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Synthesis of hydroxyethylhydrazine by the Raschig process and comparison with synthesis by the alkylation process
Author(s) -
Goutelle V.,
Pasquet V.,
Hajj A. El,
Bougrine A. J.,
Delalu H.
Publication year - 2011
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/kin.20559
Subject(s) - chemistry , alkylation , epoxide , hydroxide , hydrazine (antidepressant) , mass spectrometry , sodium hydroxide , molar ratio , reaction mechanism , inorganic chemistry , organic chemistry , catalysis , chromatography
The Raschig synthesis of hydroxyethylhydrazine (HEH) is studied, that is, the reaction of monochloramine on ethanolamine. The formation of HEH is monitored by UV spectrometry, and the influence of temperature and pH is studied. The primary reaction is an SN 2 ‐type mechanism, whereas the main secondary reaction is the oxidation of HEH by monochloramine. This reaction is also monitored by UV spectrometry, and the oxidation product is identified by GC–MS analysis, showing the formation of hydroxyethylhydrazone. The reaction mechanisms and the rate constants were determined, and the results permit establishing the main reactions occurring during HEH synthesis. These reactions were validated in a concentrated medium, with the systematic study of the influence of the molar ratio p ([HEH] 0 /[NH 2 Cl] 0 ) and the final sodium hydroxide concentration and temperature. A comparison is made with the other synthesis process already published, that is, the alkylation of hydrazine by either chloroethanol or epoxide. © 2011 Wiley Peiodicals, Inc. Int J Chem Kinet 43: 331–344, 2011