Caprolactam

• Formula: C₆H₁₁NO
• Molecular weight: 113.1576
• IUPAC Standard InChI: InChI=1S/C6H11NO/c8-6-4-2-1-3-5-7-6/h1-5H2,(H,7,8) Copy

  
• IUPAC Standard InChIKey: JBKVHLHDHHXQEQ-UHFFFAOYSA-N Copy
• CAS Registry Number: 105-60-2
• 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: 2H-Azepin-2-one, hexahydro-; ε-Caprolactam; ω-Caprolactam; Aminocaproic lactam; Hexahydro-2-azepinone; Hexahydro-2H-azepin-2-one; Hexanoic acid, 6-amino-, cyclic lactam; 2-Azacycloheptanone; 2-Ketohexamethylenimine; 2-Oxohexamethylenimine; 2-Perhydroazepinone; 6-Caprolactam; 6-Hexanelactam; 6-Aminohexanoic acid cyclic lactam; 1,6-Hexolactam; 2-Ketohexamethyleneimine; Caprolattame; Epsylon kaprolaktam; Hexamethylenimine, 2-oxo-; Hexanoic acid, 6-amino-, lactam; Hexanonisoxim; NCI-C50646; 1-Aza-2-cycloheptanone; 2H-Azepin-7-one, hexahydro-; A1030; Akulon; Alkamid; Amilan cm 1001; Amilan cm 1011; Amilan cm 1001C; Amilan cm 1001G; 6-Aminocaproic acid lactam; ATM 2(NYLON); Bonamid; Capran 80; Capran 77C; Caprolon B; Caprolon V; Capron; Capron 8250; Capron 8252; Capron 8253; Capron 8256; Capron 8257; Capron B; Capron GR 8256; Capron GR 8258; Capron PK4; Chemlon; CM 1001; CM 1011; CM 1031; CM 1041; Danamid; Dull 704; Durethan bk; Durethan bk 30S; Durethan bkv 30H; Durethan bkv 55H; Ertalon 6sa; Extrom 6N; Grilon; Hexanolactam; Itamid; Itamid 250; Itamide 25; Itamide 35; Itamide 250; Itamide 350; Itamide 250G; Itamide S; Kaprolit; Kaprolit B; Kaprolon; Kaprolon B; Kapromine; Kapron; Kapron A; Kapron B; Maranyl F 114; Maranyl F 124; Maranyl F 500; Metamid; Miramid H 2; Miramid wm 55; Nylon A1035sf; Nylon cm 1031; Nylon X 1051; Orgamide; Orgamid RMNOCD; 2-Oxohexamethyleneimine; PA 6; PK 4; PKA; Plaskin 8200; Plaskon 201; Plaskon 8201; Plaskon 8205; Plaskon 8207; Plaskon 8252; Plaskon 8202C; Plaskon 8201hs; Plaskon xp 607; Polyamide pk 4; Relon P; Renyl MV; Sipas 60; Spencer 401; Spencer 601; Steelon; Stilon; Stylon; Tarlon X-A; Tarlon XB; Tarnamid T; Tarnamid T 2; Tarnamid T 27; Torayca N 6; UBE 1022B; Ultramid B 3; Ultramid B 4; Ultramid B 5; Ultramid BMK; Vidlon; Widlon; Zytel 211; 6-Aminohexanoic acid lactam; Hexano-6-lactam; Azepan-2-one; 2-Azepanone; 117955-36-9; 2953-03-9; 34876-18-1; 168214-28-6
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, "lite" edition (thermophysical and thermochemical data)
• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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

Constant pressure heat capacity of solid

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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

Reduced pressure boiling point

Enthalpy of vaporization

Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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

IR Spectrum

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

Data compiled by: Coblentz Society, Inc.

• Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)
• SOLUTION (10% IN CCl4 FOR 4000-1350 CM^-1, 10% IN CS2 FOR 1350-600 CM^-1); BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

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

• gas

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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.

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

Gas Chromatography

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), 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.

Normal alkane RI, non-polar column, temperature ramp

View large format table.

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

View large format table.

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

View large format table.

References

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, 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 (ε-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 ε-caprolactam, Zh. Prikl. Khim. (Leningrad), 1989, 62, 595. [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 γ-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 γ-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]

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, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization

• 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.
• Customer support for NIST Standard Reference Data products.