Caprolactam

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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

Quantity Value Units Method Reference Comment
Tfus342.3KN/AKozyro, Marachuk, et al., 1989Uncertainty assigned by TRC = 0.5 K; TRC
Tfus342.35KN/AMastrangelo, 1957Uncertainty assigned by TRC = 0.03 K; TRC
Tfus342.2KN/AStrepikheev, Skuratov, et al., 1955Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Ttriple342.31KN/AKabo, Kozyro, et al., 1992Uncertainty assigned by TRC = 0.01 K; TRC
Ttriple342.30KN/AKolesov, Paukov, et al., 1962Uncertainty assigned by TRC = 0.01 K; TRC
Quantity Value Units Method Reference Comment
Δsub20.9 ± 0.05kcal/molN/AKabo, Kozyro, et al., 1992AC
Δsub21.45 ± 0.19kcal/molVKabo, Kozyro, et al., 1992, 2ALS

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
410.20.013Aldrich Chemical Company Inc., 1990BS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
20.856298.15N/AKabo, Kozyro, et al., 1992DH
16.5 ± 0.07360.EBSteele, Chirico, et al., 2002Based on data from 350. to 568. K.; AC
15.7 ± 0.07400.EBSteele, Chirico, et al., 2002Based on data from 350. to 568. K.; AC
14.9 ± 0.05440.EBSteele, Chirico, et al., 2002Based on data from 350. to 568. K.; AC
14.1 ± 0.05480.EBSteele, Chirico, et al., 2002Based on data from 350. to 568. K.; AC
13.3 ± 0.07520.EBSteele, Chirico, et al., 2002Based on data from 350. to 568. K.; AC
12.5 ± 0.1560.EBSteele, Chirico, et al., 2002Based on data from 350. to 568. K.; AC
14.9388.AStephenson and Malanowski, 1987Based on data from 373. to 543. K.; AC

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
20.6316.MEZaitsau, Paulechka, et al., 2006Based on data from 293. to 338. K.; AC
20.8320.GSZaitsau, Paulechka, et al., 2006Based on data from 302. to 339. K.; AC
21.3 ± 0.2335.MEKabo, Kozyro, et al., 1992Based on data from 330. to 340. K.; AC
20.6 ± 0.05338.CKabo, Kozyro, et al., 1992AC
18.5273.AStephenson and Malanowski, 1987Based on data from 258. to 308. K.; AC
19.9 ± 0.2294. to 314.N/AAihara, 1953See also Jones, 1960, Cox and Pilcher, 1970, and Aihara, 1960.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
3.8470342.305N/AKabo, Kozyro, et al., 1992DH
3.8561342.36N/AMastrangelo, 1957, 2DH
3.8470342.305N/AKolesov, Paukov, et al., 1962, 2DH
3.8470342.305N/AKolesov, Paukov, et al., 1959DH
3.862342.2N/AShevelyova, Zaitsau, et al., 2007AC
3.87342.3DSCSteele, Chirico, et al., 2002AC
3.85343.3N/AKabo, Kozyro, et al., 1992AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
11.2342.305Kolesov, Paukov, et al., 1962, 2DH
11.2342.305Kolesov, Paukov, et al., 1959DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Gas phase ion energetics data

Go To: Top, 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 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

IE (eV) Method Reference Comment
9.07 ± 0.02PIPotapov, Filyugina, et al., 1968RDSH
9.19PETreschanke and Rademacher, 1985Vertical value; LBLHLM

References

Go To: Top, Phase change data, Gas phase ion energetics data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

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 (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 polymerizations of lactams under standard conditions chloride), Zh. Fiz. Khim., 1962, 36, 770. [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 (ε-caprolactam), J. Chem. Thermodyn., 1992, 24, 1-3. [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
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]

Kolesov, Paukov, et al., 1962, 2
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]

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]


Notes

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