CN109796392B - Synthesis method of methyl ethyl ketone peroxide without three wastes - Google Patents
Synthesis method of methyl ethyl ketone peroxide without three wastes Download PDFInfo
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Abstract
The invention provides a synthesis method of methyl ethyl ketone peroxide without three wastes. The technical scheme is that hydrogen peroxide and butanone are used as raw materials, dimethyl phthalate is used as a solvent, the reaction is carried out by a back-dropping butanone method, and after the reaction is finished, a hydrophilic solvent is added into the reaction again to realize that a product liquid is a homogeneous phase. The method breaks through the technical prejudice that butanone and a solvent are mixed firstly, an acidic catalyst is added, and hydrogen peroxide is added dropwise in the traditional synthetic method, and the method adopts the hydrogen peroxide as a base material and utilizes the acidity of the hydrogen peroxide to catalyze automatically. The reaction process of the invention is very stable, the synthesis process of the product does not generate any three wastes, and the obtained product has extremely good stability and good service performance.
Description
Technical Field
The invention relates to the technical field of chemical engineering, in particular to a synthetic method of methyl ethyl ketone peroxide without three wastes.
Background
Methyl ethyl ketone peroxide is an initiator of unsaturated polyester resin and has an important influence on the performance of the unsaturated polyester resin. Unsaturated polyester resin is an important high molecular material, the output is in the million tons level, the application range is extremely wide, the unsaturated polyester resin comprises more than 90% of varieties in more than ten fields of airplanes, high-speed rails, ships, yachts, wind power generation, glass fiber reinforced plastic anticorrosive materials and the like, and the unsaturated polyester resin material is synthesized by using methyl ethyl ketone peroxide as an initiator, so that the demand of the polyester industry on the methyl ethyl ketone peroxide product is very large, and the dependence is very strong.
The conventional synthesis method of methyl ethyl ketone peroxide is to use methyl ethyl ketone, and in the presence of a solvent and an acid catalyst, the synthesis is carried out by dripping hydrogen peroxide, and many reports are reported in the former aspect, and only in the patent aspect, German patents DE4438147(1994), DE1243195, Hungarian patents HU.1977B, PCT patent WO0009478 (2000), Japanese patent JP45-19486(1970), Chinese patents CN107999011A (2018) and CN105237453A (2015) adopt the method, while Chinese patent CN18000161A adopts a double-flow parallel method, but still carries out the reaction under the condition of adding acid for catalysis, so that waste water still needs to be generated, and the method only solves the problem of continuous product synthesis.
The method for adding acid to catalyze the methyl ethyl ketone peroxide synthesis process has the disadvantages that the acid used in the conventional process comprises sulfuric acid, nitric acid, trichloroacetic acid and the like, sulfate radicals, nitrate radicals, chloride ions and the like introduced by the catalysts can seriously affect the stability of the methyl ethyl ketone peroxide product, so that after the reaction is finished, the product is generally required to be layered, so that the ions are dissolved in water and are separated out together with the water, thus, a certain amount of wastewater is generated in the synthesis process, the wastewater generally contains about 20% of peroxide by weight (calculated by hydrogen peroxide), and the wastewater is very dangerous because the wastewater contains sensitive factors of the peroxide such as the chloride ions, the sulfate ions, the nitrate ions and the like.
The self stability of methyl ethyl ketone peroxide products is also an important problem, the mode of adding methyl ethyl ketone dropwise is characterized in that a large amount of hydrogen peroxide exists in a system all the time, so the component proportion of the obtained products is greatly different from that of a process of adding hydrogen peroxide dropwise, the stability of the product composition generated by the method is obviously higher than that of the process of adding hydrogen peroxide dropwise, the detection result of the embodiment shows that the significance is very obvious, the storage period and the service performance of the product are improved, more importantly, if the product is unstable, the decomposed product can gradually react again to generate a new peroxide which is very sensitive to vibration, friction, ultraviolet light and the like, the compound can be separated out from the product at low temperature to form crystals, and once a large amount of the compound exists in the product, the explosion is very easy to be caused, and the methyl ethyl ketone dropwise adding scheme is adopted, the product stability problem is solved very effectively.
In the aspect of environmental protection, in recent years, with the increasing of the national requirement on the environment, the problem of waste water in the synthesis process of methyl ethyl ketone peroxide products is more and more prominent, in the traditional synthesis process, the synthesis process inevitably generates waste water, the waste water is not large in amount, but high in organic matter Content (COD) and extremely unstable, a large amount of oxygen escapes at normal temperature, heat is released, explosion is likely to occur when the temperature reaches the self-heating temperature, the waste water is not large in amount, but the difficulty in treatment is not small, in recent years, a resin catalysis method is created aiming at the problem of waste water stability, although the method relieves the introduction problem of ions, the recovery treatment process of resin is not only complicated, but also the cost is higher, and the ton consumption of the products is obviously increased. In summary, it is of great significance to find a methyl ethyl ketone peroxide synthesis method which does not produce waste water and has good use performance.
Disclosure of Invention
The invention aims to provide a synthetic method of methyl ethyl ketone peroxide without three wastes (waste gas, waste water and industrial residue) aiming at overcoming the technical defect of the prior art, and aims to solve the technical problem that the conventional synthetic method of methyl ethyl ketone peroxide can generate three wastes.
The invention also aims to solve the technical problem that the stability of the methyl ethyl ketone peroxide synthesized by the conventional method needs to be improved.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
a synthesis method of methyl ethyl ketone peroxide without three wastes (waste gas, waste water and industrial residue) generation comprises the following steps: adding hydrogen peroxide and dimethyl phthalate in a formula amount into a container, and continuously dropwise adding butanone into the container under the stirring condition until the reaction is finished. The method comprises the steps of firstly adding hydrogen peroxide and dimethyl phthalate into a reaction vessel, and dropwise adding butanone under the stirring condition so as to ensure that a system is always in a proper acidic range catalysis condition.
Preferably, in the dropwise adding process, the system temperature is 0-40 ℃; further preferably, the system temperature is 20-40 ℃.
Preferably, the molar ratio of the consumption of the hydrogen peroxide to the consumption of the butanone is 1.6-2.1: 1; further preferably, the molar ratio of the consumption of the hydrogen peroxide to the consumption of the butanone is 1.8-1.9: 1.
Preferably, the duration time of the dropwise addition is 0.5-3 h; further preferably, the duration time of the dropwise addition is 1.5-2.5 h.
Preferably, after the completion of the reaction, a hydrophilic solvent is added to the reaction system.
Preferably, after the reaction is finished, the hydrophilic solvent and the product stabilizer are added into the reaction system and stirred until the product stabilizer is dissolved.
Preferably, the hydrophilic solvent comprises ethylene glycol, monoethylene glycol or glycerol.
The invention provides a synthesis method of a methyl ethyl ketone peroxide product, which is stable in product and free from three wastes in the synthesis process. The technical scheme is that hydrogen peroxide and butanone are used as raw materials, dimethyl phthalate is used as a solvent, the reaction is carried out by a back-dropping butanone method, and after the reaction is finished, a hydrophilic solvent is added into the reaction again to realize that a product liquid is a homogeneous phase. The method breaks through the technical prejudice that butanone and a solvent are mixed firstly, an acidic catalyst is added, and hydrogen peroxide is added dropwise in the traditional synthetic method, and the method adopts the hydrogen peroxide as a base material and utilizes the acidity of the hydrogen peroxide to catalyze automatically.
Compared with the traditional method, the technical advantages of the invention are focused on the following aspects: 1. the reaction process is very stable, and the safety of the synthesis process is improved. 2. The synthesis process of the product does not generate three wastes, thereby solving the problem of three wastes and simultaneously removing the potential safety hazard caused by the instability of waste water. 3. The product has good service performance. 4. The product synthesized by the method has stability exceeding that of the similar products reported at present. In conclusion, the invention designs a brand new synthesis route, the product synthesized by the route effectively avoids the generation of three wastes on the premise of ensuring the application performance of the product, simultaneously, the stability of the product is greatly improved, and in the storage experiment of the product, the stability of the product synthesized by the process reaches the best level of similar products at home and abroad.
Detailed Description
Hereinafter, specific embodiments of the present invention will be described in detail. Well-known structures or functions may not be described in detail in the following embodiments in order to avoid unnecessarily obscuring the details. Approximating language, as used herein in the following examples, may be applied to identify quantitative representations that could permissibly vary in number without resulting in a change in the basic function. Unless defined otherwise, technical and scientific terms used in the following examples have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
Example 1
The method comprises the steps of sequentially adding 90g (1.323mol) of 50% hydrogen peroxide and 15.0g of 99.5% dimethyl phthalate into a 250ml four-neck bottle provided with a stirring device, a thermometer and a dropping funnel, starting stirring, controlling the temperature of a reaction system to be 20-22 ℃ through an external constant temperature water bath under the stirring condition, slowly dropwise adding 50.5g (0.700mol) of butanone into the system through the dropping funnel, keeping the dropwise adding time at about 2.0h, continuously stirring and reacting at the temperature for 1.0h after the dropwise adding is finished, after the reaction is finished, adding 45g of diethylene glycol and 0.004g of product stabilizer into the system under the stirring condition, continuously stirring for 10 min until the stabilizer is completely dissolved, obtaining 200g of a product and the active oxygen content is 9.81%.
Example 2
Adding 15.0g of 99.5% dimethyl phthalate and 50.5g (0.700mol) of butanone into a 250ml four-mouth bottle provided with a stirring device, a thermometer and a dropping funnel in sequence, starting stirring, dripping 0.3g of 60-65% nitric acid into the system under the stirring condition, controlling the temperature of the reaction system to be 20-22 ℃ through an external constant temperature water bath, slowly dripping 90g (1.323mol) of 50% hydrogen peroxide into the system through the dropping funnel, keeping the dripping time to be about 2.0h, continuing stirring and reacting at the temperature for 1.0h after finishing dripping, stopping stirring, keeping the temperature and standing for 0.5h, separating out about 33.0g of water, starting stirring again after water separation, adding 50.0g of ethylene glycol and 0.004g of product stabilizer into the system under the stirring condition, stirring for 10 min until the stabilizer is completely dissolved to obtain 172.8g of product, the active oxygen content was 9.82%.
Example 3
In a 250ml four-necked flask equipped with a stirrer, a thermometer and a dropping funnel, 15.0g of 99.5% dimethyl phthalate and 50.5g (0.700mol) of methyl ethyl ketone were sequentially charged, and after the charging, stirring was started, dripping 0.3g of 95-98% sulfuric acid under stirring, then controlling the temperature of a reaction system at 20-22 ℃ through an external constant-temperature water bath, slowly dripping 90g (1.323mol) of 50% hydrogen peroxide into the system through a dripping funnel, keeping the dripping time at about 2.0h, after the dripping is finished, continuously stirring and reacting at the temperature for 1.0h, then stopping stirring, keeping the temperature and standing for 0.5h until the system is clearly layered, separating water content of 37.0g, starting stirring again, under the condition of stirring, 54.0g of monoethylene glycol and 0.004g of product stabilizer are added into the system, and stirring is continued for 10 minutes until the stabilizer is completely dissolved, so that 172.3g of product with the active oxygen content of 9.82% is obtained.
Example 4
15.0g of 99.5% dimethyl phthalate and 50.5g (0.700mol) of butanone are sequentially added into a 250ml four-neck flask provided with a stirring device, a thermometer and a dropping funnel, stirring is started, 0.5g of 99% trichloroacetic acid is added under the stirring condition, then the temperature of a reaction system is controlled to be 20-22 ℃ through an external constant temperature water bath, 90g (1.323mol) of 50% hydrogen peroxide is slowly dropped into the system through the dropping funnel, the dropping time is maintained to be about 2.0 hours, after the dropping is finished, the stirring reaction is continuously carried out for 1.0 hour at the temperature, then the stirring is stopped, the temperature is kept and the standing is carried out for 0.5 hour, 27.0g of water is separated out, stirring is started again, 49.0g of a ketal and 0.004g of a product are added into the system under the stirring condition, the stirring is continued for 10 minutes, the stabilizer is completely dissolved, and 177.5g of the product is obtained, and the active oxygen content is 9.80%.
Example 5
The method comprises the steps of sequentially adding 90g (1.323mol) of 50% hydrogen peroxide and 15.0g of 99.5% dimethyl phthalate into a 250ml four-mouth bottle provided with a stirring device, a thermometer and a dropping funnel, starting stirring, controlling the temperature of a reaction system to be 20-22 ℃ through an external constant temperature water bath under the stirring condition, slowly dropwise adding 50.5g (0.700mol) of butanone into the system through the dropping funnel, keeping the dropwise adding time at about 2.0h, continuously stirring and reacting at the temperature for 1.0h after the dropwise adding is finished, adding 45g of ethylene glycol serving as a solvent and 0.004g of a product stabilizer into the system under the stirring condition after the reaction is finished, continuously stirring for 10 min until the stabilizer is completely dissolved, and discharging to obtain 200g of a product, wherein the active oxygen content is 9.82%.
Example 6
In a 250ml four-mouth bottle provided with a stirring device, a thermometer and a dropping funnel, 90g (1.323mol) of 50% hydrogen peroxide and 15.0g of 99.5% dimethyl phthalate are sequentially added, stirring is started after the addition is finished, the temperature of a reaction system is controlled to be 20-22 ℃ through an external constant temperature water bath under the stirring condition, then 50.5g (0.700mol) of butanone is slowly dripped into the system through the dropping funnel, the dripping time is maintained to be about 2.0h, after the dripping is finished, the stirring reaction is continuously carried out for 1.0h at the temperature, after the reaction is finished, 45g of glycerol and 0.004g of a product stabilizer are added into the system under the stirring condition, stirring is carried out for 10 min until the stabilizer is completely dissolved, 200g of the product is obtained, and the active oxygen content is 9.81%.
Example 7
Sequentially adding 90g (1.323mol) of 50% hydrogen peroxide and 15.0g of 99.5% dimethyl phthalate into a 250ml four-mouth bottle provided with a stirring device, a thermometer and a dropping funnel, starting stirring, cooling by an external ice water bath under the stirring condition, reducing the temperature of a reaction system to 0-5 ℃, slowly dropwise adding 50.5g (0.700mol) of butanone into the system by the dropping funnel, maintaining the dropwise adding time at about 2.0h, maintaining the temperature at not higher than 5 ℃, removing the constant temperature water bath after the dropwise adding is finished, gradually heating the reaction system to 30 ℃, maintaining the temperature of the system at 33-35 ℃ by the constant temperature water bath for 1.0h, after the reaction is finished, adding 45g of diethylene glycol and 0.004g of a product stabilizer into the system under the stirring condition, continuously stirring for 10 min till the stabilizer is completely dissolved to obtain 200g of the product, the active oxygen content was tested at 9.81%.
Example 8
Into a 250ml four-necked flask equipped with a stirrer, a thermometer and a dropping funnel were sequentially charged 90g (1.323mol) of 50% hydrogen peroxide and 15.0g of 99.5% dimethyl phthalate, and after the charging, stirring was started, under the condition of stirring, the temperature of a reaction system is controlled to be 30-32 ℃ through external constant temperature water bath, then slowly dripping 50.5g (0.700mol) butanone into the system through a dropping funnel, keeping the dripping time at about 2.0h, keeping the temperature at 30-35 ℃ during the dripping, after the dripping is finished, maintaining the temperature of the system at 33-35 ℃ by using a constant-temperature water bath, preserving the temperature and reacting for 1.0h, after the reaction is finished, under the condition of stirring, adding 45g of monoethylene glycol and 0.004g of product stabilizer into the system, continuing stirring for 10 minutes until the stabilizer is completely dissolved, stopping stirring, discharging to obtain 200g of product, and testing the active oxygen content of the product to be 9.80%.
Example 9
100g (1.471mol) of 50% hydrogen peroxide and 15.0g of 99.5% dimethyl phthalate are sequentially added into a 250ml four-mouth bottle provided with a stirring device, a thermometer and a dropping funnel, stirring is started after the addition, the temperature of a reaction system is controlled to be 20-22 ℃ through an external constant temperature water bath under the stirring condition, then 50.5g (0.700mol) of butanone is slowly dropped into the system through the dropping funnel, the dropping time is maintained to be about 2.0h, after the dropping is finished, the temperature of the system is maintained to be 20-22 ℃ through the constant temperature water bath, the heat preservation and the heat preservation reaction is carried out for 1.0h, after the reaction is finished, 35g of diethylene glycol and 0.004g of a product stabilizer are added into the system under the stirring condition, stirring is continued for 10 min until the stabilizer is completely dissolved, and 200g of the product is obtained, and the active oxygen content is 11.01%.
Example 10
80g (1.176mol) of 50% hydrogen peroxide and 15.0g of 99.5% dimethyl phthalate are sequentially added into a 250ml four-mouth bottle provided with a stirring device, a thermometer and a dropping funnel, stirring is started after the addition, the temperature of a reaction system is controlled to be 20-22 ℃ through an external constant temperature water bath under the stirring condition, then 50.5g (0.700mol) of butanone is slowly dropped into the system through the dropping funnel, the dropping time is maintained to be about 2.0h, after the dropping is finished, the temperature of the system is maintained to be 20-22 ℃ through the constant temperature water bath, the heat preservation and the heat preservation reaction is carried out for 1.0h, after the reaction is finished, 55g of monoethylene glycol and 0.004g of a product stabilizer are added into the system under the stirring condition, stirring is continued for 10 min, and the stabilizer is completely dissolved, so that 200g of the product is obtained, and the active oxygen content is 9.103%.
Example 11
This example was conducted to examine the amount of wastewater produced, the product stability and the product performance in examples 1 to 10.
TABLE 1 production of wastewater per ton of product under different catalytic conditions
TABLE 2 stability of the products produced under the respective conditions
The performance indexes of the products obtained in the embodiments are detected through an experimental method as follows: the resin used in the experiment is 196 resin produced by Shandong Hongtong chemical engineering Co., Ltd, the accelerant is Gaoji No. 1 produced by the applicant, the temperature recorder is an R1001 temperature recorder produced by Hangzhou American control automation technology Co., Ltd, and the ambient temperature is 25 ℃. The experimental results are shown in table 3 below.
TABLE 3 product Performance index
The experimental data show that the process can realize no three-waste discharge and achieve the aim of purification production. Moreover, the product is synthesized by the reaction under the self-acid catalysis of hydrogen peroxide, and because no other ions are introduced, the stability of the product can achieve a very ideal result. Meanwhile, when 196 resin is initiated, the exothermic quantity of the product synthesized by hydrogen peroxide autocatalysis is obviously higher than that of the product synthesized by using other acidic catalysts.
The embodiments of the present invention have been described in detail, but the description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention. Any modification, equivalent replacement, and improvement made within the scope of the application of the present invention should be included in the protection scope of the present invention.
Claims (4)
1. A synthesis method of methyl ethyl ketone peroxide without three wastes is characterized by comprising the following steps: adding hydrogen peroxide and dimethyl phthalate in a formula amount into a container, and continuously dropwise adding butanone into the container under the stirring condition until the reaction is finished;
in the dropwise adding process, the system temperature is 0-40 ℃;
the molar ratio of the consumption of the hydrogen peroxide to the consumption of the butanone is 1.6-2.1: 1;
the duration time of the dropwise adding is 0.5-3 h;
after the reaction is finished, adding a hydrophilic solvent and a product stabilizer into the reaction system, and stirring until the product stabilizer is dissolved;
the hydrophilic solvent is glycol, monoethylene glycol or glycerol.
2. The method for synthesizing methyl ethyl ketone peroxide without three wastes according to claim 1, wherein the temperature of the system is 20-40 ℃ in the dropping process.
3. The synthesis method of methyl ethyl ketone peroxide without three wastes according to claim 1, characterized in that the molar ratio of the consumption of hydrogen peroxide to the consumption of butanone is 1.8-1.9: 1.
4. The method for synthesizing methyl ethyl ketone peroxide without three wastes as claimed in claim 1, wherein the duration of the dropping is 1.5-2.5 h.
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| DE4438147A1 (en) * | 1994-10-25 | 1996-05-02 | Peroxid Chemie Gmbh | Production of salt-free and low-water methyl ethyl ketone peroxide |
| CN1800161B (en) * | 2006-01-16 | 2010-11-10 | 华东理工大学 | Method and microreaction device for continuous producing garox mek |
| CN105237453B (en) * | 2015-09-25 | 2017-09-19 | 西北师范大学 | Make the method for catalyst preparation methyl ethyl ketone peroxide using acid-exchange resin |
| CN107999011B (en) * | 2017-12-13 | 2019-03-08 | 方亨 | Methyl ethyl ketone peroxide production system and production technology |
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