Morpholine

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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

Quantity Value Units Method Reference Comment
Δfliquid-44.6 ± 0.1kcal/molCcrGutner, Masalitinova, et al., 1982ALS
Quantity Value Units Method Reference Comment
Δcliquid-639.0 ± 0.1kcal/molCcrGutner, Masalitinova, et al., 1982ALS

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
39.39298.15Lyashkov, 1980T = 293 to 353 K. Data given graphically. Cp value calculated from equation: Cp(J/g*K) = 1.785 + 0.00427 T(°C).; DH
41.561298.Trimble, Engle, et al., 1942T = 273 to 403 K.; DH

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
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil401.6 ± 0.8KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus268.35KN/AVedal, Ellestad, et al., 1976Uncertainty assigned by TRC = 1. K; TRC
Tfus270.1KN/AAnonymous, 1955Uncertainty assigned by TRC = 0.4 K; TRC
Tfus268.KN/ADreisbach, 1955Uncertainty assigned by TRC = 0.02 K; TRC
Tfus268.3KN/ADermer and Dermer, 1937Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Δvap10.8 ± 0.1kcal/molDSCRojas-Aguilar, Ginez-Carbajal, et al., 2005AC
Δvap10.8 ± 0.1kcal/molGSVerevkin, 1998Based on data from 274. to 303. K.; AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
10.6328.TGAAl-Najjar and Al-Sammerrai, 2007Based on data from 313. to 343. K.; AC
10.9 ± 0.1288.GSVerevkin, 1998Based on data from 274. to 303. K.; AC
9.75361.N/AWu, Locke, et al., 1991Based on data from 346. to 401. K.; AC
10.8288.AStephenson and Malanowski, 1987Based on data from 273. to 318. K. See also Cabani, Conti, et al., 1975.; AC
10.1332.AStephenson and Malanowski, 1987Based on data from 317. to 443. K.; AC
10.1333.EBPalczewska-Tulinska, Cholinski, et al., 1983Based on data from 318. to 401. K.; AC

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

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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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Quantity Value Units Method Reference Comment
Proton affinity (review)220.9kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity213.0kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.88 ± 0.05PEDomelsmith and Houk, 1977Vertical value; LLK
8.91 ± 0.03PEColonna, Distefano, et al., 1975Vertical value; LLK

IR Spectrum

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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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


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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Mass spectrum
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Additional Data

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Due to licensing restrictions, this spectrum cannot be downloaded.

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 NIST Mass Spectrometry Data Center, 1998.
NIST MS number 291444

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryOV-101110.794.Zhuravleva, 200050. m/0.3 mm/0.4 μm, He
PackedSE-30150.795.Tiess, 1984Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m
PackedPMS-100130.766.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPMS-100150.750.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPMS-100180.749.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m

Kovats' RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
PackedSE-30810.Ramsey, Lee, et al., 1980He, Chromosorb G HP (80-100 mesh); Column length: 1.5 m; Program: not specified

Kovats' RI, polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedPEG-2000150.1274.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000152.1273.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000179.1303.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000180.1281.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000200.1312.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m
PackedPEG-2000200.1330.Anderson, Jurel, et al., 1973He, Celite 545 (44-60 mesh); Column length: 3. m

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillarySPB-1779.Flanagan, Streete, et al., 199760. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C
CapillarySPB-1779.Strete, Ruprah, et al., 199260. m/0.53 mm/5.0 μm, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C
CapillarySPB-1800.Strete, Ruprah, et al., 199260. m/0.53 mm/5.0 μm, Helium; Program: not specified
OtherMethyl Silicone810.Ardrey and Moffat, 1981Program: not specified

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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.

Gutner, Masalitinova, et al., 1982
Gutner, N.M.; Masalitinova, T.N.; Mon'yakova, O.N.; Lebedeva, N.D., Heats of combustion and formation of some cyclic compounds, Termodin. Organ. Soedin., 1982, 46-49. [all data]

Lyashkov, 1980
Lyashkov, V.I., Thermal characteristics of morpholine, Izv. Vyssh. Uchebn., Khim. Khim. Tekhnol., 1980, 23, 1085-1086. [all data]

Trimble, Engle, et al., 1942
Trimble, H.M.; Engle, C.J.; Brown, R.A.; Schmuck, R.F., The specific heats of morpholine and its aqueous solutions, J. Am. Chem. Soc., 1942, 64, 679-681. [all data]

Vedal, Ellestad, et al., 1976
Vedal, D.; Ellestad, O.H.; Klaeboe, P.; Hagen, G., The vibrational spectra of piperidine and morpholine and their N-deuterated analogs, spectrochim. Acta, Part A, 1976, 32, 877. [all data]

Anonymous, 1955
Anonymous, R., , Am. Pet. Inst. Res. Proj. 45, Tech. Rep. 14, No. 1, Ohio State Univ., 1955. [all data]

Dreisbach, 1955
Dreisbach, R.R., Physical Properties of Chemical Compounds, Advances in Chemistry Series No. 15, Am. Chem. Soc.: Washington, D. C., 1955. [all data]

Dermer and Dermer, 1937
Dermer, V.H.; Dermer, O.C., Physical constants of morpholine., J. Am. Chem. Soc., 1937, 59, 1148. [all data]

Rojas-Aguilar, Ginez-Carbajal, et al., 2005
Rojas-Aguilar, A.; Ginez-Carbajal, F.; Orozco-Guareno, E.; Flores-Segura, H., Measurement of enthalpies of vaporization of volatile heterocyclic compounds by DSC, J Therm Anal Calorim, 2005, 79, 1, 95-100, https://doi.org/10.1007/s10973-004-0568-3 . [all data]

Verevkin, 1998
Verevkin, Sergey P., Thermochemistry of amines: strain in six-membered rings from experimental standard molar enthalpies of formation of morpholines and piperazines, The Journal of Chemical Thermodynamics, 1998, 30, 9, 1069-1079, https://doi.org/10.1006/jcht.1998.0371 . [all data]

Al-Najjar and Al-Sammerrai, 2007
Al-Najjar, Hazim; Al-Sammerrai, Dhoaib, Thermogravimetric determination of the heat of vaporization of some highly polar solvents, J. Chem. Technol. Biotechnol., 2007, 37, 3, 145-152, https://doi.org/10.1002/jctb.280370302 . [all data]

Wu, Locke, et al., 1991
Wu, Huey S.; Locke, William E.; Sandler, Stanley I., Isothermal vapor-liquid equilibrium of binary mixtures containing morpholine, J. Chem. Eng. Data, 1991, 36, 1, 127-130, https://doi.org/10.1021/je00001a037 . [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]

Cabani, Conti, et al., 1975
Cabani, Sergio; Conti, G.; Giannessi, D.; Lepori, L., Thermodynamic study of aqueous dilute solutions of organic compounds. Part 3.---Morpholines and piperazines, J. Chem. Soc., Faraday Trans. 1, 1975, 71, 0, 1154, https://doi.org/10.1039/f19757101154 . [all data]

Palczewska-Tulinska, Cholinski, et al., 1983
Palczewska-Tulinska, Marcela; Cholinski, Jacek; Szafranski, Andrzej; Wyrzykowska-Stankiewicz, Danuta, Maximum-likelihood evaluation of antoine equation constants for vapor pressures of morpholine, n-heptane, cyclohexane and methylcyclohexane, Fluid Phase Equilibria, 1983, 11, 3, 233-243, https://doi.org/10.1016/0378-3812(83)85026-2 . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Domelsmith and Houk, 1977
Domelsmith, L.N.; Houk, K.N., Photoelectron spectra of cyclopentanone and cyclohexanone enamines, Tetrahedron Lett., 1977, 23, 1981. [all data]

Colonna, Distefano, et al., 1975
Colonna, F.P.; Distefano, G.; Pignataro, S.; Pitacco, G.; Valentin, E., Ionization energies of some amines and enamines and an estimation of their relative basicity in gaseous phase, J. Chem. Soc. Faraday Trans. 2, 1975, 71, 1572. [all data]

Zhuravleva, 2000
Zhuravleva, I.L., Evaluation of the polarity and boiling points of nitrogen-containing heterocyclic compounds by gas chromatography, Russ. Chem. Bull. (Engl. Transl.), 2000, 49, 2, 325-328, https://doi.org/10.1007/BF02494682 . [all data]

Tiess, 1984
Tiess, D., Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30, Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [all data]

Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L., Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases, Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]

Ramsey, Lee, et al., 1980
Ramsey, J.D.; Lee, T.D.; Osselton, M.D.; Moffat, A.C., Gas-liquid chromatographic retention indices of 296 non-drug substances on SE-30 or OV-1 likely to be encountered in toxicological analyses, J. Chromatogr., 1980, 184, 2, 185-206, https://doi.org/10.1016/S0021-9673(00)85641-1 . [all data]

Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technicalseries1997-01-011.pdf. [all data]

Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J., Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning, Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111 . [all data]

Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References