Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1995-06-15
1998-01-20
Cintins, Marianne M.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568722, C07C 3916
Patent
active
057103461
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP94/01775 which was filed on Oct. 21, 1994.
TECHNICAL FIELD
The present invention relates to a novel 2,2-bis(3,5-disubstituted-4-hydroxyphenyl)propane derivative, a process for production thereof, and a process for producing pyrogallol using the propane derivative.
More particularly, the present invention relates to a 2,2-bis(3,5-disubstituted-4-hydroxyphenyl)propane derivative which has by itself a periphyton (e.g., marine fouling organism)-controlling activity required for the active ingredient used in an antifouling paint for ship's bottom, an antifouling agent for fishing net, or the like and which also is useful as a material for pyrogallol production; a process for producing the propane derivative industrially; and a process for producing pyrogallol industrially by using the propane derivative.
BACKGROUND ART
The 2,2-bis(3,5-disubstituted-4-hydroxyphenyl)propane derivative provided by the present invention is a novel compound which is not described in any literature, and it has been unknown that the compound has by itself a periphyton-controlling activity and also can be used as a suitable material for industrial production of pyrogallol.
Up to this time, pyrogallol has been produced by heating gallic acid in an autoclave at 200.degree.-210.degree. C. for 30 minutes and subjecting the resulting product to decoloring, filtration and vaporization. This process has not been satisfactory as an industrial process, for example, because the raw material is a natural product, is difficult to procure stably, and is expensive.
The objects of the present invention are to provide a novel 2,2-bis(3,5-disubstituted-4-hydroxyphenyl)propane derivative, a process for production thereof, and a process for producing pyrogallol using the propane derivative.
The present inventors made an extensive study in order to provide a useful and novel 2,2-bis(3,5-disubstituted-4-hydroxyphenyl)propane derivative and a process for production thereof. As a result, the present inventors found out that the 2,2-bis(3,5-disubstituted-4-hydroxyphenyl)propane derivative can easily be obtained by reacting a 2,2-bis(3,5-dihalogeno-4-hydroxyphenyl)propane (this is easily available) with a metal alkoxide.
The present inventors further found out that the above propane derivative has by itself a periphyton-controlling activity required for the active ingredient used in an antifouling paint for ship's bottom, an antifouling agent for fishing net, or the like and also that by decomposing the propane derivative with an alkali or an acid, pyrogallol can be obtained easily. The present invention has been completed based on the above finding.
DISCLOSURE OF THE INVENTION
The present invention provides: represented by general formula (1) ##STR2## wherein each R.sup.1 represents a hydrogen atom or a lower alkyl group, alkoxy)-4-hydroxyphenyl!propane derivative, which is characterized by reacting a 2,2-bis(3,5-dihalogeno-4-hydroxyphenyl) propane derivative represented by general formula (2) ##STR3## wherein each X represents a halogen atom, with a metal alkoxide represented by general formula (3) metal or an alkaline earth metal, and n represents an integer of 1 or 2, alkoxy)-4-hydroxyphenyl!propane, and decomposing, with an alkali or an acid, a 2,2-bis(3,5-disubstituted-4-hydroxyphenyl)propane derivative represented by general formula (1) ##STR4## wherein each R.sup.1 has the same definition as given above.
The term "lower" used in the present specification refers to that the compound or substituent appearing after the term has 1-4 carbon number.
The present invention is described in detail below
Specific examples of the 2,2-bis(3,5-disubstituted-4-hydroxyphenyl)propane derivative, which is the present compound represented by general formula (1), include compounds of general formula (1) wherein each substituent alkoxy)-4-hydroxyphenyl!propanes. They are more specifically compounds of general formula (1) wherein each of the 3-and 5-positions of the phenyl rings is substituted with an alkoxy group of 1-4 carbon nu
REFERENCES:
patent: 4716252 (1987-12-01), Wagner et al.
patent: 4814520 (1989-03-01), Nakagawa
Abstract to Hosaka et al., EP 211667 A2, Feb. 25, 1987.
Kimura Yoshikazu
Maejima Chika
Miyazaki Tomonori
Takahashi Masakazu
Cintins Marianne M.
Ihara Chemical Industry Co. Ltd.
Jones Dwayne C.
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