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Process for producing cyclic phenol sulfides

A technology of sulfide and phenolic compounds, which is applied in the field of preparation of cyclic phenol sulfides, and can solve problems such as unsuitable for industrialization and less output of cyclic tetramers

Inactive Publication Date: 2009-09-09
HODOGOYA CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods can prepare a large number of larger ring-shaped products [m=5~9 in the general formula (2)], but the output of ring tetramer becomes less
Moreover, it is not suitable for industrialization because it is divided into two steps: a preparation step of preparing a chain phenol sulfide from a phenol compound, and a preparation step of cyclizing a chain phenol sulfide to prepare a cyclic phenol sulfide.

Method used

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  • Process for producing cyclic phenol sulfides
  • Process for producing cyclic phenol sulfides
  • Process for producing cyclic phenol sulfides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] In a 500ml four-necked flask equipped with a stirrer, a cooling tube, a thermometer and a gas inlet tube, add 45.1 g of 4-tert-butylphenol and 19.2 g of monomeric sulfur (molar ratio to 4-tert-butylphenol: 2 times molar ratio) ) and 6.0 g of sodium hydroxide (molar ratio relative to 4-tert-butylphenol: 0.5 moles), to which 102 g of diphenyl ether was added, and the temperature was raised to 130° C. while stirring in a nitrogen stream, and at 130° C. The reaction was carried out for 1 hour. The temperature was further raised to 170°C, and the reaction was carried out at 170°C for 1 hour. Finally, the temperature was raised to 230°C, and the reaction was carried out at 230°C for 12 hours. During this period, the generated water and hydrogen sulfide were discharged out of the system by flowing nitrogen gas in the reactor, and were removed by contacting and absorbing the aqueous solution of sodium hydroxide, and the reaction was carried out simultaneously. The reaction mi...

Embodiment 2

[0044] Under the conditions of Example 1, the cyclization reaction and neutralization with sulfuric acid aqueous solution were also carried out, and 79.1 g of methanol was added to the resulting neutralized reaction mixture, then the temperature was raised to 55 ° C, stirred for 1 hour, and the general formula (2) was precipitated. R1 is a tert-butyl group, and m is a coarse crystal of a cyclic tetramer of 4. The crude crystals obtained by filtering the crude crystals under reduced pressure were washed with 80 g of methanol and then with 80 g of water. The obtained cyclic tetramer was 40.2 g, and the yield was a high yield of 74.4% based on 4-tert-butylphenol. As a result of HPLC analysis, the purity was 98.2% in peak area ratio.

[0045] The structure of the resulting cyclic tetramer was identified by IR measurement. IR (liquid paraffin, nujol) cm -1 : 3243, 1475, 1407, 1393, 1267, 1246, 886, 823, 740.

[0046] Next, the above-mentioned cyclic tetramer was filtered under ...

Embodiment 3

[0049] A cyclic phenol sulfide was prepared in the same manner as in Example 1, except that the molar ratio of monomeric sulfur to 4-tert-butylphenol was changed to 2.5 times molar. As a result, a mixture having a peak area ratio of cyclic tetramer of 95.1% and a peak area ratio of cyclic octamer of 4.1% was obtained.

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Abstract

The invention provides a process in which a mixture of cyclic phenol sulfides is produced from inexpensive raw materials through one step without lowering the yield of a cyclic tetramer and a single ingredient can be easily separated from the mixture and purified to thereby produce a larger cyclic reaction product in a large amount. The process for cyclic phenol sulfide production comprises reacting, in one step, a phenol compound as a raw material with 1.7-2.5 mol of elemental sulfur and 0.25-0.75 mol of an alkali metal reagent per mol of the phenol compound to obtain a mixture comprising a cyclic phenol sulfide in which m is 4 and at least one cyclic phenol sulfide in which m is 5-9 or to obtain the individual cyclic phenol sulfides constituting the mixture.

Description

technical field [0001] The present invention relates to a preparation method of a cyclic phenol sulfide, which can be used as: a metal capture agent (capture agent) or a curing agent utilizing the ability to capture metal ions; a photosensitive agent utilizing the ability to recognize ions or molecules Sensors, ion sensors, matrix-specific sensors; separation membrane materials and their intermediates, charge control agents, catalysts, etc. Background technique [0002] The production method of cyclic phenol sulfide includes a method of synthesizing by heating reaction using a phenolic compound, monomeric sulfur, and an alkali metal reagent as raw materials (for example, refer to Patent Documents 1 and 2 and Non-Patent Document 1). These methods use cheap raw materials and obtain the target product through a one-step reaction operation, so they are simple and practical preparation methods, but the distribution of products tends to be biased towards cyclic tetramers [m=4 in t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D341/00C09K3/00
CPCC07D341/00C07D339/00C07D337/02
Inventor 安村正照青木良和伊藤雅美梅川雅文樽本直浩
Owner HODOGOYA CHEMICAL CO LTD
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