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The production method of azo compound

An azo compound and manufacturing method technology, applied in organic chemistry methods, chemical instruments and methods, organic chemistry and other directions, can solve the problems of poor production efficiency, time-consuming filtration, large load, etc., to improve production efficiency and improve filterability. , the effect of reducing the load

Active Publication Date: 2018-09-11
KONISHI CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this way, in the conventional method, transition metals such as copper have a large load on the environment.
In addition, the products obtained by these methods are in the form of slurry, and filtration takes time, so the production efficiency is poor

Method used

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  • The production method of azo compound
  • The production method of azo compound
  • The production method of azo compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0129] Under a nitrogen stream, 90.00 g (0.60 mol) of 4'-aminoacetanilide (A-1) (manufactured by Tokyo Chemical Industry Co., Ltd.) and 540.0 g of acetic acid were added to a jacketed 1-liter separable flask equipped with a stirrer. Kanto Chemical Co., Ltd.) and 1 mL of a transition metal compound aqueous solution prepared by dissolving 0.26 g of anhydrous ferric chloride (C-1) (manufactured by Kishida Chemical Co., Ltd.) in 1000 g of ion-exchanged water. The inside was stirred at 250 rpm. The temperature was increased to 68°C.

[0130] Next, 221.35 g (1.14 mol) of 17.5% by weight hydrogen peroxide aqueous solution (B-1) was added dropwise using a dropping funnel over 1.5 hours [diluted with ion-exchange water 30% by weight hydrogen peroxide aqueous solution (manufactured by Sigma-Aldrich)] .

[0131] After the dropping, the reaction was carried out at an internal temperature of 68°C for 7.5 hours.

[0132] After the reaction, cooling water was circulated in the jacket, and the int...

Embodiment 2

[0138] Except having changed the usage-amount of the anhydrous iron chloride (C-1) of Example 1 to 0.53 g, the same operation as Example 1 was performed.

[0139] The obtained wet cake was 122.00 g, the solid content was 46.5% by weight, and the N,N'-diacetyl-4,4'-diaminoazobenzene (D-1) was 93 area% by HPLC analysis.

[0140] The dry weight (W) of the filter cake was 0.057 kg, and α was calculated according to the above-mentioned method for measuring the filtration resistance. The results are shown in Table 1.

Embodiment 3

[0142] Except having changed the usage-amount of the anhydrous iron chloride (C-1) of Example 1 to 1.04g, the same operation as Example 1 was performed.

[0143] The obtained wet cake was 134.63 g, solid content was 39.0% by weight, and N,N'-diacetyl-4,4'-diaminoazobenzene (D-1) was 95 area% by HPLC analysis.

[0144] The dry weight (W) of the filter cake was 0.053 kg, and α was calculated according to the above-mentioned method for measuring the filtration resistance. The results are shown in Table 1.

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Abstract

A process for producing an azo compound (D) comprising a step of reacting more than one amino compound (A) represented by a formula (1) with an oxygen compound (B) in the presence of a metal component (C), wherein the oxygen compound (B) is at least one selected from a group consisting of hydrogen peroxide, an alkali metal salt of hydrogen peroxide, an alkaline earth metal salt of hydrogen peroxide, perborate, an alkali metal salt of perborate, perchloric acid, an alkali metal salt of perchloric acid, persulfuric acid, persulfate, and urea peroxide, the metal component (C) is at least one selected from the group consisting of a transition metal element and a compound containing the same, and the used amount of the metal component (C) relative to 1 mol of amino compound (A) is less than 0.1 mmol. In the formula, Q is a halogen atom, an alkyl group having 1 to 15 carbon atoms or the like, R is a halogen atom, alkyl group having 1 to 15 carbon atoms or the like. Q and R are different. m represents an integer of 0 to 5, and n represents an integer of 0 to 4. The total of m and n is less than 5.

Description

Technical field [0001] The present invention relates to a method for producing azo compounds. Background technique [0002] Azobenzene is an important compound used in many aspects of industry, for example, as a raw material for dyes, pigments, and heat-resistant polymers. [0003] Conventionally, as a method of producing azobenzene, a method using aniline as a starting material has been known (Patent Document 1, Non-Patent Document 1, etc.). For example, Patent Document 1 describes a method of reacting aniline and a copper compound in the presence of molecular oxygen, and Non-Patent Document 1 describes a method of oxidatively coupling an aniline compound using oxygen as an oxidizing agent under a copper catalyst. [0004] In the method described in Patent Document 1, 0.5 mol times or more of aniline is used relative to 1 mol of the copper compound. In Examples, approximately 12 to 35 mol% of the copper compound is used relative to 1 mol of aniline. In the method described in Non-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C245/08C07B43/00
CPCC07B43/00C07C245/08
Inventor 田端惠知丰岛拓也
Owner KONISHI CHEM IND