Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-02-15
2002-07-02
Ramsuer, Robert W. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S546000
Reexamination Certificate
active
06414169
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a method of producing an epoxycyclododecane compound. More particularly, the present invention relates to a method of producing an epoxycyclododecane compound by catalytically and selectively hydrogenating double bonds of 1,2-epoxy-5,9-cyclododecadiene.
An epoxycyclododecane compound is useful for producing not only a resin component for paints and adhesives, but also a lactam compound, a lactone compound or a dibasic carboxylic acid through a cyclododecanone derived from the epoxycyclododecane by a conventional method and, thus, it is an important intermediate for polyamide 12 and polyesters which are useful materials for producing synthetic resins and synthetic fibers.
2. Description of the Related Art
It is known to produce an epoxycyclododecane compound by a catalytic reaction of 1,2-epoxy-5,9-cyclododecadiene with hydrogen in the presence of a platinum group metal-containing catalyst.
For example, Soviet Union (SU) Pat. No. 380,650 discloses a method of synthesizing an epoxycyclododecane compound by reducing 1,2-epoxy-5,9-cyclododecadiene with hydrogen in a cyclohexane medium in the presence of a catalytic component comprising a platinum-group metal (a metal of Group VIII of the Periodic Table) carried on a carrier consisting of alumina or activated carbon, at a reaction temperature of 70 to 200° C. under a hydrogen gas pressure of 101,325 to 263,445 kPa (100 to 260 atmospheres). In this method, however, the yield of the target epoxycyclododecane compound was 82 to 95% which was unsatisfactory. Also, this method is disadvantageous in that the necessary amount of the catalyst based on the amount of 1,2-epoxy-5,9-cyclododecadiene fed into the reaction procedure is too high.
Also, “Russian Journal of General Chemistry”, Vol. 67, No. 6 (1997), pages 921 to 926, discloses a result of a reaction of 1,2-epoxy-5,9-cyclododecadiene with hydrogen in the presence of a catalyst comprising a catalytic component comprising a platinum group metal (for example, palladium or platinum) carried on a carrier component comprising an activated carbon, alumina or a silica gel. In an embodiment of the method, the reaction was carried out in the presence of a catalyst in which palladium is carried on a carrier comprising an activated carbon, alumina or a silica gel, at a reaction temperature of 30 to 90° C. under a hydrogen gas pressure of 0.1 to 4.0 MPa, and the target epoxycyclododecane compound was obtained in a yield of 80 to 99%. In another embodiment, the reaction was carried out in the presence of a catalyst in which platinum was carried on a silica gel carrier, at a reaction temperature of 50° C. under a hydrogen gas pressure of 1.3 to 2.5 MPa, and the target epoxycyclododecane compound was obtained in a yield of 84%. This report is, however, quite silent as to the length of the life of the catalyst.
Generally, when a catalyst containing a platinum group metal which is an expensive noble metal is used in industry, it is necessary that the resultant catalyst enables the target product to be produced in a high yield; the catalytic reaction can be effected at a high reaction rate; and the resultant catalyst has a long duration of life.
However, the prior art literature and patent publications did not teach or suggest how to impart a long life to the catalyst.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a method which enables an epoxycyclododecane compound to be industrially produced with a high yield at a high reaction rate, by a reaction of 1,2-epoxy-5,9-cyclododecadiene with hydrogen in the presence of a catalyst with a long life thereof.
The above-mentioned object can be attained by the method of the present invention.
The method of the present invention for producing epoxycyclododecane compound comprises hydrogenating 1,2-epoxy-5,9-cyclododecadiene with a hydrogen gas in the presence of a platinum group metal-containing catalyst,
the hydrogen gas having a pressure of 0.8 to 9 MPa, and
the platinum group metal-containing catalyst being a platinum-containing catalyst.
In the method of the present invention for producing an epoxycyclododecane compound, the hydrogen gas pressure for the hydrogenation is in the range of from 3 to 7 MPa.
In the method of the present invention for producing an epoxycyclododecane compound, the hydrogenation is carried out under a hydrogen gas pressure of 0.8 to 9 MPa at a temperature higher than 50° C.
In the method of the present invention for producing an epoxycyclododecane compound, the platinum containing catalyst is employed in an amount, in terms of platinum, of 0.0005 times or less the molar amount of 1,2-epoxy-5,9-cyclododecadiene.
In the method of the present invention for producing an epoxycyclododecane compound, the platinum-containing catalyst comprises a platinum-containing catalytic component carried on an inert carrier component comprising at least one member selected from activated carbon, alumina, silica, silicaalumina, zeolite, and spinel.
In the method of the present invention for producing an epoxycyclododecane compound, the carrier component for the platinum-containing catalyst consists of activated carbon.
In the method of the present invention for producing an epoxycyclododecane compound, the platinum-containing catalytic component is present in an amount, in terms of platinum, of 0.1 to 10% by weight, based on the weight of the inert carrier component.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The 1,2-epoxy-5,9-cyclododecadiene usable, as a starting material, for the method of present invention can be produced by, for example, epoxidizing a cyclododecatriene with an organic carboxylic acid and hydrogen peroxide. In the resultant 1,2-epoxy-5,9-cyclododecadiene, the epoxy group and the double bond may be located in any of a cis-form, a trans-form or an other form.
For the method of the present invention, a trade 1,2-epoxy-5,9-cyclododecadiene may be employed without refining by distillation, etc., or after refining by distillation, etc. When the compound is a synthetic product, the compound is preferably employed after refining by distillation, etc.
The platinum-containing catalyst usable for the present invention is preferably selected from solid catalysts, preferably particulate solid catalysts, more preferably particulate solid catalyst having an average particle size of several &mgr;m to several hundreds &mgr;m, particularly 10 to 300 &mgr;m, comprising a catalytic component comprising a platinum-containing compound and carried on an inert carrier.
The inert carrier for the catalyst preferably comprises at least one member selected from the group consisting of activated carbon, alumina, silica, silicaalumina, zeolite and spinel, more preferably, activated carbon, alumina and silicaalumina. Still more preferably, the inert carrier is formed from activated carbon.
The platinum-containing catalytic component is preferably present in an amount, in terms of platinum, of 0.1 to 10% by weight, more preferably 0.2 to 8% by weight, based on the weight of the inert carrier component. In the catalyst, the platinum-containing catalytic component may be carried on the surface of and/or inside the inert carrier component.
In the method of the present invention, the specific platinum-containing catalyst exhibits a long life.
In the hydrogenation reaction of the method of the present invention, the platinum-containing catalyst is preferably used in a molar amount in terms of platinum, of 0.0005 times or less, more preferably 0.000001 to 0.0005 times, still more preferably 0.000005 to 0.0004 times the molar amount of 1,2-epoxy-5,9-cyclododecadiene used as a starting material. If the amount of the catalyst is too little, the time necessary to complete the reaction may be too long. Also, the use of the catalyst in too large an amount may cause the yield of the target product to decrease.
In the catalytic reaction of the method of the present invention, a reaction medium is not always necessary. When the reaction medium is used, for example,
Funatsu Joji
Ii Nobuhiro
Kugimoto Junichi
Kuroda Nobuyuki
Nakamura Takato
D'Souza Small Andrea
Morgan & Lewis & Bockius, LLP
Ramsuer Robert W.
Ube Industries Ltd.
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