Apparatus for the acylation synthesis of oxazolidinyl acetonitrile
By designing an acylation synthesis device for oxazolidinium, and connecting a series of reactors, desolvation reactors, and other equipment, the problem of difficult product purification and separation in the synthesis of oxazolidinium was solved, and safe and efficient operation for industrial production was achieved.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Utility models(China)
- Current Assignee / Owner
- INNER MONGOLIA KUNPENG NEW MATERIALS CO LTD
- Filing Date
- 2025-07-15
- Publication Date
- 2026-06-30
AI Technical Summary
Existing methods for synthesizing oxazolidinone suffer from difficulties in product purification and separation, as well as safety hazards, making them unsuitable for industrial application.
An apparatus for the acylation synthesis of oxazolidinyl acetochlor is provided, comprising a first reaction vessel, a second reaction vessel, a neutralization vessel, a water washing vessel, and a solvent removal vessel connected in series. Through the coordinated use of these devices, the steps of generating, reacting, acidifying, neutralizing, and desolvating under reduced pressure are realized to obtain dried oxazolidinyl acetochlor.
It enables easy-to-operate industrial production of oxazolidinone, solves the problem of difficult product purification and separation, and has both safety and high efficiency.
Smart Images
Figure CN224422867U_ABST
Abstract
Description
Technical Field
[0001] This application relates to the field of pesticide production technology, and in particular to an apparatus for the acylation synthesis of oxazolidinone. Background Technology
[0002] Metamifop is an aryloxyphenoxypropionate herbicide, marketed under the brand name Hanqiuhao, with CAS number 256412-89-2. Its target is acetyl-CoA carboxylase, which inhibits the production of malonyl-CoA, thus hindering the further synthesis of fatty acids, leading to the formation of oleic acid, linoleic acid, linolenic acid, the waxy layer, and the cuticle. This results in rapid damage to the membrane structure of monocotyledonous plants, increased permeability, and ultimately plant death. Due to its low toxicity, high efficiency, low residue, and broad miscibility, it has become one of the most commonly used herbicides for controlling annual grass weeds and holds promise for use on other crops and lawns, showing great potential for future development.
[0003] Existing methods for synthesizing oxazolidinyl mainly include methods using hydroquinone as a raw material, methods using iodomethane as a raw material, and methods using N-methyl-o-fluoroaniline as a raw material. Among them, the hydroquinone method and the iodomethane method are difficult to apply industrially due to difficulties in product purification and separation or the existence of safety hazards. Therefore, it is necessary to develop a process suitable for industrial synthesis of oxazolidinyl. Utility Model Content
[0004] This application provides an apparatus for the acylation synthesis of oxazolidinone, thereby providing an effective route for the industrial production of oxazolidinone.
[0005] This application provides an apparatus for the acylation synthesis of oxazolidinyl acetochlor, comprising a first reaction vessel, a second reaction vessel, a neutralization vessel, a water washing vessel, and a solvent removal vessel connected in series.
[0006] The first reactor is also connected to the first substrate storage tank and the thionyl chloride storage tank, respectively.
[0007] The first and second reaction vessels are connected by a peristaltic pump;
[0008] The second reactor is also connected to the second substrate storage tank and the acid metering pump, respectively.
[0009] The neutralization vessel is also connected to an alkali metering pump and a wastewater treatment device;
[0010] The washing vessel is also connected to a clean water storage tank and a wastewater treatment device;
[0011] The solvent removal vessel is also connected in sequence to the first condenser and the first vacuum unit, and the first condenser is also connected to the solvent recovery tank.
[0012] Optionally, the first reactor is also connected in sequence to the second condenser and the second vacuum unit;
[0013] The second condenser is connected to the thionyl chloride recovery tank.
[0014] Optionally, both the first vacuum unit and the second vacuum unit are connected to the exhaust gas treatment device.
[0015] Optionally, the desolventizing vessel is also connected to a crystallizing vessel, a centrifuge, and a pure product storage silo;
[0016] The centrifuge is also connected to the mother liquor storage tank, which in turn is connected to the crystallization kettle.
[0017] Optionally, the wastewater treatment device includes a filter, a reverse osmosis unit, a multi-effect evaporator, a thickener, a crystallization tank, a filter press, and a salt storage tank connected in series.
[0018] The filter press is also connected to a filtrate storage tank, which in turn is connected to a thickener.
[0019] Optionally, a dripping pipe is provided in the upper part of the second reaction vessel, and the dripping pipe is connected to a peristaltic pump;
[0020] The drip tube has a ring structure and is fixed inside the upper head of the second reactor by a connecting beam;
[0021] The lower surface of the drip tube is provided with drip heads at equal intervals.
[0022] Optionally, the exhaust gas treatment device is an incinerator or an activated carbon adsorption tower.
[0023] This application provides an apparatus for the acylation synthesis of oxazolidinone. A first reaction vessel is used to react a first substrate with thionyl chloride to generate the corresponding acyl chloride. The resulting acyl chloride is then added to a second reaction vessel to react with a second substrate to obtain oxazolidinone. Acid is then added via an acid metering pump for acidification. The acidified reaction is then transferred to a neutralization vessel for neutralization with alkali. Finally, the neutralized reaction solution is subjected to desolvation under reduced pressure in a solvent removal vessel to obtain dried oxazolidinone. The apparatus of this application, through the combined use of the above equipment, provides an effective and industrially feasible route for the production of oxazolidinone, and is characterized by its ease of operation. Attached Figure Description
[0024] To more clearly illustrate the technical solutions in the embodiments of this application or the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.
[0025] Figure 1A schematic diagram of an apparatus for the acylation synthesis of oxazolidinyl acetochlor is provided for one embodiment of this application;
[0026] Figure 2 A schematic diagram of an apparatus for the acylation synthesis of oxazolidinyl acetochlor is provided for another embodiment of this application;
[0027] Figure 3 This is a schematic diagram of a wastewater treatment device provided in one embodiment of this application;
[0028] Figure 4 This is a schematic diagram of the structure of a second reaction vessel provided in an embodiment of this application;
[0029] Figure 5 This is a schematic diagram of the internal cross-sectional structure of a second reactor provided in an embodiment of this application.
[0030] Instruction manual illustrations:
[0031] 1. First reaction vessel; 2. Second reaction vessel; 3. Neutralization vessel; 4. Washing vessel; 5. Desolventizing vessel; 6. Wastewater treatment device; 7. Crystallization vessel; 10. Peristaltic pump; 11. First substrate storage tank; 12. Thionyl chloride storage tank; 13. Second condenser; 14. Second vacuum unit; 15. Thionyl chloride recovery tank; 16. Tail gas treatment device; 21. Second substrate storage tank; 22. Acid metering pump; 31. Alkali metering pump; 4 1. Clear water storage tank; 51. First condenser; 52. First vacuum unit; 53. Solvent recovery tank; 61. Filter; 62. Reverse osmosis unit; 63. Multi-effect evaporator; 64. Thickener; 65. Crystallization tank; 66. Salt storage tank; 67. Filtrate storage tank; 71. Centrifuge; 72. Pure product storage tank; 73. Mother liquor storage tank; 200. Drip pipe; 201. Connecting beam; 202. Dripper; 651. Filter press. Detailed Implementation
[0032] To make the objectives, technical solutions, and advantages of the embodiments of this application clearer, the technical solutions in the embodiments of this application are described clearly and completely below. Obviously, the described embodiments are only some embodiments of this application, not all embodiments. Based on the embodiments in this application, all other embodiments obtained by those skilled in the art without creative effort are also within the scope of protection of this application.
[0033] like Figure 1 As shown, this application provides an apparatus for the acylation synthesis of oxazolidinyl acetochlor, comprising a first reaction vessel 1, a second reaction vessel 2, a neutralization vessel 3, a water washing vessel 4, and a solvent removal vessel 5 connected in series.
[0034] The first reaction vessel 1 is also connected to the first substrate storage tank 11 and the thionyl chloride storage tank 12, respectively;
[0035] The first reactor 1 and the second reactor 2 are connected by a peristaltic pump 10;
[0036] The second reactor 2 is also connected to the second substrate storage tank 21 and the acid metering pump 22, respectively.
[0037] The neutralization vessel 3 is also connected to the alkali metering pump 31 and the wastewater treatment device 6, respectively;
[0038] The washing vessel 4 is also connected to the clean water storage tank 41 and the wastewater treatment device 6 respectively;
[0039] The solvent removal vessel 5 is also connected in sequence to the first condenser 51 and the first vacuum unit 52, and the first condenser 51 is also connected to the solvent recovery tank 53.
[0040] In use, the first substrate ((R)-2-[4-(6-chloro-1,3-benzoxazol-2-yloxy)phenoxy]propionic acid in this application) and the solvent (dichloroethane in this application) in the first substrate storage tank 11 are added to the first reaction vessel 1. Then, thionyl chloride in the thionyl chloride storage tank 12 is added to the first reaction vessel 1 in a certain proportion (the molar ratio of thionyl chloride to the first substrate is 1.1~1.2∶1). Then, a catalytic amount of DMF (1~5% of the molar amount of thionyl chloride) and an acid-binding agent (triethylamine) are added. The reaction system is heated to 70~72°C and reacted until the content of the first substrate is below 1%. Then, the first reaction liquid in the first reaction vessel 1 is cooled to 0~5°C for later use.
[0041] The second substrate, along with the solvent (dichloroethane) and acid-binding agent (triethylamine) from the second substrate storage tank 21, is added to the second reaction vessel 2, and the temperature is lowered to 0-5°C. At this time, the first reaction solution from the first reaction vessel 1 is added dropwise to the second reaction vessel 2 using a peristaltic pump 10 according to a certain ratio. After the addition is complete, the reaction is carried out at 0-5°C until the residual amount of the second substrate is less than 5%. After the reaction is completed, an appropriate amount of water is added to the second reaction vessel 2 to destroy the unreacted acyl chloride (i.e., the feed solution output from the first reaction vessel 1). Then, acid (concentrated hydrochloric acid or concentrated sulfuric acid) is added through the acid metering pump 22. The pH of the system is adjusted to approximately 1. The organic phase is transferred to neutralization vessel 3 via separation. Alkali solution (such as an aqueous solution of saturated sodium carbonate or saturated sodium bicarbonate) is added using alkali metering pump 31 to wash until weakly alkaline. After separation, the organic phase is transferred to water washing vessel 4, and water is added through water storage tank 41 to wash the organic phase until neutral. After separation, the organic phase is loaded into solvent removal vessel 5. Vacuum distillation is performed on the solvent removal vessel using first vacuum unit 52 and first condenser 51. The distilled solvent is condensed in first condenser 51 and recovered to solvent recovery tank 53. Crude acetamide is obtained after solvent removal. Further purification requires recrystallization.
[0042] The aqueous phase separated in neutralization vessel 3 and washing vessel 4 is transferred to wastewater treatment device 6 for further treatment.
[0043] This application provides an apparatus for the acylation synthesis of oxazolidinone. A first reaction vessel 1 reacts a first substrate with thionyl chloride to generate the corresponding acyl chloride. The resulting acyl chloride is then added to a second reaction vessel 2 to react with a second substrate to obtain oxazolidinone. Acid is then added via an acid metering pump 22 for acidification. The acidified reaction is transferred to a neutralization vessel 3 for neutralization with alkali. The neutralized reaction solution is then subjected to desolvation under reduced pressure in a desolvation vessel 5 to obtain dried oxazolidinone. The apparatus of this application, through the combined use of the above equipment, provides an effective and industrially feasible route for the production of oxazolidinone, and is characterized by its ease of operation.
[0044] like Figure 2 As shown, optionally, the first reactor 1 is also connected in sequence to the second condenser 13 and the second vacuum unit 14;
[0045] The second condenser 13 is connected to the thionyl chloride recovery tank 15.
[0046] At this point, the second vacuum unit 14 is activated to evacuate the first reaction vessel 1 through the second condenser 13, distilling off the thionyl chloride that did not react completely during the reaction. The distilled thionyl chloride is condensed into liquid in the second condenser 13 and collected in the thionyl chloride recovery tank 15. The uncondensed tail gas is discharged by the second vacuum unit 14. After the thionyl chloride is distilled off, the vacuum is broken, and the first reaction liquid in the first reaction vessel 1 is cooled to 0~5℃ for later use.
[0047] like Figure 2 As shown, optionally, both the first vacuum unit 52 and the second vacuum unit 14 are connected to the exhaust gas treatment device 16.
[0048] Optionally, the desolventizing vessel 5 is also connected to the crystallizing vessel 7, the centrifuge 71, and the pure product storage tank 72;
[0049] The centrifuge 71 is also connected to the mother liquor storage tank 73, which is also connected to the crystallization vessel 7.
[0050] During recrystallization, the crude cyhalothrin obtained from the solvent removal process is added to crystallization vessel 7. A solvent (such as a mixture of isopropanol and water) is added and the mixture is heated to form a supersaturated solution. The solution is then cooled to allow the cyhalothrin to crystallize. After complete crystallization, the mother liquor containing the crystals is sent to centrifuge 71 for centrifugation to separate the wet cyhalothrin and the crystallization mother liquor. The wet cyhalothrin is transferred to the pure product storage silo 72 and dried to obtain the finished cyhalothrin. The crystallization mother liquor is then returned to crystallization vessel 7 for reuse.
[0051] like Figure 3As shown, optionally, the wastewater treatment device 6 includes a filter 61, a reverse osmosis device 62, a multi-effect evaporator 63, a thickener 64, a crystallization tank 65, a filter press 651, and a salt storage tank 66 connected in series.
[0052] The filter press 651 is also connected to the filtrate storage tank 67, which is also connected to the thickener 64.
[0053] The aqueous phase after separation in neutralization tank 3 and washing tank 4 is transferred to wastewater treatment device 6 for treatment. This wastewater is first filtered through filter 61 (security filter) and then enters reverse osmosis device 62. It is filtered through reverse osmosis membrane to obtain fresh water, which is then recycled for use within the plant. The concentrated water is transferred to multi-effect evaporator 63 for evaporation and concentration until crystals precipitate. Then it is transferred to thickener 64 for sedimentation. The crystal-containing liquid at the bottom of thickener 64 is transferred to crystallization tank 65 for further crystallization. The washed liquid is then transferred to filter press 651 for pressure filtration to separate the crystals (salt). The separated crystals are transferred to salt storage tank 66 for temporary storage, while the mother liquor enters filtrate storage tank 67 and is then returned to thickener 64 for recovery.
[0054] like Figure 4 and Figure 5 As shown, optionally, a dripping pipe 200 is provided in the upper part of the second reaction vessel 2, and the dripping pipe 200 is connected to the peristaltic pump 10;
[0055] The drip tube 200 has a ring structure and is fixed inside the upper head of the second reactor 2 by a connecting beam 201;
[0056] Droppers 202 are evenly spaced on the lower surface of the dripping tube 200.
[0057] In this application, during use, the first reaction liquid, supplied by the peristaltic pump 10, is introduced into the annular dripping pipe 200 and then into the dripper 202 (the structure of which can be referenced from drip irrigation drippers, except that the material used is a material resistant to organic solvents, such as polytetrafluoroethylene or stainless steel) and dripped into the second reaction vessel 2. In this application, the dripping pipe 200 has an annular structure, and during installation, the stirring shaft of the agitator is positioned through the center of the dripping pipe 200.
[0058] Optionally, the exhaust gas treatment device 16 is an incinerator or an activated carbon adsorption tower.
[0059] In this application, the exhaust gas treatment device 16 is an incinerator or an activated carbon adsorption tower, which can incinerate or adsorb the exhaust gas for harmless treatment.
[0060] An apparatus for the acylation synthesis of acetochlor, the working process of which is as follows:
[0061] In use, the first substrate ((R)-2-[4-(6-chloro-1,3-benzoxazol-2-yloxy)phenoxy]propionic acid in this application) and solvent (dichloroethane in this application) from the first substrate storage tank 11 are added to the first reaction vessel 1. Then, thionyl chloride from the thionyl chloride storage tank 12 is added to the first reaction vessel 1 in a certain ratio (the molar ratio of thionyl chloride to the first substrate is 1.1~1.2∶1), and then a catalytic amount of DMF (chlorine chloride) is added. The reaction system is heated to 70-72°C with 1-5% (molar amount) of thionyl chloride and a binding agent (triethylamine) until the content of the first substrate is below 1%. At this point, the second vacuum unit 14 is turned on to evacuate the first reaction vessel through the second condenser 13, distilling off the thionyl chloride that did not react completely during the reaction. The distilled thionyl chloride is condensed into liquid in the second condenser 13 and collected in the thionyl chloride recovery tank 15. The uncondensed tail gas is discharged by the second vacuum unit 14. After the thionyl chloride is distilled off, the vacuum is broken, and the first reaction liquid in the first reaction vessel 1 is cooled to 0-5°C for later use.
[0062] The second substrate, along with the solvent (dichloroethane) and acid-binding agent (triethylamine) from the second substrate storage tank 21, is added to the second reaction vessel 2, and the temperature is lowered to 0-5°C. At this time, the first reaction solution from the first reaction vessel 1 is added dropwise to the second reaction vessel 2 via the peristaltic pump 10 according to a certain ratio. Specifically, the first reaction solution delivered by the peristaltic pump 10 is input into the annular dripping pipe 200, and then into the dripper 202 (the structure can be referenced from drip irrigation drippers, except that the material used is a material resistant to organic solvents, such as polytetrafluoroethylene or stainless steel) and dripped into the second reaction vessel 2. After the dripping is completed, the reaction is carried out at 0-5°C until the residual amount of the second substrate is less than 5%. After the reaction is completed, an appropriate amount of water is added to the second reaction vessel 2 to remove the unreacted acyl chloride (i.e., the residue delivered in the first reaction vessel 1). The feed solution is broken down, and acid (concentrated hydrochloric acid or concentrated sulfuric acid) is added through acid metering pump 22 to adjust the pH of the system to about 1. The organic phase is separated and transferred to neutralization vessel 3. Alkali solution (such as an aqueous solution of saturated sodium carbonate or saturated sodium bicarbonate) is added through alkali metering pump 31 to wash until weakly alkaline. After separation, the organic phase is transferred to water washing vessel 4. Water is added through water storage tank 41 to wash the organic phase until neutral. After separation, the organic phase is loaded into desolventizing vessel 5. The first vacuum unit 52 is used to perform vacuum distillation on desolventizing vessel 5 through the first condenser 51. The distilled solvent is condensed in the first condenser 51 and recovered to solvent recovery tank 53. The tail gas that is not condensed during the desolventizing process is discharged by the first vacuum unit 52 to the tail gas treatment device 16 for treatment. Crude acetamide can be obtained after desolventizing. If further purification is required, a recrystallization process is needed.
[0063] During recrystallization, the crude cyhalothrin obtained from the solvent removal process is added to crystallization vessel 7. A solvent (such as a mixture of isopropanol and water) is added and the mixture is heated to form a supersaturated solution. The solution is then cooled to allow the cyhalothrin to crystallize. After complete crystallization, the mother liquor containing the crystals is sent to centrifuge 71 for centrifugation to separate the wet cyhalothrin and the crystallization mother liquor. The wet cyhalothrin is transferred to the pure product storage silo 72 and dried to obtain the finished cyhalothrin. The crystallization mother liquor is then returned to crystallization vessel 7 for reuse.
[0064] The aqueous phase after separation in neutralization tank 3 and washing tank 4 is transferred to wastewater treatment device 6 for treatment. This wastewater is first filtered through filter 61 (security filter) and then enters reverse osmosis device 62. It is filtered through reverse osmosis membrane to obtain fresh water, which is then recycled for use within the plant. The concentrated water is transferred to multi-effect evaporator 63 for evaporation and concentration until crystals precipitate. Then it is transferred to thickener 64 for sedimentation. The crystal-containing liquid at the bottom of thickener 64 is transferred to crystallization tank 65 for further crystallization. The washed liquid is then transferred to filter press 651 for pressure filtration to separate the crystals (salt). The separated crystals are transferred to salt storage tank 66 for temporary storage, while the mother liquor enters filtrate storage tank 67 and is then returned to thickener 64 for recovery.
[0065] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of this application, and are not intended to limit them. Although this application has been described in detail with reference to the foregoing embodiments, those skilled in the art should understand that modifications can still be made to the technical solutions described in the foregoing embodiments, or equivalent substitutions can be made to some or all of the technical features therein. Such modifications or substitutions do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of this application.
Claims
1. An apparatus for the acylation synthesis of oxazolidinyl acetonide, characterized in that, It includes a first reactor (1), a second reactor (2), a neutralization reactor (3), a water washing reactor (4), and a desolventizing reactor (5) connected in series. The first reactor (1) is also connected to the first substrate storage tank (11) and the thionyl chloride storage tank (12), respectively; The first reactor (1) and the second reactor (2) are connected by a peristaltic pump (10); The second reactor (2) is also connected to the second substrate storage tank (21) and the acid metering pump (22), respectively; The neutralization vessel (3) is also connected to the alkali metering pump (31) and the wastewater treatment device (6); The washing tank (4) is also connected to the clean water storage tank (41) and the wastewater treatment device (6); The solvent removal vessel (5) is also connected in sequence to the first condenser (51) and the first vacuum unit (52), and the first condenser (51) is also connected to the solvent recovery tank (53).
2. The apparatus for the acylation synthesis of oxazolidinyl acetonitrile according to claim 1, characterized in that, The first reactor (1) is also connected in sequence to the second condenser (13) and the second vacuum unit (14); The second condenser (13) is connected to the thionyl chloride recovery tank (15).
3. The apparatus for the acylation synthesis of oxazolidinyl acetonitrile according to claim 2, characterized in that, The first vacuum unit (52) and the second vacuum unit (14) are both connected to the exhaust gas treatment device (16).
4. The apparatus for the acylation synthesis of oxazolidinone according to claim 2, characterized in that, The desolventizing vessel (5) is also connected to the crystallization vessel (7), the centrifuge (71), and the pure product storage tank (72); The centrifuge (71) is also connected to the mother liquor storage tank (73), which is also connected to the crystallization vessel (7).
5. The apparatus for the acylation synthesis of oxazolidinone according to claim 1, characterized in that, The wastewater treatment device (6) includes a filter (61), a reverse osmosis device (62), a multi-effect evaporator (63), a thickener (64), a crystallization tank (65), a filter press (651), and a salt storage tank (66) connected in series. The filter press (651) is also connected to a filtrate storage tank (67), which is also connected to a thickener (64).
6. The apparatus for the acylation synthesis of oxazolidinone according to any one of claims 1-5, characterized in that, The upper part of the second reaction vessel (2) is provided with a drip pipe (200), which is connected to the peristaltic pump (10); The drip tube (200) has a ring structure and is fixed inside the upper head of the second reactor (2) by a connecting beam (201); The lower surface of the drip tube (200) is provided with drip heads (202) at equal intervals.
7. The apparatus for the acylation synthesis of oxazolidinone according to claim 3, characterized in that, The exhaust gas treatment device (16) is an incinerator or an activated carbon adsorption tower.