n-Propyl acetate
- Formula: C5H10O2
- Molecular weight: 102.1317
- IUPAC Standard InChIKey: YKYONYBAUNKHLG-UHFFFAOYSA-N
- CAS Registry Number: 109-60-4
- 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: Acetic acid, propyl ester; Propyl acetate; 1-Acetoxypropane; 1-Propyl acetate; CH3COOCH2CH2CH3; Acetic acid n-propyl ester; n-Propyl ethanoate; Acetate de propyle normal; Octan propylu; Propyl ethanoate; Propylester kyseliny octove; UN 1276; Propyl ester of acetic acid; NSC 72025; n-Propanol acetate
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Phase change data
Go To: Top, Gas phase ion energetics data, Ion clustering 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 374.7 ± 0.8 | K | AVG | N/A | Average of 33 out of 37 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 178.15 | K | N/A | Timmermans and Mattaar, 1921 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 548. ± 9. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 32.91 | atm | N/A | Young, 1910 | Uncertainty assigned by TRC = 0.8000 atm; TRC |
Pc | 33.211 | atm | N/A | Young and Thomas, 1893 | Uncertainty assigned by TRC = 0.39 atm; TRC |
Pc | 34.84 | atm | N/A | Nadezhdin, 1887 | Uncertainty assigned by TRC = 0.99995 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.895 | mol/l | N/A | Young, 1910 | Uncertainty assigned by TRC = 0.05 mol/l; TRC |
ρc | 2.902 | mol/l | N/A | Young and Thomas, 1893 | Uncertainty assigned by TRC = 0.04 mol/l; TRC |
ρc | 2.84 | mol/l | N/A | Nadezhdin, 1887 | Uncertainty assigned by TRC = 0.06 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 9.2 ± 0.9 | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.107 | 374.7 | N/A | Majer and Svoboda, 1985 | |
8.84 | 348. | N/A | Fárková and Wichterle, 1993 | Based on data from 333. to 372. K.; AC |
8.32 | 389. | A | Stephenson and Malanowski, 1987 | Based on data from 374. to 542. K.; AC |
9.13 | 327. | A | Stephenson and Malanowski, 1987 | Based on data from 312. to 374. K. See also Polák and Mertl, 1965 and Dykyj, 1972.; AC |
9.11 | 327. | DTA | Meyer, Awe, et al., 1980 | Based on data from 322. to 383. K.; AC |
9.23 ± 0.02 | 313. | C | Svoboda, Uchytilová, et al., 1980 | AC |
8.44 ± 0.02 | 343. | C | Svoboda, Uchytilová, et al., 1980 | AC |
8.82 ± 0.02 | 336. | C | Svoboda, Veselý, et al., 1977 | AC |
8.70 ± 0.02 | 344. | C | Svoboda, Veselý, et al., 1977 | AC |
8.56 ± 0.02 | 351. | C | Svoboda, Veselý, et al., 1977 | AC |
8.32 ± 0.02 | 363. | C | Svoboda, Veselý, et al., 1977 | AC |
8.82 | 335. | N/A | Connett, Counsell, et al., 1976 | AC |
8.10 | 375. | N/A | Connett, Counsell, et al., 1976 | AC |
8.77 | 335. | C | Geiseler, Quitzsch, et al., 1973 | 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)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
298. to 375. | 14.39 | 0.314 | 549.4 | 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 |
---|---|---|---|---|---|
312.22 to 374.03 | 4.13815 | 1283.861 | -64.378 | Polák and Mertl, 1965 | Coefficents calculated by NIST from author's data. |
Gas phase ion energetics data
Go To: Top, Phase change data, Ion clustering data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 200.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 192.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.04 ± 0.03 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.92 | PE | Benoit and Harrison, 1977 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H5O2+ | 9.94 ± 0.05 | CH2=CHCH2 | EI | Benoit, Harrison, et al., 1977 | LLK |
C2H5O2+ | 10.48 ± 0.07 | ? | EI | Brion and Dunning, 1963 | RDSH |
C3H5O2+ | 11.29 ± 0.04 | C2H5 | EI | Brion and Dunning, 1963 | RDSH |
C3H7+ | 11.41 ± 0.04 | ? | EI | Brion and Dunning, 1963 | RDSH |
C3H7O+ | 11.64 ± 0.03 | CH3CO | EI | Brion and Dunning, 1963 | RDSH |
De-protonation reactions
C5H9O2- + =
By formula: C5H9O2- + H+ = C5H10O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 371.3 ± 4.1 | kcal/mol | G+TS | Haas, Giblin, et al., 1998 | gas phase; From transesterification equilibria; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 364.6 ± 4.0 | kcal/mol | IMRE | Haas, Giblin, et al., 1998 | gas phase; From transesterification equilibria; B |
Ion clustering data
Go To: Top, Phase change data, Gas phase ion energetics 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: C3H9Si+ + C5H10O2 = (C3H9Si+ • C5H10O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 49.4 | kcal/mol | PHPMS | Wojtyniak and Stone, 1986 | gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 31.6 | cal/mol*K | N/A | Wojtyniak and Stone, 1986 | gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
34.7 | 468. | PHPMS | Wojtyniak and Stone, 1986 | gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)H2O, Entropy change calculated or estimated |
By formula: C3H9Sn+ + C5H10O2 = (C3H9Sn+ • C5H10O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 40.2 | kcal/mol | PHPMS | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 32.8 | cal/mol*K | N/A | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
23.0 | 525. | PHPMS | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated |
By formula: NO- + C5H10O2 = (NO- • C5H10O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 42.0 | kcal/mol | ICR | Reents and Freiser, 1981 | gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978 |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Young, 1910
Young, S.,
The Internal Heat of Vaporization constants of thirty pure substances,
Sci. Proc. R. Dublin Soc., 1910, 12, 374. [all data]
Young and Thomas, 1893
Young, S.; Thomas, G.L.,
The vapour pressures, molecular volumes, and critical constants of ten of the lower esters,
J. Chem. Soc., 1893, 63, 1191. [all data]
Nadezhdin, 1887
Nadezhdin, A.,
Rep. Phys., 1887, 23, 708. [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]
Fárková and Wichterle, 1993
Fárková, J.; Wichterle, I.,
Vapour pressures of some ethyl and propyl esters of fatty acids,
Fluid Phase Equilibria, 1993, 90, 1, 143-148, https://doi.org/10.1016/0378-3812(93)85009-B
. [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]
Polák and Mertl, 1965
Polák, J.; Mertl, I.,
Saturated vapour pressure of methyl acetate, ethyl acetate, n-propyl acetate, methyl propionate, and ethyl propionate,
Collect. Czech. Chem. Commun., 1965, 30, 10, 3526-3528, https://doi.org/10.1135/cccc19653526
. [all data]
Dykyj, 1972
Dykyj, J.,
Petrochemia, 1972, 12, 1, 13. [all data]
Meyer, Awe, et al., 1980
Meyer, Edwin F.; Awe, Michael J.; Wagner, Robert E.,
Cohesive energies in polar organic liquids. 4. n-Alkyl acetates,
J. Chem. Eng. Data, 1980, 25, 4, 371-374, https://doi.org/10.1021/je60087a030
. [all data]
Svoboda, Uchytilová, et al., 1980
Svoboda, Václav; Uchytilová, Vera; Majer, Vladimír; Pick, Jirí,
Heats of vaporization of alkyl esters of formic, acetic and propionic acids,
Collect. Czech. Chem. Commun., 1980, 45, 12, 3233-3240, https://doi.org/10.1135/cccc19803233
. [all data]
Svoboda, Veselý, et al., 1977
Svoboda, V.; Veselý, F.; Holub, R.; Pick, J.,
Heats of vaporization of alkyl acetates and propionates,
Collect. Czech. Chem. Commun., 1977, 42, 3, 943-951, https://doi.org/10.1135/cccc19770943
. [all data]
Connett, Counsell, et al., 1976
Connett, J.E.; Counsell, J.F.; Lee, D.A.,
Thermodynamic properties of organic oxygen compounds XLIV. Vapour heat capacities and enthalpies of vaporization of methyl acetate, ethyl acetate, and propyl acetate,
The Journal of Chemical Thermodynamics, 1976, 8, 12, 1199-1203, https://doi.org/10.1016/0021-9614(76)90129-4
. [all data]
Geiseler, Quitzsch, et al., 1973
Geiseler, G.; Quitzsch, K.; Hofmann, H.-P.; Pfestorf, R.Z.,
Z. Phys. Chem. (Leipzig), 1973, 252, 170. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G.,
Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules,
J. Am. Chem. Soc., 1977, 99, 3980. [all data]
Benoit, Harrison, et al., 1977
Benoit, F.M.; Harrison, A.G.; Lossing, F.P.,
Hydrogen migrations in mass spectrometry III-Energetics of formation of [R'CO2H2]+ in the mass spectra of R'CO2R,
Org. Mass Spectrom., 1977, 12, 78. [all data]
Brion and Dunning, 1963
Brion, C.E.; Dunning, W.J.,
Electron impact studies of simple carboxylic esters,
J. Chem. Soc. Faraday Trans., 1963, 59, 647. [all data]
Haas, Giblin, et al., 1998
Haas, G.W.; Giblin, D.E.; Gross, M.L.,
The Mechanism and Thermodynamics of Transesterification of Acetate-Ester Enolates in the Gas Phase,
Int. J. Mass Spectrom. Ion Proc., 1998, 172, 1-2, 25, https://doi.org/10.1016/S0168-1176(97)83245-4
. [all data]
Wojtyniak and Stone, 1986
Wojtyniak, A.C.M.; Stone, A.J.,
A High-Pressure Mass Spectrometric Study of the Bonding of Trimethylsilylium to Oxygen and Aromatic Bases,
Can. J. Chem., 1986, 74, 59. [all data]
Stone and Splinter, 1984
Stone, J.A.; Splinter, D.E.,
A high-pressure mass spectrometric study of the binding of (CH3)3Sn+ to lewis bases in the gas phase,
Int. J. Mass Spectrom. Ion Processes, 1984, 59, 169. [all data]
Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S.,
Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes,
J. Am. Chem. Soc., 1981, 103, 2791. [all data]
Farid and McMahon, 1978
Farid, R.; McMahon, T.B.,
Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy,
Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0
. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, References
- Symbols used in this document:
AE Appearance energy Pc Critical pressure T Temperature Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
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