Preparation method of phenoxycarboxylic acid substances

A technology for phenoxycarboxylic acids and phenolic compounds is applied in the field of preparation of phenoxycarboxylic acids, and can solve the problems of complex technological process, complicated process and high consumption of sodium chlorocarboxylate

Inactive Publication Date: 2018-12-07
SHANDONG RUNBO BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, this method has the following disadvantages: 1) From the perspective of raw materials, the process uses phenol chlorination to obtain 2,4-dichlorophenol, which has a strong odor and produces highly toxic carcinogen dichlorophenol during condensation. oxins; 2) from the technical process, the process is complex, first chlorination to obtain chlorophenol, and then synthesize sodium phenate, chloroacetic acid configuration neutraliza

Method used

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  • Preparation method of phenoxycarboxylic acid substances
  • Preparation method of phenoxycarboxylic acid substances
  • Preparation method of phenoxycarboxylic acid substances

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[0027] The invention provides a kind of preparation method of phenoxycarboxylic acid substances, comprising:

[0028] S1) mixing the phenolic compound represented by formula (I), the halogenated fatty alcohol represented by formula (II) and alkali metal carbonate in an organic solvent, heating and reacting to obtain phenoxy fatty alcohol;

[0029] S2) reacting the phenoxy fatty alcohol with an oxidizing agent to obtain phenoxy fatty acid;

[0030] S3) Mixing and reacting the phenoxy fatty acid, the chlorination catalyst and the chlorination agent to obtain the phenoxycarboxylic acid substances represented by the formula (III);

[0031]

[0032] Wherein, R is H or C1~C5 alkyl, preferably C1~C3 alkyl, more preferably C1~C2 alkyl, more preferably methyl; R 1 It is H or C1-C4 alkyl, preferably H or C1-C3 alkyl, more preferably H or C1-C2 alkyl; R 2 is Cl or H, and R and R 2 Not simultaneously H; X is halogen, preferably Cl.

[0033] The present invention has no special limi...

Embodiment 1

[0044] Add 97g 98.5% phenol, 81g 99% chloroethanol, 145g 99% potassium carbonate and 300g DMF into the reactor, raise the temperature to 130°C, keep the temperature for 6 hours, cool down to room temperature, then filter to remove the salt, add fresh DMF Wash the filter cake twice, then mix the filtrate to obtain phenoxyethanol after rectification treatment, then add 139.6g (1mol) phenoxyethanol, water 300g, add 14g activated carbon, add 350g 10% hydrogen peroxide, heat up to about 120°C and keep 12 Hours, check the content of phenoxyethanol, when the content of phenoxyethanol is less than 0.1%, cool down to about 80°C, add 1.4g of formamide, and pass in 144g of chlorine gas, the aeration time is controlled at 2 to 5 hours. After the chlorination is completed, cool down , filtered, and dried to obtain 214.1 g of 2,4-dichlorophenoxyacetic acid with a purity of 98.2% and a yield of 95.1%.

Embodiment 2

[0046] Add 97g 98.5% phenol, 81g 99% chloroethanol, 145g 99% potassium carbonate, and 300g DMSO into the reactor, raise the temperature to 150°C, keep it warm for 5 hours, cool down to room temperature, then filter to remove salt, add fresh DMSO to wash Filter the cake twice, then mix the filtrate to obtain phenoxyethanol after rectification treatment, add 139.6g (1mol) of phenoxyethanol, 300g of water, add 28g of white carbon black, pass in 32g of ozone, heat up to about 120°C and keep for 12 hours, Check the phenoxyethanol content, when the phenoxyethanol content is less than 0.1%, wait until it is not qualified. Cool down to about 80°C, add 1.5g of formamide, add dropwise 270g of sulfuryl chloride, and control the dropwise addition time within 2 to 5 hours. After the chlorination is completed, cool down, filter, and dry to obtain 2,4-dichlorophenoxyacetic acid 217.4 g, purity 98.1%, yield 96.6%.

[0047] Utilize high performance liquid chromatography to analyze the 2,4-dic...

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Abstract

The invention provides a preparation method of phenoxycarboxylic acid substances, wherein the preparation method includes the steps: S1) mixing phenol compounds represented by the formula (I) and halogenated fatty alcohols represented by the formula (II) with alkali metal carbonates in organic solvents, carrying out heating reaction to obtain phenoxy fatty alcohols; S2) carrying out reaction of the phenoxy fatty alcohols with oxidants to obtain phenoxy fatty acids; and S3) carrying out mixed reaction of the phenoxy fatty alcohols, a chlorination catalyst and a chlorinating agent to obtain thephenoxycarboxylic acid substances represented by the formula (III). Compared with the prior art, the phenoxy fatty alcohols are obtained with phenolic compounds as the starting raw material, and thenoxidized and chlorinated to obtain the phenoxycarboxylic acid compounds. The method does not need dehydration, is environmentally friendly, has no chlorophenol participation, cannot produce dioxins, solves the problem of large odor, and has high selectivity for directional chlorination. At the same time, the method does not need cumbersome enrichment devices. The whole process is simple, the investment of equipment is low, and the energy consumption is reduced.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of phenoxycarboxylic acid substances. Background technique [0002] At present, phenoxycarboxylic acids are widely used in herbicide pesticides. In 1941, 2,4-dichlorophenoxyacetic acid, the first phenoxycarboxylic acid herbicide, was synthesized. In 1942, it was discovered that the compound had the effect of plant hormones. In 1944, 2,4-dichlorophenoxyacetic acid was discovered. And 2,4,5-T have herbicidal activity on field bindweed. In 1945, the herbicide 2 methyl 4 chlorine was found. The selectivity, conductivity and herbicidal activity displayed by these herbicides became the basis for the subsequent development of herbicides and promoted the development of chemical herbicides. [0003] Phenoxycarboxylic acid herbicides can be divided into two different basic series according to the different compounds of their active ingredients. ...

Claims

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Application Information

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IPC IPC(8): C07C51/363C07C59/70
CPCC07C41/16C07C51/285C07C51/363C07C43/23C07C59/70
Inventor 孙国庆侯永生贺恩静迟志龙胡义山
Owner SHANDONG RUNBO BIOTECH CO LTD
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