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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  • Abstract
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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 be

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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

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Example Embodiment

[0033] Example 1

[0034] The purity and composition ratio of the oxidized cyclic phenol sulfide prepared according to the method of the present invention are analyzed by high performance liquid chromatography (hereinafter referred to as HPLC), and the structure analysis is performed by LC / MS measurement. The measurement conditions of HPLC are as follows. Equipment: LC-10A manufactured by Shimadzu Corporation, Column: Develosil ODS-HG-5 manufactured by Nomura Chemical Co., Ltd. (inner diameter 4.6mm, column length 250mm), 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: 2695 manufactured by Waters Co., Ltd., column: Kapusherpec C18ACR (5μm, inner diameter 4.6mm, column length 250mm) manufactured by Shiseido Co., Ltd., column temperatur...

Example Embodiment

[0041] Example 2

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

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

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

Example Embodiment

[0045] Example 3

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

[0047] In a 10L four-necked flask with a stirrer, a cooling tube, and a thermometer, add the cyclic tetraploid in which R is tert-butyl in general formula (1) and m is 4, and R is tert-butyl in general formula (1), The composition ratio of the cyclic 8-ploid with m of 8 is 95:5, 1298g (1.8mol) of the above-mentioned cyclic phenol sulfide, 5200g (4 times wt / wt) of acetic acid, 118.7g (0.36 of sodium tungstate dihydrate). 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 dropped into the flask through a dropping funnel over about 3 hours.

[0048] After 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 187.5 g (1.8 mol) of 35% (wt / wt) h...

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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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