Process for the production of N, N, N′,...

Details Process for the production of N, N, N′,... Process for the production of N, N, N′,...

1999-07-08

2001-04-24

Barts, Samuel (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

Reexamination Certificate

active

06222075

ABSTRACT:

DESCRIPTION
The invention relates to a process for the production of N,N,N′,N′-tetra-(2-hydroxyethyl)-ethylene diamine (=THEEDA) by reacting ethylene diamine with ethylene oxide in a solvent.
A method is known from publication DE-AS 1 020 347, in which alkylene diamines with between 2 and 6 carbon atoms, e.g., ethylene diamine, are reacted with propylene oxide in the presence of water or an alcohol as a conversion catalyst at a temperature of between 40 and 200° C. and preferably between 40 and 120° C., in a molar ratio of 1:4. The reaction produces almost quantitative yields, and these are not even dependent on whether an excess of propylene oxide has been used or not, since the tetraoxypropylated alkylene diamines do not react further with excess propylene oxide under the specified reaction conditions.
In publication DE-AS 1 020 347, it is emphasised that unlike tetraoxypropylated ethylene diamine, the N,N,N′,N′-tetra-(2-hydroxyethyl)-ethylene diamine produced by Sherlin and others in accordance with Chemical Abstracts 35, 5858 (1941) decomposes on heating and cannot be distilled. The production of this product, which is, however, encumbered with diverse by-products, is carried out here by leaving ethylene diamine and ethylene oxide to stand in an aqueous solution for four hours and then removing the water by vacuum. The reaction products have the consistency of a thick oil.


REFERENCES:
patent: 2884459 (1959-04-01), Kirkpatrick et al.
patent: 5846453 (1998-12-01), Mohr et al.
patent: 1020347 (1957-12-01), None
patent: 44 35 688 A1 (1996-04-01), None
patent: WO 90/03964 (1990-04-01), None
Chem. Abstracts, vol. 35, No. 1, 1941.*
Chemical Abstracts, vol. 35, No. 1, XP-002064711, 1941.

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