Ethylenediamine - The NIST WebBook

Ethylenediamine

• Formula: C2H8N2
• Molecular weight: 60.0983
• IUPAC Standard InChI: InChI=1S/C2H8N2/c3-1-2-4/h1-4H2 Copy
• IUPAC Standard InChIKey: PIICEJLVQHRZGT-UHFFFAOYSA-N Copy
• CAS Registry Number: 107-15-3
• Chemical structure: This structure is also available as a 2d Mol file or as a computed 3d SD file View 3d structure (requires JavaScript / HTML 5)
• Other names: 1,2-Ethanediamine; β-Aminoethylamine; Dimethylenediamine; Ethane-1,2-diamine; 1,2-Diaminoethane; 1,2-Ethylenediamine; H2NCH2CH2NH2; Aethaldiamin; Aethylenediamin; 1,2-Diaminoaethan; 1,2-Diamino-ethaan; 1,2-Diamino-ethano; Ethyleendiamine; Ethylendiamine; NCI-C60402; UN 1604
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • Ion clustering data
  • Gas Chromatography
• Data at other public NIST sites:
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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
ΔfH°gas	-17.0 ± 0.59	kJ/mol	Ccr	Good and Moore, 1970

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
ΔfH°liquid	-63.01 ± 0.54	kJ/mol	Ccr	Good and Moore, 1970	ALS
Quantity	Value	Units	Method	Reference	Comment
ΔcH°liquid	-1867.3 ± 0.50	kJ/mol	Ccr	Good and Moore, 1970	ALS
Quantity	Value	Units	Method	Reference	Comment
S°liquid	202.42	J/mol*K	N/A	Messerly, Finke, et al., 1975	DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K)	Temperature (K)	Reference	Comment
172.59	298.15	Messerly, Finke, et al., 1975	T = 11 to 335 K.; DH
178.7	313.	Hough, Mason, et al., 1950	T = 313 to 333 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 ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein DRB - Donald R. Burgess, Jr. DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
Tboil	391.2	K	N/A	Aldrich Chemical Company Inc., 1990	BS
Tboil	390.29	K	N/A	Kato and Tanaka, 1989	Uncertainty assigned by TRC = 0.3 K; TRC
Tboil	389.7	K	N/A	Weast and Grasselli, 1989	BS
Tboil	390.1	K	N/A	Majer and Svoboda, 1985
Tboil	391.65	K	N/A	Anderson and Shimanskaya, 1969	Uncertainty assigned by TRC = 0.6 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Ttriple	284.290	K	N/A	Messerly, Finke, et al., 1975, 2	Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; adiabatic, A=0.03361/K; B=0.00208/K; TRC
Quantity	Value	Units	Method	Reference	Comment
Tc	613.1	K	N/A	Wilson, Wilson, et al., 1996	Uncertainty assigned by TRC = 0.3 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Pc	67.07	bar	N/A	Wilson, Wilson, et al., 1996	Uncertainty assigned by TRC = 0.10 bar; TRC
Quantity	Value	Units	Method	Reference	Comment
ΔvapH°	46. ± 6.	kJ/mol	AVG	N/A	Average of 9 values; Individual data points

Enthalpy of vaporization

ΔvapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
37.98	390.1	N/A	Majer and Svoboda, 1985
43.9	318.	A	Stephenson and Malanowski, 1987	Based on data from 303. to 391. K.; AC
45.9	299.	A,IP	Stephenson and Malanowski, 1987	Based on data from 284. to 419. K. See also Messerly, Finke, et al., 1975.; AC
45.6	314.	N/A	Hieber and Woerner, 1934	Based on data from 299. to 390. K. See also Boublik, Fried, et al., 1984.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C)) P = vapor pressure (bar) T = temperature (K)

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Temperature (K)	A	B	C	Reference	Comment
299.66 to 390.6	4.22368	1302.256	-81.788	Hieber and Woerner, 1934	Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kJ/mol)	Temperature (K)	Method	Reference	Comment
65.6	263.	IP	Stephenson and Malanowski, 1987	Based on data from 242. to 278. K. See also Messerly, Finke, et al., 1975.; AC

Enthalpy of fusion

ΔfusH (kJ/mol)	Temperature (K)	Method	Reference	Comment
21.08	284.1	DSC	Lee, Chang, et al., 1997	AC
22.58	284.3	AC	Acree, 1991	See also Lee, Lien, et al., 1994 and Messerly, Finke, et al., 1975.; AC

Enthalpy of phase transition

ΔHtrs (kJ/mol)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
0.4874	189.0	crystaline, II	crystaline, I	Messerly, Finke, et al., 1975	DH
22.5831	284.29	crystaline, I	liquid	Messerly, Finke, et al., 1975	DH

Entropy of phase transition

ΔStrs (J/mol*K)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
2.58	189.0	crystaline, II	crystaline, I	Messerly, Finke, et al., 1975	DH
79.44	284.29	crystaline, I	liquid	Messerly, Finke, et al., 1975	DH

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Reaction 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: M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

( • 2) + = ( • 3)

By formula: (K+ • 2C2H8N2) + C2H8N2 = (K+ • 3C2H8N2)

Bond type: Polydentate bonding in non-hydrogen-bonded positive ions

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	54.0	kJ/mol	HPMS	Davidson and Kebarle, 1976	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	110.	J/mol*K	HPMS	Davidson and Kebarle, 1976	gas phase; M

( • ) + = ( • 2)

By formula: (K+ • C2H8N2) + C2H8N2 = (K+ • 2C2H8N2)

Bond type: Polydentate bonding in non-hydrogen-bonded positive ions

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	92.9	kJ/mol	HPMS	Davidson and Kebarle, 1976	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	134.	J/mol*K	HPMS	Davidson and Kebarle, 1976	gas phase; M

(C2H9N+ • 2) + = (C2H9N+ • 3)

By formula: (C2H9N+ • 2C2H8N2) + C2H8N2 = (C2H9N+ • 3C2H8N2)

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	73.2	kJ/mol	HPMS	Wincel and Herman, 1973	gas phase; Entropy change is questionable; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	199.	J/mol*K	HPMS	Wincel and Herman, 1973	gas phase; Entropy change is questionable; M

+ = ( • )

By formula: K+ + C2H8N2 = (K+ • C2H8N2)

Bond type: Polydentate bonding in non-hydrogen-bonded positive ions

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	108.	kJ/mol	HPMS	Davidson and Kebarle, 1976	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	93.3	J/mol*K	HPMS	Davidson and Kebarle, 1976	gas phase; M

+ =

By formula: C2H8N2 + C2H5N = C4H13N3

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	82.8 ± 5.0	kJ/mol	Cm	Dalin, Bobylev, et al., 1988	liquid phase; solvent: Aqueous HCl; Kinetic; ALS

Henry's Law 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 by: Rolf Sander

Henry's Law constant (water solution)

kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K))) k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar)) d(ln(kH))/d(1/T) = Temperature dependence constant (K)

k°H (mol/(kg*bar))	d(ln(kH))/d(1/T) (K)	Method	Reference
580000.	M	N/A

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (11% CCl4 FOR 3800-1000, 6% CS2 FOR 1000-650, AND 11% CCl4 FOR 650-250); PERKIN-ELMER 521 (GRATING); 2 cm-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law 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

Spectrum

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Additional Data

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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	291549

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, 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.

Good and Moore, 1970 Good, W.D.; Moore, R.T., Enthalpies of formation of ethylenediamine, 1,2,-propanediamine, 1,2,-butanediamine, 2-methyl-1,2-propanediamine, and isobutylamine C-N and N-F Thermochemical bond energies, J. Chem. Eng. Data, 1970, 15, 150-154. [all data]

Messerly, Finke, et al., 1975 Messerly, J.F.; Finke, H.L.; Osborn, A.G.; Douslin, D.R., Low-temperature calorimetric and vapor-pressure studies on alkanediamines, J. Chem. Thermodynam., 1975, 7, 1029-1046. [all data]

Hough, Mason, et al., 1950 Hough, E.W.; Mason, D.M.; Sage, B.H., Heat capacities of several organic liquids, J. Am. Chem. Soc., 1950, 72, 5775-5777. [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]

Kato and Tanaka, 1989 Kato, M.; Tanaka, H., Vapor-Liquid Equilibrium Determination with a Flow-Type Ebulliometer for Six Binary Systems Made of Alcohol and Amine, J. Chem. Eng. Data, 1989, 34, 203. [all data]

Weast and Grasselli, 1989 CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Majer and Svoboda, 1985 Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Anderson and Shimanskaya, 1969 Anderson, A.A.; Shimanskaya, M.V., Gas-Liquid Chromatography of some Aliphatic and Heterocyclic Polyfunctional Amines: II. Solution Thermodyn. of Amines in Fix. Phas., Latv. PSR Zinat. Akad. Vestis, Kim. Ser., 1969, No. 5, 527. [all data]

Messerly, Finke, et al., 1975, 2 Messerly, J.F.; Finke, H.L.; Osborn, A.G.; Douslin, D.R., Low-temperature calorimetric and vapor-pressure studies on alkanediamines, J. Chem. Thermodyn., 1975, 7, 1029-46. [all data]

Wilson, Wilson, et al., 1996 Wilson, L.C.; Wilson, H.L.; Wilding, W.V.; Wilson, G.M., Critical Point Measurements for Fourteen Compounds by a Static Method and a Flow Method, J. Chem. Eng. Data, 1996, 41, 1252-4. [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]

Hieber and Woerner, 1934 Hieber, W.; Woerner, A., Thermochemische Messungen an Komplexbildenden Aminen und Alkoholen, Zeitschrift für Elektrochemie und angewandte physikalische Chemie, 1934, 40, 5, 252-256, https://doi.org/10.1002/bbpc.19340400508 . [all data]

Boublik, Fried, et al., 1984 Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Lee, Chang, et al., 1997 Lee, Ming-Jer; Chang, Yao-Kun; Lin, Ho-mu; Chen, Chang-Hsin, Solid-Liquid Equilibria for 4-Methoxyphenol with Catechol, Ethylenediamine, or Piperazine, J. Chem. Eng. Data, 1997, 42, 2, 349-352, https://doi.org/10.1021/je960201b . [all data]

Acree, 1991 Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Lee, Lien, et al., 1994 Lee, Ming-Jer; Lien, Pei-Jung; Huang, Wen-Kuo, Solid-Liquid Equilibria for Binary Mixtures Containing Cresols, Ethylenediamine, and Anisole, Ind. Eng. Chem. Res., 1994, 33, 11, 2853-2858, https://doi.org/10.1021/ie00035a040 . [all data]

Davidson and Kebarle, 1976 Davidson, W.R.; Kebarle, P., Binding Energies and Stabilities of Potassium Ion Complexes with Ethylene Diamine and Dimethoxyethane (Glyme) from Measurements of the Complexing Equilibria in the Gas Phase, Can. J. Chem., 1976, 54, 16, 2594, https://doi.org/10.1139/v76-368 . [all data]

Wincel and Herman, 1973 Wincel, H.; Herman, J.A., Photoionization Study of Clustering Reactions in Diamines: Ethane-1,2-diamine, Propane-1,2-diamine and Propane-1,3-diamine, J. Chem. Soc. Faraday Trans., 1973, 69, 1797, https://doi.org/10.1039/f19736901797 . [all data]

Dalin, Bobylev, et al., 1988 Dalin, A.R.; Bobylev, V.A.; Suslikov, V.F.; Kamskaya, O.I.; Tereshchenko, G.F., Nucleophilic cleavage and the formation of saturated heterocycles. VII. Kinetic and thermochemical study of reactions of aziridine with ethylene amines, J. Gen. Chem. USSR, 1988, 58, 1868-1871. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:

  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Ttriple	Triple point temperature
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  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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