Refining method of 2-nitro-4-methanesulfonylbenzoic acid

A technology of methanesulfonyl benzoic acid and purification method, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc. The problem of low purity of sulcotrione original drug, to achieve the effect of easy operation

Inactive Publication Date: 2020-06-19
NUTRICHEM LAB CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] WO2015062103A1, US7285678, etc. pointed out that the raw material impurities of 2-nitro-4-methylsulfonylbenzoic acid were too high, resulting in low purity of the original drug of mesotrione; WO2015062103A1 proposed a 2-nitro-4-methylsulfonylbenzoic acid Refining method, the crude product of 2-nitro-4-methylsulfonylbenzoic acid and organic amine generate organic ammonium salt under the action of organic solvent, then mix with inorganic base in water to obtain inorganic metal salt, and finally acidify with inorganic acid to obtain 2-nitrate Base-4-methylsulfonylbenzoic acid boutique
But the technical mesotrione refined by this method still has some impurities that do not meet the requirements

Method used

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  • Refining method of 2-nitro-4-methanesulfonylbenzoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] In a 500ml reaction flask, add 0.8g of sodium hydroxide and 158g of anhydrous methanol, stir at room temperature for 30 minutes, so that all the sodium hydroxide is dissolved in methanol; add 2-nitro-4-methylsulfonylbenzoic acid Crude product 50g (95% by weight), stirred, heated to 65°C and refluxed for 30 minutes, cooled to 60°C, filtered at 60°C, cooled the filtrate to 5°C, filtered at 5°C, dried to obtain 2-nitro- 45.8 g of 4-methylsulfonylbenzoic acid, the content was 98.6% by weight, and the yield was 95.07%.

Embodiment 2

[0042] In a 500ml reaction flask, add 1g of potassium hydroxide and 160g of absolute ethanol, and stir at room temperature for 30 minutes, so that all of the potassium hydroxide is dissolved in ethanol; add the crude product of 2-nitro-4-methylsulfonylbenzoic acid 50g (95% by weight), stir, heat up to 67°C and reflux for 30 minutes, cool to 60°C, filter at 60°C, cool the filtrate to 5°C, filter at 5°C, and dry to obtain 2-nitro-4 - 45.7 g of methylsulfonylbenzoic acid, the content is 98.8% by weight, and the yield is 95.05%.

Embodiment 3-7、 comparative example 1

[0044]Purify 2-nitro-4-methanesulfonylbenzoic acid according to the method of Example 1, the difference is that the amount of sodium hydroxide added is as shown in Table 1. The weight, content and yield of 2-nitro-4-methylsulfonylbenzoic acid finally obtained are shown in Table 1.

[0045] Table 1

[0046] Sodium hydroxide (g) Weight (g) Content (weight%) Yield (%) Example 1 0.8 45.8 98.6 95.07 Example 3 0.7 45.0 98.7 94.13 Example 4 0.9 45.4 98.6 94.24 Example 5 0.6 44.5 98.3 92.47 Example 6 2 38.0 98.7 78.96 Example 7 3 33.5 97.9 69.05 Comparative example 1 0 40 99.5 83.79

[0047] As can be seen from the above Table 1, by making the amount of base 0.09-0.12 mol relative to 1 mol of the 2-nitro-4-methylsulfonylbenzoic acid, the 2-nitro-4-methanol obtained by refining can be further increased. Sulfonylbenzoic acid weight and its content, yield.

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Abstract

The invention relates to the field of refining of organic matters, and discloses a refining method of 2-nitro-4-methanesulfonylbenzoic acid. The method comprises the following steps: (1) in the presence of an alcohol solvent, making a 2-nitro-4-methanesulfonylbenzoic acid crude product contact an alkali, and carrying out first solid-liquid separation on the contacting product; (2) cooling the liquid phase obtained by the first solid-liquid separation in the step (1) to crystallize and separate out 2-nitro-4-methanesulfonylbenzoic acid; and (3) carrying out second solid-liquid separation on theproduct obtained in the step (2) to obtain refined 2-nitro-4-methanesulfonylbenzoic acid. According to the invention, the purity and the yield of 2-nitro-4-methanesulfonylbenzoic acid refined by themethod are high, and the refining method does not generate wastewater and is simple and convenient to operate.

Description

technical field [0001] The invention relates to the field of refining organic matter, in particular to a method for refining 2-nitro-4-methylsulfonylbenzoic acid. Background technique [0002] 2-nitro-4-methylsulfonylbenzoic acid is a synthetic mesotrione (also known as Mesotrione, Mesotrione, (2-(4-methylsulfonyl-2-nitrobenzoyl) cyclohexane- 1,3-diketone). Mesotrione is a new type of systemic herbicide dedicated to cornfields. It has a wide herbicidal spectrum, high activity, strong miscibility, low toxicity, and environmental friendliness. It is safe for subsequent crops and flexible to use. [0003] Mesotrione uses 2-nitro-4-methylsulfonylbenzoic acid as the starting material, undergoes acid chloride, condensation, and rearrangement; the reaction process is as follows: [0004] [0005] WO2015062103A1, US7285678, etc. pointed out that the raw material impurities of 2-nitro-4-methylsulfonylbenzoic acid were too high, resulting in low purity of the original drug of mes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/06C07C317/44
CPCC07C315/06C07C317/44
Inventor 倪肖元王磊张晟王晓磊陈国斌涂俊清
Owner NUTRICHEM LAB CO LTD
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