Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1997-10-20
2000-07-11
Padmanabhan, Sreeni
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568621, 568672, 568699, C07C 4311
Patent
active
060875399
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to a process for producing a vinyl ether polymer having a terminal ether group with a good yield without causing corrosion of the apparatus used for the reaction by hydrogenolysis of a vinyl ether polymer having a terminal acetal group in the presence of a catalyst comprising nickel and specific inorganic oxides.
The ether compound produced by the process of the present invention is advantageously used for solvents, adhesives, resins, organic intermediate materials, lubricating oils, insulating oils, and surfactants.
PRIOR ART OF THE INVENTION
As the process for producing an ether from an acetal, for example, a process using a combination of an acid and an alkali metal hydride, a process using a silicon reagent, and a process using diborane, are described in Jikken Kagaku Koza, Volume 20 (the fourth edition, published by Maruzen). However, these processes are not preferred as an industrial process because a stoichiometric amount of an expensive reagent, such as an alkali metal hydride, a silicon reagent, or diborane, is used as the reagent for the hydrogenolysis, and cost of the production is high.
An ether can be produced from an acetal also by catalytic hydrogenolysis in the presence of an acid catalyst. W. L. Howard et al. reported that an ether could be synthesized by catalytic hydrogenolysis of a ketal by using a catalyst containing rhodium supported on alumina in the presence of hydrochloric acid [J. Org. Chem., 26, 1026 (1961)].
As another example of the process for producing an ether from an acetal, a process for producing an ether by catalytic hydrogenolysis of an acetal compound or a ketal compound in the presence of a catalyst in which (1) a halide of an element of the IIIA group of the Periodic Table (aluminum trichloride or boron trifluoride) and (2) platinum or rhodium are supported on a support, is disclosed in Japanese Patent Application Laid-Open No. Showa 54(1979)-135714.
As still another example of the process, a process for producing a glycol ether by hydrogenolysis of a 1,2-alkyl-1,3-dioxorane in the presence of palladium and phosphoric acid or an ester of phosphoric acid is disclosed in Japanese Patent Application Laid-Open No. Showa 58(1983)-189129.
However, when the apparatus used for the reaction is made of an ordinary material, these processes has a problem that corrosion of the apparatus takes place because an acidic cocatalyst, such as hydrochloric acid, aluminum trichloride, boron trifluoride, and phosphoric acid, is used. A complicated step is also necessary for removing the cocatalyst from the product. Therefore, these processes are not advantageous.
A process for producing an ether from an acetal by hydrogenolysis in the absence of an acid catalyst is also known. A process for producing a dialkyl glycol ether by hydrogenolysis of a formal of a glycol ether in the presence of a catalyst comprising nickel, cobalt, or copper is disclosed in Japanese Patent Application Laid-Open No. Showa 51(1976)-36106.
A process for producing a dialkyl glycol ether by hydrogenolysis of an acetal in the presence of a catalyst comprising nickel, molybdenum, and/or rhenium is disclosed in Japanese Patent Application Laid-Open No. Showa 56(1981)-71031.
In a report cited by M. Verzele et al. in their report [J. Chem. Soc., 5598 (1963)], an ether is produced by hydrogenolysis of an acetal in the presence of a nickel-kieselguhr catalyst. However, this process relates to hydrogenolysis of a low molecular weight acetal.
In the processes described above, the object compound is a low molecular weight compound. No process for producing a vinyl ether polymer having a terminal ether group by hydrogenolysis of a vinyl ether polymer having a terminal acetal group is disclosed in the above references.
A process for producing a vinyl ether polymer having a terminal ether group by hydrogenolysis of a vinyl ether polymer having a terminal acetal group is disclosed in U.S. Pat. No. 2,590,598. This process has the object of providing an ether compound represe
REFERENCES:
patent: 2590598 (1952-03-01), Copenhaver
patent: 4479017 (1984-10-01), Ayusawa et al.
Fujita Keiji
Hirao Yoshikazu
Kamimori Shigeru
Ogawa Akihisa
Yamasaki Hirotaka
Idemitsu Kosan Co. Ltd.
Padmanabhan Sreeni
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