Caprolactam
- Formula: C6H11NO
- Molecular weight: 113.1576
- IUPAC Standard InChIKey: JBKVHLHDHHXQEQ-UHFFFAOYSA-N
- 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:
- Other data available:
- Data at other public NIST sites:
- Options:
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 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -239.6 | kJ/mol | Ccb | Kabo, Kozyro, et al., 1992 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -329.4 ± 1.7 | kJ/mol | Ccb | Kabo, Kozyro, et al., 1992 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -3603.8 ± 1.5 | kJ/mol | Ccb | Kabo, Kozyro, et al., 1992 | ALS |
ΔcH°solid | -3603.7 ± 0.84 | kJ/mol | Ccb | Strepikeev, Skuratov, et al., 1955 | Reanalyzed by Cox and Pilcher, 1970, Original value = -3605. kJ/mol; ALS |
ΔcH°solid | -3588. ± 6.3 | kJ/mol | Ccb | Runge and Maass, 1953 | At 293 °K; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 173.21 | J/mol*K | N/A | Kabo, Kozyro, et al., 1992, 2 | DH |
S°solid,1 bar | 168.4 | J/mol*K | N/A | Kolesov, Paukov, et al., 1962 | DH |
S°solid,1 bar | 168.6 | J/mol*K | N/A | Kolesov, Paukov, et al., 1959 | DH |
S°solid,1 bar | 168.6 | J/mol*K | N/A | Paukov, Kolesov, et al., 1959 | Debye-Einstein extrapolation below 60 K.; DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
156.78 | 298.15 | Kabo, Kozyro, et al., 1992, 2 | T = 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 |
156.3 | 300.00 | Kolesov, Paukov, et al., 1962 | T = 60 to 350 K.; DH |
158.1 | 300. | Kolesov, Paukov, et al., 1959 | T = 60 to 370 K.; DH |
156.77 | 298.15 | Paukov, Kolesov, et al., 1959 | T = 60 to 373 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 342.3 | K | N/A | Kozyro, Marachuk, et al., 1989 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 342.35 | K | N/A | Mastrangelo, 1957 | Uncertainty assigned by TRC = 0.03 K; TRC |
Tfus | 342.2 | K | N/A | Strepikheev, Skuratov, et al., 1955 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 342.31 | K | N/A | Kabo, Kozyro, et al., 1992, 2 | Uncertainty assigned by TRC = 0.01 K; TRC |
Ttriple | 342.30 | K | N/A | Kolesov, Paukov, et al., 1962, 2 | Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 87.3 ± 0.2 | kJ/mol | N/A | Kabo, Kozyro, et al., 1992, 2 | AC |
ΔsubH° | 89.76 ± 0.81 | kJ/mol | V | Kabo, Kozyro, et al., 1992 | ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
410.2 | 0.013 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
87.260 | 298.15 | N/A | Kabo, Kozyro, et al., 1992, 2 | DH |
69.2 ± 0.3 | 360. | EB | Steele, Chirico, et al., 2002 | Based on data from 350. to 568. K.; AC |
65.7 ± 0.3 | 400. | EB | Steele, Chirico, et al., 2002 | Based on data from 350. to 568. K.; AC |
62.3 ± 0.2 | 440. | EB | Steele, Chirico, et al., 2002 | Based on data from 350. to 568. K.; AC |
59.0 ± 0.2 | 480. | EB | Steele, Chirico, et al., 2002 | Based on data from 350. to 568. K.; AC |
55.7 ± 0.3 | 520. | EB | Steele, Chirico, et al., 2002 | Based on data from 350. to 568. K.; AC |
52.4 ± 0.5 | 560. | EB | Steele, Chirico, et al., 2002 | Based on data from 350. to 568. K.; AC |
62.3 | 388. | A | Stephenson and Malanowski, 1987 | Based on data from 373. to 543. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
86.3 | 316. | ME | Zaitsau, Paulechka, et al., 2006 | Based on data from 293. to 338. K.; AC |
86.9 | 320. | GS | Zaitsau, Paulechka, et al., 2006 | Based on data from 302. to 339. K.; AC |
89.3 ± 0.8 | 335. | ME | Kabo, Kozyro, et al., 1992, 2 | Based on data from 330. to 340. K.; AC |
86.3 ± 0.2 | 338. | C | Kabo, Kozyro, et al., 1992, 2 | AC |
77.5 | 273. | A | Stephenson and Malanowski, 1987 | Based on data from 258. to 308. K.; AC |
83.3 ± 0.8 | 294. to 314. | N/A | Aihara, 1953 | See also Jones, 1960, Cox and Pilcher, 1970, 2, and Aihara, 1960.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
16.096 | 342.305 | N/A | Kabo, Kozyro, et al., 1992, 2 | DH |
16.134 | 342.36 | N/A | Mastrangelo, 1957, 2 | DH |
16.096 | 342.305 | N/A | Kolesov, Paukov, et al., 1962 | DH |
16.096 | 342.305 | N/A | Kolesov, Paukov, et al., 1959 | DH |
16.16 | 342.2 | N/A | Shevelyova, Zaitsau, et al., 2007 | AC |
16.2 | 342.3 | DSC | Steele, Chirico, et al., 2002 | AC |
16.1 | 343.3 | N/A | Kabo, Kozyro, et al., 1992, 2 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
47.0 | 342.305 | Kolesov, Paukov, et al., 1962 | DH |
47.0 | 342.305 | Kolesov, Paukov, et al., 1959 | DH |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5MS | 1252.9 | Andriamaharavo, 2014 | 30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min) |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 MS | 1244. | Kotowska, Zalikowski, et al., 2012 | 30. m/0.25 mm/0.25 μm, Helium, 35. C @ 5. min, 3. K/min, 300. C @ 15. min |
Capillary | OV-101 | 1255. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Capillary | DB-5 | 1266. | Savel'eva, Zenkevich, et al., 2003 | 25. m/0.20 mm/0.33 μm, Helium, 40. C @ 1. min, 5. K/min, 270. C @ 15. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 1255. | Savelieva and Zenkevich I., 2003 | Program: not specified |
Capillary | Methyl Silicone | 1266. | Savelieva and Zenkevich I., 2003 | Program: not specified |
Lee's RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 215.49 | Eckel, Ross, et al., 1993 | Program: not specified |
Capillary | Methyl Silicone | 217.00 | Eckel, Ross, et al., 1993 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, 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]
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 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.