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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Condensed phase thermochemistry data
Go To: Top, 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 |
References
Go To: Top, Condensed phase thermochemistry 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]
Notes
Go To: Top, Condensed phase thermochemistry data, 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°solid Enthalpy of formation of solid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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