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Properties of substance:

ethyleneimine

Group of substances:

organic

Physical appearance:

colorless mobile liquid

Empirical formula (Hill's system for organic substances):

C2H5N

Structural formula as text:

(CH2)2NH

Molar/atomic mass: 43.07

Melting point (°C):

-73.9

Boiling point (°C):

56.7

Solubility (g/100 g of solvent):

water: 0.9116 (20°C) [Ref.]

Numerical data:

Interatomic distances (in pm): 147
Interatomic distances (in pm): 154

Density:

0.8349 (25°C, d25)

Synthesis 1:

Reference: Wenker H. The Preparation of Ethylene Imine from Monoethanolamine / Journal of the American Chemical Society. - 1935. - Vol. 57, No. 11 pp. 2328 [doi: 10.1021/ja01314a504]


H2NCH2CH2OSO3H + 2NaOH → (CH2)2NH + Na2SO4 + 2H2O

282 grams of β-aminoethylsulfuric acid is distilled with 880 g. of 40% caustic soda solution from a 3000-cc. flask. Shortly before the boiling point is reached, a reaction occurs which keeps the mixture boiling for several minutes; during this time, heating must be discontinued. When the reaction ceases, heating is resumed and a total of 240 cc. is distilled over. One distillation requires about forty-five minutes. On addition of potassium hydroxide to the distillate, 65 cc. of base separates; this is dried repeatedly with potassium hydroxide, then with sodium, and finally fractionated. The use of an efficient distilling column is recommended since the crude base contains higher boiling by-products; yield, 23 g. of ethylene imine boiling at 55—56.5° or 26.5%.

Reactions:

  1. [Ref.1]
    (CH2)2NH + NOCl + (C2H5)3N → C2H4 + N2O + (C2H5)3NHCl
  2. [Ref.1]
    (CH2)2NH + H2O → H2NCH2CH2OH

Standard molar enthalpy (heat) of formation ΔfH0 (298.15 K, kJ/mol):

91.9 (l)

Standard molar enthalpy (heat) of formation ΔfH0 (298.15 K, kJ/mol):

126.5 (g)

LD50 (mg/kg):

15 (white rats, oral)

References:

  1. CRC Handbook of Chemistry and Physics. - 90ed. - CRC Press, 2010. - pp. 5-22
  2. Yalkowsky S.H., Yan H., Jain P. Handbook of aqueous solubility data. – 2nd ed. - CRC Press, 2010. - pp. 34
  3. Вредные вещества в промышленности: Справочник для химиков, инженеров и врачей. - 7-е изд., Т.2. - Л.: Химия, 1976. - pp. 225-227 [Russian]
  4. Некрасов Б.В. Основы общей химии. - Т.1. - М.: Химия, 1973. - pp. 559 [Russian]
  5. Свойства органических соединений: Справочник. - Под ред. Потехина А.А. - Л.: Химия, 1984. - pp. 14-15 [Russian]
  6. Успехи химии. - 1966. - Т.35, №2. - pp. 229-260 [Russian]
  7. Химия: справочное руководство. - Под ред. Гаврюченкова Ф.Г., Курочкиной М.И. и др. - Л.: Химия, 1975. - pp. 357-358 [Russian]
  8. Шефтель В.О. Полимерные материалы: Токсические свойства. - Л.: Химия, 1982. - pp. 228-229 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru