CN111943869A - Acrylonitrile polymerization inhibitor, preparation method and application thereof - Google Patents
Acrylonitrile polymerization inhibitor, preparation method and application thereof Download PDFInfo
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- CN111943869A CN111943869A CN201910413496.8A CN201910413496A CN111943869A CN 111943869 A CN111943869 A CN 111943869A CN 201910413496 A CN201910413496 A CN 201910413496A CN 111943869 A CN111943869 A CN 111943869A
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Abstract
The invention provides an acrylonitrile polymerization inhibitor, and a preparation method and application thereof. The acrylonitrile polymerization inhibitor comprises: the solvent, a component A, a component B and a component C, wherein the component A is a nitroxide free radical-N-heterocyclic compound shown in a formula (I), the component B is alkylamine, and the component C is a phenolic compound. The component A is a compound containing free radicals, and a large amount of free radicals are generated in the acrylonitrile production process, and can be captured by the component A and then inactivated, so that the component A has the function of preventing the polymerization and fouling of acrylonitrile. The alkylamine addition can play a role in slowly releasing free radicals in the component A, thereby being beneficial to reducing the probability of the inactivation of free genes generated by the component A due to self combination. The phenolic compound has reducibility, so that the addition of the phenolic compound can reduce free radicals in the production process of acrylonitrile, thereby achieving the purpose of preventing the polymerization of the acrylonitrile.
Description
Technical Field
The invention relates to the field of acrylonitrile production, and particularly relates to an acrylonitrile polymerization inhibitor, and a preparation method and application thereof.
Background
The acrylonitrile production device of the propylene ammoxidation method adopts an extraction rectification method and mainly comprises the working procedures of reaction, recovery, refining, four-effect evaporation and the like. The acrylonitrile device is often accompanied by polymerization reaction in normal operation, wherein the self-polymerization of acrylonitrile or the polymerization of other reaction byproducts such as hydrocyanic acid, acrolein, acrylamide and the like causes scaling problems in the system, and the generation of scaling substances shortens the operation period of equipment such as a tower, a reboiler, a heat exchanger and the like and reduces the production efficiency. In general, the acrylonitrile polymerization fouling of the recovery tower, the dehydro-cyanation tower and the finished product tower is severe, which seriously affects and restricts the long-period safe and stable operation of the acrylonitrile plant.
The most common polymerization inhibitor currently used in acrylonitrile plants is Hydroquinone (HQ), which is commonly added to the recovery column, the dehydrocyanation column, and the finishing column. However, the HQ has a poor polymerization inhibiting effect, so that the above-mentioned portion still produces more polymer during the production process, which is a major factor affecting the long-term operation of the acrylonitrile plant.
Disclosure of Invention
The invention mainly aims to provide an acrylonitrile polymerization inhibitor, a preparation method and application thereof, and aims to solve the problem of poor polymerization inhibition effect of the conventional acrylonitrile polymerization inhibitor.
In order to achieve the above object, according to one aspect of the present invention, there is provided an acrylonitrile polymerization inhibitor comprising: a solvent, a component A, a component B and a component C, wherein the component A is a nitroxide free radical-N-heterocyclic compound shown in a formula (I), the component B is alkylamine, the component C is a phenolic compound,
wherein R is1、R2、R3、R4And R5Each independently selected from hydrogen, hydroxy, carbonyl, alkyl, aryl, alkylaryl or arylalkyl, and R1、R2、R3、R4And R5The number of carbon atoms of (2) is not 0 at the same time.
Further, R1、R2、R3And R4Are all methyl, and R5Is hydroxyl or carbonyl.
Further, the alkylamine has a structure represented by formula (ii):
wherein R is5、R6And R7Each independently selected from hydrogen, hydroxy, carbonyl, alkyl, aryl, alkylaryl or arylalkyl, and R5、R6And R7The number of carbon atoms is not 0 at the same time; preferably, R5And R6Are all ethyl radicals, R7Is hydrogen or hydroxy.
Further, the phenolic compound is selected from hydroquinone and/or ether group substituted hydroquinone.
Further, the solvent is a mixed solution of high-boiling-point alcohol ether and low-melting-point alcohol, wherein the boiling point of the high-boiling-point alcohol ether is 140-240 ℃, and the melting point of the low-melting-point alcohol is-70 ℃ to-40 ℃.
Further, the weight ratio of the mixed solution of the high-boiling-point alcohol ether and the low-boiling-point alcohol is (25-30) to (33-40).
Furthermore, the amount of the solvent is 50-70 wt% based on the weight percentage of the acrylonitrile polymerization inhibitor.
Furthermore, the weight ratio of the component A, the component B and the component C is (10-25): (3-8): 20-30).
According to another aspect of the present invention, a preparation method of the acrylonitrile polymerization inhibitor is provided, wherein the preparation method comprises the step of heating and dissolving the solvent, the component A, the component B and the component C to obtain the acrylonitrile efficient polymerization inhibitor.
Further, the temperature in the heating process is 30-60 ℃.
According to another aspect of the present invention, there is provided a use of the above-mentioned acrylonitrile polymerization inhibitor in an acrylonitrile production process.
Further, in the application process, the weight concentration of the acrylonitrile polymerization inhibitor is 10-500 ppm, preferably 200-300 ppm.
By applying the technical scheme of the invention, the component A in the acrylonitrile polymerization inhibitor is a compound containing free radicals, a large amount of free radicals can be generated in the acrylonitrile production process, and the part of free radicals can be captured by the component A and then inactivated, so that the component A has the effect of preventing acrylonitrile from polymerizing and scaling. The alkylamine addition can play a role in slowly releasing free radicals in the component A, thereby being beneficial to reducing the probability of the inactivation of free genes generated by the component A due to self combination. The phenolic compound has reducibility, so that the addition of the phenolic compound can reduce free radicals in the production process of acrylonitrile, thereby achieving the purpose of preventing the polymerization of the acrylonitrile. The addition of the solvent facilitates the storage of the acrylonitrile polymerization inhibitor and ensures the stability of the polymerization inhibition effect. Under the action of the reasons, the acrylonitrile polymerization inhibitor with the composition can greatly reduce the polymerization scaling of acrylonitrile and prolong the operation period of an acrylonitrile preparation device.
Detailed Description
It should be noted that the embodiments and features of the embodiments in the present application may be combined with each other without conflict. The present invention will be described in detail with reference to examples.
As described in the background, the conventional acrylonitrile polymerization inhibitors have a problem of poor polymerization inhibition effect. In order to solve the above technical problem, the present application provides an acrylonitrile polymerization inhibitor, which comprises: a solvent, a component A, a component B and a component C, wherein the component A is a nitroxide free radical-N-heterocyclic compound shown in a formula (I), the component B is alkylamine, the component C is a phenolic compound,
wherein R is1、R2、R3、R4And R5Each independently selected from hydrogen, hydroxy, carbonyl, alkyl, aryl, alkylaryl or arylalkyl, and R1、R2、R3、R4And R5The number of carbon atoms of (2) is not 0 at the same time.
The component A in the acrylonitrile polymerization inhibitor is a compound containing free radicals, a large amount of free radicals are generated in the acrylonitrile production process, and the free radicals can be captured by the component A and then inactivated, so that the component A has the function of preventing the polymerization and scaling of acrylonitrile. The alkylamine addition can play a role in slowly releasing free radicals in the component A, thereby being beneficial to reducing the probability of the inactivation of free genes generated by the component A due to self combination. The phenolic compound has reducibility, so that the addition of the phenolic compound can reduce free radicals in the production process of acrylonitrile, thereby achieving the purpose of preventing the polymerization of the acrylonitrile. The addition of the solvent facilitates the storage of the acrylonitrile polymerization inhibitor and ensures the stability of the polymerization inhibition effect. Under the action of the reasons, the acrylonitrile polymerization inhibitor with the composition can greatly reduce the polymerization scaling of acrylonitrile and prolong the operation period of an acrylonitrile preparation device.
In order to further enhance the effect of inhibiting polymerization of the acrylonitrile polymerization inhibitor, preferably, R1、R2、R3And R4Are all methyl, and R5Is hydroxy or carbonyl (i.e., 4-hydroxy-2, 2,6, 6-tetramethylpiperidin-1-oxyl or 4-oxo-2, 2,6, 6-tetramethylpiperidin-1-oxyl).
In a preferred embodiment, the alkylamine has the structure shown in formula (II):
wherein R is5、R6And R7Each independently selected from hydrogen, hydroxy, carbonyl, alkyl, aryl, alkylaryl or arylalkyl, and R5、R6And R7The number of carbon atoms of (2) is not 0 at the same time. The alkylamine with the structure is beneficial to further controlling the generation rate of free radicals in the component A, thereby further reducing the polymerization fouling effect of acrylonitrile. More preferably, R5And R6Are all ethyl radicals, R7Hydrogen or hydroxy (i.e., diethylamine or diethylhydroxylamine).
The phenol compound in the acrylonitrile polymerization inhibitor can be selected from the types commonly used in the field. In a preferred embodiment, the phenolic compound is selected from hydroquinone and/or ether-substituted hydroquinone. Compared with other existing phenolic compounds, the two phenolic compounds are beneficial to further improving the polymerization inhibition effect of the acrylonitrile polymerization inhibitor.
The acrylonitrile polymerization inhibitor with the composition can greatly reduce the polymerization scaling of acrylonitrile and prolong the operation period of an acrylonitrile preparation device. In a preferred embodiment, the solvent is a mixed solution of high-boiling alcohol ether and low-melting alcohol, the boiling point of the high-boiling alcohol ether is 140-240 ℃, and the melting point of the low-melting alcohol is-70 ℃ to-40 ℃.
The above solvents include, but are not limited to, the above solvents, and the use of the above solvent composition is advantageous for improving the high-temperature and low-temperature stability of the acrylonitrile polymerization inhibitor. More preferably, the weight ratio of the mixed solution of the high-boiling alcohol ether and the low-boiling alcohol is (25-30): 33-40.
In order to ensure the polymerization inhibition effect of the acrylonitrile polymerization inhibitor, the amount of the solvent is preferably 50-70 wt% based on the weight percentage of the acrylonitrile polymerization inhibitor.
In order to further exert the synergistic effect of the component A, the component B and the component C to improve the polymerization inhibition effect of the acrylonitrile polymerization inhibitor, the weight ratio of the component A, the component B and the component C is preferably (10-25): (3-8): (20-30).
The other aspect of the application also provides a preparation method of the acrylonitrile polymerization inhibitor, and the preparation method comprises the step of heating and dissolving the solvent, the component A, the component B and the component C to obtain the acrylonitrile efficient polymerization inhibitor.
The component A in the acrylonitrile polymerization inhibitor is a compound containing free radicals, a large amount of free radicals are generated in the acrylonitrile production process, and the free radicals can be captured by the component A and then inactivated, so that the component A has the function of preventing the polymerization and scaling of acrylonitrile. The alkylamine addition can play a role in slowly releasing free radicals in the component A, thereby being beneficial to reducing the probability of the inactivation of free genes generated by the component A due to self combination. The phenolic compound has reducibility, so that the addition of the phenolic compound can reduce free radicals in the production process of acrylonitrile, thereby achieving the purpose of preventing the polymerization of the acrylonitrile. The addition of the solvent facilitates the storage of the acrylonitrile polymerization inhibitor and ensures the stability of the polymerization inhibition effect. Under the action of the reasons, the acrylonitrile polymerization inhibitor with the composition can greatly reduce the polymerization scaling of acrylonitrile and prolong the operation period of an acrylonitrile preparation device.
The heating temperature in the above-mentioned preparation process is not particularly limited as long as the raw materials can be dissolved to form a clear solution. Preferably, the temperature of the heating process is 30-60 ℃.
Preferably, the preparation method of the high-efficiency polymerization inhibitor for acrylonitrile comprises the following steps:
s1: preparing a mixed solution of high-boiling-point alcohol ether and low-boiling-point alcohol as a solvent;
s2: a polymerization inhibitor main body is prepared by a component A, a component B and a component C, wherein the component A is 4-hydroxy-2, 2,6, 6-tetramethylpiperidine-1-oxyl or 4-oxo-2, 2,6, 6-tetramethylpiperidine-1-oxyl, the component B is diethylamine or diethylhydroxylamine, and the component C is hydroquinone.
S3: and (4) dropwise adding the solvent prepared in the step (S1) into the main polymerization inhibitor prepared in the step (S2), and uniformly stirring at 30-60 ℃ to obtain clear transparent liquid, namely the acrylonitrile high-efficiency polymerization inhibitor.
The application also provides an application of the acrylonitrile polymerization inhibitor in the acrylonitrile production process.
The component A in the acrylonitrile polymerization inhibitor is a compound containing free radicals, a large amount of free radicals are generated in the acrylonitrile production process, and the free radicals can be captured by the component A and then inactivated, so that the component A has the function of preventing the polymerization and scaling of acrylonitrile. The alkylamine addition can play a role in slowly releasing free radicals in the component A, thereby being beneficial to reducing the probability of the inactivation of free genes generated by the component A due to self combination. The phenolic compound has reducibility, so that the addition of the phenolic compound can reduce free radicals in the production process of acrylonitrile, thereby achieving the purpose of preventing the polymerization of the acrylonitrile. The addition of the solvent facilitates the storage of the acrylonitrile polymerization inhibitor and ensures the stability of the polymerization inhibition effect. Under the action of the reasons, the acrylonitrile polymerization inhibitor with the composition can greatly reduce the polymerization scaling of acrylonitrile and prolong the operation period of an acrylonitrile preparation device.
In order to further reduce the scaling rate of acrylonitrile, the weight concentration of the acrylonitrile polymerization inhibitor is preferably 10 to 500ppm, and more preferably 200 to 300 ppm.
The present application is described in further detail below with reference to specific examples, which should not be construed as limiting the scope of the invention as claimed.
The preparation process of the polymerization inhibitor comprises the following steps:
preparing a mixed solvent from high-boiling-point alcohol ether and low-boiling-point alcohol according to the weight ratio of 20:40, sequentially adding the component A, the component B and the component C into the mixed solvent according to the weight ratio of 15:6:20, and stirring at 60 ℃ to prepare 100g of the acrylonitrile high-efficiency polymerization inhibitor product. The specific compositions of the polymerization inhibitors in examples 1 to 9 and comparative examples 1 to 3 are shown in Table 1.
TABLE 1
| The raw materials used | Component A | Component B | Component C |
| Example 1 | 4-hydroxy-2, 2,6, 6-tetramethylpiperidine-1-oxyl radical | Diethylhydroxylamine | Hydroquinone |
| Example 2 | 4-hydroxy-2, 2,6, 6-tetramethylpiperidine-1-oxyl radical | Diethylhydroxylamine | Hydroquinone |
| Example 3 | 4-hydroxy-2, 2,6, 6-tetramethylpiperidine-1-oxyl radical | Diethylhydroxylamine | Hydroquinone |
| Example 4 | 4-hydroxy-2, 2,6, 6-tetramethylpiperidine-1-oxyl radical | Diethylhydroxylamine | Hydroquinone |
| Example 5 | 4-hydroxy-2, 2,6, 6-tetramethylpiperidine-1-oxyl radical | Diethylhydroxylamine | Hydroquinone |
| Example 6 | 4-hydroxy-2, 2,6, 6-tetramethylpiperidine-1-oxyl radical | Diethylhydroxylamine | P-methyl ether phenol |
| Example 7 | 4-hydroxy-2, 2,6, 6-tetramethylpiperidine-1-oxyl radical | Diethylamine | P-methyl ether phenol |
| Example 8 | 4-hydroxy-2, 2,6, 6-tetramethylpiperidine-1-oxyl radical | Diphenylhydroxylamine | P-methyl ether phenol |
| Example 9 | 4-oxo-2, 2,6, 6-tetramethylpiperidine-1-oxyl radical | Diethylhydroxylamine | P-methyl ether phenol |
| Comparative example 1 | 4-hydroxy-2, 2,6, 6-tetramethylpiperidine-1-oxyl radical | -- | -- |
| Comparative example 2 | -- | Diethylhydroxylamine | -- |
| Comparative example 3 | -- | -- | Hydroquinone |
The polymerization inhibitors in examples 1 to 9 and comparative examples 1 to 3 were applied to the production process of acrylonitrile to test the performance of the polymerization inhibitors. The method comprises the following specific steps:
adding 100g of anhydrous polymerization inhibitor-free acrylonitrile into a 250ml three-neck flask, and then adding a proper amount of acrylonitrile polymerization inhibitor and initiator (benzoyl peroxide); placing the three-neck flask in a constant-temperature water bath at 70 ℃, cooling and fully refluxing the three-neck flask under the stirring condition, and recording the time of the polymerization reaction of the acrylonitrile in the three-neck flask, namely the time of changing from colorless transparency to yellow transparency and then to turbidity. The compositions of the polymerization inhibitors used in comparative examples 1 to 3 and examples 1 to 9 according to the invention are shown in Table 2 (the data in the tables are parts by weight).
TABLE 2
| The raw materials used | Component A | Component B | Component C |
| Example 1 | 10 | 5 | 20 |
| Example 2 | 12 | 4 | 20 |
| Example 3 | 12 | 5 | 20 |
| Example 4 | 15 | 3 | 20 |
| Example 5 | 10 | 5 | 15 |
| Example 6 | 12 | 5 | 20 |
| Example 7 | 8 | 5 | 20 |
| Example 8 | 9 | 5 | 20 |
| Example 9 | 11 | 5 | 20 |
| Comparative example 1 | 10 | -- | -- |
| Comparative example 2 | -- | 5 | -- |
| Comparative example 3 | -- | -- | 20 |
Adding a proper amount of polymerization inhibitor into 100g of acrylonitrile, carrying out total reflux operation under the following conditions (the operation temperature is 70 ℃, and a proper amount of initiator is added), and then recording blank and the polymerization initiation time of acrylonitrile added with different polymerization inhibitor products. Comparative example 7 shows the results of the application without addition of polymerization inhibitor. In comparative examples 1 to 6, the polymerization inhibitors were 4-hydroxy-2, 2,6, 6-tetramethylpiperidine-1-oxyl, diethylhydroxylamine, hydroquinone, foreign product A (brand EC3457A) and foreign product B (brand DA7641) in this order. Examples 1 to 9 are the polymerization inhibitors of examples 1 to 9 in the production example of the acrylonitrile polymerization inhibitor, respectively, and the results of the amount of the polymerization inhibitor and the polymerization initiation time are shown in Table 3.
TABLE 3
As can be seen from Table 3, the product of the invention has a polymerization inhibiting effect on acrylonitrile which is far greater than that of hydroquinone and is superior to the similar acrylonitrile polymerization inhibiting products abroad under the same concentration.
The results of the use of the inhibitor from example 2 at different concentrations used are shown in Table 4. The toxicity of hydroquinone, foreign product A, foreign product B and the inhibitor of example 1 was tested and the results are shown in Table 5.
TABLE 4
| Concentration of polymerization inhibitor ppm | 50 | 80 | 100 | 150 | 300 |
| Time to initiate polymerization, min | 30 | 60 | 128 | 138 | 400 |
As can be seen from Table 4, the polymerization inhibiting effect of the product of the invention is correspondingly enhanced along with the increase of the injection concentration, and the economic and effective injection concentration is between 200 and 300 ppm.
TABLE 5
As can be seen from the toxicity comparison data in Table 5, the product of the present invention is a low toxicity environment-friendly product.
From the above description, it can be seen that the above-described embodiments of the present invention achieve the following technical effects: the component A in the acrylonitrile polymerization inhibitor is a compound containing free radicals, a large amount of free radicals are generated in the acrylonitrile production process, and the free radicals can be captured by the component A and then inactivated, so that the component A has the function of preventing the polymerization and scaling of acrylonitrile. The alkylamine addition can play a role in slowly releasing free radicals in the component A, thereby being beneficial to reducing the probability of the inactivation of free genes generated by the component A due to self combination. The phenolic compound has reducibility, so that the addition of the phenolic compound can reduce free radicals in the production process of acrylonitrile, thereby achieving the purpose of preventing the polymerization of the acrylonitrile. The addition of the solvent facilitates the storage of the acrylonitrile polymerization inhibitor and ensures the stability of the polymerization inhibition effect. Under the action of the reasons, the acrylonitrile polymerization inhibitor with the composition can greatly reduce the polymerization scaling of acrylonitrile and prolong the operation period of an acrylonitrile preparation device.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (12)
1. An acrylonitrile polymerization inhibitor, comprising: the solvent, a component A, a component B and a component C, wherein the component A is a nitroxide free radical-N-heterocyclic compound shown in a formula (I), the component B is alkylamine, the component C is a phenolic compound,
wherein, R is1The R is2The R is3The R is4And said R5Are each independently selected from hydrogenHydroxy, carbonyl, alkyl, aryl, alkylaryl or arylalkyl, and said R1The R is2The R is3The R is4And said R5The number of carbon atoms of (2) is not 0 at the same time.
2. The acrylonitrile polymerization inhibitor according to claim 1, wherein R is1The R is2The R is3And said R4Are both methyl, and R is5Is hydroxyl or carbonyl.
3. The acrylonitrile polymerization inhibitor according to claim 1 or 2, wherein the alkylamine has a structure represented by formula (ii):
wherein, R is5The R is6And said R7Each independently selected from hydrogen, hydroxy, carbonyl, alkyl, aryl, alkylaryl or arylalkyl, and said R5The R is6And said R7The number of carbon atoms is not 0 at the same time;
preferably, said R is5And said R6Are all ethyl, said R7Is hydrogen or hydroxy.
4. The acrylonitrile polymerization inhibitor according to claim 3, wherein the phenolic compound is selected from hydroquinone and/or ether-substituted hydroquinone.
5. The acrylonitrile polymerization inhibitor according to any one of claims 1 to 4, wherein the solvent is a mixed solution of a high-boiling alcohol ether and a low-melting alcohol, wherein the high-boiling alcohol ether has a boiling point of 140 ℃ to 240 ℃ and the low-melting alcohol has a melting point of-70 ℃ to-40 ℃.
6. The acrylonitrile polymerization inhibitor according to claim 5, wherein the weight ratio of the mixed solution of the high-boiling alcohol ether and the low-boiling alcohol is (25-30) to (33-40).
7. The acrylonitrile polymerization inhibitor according to claim 5, wherein the solvent is used in an amount of 50 to 70 wt% based on the weight of the acrylonitrile polymerization inhibitor.
8. The acrylonitrile polymerization inhibitor as claimed in claim 1, wherein the weight ratio of the component A, the component B and the component C is (10-25): (3-8): (20-30).
9. The method for preparing the acrylonitrile polymerization inhibitor according to any one of claims 1 to 8, wherein the method comprises heating and dissolving a solvent, the component A, the component B and the component C to obtain the high-efficiency acrylonitrile polymerization inhibitor.
10. The method according to claim 9, wherein the temperature of the heating process is 30 to 60 ℃.
11. Use of an acrylonitrile polymerization inhibitor according to any one of claims 1 to 8 in the production of acrylonitrile.
12. The use according to claim 11, wherein the concentration by weight of the acrylonitrile polymerization inhibitor during the use is 10 to 500ppm, preferably 200 to 300 ppm.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100168434A1 (en) * | 2005-10-20 | 2010-07-01 | A H Marks And Company Limited | Inhibition of polymerisation |
| CN102295499A (en) * | 2010-06-25 | 2011-12-28 | 中国石油化工股份有限公司 | Polymerization inhibitor for inhibiting polymerization of vinyl compound |
| CN102947260A (en) * | 2010-06-18 | 2013-02-27 | 伯东株式会社 | Polymerization inhibitor composition for vinyl compounds and method for inhibiting the polymerization of vinyl compounds which includes using same |
| CN103339179A (en) * | 2011-02-03 | 2013-10-02 | 纳尔科公司 | Multi-component polymerization inhibitors for ethylenically unsaturated monomers |
-
2019
- 2019-05-17 CN CN201910413496.8A patent/CN111943869A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100168434A1 (en) * | 2005-10-20 | 2010-07-01 | A H Marks And Company Limited | Inhibition of polymerisation |
| CN102947260A (en) * | 2010-06-18 | 2013-02-27 | 伯东株式会社 | Polymerization inhibitor composition for vinyl compounds and method for inhibiting the polymerization of vinyl compounds which includes using same |
| CN102295499A (en) * | 2010-06-25 | 2011-12-28 | 中国石油化工股份有限公司 | Polymerization inhibitor for inhibiting polymerization of vinyl compound |
| CN103339179A (en) * | 2011-02-03 | 2013-10-02 | 纳尔科公司 | Multi-component polymerization inhibitors for ethylenically unsaturated monomers |
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Application publication date: 20201117 |