Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Patent
1987-06-17
1991-08-20
Ford, John M.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
544 82, 544116, C07D48706, C07D40304, C07D41314
Patent
active
050415484
DESCRIPTION:
BRIEF SUMMARY
FIELD OF TECHNOLOGY
This invention relates to a method for the preparation of triethylene diamines or, more particularly, to a method for the preparation of triethylene diamines with good efficiency from an amine compound having, in the molecule, a group represented by the general formula ##STR1## wherein, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each denote a hydrogen atom or an alkyl group having 1 to 4 carbon atoms by using a specific crystalline metal silicate as the catalyst.
BACKGROUND TECHNOLOGY
While, in the prior art, triethylene diamine was prepared from aminoethyl piperazine as the starting material, a method has been developed in recent years to give a high yield from hydroxyethyl piperazine as the starting material using a calcium phosphate-based catalyst (Japanese Patent Kokai 58-17839).
These starting compounds, however, are expensive with low availability so that the above described methods are not suitable for practice.
On the other hand, Japanese Patent Kokai 51-141895 discloses a method for the preparation of triethylene diamine by bringing diethanol amine as the starting material into contact with an alumina catalyst, silica-alumina catalyst or silica-alumina catalyst substituted by metal ions. This method, however, is a two-step process in which an intermediate is prepared in the course thereof and subsequently triethylene diamine is prepared and the yield is low in addition to the troublesomeness of the working procedure.
The present invention has an object to develop a method for the preparation of triethylene diamines in a simple procedure and still in a high yield by use of various kinds of readily available starting compounds overcoming the above described defects in the prior art technology.
DISCLOSURE OF INVENTION
Namely, the present invention provides a method for the preparation of triethylene diamines characterized, in the preparation of triethylene diamines by bringing an amine compound having, in the molecule, a group represented by the general formula ##STR2## wherein, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each denote a hydrogen atom or an alkyl group having 1 to 4 carbon atoms into contact with a catalyst, by using, as the catalyst, a crystalline metal silicate, in which the molar ratio (SiO.sub.2 /M.sub.2 O.sub.3) of silicon dioxide (SiO.sub.2) to the oxide of a tervalent metal (M.sub.2 O.sub.3, M denoting a tervalent metal) is at least 12, formed by the crystallization in the presence or in the absence of an organic crystallizing agent (excepting those crystallized in the absence of an organic crystallizing agent when the tervalent metal is aluminum alone).
The triethylene diamines of the present invention here implied are the compounds represented by the general formula ##STR3## in the formula, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same as above defined.
THE BEST EMBODIMENT TO PRACTICE THE INVENTION
The starting compound used for practicing the method of the present invention may be any of the amine compounds having the group represented by the above given general formula [I] in the molecule including various compounds although it is usually monoethanol amine, isopropanol amine, diethanol amine, diisopropanol amine, triethanol amine, piperazine, N-hydroxyethyl piperazine, N-aminoethyl piperazine, morpholine, ethylene diamine, diethylene triamine, triethylene tetramine or the like.
The crystalline metal silicate used as the catalyst in the method of the present invention is a product by the crystallization in the presence or in the absence of an organic crystallizing agent, of which the crystalline skeleton is composed mainly of silicon dioxide (SiO.sub.2) and an oxide of a tervalent metal (M.sub.2 O.sub.3), while the proportion of them or, namely, SiO.sub.2 /M.sub.2 O.sub.3 (molar ratio) should be at least 12 or, preferably, from 40 to 3000 or, more preferably, from 90 to 500. In this case, the SiO.sub.2 /M.sub.2 O.sub.3 (molar ratio) smaller than 12 is undesirable due to the decrease in the yield of the triethylene diamines.
The crystalline metal silica
REFERENCES:
patent: 2977363 (1961-03-01), Farkas et al.
patent: 3120526 (1964-02-01), Brader
patent: 3956329 (1976-05-01), Murakami et al.
patent: 4289881 (1981-09-01), Imre et al.
patent: 4804758 (1989-02-01), Hoelderich et al.
Sato Haruhito
Tsuzuki Masanori
Ford John M.
Idemitsu Kosan Company Limited
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