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:
  • Condensed phase thermochemistry data
  • Phase change data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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 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

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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
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

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, 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]

Notes

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• 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°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

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