CN114534644B - Device and method for preparing 2-formamide cyclohexanone by catalyzing spiro hydrolysis with solid acid - Google Patents
Device and method for preparing 2-formamide cyclohexanone by catalyzing spiro hydrolysis with solid acid Download PDFInfo
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- CN114534644B CN114534644B CN202210137504.2A CN202210137504A CN114534644B CN 114534644 B CN114534644 B CN 114534644B CN 202210137504 A CN202210137504 A CN 202210137504A CN 114534644 B CN114534644 B CN 114534644B
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/08—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with moving particles
- B01J8/10—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with moving particles moved by stirrers or by rotary drums or rotary receptacles or endless belts
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The invention discloses a device and a method for preparing 2-formamide cyclohexanone by solid acid catalytic spiro hydrolysis, and relates to the technical field of 2-formamide cyclohexanone preparation, wherein the device is a vertical ball-milling reaction device; the device comprises a stirring paddle, a ball milling medium and a kettle type cylinder body with a jacket, wherein a raw material feeding pipe, a water inlet pipe, a vent pipe, a riser pipe and a temperature sensor are arranged at the top of the kettle type cylinder body with the jacket; a product discharge hole is formed in the bottom of the kettle type cylinder with the jacket; the vent pipe extends into the kettle bottom in the kettle type cylinder body with the jacket; the ball milling medium is filled in the kettle type cylinder with the clamping sleeve; the stirring paddle is arranged at the top of the kettle type cylinder body with the jacket, and the head of the stirring paddle is arranged in the ball milling medium. The method adopts a solid acid catalyst to catalyze the spiro hydrolysis, and the 2-formamide cyclohexanone is obtained after the hydrolysate is evaporated, concentrated, cooled, crystallized and subjected to solid-liquid separation.
Description
Technical Field
The invention relates to the technical field of preparation of 2-formamide cyclohexanone, and particularly relates to a device and a method for preparing 2-formamide cyclohexanone by catalyzing spiro hydrolysis with solid acid.
Background
The 2-formamide cyclohexanone is an important drug intermediate and is commonly used for preparing the diabetes drug gliclazide. Can be synthesized by a cyclohexanone route through two steps, wherein the first step is condensation of cyclohexanone and urea to obtain a spiro ring, and the second step is acid-catalyzed hydrolysis of the spiro ring to obtain 2-formamide cyclohexanone. In the prior art, the hydrolysis of the spiro ring is carried out in a stirring kettle by using sulfuric acid as a catalyst, controlling the pH of a hydrolysis solution within the range of 1.4-2.0 and the hydrolysis temperature at about 100 ℃. The method has two main problems: firstly, sulfuric acid is protonic acid and has strong ability of catalyzing spiro hydrolysis, but sulfuric acid has strong corrosion effect, particularly at high temperature, and a large amount of waste sulfuric acid solution can be generated after the reaction is finished, thereby bringing great environmental and three-waste treatment pressure. Secondly, although the mechanical stirring is simple, the effect of enhancing the mixing is poor because the mechanical stirring only macroscopically mixes the liquid and does not have the shearing and thinning effects on the materials. Particularly, the spiro is solid powder, hydrolysis of the spiro is solid-liquid reaction, and large mass transfer resistance exists between solid and liquid phases, so that the hydrolysis rate is slow, and the hydrolysis needs long time; the low pH, the high hydrolysis temperature and the long hydrolysis time are easy to cause the deep hydrolysis of the spiro ring, the side reaction is increased, and the selectivity of the 2-formamide cyclohexanone is reduced.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a device and a method for preparing 2-formamide cyclohexanone by solid acid catalytic spiro hydrolysis.
The invention aims to protect a device for preparing 2-formamide cyclohexanone by solid acid catalysis spiro hydrolysis. The device is a vertical ball milling reaction device; the device comprises a stirring paddle, a ball milling medium and a kettle type cylinder body with a jacket, wherein a raw material feeding pipe, a water inlet pipe, a vent pipe, a riser pipe and a temperature sensor are arranged at the top of the kettle type cylinder body with the jacket; a product discharge port is formed in the bottom of the kettle type cylinder body with the jacket; the vent pipe extends into the kettle bottom in the kettle type cylinder body with the jacket; the ball milling medium is filled in the kettle type cylinder body with the clamping sleeve; the stirring paddle is arranged at the top of the kettle type cylinder body with the jacket, and the head of the stirring paddle is arranged in a ball milling medium;
preferably, the bottom end of the vent pipe close to the kettle is arc-shaped, and the bottom end of the vent pipe close to the kettle is provided with a plurality of vent holes with the diameter of 2 mm.
Preferably, the temperature sensor extends into the kettle type cylinder with the clamping sleeve, and the distance between the temperature sensor and the kettle bottom is 80 mm.
Preferably, the head of the stirring paddle is spiral.
Preferably, the inner diameter of the kettle type cylinder body with the clamping sleeve is 120mm, and the height of the kettle type cylinder body is 150mm.
The invention also aims to protect a method for preparing 2-formamide cyclohexanone by solid acid catalysis spiro hydrolysis, which adopts the device and comprises the following steps:
s1, adding a ball milling medium, spiral ring powder and a solid acid catalyst from a raw material feeding pipe, adding water from a water inlet pipe, and connecting a stirring paddle with a variable speed motor for stirring;
s2, blowing nitrogen through a vent pipe;
s3, introducing heating steam into a jacket of the kettle type cylinder with the jacket to perform hydrolysis reaction, wherein the steam discharged from the riser in the reaction process enters a condenser, condensate flows out of the bottom of the condenser and enters a settling tank to be settled and layered, cyclohexanone on the upper layer is recovered, condensate on the lower layer is discharged as wastewater, and non-condensable gas is discharged from the top of the condenser and then enters an ammonia gas absorption device;
and S4, after the hydrolysis reaction is finished, discharging a product from a product discharge hole, and performing evaporation concentration, cooling crystallization, centrifugation and filtration separation on the product to obtain the 2-formamide cyclohexanone.
Preferably, in step S1, the ball milling medium is zirconium beads with a particle size of 3-5mm, and the amount is 100-1500g.
Preferably, in step S1, the solid acid catalyst comprises one or more of acid clay, strongly acidic ion exchange resin, and sulfonated carbon; the weight part ratio of the spiro powder to the solid acid catalyst to the water is 1.1-0.3; the stirring speed is 20-200rpm.
Preferably, in step S2, the flow rate of the nitrogen is 0.1-1L/min.
Preferably, in step S3, the temperature of the hydrolysis reaction is 90-100 ℃, and the time of the hydrolysis reaction is 0.5-5h.
The invention has the beneficial effects that:
(1) The method provided by the invention has the advantages of high hydrolysis rate and high product yield, the solid acid is adopted to replace sulfuric acid as the catalyst, the corrosion of the acid catalyst to equipment can be reduced, meanwhile, the catalyst can be recovered, the generation of acidic wastewater is reduced, and the production process is clean and environment-friendly.
(2) According to the device provided by the invention, the ball milling medium is added into the mechanical stirring kettle, and the stirring paddle drives the ball milling medium to rotate and collide in the reaction kettle, so that the turbulence of reaction materials is increased, and the solid spiro powder and the solid acid catalyst are continuously impacted and milled by the ball milling medium, so that the liquid layers on the spiro powder and the surface of the solid catalyst are continuously updated, and the mixing and mass transfer among the solid catalyst, the reaction materials, the spiro powder and the hydrolysate are strengthened, and the mechanical activation effect is realized on the reaction.
Drawings
In order to more clearly illustrate the detailed description of the invention or the technical solutions in the prior art, the drawings that are needed in the detailed description of the invention or the prior art will be briefly described below. Throughout the drawings, like elements or portions are generally identified by like reference numerals. In the drawings, elements or portions are not necessarily drawn to scale.
FIG. 1 is a schematic flow diagram of a process for preparing 2-carboxamide cyclohexanone by solid acid catalyzed spiro hydrolysis provided by the present invention;
FIG. 2 is a device for preparing 2-formamide cyclohexanone by solid acid catalytic spiro hydrolysis provided by the invention.
In FIG. 1, 1-a jacketed kettle-type cylinder; 2-ball milling medium; 3-stirring the slurry; 101-raw material feeding pipe, 102-water inlet pipe, 103-vent pipe, 104-riser pipe, 105-temperature sensor, 106-product discharging port, 107-jacket.
Detailed Description
Embodiments of the present invention will be described in detail below with reference to the accompanying drawings. The following examples are only for illustrating the technical solutions of the present invention more clearly, and therefore are only examples, and the protection scope of the present invention is not limited thereby.
It is to be noted that, unless otherwise specified, technical or scientific terms used herein shall have the ordinary meaning as understood by those skilled in the art to which the invention pertains.
Example 1
The embodiment provides a device for preparing 2-formamide cyclohexanone by solid acid catalytic spiro hydrolysis, which is a vertical ball milling reaction device; the device comprises a kettle type cylinder body 1 with a jacket, a ball milling medium 2 and a stirring paddle 3, wherein a raw material feeding pipe 101, a water inlet pipe 102, a vent pipe 103, a riser 104 and a temperature sensor 105 are arranged at the top of the kettle type cylinder body with the jacket; a product discharge hole 106 is formed in the bottom of the kettle type cylinder 1 with the clamping sleeve; the breather pipe 103 extends into the kettle bottom in the kettle type cylinder body 1 with the clamping sleeve; the ball milling medium 2 is filled in the kettle type cylinder 1 with the jacket; the stirring paddle 3 is arranged at the top of the kettle type cylinder 1 with the clamping sleeve, and the head of the stirring paddle 3 is arranged in the ball milling medium 2;
the bottom end of the vent pipe 103 close to the kettle is arc-shaped, and a plurality of vent holes with the diameter of 2mm are arranged at the bottom end of the vent pipe 103 close to the kettle.
The temperature sensor 105 extends into the kettle type cylinder 1 with the clamping sleeve, and the distance between the temperature sensor and the kettle bottom is 80 mm.
The head of the stirring paddle 3 is spiral.
The inner diameter of the kettle type cylinder 1 with the clamping sleeve is 120mm, and the height is 150mm.
The embodiment also provides a method for preparing 2-formamide cyclohexanone by solid acid catalysis spiro hydrolysis, which adopts the device and comprises the following steps:
s1, adding a ball milling medium 2, spiral ring powder and a solid acid catalyst from a raw material feeding pipe, adding water from a water inlet pipe, and connecting a stirring paddle 3 with a variable speed motor for stirring;
s2, blowing nitrogen through a vent pipe 103;
s3, introducing heating steam into a jacket 107 of the kettle-type cylinder 1 with the jacket to perform hydrolysis reaction, wherein the steam discharged from the riser 104 in the reaction process enters a condenser, condensate flows out of the bottom of the condenser and enters a settling tank to be settled and layered, cyclohexanone on the upper layer is recovered, condensate on the lower layer is discharged as wastewater, and non-condensable gas is discharged from the top of the condenser and then enters an ammonia gas absorption device;
and S4, after the hydrolysis reaction is finished, discharging a product from a product discharge hole 106, and performing evaporation concentration, cooling crystallization, centrifugation and filtration separation on the product to obtain the 2-formamide cyclohexanone.
In the step S1, the ball-milling medium is zirconium beads with the particle size of 3mm, and the using amount is 1500g.
In the step S1, the solid acid catalyst is strong acid ion exchange resin; 50g of spiro powder, 15g of solid acid catalyst and 150g of water.
The stirring speed was 150rpm.
In step S2, the flow rate of the nitrogen is 0.5L/min.
In the step S3, the temperature of the hydrolysis reaction is 98 ℃, and the time of the hydrolysis reaction is 2 hours.
38.4g of 2-formamide cyclohexanone is prepared in the example, and the product yield is 76.8%.
Example 2
The embodiment provides a device for preparing 2-formamide cyclohexanone by solid acid catalytic spiro hydrolysis, which is a vertical ball milling reaction device;
the device comprises a kettle type cylinder body 1 with a jacket, a ball milling medium 2 and a stirring paddle 3, wherein a raw material feeding pipe 101, a water inlet pipe 102, a vent pipe 103, a riser 104 and a temperature sensor 105 are arranged at the top of the kettle type cylinder body with the jacket; a product discharge hole 106 is formed in the bottom of the kettle type cylinder 1 with the clamping sleeve; the vent pipe 103 extends into the kettle bottom in the kettle type cylinder body 1 with the clamping sleeve; the ball milling medium 2 is filled in the kettle type cylinder 1 with the jacket; the stirring paddle 3 is arranged at the top of the kettle type cylinder 1 with the clamping sleeve, and the head of the stirring paddle 3 is arranged in the ball milling medium 2;
the bottom end of the vent pipe 103 close to the kettle is arc-shaped, and a plurality of vent holes with the diameter of 2mm are arranged at the bottom end of the vent pipe 103 close to the kettle.
The temperature sensor 105 extends into the kettle type cylinder 1 with the clamping sleeve, and the distance between the temperature sensor and the kettle bottom is 80 mm.
The head of the stirring paddle 3 is spiral.
The inner diameter of the kettle type cylinder 1 with the clamping sleeve is 120mm, and the height is 150mm.
The embodiment also provides a method for preparing 2-formamide cyclohexanone by solid acid catalysis spiro hydrolysis, which adopts the device and comprises the following steps:
s1, adding a ball milling medium 2, spiral ring powder and a solid acid catalyst from a raw material feeding pipe, adding water from a water inlet pipe, and connecting a stirring paddle 3 with a variable speed motor for stirring;
s2, blowing nitrogen through a vent pipe 103;
s3, introducing heating steam into a jacket 107 of the kettle-type cylinder 1 with the jacket to perform hydrolysis reaction, wherein the steam discharged from the riser 104 in the reaction process enters a condenser, condensate flows out of the bottom of the condenser and enters a settling tank to be settled and layered, cyclohexanone on the upper layer is recovered, condensate on the lower layer is discharged as wastewater, and non-condensable gas is discharged from the top of the condenser and then enters an ammonia gas absorption device;
and S4, after the hydrolysis reaction is finished, discharging a product from a product discharge hole 106, and performing evaporation concentration, cooling crystallization, centrifugation and filtration separation on the product to obtain the 2-formamide cyclohexanone.
In the step S1, the ball-milling medium is zirconium beads with the particle size of 5mm, and the dosage is 500g.
In the step S1, the solid acid catalyst is sulfonated carbon; 50g of spiro powder, 5g of solid acid catalyst and 150g of water.
The stirring speed was 150rpm.
In step S2, the flow rate of the nitrogen is 0.5L/min.
In the step S3, the temperature of the hydrolysis reaction is 98 ℃, and the time of the hydrolysis reaction is 0.5h.
This example produced 11.2g of 2-carboxamide cyclohexanone with a product yield of 22.4%.
Example 3
The embodiment provides a device for preparing 2-formamide cyclohexanone by solid acid catalytic spiro hydrolysis, which is a vertical ball milling reaction device;
the device comprises a kettle type cylinder body 1 with a jacket, a ball milling medium 2 and a stirring paddle 3, wherein a raw material feeding pipe 101, a water inlet pipe 102, a vent pipe 103, a riser 104 and a temperature sensor 105 are arranged at the top of the kettle type cylinder body with the jacket; a product discharge hole 106 is formed in the bottom of the kettle type cylinder 1 with the clamping sleeve; the vent pipe 103 extends into the kettle bottom in the kettle type cylinder body 1 with the clamping sleeve; the ball milling medium 2 is filled in the kettle type cylinder 1 with the jacket; the stirring paddle 3 is arranged at the top of the kettle type cylinder body 1 with the clamping sleeve, and the head of the stirring paddle 3 is arranged in the ball milling medium 2;
the bottom end of the breather pipe 103 close to the kettle is arc-shaped, and a plurality of vent holes with the diameter of 2mm are arranged at the bottom end of the breather pipe 103 close to the kettle.
The temperature sensor 105 extends into the kettle type cylinder 1 with the clamping sleeve, and the distance between the temperature sensor and the kettle bottom is 80 mm.
The head of the stirring paddle 3 is spiral.
The inner diameter of the kettle type cylinder 1 with the clamping sleeve is 120mm, and the height of the kettle type cylinder is 150mm.
The embodiment also provides a method for preparing 2-formamide cyclohexanone by solid acid catalysis spiro hydrolysis, which adopts the device and comprises the following steps:
s1, adding a ball milling medium 2, spiral ring powder and a solid acid catalyst into a raw material feeding pipe, adding water into the raw material feeding pipe, and connecting a stirring paddle 3 with a variable speed motor for stirring;
s2, blowing nitrogen through a vent pipe 103;
s3, introducing heating steam into a jacket 107 of the kettle-type cylinder 1 with the jacket to perform hydrolysis reaction, wherein the steam discharged from the riser 104 in the reaction process enters a condenser, condensate flows out of the bottom of the condenser and enters a settling tank to be settled and layered, cyclohexanone on the upper layer is recovered, condensate on the lower layer is discharged as wastewater, and non-condensable gas is discharged from the top of the condenser and then enters an ammonia gas absorption device;
and S4, after the hydrolysis reaction is finished, discharging a product from a product discharge hole 106, and performing evaporation concentration, cooling crystallization, centrifugation and filtration separation on the product to obtain the 2-formamide cyclohexanone.
In the step S1, the ball-milling medium is zirconium beads with the particle size of 3mm, and the using amount is 1500g.
In the step S1, the solid acid catalyst is acid clay; 50g of spiro powder, 15g of solid acid catalyst and 150g of water.
The stirring speed was 150rpm.
In step S2, the flow rate of the nitrogen is 1L/min.
In the step S3, the temperature of the hydrolysis reaction is 98 ℃, and the time of the hydrolysis reaction is 5 hours.
This example produced 41.2g of 2-carboxamide cyclohexanone with a product yield of 82.4%.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; such modifications and substitutions do not depart from the spirit and scope of the present invention, and they should be construed as being included in the following claims and description.
Claims (9)
1. A method for preparing 2-formamide cyclohexanone by solid acid catalysis spiro hydrolysis is characterized in that: the method adopts a device for preparing the 2-formamide cyclohexanone by catalyzing the spiro hydrolysis with solid acid, and the device is a vertical ball-milling reaction device; the device comprises a stirring paddle, a ball milling medium and a kettle type cylinder body with a jacket, wherein a raw material feeding pipe, a water inlet pipe, a vent pipe, a riser pipe and a temperature sensor are arranged at the top of the kettle type cylinder body with the jacket; a product discharge hole is formed in the bottom of the kettle type cylinder with the jacket; the vent pipe extends into the kettle bottom in the kettle type cylinder body with the jacket; the ball milling medium is filled in the kettle type cylinder with the clamping sleeve; the stirring paddle is arranged at the top of the kettle type cylinder body with the jacket, and the head of the stirring paddle is arranged in a ball milling medium; the method comprises the following steps: s1, adding a ball milling medium, spiral ring powder and a solid acid catalyst into a raw material feeding pipe, adding water into the raw material feeding pipe, and connecting a stirring paddle with a variable speed motor for stirring; s2, blowing nitrogen through a vent pipe; s3, introducing heating steam into a jacket of the kettle type cylinder with the jacket to perform hydrolysis reaction, wherein the steam discharged from the riser in the reaction process enters a condenser, condensate flows out of the bottom of the condenser and enters a settling tank to be settled and layered, cyclohexanone on the upper layer is recovered, condensate on the lower layer is discharged as wastewater, and non-condensable gas is discharged from the top of the condenser and then enters an ammonia gas absorption device; and S4, after the hydrolysis reaction is finished, discharging a product from a product discharge hole, and performing evaporation concentration, cooling crystallization, centrifugation and filtration separation on the product to obtain the 2-formamide cyclohexanone.
2. The process for the preparation of 2-carboxamide cyclohexanone by solid acid catalyzed spiro hydrolysis according to claim 1, characterized in that: the bottom end of the vent pipe close to the kettle is arc-shaped, and a plurality of vent holes with the diameter of 2mm are arranged at the bottom end of the vent pipe close to the kettle.
3. The process for the preparation of 2-carboxamide cyclohexanone by solid acid catalyzed spiro hydrolysis according to claim 1, characterized in that: the temperature sensor extends into the kettle type cylinder with the clamping sleeve, and the distance between the temperature sensor and the kettle bottom is 80 mm.
4. The process for the preparation of 2-carboxamide cyclohexanone by solid acid catalyzed spiro hydrolysis according to claim 1, characterized in that: the head of the stirring paddle is spiral.
5. The process for the preparation of 2-carboxamide cyclohexanone by solid acid catalyzed spiro hydrolysis according to claim 1, characterized in that: the inner diameter of the kettle type cylinder body with the jacket is 120mm, and the height of the kettle type cylinder body is 150mm.
6. The process for the preparation of 2-carboxamide cyclohexanone by solid acid catalyzed spiro hydrolysis according to claim 1, characterized in that: in the step S1, the ball-milling medium is zirconium beads with the particle size of 3-5mm, and the using amount is 100-1500g.
7. The process for the preparation of 2-carboxamide cyclohexanone by solid acid catalyzed spiro hydrolysis according to claim 1, characterized in that: in the step S1, the solid acid catalyst comprises one or more of acid clay, strong acid ion exchange resin and sulfonated carbon; the weight part ratio of the spiro powder to the solid acid catalyst to the water is 1.1-0.3; the stirring speed is 20-200rpm.
8. The process for the preparation of 2-carboxamide cyclohexanone by solid acid catalyzed spiro hydrolysis according to claim 1, characterized in that: in the step S2, the flow rate of the nitrogen is 0.1-1L/min.
9. The process for the preparation of 2-carboxamide cyclohexanone by solid acid catalyzed spiro hydrolysis according to claim 1, characterized in that: in the step S3, the temperature of the hydrolysis reaction is 90-100 ℃, and the time of the hydrolysis reaction is 0.5-5h.
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| CN202210137504.2A CN114534644B (en) | 2022-02-15 | 2022-02-15 | Device and method for preparing 2-formamide cyclohexanone by catalyzing spiro hydrolysis with solid acid |
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| CN110404635A (en) * | 2019-08-05 | 2019-11-05 | 东北大学 | A kind of fluidization vertical stirring mill suitable for dry type grinding |
| CN112013402A (en) * | 2020-08-28 | 2020-12-01 | 飞潮（无锡）过滤技术有限公司 | Ball-milling type pyrolysis activation furnace |
| CN213761778U (en) * | 2020-07-29 | 2021-07-23 | 广东百试特生物技术研究院有限公司 | Medicine nanocrystal preparation system |
| CN214488253U (en) * | 2020-12-29 | 2021-10-26 | 洛阳天瑞环保科技有限公司 | High-efficient defluorination dechlorination denitrification device of aluminium ash |
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2022
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA667356A (en) * | 1963-07-23 | F. Mckay Arthur | Aminoacid amides | |
| DD112987A1 (en) * | 1974-07-10 | 1975-05-12 | ||
| US4169952A (en) * | 1977-03-14 | 1979-10-02 | E. I. Du Pont De Nemours And Company | Process for the preparation of cyclohexanone-2-carboxamide |
| CN103159642A (en) * | 2011-12-17 | 2013-06-19 | 山东方明药业集团股份有限公司 | Preparation method of gliclazide intermediate cyclohexanone-2-methanmide |
| CN102935350A (en) * | 2012-11-14 | 2013-02-20 | 广西大学 | Vertical modified stir ball-milling reactor for reinforcing polysaccharide polymers |
| CN103664682A (en) * | 2013-11-22 | 2014-03-26 | 中国矿业大学 | Synthetic method for 2-formamide cyclohexanone |
| CN110404635A (en) * | 2019-08-05 | 2019-11-05 | 东北大学 | A kind of fluidization vertical stirring mill suitable for dry type grinding |
| CN213761778U (en) * | 2020-07-29 | 2021-07-23 | 广东百试特生物技术研究院有限公司 | Medicine nanocrystal preparation system |
| CN112013402A (en) * | 2020-08-28 | 2020-12-01 | 飞潮（无锡）过滤技术有限公司 | Ball-milling type pyrolysis activation furnace |
| CN214488253U (en) * | 2020-12-29 | 2021-10-26 | 洛阳天瑞环保科技有限公司 | High-efficient defluorination dechlorination denitrification device of aluminium ash |
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