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Properties of substance:

ethyl isocyanate

Group of substances:

organic

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

C3H5NO

Structural formula as text:

C2H5NCO

Molar/atomic mass: 71.078

Boiling point (°C):

60

CAS №: 109-90-0

Synthesis 1:

Reference: Bieber, T. I. Preparation of Alkyl Isocyanates Using Alkyl Phosphates / Journal of the American Chemical Society. - 1952. - Vol. 74, No. 18 pp. 4701 [doi: 10.1021/ja01138a501]


(C2H5O)3PO + KNCO → (C2H5O)2PO2K + C2H5NCO

In a 500-ml. distilling flask were placed 98 g. of triethyl phosphate and 30 g. of potassium cyanate (along with a few glass beads). Potassium cyanate does not dissolve appreciably in triethyl phosphate, even at higher temperatures. The mixture was strongly heated until distillation occurred. For the next ten minutes heat was applied on and off to maintain distillation at a fairly even rate. The reaction mixture became quite viscous by the end of this time and heating was discontinued when strong white fumes due to the condensation of water vapor started to appear, the water being a result of decomposition within the viscous mass. A parallel experiment had shown that when these fumes were allowed to distil, water droplets appeared in the distillate and caused the evolution of carbon dioxide from the latter (hydrolysis of ethyl isocyanate). The viscous residue in the distilling flask set to a gel on cooling. It consisted chiefly of potassium diethyl phosphate along with some triethyl phosphate.

The distillate, a mixture of ethyl isocyanate and triethyl phosphate, was subjected to distillation, and 16.5 g. of ethyl isocyanate (a 63% yield based on potassium cyanate) was collected at 60—63°. The high-boiling liquid residue from the distillation was triethyl phosphate (16.3 g.). An experiment employing a smaller relative amount of triethyl phosphate than used above gave a less satisfactory result, since the reaction mixture became viscous and gave rise to water vapor before much product had been collected.

References:

  1. Dictionary of organic compounds. - Vol. 2, Eccaine - Myrtillin chloride. - London, 1946. - pp. 39
  2. Свойства органических соединений: Справочник. - Под ред. Потехина А.А. - Л.: Химия, 1984. - pp. 446-447 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru