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Process for production of hydroxybenzoic acids

A formic acid compound and a technology for producing hydroxybenzene, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of expensive and high-cost aprotic polar organic solvents, and achieve high yields

Inactive Publication Date: 2006-06-07
UENO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] Moreover, aprotic polar organic solvents are expensive, and their use results in higher costs

Method used

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  • Process for production of hydroxybenzoic acids
  • Process for production of hydroxybenzoic acids

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Feed 1155 g (5.6 mol) of 2,6-di-tert-butylphenol and 154 g (0.8 mol) of 28% sodium methoxide in methanol into a 2 L, stainless steel vessel equipped with a magnetic stirrer, thermometer, pressure gauge and alcohol separator middle. The resulting reaction mixture was heated to 180°C under nitrogen flow. At this temperature, the reaction was allowed to proceed for 5 hrs while distilling off the by-product, methanol. The resulting slurry of the sodium salt of 2,6-di-tert-butylphenol was heated to 210°C, and the nitrogen in the vessel was replaced with carbon dioxide. At a carbon dioxide pressure of 6kgf / cm 2 Carboxylation under (G) while stirring for 2 hr. After the reaction was completed, the reaction mixture was cooled to 90° C., and 1200 g of water was added thereto. The resulting mixture was heated to 85°C, and the mixture was separated into an aqueous layer and a solvent layer.

[0044] To the thus obtained aqueous layer was added a 73% sulfuric acid aqueous solu...

Embodiment 2

[0046] To the solvent layer separated from the aqueous layer in Example 1, 138 g (0.67 mol) of 2,6-di-tert-butylphenol and 154 g (0.8 mol) of 28% sodium methoxide in methanol were added. In the same manner as in Example 1, 173 g of 3,5-di-tert-butyl-4-hydroxybenzoic acid was obtained. The yield was 87% based on the amount of sodium methoxide fed.

[0047] This demonstrates that excess phenolic compounds can be reused as starting material for the process of the invention.

Embodiment 3

[0049] Using the same method as in Example 1, except that the reaction of 2,6-di-tert-butylphenol with sodium methoxide was carried out at 120° C., 164 g of 3,5-di-tert-butyl-4-hydroxybenzoic acid was obtained. The yield was 82% based on the amount of sodium methoxide fed.

[0050] This demonstrates that the hydroxybenzoic acid compound was obtained in high yield even if the reaction was carried out at a lower temperature.

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Abstract

The present invention provides a method for producing a hydroxybenzoic acid compound, comprising: preparing an alkali metal salt of a phenolic compound from a phenolic compound, and reacting the resulting alkali metal salt of a phenolic compound with carbon dioxide, wherein, preparing from a phenolic compound The step of the alkali metal salt of the phenolic compound comprises the steps of: a) reacting an alkali metal alkoxide with an excess of the phenolic compound, the phenolic compound being in excess of the alkali metal alkoxide, to form an alkali metal salt of the phenolic compound; and b) While carrying out step a), the alcohol formed is distilled off from the reaction. The method of the present invention can produce hydroxybenzoic acid compound with high yield without using aprotic polar organic solvent.

Description

technical field [0001] The present invention relates to a method for producing hydroxybenzoic acid compounds. Background technique [0002] Hydroxybenzoic acid compounds having a substituent such as an alkyl group are used in the manufacture of various materials, for example, UV absorbers and antioxidants for polymer materials such as those used for polypropylene, and for development of pressure-sensitive recording paper pesticides and agricultural chemicals. [0003] As a method for producing hydroxybenzoic acid compounds, the Körber-Schmidt reaction, which involves reacting an alkali metal salt of a phenolic compound with carbon dioxide, has conventionally been used. The starting materials for this reaction, alkali metal salts of phenolic compounds, are traditionally prepared by using alkali metal compounds such as alkali metal hydroxides, alkali metal carbonates, and the like. The reaction of the phenolic compound and the alkali metal compound causes the generation of w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/15C07C65/03
CPCC07C51/15C07C65/03
Inventor 上野隆三北山雅也大塚良一白井健
Owner UENO PHARMA CO LTD
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