vernin, G.; Metzger, J.; Sultan, A.A.M.; El-Shafei, A.K.; Párkányi, C., Heterocyclic compounds in model systems for the Maillard reaction. Reactions of aldehydes with ammonium sulfide in the presence or absence of acetoin, Am. Chem. Soc. Symp. Ser., 1993, 528, 36-55. [all data]

Notes

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• Symbols used in this document:
  

  S°gas	Entropy of gas at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

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