Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-07-02
2002-07-16
Trinh, Ba K. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S541000
Reexamination Certificate
active
06420575
ABSTRACT:
BACKGROUND OF THE INVENTION
(1) Field of the Invention
The present invention relates to a method of refining-treating a liquid reaction mixture obtained from an epoxidation reaction of 1,5,9-cyclododecatriene. More particularly, the method of the present invention relates to a method of refining-treating a liquid reaction mixture obtained from an epoxidation reaction of 1,5,9-cyclododecatriene with hydrogen peroxide in the presence of a catalyst. The refining-treatment method of the present invention is useful for the production of 1,2-epoxy-5,9-cyclododecadiene usable as an intermediate for laurolactam which is usable as a material for the production of nylon 12.
(2) Description of the Related Art
A method of epoxidizing an olefin compound with hydrogen peroxide is generally well known. For example, various methods of epoxidizing an olefin with hydrogen peroxide in the presence of a catalyst comprising, as examples, a tungsten compound, a quaternary onium salt and a mineral acid are disclosed in Japanese Examined Patent Publication No. 1-33,471 and No. 3-74235, and Japanese Unexamined Patent Publication No. 5-213,919, No. 62-230,778 and No. 62-234,550.
However, none of the above-mentioned publications discloses an industrial treating method for isolating an epoxy compound as a target product from a liquid reaction mixture obtained by an epoxidation reaction of the olefin compound with high safety and with high efficiency.
Usually, as a method of treating a liquid reaction mixture obtained from an epoxidation reaction of the olefin compound with hydrogen peroxide, a method in which an oil phase fraction and an aqueous phase fraction contained in the liquid reaction mixture are separated from each other by using a separator, and the separated oil phase fraction is subjected to distillation to collect the target epoxy compound, is utilized.
In the liquid reaction mixture obtained by an epoxidation reaction of 1,5,9-cyclododecatriene with hydrogen peroxide in the presence of a catalyst comprising a tungsten compound, a quaternary onium salt and a mineral acid, however, the oil phase fraction containing the resultant 1,2-epoxy-5,9-cyclododecadiene and the aqueous phase fraction exhibit a low liquid phase separation property from each other, and a portion of the aqueous phase fraction in several % is mixed with and suspended in the form of a plurality of liquid particles in the oil phase fraction. The portion of aqueous phase fraction suspended in the oil phase fraction is difficult to completely separate from the oil phase fraction, even after the oil phase fraction is left to stand for a long period.
The liquid particles, of the aqueous phase fraction mixed in the oil phase fraction, contain the tungsten compound and the mineral acid for the catalyst and the non-reacted hydrogen peroxide are dissolved therein. Therefore, when the oil phase fraction containing the aqueous phase fraction particles is subjected to distillation, the target product, namely 1,2-epoxy-5,9-cyclododecadiene is undesirably polymerized in the presence of the above-mentioned catalyst, and thus, a disadvantageous decrease in the yield of the target compound occurs.
Further, when the particles of the aqueous phase fraction mixed into the oil phase fraction contain a extremely strong acid compound, for example, phosphotungstic acid (H
3
PW
12
O
40
), a phenomenon that the target 1,2-epoxy-5,9-cyclododecadiene vigorously reacts with the phosphotungstic acid (H
3
PW
12
O
40
) to generate exothermic heat, may be created.
Also, a phenomenon that, in the distillation procedure, the non-reacted hydrogen peroxide and a by-product consisting of organic peroxide compounds which are dissolved in the aqueous phase fraction and the oil phase fraction, are respectively thermally decomposed, may be generated, and thus, the method in which the oil phase fraction of the liquid reaction mixture obtained from the epoxidation reaction of 1,5,9-cyclododecatriene is directly subjected to the distillation is not always safe in industrial practice.
Therefore, it is necessary to deactivate the non-reacted hydrogen peroxide and the residual catalyst compound contained in the oil phase fraction of the liquid reaction mixture and/or to remove them from the oil phase fraction by extraction, before the distillation of the oil phase fraction.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a refining treatment method of a liquid reaction mixture obtained from an epoxidation reaction of 1,5,9-cyclododecatriene with hydrogen peroxide in the presence of a catalyst comprising a tungsten compound, a quaternary onium salt and a mineral acid, to obtain a liquid refined mixture from which the target 1,2-epoxy-5,9-cyclododecadiene can be collected, by distillation with an enhanced safety and with a high yield.
The above-mentioned object can be attained by the method of the present invention.
The refining treatment method of the present invention for a liquid reaction mixture obtained from an epoxidation reaction of 1,5,9-cyclododecatriene with hydrogen peroxide in the presence of a catalyst comprising a tungsten compound, a quaternary onium salt and a mineral acid, containing resultant 1,2-epoxy-5,9-cyclododecadiene, the catalyst, non-reacted hydrogen peroxide and non-reacted 1,5,9-cyclododecatriene, and being phase-separated into an oil phase fraction and an aqueous phase fraction, comprises refining-treating at least the oil phase fraction of the liquid reaction mixture with an aqueous alkali solution, to thereby deactivate and remove the non-reacted hydrogen peroxide and the catalyst contained in at least the oil phase fraction of the liquid reaction mixture.
In the refining treatment method of the present invention, for a liquid reaction mixture obtained from an epoxidation reaction of 1,5,9-cyclododecatriene, the aqueous alkali solution preferably has a pH value of 8 or more.
In the refining treatment method of the present invention, for a liquid reaction mixture obtained from an epoxidation reaction of 1,5,9-cyclododecatriene, in a system of the epoxidation reaction, the 1,5,9-cyclododecatriene contained in the reaction system serves as a reaction medium.
In the refining treatment method of the present invention, for a liquid reaction mixture obtained from an epoxidation reaction of 1,5,9-cyclododecatriene, the refining treatment of the liquid reaction mixture obtained from the epoxidation reaction with the aqueous alkali solution, is preferably controlled so that after the refining treatment, the aqueous phase fraction of the liquid reaction mixture exhibits a pH value of 7.0 or more.
In the refining treatment method of the present invention, for a liquid reaction mixture obtained from an epoxidation reaction of 1,5,9-cyclododecatriene, preferably the oil phase fraction is collected from the liquid reaction mixture obtained from the epoxidation reaction, and the collected oil phase fraction is subjected to the refining treatment with the aqueous alkali solution.
In the refining treatment method of the present invention, for a liquid reaction mixture obtained from an epoxidation reaction of 1,5,9-cyclododecatriene, and preferably after the refining treatment of the liquid reaction mixture obtained from the epoxidation reaction with the aqueous alkali solution is completed, the oil phase fraction is collected from the refining-treated liquid reaction mixture.
The method of the present invention for isolating 1,2-epoxy-5,9-cyclododecadiene comprises distilling the oil phase fraction collected and then refining-treated, or refining-treated and then collected, in accordance with the refining treatment method as mentioned above.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The refining treatment method of the present invention for the liquid reaction mixture obtained from the catalytic epoxidation reaction of 1,5,9-cyclododecatriene with.hydrogen peroxide will be explained in detail as follows.
The tungsten compounds usable for the epoxidation catalyst for the epoxidation reaction are preferably selected from inorganic acids
Kaiso Kohji
Kugimoto Junichi
Ninomiya Kouhei
Sugimoto Tsunemi
Yamanaka Mitsuo
Morgan & Lewis & Bockius, LLP
Trinh Ba K.
Ube Industries Ltd.
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