CN114835549A - Anti-freezing water-soluble styrene polymerization inhibitor and preparation method thereof - Google Patents
Anti-freezing water-soluble styrene polymerization inhibitor and preparation method thereof Download PDFInfo
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- CN114835549A CN114835549A CN202210493320.XA CN202210493320A CN114835549A CN 114835549 A CN114835549 A CN 114835549A CN 202210493320 A CN202210493320 A CN 202210493320A CN 114835549 A CN114835549 A CN 114835549A
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Abstract
The invention provides an anti-freezing water-soluble styrene polymerization inhibitor and a preparation method thereof, wherein the anti-freezing water-soluble styrene polymerization inhibitor comprises the following raw material components in parts by mass: 2-10 parts of nitroxide free radicals, 3-8 parts of quinone methyl compounds, 1-4 parts of stabilizer compounds, 0.1-0.5 part of antifreeze, 0.01-0.15 part of silicon phosphorus crystals and 40-70 parts of water. The preparation method comprises the following steps: step one, mixing an antifreezing agent, phosphorus crystals and a solvent, and uniformly stirring for later use; step two, adding the nitroxide free radicals into the mixed solution obtained in the step one, and uniformly stirring for later use; step three, adding a stabilizer compound into the mixed solution obtained in the step two, and uniformly stirring; and step four, adding the quinone methyl compound into the mixed solution obtained in the step three under the stirring state, and uniformly stirring to obtain the anti-freezing water-soluble styrene polymerization inhibitor. The styrene polymerization inhibitor adopts water as a solvent and has excellent anti-freezing effect.
Description
Technical Field
The invention relates to the technical field of polymerization inhibitor materials, in particular to an anti-freezing water-soluble styrene polymerization inhibitor and a preparation method thereof.
Background
Styrene is widely used as a monomer with wide application, and is widely applied to the fields of synthetic polymer materials, coatings, pesticides, medicines, dyes and the like. In the production process of styrene, ethylbenzene is dehydrogenated and then rectified to prepare high-purity styrene monomer, and the styrene monomer is very active and can be polymerized at normal temperature, and the higher the temperature is, the easier the polymerization is. In order to prevent the polymerization of vinyl monomers during storage, transportation, etc., a small amount of polymerization inhibitor is often added to the monomers and removed before use.
The polymerization inhibitor is an industrial aid, and is generally used for preventing polymerization from proceeding, and the polymerization inhibitor molecule reacts with chain radicals to form non-radical substances or low-activity radicals which cannot be initiated, thereby terminating the polymerization. Generally, the polymerization inhibitor is a solid substance and has low volatility, and it can be removed when the monomer is distilled.
At present, most of the styrene polymerization inhibitor products on the market adopt organic solvents, such as ethylbenzene and the like, as the components. If ethylbenzene is used as a solvent, a certain amount of effective substances are consumed by the polymerization inhibitor during sale, transportation and storage, so that the service performance of the polymerization inhibitor is influenced. Therefore, the production of styrene polymerization inhibitor by adopting other solvents becomes a research hotspot in the industry.
Disclosure of Invention
In order to solve the problems mentioned in the background art, when ethylbenzene is used as a solvent in a styrene polymerization inhibitor product, a certain amount of effective substances are consumed during sale, transportation and storage. The invention provides a water-soluble styrene polymerization inhibitor which adopts water as a solvent and has an anti-freezing effect. The specific scheme is as follows:
an anti-freezing water-soluble styrene polymerization inhibitor comprises the following raw material components in parts by mass: 2-10 parts of nitroxide free radicals, 3-8 parts of quinone methyl compounds, 1-4 parts of stabilizer compounds, 0.1-0.5 part of antifreeze, 0.01-0.15 part of silicon phosphorus crystals and 40-70 parts of water.
In the implementation of the above embodiment, the nitroxide radical is preferably one or more of di-tert-butyl nitroxide radical, 4-hydroxy-2, 2,6, 6-tetramethylpiperidine nitroxide radical, 4-carbonyl-2, 2,6, 6-tetramethylpiperidine nitroxide radical, and 4-methoxy-2, 2,6, 6-tetramethylpiperidine nitroxide radical.
In carrying out the above example, preferably, the quinone methyl compound is 4-benzylidene-2, 6-di-tert-butyl-cyclohexa-2, 5-dienone.
In practicing the above embodiments, preferably, the stabilizer compound comprises a primary or secondary amine group.
In carrying out the above embodiment, preferably, the stabilizer compound is one or more of a cyclic secondary amine, a heterocyclic secondary amine, an aryl diamine, an aryl polyamine, and a polyalkyl polyamine.
In carrying out the above embodiment, preferably, the antifreeze is one or more of ethylene glycol, propylene glycol and glycerin.
In carrying out the above embodiment, preferably, the mass ratio of the quinone methyl compound to the nitroxide radical is 0.8:1 to 1: 1.
The preparation method of the anti-freezing water-soluble styrene polymerization inhibitor comprises the following steps:
step one, mixing an antifreezing agent, phosphorus crystals and a solvent, and uniformly stirring for later use;
step two, adding the nitroxide free radicals into the mixed solution obtained in the step one, and uniformly stirring for later use;
step three, adding a stabilizer compound into the mixed solution obtained in the step two, and uniformly stirring;
and step four, adding the quinone methyl compound into the mixed solution obtained in the step three under the stirring state, and uniformly stirring to obtain the anti-freezing water-soluble styrene polymerization inhibitor.
When the above embodiment is implemented, preferably, the stirring speed in the first step to the fourth step is 80-200r/min, and the stirring time is 2-7 min.
In carrying out the above embodiment, it is preferred that all of the first to fourth steps are carried out at 22 to 27 ℃.
Compared with the prior art, the invention has the following beneficial effects:
1. the raw material components of the invention are added with 2-10 parts of nitroxide free radical, 3-8 parts of quinone methyl compound and stabilizer compound with primary amine group or secondary amine group, when the nitroxide free radical and the stabilizer compound are used together, the stabilizer compound can improve the functional group of the nitroxide free radical. Further, the stabilizer compound can block antagonism when the nitroxide radical and the quinone methyl compound are combined, so that the polymerization inhibitor has greater anti-polymerization activity.
2. The silicon-phosphorus crystal is added in the raw material components, and the silicon-phosphorus crystal can seal iron ions, so that the iron ions are relieved from participating in the catalytic polymerization reaction of styrene. By reducing the catalytic activity of iron ions, the external inducing factor of polymerization of styrene monomer is reduced from the source, and the polymerized part is dispersed and cleaned, and the polymerization inhibition effect is improved through various ways.
3. The raw material components of the invention are mixed with nitroxide free radicals and stabilizer compounds with primary or secondary amine groups to form a composition for inhibiting the polymerization of monomers, which can improve the polymerization inhibition effect.
4. The raw material components of the invention are added with the antifreeze, which can reduce the freezing point of the water-soluble styrene polymerization inhibitor, improve the antifreeze capacity and facilitate the transportation and storage of the water-soluble styrene polymerization inhibitor in a low-temperature environment.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The experimental drugs and reagents used in the examples and comparative examples of the present invention are described below:
nitroxide free radical: 4-methoxy-2, 2,6, 6-tetramethylpiperidine nitroxide radical;
quinone methyl compound: 4-benzylidene-2, 6-di-tert-butyl-cyclohexa-2, 5-dienone;
stabilizer compounds: a cyclic secondary amine;
an antifreezing agent: ethylene glycol;
solvent: and (3) water.
It should be noted that the reagents or apparatuses used in the examples are not indicated by the manufacturer, but those not indicated by the specific techniques or conditions described in the literature in the art or by the specifications of the products are all conventional products commercially available. The operating room temperature was 22 ℃.
Example 1
An anti-freezing water-soluble styrene polymerization inhibitor comprises the following raw material components in parts by mass: 2 parts of 4-methoxy-2, 2,6, 6-tetramethyl piperidine nitroxide free radical, 8 parts of 4-benzylidene-2, 6-di-tert-butyl-cyclohexyl-2, 5-dienone, 4 parts of cyclic secondary amine, 0.5 part of ethylene glycol, 0.15 part of silicon phosphorus crystal and 70 parts of water.
The preparation method comprises the following steps:
step one, mixing and stirring ethylene glycol, silicon-phosphorus crystals and water at room temperature, wherein the stirring speed is 120r/min, the stirring time is 3min, and stirring for later use;
step two, adding 4-methoxy-2, 2,6, 6-tetramethyl piperidine nitroxide free radical into the mixed solution obtained in the step one at room temperature, stirring at the stirring speed of 120r/min for 5min, and stirring for later use;
step three, adding cyclic secondary amine into the mixed solution obtained in the step two at room temperature, and uniformly stirring at a stirring speed of 120r/min for 5 min;
and step four, adding 4-benzylidene-2, 6-di-tert-butyl-cyclohexa-2, 5-dienone into the mixed solution obtained in the step three while stirring at room temperature, wherein the stirring speed is 150r/min, the stirring time is 7min, and the antifreezing water-soluble styrene polymerization inhibitor is obtained after uniform stirring.
Example 2
An anti-freezing water-soluble styrene polymerization inhibitor comprises the following raw material components in parts by mass: 10 parts of 4-methoxy-2, 2,6, 6-tetramethyl piperidine nitroxide free radical, 3 parts of 4-benzylidene-2, 6-di-tert-butyl-cyclohexyl-2, 5-dienone, 4 parts of cyclic secondary amine, 0.5 part of ethylene glycol, 0.15 part of silicon phosphorus crystal and 70 parts of water.
The preparation method comprises the following steps:
step one, mixing and stirring ethylene glycol, silicon-phosphorus crystals and water at room temperature, wherein the stirring speed is 120r/min, the stirring time is 3min, and stirring for later use;
step two, adding 4-methoxy-2, 2,6, 6-tetramethyl piperidine nitroxide free radical into the mixed solution obtained in the step one at room temperature, stirring at the stirring speed of 120r/min for 5min, and stirring for later use;
step three, adding cyclic secondary amine into the mixed solution obtained in the step two at room temperature, and uniformly stirring at a stirring speed of 120r/min for 5 min;
and step four, adding 4-benzylidene-2, 6-di-tert-butyl-cyclohexa-2, 5-dienone into the mixed solution obtained in the step three while stirring at room temperature, wherein the stirring speed is 150r/min, the stirring time is 7min, and the antifreezing water-soluble styrene polymerization inhibitor is obtained after uniform stirring.
Example 3
An anti-freezing water-soluble styrene polymerization inhibitor comprises the following raw material components in parts by mass: 10 parts of 4-methoxy-2, 2,6, 6-tetramethyl piperidine nitroxide free radical, 8 parts of 4-benzylidene-2, 6-di-tert-butyl-cyclohexyl-2, 5-dienone, 1 part of cyclic secondary amine, 0.5 part of ethylene glycol, 0.15 part of silicon phosphorus crystal and 70 parts of water.
The preparation method comprises the following steps:
step one, mixing and stirring ethylene glycol, silicon-phosphorus crystals and water at room temperature, wherein the stirring speed is 120r/min, the stirring time is 3min, and stirring for later use;
step two, adding 4-methoxy-2, 2,6, 6-tetramethyl piperidine nitroxide free radical into the mixed solution obtained in the step one at room temperature, stirring at the stirring speed of 120r/min for 5min, and stirring for later use;
step three, adding cyclic secondary amine into the mixed solution obtained in the step two at room temperature, and uniformly stirring at a stirring speed of 120r/min for 5 min;
and step four, adding 4-benzylidene-2, 6-di-tert-butyl-cyclohexa-2, 5-dienone into the mixed solution obtained in the step three while stirring at room temperature, wherein the stirring speed is 150r/min, the stirring time is 7min, and the antifreezing water-soluble styrene polymerization inhibitor is obtained after uniform stirring.
Example 4
An anti-freezing water-soluble styrene polymerization inhibitor comprises the following raw material components in parts by mass: 10 parts of 4-methoxy-2, 2,6, 6-tetramethyl piperidine nitroxide free radical, 8 parts of 4-benzylidene-2, 6-di-tert-butyl-cyclohexyl-2, 5-dienone, 4 parts of cyclic secondary amine, 0.1 part of ethylene glycol, 0.15 part of silicon phosphorus crystal and 70 parts of water.
The preparation method comprises the following steps:
step one, mixing and stirring ethylene glycol, silicon-phosphorus crystals and water at room temperature, wherein the stirring speed is 120r/min, the stirring time is 3min, and stirring for later use;
step two, adding 4-methoxy-2, 2,6, 6-tetramethyl piperidine nitroxide free radical into the mixed solution obtained in the step one at room temperature, stirring at the stirring speed of 120r/min for 5min, and stirring for later use;
step three, adding cyclic secondary amine into the mixed solution obtained in the step two at room temperature, and uniformly stirring at a stirring speed of 120r/min for 5 min;
and step four, adding 4-benzylidene-2, 6-di-tert-butyl-cyclohexa-2, 5-dienone into the mixed solution obtained in the step three while stirring at room temperature, wherein the stirring speed is 150r/min, the stirring time is 7min, and the antifreezing water-soluble styrene polymerization inhibitor is obtained after uniform stirring.
Example 5
An anti-freezing water-soluble styrene polymerization inhibitor comprises the following raw material components in parts by mass: 10 parts of 4-methoxy-2, 2,6, 6-tetramethyl piperidine nitroxide free radical, 8 parts of 4-benzylidene-2, 6-di-tert-butyl-cyclohexyl-2, 5-dienone, 4 parts of cyclic secondary amine, 0.5 part of ethylene glycol, 0.01 part of silicon phosphorus crystal and 70 parts of water.
The preparation method comprises the following steps:
step one, mixing and stirring ethylene glycol, silicon-phosphorus crystals and water at room temperature, wherein the stirring speed is 120r/min, the stirring time is 3min, and stirring for later use;
step two, adding 4-methoxy-2, 2,6, 6-tetramethyl piperidine nitroxide free radical into the mixed solution obtained in the step one at room temperature, stirring at the stirring speed of 120r/min for 5min, and stirring for later use;
step three, adding cyclic secondary amine into the mixed solution obtained in the step two at room temperature, and uniformly stirring at a stirring speed of 120r/min for 5 min;
and step four, adding 4-benzylidene-2, 6-di-tert-butyl-cyclohexa-2, 5-dienone into the mixed solution in the step three while stirring at room temperature, wherein the stirring speed is 150r/min, the stirring time is 7min, and the antifreeze water-soluble styrene polymerization inhibitor is obtained after uniform stirring.
Comparative example 1
Commercial 701 inhibitor.
Comparative example 2
An anti-freezing water-soluble styrene polymerization inhibitor comprises the following raw material components in parts by mass: 2 parts of 4-methoxy-2, 2,6, 6-tetramethyl piperidine nitroxide free radical, 8 parts of 4-benzylidene-2, 6-di-tert-butyl-cyclohexyl-2, 5-dienone, 0.5 part of ethylene glycol, 0.15 part of silicon phosphorus crystal and 70 parts of water.
The preparation method comprises the following steps:
step one, mixing and stirring ethylene glycol, silicon-phosphorus crystals and water at room temperature, wherein the stirring speed is 120r/min, the stirring time is 3min, and stirring for later use;
step two, adding 4-methoxy-2, 2,6, 6-tetramethyl piperidine nitroxide free radical into the mixed solution obtained in the step one at room temperature, stirring at the stirring speed of 120r/min for 5min, and stirring for later use;
and step three, adding 4-benzylidene-2, 6-di-tert-butyl-cyclohexyl-2, 5-dienone into the mixed solution in the step two while stirring at room temperature, wherein the stirring speed is 150r/min, the stirring time is 7min, and the antifreezing water-soluble styrene polymerization inhibitor is obtained after uniform stirring.
Comparative example 3
An anti-freezing water-soluble styrene polymerization inhibitor comprises the following raw material components in parts by mass: 8 parts of 4-benzylidene-2, 6-di-tert-butyl-cyclohexyl-2, 5-dienone, 4 parts of cyclic secondary amine, 0.5 part of ethylene glycol, 0.15 part of silicon-phosphorus crystal and 70 parts of water.
The preparation method comprises the following steps:
step one, mixing and stirring ethylene glycol and water at room temperature, wherein the stirring speed is 120r/min, the stirring time is 3min, and stirring is carried out for later use;
and step two, adding cyclic secondary amine and 4-benzylidene-2, 6-di-tert-butyl-cyclohexyl-2, 5-dienone into the mixed solution obtained in the step one at room temperature, stirring at the speed of 150r/min for 7min, and uniformly stirring to obtain the anti-freezing water-soluble styrene polymerization inhibitor.
The styrene polymerization inhibitors obtained in examples 1 to 5 and comparative examples 1 to 3 were each subjected to the following tests:
test one, the commercial styrene is subjected to alkali washing and distillation to obtain the styrene purifying agent without any polymerization inhibitor. Respectively adding 500ppm of styrene polymerization inhibitor into the styrene purifying agent, reacting for 30min under the conditions of nitrogen protection and 120 ℃, then precipitating styrene polymer by using methanol or ethanol, filtering, drying, weighing, and calculating the mass percentage of the styrene polymer equivalent to the styrene purifying agent as the polymer content.
And testing II, performing alkali washing and distillation on the commercial styrene to obtain the styrene pure agent without any polymerization inhibitor. Respectively adding 500ppm of styrene polymerization inhibitor into the styrene purifying agent, reacting for 60min under the conditions of nitrogen protection and 120 ℃, then precipitating styrene polymer by using methanol or ethanol, filtering, drying, weighing, and calculating the mass percentage of the styrene polymer equivalent to the styrene purifying agent as the polymer content.
Wherein the addition amount of the styrene polymerization inhibitor is 0.01 percent of the mass of the crude styrene product. Wherein the unit of the polymer content is percentage (%).
The test results of test one are shown in table 1;
TABLE 1
The test results of test two are shown in table 2:
TABLE 2
From Table 1, it can be seen that the difference in the polymer contents between examples 1 to 5 and comparative examples 1 to 3 is small, and the polymer contents of examples 1 to 5 are smaller than those of comparative examples 1 to 3; from Table 2, it can be seen that the difference in polymer contents is large between examples 1-5 and comparative examples 1-3, and the polymer contents of examples 1-5 are smaller than those of comparative examples 1-3. Comparing tables 1 and 2, it can be seen that examples 1-5 had a smaller increase in polymer content than comparative examples 1-3. It can be seen that the styrene polymerization inhibitors of examples 1 to 5 have better polymerization inhibiting effect and longer action time than the conventional commercial styrene polymerization inhibitors.
The experiments prove that the polymerization inhibitor obtained by adding the nitroxide free radical, the quinone methyl compound and the stabilizer compound into the components has better polymerization inhibition effect and longer action time through the synergistic action of the nitroxide free radical, the quinone methyl compound and the stabilizer compound.
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; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (10)
1. An anti-freezing water-soluble styrene polymerization inhibitor is characterized by comprising the following raw materials in parts by mass: 2-10 parts of nitroxide free radicals, 3-8 parts of quinone methyl compounds, 1-4 parts of stabilizer compounds, 0.1-0.5 part of antifreeze, 0.01-0.15 part of silicon phosphorus crystals and 40-70 parts of water.
2. The anti-freeze water-soluble styrene polymerization inhibitor according to claim 1, wherein the nitroxide radical is one or more of di-tert-butyl nitroxide radical, 4-hydroxy-2, 2,6, 6-tetramethylpiperidine nitroxide radical, 4-carbonyl-2, 2,6, 6-tetramethylpiperidine nitroxide radical, 4-methoxy-2, 2,6, 6-tetramethylpiperidine nitroxide radical.
3. The antifreeze water-soluble styrene polymerization inhibitor according to claim 1, wherein said quinone methyl compound is 4-benzylidene-2, 6-di-t-butyl-cyclohexa-2, 5-dienone.
4. The antifreeze water-soluble styrene polymerization inhibitor according to claim 1, wherein said stabilizer compound comprises a primary or secondary amine group.
5. The antifreeze water-soluble styrene polymerization inhibitor according to claim 4, wherein said stabilizer compound is one or more of a cyclic secondary amine, a heterocyclic secondary amine, an aryldiamine, an arylpolyamine and a polyalkylpolyamine.
6. The anti-freeze water-soluble styrene polymerization inhibitor according to claim 1, wherein the anti-freeze agent is one or more of ethylene glycol, propylene glycol and glycerol.
7. The anti-freeze water-soluble styrene polymerization inhibitor according to claim 1, wherein the mass ratio of the quinone methyl compound to the nitroxide radical is 0.8:1 to 1: 1.
8. A preparation method of the anti-freezing water-soluble styrene polymerization inhibitor as claimed in any one of claims 1 to 7, characterized by comprising the following steps:
step one, mixing an antifreezing agent, phosphorus crystals and a solvent, and uniformly stirring for later use;
step two, adding the nitroxide free radicals into the mixed solution obtained in the step one, and uniformly stirring for later use;
step three, adding a stabilizer compound into the mixed solution obtained in the step two, and uniformly stirring;
and step four, adding the quinone methyl compound into the mixed solution obtained in the step three under the stirring state, and uniformly stirring to obtain the anti-freezing water-soluble styrene polymerization inhibitor.
9. The method for preparing the anti-freeze water-soluble styrene polymerization inhibitor according to claim 8, wherein the stirring speed in the first step and the fourth step is 80-200r/min, and the stirring time is 2-7 min.
10. The method for preparing anti-freeze water-soluble styrene polymerization inhibitor according to claim 8, wherein the first to fourth steps are performed at 22-27 ℃.
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| CN116396140A (en) * | 2023-04-26 | 2023-07-07 | 江苏太湖新材料控股有限公司 | Styrene polymerization inhibitor and preparation method thereof |
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| US20200017610A1 (en) * | 2018-07-13 | 2020-01-16 | Ecolab Usa Inc. | Polymerization inhibitor and retarder compositions with amine stabilizer |
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| US20200017610A1 (en) * | 2018-07-13 | 2020-01-16 | Ecolab Usa Inc. | Polymerization inhibitor and retarder compositions with amine stabilizer |
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| 朱仙鼎: "《中国内燃机工程师手册》", 30 September 2000, 上海科学技术出版社 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116396140A (en) * | 2023-04-26 | 2023-07-07 | 江苏太湖新材料控股有限公司 | Styrene polymerization inhibitor and preparation method thereof |
| CN116396140B (en) * | 2023-04-26 | 2023-10-27 | 江苏太湖新材料控股有限公司 | Styrene polymerization inhibitor and preparation method thereof |
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