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)
- 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
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Gas 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -57.27 | kcal/mol | Ccb | Kabo, Kozyro, et al., 1992 |
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -78.73 ± 0.40 | kcal/mol | Ccb | Kabo, Kozyro, et al., 1992 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -861.32 ± 0.35 | kcal/mol | Ccb | Kabo, Kozyro, et al., 1992 | ALS |
| ΔcH°solid | -861.30 ± 0.20 | kcal/mol | Ccb | Strepikeev, Skuratov, et al., 1955 | Reanalyzed by Cox and Pilcher, 1970, Original value = -861.6 kcal/mol; ALS |
| ΔcH°solid | -857.6 ± 1.5 | kcal/mol | Ccb | Runge and Maass, 1953 | At 293 °K; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 41.398 | cal/mol*K | N/A | Kabo, Kozyro, et al., 1992, 2 | DH |
| S°solid,1 bar | 40.25 | cal/mol*K | N/A | Kolesov, Paukov, et al., 1962 | DH |
| S°solid,1 bar | 40.30 | cal/mol*K | N/A | Kolesov, Paukov, et al., 1959 | DH |
| S°solid,1 bar | 40.30 | cal/mol*K | N/A | Paukov, Kolesov, et al., 1959 | Debye-Einstein extrapolation below 60 K.; DH |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 37.471 | 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 |
| 37.36 | 300.00 | Kolesov, Paukov, et al., 1962 | T = 60 to 350 K.; DH |
| 37.79 | 300. | Kolesov, Paukov, et al., 1959 | T = 60 to 370 K.; DH |
| 37.469 | 298.15 | Paukov, Kolesov, et al., 1959 | T = 60 to 373 K.; DH |
IR Spectrum
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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
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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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 | Japan AIST/NIMC Database- Spectrum MS-NW-3760 |
| NIST MS number | 227792 |
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
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, 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]
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, 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) 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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