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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Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry 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 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 |
---|---|---|---|---|---|
ΔfH°gas | -293.1 | kJ/mol | N/A | Chao and Rossini, 1965 | Value computed using ΔfHliquid° value of -342.7±0.6 kj/mol from Chao and Rossini, 1965 and ΔvapH° value of 49.6 kj/mol from Skinner and Snelson, 1960.; DRB |
ΔfH°gas | -293. ± 1.5 | kJ/mol | Ccb | Skinner and Snelson, 1960 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 355.37 | J/mol*K | N/A | Chao J., 1986 | p=1 bar. Other third-law value of entropy at 298.15 K is 357.2 J/mol*K [ Andon R.J.L., 1971]. The value of S(298.15 K)=358.5 J/mol*K was obtained from equilibrium studies [ Buckley E., 1965].; GT |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
41.87 | 50. | Thermodynamics Research Center, 1997 | p=1 bar. Calculated entropy at 298.15 K is 4.1 J/mol*K higher than the third-law value. Authors [ Chao J., 1986] believe that this is greater than the expected experimental uncertainty and reflects the approximations made in the calculated value. However, it should be noted that other experimental values of S(298.15 K), 357.2 [ Andon R.J.L., 1971] and 358.5 J/mol*K [ Buckley E., 1965], are in better agreement with calculated value. Selected S(T) and Cp(T) values agree with other statistically calculated values [62BER/MCC] within 1 J/mol*K. Values calculated by [ Rodionov P.P., 1969] are up to 9 and 11 J/mol*K lower than selected ones fo Cp(T) and S(T) values, respectively. Please also see Chao J., 1986.; GT |
59.06 | 100. | ||
74.17 | 150. | ||
86.94 | 200. | ||
105.90 | 273.15 | ||
112.74 ± 0.17 | 298.15 | ||
113.25 | 300. | ||
140.74 | 400. | ||
165.63 | 500. | ||
186.83 | 600. | ||
204.82 | 700. | ||
220.27 | 800. | ||
233.65 | 900. | ||
245.30 | 1000. | ||
255.45 | 1100. | ||
264.30 | 1200. | ||
272.03 | 1300. | ||
278.77 | 1400. | ||
284.66 | 1500. | ||
296.4 | 1750. | ||
304.9 | 2000. | ||
311.2 | 2250. | ||
315.9 | 2500. | ||
319.4 | 2750. | ||
322.1 | 3000. |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
131.71 ± 0.40 | 365.15 | Stromsoe E., 1970 | Ideal gas heat capacities are given by [ Stromsoe E., 1970] as a linear function Cp=f1*(a+bT). This expression approximates the experimental values with the average deviation of 0.67 J/mol*K. The accuracy of the experimental heat capacities [ Stromsoe E., 1970] is estimated as less than 0.3%. Please also see Berman N.S., 1962.; GT |
137.87 ± 0.67 | 380.95 | ||
136.52 ± 0.41 | 383.15 | ||
139.10 ± 0.67 | 386.25 | ||
140.85 ± 0.67 | 393.75 | ||
141.46 ± 0.42 | 401.15 | ||
143.50 ± 0.67 | 405.15 | ||
143.74 ± 0.67 | 406.15 | ||
146.32 ± 0.67 | 417.25 | ||
146.23 ± 0.44 | 419.15 | ||
150.96 ± 0.45 | 437.15 | ||
151.79 ± 0.67 | 440.75 | ||
155.64 ± 0.47 | 455.15 | ||
158.81 ± 0.67 | 470.85 | ||
169.31 ± 0.67 | 515.95 | ||
179.65 ± 0.67 | 560.35 | ||
184.89 ± 0.67 | 582.85 |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry 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 as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar
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
C4H9O- + =
By formula: C4H9O- + H+ = C4H10O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1565. ± 8.4 | kJ/mol | CIDC | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
ΔrH° | 1566. ± 8.8 | kJ/mol | G+TS | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 1565. ± 12. | kJ/mol | G+TS | Boand, Houriet, et al., 1983 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1538. ± 8.8 | kJ/mol | H-TS | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
ΔrG° | 1538. ± 8.4 | kJ/mol | IMRE | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 1538. ± 11. | kJ/mol | CIDC | Boand, Houriet, et al., 1983 | gas phase; value altered from reference due to change in acidity scale; B |
By formula: H2 + C4H8O = C4H10O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -54.18 | kJ/mol | Eqk | Buckley and Herington, 1965 | gas phase; ALS |
ΔrH° | -54.3 ± 0.4 | kJ/mol | Chyd | Dolliver, Gresham, et al., 1938 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -55.2 ± 0.4 kJ/mol; At 355 °K; ALS |
By formula: C4H10O = H2 + C4H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 54.22 | kJ/mol | Eqk | Cubberley and Mueller, 1946 | gas phase; ALS |
ΔrH° | 57.170 | kJ/mol | Eqk | Kolb and Burwell, 1945 | gas phase; ALS |
By formula: C4H8 + C4H10O = C8H18O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -37.7 ± 2.4 | kJ/mol | Eqk | Sharonov, Mishentseva, et al., 1991 | liquid phase; ALS |
By formula: C2H2O + C4H10O = C6H12O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -144.5 | kJ/mol | Cm | Rice and Greenberg, 1934 | liquid phase; ALS |
By formula: Na+ + C4H10O = (Na+ • C4H10O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 117. ± 5.0 | kJ/mol | CIDT | Rodgers and Armentrout, 1999 | RCD |
By formula: Li+ + C4H10O = (Li+ • C4H10O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 174. ± 9.2 | kJ/mol | CIDT | Rodgers and Armentrout, 2000 | RCD |
Henry's Law data
Go To: Top, Gas phase thermochemistry data, Reaction 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 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 |
---|---|---|---|
110. | 7300. | M | N/A |
97. | M | Butler, Ramchandani, et al., 1935 | |
97. | V | Butler, Ramchandani, et al., 1935 |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Henry's Law 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]
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]
Chao J., 1986
Chao J.,
Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties,
J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]
Andon R.J.L., 1971
Andon R.J.L.,
Thermodynamic properties of organic oxygen compounds. Part XXVII. (+/-)-Butan-2-ol and (+)-butan-2-ol,
J. Chem. Soc. A, 1971, 661-664. [all data]
Buckley E., 1965
Buckley E.,
Equilibria in some secondary alcohol + hydrogen + ketone systems,
Trans. Faraday Soc., 1965, 61, 1618-1625. [all data]
Thermodynamics Research Center, 1997
Thermodynamics Research Center,
Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]
Rodionov P.P., 1969
Rodionov P.P.,
Thermodynamic functions of 2-butanol (d,l),
Izv. Vyssh. Ucheb. Zaved., Khim. Khim. Tekhnol., 1969, 12, 1214-1218. [all data]
Stromsoe E., 1970
Stromsoe E.,
Heat capacity of alcohol vapors at atmospheric pressure,
J. Chem. Eng. Data, 1970, 15, 286-290. [all data]
Berman N.S., 1962
Berman N.S.,
Thermodynamic properties of 2-butanol,
J. Phys. Chem., 1962, 66, 1444-1448. [all data]
Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G.,
The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols,
Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W
. [all data]
Taft, 1987
Taft, R.W.,
The Nature and Analysis of Substitutent Electronic Effects,
Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]
Boand, Houriet, et al., 1983
Boand, G.; Houriet, R.; Baumann, T.,
The gas phase acidity of aliphatic alcohols,
J. Am. Chem. Soc., 1983, 105, 2203. [all data]
Buckley and Herington, 1965
Buckley, E.; Herington, E.F.G.,
Equilibria in some secondary alcohol + hydrogen + ketone systems,
Trans. Faraday Soc., 1965, 61, 1618-1625. [all data]
Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E.,
Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds,
J. Am. Chem. Soc., 1938, 60, 440-450. [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]
Cubberley and Mueller, 1946
Cubberley, A.H.; Mueller, M.B.,
Equilibrium studies on the dehydrogenation of primary and secondary alcohols. I. 2-Butanol, 2-octanol, cyclopentanol and benzyl alcohol,
J. Am. Chem. Soc., 1946, 68, 1149-1151. [all data]
Kolb and Burwell, 1945
Kolb, H.J.; Burwell, R.L., Jr.,
Equilibrium in the dehydrogenation of secondary propyl and butyl alcohols,
J. Am. Chem. Soc., 1945, 67, 1084-1088. [all data]
Sharonov, Mishentseva, et al., 1991
Sharonov, K.G.; Mishentseva, Y.B.; Rozhnov, A.M.; Miroshnichenko, E.A.; Korchatova, L.I.,
Molar enthalpies of formation and vaporizqation of t-butoxybutanes and thermodynamics of their synthesis from a butanol and 2-methylpropene I. Equilibria of synthesis reactions of t-butoxybutanes in the liquid phase,
J. Chem. Thermodyn., 1991, 23, 141-145. [all data]
Rice and Greenberg, 1934
Rice, F.O.; Greenberg, J.,
Ketene. III. Heat of formation and heat of reaction with alcohols,
J. Am. Chem. Soc., 1934, 38, 2268-2270. [all data]
Rodgers and Armentrout, 1999
Rodgers, M.T.; Armentrout, P.B.,
Absolute Binding Energies of Sodium Ions to Short-Chain Alcohols, CnH2n+2O, n=1-4, Determined by Threshold Collision-Induced Dissociation Experiments and Ab Initio Theory, 1999, 4955. [all data]
Rodgers and Armentrout, 2000
Rodgers, M.T.; Armentrout, P.B.,
Noncovalent Metal-Ligand Bond Energies as Studied by Threshold Collision-Induced Dissociation,
Mass Spectrom. Rev., 2000, 19, 4, 215, https://doi.org/10.1002/1098-2787(200007)19:4<215::AID-MAS2>3.0.CO;2-X
. [all data]
Butler, Ramchandani, et al., 1935
Butler, J.A.V.; Ramchandani, C.N.; Thomson, D.W.,
The Solubility of Non-Electrolytes. Part 1. The Free Energy of Hydration of Some Alphatic Alcohols,
J. Chem. Soc., 1935, 280-285, https://doi.org/10.1039/jr9350000280
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas S°gas Entropy of gas at standard conditions d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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