3-Pentanone
- Formula: C5H10O
- Molecular weight: 86.1323
- IUPAC Standard InChIKey: FDPIMTJIUBPUKL-UHFFFAOYSA-N
- CAS Registry Number: 96-22-0
- 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. - Other names: Diethyl ketone; 1,3-Dimethylacetone; DEK; Ethyl ketone; Metacetone; Methacetone; Propione; (C2H5)2CO; Ethyl propionyl; Pentan-3-one; Diethylcetone; Pentanone-3; UN 1156; Dimethylacetone; NSC 8653
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -60.6 ± 0.2 | kcal/mol | Ccb | Gerasimov and Gubareva, 1985 | The hf_gas reanalyzed by ALS; ALS |
ΔfH°gas | -61.65 ± 0.20 | kcal/mol | Ccb | Harrop, Head, et al., 1970 | ALS |
ΔfH°gas | -62.25 ± 0.39 | kcal/mol | Eqk | Buckley and Herington, 1965 | Reanalyzed by Cox and Pilcher, 1970, Original value = -61.82 kcal/mol; ALS |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
34.969 | 364.15 | Hales J.L., 1967 | Experimental data [ Vilcu R., 1975] differ substantially from data selected here. Their correctness seems to be doubtful (see [ Kabo G.J., 1995]).; GT |
36.181 | 383.15 | ||
37.469 | 403.15 | ||
38.750 | 423.15 | ||
40.320 | 448.15 | ||
41.859 | 473.15 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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 | -70.87 ± 0.20 | kcal/mol | Ccb | Harrop, Head, et al., 1970 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -742.0 ± 0.2 | kcal/mol | Ccb | Gerasimov and Gubareva, 1985 | The hf_gas reanalyzed by ALS; Corresponding ΔfHºliquid = -69.79 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -740.96 ± 0.24 | kcal/mol | Ccb | Harrop, Head, et al., 1970 | Corresponding ΔfHºliquid = -70.868 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 63.58 | cal/mol*K | N/A | Andon, Counsell, et al., 1968 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
46.94 | 298.15 | Baglay, Gurariy, et al., 1988 | T = 270 to 340 K. Unsmoothed experimental datum.; DH |
46.77 | 298.15 | Baglai, Baev, et al., 1984 | T = 273 to 334 K. Cp(liq) = -1.85557 + 0.025782T - 4.0x10-5T2 kJ/kg*K (273 to 335 K).; DH |
45.483 | 298.15 | Grolier and Benson, 1984 | DH |
45.41 | 298.15 | Saluja, Peacock, et al., 1979 | DH |
47.97 | 298.15 | Harrop, Head, et al., 1970 | DH |
45.63 | 298.15 | Andon, Counsell, et al., 1968 | T = 10 to 320 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 375. ± 1. | K | AVG | N/A | Average of 53 out of 54 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 234.15 | K | N/A | Collerson, Counsell, et al., 1965 | Uncertainty assigned by TRC = 0.02 K; TRC |
Tfus | 234.18 | K | N/A | Collerson, Counsell, et al., 1965 | Uncertainty assigned by TRC = 0.01 K; TRC |
Tfus | 233.35 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 231.2 | K | N/A | Timmermans, 1927 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 231.15 | K | N/A | Timmermans and Mattaar, 1921 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 234.16 | K | N/A | Andon, Counsell, et al., 1968, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.03 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 561.5 | K | N/A | Majer and Svoboda, 1985 | |
Tc | 561.46 | K | N/A | Ambrose, Broderick, et al., 1974 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tc | 560.9 | K | N/A | Kobe, Crawford, et al., 1955 | Uncertainty assigned by TRC = 0.56 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 36.80 | atm | N/A | Ambrose, Broderick, et al., 1974 | Uncertainty assigned by TRC = 0.099 atm; TRC |
Pc | 36.91 | atm | N/A | Kobe, Crawford, et al., 1955 | Uncertainty assigned by TRC = 0.409 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.97 | mol/l | N/A | Kobe, Crawford, et al., 1955 | Uncertainty assigned by TRC = 0.35 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 9.245 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 9.207 | kcal/mol | V | Uchytilova, Majer, et al., 1983 | ALS |
ΔvapH° | 9.20 | kcal/mol | C | Uchytilova, Majer, et al., 1983 | AC |
ΔvapH° | 9.25 ± 0.07 | kcal/mol | GCC | Saluja, Peacock, et al., 1979 | AC |
ΔvapH° | 9.23 | kcal/mol | N/A | Ambrose, Ellender, et al., 1975 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.995 | 375.2 | N/A | Majer and Svoboda, 1985 | |
8.58 ± 0.05 | 332. | N/A | Baglay, Gurariy, et al., 1988 | Based on data from 290. to 375. K.; AC |
8.75 | 344. | A | Stephenson and Malanowski, 1987 | Based on data from 329. to 426. K.; AC |
8.05 | 436. | A | Stephenson and Malanowski, 1987 | Based on data from 421. to 502. K.; AC |
7.96 | 509. | A | Stephenson and Malanowski, 1987 | Based on data from 494. to 561. K.; AC |
8.75 | 344. | A,GS,EB | Stephenson and Malanowski, 1987 | Based on data from 329. to 384. K. See also Ambrose, Ellender, et al., 1975.; AC |
8.63 ± 0.02 | 335. | C | Hales, Lees, et al., 1967 | AC |
8.34 ± 0.02 | 354. | C | Hales, Lees, et al., 1967 | AC |
8.01 ± 0.02 | 375. | C | Hales, Lees, et al., 1967 | AC |
8.82 | 303. | N/A | Rintelen, Saylor, et al., 1937 | Based on data from 283. to 323. K.; AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
298. to 375. | 13.42 | 0.2923 | 561.5 | Majer and Svoboda, 1985 |
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 |
---|---|---|---|---|---|
329.69 to 384.5 | 4.14346 | 1309.653 | -59.032 | Collerson, Counsell, et al., 1965, 2 | |
309.51 to 374.8 | 2.85971 | 716.17 | -125.978 | Dreisbach and Shrader, 1949 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.770 | 234.2 | Acree, 1991 | AC |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.02651 | 118.5 | crystaline, III | crystaline, II | Andon, Counsell, et al., 1968 | DH |
0.0023 | 180. | crystaline, II | crystaline, I | Andon, Counsell, et al., 1968 | DH |
2.7710 | 234.16 | crystaline, I | liquid | Andon, Counsell, et al., 1968 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.23 | 118.5 | crystaline, III | crystaline, II | Andon, Counsell, et al., 1968 | DH |
0.01 | 180. | crystaline, II | crystaline, I | Andon, Counsell, et al., 1968 | DH |
11.83 | 234.16 | crystaline, I | liquid | Andon, Counsell, et al., 1968 | DH |
References
Go To: Top, Gas phase thermochemistry data, 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.
Gerasimov and Gubareva, 1985
Gerasimov, P.A.; Gubareva, A.I.,
Physical chemical properties of vitamin A precursor ketones,
Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1985, 28, 106-109. [all data]
Harrop, Head, et al., 1970
Harrop, D.; Head, A.J.; Lewis, G.B.,
Thermodynamic properties of organic oxygen compounds. 22. Enthalpies of combustion of some aliphatic ketones,
J. Chem. Thermodyn., 1970, 2, 203-210. [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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Hales J.L., 1967
Hales J.L.,
Thermodynamic properties of organic oxygen compounds. Part 18. Vapor heat capacities and heats of vaporization of ethyl ketone, ethyl propyl ketone, methyl isopropyl ketone, and methyl phenyl ether,
Trans. Faraday Soc., 1967, 63, 1876-1879. [all data]
Vilcu R., 1975
Vilcu R.,
Determination of heat capacities of some alcohols and ketones in vapor phase,
Rev. Roum. Chim., 1975, 20, 603-609. [all data]
Kabo G.J., 1995
Kabo G.J.,
Thermodynamic properties, conformation, and phase transitions of cyclopentanol,
J. Chem. Thermodyn., 1995, 27, 953-967. [all data]
Andon, Counsell, et al., 1968
Andon, R.J.L.; Counsell, J.F.; Martin, J.F.,
Thermodynamic properties of organic oxygen compounds. Part XX. The low-temperature heat capacity and entropy of C4 and C5 ketones,
J. Chem. Soc. A, 1968, 1894-1897. [all data]
Baglay, Gurariy, et al., 1988
Baglay, A.K.; Gurariy, L.L.; Kuleshov, G.G.,
Physical properties of compounds used in vitamin synthesis,
J. Chem. Eng. Data, 1988, 33, 512-518. [all data]
Baglai, Baev, et al., 1984
Baglai, A.K.; Baev, A.A.; Belousov, V.P.; Beregovykh, V.V.; Grushenko, M.M.; Gurarii, L.L.; Konstantinov, S.G.; Kostyushko, Yu.L.; Kuleshov, G.G.; Pasechnik, N.I.; Petrashkevich, R.I.; Podkovyrov, A.I.; Sitnov, A.A.; Shishko, M.A.; Shulgin, I.L.,
Investigation of the physico-chemical characteristics of substances utilized in the synthesis of vitamins A and E,
Khim. Farm. Zhur., 1984, 18, 1013-1019. [all data]
Grolier and Benson, 1984
Grolier, J.-P.E.; Benson, G.C.,
Thermodynamic properties of binary mixtures containing ketones. VIII. Heat capacities and volumes of some n-alkanone + n-alkane mixtures at 298.15 K,
Can. J. Chem., 1984, 62, 949-953. [all data]
Saluja, Peacock, et al., 1979
Saluja, P.P.S.; Peacock, L.A.; Fuchs, R.,
Enthalpies of interaction of aliphatic ketones with polar and nonpolar solvents,
J. Am. Chem. Soc., 1979, 101, 1958-1962. [all data]
Collerson, Counsell, et al., 1965
Collerson, R.R.; Counsell, J.F.; Handley, R.; Martin, J.F.; Sprake, C.H.S.,
677. Thermodynamic properties of organic oxygen compounds. Part XV. Purification and vapour pressures of some ketones and ethers,
J. Chem. Soc., 1965, 3697, https://doi.org/10.1039/jr9650003697
. [all data]
Timmermans, 1952
Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]
Timmermans, 1927
Timmermans, J.,
The Melting Point of Organic Substances,
Bull. Soc. Chim. Belg., 1927, 36, 502. [all data]
Timmermans and Mattaar, 1921
Timmermans, J.; Mattaar, J.F.,
Freezing points of orgainic substances VI. New experimental determinations.,
Bull. Soc. Chim. Belg., 1921, 30, 213. [all data]
Andon, Counsell, et al., 1968, 2
Andon, R.J.L.; Counsell, J.F.; Martin, J.F.,
Thermodynamic properties of organic oxygen compounds. Part XX. The low- temperature heat capacity and entropy of C4 and C5 ketones.,
J. Chem. Soc. A, 1968, 1968, 1894-7. [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]
Ambrose, Broderick, et al., 1974
Ambrose, D.; Broderick, B.E.; Townsend, R.,
The Critical Temperatures and Pressures of Thirty Organic Compounds,
J. Appl. Chem. Biotechnol., 1974, 24, 359. [all data]
Kobe, Crawford, et al., 1955
Kobe, K.A.; Crawford, H.R.; Stephenson, R.W.,
Critical Properties and Vapor Pressures of Some Ketones,
Ind. Eng. Chem., 1955, 47, 1767-72. [all data]
Uchytilova, Majer, et al., 1983
Uchytilova, V.; Majer, V.; Svoboda, V.; Hynek, V.,
Enthalpies of vaporization and cohesive enrgies for seven aliphatic ketones,
J. Chem. Thermodyn., 1983, 15, 853-858. [all data]
Ambrose, Ellender, et al., 1975
Ambrose, D.; Ellender, J.H.; Lees, E.B.; Sprake, C.H.S.; Townsend, R.,
Thermodynamic properties of organic oxygen compounds XXXVIII. Vapour pressures of some aliphatic ketones,
The Journal of Chemical Thermodynamics, 1975, 7, 5, 453-472, https://doi.org/10.1016/0021-9614(75)90275-X
. [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]
Hales, Lees, et al., 1967
Hales, J.L.; Lees, E.B.; Ruxton, D.J.,
Thermodynamic properties of organic oxygen compounds. Part 18.-Vapour heat capacities and heats of vaporization of ethyl ketone, ethyl propyl ketone, methyl isopropyl ketone, and methyl phenyl ether,
Trans. Faraday Soc., 1967, 63, 1876. [all data]
Rintelen, Saylor, et al., 1937
Rintelen, J.C.; Saylor, J.H.; Gross, P.M.,
The Densities and Vapor Pressures of Some Alkylbenzenes, Aliphatic Ketones and n-Amyl Chloride 1,
J. Am. Chem. Soc., 1937, 59, 6, 1129-1130, https://doi.org/10.1021/ja01285a050
. [all data]
Collerson, Counsell, et al., 1965, 2
Collerson, R.R.; Counsell, J.F.; Handley, R.; Martin, J.F.; Sprake, C.H.S.,
Thermodynamic Properties of Organic Oxygen Compounds. Part XV. Purification and Vapour Pressures of Some Ketones and Ethers,
J. Chem. Soc., 1965, 3697-3700, https://doi.org/10.1039/jr9650003697
. [all data]
Dreisbach and Shrader, 1949
Dreisbach, R.R.; Shrader, S.A.,
Vapor Pressure--Temperature Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 12, 2879-2880, https://doi.org/10.1021/ie50480a054
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas 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 Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy 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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