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, Mass spectrum (electron ionization), 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 | -186.7 ± 0.6 | kJ/mol | Ccr | Gutner, Masalitinova, et al., 1982 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2673.6 ± 0.6 | kJ/mol | Ccr | Gutner, Masalitinova, et al., 1982 | ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
164.8 | 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 |
173.89 | 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° | 45.3 ± 0.5 | kJ/mol | DSC | Rojas-Aguilar, Ginez-Carbajal, et al., 2005 | AC |
ΔvapH° | 45.0 ± 0.4 | kJ/mol | GS | Verevkin, 1998 | Based on data from 274. to 303. K.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
44.3 | 328. | TGA | Al-Najjar and Al-Sammerrai, 2007 | Based on data from 313. to 343. K.; AC |
45.6 ± 0.4 | 288. | GS | Verevkin, 1998 | Based on data from 274. to 303. K.; AC |
40.8 | 361. | N/A | Wu, Locke, et al., 1991 | Based on data from 346. to 401. K.; AC |
45.3 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 318. K. See also Cabani, Conti, et al., 1975.; AC |
42.3 | 332. | A | Stephenson and Malanowski, 1987 | Based on data from 317. to 443. K.; AC |
42.3 | 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, Mass spectrum (electron ionization), 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) | 924.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 891.2 | kJ/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 |
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
View image of digitized spectrum (can be printed in landscape orientation).
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 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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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