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Formic acid, butyl ester

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Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference
47.861298.15Jimenez, Romani, et al., 1986

Phase change data

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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
Tboil379.7 ± 0.7KAVGN/AAverage of 11 out of 12 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus183.15KN/ATimmermans, 1927Uncertainty assigned by TRC = 1.5 K; TRC
Tfus183.2KN/ATimmermans, 1922Uncertainty assigned by TRC = 0.4 K; TRC
Quantity Value Units Method Reference Comment
Tc565.2KN/AMajer and Svoboda, 1985 
Quantity Value Units Method Reference Comment
Deltavap9.837kcal/molN/AMajer and Svoboda, 1985 
Deltavap9.58kcal/molEBChylinski, Fras, et al., 2004Based on data from 313. - 359. K.; AC
Deltavap9.87 ± 0.02kcal/molCSvoboda, Uchytilová, et al., 1980AC
Deltavap8.86 ± 0.01kcal/molVMathews, 1926ALS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
8.743379.3N/AMajer and Svoboda, 1985 
9.06310.AStephenson and Malanowski, 1987Based on data from 295. - 380. K.; AC
9.58 ± 0.02313.CSvoboda, Uchytilová, et al., 1980AC
9.32 ± 0.02328.CSvoboda, Uchytilová, et al., 1980AC
9.25 ± 0.02346.CCihlár, Hynek, et al., 1976AC
9.11 ± 0.02355.CCihlár, Hynek, et al., 1976AC
8.91 ± 0.02363.CCihlár, Hynek, et al., 1976AC

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) beta Tc (K) Reference Comment
298. - 363.13.200.231565.2Majer 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
302.3 - 385.64.222011347.33-59.956Nelson, 1928Coefficents calculated by NIST from author's data.

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

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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. 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

CH6N+ + Formic acid, butyl ester = (CH6N+ bullet Formic acid, butyl ester)

By formula: CH6N+ + C5H10O2 = (CH6N+ bullet C5H10O2)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity Value Units Method Reference Comment
Deltar24.5kcal/molPHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated
Quantity Value Units Method Reference Comment
Deltar26.cal/mol*KN/AMeot-Ner, 1984gas phase; Entropy change calculated or estimated

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
12.5461.PHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated

Gas phase ion energetics data

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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:
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)10.52 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)192.6kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity185.kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
10.52 ± 0.05PEBenoit, Harrison, et al., 1977LLK
10.54PESweigart and Turner, 1972LLK
10.50 ± 0.02PIWatanabe, Nakayama, et al., 1962RDSH
10.52PEBenoit and Harrison, 1977Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CHO+11.47 ± 0.11?EIBrion and Dunning, 1963RDSH
C3H7+12.24 ± 0.12?EIBrion and Dunning, 1963RDSH

Ion clustering data

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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

CH6N+ + Formic acid, butyl ester = (CH6N+ bullet Formic acid, butyl ester)

By formula: CH6N+ + C5H10O2 = (CH6N+ bullet C5H10O2)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity Value Units Method Reference Comment
Deltar24.5kcal/molPHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated
Quantity Value Units Method Reference Comment
Deltar26.cal/mol*KN/AMeot-Ner, 1984gas phase; Entropy change calculated or estimated

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
12.5461.PHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated

IR Spectrum

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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IR spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1990.
NIST MS number 118902

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedApiezon L160.684.Bogoslovsky, Anvaer, et al., 1978Celite 545
PackedApiezon L130.680.Bogoslovsky, Anvaer, et al., 1978 
PackedSE-30150.707.Ashes and Haken, 1974Celaton (62-72 mesh); Column length: 3.7 m
PackedSE-30150.703.Germaine and Haken, 1969Celite 560; Column length: 3.7 m
PackedApiezon L130.680.Wehrli and Kováts, 1959Celite; Column length: 2.25 m

Kovats' RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillarySE-30707.Chretien and Dubois, 1978Program: not specified

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryDB-5737.Isidorov, Zenkevich, et al., 2001He, 3. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tstart: 50. C; Tend: 250. C

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryHP-5737.Isidorov, Krajewska, et al., 200130. m/0.25 mm/0.25 «mu»m, He; Program: 50C => 6C/min => 100C => 4C/min => 280C

Van Den Dool and Kratz RI, polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryFFAP1010.Yasuhara, 198750. m/0.25 mm/0.25 «mu»m, He; Program: 20C (5min) => 2C/min => 70C => 4C/min => 210C

Normal alkane RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryPolydimethyl siloxane105.706.Tello, Lebron-Aguilar, et al., 2009 
CapillaryPolydimethyl siloxane75.707.Tello, Lebron-Aguilar, et al., 2009 
CapillaryPolydimethyl siloxane90.706.Tello, Lebron-Aguilar, et al., 2009 

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryMethyl Silicone707.Du and Feng, 2008Program: not specified
CapillaryHP-5724.Zhao, Li, et al., 200830. m/0.25 mm/0.25 «mu»m; Program: 40 0C (2 min) 5 0C/min -> 80 0C 7 oC/min -> 160 0C 9 0C/min -> 200 0C 20 0C/min -> 280 0C (10 min)
CapillaryHP-5737.Zhao, Li, et al., 200830. m/0.25 mm/0.25 «mu»m; Program: not specified
CapillarySE-30696.Vinogradov, 2004Program: not specified
CapillarySPB-1708.Flanagan, Streete, et al., 199760. m/0.53 mm/5. «mu»m, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C
CapillaryDB-1711.Ciccioli, Cecinato, et al., 199460. m/0.32 mm/0.25 «mu»m; Program: not specified
CapillaryDB-1711.Ciccioli, Brancaleoni, et al., 199360. m/0.32 mm/0.25 «mu»m; Program: 3 min at 5 C; 5 - 50 C at 3 deg/min; 50 - 220 C at 5 deg/min
CapillarySPB-1708.Strete, Ruprah, et al., 199260. m/0.53 mm/5.0 «mu»m, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C
CapillarySPB-1701.Strete, Ruprah, et al., 199260. m/0.53 mm/5.0 «mu»m, Helium; Program: not specified
CapillaryOV-101696.Shibamoto, 1987Program: not specified
CapillaryOV-1701.Ramsey and Flanagan, 1982Program: not specified

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryCarbowax 20M996.Vinogradov, 2004Program: not specified
CapillaryDB-Wax1033.Peng, Yang, et al., 1991Program: not specified
CapillaryCarbowax 20M996.Shibamoto, 1987Program: not specified
CapillaryCarbowax 20M1020.Ramsey and Flanagan, 1982Program: not specified

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Jimenez, Romani, et al., 1986
Jimenez, E.; Romani, L.; Paz Andrade, M.I.; Roux-Desgranges, G.; Grolier, J.-P.E., Molar excess heat capacities and volumes for mixtures of alkanoates with cyclohexane at 25°C, J. Solution Chem., 1986, 15(11), 879-890. [all data]

Timmermans, 1927
Timmermans, J., The Melting Point of Organic Substances, Bull. Soc. Chim. Belg., 1927, 36, 502. [all data]

Timmermans, 1922
Timmermans, J., Investigation of the Freezing Point of Organic Substances VII, Bull. Soc. Chim. Belg., 1922, 31, 389. [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]

Chylinski, Fras, et al., 2004
Chylinski, Krzysztof; Fras, Zbigniew; Malanowski, Stanislaw K., Vapor-Liquid Equilibrium for Phenol + «alpha»-Methyl Benzyl Alcohol and 2-Ethoxyethanol + n -Butyl Formate «8224», J. Chem. Eng. Data, 2004, 49, 1, 2-6, https://doi.org/10.1021/je025566c . [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]

Mathews, 1926
Mathews, J.H., The accurate measurement of heats of vaporization of liquids, J. Am. Chem. Soc., 1926, 48, 562-576. [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]

Cihlár, Hynek, et al., 1976
Cihlár, J.; Hynek, V.; Svoboda, V.; Holub, R., Heats of vaporization of alkyl esters of formic acid, Collect. Czech. Chem. Commun., 1976, 41, 1, 1-6, https://doi.org/10.1135/cccc19760001 . [all data]

Nelson, 1928
Nelson, O.A., Vapor Pressures of Fumigants: II---Methyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, Secondary Butyl and Isobutyl Formates 1, Ind. Eng. Chem., 1928, 20, 12, 1382-1384, https://doi.org/10.1021/ie50228a035 . [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]

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]

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]

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]

Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

Ashes and Haken, 1974
Ashes, J.R.; Haken, J.K., Gas chromatography of homologous esters. VI. Structure-retention increments of aliphatic esters, J. Chromatogr., 1974, 101, 1, 103-123, https://doi.org/10.1016/S0021-9673(01)94737-5 . [all data]

Germaine and Haken, 1969
Germaine, R.W.; Haken, J.K., Gas chromatography of homologous esters. Part 1. Simple aliphatic esters, J. Chromatogr., 1969, 43, 33-42, https://doi.org/10.1016/S0021-9673(00)99162-3 . [all data]

Wehrli and Kováts, 1959
Wehrli, A.; Kováts, E., Gas-chromatographische Charakterisierung ogranischer Verbindungen. Teil 3: Berechnung der Retentionsindices aliphatischer, alicyclischer und aromatischer Verbindungen, Helv. Chim. Acta, 1959, 7, 7, 2709-2736, https://doi.org/10.1002/hlca.19590420745 . [all data]

Chretien and Dubois, 1978
Chretien, J.R.; Dubois, J-E., Topological Analysis: A Technique for the Physico-Chemical Exploitation of Retention Data in Gas-Liquid Chromatography, J. Chromatogr., 1978, 158, 43-56, https://doi.org/10.1016/S0021-9673(00)89954-9 . [all data]

Isidorov, Zenkevich, et al., 2001
Isidorov, V.A.; Zenkevich, I.G.; Krajewska, U.; Dubis, E.N.; Jaroszynska, J.; Bal, K., Gas chromatographic analysis of essential oils with preliminary partition of components, Phytochem. Anal., 2001, 12, 2, 87-90, https://doi.org/10.1002/pca.564 . [all data]

Isidorov, Krajewska, et al., 2001
Isidorov, V.A.; Krajewska, U.; Dubis, E.N.; Jdanova, M.A., Partition coefficients of alkyl aromatic hydrocarbons and esters in a hexane-acetonitrile system, J. Chromatogr. A, 2001, 923, 1-2, 127-136, https://doi.org/10.1016/S0021-9673(01)00929-3 . [all data]

Yasuhara, 1987
Yasuhara, A., Identification of Volatile Compounds in Poultry Manure by Gas Chromatography-Mass Spectrometry, J. Chromatogr., 1987, 387, 371-378, https://doi.org/10.1016/S0021-9673(01)94539-X . [all data]

Tello, Lebron-Aguilar, et al., 2009
Tello, A.M.; Lebron-Aguilar, R.; Quintanilla-Lopez, J.E.; Santiuste, J.M., Isothermal retention indices on poly93-cyanopropylmethyl)siloxane stationary phases, J. Chromatogr. A, 2009, 1216, 10, 1630-1639, https://doi.org/10.1016/j.chroma.2008.10.025 . [all data]

Du and Feng, 2008
Du, X.; Feng, C., Correlativity research between topological dyeing index and gas chromatography retention index of fatty esters, J. Petrochem. Univ. (Chinese), 2008, 21, 1, 16-20. [all data]

Zhao, Li, et al., 2008
Zhao, Y.; Li, J.; Xu, Y.; Duan, H.; Fan, W.; Zhao, G., EXtraction, preparation and identification of volatile compounds in Changyu XO brandy, Chinese J. Chromatogr., 2008, 26, 2, 212-222, https://doi.org/10.1016/S1872-2059(08)60014-0 . [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technicalseries1997-01-011.pdf. [all data]

Ciccioli, Cecinato, et al., 1994
Ciccioli, P.; Cecinato, A.; Brancaleoni, E.; Brachetti, A.; Frattoni, M.; Sparapani, R., Composition and Distribution of Polar and Non-Polar VOCs in Urban, Rural, Forest and Remote Areas, Eur Commission EUR, 1994, 549-568. [all data]

Ciccioli, Brancaleoni, et al., 1993
Ciccioli, P.; Brancaleoni, E.; Cecinato, A.; Sparapani, R.; Frattoni, M., Identification and determination of biogenic and anthropogenic volatile organic compounds in forest areas of Northern and Southern Europe and a remote site of the Himalaya region by high-resolution gas chromatography-mass spectrometry, J. Chromatogr., 1993, 643, 1-2, 55-69, https://doi.org/10.1016/0021-9673(93)80541-F . [all data]

Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J., Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning, Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111 . [all data]

Shibamoto, 1987
Shibamoto, T., Retention Indices in Essential Oil Analysis in Capillary Gas Chromatography in Essential Oil Analysis, Sandra, P.; Bicchi, C., ed(s)., Hutchig Verlag, Heidelberg, New York, 1987, 259-274. [all data]

Ramsey and Flanagan, 1982
Ramsey, J.D.; Flanagan, R.J., Detection and Identification of Volatile Organic Compounds in Blood by Headspace Gas Chromatography as an Aid to the Diagnosis of Solvent Abuse, J. Chromatogr., 1982, 240, 2, 423-444, https://doi.org/10.1016/S0021-9673(00)99622-5 . [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References