CN113651711A - Preparation method of 2, 6-difluorobenzamide - Google Patents
Preparation method of 2, 6-difluorobenzamide Download PDFInfo
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- CN113651711A CN113651711A CN202110857875.3A CN202110857875A CN113651711A CN 113651711 A CN113651711 A CN 113651711A CN 202110857875 A CN202110857875 A CN 202110857875A CN 113651711 A CN113651711 A CN 113651711A
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- difluorobenzamide
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- AVRQBXVUUXHRMY-UHFFFAOYSA-N 2,6-difluorobenzamide Chemical compound NC(=O)C1=C(F)C=CC=C1F AVRQBXVUUXHRMY-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 46
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 18
- 229910001220 stainless steel Inorganic materials 0.000 claims abstract description 18
- 239000010935 stainless steel Substances 0.000 claims abstract description 18
- BNBRIFIJRKJGEI-UHFFFAOYSA-N 2,6-difluorobenzonitrile Chemical compound FC1=CC=CC(F)=C1C#N BNBRIFIJRKJGEI-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000001035 drying Methods 0.000 claims abstract description 15
- 239000007788 liquid Substances 0.000 claims abstract description 14
- 239000002994 raw material Substances 0.000 claims abstract description 14
- 239000011780 sodium chloride Substances 0.000 claims abstract description 13
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 12
- 230000007062 hydrolysis Effects 0.000 claims abstract description 11
- 238000005406 washing Methods 0.000 claims abstract description 9
- 238000005185 salting out Methods 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 7
- 238000005086 pumping Methods 0.000 claims abstract description 7
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 5
- KTXFXDMDYZIXSJ-UHFFFAOYSA-N 2,4-difluorobenzamide Chemical compound NC(=O)C1=CC=C(F)C=C1F KTXFXDMDYZIXSJ-UHFFFAOYSA-N 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000008367 deionised water Substances 0.000 claims description 12
- 229910021641 deionized water Inorganic materials 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 5
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- 238000005112 continuous flow technique Methods 0.000 abstract description 2
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 8
- 239000012065 filter cake Substances 0.000 description 7
- 238000001514 detection method Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- GKPHNZYMLJPYJJ-UHFFFAOYSA-N 2,3-difluorobenzonitrile Chemical compound FC1=CC=CC(C#N)=C1F GKPHNZYMLJPYJJ-UHFFFAOYSA-N 0.000 description 2
- 229920002101 Chitin Polymers 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- JLZVIWSFUPLSOR-UHFFFAOYSA-N 2,3-difluorobenzoic acid Chemical compound OC(=O)C1=CC=CC(F)=C1F JLZVIWSFUPLSOR-UHFFFAOYSA-N 0.000 description 1
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical compound NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of 2, 6-difluorobenzamide, which is prepared by hydrolyzing 2, 6-difluorobenzonitrile at high temperature through a microchannel reactor and comprises the following steps: s1: preparing a raw material liquid: preparing 2, 6-difluorobenzonitrile aqueous solution for later use; s2: building equipment: the equipment consists of a high-pressure plunger pump and a stainless steel inserting piece type reactor; s3: high-temperature hydrolysis: pumping the raw material liquid into a stainless steel insert type reactor through a plunger pump for reaction, and flowing out of a post-treatment kettle for post-treatment; s4: and (3) post-treatment: adding sodium chloride solution into the treatment kettle for salting out, and then filtering, washing and drying to obtain the difluorobenzamide. The invention does not need to add any catalyst in the hydrolysis process, does not need acid-base neutralization in post-treatment, and has simple process, good purity and high yield. The invention uses continuous flow process to replace traditional high-pressure reaction kettle process, so that the reaction process is more controllable, safe and efficient.
Description
Technical Field
The invention relates to the field of pesticide preparation, and particularly relates to a preparation method of 2, 6-difluorobenzamide.
Background
The 2, 6-difluorobenzamide is a key intermediate for synthesizing the benzoylurea insecticides, belongs to a chitin synthesis inhibitor, kills insects by inhibiting the biosynthesis of chitin in the bodies of the insects, and has the characteristics of high insecticidal activity, wide insecticidal spectrum, low residual quantity, strong selectivity, safety to people and livestock and the like. Therefore, the market at home and abroad has an increasing demand for high-quality 2, 6-difluorobenzamide.
The synthesis methods reported at present mainly fall into two categories: (1) aminolysis of difluorobenzoic acid and derivatives thereof; (2) and (3) hydrolyzing difluorobenzonitrile. Wherein the hydrolysis method of the difluorobenzonitrile comprises the following steps: (1) acid catalyzed hydrolysis; (2) strong bases catalyze the hydrolysis of hydrogen peroxide. Because one of the two methods uses strong acid and one uses strong base, the post-treatment needs to use a large amount of acid and base for neutralization, thereby not only wasting a large amount of acid and base, but also generating a large amount of waste salt to pollute the environment.
Microfluidics refers to the technology of manipulating complex fluids at microscopic dimensions. In recent years, microfluidics has revolutionized the fields of chemistry, medicine, and life sciences, which is advantageous in that it is safe, efficient, and low cost. The invention develops a method for preparing 2, 6-difluorobenzamide by hydrolyzing 2, 6-difluorobenzonitrile by a continuous flow method by utilizing the characteristics of high mixing mass transfer rate, uniform reaction, continuity and stability, accurate reaction control and the like of a microfluid technology.
Disclosure of Invention
Based on the technical problems in the background art, the invention provides a preparation method of 2, 6-difluorobenzamide.
A preparation method of 2, 6-difluorobenzamide comprises the step of preparing the 2, 6-difluorobenzamide by hydrolyzing 2, 6-difluorobenzonitrile at a high temperature of 220-.
Preferably, the pyrohydrolysis reaction is carried out in a microchannel reactor.
Preferably, the microchannel reactor is a stainless steel insert sheet reactor, the reaction volume of the reactor is 300ml, the cooling volume of the reactor is 50ml, the temperature control range of the reactor is 50-300 ℃, and the pressure regulation range of the reactor is 0-6 Mpa.
Preferably, the reaction operation steps are as follows:
s1: preparing a raw material liquid: sequentially adding a certain amount of deionized water and 2, 6-difluorobenzonitrile into a 20L reaction kettle, and stirring and dissolving the mixture clear for later use;
s2: building equipment: the equipment consists of a high-pressure plunger pump and a stainless steel inserting piece type reactor, wherein the high-pressure plunger pump is connected with the inlet end of the stainless steel inserting piece type reactor, then the equipment is started, the temperature and the pressure are set to a reaction required value, and the reaction time is set by the flow rate of the pump;
s3: high-temperature hydrolysis: after the temperature and the pressure are stable in the step S2, pumping the raw material liquid in the step S1 into a reaction section in a stainless steel insert sheet type reactor through the plunger pump in the step S2 for reaction, cooling through a cooling end, and then flowing out of a post-treatment kettle;
s4: and (3) post-treatment: and (4) adding a sodium chloride solution into the post-treatment kettle in the step S3 for salting out, and then filtering, washing and drying to obtain the difluorobenzamide.
Preferably, the mass ratio of the deionized water to the 2, 6-difluorobenzonitrile is 2-4: 1.
Preferably, the reaction temperature is 240-260 ℃; the reaction pressure is 4-5 Mpa; the reaction time is 0.5-1.5 h.
Preferably, the weight ratio of the sodium chloride to the reaction liquid is 0.5-1: 10; the amount of water used in the water washing process is 10-30% of the weight of the solid; the drying temperature is 60-80 ℃; the drying time is 4-8 h.
Compared with the prior art, the invention has the beneficial effects that:
the method does not need to add any catalyst in the hydrolysis process, does not need acid-base neutralization in the post-treatment process, has simple process, good purity and high yield, and realizes green production. The invention uses the continuous flow process to replace the traditional high-pressure reaction kettle process, so that the reaction process is more controllable, safe and efficient, the production safety is improved, and the generation of byproducts is reduced.
The specific implementation mode is as follows:
the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1:
a preparation method of 2, 6-difluorobenzamide comprises the following operation steps in sequence:
s1: preparing a raw material liquid: respectively adding deionized water and 2, 6-difluorobenzonitrile into a reaction kettle, and uniformly stirring the deionized water and the 2, 6-difluorobenzonitrile according to the mass ratio of 2: 1 to prepare a solution for later use;
s2: building equipment: connecting a high-pressure plunger pump with a stainless steel inserting piece type reactor, setting the temperature of the reactor to be 240 ℃, setting the reaction pressure to be 4Mpa, and setting the flow rate of the plunger pump to be 2.5 ml/min;
s3: high-temperature hydrolysis: after the temperature and the pressure are stable, pumping the raw material liquid into a stainless steel inserted disc tubular reactor by using a plunger pump for reaction, and then flowing out of a post-treatment kettle through a cooling section and a back pressure valve;
s4: and (3) post-treatment: adding sodium chloride solution into the treatment kettle for salting out, wherein the weight ratio of sodium chloride to the reaction solution is 0.5:10, then filtering, and washing the filter cake with water, wherein the volume of the filter cake is 15% of the solid weight; the drying temperature is 60 ℃; the drying time was 8 h.
As a result: the calculated yield of the product obtained by post-treatment is 85.2%, and the purity of the product is 98.8% by liquid phase detection.
Example 2:
a preparation method of 2, 6-difluorobenzamide comprises the following operation steps in sequence:
s1: preparing a raw material liquid: respectively adding deionized water and 2, 6-difluorobenzonitrile into a reaction kettle, and uniformly stirring the deionized water and the 2, 6-difluorobenzonitrile according to the mass ratio of 2: 1 to prepare a solution for later use;
s2: building equipment: connecting a high-pressure plunger pump with a stainless steel inserting piece type reactor, setting the temperature of the reactor to be 280 ℃, setting the reaction pressure to be 4Mpa, and setting the flow rate of the plunger pump to be 5 ml/min;
s3: high-temperature hydrolysis: after the temperature and the pressure are stable, pumping the raw material liquid into a stainless steel inserted disc tubular reactor by using a plunger pump for reaction, and then flowing out of a post-treatment kettle through a cooling section and a back pressure valve;
s4: and (3) post-treatment: adding sodium chloride solution into the treatment kettle for salting out, wherein the weight ratio of sodium chloride to the reaction solution is 0.5:10, then filtering, and washing the filter cake with water, wherein the volume of the filter cake is 15% of the solid weight; the drying temperature is 60 ℃; the drying time was 8 h.
As a result: the calculated yield of the product obtained by post-treatment is 86.2%, and the purity of the product is 98.9% by liquid phase detection.
Example 3:
a preparation method of 2, 6-difluorobenzamide comprises the following operation steps in sequence:
s1: preparing a raw material liquid: respectively adding deionized water and 2, 6-difluorobenzonitrile into a reaction kettle, and uniformly stirring the deionized water and the 2, 6-difluorobenzonitrile according to the mass ratio of 3: 1 to prepare a solution for later use;
s2: building equipment: connecting a high-pressure plunger pump with a stainless steel inserting piece type reactor, setting the temperature of the reactor to be 240 ℃, setting the reaction pressure to be 4Mpa, and setting the flow rate of the plunger pump to be 2.5 ml/min;
s3: high-temperature hydrolysis: after the temperature and the pressure are stable, pumping the raw material liquid into a stainless steel inserted disc tubular reactor by using a plunger pump for reaction, and then flowing out of a post-treatment kettle through a cooling section and a back pressure valve;
s4: salting out treatment: adding a sodium chloride solution into the post-treatment kettle in the step S3 for salting out, wherein the weight ratio of sodium chloride to the reaction solution is 0.5:10, then filtering, and washing the filter cake with water, wherein the volume is 15% of the solid weight; the drying temperature is 60 ℃; the drying time was 8 h.
As a result: the calculated yield of the product obtained by post-treatment is 86.1%, and the purity of the product is 99.0% by liquid phase detection.
Example 4:
a preparation method of 2, 6-difluorobenzamide comprises the following operation steps in sequence:
s1: preparing a raw material liquid: respectively adding deionized water and 2, 6-difluorobenzonitrile into a reaction kettle, and uniformly stirring the deionized water and the 2, 6-difluorobenzonitrile according to the mass ratio of 3: 1 to prepare a solution for later use;
s2: building equipment: connecting a high-pressure plunger pump with a stainless steel inserting piece type reactor, setting the temperature of the reactor to be 260 ℃, setting the reaction pressure to be 5Mpa, and setting the flow rate of the plunger pump to be 2.5 ml/min;
s3: high-temperature hydrolysis: after the temperature and the pressure are stable, pumping the raw material liquid into a stainless steel inserted disc tubular reactor by using a plunger pump for reaction, and then flowing out of a post-treatment kettle through a cooling section and a back pressure valve;
s4: and (3) post-treatment: adding sodium chloride solution into the treatment kettle for salting out, wherein the weight ratio of sodium chloride to the reaction solution is 0.5:10, then filtering, and washing the filter cake with water, wherein the volume of the filter cake is 15% of the solid weight; the drying temperature is 60 ℃; the drying time was 8 h.
As a result: the calculated yield of the product obtained by post-treatment is 86.3%, and the purity of the product is 99.0% by liquid phase detection.
Claims (7)
1. A preparation method of 2, 6-difluorobenzamide is characterized in that 2, 6-difluorobenzamide is prepared by hydrolyzing 2, 6-difluorobenzonitrile at a high temperature, wherein the reaction temperature is 220-300 ℃, the reaction pressure is 4-6Mpa, and the reaction time is 0.5-2 h.
2. The process according to claim 1, wherein the hydrolysis reaction is carried out in a microchannel reactor.
3. The process according to claim 2, wherein said reaction is carried out in the presence of a 2, 6-difluorobenzamide: the microchannel reactor is a stainless steel insert reactor, the reaction volume of the reactor is 300ml, the cooling volume of the reactor is 50ml, the temperature control range of the reactor is 50-300 ℃, and the pressure regulation range of the reactor is 0-6 Mpa.
4. The method for preparing 2, 6-difluorobenzamide according to claim 1-3, characterized by: the reaction operation steps are as follows:
s1: preparing a raw material liquid: sequentially adding a certain amount of deionized water and 2, 6-difluorobenzonitrile into a 20L reaction kettle, and stirring and dissolving the mixture clear for later use;
s2: building equipment: the equipment consists of a high-pressure plunger pump and a stainless steel inserting piece type reactor, wherein the high-pressure plunger pump is connected with the inlet end of the stainless steel inserting piece type reactor, then the equipment is started, the temperature and the pressure are set to a reaction required value, and the reaction time is set by the flow rate of the pump;
s3: high-temperature hydrolysis: after the temperature and the pressure are stable in the step S2, pumping the raw material liquid in the step S1 into a reaction section in a stainless steel insert sheet type reactor through the plunger pump in the step S2 for reaction, cooling through a cooling end, and then flowing out of a post-treatment kettle;
s4: and (3) post-treatment: and (4) adding a sodium chloride solution into the post-treatment kettle in the step S3 for salting out, and then filtering, washing and drying to obtain the difluorobenzamide.
5. The process according to claim 4, wherein said reaction is carried out in the presence of a 2, 6-difluorobenzamide: in the step S1, the mass ratio of the deionized water to the 2, 6-difluorobenzonitrile is 2-4: 1.
6. The process according to claim 4, wherein said reaction is carried out in the presence of a 2, 6-difluorobenzamide: in the step S2, the reaction temperature is 240-260 ℃; the reaction pressure is 4-5 Mpa; the reaction time is 0.5-1.5 h.
7. The process according to claim 4, wherein said reaction is carried out in the presence of a 2, 6-difluorobenzamide: in the step S4, the weight ratio of the sodium chloride to the reaction liquid is 0.5-1: 10; the amount of water used in the water washing process is 10-30% of the weight of the solid; the drying temperature is 60-80 ℃; the drying time is 4-8 h.
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| CN202110857875.3A CN113651711A (en) | 2021-07-28 | 2021-07-28 | Preparation method of 2, 6-difluorobenzamide |
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|---|---|---|---|---|
| CN1861575A (en) * | 2006-05-08 | 2006-11-15 | 浙江大学 | Process of preparing 2,6-difluorobenzamide by 2.6-difluorobenz nitrile non catalyzing and hydrolyzing in near critical aqueous medium |
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Application publication date: 20211116 |