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Process for production of oxidized cyclic phenol sulfide

A technology of sulfide and oxidation type, applied in the direction of organic chemistry, organic chemistry, etc., can solve the problems of undeveloped preparation methods and industrial application of compounds, and achieve the goal of improving production efficiency, shortening reaction time, and reducing environmental load Effect

Active Publication Date: 2010-01-27
HODOGAYA KAGAKU IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] However, an industrial-scale production method that is environmentally friendly and highly productive has not yet been developed, and it is still in a situation where it is difficult to link it to the industrial application of this compound

Method used

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  • Process for production of oxidized cyclic phenol sulfide
  • Process for production of oxidized cyclic phenol sulfide
  • Process for production of oxidized cyclic phenol sulfide

Examples

Experimental program
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Effect test

Embodiment 1

[0034] The analysis of the purity and composition ratio of the oxidized cyclic phenol sulfide prepared by the method of the present invention is carried out by high performance liquid chromatography (hereinafter referred to as HPLC), and the structure analysis is carried out by LC / MS measurement. The measurement conditions of HPLC are as follows. Apparatus: LC-10A manufactured by Shimadzu Corporation, Column: Develosil ODS-HG-5 manufactured by Nomura Chemical Co., Ltd. (inner diameter: 4.6 mm, column length: 250 mm), column temperature: 40°C, mobile phase: tetrahydrofuran / acetonitrile / water / trifluoroacetic acid=350 / 350 / 300 / 2 (v / v / v / v), flow rate: 1.0 ml / min, injection volume: 1 μL, sample concentration: 1000 ppm. The measurement conditions of LC / MS are as follows. (1) HPLC measurement conditions, device: Waters Co., Ltd. 2695, column: Shiseido Co., Ltd. Kapselpack C18ACR (5 μm, inner diameter 4.6 mm, column length 250 mm), column temperature: 40°C, mobile Phase: tetrahydrof...

Embodiment 2

[0042] Since repeated reproducibility is required to apply the present invention to industry, a reproducibility confirmation experiment was performed under the same conditions as in Example 1. As a result, 174.6 g (86% yield) of an oxidized cyclic phenol sulfide was obtained.

[0043] The obtained oxidized cyclic phenol sulfide was analyzed by LC / MS Figure 5 Total ion chromatogram (TIC) shown. As a result of structural analysis, it was confirmed that oxidized cyclic tetraploid (oxidized cyclic phenol sulfide in general formula (2) where R = tert-butyl, m = 4, and n = 2) and oxidized cyclic octaploid (R = tert-butyl, m = 8, n = 2 oxidized cyclic phenol sulfide in the general formula (2)). The composition ratio determined by HPLC analysis is: the oxidized cyclic tetraploid has a peak area ratio of 90.9%, and the oxidized cyclic octoploid has a peak area ratio of 5.8%.

[0044] In addition, the sodium content in the obtained oxidized cyclic phenol sulfide was 743 ppm.

Embodiment 3

[0046] Under the same conditions as in Example 1, the reproducibility confirmation experiment was carried out on an enlarged scale.

[0047] In a 10L four-necked flask with a stirrer, a cooling tube, and a thermometer, add a cyclic tetraploid in which R is a tert-butyl group and m is 4 in the general formula (1) and R in the general formula (1) is a tert-butyl group, The composition ratio of the cyclic octaploid whose m is 8 is 1298g (1.8 moles) of the above-mentioned cyclic phenol sulfide, 5200g (4 times wt / wt) of acetic acid, and 118.7g (0.36 mol), 122.4 g (0.90 mol) of sodium acetate·trihydrate, and the temperature was raised to 60°C. 2800 g (29 mol) of 35% hydrogen peroxide aqueous solution was added dropwise into the flask through the dropping funnel over about 3 hours.

[0048] After completion of the dropwise addition, the reaction was carried out at 60° C. for 15 hours, then at 70° C. for 2 hours, and then at 80° C. for 3.5 hours. After adding dropwise 187.5 g (1.8 m...

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Abstract

The invention discloses a process for producing an oxidized cyclic phenol sulfide, which comprises oxidizing a cyclic phenol sulfide represented by the general formula (1) as a raw material with an oxidizing agent by using a solvent other than a halogenated hydrocarbon in an amount of not smaller than 2 parts by weight and less than 10 parts by weight relative to 1 part by mass of the cyclic phenol sulfide, thereby producing an oxidized cyclic phenol sulfide represented by the general formula (2), wherein R represents a linear or branched alkyl group having 1 to 6 carbon atoms; and m represents an integer of 4 to 8, wherein R represents a linear or branched alkyl group having 1 to 6 carbon atoms; m represents an integer of 4 to 8; and n represents a number of 1 or 2.

Description

technical field [0001] The present invention relates to a metal scavenger or curing agent utilizing the ability to capture metal ions, an optical sensor utilizing the ability to recognize ions or molecules, an ion sensor, a substrate-specific sensor, a separation membrane material and their intermediates, a charge control agent, a catalyst, etc. Process for the preparation of useful oxidized cyclic phenol sulfides. Background technique [0002] Conventionally, a method of oxidizing a corresponding cyclic phenol sulfide is known as a method for producing an oxidized cyclic phenol sulfide. As the oxidizing agent used in the oxidation reaction, hydrogen peroxide, organic peroxides, peracids, oxyhalides, N-halogen compounds, molecular halogens, oxygen, ozone, nitric acid, inorganic oxides, etc. are known, among which hydrogen peroxide is preferred , molecular halogen, inorganic oxides (sodium perborate, etc.). As a solvent, suitable solvents will change depending on the type o...

Claims

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Application Information

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IPC IPC(8): C07D341/00C07B61/00
CPCC07D341/00C07B61/00
Inventor 安村正照青木良和伊藤雅美梅川雅文樽本直浩
Owner HODOGAYA KAGAKU IND
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