Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Patent
1998-10-30
2000-01-11
Ambrose, Michael G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
564503, C07D29588, C07C21304
Patent
active
060138017
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a method for producing aminoethylethanolamine, hydroxyethyl piperazine or both these compounds by continuously ethoxylating ethylenediamine, piperazine or a mixture thereof in an excess of ethylenediamine and piperazine. The resulting ethoxylation product flow is then processed by distillation in a distillation plant for processing an amination product flow obtained in the amination of monoethanolamine with ammonia.
It is long since known, for instance from Knorr et al, Ber. 35 (1902), p. 4470, to produce aminoethylethanolamine by reacting ethylene oxide with ethylenediamine at room temperature and in the presence of considerable amounts of water. The reaction is carried out in an excess of ethylenediamine in order to avoid the formation of higher adducts, such as N,N'-bis(2-hydroxyethyl)-ethylenediamine. DE-A-2,716,946 discloses a discontinuous method for producing aminoethylethanolamine by reacting ethylenediamine with ethylene oxide at a temperature of 100-120.degree. C. and in the presence of water in a specially-developed reaction apparatus. Patent Specification SU-A-1,512,967 discloses the production of N,N'-bis(2-hydroxyethyl)-ethylenediamine by ethoxylating ethylenediamine with ethylene oxide in a molar ratio of 1:2 at a temperature of 40-50.degree. C. and in an approximately 20% aqueous solution. This reaction generates a great number of by-products. Patent Publication EP-A-354 993 proposes that amines containing reactive hydrogen atoms are reacted with ethylene oxide and/or propylene oxide at an elevated temperature, conveniently a temperature of 130-180.degree. C., at a pressure above atmospheric and in the absence of any solvent but in the presence of a catalytic amount of alkali metal hydroxide and/or alkali metal alkoxide.
It is known from DE-A-2,013,676 to react, in a first step, ethylenediamine with ethylene oxide in the absence of a catalyst, and to react, in a second step, the formed higher condensation products in the presence of hydrogen (and optionally ammonia) and a hydration catalyst to piperazine, hydroxyethyl piperazine and N-aminoethyl piperazine.
It is further known that the production of ethylenediamine by the amination of monoethanolamine with ammonia inter alia results in minor amounts of ethylenediamine and piperazine substituted with one or more hydroxyethyl groups. The reaction mixture obtained in the amination is then separated by multistep distillation.
There are many difficulties associated with the production of aminoethylethanolamine and hydroxyethyl piperazine. Thus, one problem is that the ethoxylation of ethylenediamine results in the formation of a number of undesirable by-products, such as di-, tri- or tetra(hydroxyethyl)-ethylenediamine which, along with unreacted ethylenediamine and ethylene oxide as well any water present have to be separated from the aminoethylethanolamine, usually by vacuum distillation. The use of water as catalyst results in the formation of a high-boiling azeotrope of ethylenediamine and water, which is difficult to break. The ethoxylation of piperazine results in the formation of not only hydroxyethyl piperazine but also di-(hydroxyethyl)-piperazine. The resulting product mixture is usually separated by vacuum distillation. If use is made of catalysts which wholly or partly are dissolved in the reactants, also these should be removed prior to the processing of the reaction mixture. In reactions above 100.degree. C., ethylene oxide reacts also with the water present to form ethylene glycol, which results in ethylene oxide losses and further separation problems.
The object of the present invention is to produce aminoethylethanolamine and/or hydroxyethyl piperazine in such a manner as to simplify the purification process. Another object of the invention is that the reaction should be carried out continuously, so as to avoid the problems associated with a reaction batchwise. Further objects of the invention are to achieve high yields of the desirable compounds and to enable use of reactants which are not neces
REFERENCES:
patent: 4338443 (1982-07-01), Brennan et al.
patent: 4590223 (1986-05-01), Arai et al.
patent: 5455352 (1995-10-01), Huellmann et al.
Ludwig Knorr und Henry W. Brownadon: Ueber Alkoholbasen aus Aethylendiamin und uber das Aethylenbismorpholin, Dec. 11, 1902 pp. 4470-4473.
Frank Magnus
Koll, deceased Juhan
Akzo Nobel N.V.
Ambrose Michael G.
Mancini Ralph J.
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