Glycerin

• Formula: C₃H₈O₃
• Molecular weight: 92.0938
• IUPAC Standard InChI: InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2 Copy

  
• IUPAC Standard InChIKey: PEDCQBHIVMGVHV-UHFFFAOYSA-N Copy
• CAS Registry Number: 56-81-5
• 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: 1,2,3-Propanetriol; Glycerol; Glycerine; Glyceritol; Glycyl alcohol; Glyrol; Glysanin; Osmoglyn; Propanetriol; Trihydroxypropane; Synthetic glycerin; 90 Technical glycerin; Dagralax; Glycerin, anhydrous; Glycerin, synthetic; Ophthalgan; Synthetic glycerine; Vitrosupos; 1,2,3-Trihydroxypropane; 90 Technical glycerine; Clyzerin, wasserfrei; Grocolene; MOON; Star; Optim; Bulbold; Cristal; Emery 912; Incorporation factor; Pricerine 9091; Propane-1,2,3-triol; Emery 916; IFP; NSC 9230; Auralgan (Salt/Mix); Collyrium Fresh-Eye Drops (Salt/Mix)
• 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
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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
DRB - Donald R. Burgess, Jr.

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

Constant pressure heat capacity of solid

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Reduced pressure boiling point

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy of fusion

Entropy of fusion

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

 +  =  + 

By formula: C₃H₈O₃ + HNO₃ = C₃H₇NO₅ + H₂O

C₃H₉O₃⁺ +  = (C₃H₉O₃⁺ • )

By formula: C₃H₉O₃⁺ + C₃H₈O₃ = (C₃H₉O₃⁺ • C₃H₈O₃)

Bond type: Hydrogen bonds of the type OH-O between organics

Free energy of reaction

 +  =  + 

By formula: C₃H₈O₃ + HNO₃ = C₃H₇NO₅ + H₂O

 + 3 =  + 3

By formula: C₃H₈O₃ + 3HNO₃ = C₃H₅N₃O₉ + 3H₂O

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, References, Notes

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

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
MM - Michael M. Meot-Ner (Mautner)

Proton affinity at 298K

Gas basicity at 298K

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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 by: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C₃H₉O₃⁺ +  = (C₃H₉O₃⁺ • )

By formula: C₃H₉O₃⁺ + C₃H₈O₃ = (C₃H₉O₃⁺ • C₃H₈O₃)

Bond type: Hydrogen bonds of the type OH-O between organics

Free energy of reaction

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Notes

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

Bastos, Nilsson, et al., 1988
Bastos, M.; Nilsson, S-O.; Ribeiro Da Silva, M.D.M.C.; Ribeiro Da Silva, M.A.V.; Wadso, I., Thermodynamic properties of glycerol enthalpies of combustion and vaporization and the heat capacity at 298.15 K. Enthalpies of solution in water at 288.15, 298.15, and 308.15 K, J. Chem. Thermodyn., 1988, 20, 1353-1359. [all data]

Parks, West, et al., 1946
Parks, G.S.; West, T.J.; Naylor, B.F.; Fujii, P.S.; McClaine, L.A., Thermal data on organic compounds. XXIII. Modern combustion data for fourteen hydrocarbons and five polyhydroxy alcohols, J. Am. Chem. Soc., 1946, 68, 2524-2527. [all data]

Parks and Manchester, 1952
Parks, G.S.; Manchester, K.E., The heats of solution of erythritol, mannitol and dulcitol; combustion values for liquid polyhydroxy alcohols, J. Am. Chem. Soc., 1952, 74, 3435-34. [all data]

Emery and Benedict, 1911
Emery, A.G.; Benedict, F.G., The heat of combustion of compounds of physiological importance, Am. J. Physiol., 1911, 28, 301-307. [all data]

Ahlberg, Blanchard, et al., 1937
Ahlberg, J.E.; Blanchard, E.R.; Lundberg, W.O., The heat capacities of benzene, methyl alcohol and glycerol at very low temperatures, J. Chem. Phys., 1937, 5, 537-551. [all data]

Chen and Ge, 1982
Chen, Z.S.; Ge, X.S., A multifunctional apparatus for the simultaneous measurement of the specific heat, thermal conductivity and heat of fusion of materials undergoing phase transformations, Proc. Symp. Thermophys. Prop., 8th, 1982, (2), 115-121. [all data]

Atalla, El-Sharkawy, et al., 1981
Atalla, S.R.; El-Sharkawy, A.A.; Gasser, F.A., Measurement of thermal properties of liquids with an AC heated-wire technique, Inter. J. Thermophys., 1981, 2(2), 155-162. [all data]

Murthy and Subrahmanyam, 1977
Murthy, N.M.; Subrahmanyam, S.V., Behaviour of excess heat capacity of aqueous non-electrolytes, Indian J. Pure Appl. Phys., 1977, 15, 485-489. [all data]

Paz Andrade, Paz, et al., 1970
Paz Andrade, M.I.; Paz, J.M.; Recacho, E., Contribucion a la microcalorimetria de los calores especificos de solidos y liquidos, An. Quim., 1970, 66, 961-967. [all data]

Omel'chenko, 1962
Omel'chenko, F.S., On the heat capacity of glycerol, Izv. Vysshikh. Uchebn. Zaved., Pishchevaya Tekhnol., 1962, (3), 97-98. [all data]

Rabinovich and Nikolaev, 1962
Rabinovich, I.B.; Nikolaev, P.N., Isotopic effect in the specific heat of some deutero compounds, Dokl. Akad. Nauk, 1962, SSSR 142, 1335-1338. [all data]

Ernst, Watkins, et al., 1936
Ernst, R.C.; Watkins, C.H.; Ruwe, H.H., The physical properties of the ternary system ethyl alcohol-glycerin-water, J. Phys. Chem., 1936, 40, 627-635. [all data]

Parks, Kelley, et al., 1929
Parks, G.S.; Kelley, K.K.; Huffman, H.M., Thermal data on organic compounds. V. A revision of the entropies and free energies of nineteen organic compounds, J. Am. Chem. Soc., 1929, 51, 1969-1973. [all data]

Gibson and Giauque, 1923
Gibson, G.E.; Giauque, W.F., The third law of thermodynamics. Evidence from the specific heats of glycerol that the entropy of a glass exceeds that of a crystal at the absolute zero, J. Am. Chem. Soc., 1923, 45, 93-104. [all data]

Simon, 1922
Simon, F., Untersuchungen über die spezifische Wärme bei tiefen Temperaturen, Ann. Physik. [4], 1922, 68, 241-280. [all data]

Volmer and Marder, 1931
Volmer, M.; Marder, M., Zur theorie der linearen kristallistionsgeschwindigkeit unterkuhlter schmelzen und unterkuhlter fester modifikationen, Z. Physik. Chem., 1931, 154A, 97-112. [all data]

Wilhoit, Chao, et al., 1985
Wilhoit, R.C.; Chao, J.; Hall, K.R., Thermodynamic Properties of Key Organic Compounds in the Carbon Range C1 to C4. Part 1. Properties of Condensed Phases, J. Phys. Chem. Ref. Data, 1985, 14, 1. [all data]

Nikitin, Pavlov, et al., 1993
Nikitin, E.D.; Pavlov, P.A.; Skripov, P.V., Measurement of the critical properties of thermally unstable substances and mixtures by the pulse-heating method, J. Chem. Thermodyn., 1993, 25, 869-80. [all data]

Ross and Heideger, 1962
Ross, G.R.; Heideger, W.J., Vapor pressure of glycerol, J. Chem. Eng. Data, 1962, 7, 505-507. [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]

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]

Dykyj, 1970
Dykyj, J., Petrochemica, 1970, 10, 2, 51. [all data]

Cammenga, Schulze, et al., 1977
Cammenga, Heiko K.; Schulze, Friedrich W.; Theuerl, Wilhelm, Vapor pressure and evaporation coefficient of glycerol, J. Chem. Eng. Data, 1977, 22, 2, 131-134, https://doi.org/10.1021/je60073a004 . [all data]

Nováková and Novák, 1977
Nováková, N.; Novák, J., Measurement of heats of vaporization by means of a gas chromatograph, Journal of Chromatography A, 1977, 135, 1, 13-24, https://doi.org/10.1016/S0021-9673(00)86297-4 . [all data]

McFeely and Somorjai, 1972
McFeely, F.R.; Somorjai, G.A., Vaporization kinetics of hydrogen-bonded liquids, J. Phys. Chem., 1972, 76, 6, 914-918, https://doi.org/10.1021/j100650a022 . [all data]

Richardson, 1886
Richardson, Arthur, LXXIII.?Determinations of vapour-pressures of alcohols and organic acids, and the relations existing between the vapour-pressures of the alcohols and organic acids, J. Chem. Soc., Trans., 1886, 49, 761, https://doi.org/10.1039/ct8864900761 . [all data]

Richardson, 1886, 2
Richardson, A., LXXIII. Determinations of Vapour-Pressures of Alcohols and Organic Acids, and the Relations Existing Between the Vapour-Pressures of the Alcohols and Organic Acids, J. Chem. Soc., 1886, 49, 761-776, https://doi.org/10.1039/ct8864900761 . [all data]

Yoshida, 1944
Yoshida, U., Structural relaxation of amorphous solids and the cybotactic structure of super-cooled liquids, Mem. Coll. Sci. Kyoto Imp. Univ., 1944, 24A, 135-148. [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Kazakov, Kirpichev, et al., 1990
Kazakov, A.I.; Kirpichev, E.P.; Lagodzinskaya, G.V.; Andrienko, L.P.; Yunda, N.G.; Korolev, A.M.; Rubstov, Yu.I.; Manelis, G.B.; Eremenko, L.T., Study of nitration equilibrium in the glycerin-aqueous nitric acid system. 2. Changes in ΔH and ΔS in the nitration reaction, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 1565-1570. [all data]

Tsvetkov, Sopin, et al., 1986
Tsvetkov, V.G.; Sopin, V.P.; Tsvetkova, L.Ya.; Marchenko, G.N., Enthalpy of reaction of nitric acid with some organic compounds, J. Gen. Chem. USSR, 1986, 56, 471-474. [all data]

Sunner, Kulatunga, et al., 1986
Sunner, J.A.; Kulatunga, R.; Kebarle, P., Fast Atom Bombardment Mass Spectrometry and Gas Phase Basicities, Anal. Chem., 1986, 58, 7, 1312, https://doi.org/10.1021/ac00298a010 . [all data]

Kazakov, Lagodzinskaya, et al., 1989
Kazakov, A.I.; Lagodzinskaya, E.P.; Kirpichev, E.P.; Andrienko, L.P.; Yunda, N.G.; Korolev, A.M.; Robtsov, Yu.I.; Manelis, G.V.; Eremenko, L.T., Thermodynamics of nitration of glycerol, Dokl. Phys. Chem. (Engl. Transl.), 1989, 305, 287-291. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Bouchoux, Buisson, et al., 2003
Bouchoux, G.; Buisson, D.A.; Bourcier, S.; Sablier, M., Application of the kinetic method to bifunctional bases. ESI tandem quadrupole experiments, Int. J. Mass Spectrom., 2003, 228, 1035. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  Cp,solid	Constant pressure heat capacity of solid
  Pc	Critical pressure
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  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
  ΔrG°	Free energy of reaction at standard conditions
  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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