Morpholine
- Formula: C4H9NO
- Molecular weight: 87.1204
- IUPAC Standard InChIKey: YNAVUWVOSKDBBP-UHFFFAOYSA-N
- CAS Registry Number: 110-91-8
- 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: p-Isoxazine, tetrahydro-; BASF 238; Diethylene Imidoxide; Diethylene oximide; Diethylenimide oxide; Tetrahydro-p-oxazine; Tetrahydro-1,4-oxazine; Tetrahydro-2H-1,4-oxazine; 1-Oxa-4-azacyclohexane; 2H-1,4-Oxazine, tetrahydro-; 4H-1,4-Oxazine, tetrahydro-; Diethyleneimide oxide; Tetrahydro-1,4-isoxazine; Drewamine; NA 2054; UN 2054; NSC 9376
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, 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°liquid | -44.6 ± 0.1 | kcal/mol | Ccr | Gutner, Masalitinova, et al., 1982 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -639.0 ± 0.1 | kcal/mol | Ccr | Gutner, Masalitinova, et al., 1982 | ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
39.39 | 298.15 | Lyashkov, 1980 | T = 293 to 353 K. Data given graphically. Cp value calculated from equation: Cp(J/g*K) = 1.785 + 0.00427 T(°C).; DH |
41.561 | 298. | Trimble, Engle, et al., 1942 | T = 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 |
---|---|---|---|---|---|
Tboil | 401.6 ± 0.8 | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 268.35 | K | N/A | Vedal, Ellestad, et al., 1976 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 270.1 | K | N/A | Anonymous, 1955 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 268. | K | N/A | Dreisbach, 1955 | Uncertainty assigned by TRC = 0.02 K; TRC |
Tfus | 268.3 | K | N/A | Dermer and Dermer, 1937 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 10.8 ± 0.1 | kcal/mol | DSC | Rojas-Aguilar, Ginez-Carbajal, et al., 2005 | AC |
ΔvapH° | 10.8 ± 0.1 | kcal/mol | GS | Verevkin, 1998 | Based on data from 274. to 303. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.6 | 328. | TGA | Al-Najjar and Al-Sammerrai, 2007 | Based on data from 313. to 343. K.; AC |
10.9 ± 0.1 | 288. | GS | Verevkin, 1998 | Based on data from 274. to 303. K.; AC |
9.75 | 361. | N/A | Wu, Locke, et al., 1991 | Based on data from 346. to 401. K.; AC |
10.8 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 318. K. See also Cabani, Conti, et al., 1975.; AC |
10.1 | 332. | A | Stephenson and Malanowski, 1987 | Based on data from 317. to 443. K.; AC |
10.1 | 333. | EB | Palczewska-Tulinska, Cholinski, et al., 1983 | Based on data from 318. to 401. K.; AC |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, 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 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) | 220.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 213.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.88 ± 0.05 | PE | Domelsmith and Houk, 1977 | Vertical value; LLK |
8.91 ± 0.03 | PE | Colonna, Distefano, et al., 1975 | Vertical 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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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
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 |
Gas Chromatography
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-101 | 110. | 794. | Zhuravleva, 2000 | 50. m/0.3 mm/0.4 μm, He |
Packed | SE-30 | 150. | 795. | Tiess, 1984 | Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m |
Packed | PMS-100 | 130. | 766. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PMS-100 | 150. | 750. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PMS-100 | 180. | 749. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 810. | Ramsey, Lee, et al., 1980 | He, Chromosorb G HP (80-100 mesh); Column length: 1.5 m; Program: not specified |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | PEG-2000 | 150. | 1274. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 152. | 1273. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 179. | 1303. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 180. | 1281. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 200. | 1312. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 200. | 1330. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SPB-1 | 779. | Flanagan, Streete, et al., 1997 | 60. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C |
Capillary | SPB-1 | 779. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C |
Capillary | SPB-1 | 800. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: not specified |
Other | Methyl Silicone | 810. | Ardrey and Moffat, 1981 | Program: not specified |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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, Gas Chromatography, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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