Naphthalene, 1,2,3,4-tetrahydro-

Formula: C₁₀H₁₂
Molecular weight: 132.2023
IUPAC Standard InChI: InChI=1S/C10H12/c1-2-6-10-8-4-3-7-9(10)5-1/h1-2,5-6H,3-4,7-8H2
IUPAC Standard InChIKey: CXWXQJXEFPUFDZ-UHFFFAOYSA-N
CAS Registry Number: 119-64-2
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Isotopologues:
- 1,2,3,4-Tetrahydronaphthalene-d12
Other names: Tetralin; Benzocyclohexane; Tetrahydronaphthalene; Tetraline; Tetranap; 1,2,3,4-Tetrahydronaphthalene; Naphthalene-1,2,3,4-tetrahydride; δ(5,7,9)-Naphthantriene; Bacticin; Tetralina; NSC 77451; tetralene
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	7.17	kcal/mol	N/A	Good and Lee, 1976	Value computed using Δ_fH_liquid° value of -28.6±1.0 kj/mol from Good and Lee, 1976 and Δ_vapH° value of 58.6 kj/mol from Boyd, Sanwal, et al., 1971.; DRB
Δ_fH°_gas	6.22 ± 0.47	kcal/mol	Ccb	Boyd, Sanwal, et al., 1971	Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 5.29 ± 0.81 kcal/mol; ALS

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
9.443	50.	Dorofeeva O.V., 1988	Recommended values were calculated statistically mechanically using force field approximation for polycyclic aromatic hydrocarbons to estimate the needed vibrational frequencies (see also [ Dorofeeva O.V., 1986]). These functions are reproduced in the reference book [ Frenkel M., 1994]. Values of S(298.15 K)=368.6 and Cp(298.15 K)=146.6 J/molK were calculated using molecular constants estimated by molecular mechanics [ Boyd R.H., 1971]. Discrepancies with semiempirical calculation [ Szekely, 1955] amount to 14 and 6 J/molK for S and Cp at 298.15 K. Cp(298.15 K) calculated by semiempirical calculation [ Vvedenskii A.A., 1957] agrees well with value recommended here.; GT
13.23	100.
17.98	150.
23.49	200.
32.737	273.15
36.08 ± 0.48	298.15
36.324	300.
49.391	400.
60.782	500.
70.179	600.
77.894	700.
84.288	800.
89.646	900.
94.168	1000.
98.009	1100.
101.28	1200.
104.09	1300.
106.50	1400.
108.58	1500.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, References, Notes

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
Δ_fH°_liquid	-6.83 ± 0.25	kcal/mol	Ccb	Good and Lee, 1976	ALS
Δ_fH°_liquid	-7.79 ± 0.52	kcal/mol	Ccb	Boyd, Sanwal, et al., 1971	Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -7.91 ± 0.51 kcal/mol; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1343.58 ± 0.21	kcal/mol	Ccb	Good and Lee, 1976	Corresponding Δ_fHº_liquid = -6.82 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-1342.61 ± 0.51	kcal/mol	Ccb	Boyd, Sanwal, et al., 1971	Corresponding Δ_fHº_liquid = -7.79 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-1338.1	kcal/mol	Ccb	Karo, McLaughlin, et al., 1953	Corrected from net heat of combustion; Corresponding Δ_fHº_liquid = -12.3 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-1334.1	kcal/mol	Ccb	Hock and Knauel, 1951	Corresponding Δ_fHº_liquid = -16.3 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	60.100	cal/mol*K	N/A	McCullough, Finke, et al., 1957	DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
51.969	298.15	McCullough, Finke, et al., 1957	T = 10 to 320 K.; DH

Phase change data

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

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
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

Quantity	Value	Units	Method	Reference	Comment
T_boil	480. ± 1.	K	AVG	N/A	Average of 6 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	237.3 ± 0.9	K	AVG	N/A	Average of 7 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_triple	237.3400	K	N/A	McCullough, Finke, et al., 1957, 2	Uncertainty assigned by TRC = 0.07 K; TRC
T_triple	237.3500	K	N/A	McCullough, Finke, et al., 1957, 2	Uncertainty assigned by TRC = 0.05 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_c	720. ± 1.	K	N/A	Tsonopoulos and Ambrose, 1995
T_c	721.7	K	N/A	Gude and Teja, 1994	Uncertainty assigned by TRC = 0.5 K; by the flow method; TRC
T_c	719.9	K	N/A	Teja and Anselme, 1990	Uncertainty assigned by TRC = 1. K; TRC
T_c	721.	K	N/A	Steele, Chirico, et al., 1988	Uncertainty assigned by TRC = 1.5 K; TRC
Quantity	Value	Units	Method	Reference	Comment
P_c	36.0 ± 1.	atm	N/A	Tsonopoulos and Ambrose, 1995
P_c	35.83	atm	N/A	Gude and Teja, 1994	Uncertainty assigned by TRC = 0.25 atm; by the flow method; TRC
P_c	37.01	atm	N/A	Steele, Chirico, et al., 1988	Uncertainty assigned by TRC = 0.79 atm; TRC
Quantity	Value	Units	Method	Reference	Comment
V_c	0.408	l/mol	N/A	Tsonopoulos and Ambrose, 1995
Quantity	Value	Units	Method	Reference	Comment
ρ_c	2.5 ± 0.1	mol/l	N/A	Tsonopoulos and Ambrose, 1995
ρ_c	2.45	mol/l	N/A	Teja and Anselme, 1990	Uncertainty assigned by TRC = 0.05 mol/l; TRC
ρ_c	2.27	mol/l	N/A	Steele, Chirico, et al., 1988	Uncertainty assigned by TRC = 0.11 mol/l; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	13.2 ± 0.3	kcal/mol	V	Boyd, Sanwal, et al., 1971	ALS
Δ_vapH°	14.0	kcal/mol	N/A	Boyd, Sanwal, et al., 1971	DRB

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
10.5	480.	N/A	Lee, Dempsey, et al., 1992	Based on data from 465. to 580. K.; AC
12.2	326.	A	Stephenson and Malanowski, 1987	Based on data from 311. to 481. K.; AC
9.87 ± 0.02	498.	C	Natarajan and Viswanath, 1985	AC
8.99 ± 0.02	552.	C	Natarajan and Viswanath, 1985	AC
8.53 ± 0.02	567.	C	Natarajan and Viswanath, 1985	AC
8.10 ± 0.02	585.	C	Natarajan and Viswanath, 1985	AC
7.65 ± 0.02	604.	C	Natarajan and Viswanath, 1985	AC
12.5	346.	N/A	Katayama and Harada, 1984	Based on data from 331. to 437. K.; AC
11.6	382.	N/A	Stull, 1947	Based on data from 367. to 479. K.; AC

Antoine Equation Parameters

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

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Temperature (K)	A	B	C	Reference	Comment
367.0 to 479.4	4.12100	1690.912	-70.229	Herz and Schuftan, 1922	Coefficents calculated by NIST from author's data.

Enthalpy of fusion

Δ_fusH (kcal/mol)	Temperature (K)	Reference	Comment
2.9749	237.36	McCullough, Finke, et al., 1957	DH
2.976	237.4	Domalski and Hearing, 1996	AC

Entropy of fusion

Δ_fusS (cal/mol*K)	Temperature (K)	Reference	Comment
12.53	237.36	McCullough, Finke, et al., 1957	DH

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References

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

Good and Lee, 1976
Good, W.D.; Lee, S.H., The enthalpies of formation of selected naphthalenes, diphenylmethanes, and bicyclic hydrocarbons, J. Chem. Thermodyn., 1976, 8, 643-650. [all data]

Boyd, Sanwal, et al., 1971
Boyd, R.H.; Sanwal, S.N.; Shary-Tehrany, S.; McNally, D., The thermochemistry, thermodynamic functions, and molecular structures of some cyclic hydrocarbons, J. Phys. Chem., 1971, 75, 1264-1271. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

Dorofeeva O.V., 1988
Dorofeeva O.V., Thermodynamic Properties of Polycyclic Aromatic Hydrocarbons in the Gaseous Phase. Institute for High Temperatures, USSR Academy of Sciences, Preprint No.1-238 (in Russian), Moscow, 1988. [all data]

Dorofeeva O.V., 1986
Dorofeeva O.V., On calculation of thermodynamic properties of polycyclic aromatic hydrocarbons, Thermochim. Acta, 1986, 102, 59-66. [all data]

Frenkel M., 1994
Frenkel M., Thermodynamics of Organic Compounds in the Gas State, Vol. I, II, Thermodynamics Research Center, College Station, Texas, 1994, 1994. [all data]

Boyd R.H., 1971
Boyd R.H., The thermochemistry, thermodynamic functions, and molecular structures of some cyclic hydrocarbons, J. Phys. Chem., 1971, 75, 1264-1271. [all data]

Szekely, 1955
Szekely, A., Semiempirical method for calculating thermodynamic properties. The thermodynamic data of 1,2,3,4-tetrahydronaphthalene, Acta Chim. Acad. Sci. Hung., 1955, 5, 317-339. [all data]

Vvedenskii A.A., 1957
Vvedenskii A.A., Reaction equilibrium of hydrocarbons. X. Heat capacity of naphthalene, tetrahydronaphthalene, and decahydronaphthalene, Zh. Obshch. Khim., 1957, 27, 2052-2054. [all data]

Karo, McLaughlin, et al., 1953
Karo, W.; McLaughlin, R.L.; Hipsher, H.F., Dicyclic hydrocarbons. VI. 1,2,3,4-Tetrahydronaphthalene and 1-alkyl-1,2,3,4-tetrahydronaphthalenes, J. Am. Chem. Soc., 1953, 75, 3233-3235. [all data]

Hock and Knauel, 1951
Hock, I.H.; Knauel, G., Autoxydation von kohlenwasserstoffen, XIV. Mitteil. Uber die energetische stellung organischer hydroperoxyde, Chem. Ber., 1951, 84, 1-5. [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]

McCullough, Finke, et al., 1957, 2
McCullough, J.P.; Finke, H.L.; Messerly, J.F.; Todd, S.S.; Kincheloe, T.C.; Waddington, G., The Low-Temperature Thermodynamic Properties of Naphthalene, 1-Methylnaphthalene, 2-Methylnaphthalene, 1,2,3,4-tetrahydro- naphthalene, trans-decahydronaphthalene and cis-Decahydronaphthalene, J. Phys. Chem., 1957, 61, 1105. [all data]

Tsonopoulos and Ambrose, 1995
Tsonopoulos, C.; Ambrose, D., Vapor-Liquid Critical Properties of Elements and Compounds. 3. Aromatic Hydrocarbons, J. Chem. Eng. Data, 1995, 40, 547-558. [all data]

Gude and Teja, 1994
Gude, M.T.; Teja, A.S., The Critical Properties of Several n-Alkanals, Tetralin and NMP, Experimental Results for DIPPR 1990-91 Projects on Phase Equilibria and Pure Component Properties, 1994, 1994, DIPPR Data Series No. 2, p.174-83. [all data]

Teja and Anselme, 1990
Teja, A.S.; Anselme, M.J., The critical properties of thermally stable and unstable fluids. II. 1986 results, AIChE Symp. Ser., 1990, 86, 279, 122-7. [all data]

Steele, Chirico, et al., 1988
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Smith, N.K., , Report, NIPPR-395, 1988. [all data]

Lee, Dempsey, et al., 1992
Lee, Chang Ha; Dempsey, Dennis M.; Mohamed, Rahoma S.; Holder, Gerald D., Vapor-liquid equilibria in the systems of n-decane/tetralin, n-hexadecane/tetralin, n-decane/1-methylnaphthalene, and 1-methylnaphthalene/tetralin, J. Chem. Eng. Data, 1992, 37, 2, 183-186, https://doi.org/10.1021/je00006a012 . [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]

Natarajan and Viswanath, 1985
Natarajan, Govindarajan; Viswanath, Dabir S., Enthalpy of vaporization and vapor pressure of benzene, toluene, p-xylene, and tetralin between 1 and 16 bar, J. Chem. Eng. Data, 1985, 30, 2, 137-140, https://doi.org/10.1021/je00040a001 . [all data]

Katayama and Harada, 1984
Katayama, Hirotake; Harada, Yasuhiro, Vapor pressure measurement of Tetralin at reduced pressures, J. Chem. Eng. Data, 1984, 29, 4, 373-375, https://doi.org/10.1021/je00038a002 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Herz and Schuftan, 1922
Herz, W.; Schuftan, P., Physikalisch-chemische Untersuchungen an Tetralin und Dekalin, Z. Phys. Chem. (Frankfurt/Main), 1922, 101, 269-285. [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]

Notes

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

Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
P_c	Critical pressure
S°_liquid	Entropy of liquid at standard conditions
T_boil	Boiling point
T_c	Critical temperature
T_fus	Fusion (melting) point
T_triple	Triple point temperature
V_c	Critical volume
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_fusS	Entropy of fusion
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions
ρ_c	Critical density

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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