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Preparation method of chlorophenoxycarboxylic ester

A technology of chlorophenoxycarboxylate and phenoxycarboxylate, which is applied in the field of herbicide preparation, can solve the problems that restrict the healthy and sustainable development of chlorophenoxycarboxylic acid and its esters, solvent loss, increased VOC, and synthetic Problems such as outdated technology, to achieve the effects of easy separation, energy saving, and utilization efficiency improvement

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

AI Technical Summary

Problems solved by technology

The existing process requires the use of a large amount of organic solvents during esterification. After the reaction is completed, the catalyst needs to be washed with water, and finally the solvent needs to be distilled off. This not only produces a large amount of waste water, but also consumes a lot of energy and causes the loss of solvents and increases VOC. S emissions
[0008] The existing synthetic technology of chlorophenoxycarboxylic acid esters is very backward. With the continuous improvement of environmental protection awareness and environmental protection standards, the old and backward technology has seriously restricted the development of the synthetic industry of chlorophenoxycarboxylic acid and its esters. Benign development and sustainable development, it is imminent to develop an advanced synthesis process

Method used

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  • Preparation method of chlorophenoxycarboxylic ester
  • Preparation method of chlorophenoxycarboxylic ester
  • Preparation method of chlorophenoxycarboxylic ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] 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.

[0073] Add 138.47g of 99% isooctyl alcohol and 1.89g of macroporous styrene-based strongly acidic cation exchange resin D001H to the distilled methyl 2,4-dichlorophenoxyacetate as a catalyst, react at 130°C and evaporate to form Alcohol, after the reaction was completed and filtered to obtain 333.23 g of isooctyl 2,4-dichlorophenoxyacetate, the content was 98.6%, and the yield was 98.59% based on methyl phenoxyacetate.

[0074] After testing, the impurity content: 0.04% isooc...

Embodiment 2

[0082]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.

[0083] Add 76.40g of 99% n-butanol and 0.92g of macroporous styrene-based strongly acidic cation exchange resin SQD-65 to the distilled propyl 4-chlorophenoxyacetate as a catalyst, react at 80°C and distill off the resulting Alcohol, after the reaction was completed and filtered to obtain 243.07 g of n-butyl 4-chlorophenoxyacetate, the content was 98.5%, and the yield was 98.64% based on propyl phenoxyacetate.

Embodiment 3

[0085] Add 196.21g 99% methyl phenoxybutyrate (1mol), 1.08g99% titanium tetrachloride and 0.88g 99% 4,4'-thiobis(6-tert-butyl Base-3-methylphenol), feed 157.56g 99% chlorine gas (2.2mol) at 0°C, complete the heat preservation reaction for 30min, distill and collect the cuts at 150-160°C under 1kpa pressure to obtain 2,4 - 264.04 g of methyl dichlorophenoxybutyrate, content 98.8%, yield 99.14% based on methyl phenoxybutyrate.

[0086] Add 74.24g of 99% isobutanol and 2.64g of macroporous styrene-based strongly basic anion exchange resin D201OH to the distilled 2,4-dichlorophenoxybutyrate methyl ester as a catalyst, react and distill at 60°C After the reaction was completed, the resulting alcohol was filtered to obtain 305.67 g of isobutyl 2,4-dichlorophenoxybutyrate with a content of 98.5%, and the yield was 98.64% based on methyl phenoxybutyrate.

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Abstract

The invention provides a preparation method of chlorophenoxycarboxylic ester, 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, the catalyst B has the following structural formula of R1'-S-R2', and the phenoxycarboxylic ester has any structure represented by the formulas I-IV; and S2) carrying out transesterification reaction of chlorophenoxycarboxylic ester and alcohol under the action of a catalyst to obtain long-chain chlorophenoxycarboxylic ester, wherein the alcohol has the molecular formula of R2OH, and R2 is C4-20 alkyl or cycloalkyl. The method improves the yield and purity of chlorophenoxycarboxylic ester by redesigning of the process route and fine screening of the catalysts and the chlorinating agent. The content ofthe obtained chlorophenoxycarboxylic ester can reach 98.5% or more and the yield can reach 98.5% or more.

Description

technical field [0001] The invention relates to the technical field of herbicide preparation, in particular to a preparation method of chlorophenoxycarboxylate. Background technique [0002] At present, the preparation method of chlorophenoxycarboxylate 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 molecules will occur, resul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/307C07C67/03C07C69/708B01J31/26B01J31/30B01J31/38B01J31/04
Inventor 孙国庆侯永生张利国迟志龙胡义山
Owner SHANDONG RUNBO BIOTECH CO LTD