CN101830866B - Method for preparing bentazone - Google Patents
Method for preparing bentazone Download PDFInfo
- Publication number
- CN101830866B CN101830866B CN2010103011599A CN201010301159A CN101830866B CN 101830866 B CN101830866 B CN 101830866B CN 2010103011599 A CN2010103011599 A CN 2010103011599A CN 201010301159 A CN201010301159 A CN 201010301159A CN 101830866 B CN101830866 B CN 101830866B
- Authority
- CN
- China
- Prior art keywords
- reaction
- add
- bentazone
- preparation
- sec
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Abstract
The present invention discloses a method for preparing bentazone, which comprises the following steps: 1), reacting a sulfonating agent, methyl anthranilate and isopropyl amine in an organic base and organic solution to generate a sulfonate; 2), adding phosphorus oxychloride into a system obtained by step 1) at the temperature of 15 to 30 DEG C, then raising the temperature to 50 to 85 DEG C, and stirring and reacting the reactants for 0.5 to 5 hours; 3), performing post treatment to obtain an intermediate, namely N-(2-methoxycarbonylphenyl)-N'-isopropylsulfonyldiamine; and 4), adding an alcohol solvent and the N-(2-methoxycarbonylphenyl)-N'- isopropylsulfonyldiamine into a reaction bottle, adding an alkali into the bottle to perform a reaction for 0.5 to 5 hours at the temperature of 30 to 65 DEG C, reclaiming the alcohol solvent, adding water and an acid into the solution until the pH value of the solution is less than or equal to 1 to crystallize and precipitate the bentazone, cooling the reaction solution, filtering the reaction solution, washing the filter cake, and drying the filter cake to obtain the finished product of the bentazone. The method of the invention is low in cost and pollution, high in yield and suitable for industrial production.
Description
Technical field
The present invention relates to a kind of preparation method of weedicide, particularly relate to a kind of preparation method of bentazone.
Background technology
Its formal name used at school of bentazone (having another name called bentazone) is 3-sec.-propyl-1H-benzo-2,1,3-thiadiazine-4 (3H)-ketone 2,2-dioxide, bentazone is a kind of important herbicide after seedling, and it is researched and developed successfully by German BASF AG and worldwide a large amount of the use at first.
Germany Patent document DE2357063 discloses a kind of preparation method of bentazone, and it is with methyl o-aminobenzoate and the reaction of isopropylamino SULPHURYL CHLORIDE, closes ring with sodium methylate again and obtains bentazone.Germany Patent document DE2105687 also discloses similar approach in addition, just at last obtains bentazone with light air to close ring.But above-mentioned two kinds of methods are difficult to realize industrialization, mainly are because the isopropylamino SULPHURYL CHLORIDE purification difficult of one of raw material.
It is the method that raw material prepares bentazone that Germany Patent document DE2710382 and Chinese patent literature CN1063688 disclose with the isatoic anhydride, though the quality product that this method obtains is better than two patents in front, it is further refining that but this method is not carried out intermediate N sec.-propyl-2-aminobenzamide in process of production, thereby exist impurity such as anthranilic acid, and in follow-up acid-alkali refining process, fail these impurity is removed, like this after being made into aquae concentrate, storage period one, length promptly can be separated out, and influence is used.The smell is awful for the catalyzer 2-picoline that adopts in this method in addition, and consumption is big, reclaims difficulty, strengthened production cost.
Summary of the invention
The objective of the invention is to overcome the problems referred to above, provide a kind of cost low, pollute less, the yield height, be fit to the preparation method of the bentazone of suitability for industrialized production.
Realize that technical scheme steps of the present invention is as follows: a kind of preparation method of bentazone, have following steps: sulphonating agent, methyl o-aminobenzoate and Isopropylamine as reactant are reacted, generate corresponding sulfonate in organic bases and organic solvent; 2. in the 1. resulting system of step, adding phosphorus oxychloride under 15 ℃～30 ℃ the temperature, be warming up to 50 ℃～85 ℃ after adding and also stir the reaction 0.5h～5h that generates N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine; 3. the 2. resulting system of step is carried out obtaining intermediate N (2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine after the aftertreatment; 4. intermediate N (2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine that 3. alcoholic solvent and step obtained joins in the reaction flask, add alkali, under 30 ℃～65 ℃ temperature, generate the reaction 0.5h～5h of bentazone, reclaim alcoholic solvent, add entry and acid makes the bentazone crystallization separate out until pH≤1 of solution, cool off, filter, wash filter cake then, drying obtains the bentazone finished product.
Above-mentioned steps a kind of method 1. is: add organic solvent and sulphonating agent in reaction flask, add organic bases under-10 ℃～0 ℃ temperature, thereby the reaction of sulphur trioxide/organic bases double salt takes place to generate, add back stirring reaction 0.5h～1h; Be warming up to 15 ℃～25 ℃ then and add Isopropylamine, add the back and stir 0.1h～0.5h; Be cooled to 8 ℃～12 ℃ then and add methyl o-aminobenzoate, thereby the reaction of sulfonate takes place to generate, add back stirring reaction 0.1h～2h, be warming up to 30 ℃～80 ℃ then and continue stirring reaction 0.1h～2h.The post-treating method of corresponding step described in 3. is: organic solvent is reclaimed in the system underpressure distillation that 2. step obtains, be cooled to 10 ℃～30 ℃ and N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine crystallization is separated out then, adding water stirs, filter, the washing filter cake, dry intermediate obtains N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine.
Above-mentioned another step method 1. is: add organic solvent and organic bases in reaction flask, add sulphonating agent under-10 ℃～0 ℃ temperature, thereby the reaction of sulphur trioxide/organic bases double salt takes place to generate, add back stirring reaction 0.5h～1h; Be warming up to 15 ℃～25 ℃ then and add Isopropylamine, add the back and stir 0.1h～0.5h; Be cooled to 8 ℃～12 ℃ then and add methyl o-aminobenzoate, thereby the reaction of sulfonate takes place to generate, add back stirring reaction 0.1h～2h, be warming up to 30 ℃～80 ℃ then and continue stirring reaction 0.1h～2h.The post-treating method of corresponding step described in 3. is: organic solvent is reclaimed in the system underpressure distillation that 2. step obtains, be cooled to 10 ℃～30 ℃ and N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine crystallization is separated out then, adding water stirs, filter, the washing filter cake, dry intermediate obtains N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine.
Above-mentioned steps the third method 1. is: add organic solvent, organic bases and Isopropylamine in reaction flask, stir the adding sulphonating agent then under-10 ℃～0 ℃ temperature, thereby the reaction of sulphur trioxide/organic bases double salt takes place to generate; Be warming up to 8 ℃～12 ℃ after adding, add methyl o-aminobenzoate again, thereby the reaction of corresponding sulfonate takes place to generate, be warming up to 30 ℃～80 ℃ stirring reaction 0.5h～4h after adding; Step method 3. is: the 2. resulting system of step is cooled to 15 ℃～25 ℃ adds the water stirring, standing demix, take out organic layer, underpressure distillation and reclaim organic solvent, remaining liq is cooled to 10 ℃～30 ℃ and N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine crystallization is separated out, and adds water and stirs, and filters, the washing filter cake, drying obtains intermediate N (2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine.
The alcoholic solvent of above-mentioned steps described in 4. is methyl alcohol or ethanol; Alkali is sodium methylate, sodium ethylate or sodium hydroxide; Acid is hydrochloric acid or sulfuric acid.
The organic bases of above-mentioned steps described in 1. is Trimethylamine 99, triethylamine, triisopropylamine, N, a kind of in N-dimethylcyclohexylam,ne, the N-methylpyrrole or two kinds or three kinds.
The organic solvent of above-mentioned steps described in 1. is ethylene dichloride, propylene dichloride or chlorobenzene.
The sulphonating agent of above-mentioned steps described in 1. is sulphur trioxide or chlorsulfonic acid.
The mol ratio of sulphonating agent, methyl o-aminobenzoate, Isopropylamine and the organic bases of above-mentioned steps described in 1. is 1: (0.72～1.5): (0.75～3): (1.8～4); The mol ratio of the sulphonating agent of step described in 1. and the step phosphorus oxychloride described in 2. is 1: (0.9～2.5).
Reaction formula of the present invention is as follows:
The positively effect that the present invention has is: it is raw material that (1) the present invention adopts methyl o-aminobenzoate, with sulphur trioxide or chlorsulfonic acid is sulphonating agent, crucial intermediate N (2-methoxycarbonyl phenyl)-the N '-sec.-propyl sulfonic acid diamine of preparation, and then refabrication bentazone finished product earlier.This method reactions steps is few, mild condition, and starting material are easy to get, and production cost is low, and the yield and the quality of product all are improved simultaneously, are fit to suitability for industrialized production.(2) method of the present invention has solved the problem that catalyst recovery and solvent are applied mechanically.Catalyst levels is few in the entire reaction course, rate of recovery height.And the direct recovery set usefulness of solvent does not need special processing.Catalyzer wherein is the unpleasant problem of odorlessness also, and the aquae concentrate that is made into does not have the problem of separating out and influencing use yet.
Embodiment
(embodiment 1)
The preparation method of the bentazone of present embodiment 1 has following steps:
1. in reaction flask, add the sulphonating agent sulphur trioxide of 40g and the organic solvent ethylene dichloride of 250mL, ice bath is cooled to-10 ℃～0 ℃, stir the reaction that slowly drips the organic bases triethylamine of 92.5g down and begin to generate sulphur trioxide/triethylamine double salt, drip off the back and stir insulation reaction 0.5h.Be warming up to 20 ℃ then, stir the Isopropylamine that drips 22.25g down, drip off the back and stir 0.3h.Be cooled to 10 ℃ then, stir the reaction that adds the methyl o-aminobenzoate of 54.5g down and begin to generate corresponding sulfonate, adding the back continues stirring reaction 0.2h, is warming up to 50 ℃～55 ℃ restir reaction 0.3h then.
2. the 1. resulting system of step is cooled to 15 ℃～30 ℃, drips the phosphorus oxychloride of 63g, be warming up to 80 ℃～85 ℃ after dripping off and also stir the reaction 0.5h that generates N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine.
3. the 2. resulting system of step is carried out the vacuum distillation recovered solvent ethylene dichloride, be cooled to 20 ℃ and N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine crystallization is separated out then, adding 200ml water stirs, filter, the washing filter cake, dry intermediate N (2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine of 93.2g, purity 88.2%, yield is 83.2%.
4. N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine of the 40g that in another reaction flask, adds the methyl alcohol of 200mL and 3. obtain by step, slowly Dropwise 5 3g concentration is the sodium methoxide solution of 30wt% under 20 ℃～30 ℃ temperature, dropwise back back flow reaction 1h under 30 ℃～65 ℃ temperature, distillating recovering solvent methyl alcohol, be cooled to 15 ℃～25 ℃, in resistates, add water, pH=1 with hydrochloric acid conditioning solution, the adularescent solid is separated out, and cooling is filtered, the washing filter cake, the dry bentazone that gets 32.8g, product purity is 95%, yield is 88%.
(embodiment 2)
All the other are substantially the same manner as Example 1 for present embodiment, and difference is the preparation of intermediate N (2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine.
1. in reaction flask, add the organic solvent ethylene dichloride of 50mL and the organic bases triethylamine of 18.5g, ice bath is cooled to-10 ℃～0 ℃, stir the reaction that drips the sulphonating agent sulphur trioxide of 8g down and begin to generate sulphur trioxide/triethylamine double salt, drip off the back and stir insulation reaction 0.5h.Be warming up to 20 ℃ then, stir the Isopropylamine that drips 4.43g down, drip off the back and stir 0.3h.Be cooled to 10 ℃ then, stir the reaction that adds the methyl o-aminobenzoate of 10.9g down and begin to generate corresponding sulfonate, adding the back continues stirring reaction 0.2h, is warming up to 80 ℃～85 ℃ restir reaction 0.3h then.
2. the 1. resulting system of step is cooled to 15 ℃～30 ℃, drips the phosphorus oxychloride of 15.3g, be warming up to 80 ℃～85 ℃ after dripping off and also stir the reaction response 0.5h that generates N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine.
3. the 2. resulting system of step is carried out the vacuum distillation recovered solvent ethylene dichloride, be cooled to 15 ℃ and N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine crystallization is separated out then, adding 100ml water stirs, filter, the washing filter cake, dry intermediate N (2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine of 18.1g, purity is 95.9%, yield is 88.2%.
(embodiment 3)
All the other are substantially the same manner as Example 1 for present embodiment, and difference is the preparation of intermediate N (2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine.
1. the organic solvent chlorobenzene, the organic bases triethylamine of 50.5g and the Isopropylamine of 19.3g that in reaction flask, add 220g, under-10 ℃～0 ℃ temperature, stir the reaction that also slowly drips the sulphonating agent chlorsulfonic acid of 23.3g and begin to generate sulphur trioxide/triethylamine double salt then, be warming up to 10 ℃ after dripping off, drip the methyl o-aminobenzoate of 15.1g again and begin to generate the reaction of corresponding sulfonate, drip off the back at 50 ℃～55 ℃ following stirring reaction 0.5h.
2. the 1. resulting system of step is cooled to 15 ℃～30 ℃, drips the phosphorus oxychloride of 23.6g, be warming up to 60 ℃～65 ℃ after dripping off and also stir the reaction response 1h that generates N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine.
3. the 2. resulting system of step is cooled to 15 ℃～25 ℃ and adds the water vigorous stirring, standing demix, get organic layer, the organic solvent chlorobenzene is reclaimed in underpressure distillation, and remaining liq is cooled to 20 ℃ and N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine crystallization is separated out, adding water stirs, filter, the washing filter cake, dry intermediate N (2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine of 23.9g, purity is 95%, and yield is 83.5%.
(embodiment 4)
All the other are substantially the same manner as Example 1 for present embodiment, and difference is the preparation of intermediate N (2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine.
1. the organic solvent ethylene dichloride, the organic bases triethylamine of 50.5g and the Isopropylamine of 19.3g that in reaction flask, add 220g, under-10 ℃～0 ℃ temperature, stir the reaction that also slowly drips the sulphonating agent chlorsulfonic acid of 23.3g and begin to generate sulphur trioxide/triethylamine double salt then, be warming up to 10 ℃ after dripping off, drip the methyl o-aminobenzoate of 15.1g again and begin to generate the reaction of corresponding sulfonate, drip off the back at 30 ℃～35 ℃ following stirring reaction 0.5h.
2. the 1. resulting system of step is cooled to 15 ℃～30 ℃, drips the phosphorus oxychloride of 23.6g, be warming up to 50 ℃～55 ℃ after dripping off and also stir the reaction response 1h that generates N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine.
3. the 2. resulting system of step is cooled to 15 ℃～25 ℃ and adds the water vigorous stirring, standing demix, get organic layer, vacuum distillation recovered solvent ethylene dichloride, remaining liq are cooled to 20 ℃ and N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine crystallization is separated out, adding water stirs, filter, the washing filter cake, dry intermediate N (2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine of 23.39g, purity is 93%, and yield is 80.1%.
Claims (10)
1. the preparation method of a bentazone is characterized in that having following steps:
Sulphonating agent, methyl o-aminobenzoate and Isopropylamine as reactant are reacted in organic bases and organic solvent, generate corresponding sulfonate;
2. in the 1. resulting system of step, adding phosphorus oxychloride under 15 ℃～30 ℃ the temperature, be warming up to 50 ℃～85 ℃ after adding and also stir the reaction 0.5h～5h that generates N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine;
3. the 2. resulting system of step is carried out obtaining intermediate N (2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine after the aftertreatment;
4. intermediate N (2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine that 3. alcoholic solvent and step obtained joins in the reaction flask, add alkali, under 30 ℃～65 ℃ temperature, generate the reaction 0.5h～5h of bentazone, reclaim alcoholic solvent, add entry and acid makes the bentazone crystallization separate out until pH≤1 of solution, cool off, filter, wash filter cake then, drying obtains the bentazone finished product.
2. the preparation method of bentazone according to claim 1, it is characterized in that: step method 1. is: add organic solvent and sulphonating agent in reaction flask, under-10 ℃～0 ℃ temperature, add organic bases, thereby the reaction of sulphur trioxide/organic bases double salt takes place to generate, add back stirring reaction 0.5h～1h; Be warming up to 15 ℃～25 ℃ then and add Isopropylamine, add the back and stir 0.1h～0.5h; Be cooled to 8 ℃～12 ℃ then and add methyl o-aminobenzoate, thereby the reaction of sulfonate takes place to generate, add back stirring reaction 0.1h～2h, be warming up to 30 ℃～80 ℃ then and continue stirring reaction 0.1h～2h.
3. the preparation method of bentazone according to claim 1, it is characterized in that: step method 1. is: add organic solvent and organic bases in reaction flask, under-10 ℃～0 ℃ temperature, add sulphonating agent, thereby the reaction of sulphur trioxide/organic bases double salt takes place to generate, add back stirring reaction 0.5h～1h; Be warming up to 15 ℃～25 ℃ then and add Isopropylamine, add the back and stir 0.1h～0.5h; Be cooled to 8 ℃～12 ℃ then and add methyl o-aminobenzoate, thereby the reaction of sulfonate takes place to generate, add back stirring reaction 0.1h～2h, be warming up to 30 ℃～80 ℃ then and continue stirring reaction 0.1h～2h.
4. according to the preparation method of claim 2 or 3 described bentazones, it is characterized in that: the post-treating method of step described in 3. is: organic solvent is reclaimed in the system underpressure distillation that 2. step obtains, be cooled to 10 ℃～30 ℃ and N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine crystallization is separated out then, adding water stirs, filter, the washing filter cake, dry intermediate obtains N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine.
5. the preparation method of bentazone according to claim 1, it is characterized in that: step method 1. is: add organic solvent, organic bases and Isopropylamine in reaction flask, under-10 ℃～0 ℃ temperature, stir the adding sulphonating agent then, thereby the reaction of sulphur trioxide/organic bases double salt takes place to generate; Be warming up to 8 ℃～12 ℃ after adding, add methyl o-aminobenzoate again, thereby the reaction of corresponding sulfonate takes place to generate, be warming up to 30 ℃～80 ℃ stirring reaction 0.5h～4h after adding; Step method 3. is: the 2. resulting system of step is cooled to 15 ℃～25 ℃ adds the water stirring, standing demix, take out organic layer, underpressure distillation and reclaim organic solvent, remaining liq is cooled to 10 ℃～30 ℃ and N-(2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine crystallization is separated out, and adds water and stirs, and filters, the washing filter cake, drying obtains intermediate N (2-methoxycarbonyl phenyl)-N '-sec.-propyl sulfonic acid diamine.
6. the preparation method of bentazone according to claim 1 is characterized in that: the alcoholic solvent of step described in 4. is methyl alcohol or ethanol; Alkali is sodium methylate, sodium ethylate or sodium hydroxide; Acid is hydrochloric acid or sulfuric acid.
7. according to the preparation method of claim 1,2,3 or 5 described bentazones, it is characterized in that: the organic bases of step described in 1. is Trimethylamine 99, triethylamine, triisopropylamine, N, a kind of in N-dimethylcyclohexylam,ne, the N-methylpyrrole or two kinds or three kinds.
8. according to the preparation method of claim 1,2,3 or 5 described bentazones, it is characterized in that: the organic solvent of step described in 1. is ethylene dichloride, propylene dichloride or chlorobenzene.
9. according to the preparation method of claim 1,2,3 or 5 described bentazones, it is characterized in that: the sulphonating agent of step described in 1. is sulphur trioxide or chlorsulfonic acid.
10. according to the preparation method of claim 1,2,3 or 5 described bentazones, it is characterized in that: the mol ratio of sulphonating agent, methyl o-aminobenzoate, Isopropylamine and the organic bases of step described in 1. is 1: (0.72～1.5): (0.75～3): (1.8～4); The mol ratio of the sulphonating agent of step described in 1. and the step phosphorus oxychloride described in 2. is 1: (0.9～2.5).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010103011599A CN101830866B (en) | 2010-02-03 | 2010-02-03 | Method for preparing bentazone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010103011599A CN101830866B (en) | 2010-02-03 | 2010-02-03 | Method for preparing bentazone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101830866A CN101830866A (en) | 2010-09-15 |
| CN101830866B true CN101830866B (en) | 2011-09-28 |
Family
ID=42715105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010103011599A Active CN101830866B (en) | 2010-02-03 | 2010-02-03 | Method for preparing bentazone |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101830866B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102617511A (en) * | 2012-03-09 | 2012-08-01 | 东北大学 | Wastewater-free preparation method of bentazon |
| CN102924405B (en) * | 2012-11-21 | 2016-01-20 | 合肥星宇化学有限责任公司 | A kind of preparation method of bentazone aqua |
| CN104447618A (en) * | 2014-12-26 | 2015-03-25 | 合肥星宇化学有限责任公司 | Method for purifying bentazon |
| CN104557776A (en) * | 2014-12-28 | 2015-04-29 | 江苏绿利来股份有限公司 | Synthesis method of bentazone |
| CN104693142B (en) * | 2015-03-31 | 2016-11-23 | 中国石油大学(华东) | A kind of improvement bentazone production method |
| CN107417545B (en) * | 2017-04-20 | 2019-08-16 | 浙江中山化工集团股份有限公司 | The aftertreatment technology of condensation liquid in a kind of Bentazon preparation process |
| CN111704592B (en) * | 2020-05-28 | 2022-06-28 | 山东潍坊润丰化工股份有限公司 | Production process for continuously preparing bentazon |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1063688A (en) * | 1991-01-28 | 1992-08-19 | 南开大学 | The synthetic method of Bentazon herbicide |
| CN1267287A (en) * | 1997-08-19 | 2000-09-20 | 巴斯福股份公司 | Method for production of 3-isoproyl-1H-2,1,3-benzothiadiazine-4-(3H)-one-2,2-dioxide |
-
2010
- 2010-02-03 CN CN2010103011599A patent/CN101830866B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1063688A (en) * | 1991-01-28 | 1992-08-19 | 南开大学 | The synthetic method of Bentazon herbicide |
| CN1267287A (en) * | 1997-08-19 | 2000-09-20 | 巴斯福股份公司 | Method for production of 3-isoproyl-1H-2,1,3-benzothiadiazine-4-(3H)-one-2,2-dioxide |
Non-Patent Citations (1)
| Title |
|---|
| 高凤成.灭草松合成新工艺探讨.《农药》.1986,21-22. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101830866A (en) | 2010-09-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101830866B (en) | Method for preparing bentazone | |
| CN104974060A (en) | Method for preparing sodium, 8-(2-hydroxybenzamido)octanoate | |
| CN107857743B (en) | Method for preparing roxatidine acetate hydrochloride and intermediate | |
| CN105646368A (en) | Preparation method of 2, 4-dichloro-5-methoxy pyrimidine | |
| CN101863858A (en) | Synthetic method of bentazone | |
| CN104059025A (en) | Novel intermediate used for preparation of avanafil and preparation method thereof | |
| CN102408364B (en) | Method for preparing paratoluensulfonyl chloride | |
| CN102153493A (en) | Novel method for preparing di(trimethyl fluoride sulfonyl)imine lithium | |
| CN108947861A (en) | The synthetic method of C14H10Cl2NNaO2 | |
| CN104119243B (en) | A kind of energy-saving clean production method of iminodiethanoic acid | |
| CN108424395A (en) | A kind of preparation method of sulfentrazone | |
| CN105481735B (en) | A kind of method for preparing orthanilic acid | |
| CN104650093B (en) | Synthesis method of sildenafil analog | |
| CN103319462B (en) | Preparation method of halosulfuron methyl | |
| CN105111103A (en) | Method for preparing cyanophenol and derivative thereof | |
| CN102875435A (en) | Organic thiosulfuric acid derivative preparation method | |
| CN105061362A (en) | Preparation method of bentazon | |
| CN101550097B (en) | Preparation method of 5-chlorosulfonyl isophthaloyl acid chloride | |
| CN110483433A (en) | The synthetic method of 4- methyl -5- ethyoxyl oxazole acetoacetic ester | |
| CN106810546A (en) | A kind of umeclidinium compound | |
| CN111689969A (en) | Preparation method of sildenafil | |
| CN111303045A (en) | Production process of 2-ethoxy-4, 6-difluoropyrimidine | |
| CN105017284A (en) | Preparation method for ceftizoxime alapivoxil, intermediates thereof and preparation method for intermediates | |
| CN109096134A (en) | A kind of preparation method of equal amido phenenyl acid methyl esters | |
| CN1035874C (en) | Preparation of 1-amino-1-cyanamido-2,2-dicyanoethylene, sodium salt abstract of the disclosure |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |