CN111662214A - Method for preparing cyclohexyl isocyanate by using solid phosgene - Google Patents
Method for preparing cyclohexyl isocyanate by using solid phosgene Download PDFInfo
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- CN111662214A CN111662214A CN202010587674.1A CN202010587674A CN111662214A CN 111662214 A CN111662214 A CN 111662214A CN 202010587674 A CN202010587674 A CN 202010587674A CN 111662214 A CN111662214 A CN 111662214A
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- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
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Abstract
The invention provides a method for preparing cyclohexyl isocyanate by using solid phosgene, which comprises the following steps: s1, dissolving solid phosgene in a solvent; s2, slowly adding the solid phosgene solution into cyclohexylamine hydrochloride, heating, and carrying out phosgenation reaction to obtain a cyclohexyl isocyanate crude product; s3, separating and purifying to obtain the cyclohexyl isocyanate. According to the method provided by the invention, the solid phosgene and the cyclohexylamine hydrochloride react to prepare the cyclohexyl isocyanate, so that the yield of the cyclohexyl isocyanate is ensured, and the solid phosgene has stable chemical properties and no obvious toxicity, and has the advantages of improving the safety and reducing the safe production cost.
Description
Technical Field
The invention relates to the technical field of organic chemical synthesis, in particular to a method for preparing cyclohexyl isocyanate by using solid phosgene
Background
Cyclohexyl isocyanate is an organic raw material and is used as an intermediate for synthesizing medicines or pesticides, the pesticides are used for producing herbicides such as hexazinone and the like, and the medicines are used for producing western medicines and hexythiazox raw medicines.
The existing cyclohexyl isocyanate is prepared by synthesizing phosgene and cyclohexylamine hydrochloride. The raw material phosgene is highly toxic, non-combustible, high in chemical reaction activity and strongly corrosive after meeting water. Phosgene is obtained from the synthesis of carbon monoxide and chlorine. Phosgene is colorless gas at normal temperature and has rotten grass smell, phosgene is yellow green liquid at low temperature, chemical properties are unstable, and phosgene is quickly hydrolyzed in water to generate hydrogen chloride, so that the safety production cost in the manufacturing process of cyclohexyl isocyanate is increased.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides the method for preparing the cyclohexyl isocyanate by the solid phosgene, the cyclohexyl isocyanate is prepared by the reaction of the solid phosgene and the cyclohexylamine hydrochloride, the yield of the cyclohexyl isocyanate is ensured, and the production safety is improved.
In order to achieve the above object, the present invention is achieved by the following technical solutions.
The invention provides a method for preparing cyclohexyl isocyanate by using solid phosgene, which comprises the following steps:
s1, dissolving solid phosgene in a solvent;
s2, slowly adding the solid phosgene solution into cyclohexylamine hydrochloride, heating, and carrying out phosgenation reaction to obtain a cyclohexyl isocyanate crude product;
s3, separating and purifying to obtain the cyclohexyl isocyanate.
Preferably, in step S1, the solvent includes toluene.
Preferably, the mass ratio of the solid phosgene to the toluene is (0.35-1.43): 1; the dissolving temperature is-5 ℃ to 36 ℃.
Preferably, the mass ratio of the solid phosgene to the toluene is 1.15: 1; the dissolution temperature was 30 ℃.
Preferably, in step S2, the solid phosgene solution is slowly added into the cyclohexylamine hydrochloride to form a phosgenation reaction system with a micro negative pressure of-85 mm to-75 mm water column.
Preferably, in step S2, the reaction mixture is heated to a phosgenation reaction temperature of 100 to 110 ℃.
Preferably, step S2 further includes a salt-forming reaction, in which cyclohexylamine is subjected to the salt-forming reaction to generate cyclohexylamine hydrochloride.
Preferably, in step S2, the solid phosgene and cyclohexylamine hydrochloride are subjected to a phosgenation reaction without a catalyst.
Preferably, step S3 includes:
s301, introducing dry nitrogen into the cyclohexyl isocyanate crude product prepared in the step S2 for deacidification;
s302, rectifying the deacidified cyclohexyl isocyanate mixture in the step S301 to obtain cyclohexyl isocyanate.
Preferably, in step S301, the deacidification temperature is 100 to 110 ℃; deacidifying until the acidity of the solution is less than or equal to 0.1 percent, and stopping introducing nitrogen.
Compared with the prior art, the invention has the beneficial effects that:
according to the method for preparing cyclohexyl isocyanate by using the solid phosgene, the solid phosgene is used for replacing phosgene which is one of raw materials in the original synthesis method, the cyclohexyl isocyanate is prepared by reacting the solid phosgene with cyclohexylamine hydrochloride, the yield of the cyclohexyl isocyanate is ensured, the solid phosgene has stable chemical properties and no obvious toxicity, has the advantages of improving safety and reducing safe production cost, and has higher competitive advantages at present when people continuously enhance environmental protection consciousness and safe production requirements, emphasize economic sustainable development and propose a circular economy concept. In a preferred scheme, the solid phosgene and the cyclohexylamine hydrochloric acid are subjected to a phosgenation reaction under the catalyst-free condition, so that the yield of cyclohexyl isocyanate is ensured, and the increase of waste liquid in the subsequent rectification process and the increase of purification cost caused by the use of a catalyst are avoided.
The foregoing description is only an overview of the technical solutions of the present invention, and some embodiments are described in detail below in order to make the technical solutions of the present invention more clearly understood and to implement the technical solutions according to the content of the description. Specific embodiments of the present invention are given in detail by the following examples.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this application, illustrate embodiment(s) of the invention and together with the description serve to explain the invention without limiting the invention. In the drawings:
FIG. 1 is a flow chart of the preparation of isocyanate by using solid phosgene in one embodiment of the present invention;
FIG. 2 is a diagram showing the phosgenation reaction equation of the phosgene solid and cyclohexylamine hydrochloride in the present invention.
Detailed Description
In order that the invention described herein may be more fully understood, the following examples are set forth. It should be understood that these examples are for illustrative purposes only and are not to be construed as limiting the invention in any way.
The invention provides a method for preparing cyclohexyl isocyanate by using solid phosgene, which comprises the following steps as shown in figure 1:
s1, dissolving solid phosgene in a solvent to obtain a solid phosgene solution;
s2, slowly adding the solid phosgene solution into cyclohexylamine hydrochloride, heating, and carrying out phosgenation reaction on the solid phosgene and the cyclohexylamine hydrochloride, wherein the reaction formula is shown in figure 2, so as to obtain a crude product of cyclohexyl isocyanate; solid phosgene is used as a reaction raw material to replace phosgene in the traditional synthetic reaction, so that the increase of safe production cost caused by factors such as unstable chemical property, high toxicity and the like of phosgene is avoided;
s3, separating and purifying the crude product of the cyclohexyl isocyanate to obtain the cyclohexyl isocyanate.
In one embodiment, in step S1, the solvent includes toluene. The boiling point of the toluene is 110.6 ℃, the boiling point of the cyclohexyl isocyanate is 168-170 ℃, the difference between the boiling point of the toluene and the boiling point of the cyclohexyl isocyanate is large when the toluene dissolves the solid phosgene, and the separation and purification of the cyclohexyl isocyanate mixture obtained by the reaction in the subsequent rectification process are facilitated. Specifically, toluene is added into the solid phosgene, the adding speed is controlled, the solid phosgene is not easy to be added too fast, and the toluene solution is prevented from splashing due to the fact that the solid phosgene is dissolved too fast; and after the toluene is added, starting stirring until the solid phosgene is completely dissolved, and stopping stirring.
Further, the mass ratio of the solid phosgene to the toluene is (0.35-1.43): 1; the dissolving temperature is-5 ℃ to 36 ℃ so that the toluene can fully dissolve the solid phosgene. Further, the mass ratio of the solid phosgene to the toluene is 1.15: 1; the dissolution temperature was 30 ℃.
In one embodiment, in step S2, a solid phosgene solution is slowly added to cyclohexylamine hydrochloride to form a phosgenation reaction system with a micro-negative pressure of-85 mm to-75 mm water column. And controlling the rate of adding the solid phosgene solution into the cyclohexylamine hydrochloride so that the micro negative pressure of the phosgene reduction reaction system is-85 mm to-75 mm of water column. If the rate of adding the solid phosgene solution into the cyclohexylamine hydrochloride is too high, the solid phosgene is decomposed too fast, and decomposed products are discharged into a tail gas treatment system, so that the utilization rate of the solid phosgene is low, and the cost is increased; in addition, the solid phosgene is decomposed too fast, so that the pressure in a phosgenation reaction container is too high, and the safety production risk is increased; further, the exhaust emission is too fast, and the exhaust treatment system cannot treat excessive exhaust in time. Thus, a phosgene solution was slowly added to cyclohexylamine hydrochloride. Furthermore, the micro negative pressure in the phosgenation reaction system is-80 mm water column. When the micro negative pressure of the reaction system is less than minus 80mm of water column, increasing the adding rate of the solid phosgene; when the micro negative pressure of the reaction system is more than-80 mm of water column, the adding speed of the solid phosgene is reduced.
Further, in step S2, the mixture is heated to a phosgenation reaction temperature of 100 to 110 ℃, so as to increase the rate of the phosgenation reaction of the phosgene and cyclohexylamine hydrochloride and the product yield.
Further, in step S2, the mass ratio of the solid phosgene to the cyclohexylamine hydrochloride is 1: 3, the raw materials are reasonably utilized, and the waste of the raw materials is avoided.
Further, step S2 further includes a salt-forming reaction, in which cyclohexylamine is subjected to a salt-forming reaction to generate cyclohexylamine hydrochloride. Forming hydrochloric acid gas from the hydrochloric acid solution through an acid forming system, reacting the formed hydrochloric acid gas with cyclohexylamine in a toluene solvent to prepare cyclohexylamine hydrochloride, and removing water.
Further, in step S2, the solid phosgene and cyclohexylamine hydrochloride are subjected to a phosgenation reaction without a catalyst. No catalyst is used, the reaction speed of the solid phosgene and the cyclohexylamine hydrochloride cannot be obviously influenced, and the increase of waste liquid in the subsequent rectification process and the increase of the production cost cannot be caused.
In one embodiment, step S3 includes:
s301, introducing dry nitrogen into the cyclohexyl isocyanate crude product prepared in the step S2 for deacidification, and removing a phosgene reaction product HCl in the step S2; further, in step S301, the deacidification temperature is 100-110 ℃; deacidifying until the acidity of the solution is less than or equal to 0.1%, and stopping introducing nitrogen;
s302, rectifying the deacidified cyclohexyl isocyanate mixture in the step S301, and removing the solvent in the cyclohexyl isocyanate mixture to obtain the cyclohexyl isocyanate.
In order that the invention herein may be more fully understood, the following specific examples are set forth.
Example 1
The invention provides a method for preparing cyclohexyl isocyanate by using solid phosgene, which comprises the following steps:
s1, adding 151g of solid phosgene into a four-neck flask, adding toluene into the solid phosgene, and dissolving the solid phosgene into a toluene solvent; wherein the mass ratio of the solid phosgene to the toluene is 1.15: 1; the system temperature for dissolving the solid phosgene is 30 ℃;
s2, slowly adding a toluene solution containing 151g of solid phosgene into a 2000ml four-neck flask filled with cyclohexylamine hydrochloride at the rate of 3ml/min, heating to 100 ℃, and carrying out phosgenation reaction on the solid phosgene and the cyclohexylamine hydrochloride until the solution in the four-neck flask is clear to obtain a cyclohexyl isocyanate crude product; wherein, the adding speed of the toluene solution of the solid phosgene is controlled to ensure that the micro negative pressure of a phosgenation reaction system is 80mm water column below zero, and when the micro negative pressure of the reaction system is less than 80mm water column below zero, the adding speed of the toluene solution of the solid phosgene is increased; when the micro negative pressure of the reaction system is more than-80 mm of water column, reducing the adding rate of the toluene solution of the solid phosgene;
s3, separating and purifying the crude product of the cyclohexyl isocyanate in the step S2 to obtain the cyclohexyl isocyanate.
Further, step S3 includes:
s301, opening a nitrogen steel cylinder, introducing nitrogen into the 2000ml four-neck flask in the step S2 through a drying device, controlling the temperature to be about 100 ℃, starting deacidification until the acidity of the solution is less than or equal to 0.1%, and removing HCl;
s302, rectifying the deacidified cyclohexyl isocyanate mixture in the step S301; specifically, in step S301, zeolite is added into a 2000ml four-neck flask, and a cooling circulating liquid, a vacuum pump and a heating jacket are started until the solution is boiled. Continuously heating until the temperature at the top of the tower rises to be constant, totally refluxing for 10min, and collecting the solvent. And continuously heating until the low temperature of the tower is raised to be unchanged, stopping liquid extraction when the temperature of the top of the tower is raised, and performing total reflux for 10 min. The light fraction was collected slowly. When the temperature at the top of the column is raised to be kept constant, the rectification liquid is collected.
Further, the salt forming reaction of the cyclohexylamine to prepare the cyclohexylamine hydrochloride comprises the following steps:
acid-forming system: 200ml of hydrochloric acid solution is added into a 500ml four-neck flask, the cooling circulating liquid is started, stirring is started, and a heating jacket is started. When the temperature was 50 ℃, 200g of a phosphorus oxychloride solution in a dropping funnel was slowly dropped into the four-necked flask while maintaining the temperature at 50 ℃. Leading the generated hydrochloric acid gas into a salt forming system through a drying device;
salifying system: a2000 ml four-necked flask was charged with 150g of a cyclohexylamine solution and 600ml of toluene. And starting cooling circulating liquid and stirring. Introducing hydrochloric acid gas generated by an acid forming system, and keeping the temperature to be less than or equal to 65 ℃. When the pH value of the solution is 1-2, indicating that salt formation meets the standard;
carrying out water carrying: after salifying is finished, the water-carrying condensation tube is replaced, the temperature is raised, and the temperature is controlled to be about 110 ℃ until water in the system is removed.
Finally, the light components and the rectification liquid collected in step S302 are analyzed. Analyzing the light component, wherein the content of cyclohexyl isocyanate in the light component is 15.1%; the rectification liquid was analyzed, and the content of cyclohexyl isocyanate in the rectification liquid was 99.1%. The calculated yield of cyclohexyl isocyanate is: 94.7 percent. Wherein, the yield of the cyclohexyl isocyanate is calculated by the following formula: (rectification liquid cyclohexyl isocyanate quality multiplied by 100%)/cyclohexyl isocyanate theoretical quality; the theoretical mass of cyclohexyl isocyanate shows the mass of cyclohexyl isocyanate prepared by the raw materials all participating in the phosgenation reaction.
Example 2
S1, adding 151g of solid phosgene into a four-neck flask, adding toluene into the solid phosgene, and dissolving the solid phosgene into a toluene solvent; wherein the mass ratio of the solid phosgene to the toluene is 1.15: 1; the system temperature for dissolving the solid phosgene is 30 ℃;
s2, adding 4g of triethylamine catalyst into a 2000ml four-neck flask filled with cyclohexylamine hydrochloride, slowly adding a toluene solution containing 151g of solid phosgene into the cyclohexylamine hydrochloride at the rate of 3ml/min, heating to 100 ℃, and carrying out phosgenation reaction on the solid phosgene and the cyclohexylamine hydrochloride until the solution in the four-neck flask is clear to obtain a cyclohexyl isocyanate crude product; wherein, the adding speed of the toluene solution of the solid phosgene is controlled to ensure that the micro negative pressure of the phosgenation reaction system is 80mm water column below zero;
s3, separating and purifying the crude product of the cyclohexyl isocyanate in the step S2 to obtain the cyclohexyl isocyanate.
Further, step S3 includes:
s301, opening a nitrogen steel cylinder, introducing nitrogen into the 2000ml four-neck flask in the step S2 through a drying device, controlling the temperature to be about 100 ℃, starting deacidification until the acidity of the solution is less than or equal to 0.1%, and removing HC;
s302, rectifying the deacidified cyclohexyl isocyanate mixture in the step S301; specifically, in step S301, zeolite is added into a 2000ml four-neck flask, and a cooling circulating liquid, a vacuum pump and a heating jacket are started until the solution is boiled. Continuously heating until the temperature at the top of the tower rises to be constant, totally refluxing for 10min, and collecting the solvent. And continuously heating until the low temperature of the tower is raised to be unchanged, stopping liquid extraction when the temperature of the top of the tower is raised, and performing total reflux for 10 min. The light fraction was collected slowly. When the temperature at the top of the column is raised to be kept constant, the rectification liquid is collected.
Further, the salt forming reaction of the cyclohexylamine to prepare the cyclohexylamine hydrochloride comprises the following steps:
acid-forming system: 200ml of hydrochloric acid solution is added into a 500ml four-neck flask, the cooling circulating liquid is started, stirring is started, and a heating jacket is started. When the temperature was 50 ℃, 200g of a phosphorus oxychloride solution in a dropping funnel was slowly dropped into the four-necked flask while maintaining the temperature at 50 ℃. Leading the generated hydrochloric acid gas into a salt forming system through a drying device;
salifying system: a2000 ml four-necked flask was charged with 150g of a cyclohexylamine solution and 600ml of toluene. And starting cooling circulating liquid and stirring. Introducing hydrochloric acid gas generated by an acid forming system, and keeping the temperature to be less than or equal to 65 ℃. When the pH value of the solution is 1-2, indicating that salt formation meets the standard;
carrying out water carrying: after salifying is finished, the water-carrying condensation tube is replaced, the temperature is raised, the temperature is controlled to be about 110 ℃, and until moisture in the system is removed, the cyclohexylamine hydrochloride is obtained.
Finally, the light components and the rectification liquid collected in step S302 are analyzed. Analyzing the light component, wherein the content of cyclohexyl isocyanate in the light component is 15.3%; the rectification liquid was analyzed, and the content of cyclohexyl isocyanate in the rectification liquid was 98.8%. The calculated yield of cyclohexyl isocyanate is: 93.1 percent.
Comparative example 1
Acid-forming system: 200ml of hydrochloric acid solution is added into a 500ml four-neck flask, the cooling circulating liquid is started, stirring is started, and a heating jacket is started. When the temperature was 50 ℃, 200g of a phosphorus oxychloride solution in a dropping funnel was slowly dropped into the four-necked flask while maintaining the temperature at 50 ℃. Leading the generated hydrochloric acid gas into a salt forming system through a drying device;
salifying system: a2000 ml four-necked flask was charged with 150g of a cyclohexylamine solution and 600ml of toluene. And starting cooling circulating liquid and stirring. Introducing hydrochloric acid gas generated by an acid forming system, and keeping the temperature to be less than or equal to 65 ℃. When the pH value of the solution is 1-2, indicating that salt formation meets the standard;
carrying out water carrying: after salifying is finished, replacing a water-carrying condensation tube, starting heating, and controlling the temperature to be about 110 ℃ until water in the system is removed; obtaining cyclohexylamine hydrochloride;
photochemical catalysis: slowly adding 220g of diphosgene into a 2000ml four-neck flask filled with cyclohexylamine hydrochloride, heating to 100 ℃, and carrying out phosgenation reaction on diphosgene and cyclohexylamine hydrochloride until the solution in the four-neck flask is clear to obtain a cyclohexyl isocyanate crude product; wherein, the adding rate of the diphosgene is controlled to ensure that the micro negative pressure of the phosgenation reaction system is minus 80mm water column;
deacidifying: opening a nitrogen steel cylinder, introducing nitrogen into a 2000ml four-neck flask filled with a crude product of cyclohexyl isocyanate through a drying device, controlling the temperature to be about 100 ℃, starting deacidification until the acidity of the solution is less than or equal to 0.1%, and removing HCl;
and (3) rectification: rectifying the mixture of cyclohexyl isocyanate after deacidification in the deacidification step; specifically, zeolite was added to a 2000ml four-neck flask containing the deacidified cyclohexyl isocyanate mixture, and the cooling circulation, vacuum pump, and heating mantle were started until the solution was boiling. Continuously heating until the temperature at the top of the tower rises to be constant, totally refluxing for 10min, and collecting the solvent. And continuously heating until the low temperature of the tower is raised to be unchanged, stopping liquid extraction when the temperature of the top of the tower is raised, and performing total reflux for 10 min. The light fraction was collected slowly. When the temperature at the top of the column is raised to be kept constant, the rectification liquid is collected.
Finally, the light components and the rectification liquid collected in the rectification step are analyzed. Analyzing the light component, wherein the content of cyclohexyl isocyanate in the light component is 14.9%; the distillate was analyzed and the content of cyclohexyl isocyanate in the distillate was 98.1%, but the mass of the distillate in this example was less than that of the distillate obtained in example 2. The calculated yield of cyclohexyl isocyanate is: 87.7 percent. The yield of cyclohexyl isocyanate is low due to the fast decomposition of diphosgene in photochemical reaction.
The method for preparing cyclohexyl isocyanate by using the solid phosgene, provided by the invention, is prepared by carrying out phosgenation reaction on the solid phosgene and cyclohexylamine hydrochloride, ensures the yield of the cyclohexyl isocyanate, has the advantages of relatively stable chemical properties of the solid phosgene, no obvious toxicity, improved safety and reduced safe production cost, and has higher competitive advantages at present when people continuously strengthen the requirements on environmental protection consciousness and safe production and emphasize economic sustainable development and propose a circular economy concept.
While embodiments of the invention have been disclosed above, it is not limited to the applications listed in the description and the embodiments, which are fully applicable in all kinds of fields of adaptation of the invention, and further modifications can be easily implemented by those skilled in the art, so that the invention is not limited to the specific details and the examples shown herein, without departing from the general concept defined by the claims and the scope of equivalents.
Claims (10)
1. The method for preparing cyclohexyl isocyanate by using solid phosgene is characterized by comprising the following steps:
s1, dissolving solid phosgene in a solvent;
s2, slowly adding the solid phosgene solution into cyclohexylamine hydrochloride, heating, and carrying out phosgenation reaction to obtain a cyclohexyl isocyanate crude product;
s3, separating and purifying to obtain the cyclohexyl isocyanate.
2. The method for preparing cyclohexyl isocyanate with solid phosgene as claimed in claim 1, wherein in step S1, the solvent comprises toluene.
3. The method for preparing cyclohexyl isocyanate with solid phosgene, according to claim 2, is characterized in that the mass ratio of the solid phosgene to the toluene is (0.35-1.43): 1; the dissolving temperature is-5 ℃ to 36 ℃.
4. The method for preparing cyclohexyl isocyanate by using solid phosgene, which is characterized in that the mass ratio of the solid phosgene to the toluene is 1.15: 1; the dissolution temperature was 30 ℃.
5. The method for preparing cyclohexyl isocyanate with solid phosgene as claimed in claim 1, wherein in step S2, the solid phosgene solution is slowly added into cyclohexylamine hydrochloride to form a phosgenation reaction system with micro negative pressure of-85 mm to-75 mm water column.
6. The method for preparing cyclohexyl isocyanate with solid phosgene as claimed in claim 1, wherein in step S2, the heating is carried out to a phosgenation reaction temperature of 100 ℃ to 110 ℃.
7. The method for preparing cyclohexyl isocyanate with solid phosgene as claimed in claim 1, wherein step S2 further comprises a salt-forming reaction, wherein cyclohexylamine is subjected to the salt-forming reaction to generate cyclohexylamine hydrochloride.
8. The method for preparing cyclohexyl isocyanate with solid phosgene as claimed in claim 1, wherein in step S2, the solid phosgene and cyclohexylamine hydrochloride are subjected to phosgenation reaction without catalyst.
9. The method for preparing cyclohexyl isocyanate with solid phosgene as claimed in claim 1, wherein step S3 includes:
s301, introducing dry nitrogen into the cyclohexyl isocyanate crude product prepared in the step S2 for deacidification;
s302, rectifying the deacidified cyclohexyl isocyanate mixture in the step S301 to obtain cyclohexyl isocyanate.
10. The method for preparing cyclohexyl isocyanate with solid phosgene according to claim 8, wherein in step S301, the deacidification temperature is 100 ℃ to 110 ℃; deacidifying until the acidity of the solution is less than or equal to 0.1 percent, and stopping introducing nitrogen.
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| CN114014783A (en) * | 2021-11-18 | 2022-02-08 | 甘肃银光聚银化工有限公司 | Method for preparing 1, 5-diamino formyl chloride |
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