Preparation method of chlorophenoxycarboxamide salt

A technology of chlorinated phenoxycarboxylic acid amine salt and chlorophenoxycarboxylic acid ester, which is applied in the field of herbicide preparation, can solve problems such as environmental hazards, loss of active ingredients, and high pressure of three wastes treatment, so as to improve production capacity and increase Utilization efficiency and energy saving effects

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

In this step, the dioxins contained in the chlorophenoxycarboxylic acid will enter into the chlorophenoxycarboxylic acid amine salt, and enter the plants, air, soil and water with the use of the chlorophenoxycarboxylic acid amine salt, And with the enrichment of the food chain, it will cause more serious environmental hazards
[0006] In the above-mentioned preparation process, the chlorination selectivity is poor, and the post-treatment process will cause the loss of active ingredients, and the yield of the product is low
At the same time, when phenol is used as a raw material to synthesize chlorinated phenoxycarboxylic acid through chlorination and condensation, a large amount of waste water containing hydroxycarboxylic acid and waste salt will be produced, and a large amount of hazardous waste containing chlorophenol and chlorophenoxycarboxylic acid wi

Method used

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  • Preparation method of chlorophenoxycarboxamide salt
  • Preparation method of chlorophenoxycarboxamide salt
  • Preparation method of chlorophenoxycarboxamide salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Add 167.87g 99% methyl phenoxyacetate (1mol), 1.26g 99% zinc chloride and 1.68g 99% 2,4,6-trimethyldiphenylsulfide successively in a 500mL four-necked bottle, at - 154.69g of 99% chlorine gas (2.16mol) was introduced at 20°C, and the heat preservation reaction was completed for 30 minutes, and the distilled under 1kpa pressure and collected fractions at 140-150°C to obtain 236.21g of methyl 2,4-dichlorophenoxyacetate , the content is 98.8%, and the yield is 99.28% based on methyl phenoxyacetate.

[0065] After testing, the impurity content is as follows: 0.03% of methyl 4-chlorophenoxyacetate, 0.09% of methyl 2,6-dichlorophenoxyacetate, 0.16% of methyl 2,4,6-trichlorophenoxyacetate, The content of 2,4,6-trimethyldiphenylsulfide is 0.13%.

[0066] Add 118.63g of 40% dimethylamine to the distilled 2,4-dichlorophenoxyacetic acid methyl ester, react at 130°C and distill off the generated alcohol to obtain 2,4-dichlorophenoxyacetic acid dimethylamine Salt 319.14g, content ...

Embodiment 2

[0074] Add 196.21g 99% propyl phenoxyacetate (1mol), 0.29g 99% ferric chloride and 0.69g 99% 2-methyldiphenylsulfide successively in a 500mL four-necked flask, add 137.70 g 99% sulfuryl chloride (1.01mol), after the dropwise addition, keep the temperature for 30 minutes, distill and collect the fraction at 145-155°C under the pressure of 1kpa to obtain 229.01g of propyl 4-chlorophenoxyacetate, the content is 98.9%, the yield 99.04% based on propyl phenoxyacetate.

[0075] Add 129.51g of 40% dimethylamine to the distilled propyl 4-chlorophenoxyacetate, react at 120°C and distill off the resulting alcohol to obtain 291.58g of dimethylamine 4-chlorophenoxyacetate with a content of 78.4 %, the yield is 98.64% based on propyl phenoxyacetate.

[0076] Adopt nuclear magnetic resonance to detect the propyl 4-chlorophenoxyacetate of preparation, the results are shown in figure 1 , figure 1 Propyl NMR spectrum of 4-chlorophenoxyacetate.

Embodiment 3

[0078] Add 196.21g 99% methyl phenoxybutyrate (1mol), 1.08g99% titanium tetrachloride and 0.88g 99% 2,4,6-trimethyldiphenylsulfide successively in a 500mL four-necked flask, 157.56g of 99% chlorine gas (2.2mol) was introduced at 0°C, and the heat preservation reaction was completed for 30 minutes. Distilled at a pressure of 1kpa and collected at 150-160°C to obtain methyl 2,4-dichlorophenoxybutyrate 264.04g, content 98.8%, yield 99.14% based on methyl phenoxybutyrate.

[0079] Add 72.94g of 25% ammonia water to the distilled methyl 2,4-dichlorophenoxybutyrate, react at 100°C and distill off the resulting alcohol to obtain 2,4-dichlorophenoxybutyric acid ammonium salt 303.00 g, the content is 86.7%, and the yield is 98.74% based on methyl phenoxybutyrate.

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Abstract

The invention provides a preparation method of chlorophenoxycarboxamide salt, wherein the preparation method includes the following steps: S1) carrying out 2-site and/or 4-site selective chlorinationreaction of phenoxycarboxylic ester with a chlorinating agent under the action of a catalyst A and a catalyst B to obtain chlorophenoxycarboxylic ester, wherein the catalyst A is Lewis acid, and the catalyst B has the following structural formula of R1'-S-R2'; and S2) carrying out ammonolysis reaction of chlorophenoxycarboxylic ester and amine to obtain chlorophenoxycarboxamide salt. By redesigning of the process route and fine screening of the catalysts and the chlorinating agent, the method reduces energy consumption, improves chlorination selectivity and avoids loss of effective components.The yield of the obtained chlorophenoxycarboxamide salt can reach 98.5% or more. At the same time, the production of high-salt wastewater is completely eradicated, the dust hazard caused by drying and use of chlorophenoxycarboxylic acid is avoided, energy is saved and equipment investment is reduced.

Description

technical field [0001] The invention relates to the technical field of herbicide preparation, in particular to a preparation method of chlorophenoxycarboxylate amine salt. Background technique [0002] At present, the preparation method of chlorophenoxy carboxylic acid amine salt mainly comprises the following steps: [0003] 1) Using phenol as the main raw material, chlorinated phenols are obtained through chlorination. The chlorophenol produced in this step has an extremely unpleasant pungent odor, which leads to a very poor production site environment and poor chlorination selectivity. [0004] 2) Chlorophenol is condensed with chlorinated carboxylic acid under alkaline conditions, and the reaction solution is acidified and filtered to obtain chlorophenoxycarboxylic acid wet material, which is dried to obtain chlorophenoxycarboxylic acid. During the condensation process of the dichlorophenol or polychlorophenol in the chlorophenol in this step, condensation between two ...

Claims

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Application Information

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IPC IPC(8): C07C51/41C07C209/00C07C59/70C07C59/68C07C211/04C07C211/06C07C211/07
Inventor 孙国庆侯永生张利国迟志龙胡义山
Owner SHANDONG RUNBO BIOTECH CO LTD
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