CN112358400A - Method for synthesizing acifluorfen by nitration in microreactor - Google Patents
Method for synthesizing acifluorfen by nitration in microreactor Download PDFInfo
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Abstract
The invention relates to a method for synthesizing acifluorfen by nitration in a microreactor. The method for synthesizing the acifluorfen in the microchannel reactor comprises the steps of pumping a nitrating agent consisting of a 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid solution containing raw materials, fuming sulfuric acid and fuming nitric acid into the microchannel reactor in parallel through a quantitative pump according to a certain proportion, and reacting to synthesize the 5- (2-chloro-4-trifluoromethylphenoxy) -2-nitrobenzoic acid (acifluorfen). The invention adopts the microchannel reactor to synthesize acifluorfen by nitration, the contact area is increased, and the mass transfer rate and the reaction rate are high; the heat transfer efficiency is increased, the reaction heat is quickly transferred, and the safety is improved; the continuous operation, the product quality is stable, the operation is flexible, and the amplification is easy; the reaction conversion rate can reach 99.19% and the reaction selectivity can reach 81.08% under the optimized condition.
Description
Technical Field
The invention belongs to the field of organic synthesis, and relates to a method for synthesizing acifluorfen by nitrating nitric-sulfuric mixed acid of 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid and a microreactor, namely, raw material etherate and nitric-sulfuric mixed acid are introduced into the microreactor according to a proportion to synthesize the acifluorfen.
Background
Acifluorfen is an important pesticide intermediate and is mainly used for synthesizing low-toxicity pesticides containing fluorine diphenyl ethers such as fomesafen and the like. The nitrating agent used for nitrating 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid to synthesize acifluorfen in industry is nitric acid and sulfuric acid mixed acid with higher concentration, most of nitration reaction kettles are intermittent kettles with mechanical stirring, and the intermittent kettles have the phenomena of uneven mixing, low heat transfer efficiency, easy occurrence of local material temperature flying rise, unstable product quality, low yield and the like. Moreover, the nitration reaction is an exothermic reaction, the reaction temperature is high, the reaction speed is high, and the explosion caused by temperature runaway is easy to cause; the substance to be nitrified contains inflammable substance or has toxicity, and is easy to cause fire when being improperly used and stored. In order to ensure the process safety, the existing 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid nitration process needs to be carried out in an intermittent stirring kettle at a low temperature, and the reaction time of one batch is usually 6-7 hours.
The microchannel reactor is a chemical process strengthening device, but at present, the technology for nitrifying the fluorine-containing diphenyl ether substances in the microchannel reactor is not reported.
Disclosure of Invention
The invention aims to solve the problems of harsh synthesis conditions, low safety and the like of the existing acifluorfen, and provides a method for obtaining acifluorfen with higher conversion rate and yield under mild conditions and ensuring the operation safety and a microreactor used by the method.
In order to achieve the purpose, the invention adopts the technical scheme that:
a method for synthesizing acifluorfen by nitration in a microreactor, comprising the following steps:
1) an organic mixed solution prepared from the 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid solid, a solvent and a water absorbent is an organic phase, and the mass fraction of the 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid solid is 2-20 wt%;
2) the method comprises the following steps of (1) taking mixed acid of nitric acid and sulfuric acid as a nitrating agent, wherein the mass ratio of the nitric acid to the sulfuric acid in the nitrating agent is 0.55-0.69;
3) respectively conveying the nitrating agent and the organic phase serving as reaction materials to a micro mixer through an injection pump, mixing the reaction materials and allowing the reaction materials to enter a microchannel reactor, and controlling the volume flow of the two phases so as to control the molar ratio of nitric acid to 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid to be 0.96-1.8;
4) the organic phase and the nitrating agent are subjected to nitration reaction in the microchannel reactor, flow out of an outlet and enter a separator; the residence time of the two materials in the reactor is 30-780 s, and the liquid flow airspeed of the microchannel reactor is 4.6-120 h-1；
5) The product in the separator is divided into an upper layer and a lower layer, the upper layer is an organic phase, the lower layer is an acid phase, and the separated organic phase is dried and washed to obtain the nitrated product acifluorfen.
In the method, the solvent adopted by the organic phase reaction materials can be dichloromethane, dichloroethane, chloroform and chlorobenzene, the dosage of the solvent is not less than 65 wt%, and the solvent dichloroethane is preferred; the water absorbent in the organic phase is acetic anhydride, and the mass content of the acetic anhydride is 0.65-5.3 wt%.
In the nitrating agent, nitric acid is fuming nitric acid with the mass content of more than or equal to 98 wt%, sulfuric acid is fuming sulfuric acid with the mass content of SO3The weight percentage of the nitric acid in the nitrating agent is more than or equal to 20 wt%, and the mass percentage of the nitric acid in the nitrating agent is 27-31 wt%.
The method of the invention is characterized in that the separator is placed at normal temperature, the upper organic phase is taken, and acifluorfen is obtained after drying, water washing and drying.
In the nitration method, the micro-mixer and the micro-channel reactor are arranged in a temperature control device, the mass fraction of 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid in an organic phase is 13-15.8 wt%, the molar weight ratio of nitric acid and sulfuric acid as a nitrating agent is 0.55-0.6, the molar ratio of nitric acid and 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid in the micro-channel reactor is 1.15-1.6, the reaction temperature is 10-35 ℃, and the retention time of a two-phase material in the micro-channel reactor is 780-780 s.
The inner diameter of the microchannel reactor for realizing the synthesis method is 0.25-1 mm, preferably 0.5-0.8 mm, and the length of the microchannel is 100-600 mm, preferably 400-600 mm; comprises two inlet channels which are communicated with a micro mixer, and the micro mixer is connected with a micro-channel reactor.
The inlet channel is made of PTFE, the micro mixer is made of ETFE, and the micro channel reactor is made of FEP; the length of the micro mixer is 25 mm, the inner diameter is 0.5 mm, and the inner diameter of the inlet channel is 3.17 mm.
The preferable molar weight ratio of the nitric acid and the sulfuric acid as the nitrating agent is 0.55, the mass fraction of 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid in an organic phase is 15.8 wt%, the molar ratio of the nitric acid to the 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid in the microchannel reactor is 1.15-1.4, the retention time of two-phase materials in the microchannel reactor is preferably 480-660 s, the reaction temperature is 10-20 ℃, the obtained reaction conversion rate is more than 90%, and the yield of a nitrated product reaches 80%.
The invention adopts the micro chemical technology to be applied to the mixed acid nitration reaction, and has the following advantages compared with the prior industrial nitration technology: the contact area of the mixed acid and the organic phase is large, the mass transfer rate and the reaction rate are high, and the reaction time is short; the heat transfer efficiency is increased, the reaction heat generated by the nitration reaction can be quickly transferred, large-scale refrigeration equipment is avoided, the cost is saved, and the reaction is safer; the continuous operation, the product quality is stable, the operation is flexible, and the amplification is easy; the reaction conversion rate can reach 99.19% and the reaction selectivity can reach 81.08% under the optimized condition.
Additional features and advantages of the invention will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the invention. The objectives and other advantages of the invention will be realized and attained by the structure particularly pointed out in the written description and claims hereof as well as the appended drawings.
Drawings
The accompanying drawings are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the principles of the invention and not to limit the invention.
FIG. 1 is a schematic flow diagram of a method of the present invention.
In the figure 1, 1 is an injector and a high-pressure injection pump which are filled with nitric acid and sulfuric acid mixed acid, 2 is an injector and a high-pressure injection pump which are filled with an organic phase, 3 is a micro mixer, 4 is a micro-channel reactor, the micro mixer connects a two-phase material inlet channel with a micro channel, the micro mixer 3 and the micro-channel reactor 4 are both arranged in a temperature control device, and a product flows into a separator from the micro-channel reactor 4.
Detailed Description
The present invention will now be described in more detail with reference to the accompanying drawings, in which preferred embodiments of the invention are shown, it being understood that one skilled in the art may modify the invention herein described while still achieving the beneficial results of the present invention. Accordingly, the following description should be construed as broadly as possible to those skilled in the art and not as limiting the invention.
In the interest of clarity, not all features of an actual implementation are described. In the following description, well-known functions or constructions are not described in detail since they would obscure the invention in unnecessary detail. It will of course be appreciated that in the development of any such actual embodiment, numerous implementation-specific details must be set forth in order to achieve the developer's specific goals.
As shown in fig. 1, the apparatus of the method provided by the present invention is: two high pressure injection pumps, wherein the injectors are respectively filled with mixed acid and organic phase raw materials, the mixed acid and the organic phase raw materials are introduced into a micro mixer through a pipeline, the outlet of the micro mixer is connected with the inlet of a micro channel, the two phases react in the micro channel, a reaction product flows into a separator from the outlet of the micro channel, and the organic phase is dried and washed to obtain acifluorfen. The micromixer and the microchannel reactor are both arranged in a temperature control device.
Example 1
Using 98 wt% fuming nitric acid and 20 wt% fuming sulfuric acid as follows: sulfuric acid molar ratio 0.55: 1, preparing mixed acid, wherein the temperature in the mixed acid preparation process is controlled to be 15-20 ℃. The mass fractions of 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid, acetic anhydride and dichloroethane in the organic phase were 15.8%, 5.3% and 78.9%, respectively.
Under the condition of 15 ℃, mixed acid and an organic phase are pumped into a micro mixer by a high-pressure injection pump through a pipeline, the micro mixer adopts a T-shaped mixing mode and is introduced into a micro-channel reactor, and the diameter of the micro channel is 500 mu m; the molar ratio of nitric acid to 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid was 1.4: 1, reaction retention time is 540 s, reaction products flow out of the reactor, the products are obtained through phase separation, drying and water washing, the reaction conversion rate reaches 99.19 percent, and the selectivity reaches 81.08 percent
Comparative example 1
The reaction temperature was changed to 20 ℃ and the other conditions were the same as in example 1. The reaction conversion was 94.61% with a selectivity of 77.2%.
Comparative example 2
The reaction temperature was changed to 10 ℃ and the other conditions were the same as in example 1. The reaction conversion was 95.3% with a selectivity of 76.32%.
Comparative example 3
The reaction temperature was changed to 40 ℃ and the other conditions were the same as in example 1. The conversion of the reaction was 100% and the selectivity was 69.95%.
Comparative example 4
Changing the molar ratio of nitric acid to 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid to 1.6: 1, the other conditions were the same as in example 1. The reaction conversion was 97.77% and the selectivity was 76.81%.
Comparative example 5
Changing the molar ratio of nitric acid to 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid to 1.32: 1, the other conditions were the same as in example 1. The reaction conversion was 97.44% and the selectivity was 80.13%.
Comparative example 6
Changing the molar ratio of nitric acid to 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid to 1.15: 1, the other conditions were the same as in example 1. The reaction conversion was 95.35% and the selectivity was 81.32%.
Example 2
The procedure is as in example 1, mixed acid nitric acid: the molar ratio of the sulfuric acid is unchanged, and the mass fraction of the 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid in the organic phase is 8 percent. The molar ratio of nitric acid to 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid at 10 ℃ is 0.96: 1, reaction residence time 30 s, reaction conversion 53.13% and selectivity 80.32%.
Example 3
The procedure is as in example 1, mixed acid nitric acid: the molar ratio of the sulfuric acid is unchanged, and the mass fraction of the 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid in the organic phase is 30 percent. The molar ratio of nitric acid to 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid at 35 ℃ is 1.8: 1, reaction residence time 780s, reaction conversion 99.98% and selectivity 69.21%.
Comparative example 7
Changing the molar ratio of nitric acid to 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid to 0.84: 1, the other conditions were the same as in example 2. The reaction conversion was 51.21% and the selectivity was 82.14%.
Comparative example 8
Changing the molar ratio of nitric acid to 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid to 2.0: 1, the other conditions were the same as in example 3. The reaction conversion was 100% and the selectivity 68.6%.
Comparative example 9
The reaction residence time was varied to 400 s and the conditions were otherwise the same as in example 2. The reaction conversion was 90.43% and the selectivity was 79.77%.
Comparative example 10
The reaction residence time was varied to 260 s and the conditions were otherwise the same as in example 3. The reaction conversion was 98.35% and the selectivity was 75.27%.
Example 4
The procedure is as in example 1, mixed acid nitric acid: the molar ratio of sulfuric acid is 0.69: 1, the mass fraction of 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid in the organic phase is 15.8%. The molar ratio of nitric acid to 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid at 35 ℃ is 1.6: 1, reaction residence time 480 s, reaction conversion 96.56% and selectivity 75.21%.
Comparative example 11
Changing mixed acid and nitric acid: the molar ratio of sulfuric acid is 0.73: 1, the other conditions were the same as in example 4. The reaction conversion was 97.91% with selectivity 70.79%.
Comparative example 12
Changing mixed acid and nitric acid: the molar ratio of sulfuric acid is 0.4: 1, the other conditions were the same as in example 4. The reaction conversion was 88.34% with a selectivity of 78.51%.
The invention provides a method for synthesizing acifluorfen by nitrating 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid in a microchannel reactor and a microreactor, wherein the method is characterized in that the microreactor is combined with a reaction for synthesizing the acifluorfen by nitrating the 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid, the microreactor and the method realize the rapid amplification (parallel amplification) of nitrating the 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid to synthesize the acifluorfen by utilizing a microchannel structure with the characteristic dimension of several micrometers to several millimeters, the mass and heat transfer rate of the nitration reaction is improved by 1 to 3 orders of magnitude compared with the traditional chemical equipment, and the problems of large heat release amount, large reaction temperature, high reaction efficiency and the like in the existing 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid mixed, Small contact area and poor operation safety.
Although the preferred embodiments of the present invention have been described in detail, the present invention is not limited to the details of the embodiments, and various equivalent modifications can be made within the technical spirit of the present invention, and the scope of the present invention is also within the scope of the present invention. It should be noted that the various features described in the above embodiments may be combined in any suitable manner without departing from the scope of the invention. The invention is not described in detail in order to avoid unnecessary repetition. In addition, any combination of the various embodiments of the present invention is also possible, and the same should be considered as the disclosure of the present invention as long as it does not depart from the spirit of the present invention.
Claims (8)
1. A method for synthesizing acifluorfen by nitration in a microreactor is characterized by comprising the following steps:
an organic mixed solution prepared from the 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid solid, a solvent and a water absorbent is an organic phase, wherein the mass content of the 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid solid is 8-30 wt%, the mass content of the solvent is not less than 65 wt%, and the mass content of the water absorbent is 0.65-5.3 wt%;
taking mixed acid of nitric acid and sulfuric acid as a nitrating agent, wherein the molar weight ratio of the nitric acid to the sulfuric acid in the nitrating agent is 0.55-0.69;
respectively conveying the nitrating agent and the organic phase serving as reaction materials to a micro mixer through an injection pump, mixing the reaction materials and allowing the reaction materials to enter a microchannel reactor, and controlling the volume flow of the two phases so as to control the molar ratio of nitric acid to 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid to be 0.96-1.8;
the organic phase and the nitrating agent are subjected to nitration reaction in the microchannel reactor, flow out of an outlet and enter a separator; the residence time of the two materials in the reactor is 30-780 s, and the liquid flow airspeed of the microchannel reactor is 4.6-120 h-1；
The product in the separator is divided into an upper phase and a lower phase, the upper phase is an organic phase, the lower phase is an acid phase, and the separated organic phase is dried and washed to obtain the nitrated product acifluorfen.
2. The method of claim 1, further comprising: the organic phase reaction material adopts any one of dichloromethane, dichloroethane, chloroform and chlorobenzene as a solvent;
the water absorbent in the organic phase is acetic anhydride.
3. The method of claim 1, further comprising: in the nitrating agent, nitric acid is fuming nitric acid with the mass content of more than or equal to 98 wt%, sulfuric acid is fuming sulfuric acid with the mass content of SO3The weight percentage of the nitric acid in the nitrating agent is more than or equal to 20 wt%, and the mass percentage of the nitric acid in the nitrating agent is 27-31 wt%.
4. The method of claim 2, further comprising: the solvent is dichloroethane.
5. The method of claim 1, further comprising: the micro mixer and the micro channel reactor are arranged in a temperature control device;
the mass fraction of the 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid in the organic phase is 13-15.8 wt%, and the molar weight ratio of nitric acid to sulfuric acid in the nitrating agent is 0.55-0.6;
the molar ratio of nitric acid to 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid in the microchannel reactor is 1.15-1.6, the reaction temperature is 10-35 ℃, and the residence time of two-phase materials in the microchannel reactor is 480-780 s.
6. The method of claim 1, further comprising: the microchannel reactor used to implement the synthesis process is as follows: the inner diameter is 0.25-1 mm, and the length of the micro-channel is 100-600 mm; comprises two inlet channels which are communicated with a micro mixer, and the micro mixer is connected with a micro-channel reactor.
7. The method of claim 6, wherein: the inlet channel is made of PTFE, the micro mixer is made of ETFE, and the micro channel reactor is made of FEP; the length of the micro mixer is 25 mm, the inner diameter is 0.5 mm, and the inner diameter of the inlet channel is 3.17 mm.
8. The method of claim 1 or 4, wherein: the molar weight ratio of nitric acid and sulfuric acid serving as a nitrating agent is 0.55, the mass fraction of 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid in an organic phase is 15.8 wt%, the molar ratio of nitric acid to 3- (2-chloro-4-trifluoromethylphenoxy) benzoic acid in a microchannel reactor is 1.15-1.4, the retention time of two-phase materials in the microchannel reactor is 480-660 s, the reaction temperature is 10-20 ℃, the obtained reaction conversion rate is more than 90%, and the yield of a nitrated product reaches 80%.
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Cited By (3)
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| CN114522447A (en) * | 2022-02-15 | 2022-05-24 | 清华大学 | Integrated multiphase continuous flow micro-chemical system |
| CN115093327A (en) * | 2022-06-20 | 2022-09-23 | 宁夏一帆生物科技有限公司 | Synthesis process of oxyfluorfen intermediate nitro diether |
| CN115353458A (en) * | 2022-07-08 | 2022-11-18 | 上海农帆生物科技有限公司 | Method for preparing aclonifen |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115353458A (en) * | 2022-07-08 | 2022-11-18 | 上海农帆生物科技有限公司 | Method for preparing aclonifen |
| CN115353458B (en) * | 2022-07-08 | 2023-09-29 | 上海农帆生物科技有限公司 | Method for preparing aclonifen |
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Application publication date: 20210212 |