Preparation method of bispyribac-sodium intermediate 4,6-dimethoxy-2-melthyl sulfonyl pyrimidine

A technology of methanesulfonylpyrimidine and dimethoxy is applied in the field of efficient preparation of bispyribac intermediate 4,6-dimethoxy-2-methanesulfonylpyrimidine, and can solve the problems of low oxidation efficiency and environmental pollution Difficult to overcome, catalyst can not be recovered and other problems

Inactive Publication Date: 2015-04-29
JIANGSU RUIDONG PESTICIDE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In the above process, the available chlorine content of sodium hypochlorite solution is low (5.2%), and the oxidation efficiency is low; OXONE reagent is only suitable for laboratory preparation; hydrogen peroxide-sodium tungstate catalytic system has high oxidation efficiency and low production cost , but the expensive catalyst cannot be recovered, the oxidation process is non-selective, and the N atom on the pyrimidine ring is easily oxidized to form nitrogen oxides in an oxidizing environment
[0010] The yield of 4,6-dimethoxy-2-methylsulfonylpyrimidine obtained in the prior art is less than 93%, the production cost is difficult to reduce, and the environmental pollution problem in the production process is difficult to overcome

Method used

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  • Preparation method of bispyribac-sodium intermediate 4,6-dimethoxy-2-melthyl sulfonyl pyrimidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Dissolve 10g template triblock surfactant P123 in 500mL 5% HCl solution, stir at high speed,

[0026] Add 37g of aluminum isopropoxide and 325g of ethyl orthosilicate, hydrolyze to prepare a transparent sol, put it into a polytetrafluoroethylene-lined autoclave, crystallize, filter, wash, and dry. The muffle furnace was programmed to raise the temperature at 2 °C / min to 200 °C for 2 h, and at 5 °C / min to 500 °C for 5 h to obtain the Al-SBA-15 catalyst carrier.

[0027] Dissolve 10g of phosphotungstic acid in 30g of water, add 100g of Al-SBA-15 catalyst, impregnate for 12h, dehydrate by rotary evaporation, dry at 120°C for 5h, and roast at 300°C for 5h in a muffle furnace to obtain the supported catalyst of phosphotungstic acid.

[0028] Add 930g acetic acid, 186g 4,6-dimethoxy-2-methylthiopyrimidine, and 18.6g phosphotungstic acid supported catalyst in the reactor, raise the temperature to 50°C, slowly add 340g 30wt% hydrogen peroxide dropwise, TLC tracking After the r...

Embodiment 2

[0030] Dissolve 15g of template triblock surfactant P123 in 600mL of 5% HCl solution, add 225g of aluminum isopropoxide and 242g of tetraethyl orthosilicate under high-speed stirring, hydrolyze to prepare a transparent sol, and put it into a polytetrafluoroethylene liner Autoclave, crystallization, filtration, washing and drying. The muffle furnace was programmed to raise the temperature at 2 °C / min to 200 °C for 2 h, and at 5 °C / min to 500 °C for 5 h to obtain the Al-SBA-15 catalyst carrier.

[0031] Dissolve 5g of phosphomolybdic acid in 20g of water, add 100g of Al-SBA-15 catalyst, impregnate for 12h, spin-evaporate and dehydrate, dry at 120°C for 5h, and roast at 300°C for 5h in a muffle furnace to obtain a phosphomolybdic acid-supported catalyst.

[0032] In the reactor, add 1860g acetic acid, 186g 4,6-dimethoxy-2-methylthiopyrimidine, and 93g phosphomolybdic acid supported catalyst, raise the temperature to 60°C, slowly add 1133g 30wt% hydrogen peroxide dropwise, TLC tra...

Embodiment 3

[0034] Dissolve 11g template tri-block surfactant P123 in 500mL 5% HCl solution, under high-speed stirring, add 76g aluminum isopropoxide and 312g tetraethyl orthosilicate, hydrolyze to prepare a transparent sol, and put it into a polytetrafluoroethylene liner Autoclave, crystallization, filtration, washing and drying. The muffle furnace was programmed to raise the temperature at 2 °C / min to 200 °C for 2 h, and at 5 °C / min to 500 °C for 5 h to obtain the Al-SBA-15 catalyst carrier.

[0035] Dissolve 30g of silicotungstic acid in 50g of water, add 100g of Al-SBA-15 catalyst, impregnate for 12h, spin dehydrate, dry at 120°C for 5h, and bake at 300°C for 5h in a muffle furnace to obtain the supported catalyst of silicotungstic acid.

[0036] Add 1488g acetic acid, 186g 4,6-dimethoxy-2-methylthiopyrimidine, and 55.8g silicotungstic acid supported catalyst into the reactor, raise the temperature to 80°C, slowly add 680g 30wt% hydrogen peroxide dropwise, TLC tracking After the reac...

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Abstract

The invention discloses a preparation method of a bispyribac-sodium intermediate 4,6-dimethoxy-2-melthyl sulfonyl pyrimidine. The aluminum-doped mesoporous silica SBA-15 is taken as a reaction support and a heteropolyacid is supported on the structure of the reaction carrier to serve as a catalyst, hydrogen peroxide is taken as a green oxidizing agent and acetic acid is taken as a solvent, and then 4,6-dimethoxy-2-methylthiopyrimidine is oxidized to prepare the 4,6-dimethoxy-2-melthyl sulfonyl pyrimidine. The probability of pyrimidine ring oxynitridation is greatly reduced by virtue of the steric effect formed by the regular pores inside the SBA-15 and the inactivation effect of lewis acid on the N atoms of the pyrimidine ring, and the selectivity of oxidation is improved. Meanwhile, the heteropolyacid is supported on the mesoporous support and can be reused, and therefore, the emission of three wastes is reduced and the production cost is reduced.

Description

Technical field: [0001] The invention relates to the field of chemical production, in particular to a high-efficiency preparation method of 4,6-dimethoxy-2-methanesulfonylpyrimidine, a bispyribac ether intermediate. Background technique: [0002] Bispyribac, Chinese chemical name: 2,6-bis(4,6-dimethoxypyrimidine-2-oxy)sodium benzoate, jointly developed by Japan Combination Chemical Co., Ltd., Anyuan Industry Co., Ltd. and K·I Research Institute The pyrimidine salicylic acid herbicide, its mechanism of action is to inhibit the activity of acetolactate synthase (ALS) in plants, interfere with cell division, cause plant stop growth, necrosis and plant death, with broad-spectrum, high efficiency, low toxicity Features. 4,6-Dimethoxy-2-methylsulfonylpyrimidine is an important intermediate in the production of bispyribac, which can be condensed with 2,6-dihydroxybenzoic acid under alkaline conditions to produce bispyribac. [0003] In the literature that has been reported so far...

Claims

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Application Information

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IPC IPC(8): C07D239/60
CPCC07D239/60
Inventor 张国平李云峰
Owner JIANGSU RUIDONG PESTICIDE
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