Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

Caprolactam

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-57.27kcal/molCcbKabo, Kozyro, et al., 1992 

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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
Deltafsolid-78.73 ± 0.40kcal/molCcbKabo, Kozyro, et al., 1992ALS
Quantity Value Units Method Reference Comment
Deltacsolid-861.32 ± 0.35kcal/molCcbKabo, Kozyro, et al., 1992ALS
Deltacsolid-861.30 ± 0.20kcal/molCcbStrepikeev, Skuratov, et al., 1955Reanalyzed by Cox and Pilcher, 1970, Original value = -861.6 kcal/mol; ALS
Deltacsolid-857.6 ± 1.5kcal/molCcbRunge and Maass, 1953At 293 °K; ALS
Quantity Value Units Method Reference Comment
solid,1 bar41.398cal/mol*KN/AKabo, Kozyro, et al., 1992, 2DH
solid,1 bar40.25cal/mol*KN/AKolesov, Paukov, et al., 1962DH
solid,1 bar40.30cal/mol*KN/AKolesov, Paukov, et al., 1959DH
solid,1 bar40.30cal/mol*KN/APaukov, Kolesov, et al., 1959Debye-Einstein extrapolation below 60 K.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
37.471298.15Kabo, Kozyro, et al., 1992, 2T = 5 to 550 K. Cp(liq) = 323.08 + 0.0342(T/K) - 1.1074x10-7(T/K)2 J/mol*K (340 to 520 K).; DH
37.36300.00Kolesov, Paukov, et al., 1962T = 60 to 350 K.; DH
37.79300.Kolesov, Paukov, et al., 1959T = 60 to 370 K.; DH
37.469298.15Paukov, Kolesov, et al., 1959T = 60 to 373 K.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
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
Tfus342.3KN/AKozyro, Marachuk, et al., 1989Uncertainty assigned by TRC = 0.5 K; TRC
Tfus342.25KN/AAnonymous, 1968TRC
Tfus342.35KN/AMastrangelo, 1957Uncertainty assigned by TRC = 0.03 K; TRC
Tfus342.2KN/AStrepikheev, Skuratov, et al., 1955Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Ttriple342.31KN/AKabo, Kozyro, et al., 1992, 2Uncertainty assigned by TRC = 0.01 K; TRC
Ttriple342.30KN/AKolesov, Paukov, et al., 1962, 2Uncertainty assigned by TRC = 0.01 K; TRC
Quantity Value Units Method Reference Comment
Deltasub20.9 ± 0.05kcal/molN/AKabo, Kozyro, et al., 1992, 2AC
Deltasub21.45 ± 0.19kcal/molVKabo, Kozyro, et al., 1992ALS

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
410.20.013Aldrich Chemical Company Inc., 1990BS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
20.856298.15N/AKabo, Kozyro, et al., 1992, 2DH
16.5 ± 0.07360.EBSteele, Chirico, et al., 2002Based on data from 350. - 568. K.; AC
15.7 ± 0.07400.EBSteele, Chirico, et al., 2002Based on data from 350. - 568. K.; AC
14.9 ± 0.05440.EBSteele, Chirico, et al., 2002Based on data from 350. - 568. K.; AC
14.1 ± 0.05480.EBSteele, Chirico, et al., 2002Based on data from 350. - 568. K.; AC
13.3 ± 0.07520.EBSteele, Chirico, et al., 2002Based on data from 350. - 568. K.; AC
12.5 ± 0.1560.EBSteele, Chirico, et al., 2002Based on data from 350. - 568. K.; AC
14.9388.AStephenson and Malanowski, 1987Based on data from 373. - 543. K.; AC

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
20.6316.MEZaitsau, Paulechka, et al., 2006Based on data from 293. - 338. K.; AC
20.8320.GSZaitsau, Paulechka, et al., 2006Based on data from 302. - 339. K.; AC
21.3 ± 0.2335.MEKabo, Kozyro, et al., 1992, 2Based on data from 330. - 340. K.; AC
20.6 ± 0.05338.CKabo, Kozyro, et al., 1992, 2AC
18.5273.AStephenson and Malanowski, 1987Based on data from 258. - 308. K.; AC
19.9 ± 0.2294. - 314.N/AAihara, 1953See also Jones, 1960, Cox and Pilcher, 1970, 2, and Aihara, 1960.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Method Reference Comment
3.8470342.305N/AKabo, Kozyro, et al., 1992, 2DH
3.8561342.36N/AMastrangelo, 1957, 2DH
3.8470342.305N/AKolesov, Paukov, et al., 1962DH
3.8470342.305N/AKolesov, Paukov, et al., 1959DH
3.862342.2N/AShevelyova, Zaitsau, et al., 2007AC
3.87342.3DSCSteele, Chirico, et al., 2002AC
3.85343.3N/AKabo, Kozyro, et al., 1992, 2AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
11.2342.305Kolesov, Paukov, et al., 1962DH
11.2342.305Kolesov, Paukov, et al., 1959DH

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

Cyclohexanone, oxime = Caprolactam

By formula: C6H11NO = C6H11NO

Quantity Value Units Method Reference Comment
Deltar-25.1 ± 1.0kcal/molCisoKozyro, Marachuk, et al., 1989, 2solid phase

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C6H11NO+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
9.07 ± 0.02PIPotapov, Filyugina, et al., 1968RDSH
9.19PETreschanke and Rademacher, 1985Vertical value; LBLHLM

IR Spectrum

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

Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, NIST Free Links, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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 Japan AIST/NIMC Database- Spectrum MS-NW-3760
NIST MS number 227792

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

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

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5MS1252.9Andriamaharavo, 201430. m/0.25 mm/0.25 «mu»m, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min)

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-5 MS1244.Kotowska, Zalikowski, et al., 201230. m/0.25 mm/0.25 «mu»m, Helium, 35. C @ 5. min, 3. K/min, 300. C @ 15. min
CapillaryOV-1011255.Zenkevich, 200525. m/0.20 mm/0.10 «mu»m, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C
CapillaryDB-51266.Savel'eva, Zenkevich, et al., 200325. m/0.20 mm/0.33 «mu»m, Helium, 40. C @ 1. min, 5. K/min, 270. C @ 15. min

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

View large format table.

Column type Active phase I Reference Comment
CapillaryMethyl Silicone1255.Savelieva and Zenkevich I., 2003Program: not specified
CapillaryMethyl Silicone1266.Savelieva and Zenkevich I., 2003Program: not specified

Lee's RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryMethyl Silicone215.49Eckel, Ross, et al., 1993Program: not specified
CapillaryMethyl Silicone217.00Eckel, Ross, et al., 1993Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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.

Kabo, Kozyro, et al., 1992
Kabo, G.J.; Kozyro, A.A.; Krouk, V.S.; Sevruk, V.M.; Yursha, I.A.; Simirsky, V.V.; Gogolinsky, V.I., Thermodynamic properties of 6-aminohexanoic lactam («epsilon»-caprolactam), J. Chem. Thermodyn., 1992, 24, 1-3. [all data]

Strepikeev, Skuratov, et al., 1955
Strepikeev, A.A.; Skuratov, S.M.; Kachinskaya, O.N.; Muromova, R.S.; Brikina, E.P.; Shtekhter, S.M., About the tension of cycle in lactames, Dokl. Akad. Nauk SSSR, 1955, 102, 105-108. [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]

Runge and Maass, 1953
Runge, F.; Maass, P., Untersuchungen uber die Beckmann=Umlagerung des Zyklohexanonoxims, Chem. Tech. (Berlin), 1953, 5, 421-424. [all data]

Kabo, Kozyro, et al., 1992, 2
Kabo, G.J.; Kozyro, A.A.; Krouk, V.S.; Sevruk, V.M.; Yursha, I.A.; Simirsky, V.V.; Gogolinsky, V.I., Thermodynamic properties of 6-aminohexanoic lactam (e-caprolactam), J. Chem. Thermodynam., 1992, 24, 1-13. [all data]

Kolesov, Paukov, et al., 1962
Kolesov, V.P.; Paukov, I.E.; Skuratov, S.M., Free energy change in the polymerization of lactams under standard conditions [low temperature heat capacities of lactams and potassium], Zhur. Fiz. Khim., 1962, 36, 770-779. [all data]

Kolesov, Paukov, et al., 1959
Kolesov, V.P.; Paukov, I.E.; Skuratov, S.M.; Seregin, E.A., Standard entropies of certain lactams, Dokl. Akad. Nauk., 1959, SSSR 128, 130-132. [all data]

Paukov, Kolesov, et al., 1959
Paukov, I.E.; Kolesov, V.P.; Skuratov, S.M., Determination of isobaric-isothermal potential at standard conditions for the polymerization reaction of e-caprolactam, Doklady Akad. Nauk, 1959, SSSR 126, 325-326. [all data]

Kozyro, Marachuk, et al., 1989
Kozyro, A.A.; Marachuk, L.I.; Krasulin, A.P.; Yursha, I.A.; Kabo, G.Ya., Thermodynamic properties of cyclohexanone oxime and «epsilon»-caprolactam, Zh. Prikl. Khim. (Leningrad), 1989, 62, 595. [all data]

Anonymous, 1968
Anonymous, X., Chemicals and Plastics Physical Properties, 1968, Union Carbide Corp., product bulletin, 1968. [all data]

Mastrangelo, 1957
Mastrangelo, S.V.R., Adiabatic calorimeter for determination of cryoscopic data., Anal. Chem., 1957, 29, 841. [all data]

Strepikheev, Skuratov, et al., 1955
Strepikheev, A.A.; Skuratov, S.M.; Kachinskaya, O.N.; Muromova, R.S.; Brykina, E.P.; Shtekher, S.M., Dokl. Akad. Nauk SSSR, 1955, 102, 105. [all data]

Kolesov, Paukov, et al., 1962, 2
Kolesov, V.P.; Paukov, I.E.; Skuratov, S.M., Free energy change in the polymerizations of lactams under standard conditions chloride), Zh. Fiz. Khim., 1962, 36, 770. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Measurements of Vapor Pressure, Heat Capacity, and Density along the Saturation Line for «gamma»-Caprolactam, Pyrazine, 1,2-Propanediol, Triethylene Glycol, Phenyl Acetylene, and Diphenyl Acetylene, J. Chem. Eng. Data, 2002, 47, 4, 689-699, https://doi.org/10.1021/je010085z . [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]

Zaitsau, Paulechka, et al., 2006
Zaitsau, Dzmitry H.; Paulechka, Yauheni U.; Kabo, Gennady J.; Kolpikau, Aleh N.; Emel'yanenko, Vladimir N.; Heintz, Andreas; Verevkin, Sergey P., Thermodynamics of the Sublimation and of the Vaporization of «gamma»-Caprolactam, J. Chem. Eng. Data, 2006, 51, 1, 130-135, https://doi.org/10.1021/je050277k . [all data]

Aihara, 1953
Aihara, A., J. Chem. Soc. Jpn. Pure Chem. Sect., 1953, 74, 437. [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [all data]

Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Aihara, 1960
Aihara, Ariyuki, Estimation of the Energy of Hydrogen Bonds Formed in Crystals. III. Amides, Bull. Chem. Soc. Jpn., 1960, 33, 9, 1188-1194, https://doi.org/10.1246/bcsj.33.1188 . [all data]

Mastrangelo, 1957, 2
Mastrangelo, S.V.R., Adiabatic calorimeter for determination of cryoscopic data, Anal. Chem., 1957, 29(5), 841-845. [all data]

Shevelyova, Zaitsau, et al., 2007
Shevelyova, Marina P.; Zaitsau, Dzmitry H.; Paulechka, Yauheni U.; Blokhin, Andrey V.; Kabo, Gennady J.; Verevkin, Sergey P.; Heintz, Andreas, Solid-Liquid Equilibrium and Activity Coefficients for Caprolactam + 1-Hexyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)imide and Cyclohexanone Oxime + 1-Hexyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)imide, J. Chem. Eng. Data, 2007, 52, 4, 1360-1365, https://doi.org/10.1021/je7000683 . [all data]

Kozyro, Marachuk, et al., 1989, 2
Kozyro, A.A.; Marachuk, L.I.; Krasulin, A.P.; Yursha, I.A.; Kabo, G.Ya., Thermodynamic properties of cyclohexanone oxime and «epsilon»-caprolactam, J. Appl. Chem. USSR, 1989, 62, 547-550. [all data]

Potapov, Filyugina, et al., 1968
Potapov, V.K.; Filyugina, A.D.; Shigorin, D.N.; Ozerova, G.A., Photoionization of some compounds containing the carbonyl and amino groups, Dokl. Akad. Nauk SSSR, 1968, 180, 398, In original 352. [all data]

Treschanke and Rademacher, 1985
Treschanke, L.; Rademacher, P., Electronic structure and conformational properties of the amide linkage, J. Mol. Struct., 1985, 122, 47. [all data]

Andriamaharavo, 2014
Andriamaharavo, N.R., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]

Kotowska, Zalikowski, et al., 2012
Kotowska, U.; Zalikowski, M.; Isidorov, V.A., HS-SPME/GC-MS analysis of volatile and semi-volatile organic compounds emitted from municipal sewage sludge, Environ. Monit. Asses., 2012, 184, 5, 2893-2907, https://doi.org/10.1007/s10661-011-2158-8 . [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Savel'eva, Zenkevich, et al., 2003
Savel'eva, E.I.; Zenkevich, I.G.; Radilov, A.S., Identification the Products of Chemical Neutralization of O-Isobutyl-S-(2-diethylaminoethyl)methylthiophosphonate in the Composition of Bitumen-Salt Matrices, Zh. Anal. Khim. (Rus.), 2003, 58, 2, 135-145. [all data]

Savelieva and Zenkevich I., 2003
Savelieva, E.; Zenkevich I., Analisi GC/MS di agenti chimici nervini, Laboratorio 2000, 2003, 17, 6/7, 24-26. [all data]

Eckel, Ross, et al., 1993
Eckel, W.P.; Ross, B.; Isensee, R.K., Pentobarbital found in ground water, Ground Water, 1993, 31, 5, 801-804, https://doi.org/10.1111/j.1745-6584.1993.tb00853.x . [all data]


Notes

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