CN106565560A - Synthesis process of mesotrione - Google Patents

Synthesis process of mesotrione Download PDF

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Publication number
CN106565560A
CN106565560A CN201610995353.9A CN201610995353A CN106565560A CN 106565560 A CN106565560 A CN 106565560A CN 201610995353 A CN201610995353 A CN 201610995353A CN 106565560 A CN106565560 A CN 106565560A
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oxidation
product
temperature
nitric acid
reaction
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李岳林
张晓臣
李萍
张强
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Hubei Guangfulin Biological Preparation Co Ltd
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Hubei Guangfulin Biological Preparation Co Ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00Preparation of sulfones; Preparation of sulfoxides
    • C07C315/06Separation; Purification; Stabilisation; Use of additives

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a synthesis process of mesotrione. The synthesis process is high in yield and high in product purity and comprises the following steps: adding concentrated sulfuric acid, an oxidation water-containing mother solution and methyl p-tolyl sulfone into a nitration reaction kettle, evenly dropwise adding nitric acid in 2-3 hours to carry out nitratlon reaction, and keeping the temperature for 60-70 minutes after finishing dropwise adding nitric acid to obtain a nitrification solution; introducing the nitrification solution into an oxidation reaction kettle, then adding V2O5 as a catalyst, dropwise adding nitric acid and controlling the reaction temperature to be 142-146 DEG C; keeping the temperature for 1-2 hours after finishing dropwise adding nitric acid; reducing the temperature of a reaction solution to 100 DEG C, then adding water, and then reducing the temperature to 48-50 DEG C, then carrying out pressure filtration to obtain an oxidation product and the oxidation water-containing mother solution, circularly rinsing the oxidation product with water; refining the oxidation product and then drying the oxidation product at 55-70 DEG C to obtain 2-nitryl-4-methylsulfonylbenzoic acid; adding sulfoxide chloride into an acyl chlorination reaction kettle, then adding 2-nitryl-4-methylsulfonylbenzoic acid and DMF for increasing the temperature and carrying out reflux reaction, distilling after reacting for 11-12 hours for separating sulfoxide chloride out, and then carrying out esterification, condensation and rearrangement.

Description

A kind of synthesis technique of mesotrione
Technical field
The invention belongs to chemical field, and in particular to a kind of synthesis technique of mesotrione.
Background technology
Mesotrione action target is p-hydroxyphenypyruvate dioxydenase (HPPD), is mainly used in preventing and kill off corn field Broad leaved weed and grassy weed, with herbicidal spectrum it is wide, Environmental compatibility is good, very low to mammal and aquatic toxicity, It is fool proof to Semen Maydiss and to rear stubble rotation crop without characteristics such as poisoning, it is front with the very big market demand and good application Scape.Additionally, mesotrione to prevent and kill off anti-three pyridine especially effective with the weeds of anti-sulfonylureas, weeds are in it and these type herbicides Between there is no cross resistance, this just provides convenience to herbicide Fruit variety in crop rotation.
At present, mesotrione typically is carried out being condensed rearrangement reaction system by intermediate 2- nitro -4- methylsulphonyl benzoyl chlorides It is standby.And the synthesis of intermediate 2- nitro -4- methylsulphonyl benzoyl chlorides has various methods.At present, further closed by these methods Overall reaction yield into mesotrione is preferable, up to 78% or so, but still has larger room for promotion.And product purity is low, very It is rare poor to the mesotrione in accordance with prescription, i.e. product purity, while in the conjunction of 2- nitro -4- methylsulphonyl benzoyl chlorides Cheng Zhong, various nitre compound impurities of generation increased the danger of industrialized production to next step synthesizing methyl sulphur oxadiazon.
The content of the invention
To solve the above problems, the invention provides a kind of synthesis technique of the high mesotrione of high income, product purity.
The synthesis technique of mesotrione provided by the present invention, including step:
Nitrification:400~500kg of concentrated sulphuric acid, oxidation 1100~1200kg of water-bearing mother liquor are added in nitration reaction kettle, to MSM Base 350~360kg of toluene, in 2~3 hours, 98% nitric acid of uniform Deca 180kg carries out nitration reaction, is incubated after completion of dropping 60~70 minutes, obtain nitrification liquid;
Oxidation:Catalyst V2O5, then Deca 1240~1290kg nitric acid are added after nitrification liquid is imported oxidizing reactor, And controlling reaction temperature is 142~146 DEG C;1~2 hour is incubated after completion of dropwise addition;Reactant liquor is cooled to filter pressing after 50 degree to obtain To oxidation product and oxidation water-bearing mother liquor, with 1000~1100kg of water circulation rinsing oxidation products;Will after will be oxidation product refined Which is dried to obtain 2- nitro -4- methyl sulfonylbenzoic acids at 55~70 DEG C;
Chloride:Thionyl chloride is added in acyl chloride reaction kettle, then puts into 2- nitro -4- methyl sulfonylbenzoic acids, DMF To carry out temperature rising reflux reaction, after reaction 11~12 hours, separated goes out thionyl chloride, obtain 2- nitro -4- mesyls - Benzenecarbonyl chloride..
Condensation is reset:After the 2- nitro -4- methylsulphonyl benzoyl chloride dichloromethane for obtaining is dissolved well, it is cooled to 15~40 DEG C, the 1 of 150~170kg of input, hydroresorcinol, uniform Deca 160~180kg triethylamines in 60~80 minutes Carry out esterification condensation;The mixed liquor for adding 5~20kg .alpha.-hydroxyisobutyronitrile .s and 150~180kg triethylamines carries out rearrangement reaction, then plus It is 1~2 that hydrochloric acid is adjusted to pH, point liquid washing, and to reclaim dichloromethane, then blowing, sucking filtration obtain crude product sulphur oxadiazon for the distillation that adds water;Take advantage of In the crude product sulphur oxadiazon input refining reaction kettle that sucking filtration is gone out by heat, stir 20~40 minutes at 50~55 DEG C, sucking filtration after blowing, Mother solution enters the distillation of methanol distillating still and refines to reclaim methanol, and mesotrione finished product will be obtained after solid product drying, comminution by gas stream.
Its except high income, product purity height in addition to, due to the reuse to oxidation mother liquor, it is possible to reduce the use of catalyst Amount, and the product ton consumption of fresh water can be reduced, while reducing waste water;And shorter, reacting balance is easy to control the time required to reacting System.By Deca .alpha.-hydroxyisobutyronitrile. and the mixed solution of triethylamine, the severe degree reset is reduced, safe operation is improve.Steam First add water before evaporating dichloromethane, by aqueous distillation, it is to avoid still-process localized hyperthermia, be also prevented from dichloromethane and steam rear material Solidify and damage equipment.
Preferably, in the denitrification step, the mass concentration of the nitric acid is 98%.
Preferably, in the oxidation step, the consumption of catalyst V2O5 is 4~5kg.
Preferably, in Deca nitric acid, uniform Deca 890~920kg of nitric acid first in 17~19 hours, while control Reaction temperature is 144~146 degree;Uniform Deca 350~370kg nitric acid in 14.5~16 hours again, while controlling reaction temperature Spend for 142~144 degree;1~2 hour is incubated after completion of dropwise addition.As such, it is possible to further effectively reduce byproduct of reaction, improve Product purity.
Preferably, when the oxidation product is refined, in oxidation product, NaOH solution is added to adjust pH value to 8.0~9.0, To dissolve oxidation product, temperature is controlled in adition process for 55~60 DEG C;Then pH value is adjusted in blowing centrifugation while hot, Deca hydrochloric acid To 1~2, kept for 30~50 minutes in the range of 55~60 DEG C of temperature, after being cooled to 35 DEG C, centrifugation, rinsing, obtain final product refined 2- Nitro -4- methyl sulfonylbenzoic acids.
Preferably, thionyl chloride is added in acyl chloride reaction kettle, then puts into 2- nitro -4- methyl sulfonylbenzoic acids, DMF To carry out temperature rising reflux reaction, after reaction 11~12 hours, separated goes out thionyl chloride, obtain 2- nitro -4- mesyls - Benzenecarbonyl chloride..
Preferably, when esterification condensation is reset, will be the 2- nitro -4- methylsulphonyl benzoyl chloride dichloromethane for obtaining molten After solution is good, 15~20 DEG C are cooled to, the 1 of 155~165kg of input, hydroresorcinol, the uniform Deca in 60~80 minutes 175~180kg triethylamines carry out esterification condensation;Add the mixed liquor of 10~15kg .alpha.-hydroxyisobutyronitrile .s and 150~165kg triethylamines Carry out rearrangement reaction, then salt adding acid be adjusted to pH for 1~2, point liquid washing, the distillation that adds water to reclaim dichloromethane, then blowing, take out Filter to obtain crude product sulphur oxadiazon;While hot sucking filtration is gone out crude product sulphur oxadiazon input refining reaction kettle in, at 50~55 DEG C stirring 20~ 40 minutes, sucking filtration after blowing, mother solution entered the distillation of methanol distillating still and refine to reclaim methanol, by solid product drying, air-flow powder Mesotrione finished product is obtained after broken.
Specific embodiment
Embodiment 1
In nitration reaction kettle 98% concentrated sulphuric acid 400kg of addition, to methylsulfonyltoluene 360kg and oxidation water-bearing mother liquor 1100kg Afterwards, in 4 hours, 98% nitric acid of uniform Deca 180kg carries out nitration reaction, is incubated 60 minutes, is nitrified after completion of dropping Liquid;4kg catalyst V2O5 are added after nitrification liquid is imported oxidizing reactor, after being warming up to 142 degree, was uniformly dripped in 17 hours Plus 68% nitric acid 920kg, while controlling reaction temperature is 144 degree;Again in 16 hours uniform Deca 370kg 50% nitric acid, Controlling reaction temperature is 142 degree simultaneously;2 hours are incubated after completion of dropwise addition.Reactant liquor is cooled to into 48 degree, then filter pressing obtains oxygen Change product and oxidation water-bearing mother liquor, with water 1000kg circulation rinsing oxidation products;To in oxidation product, add NaOH solution to adjust pH It is worth to 8.0, to dissolve oxidation product, temperature is controlled in adition process for 55 DEG C;Then blowing centrifugation while hot, Deca hydrochloric acid are adjusted PH value is kept for 50 minutes to 1 at 55 DEG C of temperature, and after being cooled to 35 DEG C, centrifugation, rinsing, obtain final product refined 2- nitro -4- first sulphurs Acyl group benzoic acid;Which is dried to obtain at 70 DEG C 2- nitro -4- methyl sulfonylbenzoic acids;Chloride:In acyl chloride reaction kettle Middle addition thionyl chloride, then put into 2- nitro -4- methyl sulfonylbenzoic acids, DMF to carry out temperature rising reflux reaction, reaction 11~12 After hour, separated goes out thionyl chloride, obtains 2- nitros -4- mesyls-Benzenecarbonyl chloride..
After the 2- nitro -4- methylsulphonyl benzoyl chloride dichloromethane for obtaining is dissolved well, 15 DEG C are cooled to, are put into The 1 of 160kg, hydroresorcinol, in 60 minutes, uniform Deca 170kg triethylamine carries out esterification condensation;Add 10kg acetone The mixed liquor of cyanalcohol and 150kg triethylamines, carries out rearrangement reaction, then salt adding acid is adjusted to pH for 1.5 or so, and point liquid washing adds water To reclaim dichloromethane, then blowing, sucking filtration obtain crude product sulphur oxadiazon for distillation;The crude product sulphur oxadiazon input that while hot sucking filtration is gone out is refined In reactor, stir 20 minutes at 50 DEG C, sucking filtration after blowing, mother solution enters the distillation of methanol distillating still and refines to reclaim methanol, will Mesotrione finished product is obtained after solid product drying, comminution by gas stream.
The mesotrione product purity for obtaining is 98.15%, and yield is 88.08%.
Embodiment 2
In nitration reaction kettle 98% concentrated sulphuric acid 500kg of addition, to methylsulfonyltoluene 350kg and oxidation water-bearing mother liquor 1100kg Afterwards, in 5 hours, 98% nitric acid of uniform Deca 180kg carries out nitration reaction, is incubated 70 minutes, is nitrified after completion of dropping Liquid;5kg catalyst V2O5 are added after nitrification liquid is imported oxidizing reactor, after being warming up to 142 degree, was uniformly dripped in 19 hours Plus 68% nitric acid 890kg, while controlling reaction temperature is 146 degree;Again in 14.5 hours uniform Deca 350kg 50% nitre Acid, while controlling reaction temperature is 144 degree;1 hour is incubated after completion of dropwise addition.Reactant liquor is cooled to into 50 degree, then filter pressing is obtained To oxidation product and oxidation water-bearing mother liquor, with water 1100kg circulation rinsing oxidation products;NaOH solution is added in oxidation product PH value is adjusted to 9.0, to dissolve oxidation product, temperature is controlled in adition process for 60 DEG C;Then blowing centrifugation while hot, Deca salt Acid adjusts pH value to 2, is kept for 30 minutes under temperature 60 C, and after being cooled to 35 DEG C, centrifugation, rinsing, obtain final product refined 2- nitro -4- Methyl sulfonylbenzoic acid;Which is dried to obtain at 55 DEG C 2- nitro -4- methyl sulfonylbenzoic acids;Chloride:It is anti-in chloride Thionyl chloride is added in answering kettle, then puts into 2- nitro -4- methyl sulfonylbenzoic acids, DMF to carry out temperature rising reflux reaction, reaction 11 After~12 hours, separated goes out thionyl chloride, obtains 2- nitros -4- mesyls-Benzenecarbonyl chloride..
Condensation is reset:After the 2- nitro -4- methylsulphonyl benzoyl chloride dichloromethane for obtaining is dissolved well, it is cooled to 15 DEG C, the 1 of input 165kg, hydroresorcinol, in 80 minutes, uniform Deca 175kg triethylamine carries out esterification condensation;Add 15kg .alpha.-hydroxyisobutyronitrile .s, Deca 160kg triethylamine carry out rearrangement reaction, then salt adding acid is adjusted to pH for 1.0 or so, point liquid washing, plus Water is distilled to reclaim dichloromethane, and then blowing, sucking filtration obtain crude product sulphur oxadiazon;The crude product sulphur oxadiazon input essence that while hot sucking filtration is gone out In reactor processed, stir 40 minutes at 55 DEG C, sucking filtration after blowing, mother solution enters the distillation of methanol distillating still and refines to reclaim methanol, Mesotrione finished product will be obtained after solid product drying, comminution by gas stream.
The mesotrione product purity for obtaining is 97.95%, and yield is 89.66%.
Embodiment 3
In nitration reaction kettle 98% concentrated sulphuric acid 450kg of addition, to methylsulfonyltoluene 350kg and oxidation water-bearing mother liquor 1100kg Afterwards, in 4.5 hours, 98% nitric acid of uniform Deca 180kg carries out nitration reaction, is incubated 65 minutes, is nitrified after completion of dropping Liquid;4.5kg catalyst V2O5 are added after nitrification liquid is imported oxidizing reactor, it is after being warming up to 142 degree, uniform in 18 hours 68% nitric acid 900kg of Deca, while controlling reaction temperature is 145 degree;350~370kg of uniform Deca in 15 hours again 50% nitric acid, while controlling reaction temperature is 143 degree;1.5 hours are incubated after completion of dropwise addition.Reactant liquor is cooled to into 49 degree, so Filter pressing afterwards obtains oxidation product and oxidation water-bearing mother liquor, with water 1050kg circulation rinsing oxidation products;Add in oxidation product NaOH solution adjusts pH value to 8.5, to dissolve oxidation product, controls temperature for 57 DEG C in adition process;Then while hot blowing from The heart, Deca hydrochloric acid adjust pH value to 1.5, are kept for 40 minutes in the range of 57 DEG C of temperature, and after being cooled to 35 DEG C, centrifugation, rinsing, obtain final product Refined 2- nitro -4- methyl sulfonylbenzoic acids;Which is dried to obtain at 65 DEG C 2- nitro -4- methyl sulfonylbenzoic acids;Acyl Chlorination:Thionyl chloride is added in acyl chloride reaction kettle, then 2- nitro -4- methyl sulfonylbenzoic acids, DMF is put into be heated up Back flow reaction, after reacting 11~12 hours, separated goes out thionyl chloride, obtains 2- nitros -4- mesyls-Benzenecarbonyl chloride..
After the 2- nitro -4- methylsulphonyl benzoyl chloride dichloromethane for obtaining is dissolved well, 17 DEG C are cooled to, are put into The 1 of 165kg, hydroresorcinol, in 70 minutes, uniform Deca 180kg triethylamine carries out esterification condensation;Add 12kg acetone The mixed liquor of cyanalcohol and 150kg triethylamines carries out rearrangement reaction, then salt adding acid is adjusted to pH for 1 or so, point liquid washing, and add water distillation To reclaim dichloromethane, then blowing, sucking filtration obtain crude product sulphur oxadiazon;The crude product sulphur oxadiazon input refining reaction that while hot sucking filtration is gone out In kettle, stir 30 minutes at 53 DEG C, sucking filtration after blowing, mother solution enters the distillation of methanol distillating still and refines to reclaim methanol, by solid Mesotrione finished product is obtained after product drying, comminution by gas stream.
The mesotrione product purity for obtaining is 98.22%, and yield is 88.73%.
Finally it should be noted that:Various embodiments above only to illustrate technical scheme, rather than a limitation;To the greatest extent Pipe has been described in detail to the present invention with reference to foregoing embodiments, it will be understood by those within the art that:Its according to So the technical scheme described in foregoing embodiments can be modified, or which part or all technical characteristic are entered Row equivalent;And these modifications or replacement, do not make the essence of appropriate technical solution depart from various embodiments of the present invention technology The scope of scheme.

Claims (6)

1. a kind of synthesis technique of mesotrione, it is characterised in that including step:
Nitrification:400~500kg of concentrated sulphuric acid, oxidation 1100~1200kg of water-bearing mother liquor are added in nitration reaction kettle, to methylsulfonyl first 350~360kg of benzene, in 2~3 hours, 98% nitric acid of uniform Deca 180kg carries out nitration reaction, after completion of dropping insulation 60~ 70 minutes, obtain nitrification liquid;
Oxidation:Catalyst V2O5, then Deca 1240~1290kg nitric acid are added after nitrification liquid is imported oxidizing reactor, and is controlled Reaction temperature processed is 142~146 DEG C;1~2 hour is incubated after completion of dropwise addition;Reactant liquor is cooled to into filter pressing after 50 degree and obtains oxygen Change product and oxidation water-bearing mother liquor, with 1000~1100kg of water circulation rinsing oxidation products;After will be oxidation product refined by its 2- nitro -4- methyl sulfonylbenzoic acids are dried to obtain at 55~70 DEG C;
Chloride:Thionyl chloride is added in acyl chloride reaction kettle, then 2- nitro -4- methyl sulfonylbenzoic acids, DMF is put into enter Row temperature rising reflux reacts, and after reacting 11~12 hours, separated goes out thionyl chloride, obtains 2- nitros -4- mesyls-benzene first Acyl chlorides.
Condensation is reset:By the 2- nitro -4- methylsulphonyl benzoyl chloride dichloromethane for obtaining dissolve it is good after, be cooled to 15~ 40 DEG C, the 1 of 150~170kg of input, hydroresorcinol, in 60~80 minutes, uniform 160~180kg of Deca triethylamines are carried out Esterification condensation;The mixed liquor for adding 5~20kg .alpha.-hydroxyisobutyronitrile .s and 150~180kg triethylamines carries out rearrangement reaction, then salt adding acid It is 1~2 to be adjusted to pH, point liquid washing, and to reclaim dichloromethane, then blowing, sucking filtration obtain crude product sulphur oxadiazon for the distillation that adds water;While hot will In the crude product sulphur oxadiazon input refining reaction kettle that sucking filtration goes out, stir 20~40 minutes at 50~55 DEG C, sucking filtration after blowing, mother solution Enter the distillation of methanol distillating still refined to reclaim methanol, mesotrione finished product will be obtained after solid product drying, comminution by gas stream.
2. synthesis technique as claimed in claim 1, it is characterised in that in denitrification step, the mass concentration of the nitric acid is 98%.
3. synthesis technique as claimed in claim 1, it is characterised in that in oxidation step, the consumption of catalyst V2O5 is 4~ 5kg。
4. synthesis technique as claimed in claim 1, it is characterised in that in the oxidation step, in Deca nitric acid, exist first Uniform Deca 890~920kg of nitric acid in 17~19 hours, while controlling reaction temperature is 144~146 degree;Again 14.5~16 Uniform Deca 350~370kg nitric acid in hour, while controlling reaction temperature is 142~144 degree;1~2 is incubated after completion of dropwise addition Hour.
5. synthesis technique as claimed in claim 1, it is characterised in that when the oxidation product is refined, in oxidation product Add NaOH solution pH value to be adjusted to 8.0~9.0, to dissolve oxidation product, control temperature for 55~60 DEG C in adition process;So Blowing centrifugation while hot afterwards, Deca hydrochloric acid adjust pH value to 1~2, kept for 30~50 minutes, be cooled in the range of 55~60 DEG C of temperature After 35 DEG C, centrifugation, rinsing, obtain final product refined 2- nitro -4- methyl sulfonylbenzoic acids.
6. synthesis technique as claimed in claim 1, it is characterised in that condensation rearrangement process 5~20kg of Deca .alpha.-hydroxyisobutyronitrile .s and The mixed liquor of 150~180kg triethylamines, carries out esterification rearrangement reaction.It is 1~2 that salt adding acid is adjusted to pH again, point liquid washing, is added water, To reclaim dichloromethane, then blowing, sucking filtration obtain crude product sulphur oxadiazon for distillation.
CN201610995353.9A 2016-11-11 2016-11-11 Synthesis process of mesotrione Pending CN106565560A (en)

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CN110818601A (en) * 2019-11-22 2020-02-21 湖北广富林生物制剂有限公司 Preparation method of mesotrione
CN113354563A (en) * 2021-06-07 2021-09-07 浙江天诺医药科技有限公司 Method for preparing triketone compound by continuous flow

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Publication number Priority date Publication date Assignee Title
CN110818601A (en) * 2019-11-22 2020-02-21 湖北广富林生物制剂有限公司 Preparation method of mesotrione
CN113354563A (en) * 2021-06-07 2021-09-07 浙江天诺医药科技有限公司 Method for preparing triketone compound by continuous flow

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Application publication date: 20170419

RJ01 Rejection of invention patent application after publication