Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2001-11-13
2003-12-16
Barts, Samuel (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S844000, C568S910000, C502S102000, C502S120000
Reexamination Certificate
active
06664430
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a method for preparing a fluorine-containing alcohol compound and a catalyst used in the preparation method.
BACKGROUND ART
Japanese Unexamined Patent Publication No. 1992-506507 suggests a method for preparing a fluorine-containing alcohol having water repellency and oil repellency by treating a halogenated alkyl on a catalyst to convert it into an alcohol. However, this method has the shortcomings of using a gas phase reaction at a temperature as high as 400 to 600° C. and of a low degree of conversion and selectivity.
DISCLOSURE OF INVENTION
A primary object of the present invention is to provide a method for preparing a fluorine-containing alcohol compound without using unusual reagents or solvents under relatively moderate reaction conditions and in a high yield.
The inventors of the present invention conducted extensive research to achieve the above object. Consequently, they found that a fluorine-containing alcohol compound can be prepared at a relatively low reaction temperature and in a high yield by using a catalyst which has an element of a specific group of the periodic table, an ion of such an element, an oxide, hydroxide, salt or the like containing such element(s) supported on a specific complex oxide. The present invention was accomplished based on this finding.
Specifically, the present invention provides the following catalyst for preparing a fluorine-containing alcohol compound and a method for preparing a fluorine-containing alcohol compound.
1. A catalyst for preparing a fluorine-containing alcohol compound, the catalyst having at least one component selected from
(i) at least one element selected from the elements in Group 1B, Group 2B, Group 6A, Group 7A and Group 8 of the periodic table,
(ii) at least one ion of the element of the above (i),
(iii) at least one oxide containing one or more elements of the above (i),
(iv) at least one hydroxide containing one or more elements of the above (i), and
(v) at least one salt containing one or more elements of the above (i),
said component being supported on at least one complex oxide selected from Si—Al complex oxides, Al—P complex oxides and Si—Al—P complex oxides.
2. The catalyst according to item 1 in which the complex oxide is an oxide having a zeolite structure.
3. The catalyst according to item 1 or 2, wherein the component supported on the complex oxide is at least one component selected from ions of elements selected from Cu, Ag, Ni, Co, Fe, Hg and Pd, oxides containing such element(s), hydroxides containing such element(s) and salts containing such element(s).
4. A method for preparing a fluorine-containing alcohol compound represented by formula (II):
Rf—(CH
2
)
n
OH (II)
wherein Rf represents a perfluoroalkyl group or a polyfluoroalkyl group and n is an integer from 1 to 5,
the method comprising the step of reacting water with a halogenated fluorine compound represented by formula (I):
Rf—(CH
2
)
n
X (I)
wherein Rf is as defined in the above, X represents I, Br or Cl and n is as defined in the above, in the presence of the catalyst as defined in any one of the above items 1 to 3.
5. The method according to item 4, wherein the reaction between the halogenated fluorine compound and water is carried out in an atmosphere of an oxygen-containing gas.
6. The method according to item 4 or 5, wherein the reaction is carried out under increased pressure.
7. The method for preparing a fluorine-containing alcohol compound according to item 5, wherein X in formula (I) is I, the method further comprising the step of recovering I
2
produced as a byproduct.
The catalyst for preparing a fluorine-containing alcohol compound for use in the present invention has at least one component selected from
(i) at least one element selected from the elements in Group 1B, Group 2B, Group 6A, Group 7A and Group 8 of the periodic table,
(ii) at least one ion of the element of the above (i),
(iii) at least one oxide containing one or more elements of the above (i),
(iv) at least one hydroxide containing one or more elements of the above (i), and
(v) at least one salt containing one or more elements of the above (i),
said component being supported on at least one complex oxide selected from Si—Al complex oxides, Al—P complex oxides and Si—Al—P complex oxides.
Among these elements, examples of the elements in Group 1B include Cu, Ag and Au, among others; examples of the elements in Group 2B include Zn, Cd and Hg, among others; examples of the elements in Group 6A include Cr, Mo and W, among others; examples of the elements in Group 7A include Mn, Tc and Re, among others; examples of the elements in Group 8 include Ni, Co, Fe, Ru, Rh, Pd, Pt and Ir, among others. These elements may be used singly or in combinations of two or more species.
In the present invention, these elements may be supported, and the ions of these elements, oxides, hydroxides, salts or the like containing one or more of these elements may be also supported. Hereinafter in the present specification, these components may be collectively referred to as active components.
Among the active components, the oxides may be those containing one or more of the above elements, and the valence of the element is not restricted. The hydroxides may be those containing one or more of the above elements, and the valence of the element is not restricted. The ions may be those of the above elements, and the charge number of the ion is not restricted. Examples of the useful salts include sulfates, nitrates, carbonates and the like.
The above-mentioned active components may be used singly or in combinations of two or more species.
Among the above-mentioned active components, preferable are ions of Cu, Ag, Ni, Co, Fe, Hg, Pd and other elements, oxides containing one or more of these elements, hydroxides containing one or more of these elements, salts containing one or more of these elements, etc. The catalyst which uses the active component containing Cu, Ni or the like has high selectivity for the desired product; the catalyst using active component containing Ag allows a reaction at a relatively low temperature; and the catalyst using active component containing Fe exhibits good catalytic activity.
The catalyst of the present invention uses at least one complex oxide selected from Si—Al complex oxides, Al—P complex oxides and Si—Al—P complex oxides as a carrier to support the above-mentioned active component.
Examples of such complex oxides include silica-alumina, synthetic silica-alumina zeolite, natural silica-alumina zeolite, aluminum phosphate, synthetic aluminum phosphate zeolite, synthetic Si—Al—P zeolite (SAPO) and the like.
Using a catalyst having the above-mentioned component supported on at least one complex oxide selected from Si—Al complex oxides, Al—P complex oxides and Si—Al—P complex oxides can improve the degree of conversion of raw material, selectivity of the desired product, etc. in the below-mentioned method for preparing a fluorine-containing alcohol compound. Among these complex oxides, using an oxide having a zeolite structure particularly increases selectivity of alcohol.
The method to support the above active component on the complex oxide is not particularly limited, and may be suitably selected from various conventional support methods depending on the kind of the component to be supported. For example, the sol-gel method, hydrothermal synthesis, impregnation method, co-precipitation method, CVD method (chemical vapor deposition method), ion-implantation method or any other methods may be employed.
For instance, when using SAPO-11 zeolite as a Si—Al—P complex oxide, the above-mentioned active component can be supported on the complex oxide by immersing the zeolite in a solution of a soluble metal compound (e.g., an aqueous solution of copper sulfate or like metal salt) to impregnate the zeolite with the solution, optionally followed by heating. The forms of the complex oxide when immersed in a metal compound solution include, but are not limited to, powders, granules, tablets, honeycomb
Aoyama Hirokazu
Miki Jun
Barts Samuel
Daikin Industries Ltd.
Larson & Taylor PLC
Witherspoon Sikarl A.
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