2-Butanol
- Formula: C4H10O
- Molecular weight: 74.1216
- IUPAC Standard InChIKey: BTANRVKWQNVYAZ-UHFFFAOYSA-N
- CAS Registry Number: 78-92-2
- 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. - Species with the same structure:
- Stereoisomers:
- Other names: sec-Butyl Alcohol; sec-Butanol; CCS 301; Ethyl methyl carbinol; Methyl ethyl carbinol; 1-Methyl-1-propanol; 1-Methylpropyl alcohol; 2-Hydroxybutane; sec-C4H9OH; Butane, 2-hydroxy-; Butanol-2; Butan-2-ol; 2-Butyl alcohol; s-Butyl alcohol; Butylene hydrate; DL-sec-Butanol; DL-2-Butanol; Alcool butylique secondaire; Butanol secondaire; s-Butanol; 1-Methyl propanol; n-Butan-2-ol; NSC 25499
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Condensed phase thermochemistry data
Go To: Top, Phase change 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -81.90 ± 0.14 | kcal/mol | Ccb | Chao and Rossini, 1965 | see Rossini, 1934; ALS |
ΔfH°liquid | -81.88 ± 0.22 | kcal/mol | Ccb | Skinner and Snelson, 1960 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -635.89 ± 0.13 | kcal/mol | Ccb | Chao and Rossini, 1965 | see Rossini, 1934; Corresponding ΔfHºliquid = -81.89 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -635.91 ± 0.22 | kcal/mol | Ccb | Skinner and Snelson, 1960 | Corresponding ΔfHºliquid = -81.87 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 50.93 | cal/mol*K | N/A | Andon, Connett, et al., 1971 | DH |
S°liquid | 51.31 | cal/mol*K | N/A | Andon, Connett, et al., 1971 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
47.11 | 298.15 | N/A | DH |
47.330 | 298.15 | Okano, Ogawa, et al., 1988 | DH |
47.005 | 298.15 | Piekarski and Somsen, 1988 | DH |
47.61 | 298. | Conti, Gianni, et al., 1976 | DH |
47.18 | 298.15 | Andon, Connett, et al., 1971 | T = 11 to 350 K.; DH |
47.04 | 298.15 | Andon, Connett, et al., 1971 | T = 11 to 350 K.; DH |
44.19 | 281.7 | Parks, Thomas, et al., 1936 | T = 103 to 282 K. Glass at lower temperature. Unsmoothed experimental datum.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry 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
AC - William E. Acree, Jr., James S. Chickos
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 |
---|---|---|---|---|---|
Tboil | 372. ± 1. | K | AVG | N/A | Average of 69 out of 71 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 184.73 | K | N/A | Wilhoit, Chao, et al., 1985 | Uncertainty assigned by TRC = 0.1 K; TRC |
Ttriple | 184.70 | K | N/A | Andon, Connett, et al., 1971, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 536. ± 1. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 41.4 ± 0.2 | atm | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.269 | l/mol | N/A | Gude and Teja, 1995 | |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.72 ± 0.02 | mol/l | N/A | Gude and Teja, 1995 | |
ρc | 3.72 | mol/l | N/A | Teja, Lee, et al., 1989 | TRC |
ρc | 3.717 | mol/l | N/A | Ambrose and Townsend, 1963 | TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 12. ± 1. | kcal/mol | AVG | N/A | Average of 9 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
9.739 | 372.7 | N/A | Majer and Svoboda, 1985 | |
11.7 | 330. | EB | Gierycz, Kosowski, et al., 2009 | Based on data from 315. to 371. K.; AC |
11.0 | 335. | N/A | Martínez, Lladosa, et al., 2009 | Based on data from 320. to 379. K.; AC |
11.4 | 321. | N/A | Dejoz, Cruz Burguet, et al., 1995 | Based on data from 306. to 373. K.; AC |
11.8 | 318. | A | Stephenson and Malanowski, 1987 | Based on data from 303. to 403. K.; AC |
10.3 | 370. | A | Stephenson and Malanowski, 1987 | Based on data from 359. to 381. K.; AC |
11.4 | 387. | A | Stephenson and Malanowski, 1987 | Based on data from 372. to 524. K.; AC |
13.7 | 225. | A | Stephenson and Malanowski, 1987 | Based on data from 210. to 303. K.; AC |
10.3 | 369. | A | Stephenson and Malanowski, 1987 | Based on data from 359. to 380. K.; AC |
10. | 383. | A | Stephenson and Malanowski, 1987 | Based on data from 368. to 404. K.; AC |
9.46 | 410. | A | Stephenson and Malanowski, 1987 | Based on data from 395. to 485. K.; AC |
8.4 | 491. | A | Stephenson and Malanowski, 1987 | Based on data from 476. to 536. K.; AC |
10.7 | 355. | EB | Stephenson and Malanowski, 1987 | Based on data from 340. to 379. K. See also Berman and McKetta, 1962 and Ambrose, Counsell, et al., 1970.; AC |
11.4 | 322. | N/A | Sachek, Peshchenko, et al., 1982 | Based on data from 307. to 373. K.; AC |
12.7 | 308. | N/A | Di Cave, Chianese, et al., 1978 | Based on data from 293. to 380. K.; AC |
10.5 | 334. | N/A | Brazhnikov, Andreevskii, et al., 1975 | Based on data from 319. to 372. K.; AC |
12.0 | 295. | N/A | Cabani, Conti, et al., 1975 | Based on data from 280. to 314. K.; AC |
11.5 | 313. | N/A | Wilhoit and Zwolinski, 1973 | Based on data from 298. to 393. K.; AC |
11.1 | 338. | N/A | Brown, Fock, et al., 1969 | Based on data from 323. to 373. K. See also Boublik, Fried, et al., 1984.; AC |
10.5 | 360. | EB | Biddiscombe, Collerson, et al., 1963 | Based on data from 345. to 381. K.; AC |
10.8 ± 0.02 | 340. | C | Berman and McKetta, 1962 | AC |
10.3 ± 0.02 | 355. | C | Berman and McKetta, 1962 | AC |
10.0 ± 0.02 | 365. | C | Berman and McKetta, 1962 | AC |
9.75 ± 0.02 | 372. | C | Berman and McKetta, 1962 | AC |
Enthalpy of vaporization
ΔvapH = A exp(-αTr)
(1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | 298. to 372. |
---|---|
A (kcal/mol) | 12.6 |
α | -1.462 |
β | 1.0701 |
Tc (K) | 536. |
Reference | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
422.11 to 535.9 | 4.19256 | 1094.254 | -111.603 | Ambrose and Townsend, 1963, 2 | Coefficents calculated by NIST from author's data. |
345.54 to 380.30 | 4.32372 | 1158.672 | -104.683 | Biddiscombe, Collerson, et al., 1963, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.434 | 177.38 | Andon, Connett, et al., 1971 | DH |
1.427 | 184.70 | Andon, Connett, et al., 1971 | DH |
1.43 | 184.7 | Andon, Connett, et al., 1971, 3 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.086 | 177.38 | Andon, Connett, et al., 1971 | DH |
7.725 | 184.70 | Andon, Connett, et al., 1971 | DH |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Chao and Rossini, 1965
Chao, J.; Rossini, F.D.,
Heats of combustion, formation, and isomerization of nineteen alkanols,
J. Chem. Eng. Data, 1965, 10, 374-379. [all data]
Rossini, 1934
Rossini, F.D.,
Heats of combustion and of formation of the normal aliphatic alcohols in the gaseous and liquid states, and the energies of their atomic linkages,
J. Res. NBS, 1934, 13, 189-197. [all data]
Skinner and Snelson, 1960
Skinner, H.A.; Snelson, A.,
The heats of combustion of the four isomeric butyl alcohols,
Trans. Faraday Soc., 1960, 56, 1776-1783. [all data]
Andon, Connett, et al., 1971
Andon, R.J.; Connett, J.E.; Counsell, J.F.; Lees, E.B.; Martin, J.F.,
Thermodynamic properties of organic oxygen compounds. Part XXVII. (±)-Butan-2-ol and (+)-Butan-2-ol, 1971, J. [all data]
Okano, Ogawa, et al., 1988
Okano, T.; Ogawa, H.; Murakami, S.,
Molar excess volumes, isentropic compressions, and isobaric heat capacities of methanol-isomeric butanol systems at 298.15 K,
Can. J. Chem., 1988, 66, 713-717. [all data]
Piekarski and Somsen, 1988
Piekarski, H.; Somsen, G.,
Heat capacities and volumes of mixtures of N,N-dimethylformamide with isobutanol, sec-butanol and t-pentanol, J. Chem. Soc.,
Faraday Trans. 1, 1988, 84(2), 529-537. [all data]
Conti, Gianni, et al., 1976
Conti, G.; Gianni, P.; Matteoli, E.; Mengheri, M.,
Capacita termiche molari di alcuni composti organici mono- e bifunzionali nel liquido puro e in soluzione acquosa a 25C,
Chim. Ind. (Milan), 1976, 58, 225. [all data]
Parks, Thomas, et al., 1936
Parks, G.S.; Thomas, S.B.; Light, D.W.,
XII. Some new heat capacity data for organic glasses. The entropy and free energy of DL-lactic acid,
J. Chem. Phys., 1936, 4, 64-69. [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]
Andon, Connett, et al., 1971, 2
Andon, R.J.L.; Connett, J.E.; Counsell, J.F.; Lees, E.B.; Martin, J.F.,
Thermodynamic properties of organic oxygen compounds: xxvii racemate of - butan-2-ol and (+)-butan-2-ol,
J. Chem. Soc. A, 1971, 1971, 661-4. [all data]
Gude and Teja, 1995
Gude, M.; Teja, A.S.,
Vapor-Liquid Critical Properties of Elements and Compounds. 4. Aliphatic Alkanols,
J. Chem. Eng. Data, 1995, 40, 1025-1036. [all data]
Teja, Lee, et al., 1989
Teja, A.S.; Lee, R.J.; Rosenthal, D.J.; Anselme, M.J.,
Correlation of the Critical Properties of Alkanes and Alkanols
in 5th IUPAC Conference on Alkanes and AlkanolsGradisca, 1989. [all data]
Ambrose and Townsend, 1963
Ambrose, D.; Townsend, R.,
Thermodynamic Properties of Organic Oxygen Compounds IX. The Critical Properties and Vapor Pressures Above Five Atmospheres of Six Aliphatic Alcohols,
J. Chem. Soc., 1963, 54, 3614-25. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Gierycz, Kosowski, et al., 2009
Gierycz, Pawel; Kosowski, Andrzej; Swietlik, Ryszard,
Vapor-Liquid Equilibria in Binary Systems Formed by Cyclohexane with Alcohols,
J. Chem. Eng. Data, 2009, 54, 11, 2996-3001, https://doi.org/10.1021/je900050z
. [all data]
Martínez, Lladosa, et al., 2009
Martínez, Nelson F.; Lladosa, Estela; Burguet, MªCruz; Montón, Juan B.; Yazimon, Marlen,
Isobaric vapour--liquid equilibria for the binary systems 4-methyl-2-pentanone+1-butanol and+2-butanol at 20 and 101.3kPa,
Fluid Phase Equilibria, 2009, 277, 1, 49-54, https://doi.org/10.1016/j.fluid.2008.11.012
. [all data]
Dejoz, Cruz Burguet, et al., 1995
Dejoz, Ana; Cruz Burguet, M.; Munoz, Rosa; Sanchotello, Margarita,
Isobaric Vapor-Liquid Equilibria of Tetrachloroethylene with 1-Butanol and 2-Butanol at 6 and 20 kPa,
J. Chem. Eng. Data, 1995, 40, 1, 290-292, https://doi.org/10.1021/je00017a064
. [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
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Berman and McKetta, 1962
Berman, Neil S.; McKetta, John J.,
THE THERMODYNAMIC PROPERTIES OF 2-BUTANOL,
J. Phys. Chem., 1962, 66, 8, 1444-1448, https://doi.org/10.1021/j100814a016
. [all data]
Ambrose, Counsell, et al., 1970
Ambrose, D.; Counsell, J.F.; Davenport, A.J.,
The use of Chebyshev polynomials for the representation of vapour pressures between the triple point and the critical point,
The Journal of Chemical Thermodynamics, 1970, 2, 2, 283-294, https://doi.org/10.1016/0021-9614(70)90093-5
. [all data]
Sachek, Peshchenko, et al., 1982
Sachek, A.I.; Peshchenko, A.D.; Markovnik, V.S.; Ral'ko, O.V.; Andreevskii, D.N.; Leont'eva, A.A.,
Termodin. Org. Soedin., 1982, 94. [all data]
Di Cave, Chianese, et al., 1978
Di Cave, Sergio; Chianese, Angelo; Prantera, Antonio,
Vapor-liquid equilibrium of the system methylethylketone-sec-butyl alcohol,
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Brazhnikov, Andreevskii, et al., 1975
Brazhnikov, M.M.; Andreevskii, D.N.; Sachek, A.I.; Peshchenko, A.D.,
Zh. Prikl. Khim. (Leningrad), 1975, 48, 10, 2181. [all data]
Cabani, Conti, et al., 1975
Cabani, Sergio; Conti, G.; Mollica, V.; Lepori, L.,
Thermodynamic study of dilute aqueous solutions of organic compounds. Part 4.---Cyclic and straight chain secondary alcohols,
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Wilhoit and Zwolinski, 1973
Wilhoit, R.C.; Zwolinski, B.J.,
Physical and thermodynamic properties of aliphatic alcohols,
J. Phys. Chem. Ref. Data Suppl., 1973, 1, 2, 1. [all data]
Brown, Fock, et al., 1969
Brown, I.; Fock, W.; Smith, F.,
The thermodynamic properties of solutions of normal and branched alcohols in benzene and n-hexane,
The Journal of Chemical Thermodynamics, 1969, 1, 3, 273-291, https://doi.org/10.1016/0021-9614(69)90047-0
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Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Biddiscombe, Collerson, et al., 1963
Biddiscombe, D.P.; Collerson, R.R.; Handley, R.; Herington, E.F.G.; Martin, J.F.; Sprake, C.H.S.,
364. Thermodynamic properties of organic oxygen compounds. Part VIII. Purification and vapour pressures of the propyl and butyl alcohols,
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Ambrose and Townsend, 1963, 2
Ambrose, D.; Townsend, R.,
Thermodynamic Properties of Organic Oxygen Compounds. Part 9. The Critical Properties and Vapour Pressures, above Five Atmospheres, of Six Aliphatic Alcohols,
J. Chem. Soc., 1963, 3614-3625, https://doi.org/10.1039/jr9630003614
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Biddiscombe, Collerson, et al., 1963, 2
Biddiscombe, D.P.; Collerson, R.R.; Handley, R.; Herington, E.F.G.; Martin, J.F.; Sprake, C.H.S.,
Thermodynamic Properties of Organic Oxygen Compounds. Part 8. Purification and Vapor Pressures of the Propyl and Butyl Alcohols,
J. Chem. Soc., 1963, 1954-1957, https://doi.org/10.1039/jr9630001954
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Andon, Connett, et al., 1971, 3
Andon, R.J.L.; Connett, J.E.; Counsell, J.F.; Lees, E.B.; Martin, J.F.,
Thermodynamic properties of organic oxygen compounds. Part XXVII. («65533»)-Butan-2-ol and (+)-butan-2-ol,
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. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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 Ttriple Triple point temperature Vc Critical volume ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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