Isopropyl acetate
- Formula: C5H10O2
- Molecular weight: 102.1317
- IUPAC Standard InChIKey: JMMWKPVZQRWMSS-UHFFFAOYSA-N
- CAS Registry Number: 108-21-4
- 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, 1-methylethyl ester; Acetic acid, isopropyl ester; 2-Acetoxypropane; 2-Propyl acetate; CH3COOCH(CH3)2; Acetate d'isopropyle; Isopropile(acetato di); Isopropyl ethanoate; Isopropyl (acetate d'); Isopropylacetaat; Isopropylacetat; Isopropylester kyseliny octove; UN 1220; Isopropyl ester of acetic acid; sec-Propyl acetate; Acetic acid, 2-propyl ester; 1-Methylethyl acetate; NSC 9295
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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:
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 362. ± 3. | K | AVG | N/A | Average of 13 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 241.85 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 346.6 | K | N/A | Timmermans, 1922 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 532.0 | K | N/A | Quadri and Kudchadker, 1991 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tc | 531. | K | N/A | Ambrose, Ellender, et al., 1981 | Uncertainty assigned by TRC = 0.05 K; Visual, PRT, IPTS-68, PP.; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 32.90 | bar | N/A | Quadri and Kudchadker, 1991 | Uncertainty assigned by TRC = 0.20 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 37.0 | kJ/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 313. to 353. K.; AC |
ΔvapH° | 37.2 ± 0.2 | kJ/mol | C | Wadsö, Murto, et al., 1966 | AC |
ΔvapH° | 37.2 ± 0.2 | kJ/mol | C | Wadso, 1966 | ALS |
ΔvapH° | 33. | kJ/mol | E | Schjanberg, 1935 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
38.8 | 250. | A | Stephenson and Malanowski, 1987 | Based on data from 235. to 362. K. See also Stull, 1947.; AC |
35.6 | 323. | C | Geiseler, Quitzsch, et al., 1973 | AC |
36.3 | 288. | A | Haggerty and Weiler, 1929 | Based on data from 273. to 363. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
234.9 to 362. | 4.55172 | 1490.877 | -34.098 | Stull, 1947 | 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
L - 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 |
---|---|---|---|---|---|
IE (evaluated) | 9.99 ± 0.03 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 836.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 805.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.95 ± 0.05 | PE | Benoit, Harrison, et al., 1977 | LLK |
10.08 | PE | Sweigart and Turner, 1972 | LLK |
9.99 ± 0.03 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H5O2+ | 9.96 ± 0.05 | CH2=CHCH2 | EI | Benoit, Harrison, et al., 1977 | LLK |
C2H5O2+ | 10.4 ± 0.1 | ? | EI | Harrison and Jones, 1965 | RDSH |
C3H7+ | 11.12 ± 0.08 | ? | EI | Brion and Dunning, 1963 | RDSH |
C3H7O+ | 10.65 | CH3CO | EI | Harrison, Ivko, et al., 1966 | RDSH |
C4H7O2+ | 11.34 ± 0.07 | CH3 | EI | Brion and Dunning, 1963 | RDSH |
De-protonation reactions
C5H9O2- + =
By formula: C5H9O2- + H+ = C5H10O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1556. ± 17. | kJ/mol | G+TS | Haas, Giblin, et al., 1998 | gas phase; From transesterification equilibria; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1528. ± 17. | kJ/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: CH6N+ + C5H10O2 = (CH6N+ • C5H10O2)
Bond type: Hydrogen bonds of the type NH+-O between organics
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 126. | kJ/mol | PHPMS | Meot-Ner, 1984 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 147. | J/mol*K | PHPMS | Meot-Ner, 1984 | gas phase |
By formula: C3H9Si+ + C5H10O2 = (C3H9Si+ • C5H10O2)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 210. | kJ/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° | 132. | J/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° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
149. | 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° | 175. | kJ/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° | 140. | J/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° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
101. | 525. | PHPMS | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated |
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, 1952
Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]
Timmermans, 1922
Timmermans, J.,
Investigation of the Freezing Point of Organic Substances VII,
Bull. Soc. Chim. Belg., 1922, 31, 389. [all data]
Quadri and Kudchadker, 1991
Quadri, S.K.; Kudchadker, A.P.,
Measurement of the critical temperatures and critical pressures of some thermally stable or mildly unstable esters, ketones, and ethers,
J. Chem. Thermodyn., 1991, 23, 129-34. [all data]
Ambrose, Ellender, et al., 1981
Ambrose, D.; Ellender, J.H.; Gundry, H.A.; Lee, D.A.; Townsend, R.,
Thermodynamic properties of organic oxygen compounds. LI. The vapour pressures of some esters and fatty acids,
J. Chem. Thermodyn., 1981, 13, 795. [all data]
Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G.,
Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times,
Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3
. [all data]
Wadsö, Murto, et al., 1966
Wadsö, Ingemar; Murto, Maija-Leena; Bergson, Göran; Ehrenberg, L.; Brunvoll, J.; Bunnenberg, E.; Djerassi, Carl; Records, Ruth,
Heats of Vaporization for a Number of Organic Compounds at 25 degrees C.,
Acta Chem. Scand., 1966, 20, 544-552, https://doi.org/10.3891/acta.chem.scand.20-0544
. [all data]
Wadso, 1966
Wadso, I.,
Acta Chem. Scand., 1966, 20, 544. [all data]
Schjanberg, 1935
Schjanberg, E.,
Die Verbrennungswarmen und die Refraktionsdaten einiger chlorsubstituierter Fettsauren und Ester.,
Z. Phys. Chem. Abt. A, 1935, 172, 197-233. [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]
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]
Geiseler, Quitzsch, et al., 1973
Geiseler, G.; Quitzsch, K.; Hofmann, H.-P.; Pfestorf, R.Z.,
Z. Phys. Chem. (Leipzig), 1973, 252, 170. [all data]
Haggerty and Weiler, 1929
Haggerty, Cecil J.; Weiler, Joseph F.,
THE VAPOR PRESSURE OF ISOPROPYL ACETATE 1,
J. Am. Chem. Soc., 1929, 51, 6, 1623-1626, https://doi.org/10.1021/ja01381a001
. [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]
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]
Sweigart and Turner, 1972
Sweigart, D.A.; Turner, D.W.,
Lone pair orbitals and their interactions studied by photoelectron spectroscopy. I. Carboxylic acids and their derivatives,
J. Am. Chem. Soc., 1972, 94, 5592. [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]
Harrison and Jones, 1965
Harrison, A.G.; Jones, E.G.,
Rearrangement reactions following electron impact on ethyl and isopropyl esters,
Can. J. Chem., 1965, 43, 960. [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]
Harrison, Ivko, et al., 1966
Harrison, A.G.; Ivko, A.; Van Raalte, D.,
Energetics of formation of some oxygenated ions and the proton affinities of carbonyl compounds,
Can. J. Chem., 1966, 44, 1625. [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]
Meot-Ner, 1984
Meot-Ner, (Mautner)M.,
The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects,
J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015
. [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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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