Cyclododecane
- Formula: C12H24
- Molecular weight: 168.3190
- IUPAC Standard InChI: InChI=1S/C12H24/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-12H2
- IUPAC Standard InChIKey: DDTBPAQBQHZRDW-UHFFFAOYSA-N
- CAS Registry Number: 294-62-2
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔcH°gas | -1777. | kcal/mol | Ccb | Smith and Easley, 1963 | Corresponding ΔfHºgas = -172. kcal/mol (simple calculation by NIST; no Washburn corrections) |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔcH°solid | -1840.42 | kcal/mol | Ccb | Gollis, Belenyessy, et al., 1962 | Corresponding ΔfHºsolid = -107.97 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -1875.10 ± 0.31 | kcal/mol | Ccb | Coops, Van Kamp, et al., 1960 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1875.0 ± 0.31 kcal/mol; Corresponding ΔfHºsolid = -73.298 kcal/mol (simple calculation by NIST; no Washburn corrections) |
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
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 333.8 | K | N/A | Drotloff and Moller, 1987 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.3 K; TRC |
| Tfus | 332.5 | K | N/A | Mueller, Padeken, et al., 1965 | Uncertainty assigned by TRC = 1. K; TRC |
| Tfus | 316. | K | N/A | Gollis, Belenyessy, et al., 1962, 2 | Uncertainty assigned by TRC = 1.66 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 15.1 | kcal/mol | CGC | Chickos, Hesse, et al., 1998 | AC |
| ΔvapH° | 15.0 | kcal/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 403. to 453. K.; AC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 18.2 | kcal/mol | CGC-DSC | Chickos, Hesse, et al., 1998 | AC |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 12.6 | 401. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 386. to 441. K. See also Meyer and Hotz, 1976.; AC |
| 11.9 | 455. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 440. to 529. K. See also Meyer and Hotz, 1976.; AC |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 3.54 | 333.8 | Drotloff and Möller, 1987 | AC |
Entropy of fusion
| ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 0.722 | 199. | Drotloff and Moller, 1987 | CAL |
| 10.60 | 333.8 |
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
+ 2
=
By formula: C12H20 + 2H2 = C12H24
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -61.75 ± 0.40 | kcal/mol | Chyd | Turner, Jarrett, et al., 1973 | liquid phase; solvent: Acetic acid |
| ΔrH° | -61.7 | kcal/mol | Chyd | Sicher, Svoboda, et al., 1968 | liquid phase; solvent: Acetic acid |
+
=
By formula: H2 + C12H22 = C12H24
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -26.8 | kcal/mol | Chyd | Sicher, Svoboda, et al., 1968 | liquid phase; solvent: Acetic acid |
+
=
By formula: C12H22 + H2 = C12H24
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -26.3 | kcal/mol | Chyd | Sicher, Svoboda, et al., 1968 | liquid phase; solvent: Acetic acid |
Gas phase ion energetics 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.72 ± 0.03 | PI | Golubitskii, Kulikov, et al., 1979 | LLK |
| 10.04 ± 0.05 | EI | Puttemans, 1974 | LLK |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- SOLID (PELLET); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
- SOLUTION (CCl4 (VS. CCl4) FOR 4000-1200, CS2 (VS. CS2) FOR 1200-450 CM-1); CARY 90 (GRATING); (GLUED); 2 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | OV-1 | 150. | 1338.3 | Rudenko and Rudenko, 2005 | He; Column diameter: 0.25 mm |
| Capillary | OV-1 | 170. | 1351.6 | Rudenko and Rudenko, 2005 | He; Column diameter: 0.25 mm |
| Capillary | OV-1 | 190. | 1372.4 | Rudenko and Rudenko, 2005 | He; Column diameter: 0.25 mm |
| Capillary | OV-1 | 150. | 1338.3 | Rudenko and Rudenko, 2000 | He; Column diameter: 0.25 mm |
| Capillary | OV-1 | 170. | 1351.6 | Rudenko and Rudenko, 2000 | He; Column diameter: 0.25 mm |
| Capillary | OV-1 | 190. | 1372.4 | Rudenko and Rudenko, 2000 | He; Column diameter: 0.25 mm |
| Capillary | Methyl Silicone | 160. | 1360. | Boneva and Balbolov, 1993 | 50. m/0.25 mm/1.0 μm, N2 |
| Capillary | Methyl Silicone | 170. | 1370. | Boneva and Balbolov, 1993 | 50. m/0.25 mm/1.0 μm, N2 |
| Capillary | Methyl Silicone | 180. | 1378. | Boneva and Balbolov, 1993 | 50. m/0.25 mm/1.0 μm, N2 |
| Capillary | OV-1 | 100. | 1323.7 | Engewald, Billing, et al., 1987 | Column length: 50. m; Column diameter: 0.3 mm |
| Capillary | Squalane | 120. | 1326. | Engewald, Epsch, et al., 1974 | N2; Column length: 100. m; Column diameter: 0.23 mm |
| Capillary | Squalane | 120. | 1330. | Schomburg, 1967 | Ar; Column length: 100. m |
| Capillary | Squalane | 120. | 1325. | Schomburg, 1966 | |
| Packed | Apiezon L | 130. | 1384. | Wehrli and Kováts, 1959 | Celite; Column length: 2.25 m |
Kovats' RI, polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | Carbowax 40M | 150. | 1497.2 | Rudenko and Rudenko, 2005 | He; Column diameter: 0.25 mm |
| Capillary | Carbowax 40M | 170. | 1516.9 | Rudenko and Rudenko, 2005 | He; Column diameter: 0.25 mm |
| Capillary | Carbowax 40M | 190. | 1549.3 | Rudenko and Rudenko, 2005 | He; Column diameter: 0.25 mm |
| Capillary | Carbowax 40M | 150. | 1497.2 | Rudenko and Rudenko, 2000 | He; Column diameter: 0.25 mm |
| Capillary | Carbowax 40M | 170. | 1516.9 | Rudenko and Rudenko, 2000 | He; Column diameter: 0.25 mm |
| Capillary | Carbowax 40M | 190. | 1549.3 | Rudenko and Rudenko, 2000 | He; Column diameter: 0.25 mm |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-1 | 1316. | Peng, 2000 | 15. m/0.53 mm/1. μm, He; Program: 40C(3min) => 8C/min => 200(1min) => 5C/min => 300C(25min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 1519. | Bertoli, Menichini, et al., 2004 | 30. m/0.25 mm/0.25 μm, N2, 60. C @ 10. min, 5. K/min; Tend: 220. C |
| Capillary | DB-Wax | 1521. | Peng, 2000 | 15. m/0.53 mm/1. μm, He, 40. C @ 3. min, 5. K/min, 220. C @ 30. min |
| Capillary | HP-Wax | 1510. | Peng, 2000 | 15. m/0.53 mm/1. μm, He, 40. C @ 3. min, 5. K/min, 220. C @ 30. min |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Squalane | 1326. | Chen, 2008 | Program: not specified |
| Capillary | Methyl Silicone | 1384. | N/A | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Smith and Easley, 1963
Smith, J.O.; Easley, K.W.,
Ortho-substituted bicyclohexyl hydrocarbons as high energy fuels, Patent No. 3,113,425 to Monsanto Research Corp., Everett, MA, USA 12/10/63, 1963, 1. [all data]
Gollis, Belenyessy, et al., 1962
Gollis, M.H.; Belenyessy, L.I.; Gudzinowicz, B.J.; Koch, S.D.; Smith, J.O.; Wineman, R.J.,
Evaluation of pure hydrocarbons as jet fuels,
J. Chem. Eng. Data, 1962, 7, 331-316. [all data]
Coops, Van Kamp, et al., 1960
Coops, J.; Van Kamp, H.; Lambregts, W.A.; Visser, B.J.; Dekker, H.,
Thermal quantities of cycloparaffins. Part IV. Heats of combustion of cycloparaffins with 10-17 C atoms,
Rec. Trav. Chim. Pays/Bas, 1960, 79, 1226-1234. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Drotloff and Moller, 1987
Drotloff, H.; Moller, M.,
On the phase transitions of cycloalkanes,
Thermochim. Acta, 1987, 112, 1, 57, https://doi.org/10.1016/0040-6031(87)88079-6
. [all data]
Mueller, Padeken, et al., 1965
Mueller, E.; Padeken, H.G.; Salamon, M.; Fiedler, G.,
Direct Photooxidation of Cycloalkanes,
Chem. Ber., 1965, 98, 1893-1909. [all data]
Gollis, Belenyessy, et al., 1962, 2
Gollis, M.H.; Belenyessy, L.I.; Gudzinowicz, B.J.; Koch, S.D.; Smith, J.O.; Wineman, R.J.,
Evaluation of pure hydrocarbons as jet fuels.,
J. Chem. Eng. Data, 1962, 7, 311-6. [all data]
Chickos, Hesse, et al., 1998
Chickos, James; Hesse, Donald; Hosseini, Sarah; Nichols, Gary; Webb, Paul,
Sublimation enthalpies at 298.15K using correlation gas chromatography and differential scanning calorimetry measurements,
Thermochimica Acta, 1998, 313, 2, 101-110, https://doi.org/10.1016/S0040-6031(97)00432-2
. [all data]
Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G.,
Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times,
Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3
. [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]
Meyer and Hotz, 1976
Meyer, Edwin F.; Hotz, Carol A.,
Cohesive energies in polar organic liquids. 3. Cyclic ketones,
J. Chem. Eng. Data, 1976, 21, 3, 274-279, https://doi.org/10.1021/je60070a035
. [all data]
Drotloff and Möller, 1987
Drotloff, Hansotto; Möller, Martin,
On the phase transitions of cycloalkanes,
Thermochimica Acta, 1987, 112, 1, 57-62, https://doi.org/10.1016/0040-6031(87)88079-6
. [all data]
Turner, Jarrett, et al., 1973
Turner, R.B.; Jarrett, A.D.; Goebel, P.; Mallon, B.J.,
Heats of hydrogenation. 9. Cyclic acetylenes and some miscellaneous olefins,
J. Am. Chem. Soc., 1973, 95, 790-792. [all data]
Sicher, Svoboda, et al., 1968
Sicher, J.; Svoboda, M.; Mallon, B.J.; Turner, R.B.,
Stereochemical studies. Part XLVII. Conformational analysis of many-membered ring compounds. The cyclododecenes,
J. Chem. Soc. B, 1968, 441-447. [all data]
Golubitskii, Kulikov, et al., 1979
Golubitskii, A.E.; Kulikov, N.S.; Zyakun, A.M.; Valovoi, V.A.; Alekseev, A.M.; Volkov, V.N.,
Photoionization mass spectra of alicyclic compounds with various substituents, and their ionization energies and appearance energies,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1979, 11, 2602. [all data]
Puttemans, 1974
Puttemans, J.P.,
Ionisation de cycloalcanes (C5 a C12) en spectroscopie photoelectronique et par impact electronique,
Ing. Chim. (Brussels), 1974, 56, 64. [all data]
Rudenko and Rudenko, 2005
Rudenko, B.A.; Rudenko, G.I.,
Gas chromatography with open tubular columns of cyclododecane derivatives,
J. Anal. Chem. USSR (Engl. Transl.), 2005, 60, 4, 345-348. [all data]
Rudenko and Rudenko, 2000
Rudenko, B.A.; Rudenko, G.I.,
Capillary chromatography of cyclododecane derivatives, Proceedings, 23rd ISCC; CD-ROM, 2000, retrieved from http://www.richrom.com/assets/CD23PDF. [all data]
Boneva and Balbolov, 1993
Boneva, S.; Balbolov, E.,
Capillary gas chromatography of hydrogenation products of 1,5,9-cyclododecatriene stereoisomers,
Chromatographia, 1993, 37, 5/6, 277-280, https://doi.org/10.1007/BF02278633
. [all data]
Engewald, Billing, et al., 1987
Engewald, W.; Billing, U.; Welsch, T.; Haufe, G.,
Structure-retention correlations of hydrocarbons in gas-liquid and gas-solid chromatography. Cycloalkenes and cycloalkadienes,
Chromatographia, 1987, 23, 8, 590-594, https://doi.org/10.1007/BF02324870
. [all data]
Engewald, Epsch, et al., 1974
Engewald, W.; Epsch, K.; Graefe, J.; Welsch, Th.,
Molekülstruktur und retentionsverhalten. II. Retentionsverhalten cycloaliphatischer kohlenwasser-stoffe bei der gas-adsorptions- und gas-verteilungschromatographie,
J. Chromatogr., 1974, 91, 623-631, https://doi.org/10.1016/S0021-9673(01)97943-9
. [all data]
Schomburg, 1967
Schomburg, G.,
Struktur und Retentionsverhalten von Offenkettigen und Cyclischen Kohlenwasserstoffen und Deren Einfacher Substitutionsprodukte,
Anal. Chim. Acta., 1967, 38, 45-64, https://doi.org/10.1016/S0003-2670(01)80560-2
. [all data]
Schomburg, 1966
Schomburg, G.,
Gaschromatographische Retentionsdaten und struktur chemischer verbindungen. III. Alkylverzweigte und ungesättigte cyclische Kohlenwasserstoffe,
J. Chromatogr., 1966, 23, 18-41, https://doi.org/10.1016/S0021-9673(01)98653-4
. [all data]
Wehrli and Kováts, 1959
Wehrli, A.; Kováts, E.,
Gas-chromatographische Charakterisierung ogranischer Verbindungen. Teil 3: Berechnung der Retentionsindices aliphatischer, alicyclischer und aromatischer Verbindungen,
Helv. Chim. Acta, 1959, 7, 7, 2709-2736, https://doi.org/10.1002/hlca.19590420745
. [all data]
Peng, 2000
Peng, C.T.,
Prediction of retention indices. V. Influence of electronic effects and column polarity on retention index,
J. Chromatogr. A, 2000, 903, 1-2, 117-143, https://doi.org/10.1016/S0021-9673(00)00901-8
. [all data]
Bertoli, Menichini, et al., 2004
Bertoli, A.; Menichini, F.; Noccioli, C.; Morelli, I.; Pistelli, L.,
Volatile constituents of different organs of Psoralea bituminosa L.,
Flavour Fragr. J., 2004, 19, 2, 166-171, https://doi.org/10.1002/ffj.1315
. [all data]
Chen, 2008
Chen, H.-F.,
Quantitative prediction of gas chromatography retention indices with support vector machines, radial basis neutral networks and multiple linear regression,
Anal. Chim. Acta, 2008, 609, 1, 24-36, https://doi.org/10.1016/j.aca.2008.01.003
. [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, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
Tfus Fusion (melting) point ΔcH°gas Enthalpy of combustion of gas at standard conditions ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔsubH° Enthalpy of sublimation 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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