Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2001-06-19
2002-08-27
Shippen, Michael L. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
Reexamination Certificate
active
06441250
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a process for producing a dihydric phenol which comprises oxidizing a monohydric phenol by a peroxide compound in the presence of a ketone and a phosphoric acid.
2. Prior Art
As a process for producing a dihydric phenol by oxidizing a monohydric phenol by a peroxide compound in the presence of a catalyst, there has been known a process as mentioned below. For example, a process in which a reaction is conducted in the presence of a ketone and phosphoric acid using a catalyst such as sulfuric acid is disclosed in Japanese Provisional Patent Publications Nos. 65232/1977 and 65233/1977, etc. Sulfuric acid used in this process as a catalyst has a corrosive property, and therefore, a new catalyst substituting therefor has been desired to be developed. As a catalyst substituting sulfuric acid, for example, there have been descriptions on phosphotungstic acid and silicotungstic acid in Japanese Provisional Patent Publication No. 078843/1977, various kinds of sulfates in Japanese Provisional Patent Publication No. 130727/1975, and a clay mineral in Japanese Provisional Patent Publication No. 142026/1977, respectively. However, a yield of the product based on a peroxide compound is low, so that a development of a catalyst with a further higher activity has been expected.
SUMMARY OF THE INVENTION
An object of the present invention is to develop an acid catalyst with high activity and without a corrosive property in order to provide a process for producing a dihydric phenol with a high yield by oxidizing a monohydric phenol with a peroxide compound in the presence of a ketone and a phosphoric acid.
The present inventors have intensively studied to accomplish the above-mentioned object and as a result, they have found that a dihydric phenol can be obtained with a high yield by using a &bgr;-zeolite which has no corrosive property when a dihydric phenol is produced by oxidizing a monohydric phenol with a peroxide compound in the presence of a ketone and a phosphoric acid.
That is, the present invention is a process for producing a dihydric phenol which comprises oxidizing a monohydric phenol by a peroxide compound in the presence of a &bgr;-zeolite, a ketone and a phosphoric acid.
Also, the present invention is a process for producing a dihydric phenol which comprises oxidizing a monohydric phenol in the presence of a &bgr;-zeolite, a ketone and a phosphoric acid, by feeding a monohydric phenol, hydrogen peroxide, a ketone and a phosphoric acid into a reactor in which a &bgr;-zeolite is charged, to oxidize the monohydric phenol into a dihydric phenol, and delivering the resultant reaction mixture from the reactor.
DESCRIPTION OF THE PREFERRED EMBODIMENT
In the following, the present invention will be explained in more detail.
As the monohydric phenol to be used in the present invention, there may be mentioned, for example, phenol, a monohydric monoalkyl phenol, a monohydric halogenated phenol and a monohydric polyalkyl phenol.
As the alkyl group contained in the monohydric monoalkyl phenol, there may be mentioned a straight or a branched alkyl group having 1 to 6 carbon atoms. A position of the alkyl group is not particularly limited as long as it does not participate in a reaction. As examples of these compounds, there may be mentioned o-, m- or p-cresol, o-, m- or p-ethylphenol, o-propylphenol, p-isopropylphenol, m-butylphenol, p-isobutylphenol, p-t-butylphenol, m-isobutylphenol, p-pentylphenol and p-hexylphenol.
As the halogen atom contained in the monohydric halogenated phenol, there may be mentioned a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. A number and a position of the halogen atoms are not particularly limited as long as they do not participate in a reaction. As examples of these compounds, there may be mentioned o-, m- or p-fluorophenol, o-, m- or p-chlorophenol, o-, m- or p-bromophenol, o-, m- or p-iodophenol, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dichlorophenol, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dibromophenol, 2,3,4-, 2,3,5-, 2,3,6-, 2,4,5-, 2,4,6- or 3,4,5-trichlorophenol.
As the alkyl group contained in the monohydric polyalkyl phenol, there may be mentioned a straight or a branched alkyl group having 1 to 6 carbon atoms. A number and a position of the alkyl groups are not particularly limited as long as they do not participate in a reaction. As examples of these compounds, there may be mentioned 2,3-, 2,4-, 2,5-, 2,6-, 3,5- or 3,4-dimethylphenol, 2,3,4-trimethylphenol, 2,3,5-, 2,3,6- or 3,4,5-trimethylphenol, 2,4,5-trimethylphenol, 2,3,4,5- or 2,3,5,6-tetramethylphenol, 2-ethyl-3-methylphenol, 3-t-butyl-4-methylphenol, 2-isopropyl-5-methylphenol, 2-pentyl-6-methylphenol and 3-hexyl-5-methylphenol.
As examples of the ketone to be used in the present invention, there may be mentioned a monoketone and a diketone. As the monoketone, a noncyclic or cyclic monoketone is mentioned. As the noncyclic monoketone, there may be mentioned, for example, a straight or branched aliphatic monoketone having 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms and an aromatic monoketone. Hydrogen atom of these compounds may be substituted by a halogen atom (a fluorine atom, a chlorine atom, a bromine atom or an iodine atom). A number and a position of the halogen atoms are not particularly limited as long as they do not participate in a reaction.
As the straight aliphatic monoketone, there may be mentioned, for example, acetone, methyl ethyl ketone, 2-pentanone, 3-pentanone, 2-hexanone, 2-heptanone, 3-heptanone, 4-heptanone, 2-octanone, 2-nonanone, 3-decanone, 6-undecanone, 2-tri-decanone, 7-tridecanone, 2-tetradecanone, 2-pentadecanone, 2-hexadecanone, 2-heptadecanone, 3-octadecanone, 4-nonadecanone, 1-chloro-2-propanone, 1-chloro-3-heptanone and 1-bromo-3-heptanone.
As the branched aliphatic monoketone, there may be mentioned, for example, 3-methyl-2-butanone, 3-methyl-2-pentanone, 4-methyl-2-pentanone, 3,3-dimethyl-2-butanone, 2,4-dimethyl-3-pentanone, 6-methyl-2-heptanone, 2,6-dimethyl-4-heptanone and 2,2,4,4-tetramethyl-3-heptanone. As the aromatic monoketone, there may be mentioned, for example, acetophenone, benzophenone, 1-phenyl-3-propanone, 1-phenyl-1-butanone, 1-phenyl-3-butanone, 1-phenyl-3-pentanone and 1,3-diphenyl-2-propanone.
As the cyclic monoketone, there may be mentioned, for example, a cycloalkyl monoketone having 5 to 12 carbon atoms. Hydrogen atoms of these compounds may be substituted by a halogen atom (a fluorine atom, a chlorine atom, a bromine atom and an iodine atom) or by a straight or a branched alkyl group having 1 to 6 carbon atoms. A number and a position of the substitute are not particularly limited as long as they do not participate in a reaction. As examples of these compounds, there may be mentioned cyclopentanone, cyclohexanone, cyclododecanone, 2-chlorocyclohexanone, 2-ethyl-1-cyclopentanone, 2-methyl-1-cyclohexanone.
As the diketone, there may be mentioned a noncyclic or cyclic diketone. As the noncyclic diketone, there may be mentioned, for example, a straight or a branched aliphatic diketone having 5 to 21 carbon atoms, preferably 5 to 12 carbon atoms and an aromatic diketone. Hydrogen atom of these compounds may be substituted by a halogen atom (a fluorine atom, a chlorine atom, a bromine atom or an iodine atom). A number and a position of the halogen atoms are not particularly limited as long as they do not participate in a reaction. As the straight aliphatic diketone, there maybe mentioned, for example, 2,3-butanedione, 2,4-pentanedione and 2,5-hexanedione. As the branched aliphatic diketone, there may be mentioned, for example, 2,5-dimethyl-3,4-hexanedione. As the aromatic diketone, there may be mentioned, for example, 1,2-diphenylethane-1,2-dione.
As the cyclic diketone, there may be mentioned, for example, a cyclic diketone having 5 to 12 carbon atoms. Hydrogen atom of these compounds may be substituted by a halogen atom (a fluorine atom, a chlorine atom, a bromine atom and an iodine atom) or by a straight or branched alkyl group having 1 to
Atoguchi Takashi
Kanougi Tomonori
Yao Shigeru
Shippen Michael L.
UBE Industries Ltd.
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