CN107759513A - A kind of preparation method of the trifluoromethyl pyridine of 2 hydroxyl 6 - Google Patents
A kind of preparation method of the trifluoromethyl pyridine of 2 hydroxyl 6 Download PDFInfo
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- CN107759513A CN107759513A CN201711146933.1A CN201711146933A CN107759513A CN 107759513 A CN107759513 A CN 107759513A CN 201711146933 A CN201711146933 A CN 201711146933A CN 107759513 A CN107759513 A CN 107759513A
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- preparation
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- hydroxyls
- chloro
- trifluoromethylpyridines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
Abstract
The present invention relates to chemosynthesis technical field, particularly discloses a kind of preparation method of the trifluoromethyl pyridine of 2 hydroxyl 6.The preparation method of the trifluoromethyl pyridine of 2 hydroxyl 6, it is characterised in that：Using the trifluoromethyl pyridine of 2 chlorine 6 as raw material, the trifluoromethyl pyridine of 2 chlorine 6 and potassium hydroxide aqueous solution are mixed, confined reaction；After the completion of reaction, into reaction mass hydrochloric acid solution is added dropwise neutralizes, after through centrifuging, washing, secondary centrifuging, drying, product is made.Raw material of the present invention is simple and easy to get, and the addition of course of reaction organic solvent-free, process is simple, and production cost is low, and product yield is high, suitable for wide popularization and application.
Description
（One）Technical field
The present invention relates to chemosynthesis technical field, more particularly to a kind of preparation method of 2- hydroxyls -6- trifluoromethyl pyridines.
（Two）Background technology
2- hydroxyl -6- trifluoromethyl pyridines are the intermediates for synthesizing systemic fungicide pyridine oxygen polyester, and pyridine oxygen polyester is absorbability
Bactericide, controlling object wide spectrum, be mainly used in prevent and treat wheat class foliage disease such as, leaf blight, leaf rust, glume blight, brown spot,
Powdery mildew etc., compared with other methoxy acrylic bactericides, pyridine oxygen polyester is to wheat leaf blight, net blotch and moire disease
There is stronger therapeutic effect.ZEN 90160 was released by Syngenta Co., Ltd with 2001 in Europe.
In the prior art, synthesis 2- hydroxyl -6- trifluoromethyl pyridines typically use pyridine method and cyclization method, and industrialization is mainly
Based on pyridine method.Tao Shi in 1999 and the first fluoro- 6- trifluoromethyl pyridines of joint application hydroxylating 2- that just reaching produce 2- hydroxyls -6-
Trifluoromethyl pyridine patent.Chinese patent CN99810176.1 patentee Sinzeta Ltd. and road agricultural sciences are limited
Company, disclose jointly with the fluoro- 6- trifluoromethyl pyridines of 2- or the fluoro- 6- of 2- containing highest 50%2- chloro-6-trifluoromethylpyridines
Trifluoromethyl pyridine and 2- chloro-6-trifluoromethylpyridines mixture are the method that raw material prepares 2- hydroxyl -6- trifluoromethyl pyridines.
6- trifluoromethyl pyridines fluoro- compared to 2-, 2- chloro-6-trifluoromethylpyridine industrial productions are more easy to be made and cost is less than
The former.So this technology, which is hydrolysis ＞ 99%2- chloro-6-trifluoromethylpyridines, prepares 2- hydroxyl -6- trifluoromethyl pyridines.
（Three）The content of the invention
The present invention is in order to make up the deficiencies in the prior art, there is provided the 2- hydroxyl -6- trifluoros that a kind of step is simple, product yield is high
The preparation method of picoline.
The present invention is achieved through the following technical solutions：
A kind of preparation method of 2- hydroxyls -6- trifluoromethyl pyridines, it is characterised in that：Using 2- chloro-6-trifluoromethylpyridines as original
Material, specifically comprises the following steps：
（1）2- chloro-6-trifluoromethylpyridines and mass concentration are mixed for 20-50% potassium hydroxide aqueous solution, in 120-170
DEG C, confined reaction under pressure 0.3-0.8MPa；
（2）Reaction complete, sample it is qualified after, into reaction mass be added dropwise hydrochloric acid solution to pH value be 5-6, centrifuge afterwards, centrifugation
Product is made through washing, secondary centrifuging, drying in material afterwards.
The present inventor prepares 2- hydroxyl -6- trifluoromethyls by the reaction of 2- chloro-6-trifluoromethylpyridines and potassium hydroxide
Pyridine, reaction are carried out in closed container again, have certain pressure in course of reaction.
The present invention reaction equation be：
。
The present invention more excellent technical scheme be：
Step（1）In, the mol ratio of 2- chloro-6-trifluoromethylpyridines and potassium hydroxide is 1:2.1-2.6；In order that react
Entirely, 1.05-1.3 times of the usage amount Choice Theory value of potassium hydroxide, the state in excess.The concentration of potassium hydroxide aqueous solution
It can be determined according to the solvent of reaction vessel and the pressure-resistant situation of reaction vessel, the higher potassium hydroxide of concentration relative can be improved and set
Standby utilization rate, production efficiency is improved, while at a temperature of also making equivalent responses, reaction pressure is lower.
The confined reaction time is 8 hours, is sufficiently mixed raw material, and feed stock conversion improves.
Step（2）In, reaction mass samples the content that qualified standard is 2- chloro-6-trifluoromethylpyridines in material and is less than
0.1%；Reaction mass is first diluted with water before hydrochloric acid solution is added dropwise；What slurry concentration suitably adjusts after visually being neutralized with regard to love water, water
What slurry overrich is unfavorable for stirring and discharged amount very little, and water crosses the increase of ambassador's wastewater flow rate.
Hydrochloric acid controls reaction mass temperature to be less than 30 DEG C during being added dropwise, and 5-10 DEG C of centrifugation is cooled to after being added dropwise to complete, with
Continuous washing and centrifugation after an action of the bowels.
Raw material of the present invention is simple and easy to get, and the addition of course of reaction organic solvent-free, process is simple, and production cost is low, and product is received
Rate is high, suitable for wide popularization and application.
（Four）Brief description of the drawings
The present invention is further illustrated below in conjunction with the accompanying drawings.
Fig. 1 is the process flow diagram of the present invention.
（Five）Embodiment
The present invention is further described below in conjunction with embodiment.
Embodiment：
By 2- chloro-6-trifluoromethylpyridines（≥99%）750kg（4.01Kmol）Reactor is added with 1100kg-2000kg water, then
Add potassium hydroxide（95%）550kg（9.15 Kmol）, reactor is put into after potassium hydroxide can also being first configured into the aqueous solution
It is interior, 120-170 DEG C is warming up to, stirring reaction 8 hours under pressure about 0.3-0.8MPa, it is qualified to sample（The chloro- 6- trifluoros of raw material 2-
Picoline content is less than 0.1%）After be transferred to neutralization kettle, be transferred to before neutralize kettle first add a certain amount of water, depending on neutralize kettle volume add
1500-3000kg water, neutralize what slurry concentration after kettle amount of water visually neutralizes and suitably adjust, what slurry overrich is unfavorable for water very little
Stirring and discharging.Water crosses the increase of ambassador's wastewater flow rate.
Material is added dropwise hydrochloric acid and is neutralized to pH value after being transferred to be 5-6, and N-process temperature control is less than 30 DEG C, cooled after neutralization
To 5-10 DEG C of centrifugation, material enters washing kettle after centrifugation, adds 2000kg water to carry out material after secondary centrifuging, secondary centrifuging after washing
Drying is gone, dries obtained 2- hydroxyl -6- trifluoromethyl pyridines.
Claims (6)
- A kind of 1. preparation method of 2- hydroxyls -6- trifluoromethyl pyridines, it is characterised in that：Using 2- chloro-6-trifluoromethylpyridines as Raw material, specifically comprise the following steps：（1）By the potassium hydroxide water that 2- chloro-6-trifluoromethylpyridines and mass concentration are 20-50% Solution mixes, the confined reaction under 120-170 DEG C, pressure 0.3-0.8MPa；（2）Reaction completes, sample it is qualified after, toward reactant It is 5-6 that hydrochloric acid solution to pH value is added dropwise in material, is centrifuged afterwards, and product is made through washing, secondary centrifuging, drying in material after centrifugation.
- 2. the preparation method of 2- hydroxyls -6- trifluoromethyl pyridines according to claim 1, it is characterised in that：Step（1） In, the mol ratio of 2- chloro-6-trifluoromethylpyridines and potassium hydroxide is 1:2.1-2.6.
- 3. the preparation method of 2- hydroxyls -6- trifluoromethyl pyridines according to claim 1, it is characterised in that：Step（1） In, the confined reaction time is 8 hours.
- 4. the preparation method of 2- hydroxyls -6- trifluoromethyl pyridines according to claim 1, it is characterised in that：Step（2） In, reaction mass samples the content that qualified standard is 2- chloro-6-trifluoromethylpyridines in material and is less than 0.1%.
- 5. the preparation method of 2- hydroxyls -6- trifluoromethyl pyridines according to claim 1, it is characterised in that：Step（2） In, reaction mass is first diluted with water before hydrochloric acid solution is added dropwise.
- 6. the preparation method of 2- hydroxyls -6- trifluoromethyl pyridines according to claim 1, it is characterised in that：Step（2） In, hydrochloric acid controls reaction mass temperature to be less than 30 DEG C during being added dropwise, and 5-10 DEG C of centrifugation is cooled to after being added dropwise to complete.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711146933.1A CN107759513A (en) | 2017-11-17 | 2017-11-17 | A kind of preparation method of the trifluoromethyl pyridine of 2 hydroxyl 6 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711146933.1A CN107759513A (en) | 2017-11-17 | 2017-11-17 | A kind of preparation method of the trifluoromethyl pyridine of 2 hydroxyl 6 |
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| CN107759513A true CN107759513A (en) | 2018-03-06 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113185455A (en) * | 2020-01-14 | 2021-07-30 | 新发药业有限公司 | Preparation method of 2-hydroxy-6-trifluoromethylpyridine |
| CN114434930A (en) * | 2022-02-17 | 2022-05-06 | 宁波勤邦新材料科技有限公司 | Heddle base film and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1314889A (en) * | 1998-09-03 | 2001-09-26 | 曾尼卡有限公司 | Chemical process for preparing 2-hydroxy-6-trifluoro methylpyridine |
| CN106866512A (en) * | 2017-03-09 | 2017-06-20 | 常州沃腾化工科技有限公司 | A kind of preparation method of the trifluoromethyl pyridine of 2 hydroxyl 6 |
-
2017
- 2017-11-17 CN CN201711146933.1A patent/CN107759513A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1314889A (en) * | 1998-09-03 | 2001-09-26 | 曾尼卡有限公司 | Chemical process for preparing 2-hydroxy-6-trifluoro methylpyridine |
| CN106866512A (en) * | 2017-03-09 | 2017-06-20 | 常州沃腾化工科技有限公司 | A kind of preparation method of the trifluoromethyl pyridine of 2 hydroxyl 6 |
Non-Patent Citations (1)
| Title |
|---|
| JAVIER PARRA 等: "Exploring alternative hapten tethering sites for high-affinity anti-picoxystrobin antibody generation", 《ANALYTICAL BIOCHEMISTRY》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113185455A (en) * | 2020-01-14 | 2021-07-30 | 新发药业有限公司 | Preparation method of 2-hydroxy-6-trifluoromethylpyridine |
| CN114434930A (en) * | 2022-02-17 | 2022-05-06 | 宁波勤邦新材料科技有限公司 | Heddle base film and preparation method thereof |
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