Naphthalene, decahydro-
- Formula: C10H18
- Molecular weight: 138.2499
- IUPAC Standard InChIKey: NNBZCPXTIHJBJL-UHFFFAOYSA-N
- CAS Registry Number: 91-17-8
- 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: Bicyclo[4.4.0]decane; Dec; Decahydronaphthalene; Decalin; Dekalin; Naphthan; Perhydronaphthalene; Decanhydronaphthalene; Dekalina; Naphthalane; Naphthane; UN 1147; Decaline; NSC 406139; Cis-decahydronaphthalene
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Henry's Law data, Gas Chromatography, 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 |
---|---|---|---|---|---|
ΔcH°liquid | -6226.52 | kJ/mol | Ccb | Gollis, Belenyessy, et al., 1962 | Mixed isomers; Corresponding ΔfHºliquid = -281.05 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 265.01 | J/mol*K | N/A | McCullough, Finke, et al., 1957 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
232.08 | 298.15 | Ohnishi, Fujihara, et al., 1989 | DH |
232.20 | 298.15 | Shiohama, Ogawa, et al., 1988 | DH |
232.20 | 298.15 | Shiohama, Ogawa, et al., 1988, 2 | DH |
251.0 | 313. | Gudinowicz, Campbell, et al., 1963 | T = 313 to 423 K.; DH |
219.2 | 311. | Gollis, Belenyessy, et al., 1962, 2 | Temperatures 100, 200, 300°F.; DH |
232.00 | 298.15 | McCullough, Finke, et al., 1957 | T = 10 to 350 K.; DH |
233.51 | 298. | Seyer, 1953 | T = 293 to 343 K.; DH |
220.06 | 298.15 | Parks and Hatton, 1949 | T = 80 to 298.15 K.; DH |
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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 463.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 465. | K | N/A | Greensfelder and Voge, 1945 | Uncertainty assigned by TRC = 5. K; TRC |
Tboil | 465. | K | N/A | Larsen, Thorpe, et al., 1942 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 445. | K | N/A | Ross and Leather, 1906 | Uncertainty assigned by TRC = 10. K; TRC |
Tboil | 461. | K | N/A | Leroux, 1904 | Uncertainty assigned by TRC = 6. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 149. | K | N/A | Herz and Schuftan, 1922 | Uncertainty assigned by TRC = 2.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 645. | K | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 20.80 | bar | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 1.5199 bar; TRC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
14.414 | 242.78 | McCullough, Finke, et al., 1957 | DH |
2.209 | 230.1 | Parks and Hatton, 1949 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
59.37 | 242.78 | McCullough, Finke, et al., 1957 | DH |
9.6 | 230.1 | Parks and Hatton, 1949 | DH |
Henry's Law 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: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference |
---|---|---|---|
0.0072 | 4100. | X | N/A |
Gas Chromatography
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-54 | 1042. | Rembold, Wallner, et al., 1989 | 30. m/0.25 mm/0.25 μm, He, 0. C @ 12. min, 12. K/min; Tend: 250. C |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | PONA | 1054. | Vendeuvre, Bertoncini, et al., 2005 | 50. m/0.2 mm/0.5 μm, 2. K/min; Tstart: 50. C |
Capillary | PONA | 1066. | Vendeuvre, Bertoncini, et al., 2005 | 50. m/0.2 mm/0.5 μm, 5. K/min; Tstart: 50. C |
Capillary | CP Sil 8 CB | 1063. | Oruna-Concha, Ames, et al., 2002 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 8. min, 4. K/min, 250. C @ 10. min |
Capillary | DB-5 | 1056. | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | BPX-5 | 1089. | Elmore, Erbahadir, et al., 1997 | 50. m/0.32 mm/0.5 μm, He; Program: 0C (5min) => 40C/min => 40C (2min) => 10C/min => 280C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane: CP-Sil 5 CB | 1055. | Bramston-Cook, 2013 | 60. m/0.25 mm/1.0 μm, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min |
Capillary | DB-1 | 1054. | Peppard, 1992 | 30. m/0.25 mm/1.0 μm, He, 3. K/min, 250. C @ 30. min; Tstart: 40. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Squalane | 1087. | Chen, 2008 | Program: not specified |
Capillary | Squalane | 1064. | Chen, 2008 | Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 1043. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5MS | 173.01 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 10. K/min; Tend: 310. C |
Capillary | DB-5 | 173.31 | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
McCullough, Finke, et al., 1957
McCullough, J.P.; Finke, H.L.; Messerly, J.F.; Kincheloe, T.C.; Waddington, G.,
The low temperature thermodynamic properties of naphthalene, 1-methylnaphthalene, 2-methylnaphthalene, 1,2,3,4-tetrahydronaphthalene, trans-decahydronaphthalene and cis-decahydronaphthalene,
J. Phys. Chem., 1957, 61, 1105-1116. [all data]
Ohnishi, Fujihara, et al., 1989
Ohnishi, K.; Fujihara, I.; Murakami, S.,
Thermodynamic properties of decalins mixed with hexane isomers at 298.15K. 1. Excess enthalpies and excess isobaric heat capacities,
Fluid Phase Equilib., 1989, 46, 59-72. [all data]
Shiohama, Ogawa, et al., 1988
Shiohama, Y.; Ogawa, H.; Murakami, S.; Fujihara, I.,
Excess molar isobaric heat capacities and isentropic compressibilities of (cis- or trans-decalin + benzene or toluene or iso-octane or n-heptane) at 298.15 K,
J. Chem. Thermodynam., 1988, 20, 1183-1189. [all data]
Shiohama, Ogawa, et al., 1988, 2
Shiohama, Y.; Ogawa, H.; Murakami, S.; Fujihara, I.,
Excess thermodynamic properties of (cis-decalin or trans-decalin + cyclohexane or methylcyclohexane or cyclooctane) at 298.15 K,
J. Chem. Thermodynam., 1988, 20, 1307-1314. [all data]
Gudinowicz, Campbell, et al., 1963
Gudinowicz, B.J.; Campbell, R.H.; Adams, J.S.,
Specific heat measurements of complex saturated hydrocarbons,
J. Chem. Eng. Data, 1963, 8, 201-214. [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.,
Evaluations of pure hydrocarbons as Jet Fuels,
J. Chem. Eng. Data, 1962, 7, 311-316. [all data]
Seyer, 1953
Seyer, W.F.,
The heat capacity of cis- and trans-decahydronaphthalene and the possible existence of a lambda-region for the cis form at 50.1-50.5,
J. Am. Chem. Soc., 1953, 75, 616-621. [all data]
Parks and Hatton, 1949
Parks, G.S.; Hatton, J.A.,
Thermal data on organic compounds. XXIV. The heat capacities, entropies and free energies of cis- and trans-decahydronaphthalene,
J. Am. Chem. Soc., 1949, 71, 2773-2775. [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]
Greensfelder and Voge, 1945
Greensfelder, B.S.; Voge, H.H.,
Catalytic Cracking of Pure Hydrodarbons. Cracking of Naphthenes,
Ind. Eng. Chem., 1945, 37, 1038-43. [all data]
Larsen, Thorpe, et al., 1942
Larsen, R.G.; Thorpe, R.E.; Armfield, F.A.,
Oxidation Characteristics of Pure Hydrocarbons,
Ind. Eng. Chem., 1942, 34, 183. [all data]
Ross and Leather, 1906
Ross, R.; Leather, J.P.,
Analyst (London), 1906, 31, 284. [all data]
Leroux, 1904
Leroux, H.,
Naphthalene tetrahydride and decahydride,
C. R. Hebd. Seances Acad. Sci., 1904, 139, 672-674. [all data]
Herz and Schuftan, 1922
Herz, W.; Schuftan, P.,
Physical-chemical investigations of tetralin and decalin.,
Z. Phys. Chem. (Leipzig), 1922, 101, 269. [all data]
Glaser and Ruland, 1957
Glaser, F.; Ruland, H.,
Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen,
Chem. Ing. Techn., 1957, 29, 772. [all data]
Rembold, Wallner, et al., 1989
Rembold, H.; Wallner, P.; Nitz, S.; Kollmannsberger, H.; Drawert, F.,
Volatile components of chickpea (Cicer arietinum L.) seed,
J. Agric. Food Chem., 1989, 37, 3, 659-662, https://doi.org/10.1021/jf00087a018
. [all data]
Vendeuvre, Bertoncini, et al., 2005
Vendeuvre, C.; Bertoncini, F.; Thiébaut, D.; Martin, M.; Hennion, M.-C.,
Evluation of a retention model in comprehensive two-dimensional gas chromatography,
J. Sep. Sci., 2005, 28, 11, 1129-1136, https://doi.org/10.1002/jssc.200401933
. [all data]
Oruna-Concha, Ames, et al., 2002
Oruna-Concha, M.J.; Ames, J.M.; Bakker, J.,
Comparison of the volatile components of eight cultivars of potato after microwave baking,
Lebensm. Wiss. Technol., 2002, 35, 1, 80-86, https://doi.org/10.1006/fstl.2001.0819
. [all data]
Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E.,
Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603
. [all data]
Elmore, Erbahadir, et al., 1997
Elmore, J.S.; Erbahadir, M.A.; Mottram, D.S.,
Comparison of dynamic headspace concentration on Tenax with solid phase microextraction for the analysis of aroma volatiles,
J. Agric. Food Chem., 1997, 45, 7, 2638-2641, https://doi.org/10.1021/jf960835m
. [all data]
Bramston-Cook, 2013
Bramston-Cook, R.,
Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [all data]
Peppard, 1992
Peppard, T.L.,
Volatile flavor constituents of Monstera deliciosa,
J. Agric. Food Chem., 1992, 40, 2, 257-262, https://doi.org/10.1021/jf00014a018
. [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]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Chen, Keeran, et al., 2002
Chen, P.H.; Keeran, W.S.; Van Ausdale, W.A.; Schindler, D.R.; Roberts, D.W.,
Application of Lee retention indices to the confirmation of tentatively identified compounds from GC/MS analysis of environmental samples, Technical paper, Analytical Services Division, Environmental ScienceEngineering, Inc, PO Box 1703, Gainesville, FL 32602, 2002, 11. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas Chromatography, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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