Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1994-09-02
1995-12-12
Lone, Werren B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568383, 568385, 568741, 568768, C07C 3708, C07C 4553
Patent
active
054751578
DESCRIPTION:
BRIEF SUMMARY
This Application is a 371 of PCT 93/01583, Nov. 1, 1993.
1. Technical Field
This invention relates to a process for producing an aromatic hydroxylic compound useful for the production of synthetic resins, agricultural chemicals, dyestuffs or medicines.
2. Background Art
Among a number of processes for industrial production of aromatic hydroxylic compounds, there is known a process in which a hydroperoxide is decomposed in the presence of an acid catalyst. In this process, sulfuric acid has been mainly used as the acid catalyst, however, a variety of acid catalysts have been proposed other than sulfuric acid.
For instance, a process wherein trifluoromethanesulfonic acid is used as the acid catalyst is proposed in Japanese Patent Application Laid-open No. 50-50311. In addition, for instance, the use of an ion exchange resin containing sulfonic acid groups is proposed in U.S. Pat. No. 4,893,995, and the use of a variety of zeolites in European Patent No. 125,065. The use of Lewis acid such as stannic chloride, antimony chloride, sulfur tetrafluoride, silicon tetrafluoride or tungsten hexafluoride is proposed in U.S. Pat. No. 4,267,380, and a further Lewis acid such as boron trifluoride or boron trifluoride etherate in U.S. Pat. No. 4,267,379.
The decomposition of a hydroperoxide in the presence of an acid catalyst provides a ketone as well as an aromatic hydroxylic compound. In general, the decomposition of hydroperoxide having the general formula (I) ##STR2## wherein Ar represents an aromatic hydrocarbon group having a valence of n; and n represents an integer of 1 or 2, produces acetone as the ketone. According to the conventional processes, the thus produced acetone readily reacts with the hydroperoxide as the starting material to by-produce hydroxyacetone. Thus, there arises a problem in the conventional industrial production of aromatic hydroxylic compound and acetone by the decomposition of hydroperoxide in the presence of an acid catalyst.
The first problem is that the yields of the aromatic hydroxylic compound and acetone are small. The second problem is that waste water contaminated with hydroxyacetone is generated as hydroxyacetone is water-soluble. The third problem is that the by-produced hydroxyacetone gets mixed with the resultant aromatic hydroxylic compound to lower its purity.
The invention has been accomplished to solve the above-mentioned problems involved in the conventional processes for production of an aromatic hydroxylic compound and acetone by the decomposition of hydroperoxide in the presence of an acid catalyst, and thus to provide a process which enables the production of an aromatic hydroxylic compound in a high yield with suppression of by-production of hydroxyacetone.
DISCLOSURE OF THE INVENTION
The invention provides a process for producing an aromatic hydroxylic compound by acid decomposition of a hydroperoxide having the general formula (I) ##STR3## wherein Ar represents an aromatic hydrocarbon group having a valence of n; and n represents an integer of 1 or 2, in the presence of an acid catalyst, thereby to provide an aromatic hydroxylic compound having the general formula (II) tetrafluoroboric acid, hexafluorosilicic acid or hexafluorophosphoric acid is used as the acid catalyst.
In the above general formula, Ar represents an aromatic hydrocarbon group having a valence of n; and n represents an integer of 1 or 2.
Accordingly, when n is 1, Ar is, for example, phenyl; an alkyl substituted phenyl such as tolyl, isopropylphenyl, t-butylphenyl or diisopropylphenyl, a phenyl substituted phenyl such as phenylphenyl; an alkoxy or aryloxy substituted phenyl such as methoxyphenyl or phenoxyphenyl; naphthyl; an alkyl substituted naphthyl such as methylnaphthyl or isopropylnaphthyl; or a phenyl substituted naphthyl such as phenylnaphthyl. When n is 2, Ar is, for example, phenylene; an alkyl substituted phenylene such as methylphenylene or isopropylphenylene; naphthylene; an alkyl substituted naphthylene such as methylnaphthylene or isopropylnaphthylene; or a phenyl substituted napht
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Araki Shintaro
Hashimoto Isao
Iwasaki Hiroshi
Mukaiyama Teruaki
Ohno Hiroyasu
Lone Werren B.
Mitsui Petrochemical Industries Ltd.
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