226944-49-6

Upstream product

• 110964-80-2 4-methylsulphonyl-2-nitrobenzoyl chloride 
• 504-02-9 1,3-cylohexanedione 
• 98-59-9 p-toluenesulfonyl chloride 
• 3185-99-7 Methyl p-tolyl sulfone 
• 1874-83-5 cyclohexane-1,3-dione sodium enolate 
• 616-83-1 4-methyl-3-nitrobenzenesulfonyl chloride 
• 88-72-2 1-methyl-2-nitrobenzene 
• 1671-49-4 1‐methyl‐4‐(methylsulfonyl)‐2‐nitrobenzene 
• 110964-79-9 4-methanesulfonyl-2-nitro-benzoic acid 
• 97-07-4 1-chloro-4-methanesulfonyl-2-nitrobenzene 
• 453-72-5 1-fluoro-4-methanesulfonyl-2-nitrobenzene 
• 5682-75-7 3-chloro-2-cyclohexenone 
• 765-87-7 cyclohexane-1,2-dione 

Downstream Products

• 104206-82-8 mesotrione 

Relevant academic research and scientific papers

A method for preparing nitroxalone herbicide

The present invention belongs to the field of organic synthesis, specifically relates to a method for preparing nitrosulfonone herbicides. 4-Methylsulfonyl-2-nitrobenzoic acid as raw material by acyl chloride reaction, esterification reaction to obtain a

Preparation method of mesotrione

The invention provides a preparation method of mesotrione. The preparation method comprises: S1) carrying out a reaction on 2-nitro-4-methylsulfonylbenzoyl chloride and 1, 3-cyclohexanedione in the presence of an acid-binding agent to obtain an enol ester reaction liquid; and S2) adding a rearrangement agent as shown in a formula (I) into the enol ester reaction liquid, and performing a rearrangement reaction to obtain mesotrione. Compared with the prior art, the method has the advantages that the rearrangement agent containing unsaturated double bonds is adopted, under the synergistic effect of the double bonds, the rearrangement agent has better reactivity and reaction rate in the rearrangement reaction process, and the green and environment-friendly aftertreatment method is simple.

Preparation method of mesotrione

The invention provides a preparation method of mesotrione. The preparation method comprises the following steps: taking p-methylsulfonyl o-nitrobenzoic acid as a raw material; after carrying out acylchlorination, carrying out condensation reaction with 1,3-cyclohexanedione to obtain an intermediate 2-nitryl-4-methylsulfonylbenzoic acid-[3'-carbonyl-1'-cyclohexenol]-ester; then carrying out rearrangement of enol ester under a common catalysis effect of inorganic alkali and tertiary amine type organic alkali with relatively strong basicity, so as to obtain an acrylated cyclic 1,3-dicarbonyl compound mesotrione. According to the method provided by the invention, a virulent cyanide catalyst is not used, the reaction temperature is relatively low and the reaction time is short; a solvent can be cyclically used, the total mol yield of a prepared mesotrione product can reach 95 percent and the content is 98.5 percent; the technology is safe and environmentally friendly, has a small amount ofthree wastes and is suitable for industrial production.

SYNTHESIS OF MESOTRIONE

The present disclosure relates to a method for the synthesis of mesotrione. The method comprises reacting p-toluene sulfonyl chloride with alkali metal sulphite and alkali metal bicarbonate to obtain p-toluene alkali metal sulfinate. The p-toluene alkali metal sulfinate is reacted with alkali metal salt of monochloroacetic acid to obtain p- methylsulfonyl toluene. Further, p-methylsulfonyl toluene is nitrated to obtain 2-nitro-p- methylsulfonyl toluene. 2-nitro-p-methylsulfonyl toluene is oxidized and then halogenated to obtain 2-nitro-p-methylsulfonylbenzoyl halide. 2-nitro-p-methylsulfonylbenzoyl halide is reacted with alkali metal salt of 1,3-cyclohexanedione to obtain 3-(2-Nitro-p-methyl sulfonyl benzoyloxy) cyclohexane-l-one. 3-(2-Nitro-p-methyl sulfonyl benzoyloxy) cyclohexane-1- one is reacted with base, a third fluid medium and cyanide ion source to obtain an amorphous mesotrione. The present disclosure also discloses the steps of converting the amorphous mesotrione to crystalline mesotrione having purity greater than 99 %. The process of the present disclosure for preparing mesotrione is rapid, economic, and environment friendly.

PROCESS FOR PREPARING MESOTRIONE

A process for the preparation of mesotrione enolate is provided. The process comprises providing a solution of mesotrione in an organic solvent and contacting the solution with a moderate base in the presence of water at a pH of from 6 to 8, to form an aqueous mesotrione enolate solution. A process for preparing mesotrione from the products of an enol ester rearrangement of 3-oxocyclohex-1-enyl-4-(methylsulfonyl)-2-nitrobenzoate is also provided. The process comprises contacting the products of the rearrangement reaction with an organic solvent to dissolve mesotrione; and contacting the resulting solution with an aqueous solution of an acid.

Preparation method of triketone compound and triketone compound intermediate

The present invention discloses a preparation method of a triketone compound and a triketone compound intermediate. The method is as follows: a compound (III) is obtained by nucleophilic substitution reaction of a compound (I) as a raw material and a compound (II) under the action of a base and then oxidation reaction, and the triketone desired product is obtained by acyl chlorination, esterification and rearrangement of the compound (III). The beneficial effects are mainly reflected as follows: the method is mild in reaction conditions, simple in process, high in yield, good in product quality, low in production costs, less in three-waste, and suitable for industrial production.

Synthesis method of mesotrione

The invention discloses a synthesis method of mesotrione. The method includes the following steps that firstly, acylation is performed, wherein 2-nitro-4-methylsulfonylbenzoic acid and acylating agents are subjected to an acylation reaction under catalysis of depolymerizing agents, acylation reaction liquid is obtained, and the temperature of the acylation reaction is 10-70 DEG C; secondly, esterification is performed, wherein acid binding agents and 1,3-cyclohexanedione are added in esterification reaction liquid, an esterification reaction is performed, the esterification reaction liquid is obtained, the temperature of the esterification reaction is 30-65 DEG C, and the acid binding agents are inorganic acid; thirdly, rearrangement is performed, wherein rearrangement agents are added in the esterification reaction liquid so that a rearrangement reaction can be performed, and coarse product reaction liquid is obtained; fourthly, refining is performed, wherein the coarse product reaction liquid is subjected to alkali liquor reverse extraction, acidification and recrystallization, and mesotrione is obtained. The method is easy to operate, the raw materials are easy to obtain, the reactant conversion rate is high, reaction is thorough, the purity of the product is high, and the synthesis method is applicable to industrial production.

A method for preparing of mesotrione

The invention provides a preparation method of mesotrione. The preparation method comprises is capable of preparing the target product from raw materials such as ortho-nitrotoluene, chlorosulfonic acid, sulfoxide chloride, sodium sulfite, chloroactic acid, 1,3-cyclohexanedione in the presence of a catalyst and acid-base. The preparation method is based on common chemical raw materials, the reaction flow of each step is implemented under conventional operation conditions, the amount of three wastes is low, the total yield is above 61%, the purity of the product is high, the purity of the coarse product of the mesotrione is greater than 98%, and the coarse product of the mesotrione can be further purified; as a result, the preparation method of mesotrione is applicable to large-scale industrial production.

PROCESS FOR PURIFYING MESOTRIONE

A method for reducing the cyanide levels in a mesotrione sample, said method comprising: (i) taking an aqueous solution of the mesotrione sample in an aqueous solvent, (ii) adjusting the pH of said aqueous solution to a value of 9.5 or higher, and (iii) crystallising the mesotrione out of solution is disclosed.

PROCESS FOR PURIFYING MESOTRIONE

A process for reducing the levels of undesirable impurities in a mesotrione sample is disclosed, said process comprising the steps of: (i) forming a mesotrione enolate solution in an aqueous solvent, (ii) carrying out one or more purification processes, and (iii) crystallising the purified mesotrione out of solution.