CN1830942A - Improved alkylation process for producing Mediben - Google Patents
Improved alkylation process for producing Mediben Download PDFInfo
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- CN1830942A CN1830942A CN 200610039170 CN200610039170A CN1830942A CN 1830942 A CN1830942 A CN 1830942A CN 200610039170 CN200610039170 CN 200610039170 CN 200610039170 A CN200610039170 A CN 200610039170A CN 1830942 A CN1830942 A CN 1830942A
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- organic solvent
- dicamba
- sodium hydroxide
- sulfate
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Abstract
An improved alkylating process for preparing dicamba includes such steps as dissolving 3,6-dichloro salicylic acid in organic solvent, dropping dimethyl sulfate, reaction, removing solvent by evaporating, and reacting on the solution of sodium hydroxide to obtain the sadium salt of dicamba.
Description
Technical field
The present invention relates to the production method of weedicide, refer in particular to the alkylation process in the dicamba 98 production.
Background technology
In the whole weedicide dicamba 98 production technique, 2, the 5-dichlorphenamide bulk powder obtains intermediate 2 after sulfuric acid, Sodium Nitrite diazotization, the 5-chlorophenesic acid, 2, the 5-chlorophenesic acid transfers 2 to the potassium hydroxide reaction again, 5-two chlorophenol potassium, 2,5-two chlorophenol potassium are isolated another intermediate 3 through carbonic acid gas, carbonic acid clock carboxylation, the 6-dichlorosalicylic acid, 3, the 6-dichlorosalicylic acid drips methyl-sulfate and refluxes between 100-104 ℃ in the aqueous solution of sodium hydroxide, and acquisition dicamba sodium salt acidifying again can get the finished product dicamba 98.Because methyl-sulfate is water insoluble, the productive rate of this reaction can only reach 80%, in addition, because of methyl-sulfate toxicity bigger, in sodium hydroxide solution, directly add methyl-sulfate, the poor stability of technology, the production of this non-cleaning make the production operation environment be subjected to the murder by poisoning of methyl-sulfate easily.
Summary of the invention
The present invention is just in order to overcome above-mentioned deficiency, alkylation process in a kind of improved dicamba 98 production is provided, make reaction can fully obtain high yield, technology is cleaned, reduce the toxicity of operating environment, the main improvement is 3, dripping methyl-sulfate in the 6-dichlorosalicylic acid carries out in organic solvent, because of two materials all are dissolved in organic solvent, reduced the murder by poisoning of methyl-sulfate to environment, technology is cleaned, the intermediate that generates changes into dicamba sodium salt with sodium hydroxide solution again, this technology is than traditional technology, productive rate also is improved, specifically implement like this: the alkylation process during improved dicamba 98 is produced, be 3,6-dichlorosalicylic acid and methyl-sulfate, the sodium hydroxide alkylation obtains the process of dicamba sodium salt, it is characterized in that 3,6-dichloro salicylic acid is dissolved in and drips methyl-sulfate in the organic solvent, reaction is 4-6 hour in the temperature below 100 ℃ or 100 ℃, add sodium hydroxide solution in the intermediate after steaming desolventizes again and obtain dicamba sodium salt, 3,6-dichlorosalicylic acid and methyl-sulfate, the mole proportioning of sodium hydroxide is 1: 2.0-2.2: 2.0-2.2.
The organic solvent that uses among the present invention can be toluene or acetone or dimethylbenzene or tetrahydrofuran (THF) or other analogue, and temperature of reaction is decided according to the organic solvent character of using, and needs to carry out under its boiling temperature, and preferred organic solvents is a phenyl ring class organic solvent.
For reaction can be carried out well, the concentration of sodium hydroxide solution is controlled at about 20-30%, and the intermediate after desolventizing with steaming (100 ℃) under boiling state refluxes and stirred 2-4 hour.
Dicamba sodium salt can obtain the weedicide dicamba 98 after acidifying.
In the alkylation process of the present invention, by in solvent, dripping methyl-sulfate, explained hereafter is cleaned, minimizing is to the murder by poisoning of environment, and for condition has been created in safety in production, this technology need not to operate under the temperature more than 100 degree, compare traditional technology, working condition is looser easy to control, and this technology has improved yield simultaneously, can reach more than 85%.
Embodiment
Embodiment 1, alkylation process during improved dicamba 98 is produced, 3,6-dichloro salicylic acid is dissolved in and drips methyl-sulfate in the toluene solvant, and reaction is 4-6 hour in 90-100 ℃ temperature, steams in the intermediate after desolventizing to add the sodium hydroxide solution that concentration is 20-30% again, 100 ℃ boiling state refluxes down and stirred 2-4 hour, obtain dicamba sodium salt, 3, the mole proportioning of 6-dichlorosalicylic acid and methyl-sulfate, sodium hydroxide is 1: 2.0: 2.0.
Embodiment 2, alkylation process during improved dicamba 98 is produced, 3,6-dichloro salicylic acid is dissolved in and drips methyl-sulfate in the acetone solvent, and reaction is 4-6 hour in 40-50 ℃ temperature, steams in the intermediate after desolventizing to add the sodium hydroxide solution that concentration is 20-30% again, 100 ℃ boiling state refluxes down and stirred 2-4 hour, obtain dicamba sodium salt, 3, the mole proportioning of 6-dichlorosalicylic acid and methyl-sulfate, sodium hydroxide is 1: 2.1: 2.1.
Embodiment 3, alkylation process during improved dicamba 98 is produced, 3,6-dichloro salicylic acid is dissolved in and drips methyl-sulfate in the tetrahydrofuran solvent, and reaction is 4-6 hour in 40-50 ℃ temperature, steams in the intermediate after desolventizing to add the sodium hydroxide solution that concentration is 20-30% again, 100 ℃ boiling state refluxes down and stirred 2-4 hour, obtain dicamba sodium salt, 3, the mole proportioning of 6-dichlorosalicylic acid and methyl-sulfate, sodium hydroxide is 1: 2.2: 2.2.
Embodiment 4, alkylation process during improved dicamba 98 is produced, 3,6-dichloro salicylic acid is dissolved in and drips methyl-sulfate in the xylene solvent, and reaction is 4-6 hour in 90-100 ℃ temperature, steams in the intermediate after desolventizing to add the sodium hydroxide solution that concentration is 20-30% again, 100 ℃ boiling state refluxes down and stirred 2-4 hour, obtain dicamba sodium salt, 3, the mole proportioning of 6-dichlorosalicylic acid and methyl-sulfate, sodium hydroxide is 1: 2.1: 2.1.
Claims (5)
1. the alkylation process during improved dicamba 98 is produced, be 3,6-dichlorosalicylic acid and methyl-sulfate, sodium hydroxide alkylation obtain the process of dicamba sodium salt, it is characterized in that 3,6-dichloro salicylic acid is dissolved in and drips methyl-sulfate in the organic solvent, reaction is 4-6 hour in the temperature below 100 or 100 ℃, add sodium hydroxide solution in the intermediate after steaming desolventizes again and obtain dicamba sodium salt, 3, the mole proportioning of 6-dichlorosalicylic acid and methyl-sulfate, sodium hydroxide is 1: 2.0-2.2: 2.0-2.2.
2. alkylation process according to claim 1 is characterized in that organic solvent is toluene or acetone or dimethylbenzene or tetrahydrofuran (THF) or analogue, and temperature of reaction is carried out under the boiling temperature of organic solvent.
3. alkylation process according to claim 1 is characterized in that organic solvent is a phenyl ring class organic solvent.
4. alkylation process according to claim 3 is characterized in that the temperature of reaction in the organic solvent is 90-100 ℃.
5. alkylation process according to claim 1, the concentration that it is characterized in that sodium hydroxide solution is 20-30%, the intermediate after desolventizing with steaming refluxes under 100 ℃ boiling state and stirred 2-4 hour.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610039170 CN1830942A (en) | 2006-03-27 | 2006-03-27 | Improved alkylation process for producing Mediben |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610039170 CN1830942A (en) | 2006-03-27 | 2006-03-27 | Improved alkylation process for producing Mediben |
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| Publication Number | Publication Date |
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| CN1830942A true CN1830942A (en) | 2006-09-13 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN 200610039170 Pending CN1830942A (en) | 2006-03-27 | 2006-03-27 | Improved alkylation process for producing Mediben |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103461331A (en) * | 2013-10-08 | 2013-12-25 | 山东潍坊润丰化工有限公司 | Method for preparing dicamba sodium salt preparations and prepared dicamba sodium salt preparations |
| US9695114B2 (en) | 2013-12-18 | 2017-07-04 | Monsanto Technology Llc | Processes for the diazotization of 2,5-dichloroanilines |
| US9856201B2 (en) | 2014-06-04 | 2018-01-02 | Monsanto Technology Llc | 3,6-dichlorosalicylic acid compounds and related synthetic processes |
| CN108290139A (en) * | 2015-10-01 | 2018-07-17 | 孟山都技术公司 | The catalytic hydrogenation of halonitro aromatic compound |
| US10343965B2 (en) | 2015-06-03 | 2019-07-09 | Monsanto Technology Llc | Separation of dichlorophenols |
-
2006
- 2006-03-27 CN CN 200610039170 patent/CN1830942A/en active Pending
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103461331A (en) * | 2013-10-08 | 2013-12-25 | 山东潍坊润丰化工有限公司 | Method for preparing dicamba sodium salt preparations and prepared dicamba sodium salt preparations |
| US9695114B2 (en) | 2013-12-18 | 2017-07-04 | Monsanto Technology Llc | Processes for the diazotization of 2,5-dichloroanilines |
| US9878978B2 (en) | 2013-12-18 | 2018-01-30 | Monsanto Technology Llc | Processes for the diazotization of 2,5-dichloroanilines |
| EP3438089A1 (en) | 2013-12-18 | 2019-02-06 | Monsanto Technology LLC | Processes for the diazotization of 2,5-dichloroanilines |
| US9856201B2 (en) | 2014-06-04 | 2018-01-02 | Monsanto Technology Llc | 3,6-dichlorosalicylic acid compounds and related synthetic processes |
| US10519092B2 (en) | 2014-06-04 | 2019-12-31 | Monsanto Technology Llc | 3,6-dichlorosalicylic acid compounds and related synthetic processes |
| US10807936B2 (en) | 2014-06-04 | 2020-10-20 | Monsanto Technology Llc | 3,6-dichlorosalicylic acid compounds and related synthetic processes |
| US10343965B2 (en) | 2015-06-03 | 2019-07-09 | Monsanto Technology Llc | Separation of dichlorophenols |
| CN108290139A (en) * | 2015-10-01 | 2018-07-17 | 孟山都技术公司 | The catalytic hydrogenation of halonitro aromatic compound |
| CN108290139B (en) * | 2015-10-01 | 2021-12-31 | 孟山都技术公司 | Process for the catalytic hydrogenation of halogenated nitroaromatics |
| US11225454B2 (en) | 2015-10-01 | 2022-01-18 | Monsanto Technology Llc | Process for catalytic hydrogenation of halonitroaromatics |
| US11820725B2 (en) | 2015-10-01 | 2023-11-21 | Monsanto Technology Llc | Process for catalytic hydrogenation of halonitroaromatics |
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