CN113307755A - Purification method of 1, 1-bis (tert-butyl peroxy) cyclohexane - Google Patents
Purification method of 1, 1-bis (tert-butyl peroxy) cyclohexane Download PDFInfo
- Publication number
- CN113307755A CN113307755A CN202110679367.0A CN202110679367A CN113307755A CN 113307755 A CN113307755 A CN 113307755A CN 202110679367 A CN202110679367 A CN 202110679367A CN 113307755 A CN113307755 A CN 113307755A
- Authority
- CN
- China
- Prior art keywords
- bis
- cyclohexane
- tert
- butylperoxy
- purification
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a method for purifying 1, 1-bis (tert-butyl peroxy) cyclohexane, belonging to the technical field of separation and purification. The method comprises the steps of mixing a 1, 1-bis (tert-butyl peroxy) cyclohexane crude product with a purification solution, and carrying out oxidation-reduction reaction to obtain an oxidation reaction product, wherein the purification solution is a mixed aqueous solution of strong base and hydrogen peroxide. In the invention, cyclohexanone in the 1, 1-bis (tert-butyl peroxy) cyclohexane crude product reacts with hydrogen peroxide to generate oxidation reduction reaction to generate adipic acid, and the adipic acid enters a water phase and is separated from 1, 1-bis (tert-butyl peroxy) cyclohexane in an oil phase; the method can remove water-soluble impurities in the oil layer by washing and drying the oil layer to obtain the pure 1, 1-bis (tert-butylperoxy) cyclohexane. The purification method provided by the invention can effectively remove cyclohexanone, is safe to operate, and is low in cost of sodium hydroxide and hydrogen peroxide, green and pollution-free.
Description
Technical Field
The invention relates to the technical field of separation and purification, and particularly relates to a purification method of 1, 1-bis (tert-butylperoxy) cyclohexane.
Background
1, 1-bis (tert-butyl peroxy) cyclohexane (CH for short) is a common ketal organic peroxide, is a low-volatility yellowish transparent liquid, is mainly used as a polymerization initiator of styrene and comonomers thereof, and is used as a crosslinking agent of polyvinyl chloride, polyethylene, polystyrene and unsaturated polyester, and a vulcanizing agent of silicone rubber.
Currently, the most common method in industrial production is to prepare 1, 1-bis (t-butylperoxy) cyclohexane by catalytic oxidation of cyclohexanone with sulfuric acid or other acid as a catalyst and t-butyl hydroperoxide as an oxidant, which is generally called acid-catalyzed synthesis. Chinese patent CN102863369A discloses a method for preparing 1, 1-bis (tert-butylperoxy) cyclohexane, wherein the post-treatment of the crude 1, 1-bis (tert-butylperoxy) cyclohexane is washing with liquid alkali to remove tert-butyl hydroperoxide as an impurity. However, about 0.5 to 1 wt% of cyclohexanone still remains in the 1, 1-bis (tert-butylperoxy) cyclohexane obtained by the method, which affects the purity of the 1, 1-bis (tert-butylperoxy) cyclohexane product, and the purity is only 95.5 to 96.5%.
Disclosure of Invention
In view of the above, the present invention aims to provide a method for purifying 1, 1-bis (tert-butylperoxy) cyclohexane. The method provided by the invention can effectively remove cyclohexanone in the 1, 1-bis (tert-butyl peroxy) cyclohexane crude product, and improve the purity of the 1, 1-bis (tert-butyl peroxy) cyclohexane product.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a method for purifying 1, 1-bis (tert-butylperoxy) cyclohexane, which comprises the following steps:
mixing the 1, 1-bis (tert-butyl peroxy) cyclohexane crude product with the purification solution, and carrying out oxidation-reduction reaction to obtain an oxidation reaction product; the 1, 1-bis (tert-butyl peroxy) cyclohexane crude product comprises cyclohexanone, and the purification liquid is a mixed aqueous solution of strong base and hydrogen peroxide;
layering the oxidation reaction product, and separating to obtain an oil layer and a water layer, wherein the oil layer contains 1, 1-bis (tert-butylperoxy) cyclohexane, and the water layer contains adipic acid;
and washing and drying the oil layer to obtain a pure product of the 1, 1-bis (tert-butylperoxy) cyclohexane.
Preferably, the strong base is an alkali metal hydroxide.
Preferably, the concentration of the strong base in the purification liquid is 0.2-1 wt%, and the concentration of the hydrogen peroxide is 1-5 wt%.
Preferably, the mass ratio of the crude 1, 1-bis (tert-butylperoxy) cyclohexane to the strong base and the hydrogen peroxide in the purification liquid is 1: (0.001-0.01): (0.005-0.05).
Preferably, the temperature of the oxidation-reduction reaction is 10-25 ℃ and the time is 3-5 h.
Preferably, the layering is standing layering, and the standing layering time is 30-90 min.
Preferably, before mixing the crude 1, 1-bis (tert-butylperoxy) cyclohexane with the purification solution, alkali washing is further carried out on the crude 1, 1-bis (tert-butylperoxy) cyclohexane.
Preferably, the alkali liquor for alkali washing is a sodium hydroxide solution, and the concentration of the sodium hydroxide solution is 4-7 wt%.
Preferably, the content of cyclohexanone in the crude 1, 1-bis (tert-butylperoxy) cyclohexane is 0.5-2 wt%.
Preferably, the purity of the pure 1, 1-bis (tert-butylperoxy) cyclohexane is more than or equal to 97 percent.
The invention provides a method for purifying 1, 1-bis (tert-butyl peroxy) cyclohexane, which comprises the steps of mixing a crude product of 1, 1-bis (tert-butyl peroxy) cyclohexane with a purification solution, and carrying out an oxidation-reduction reaction to obtain an oxidation reaction product, wherein the purification solution is a mixed aqueous solution of strong base and hydrogen peroxide. In the invention, under alkaline conditions, cyclohexanone in the 1, 1-bis (tert-butyl peroxy) cyclohexane crude product reacts with hydrogen peroxide to generate oxidation reduction reaction to generate adipic acid, and the adipic acid enters a water phase and is separated from the 1, 1-bis (tert-butyl peroxy) cyclohexane in an oil phase; the method can remove water-soluble impurities (such as tert-butyl hydroperoxide, liquid caustic soda, hydrogen peroxide, disodium adipate and the like) in the oil layer by washing and drying the oil layer to obtain the pure 1, 1-bis (tert-butylperoxy) cyclohexane. The purification method provided by the invention can effectively remove cyclohexanone, is safe to operate, and the used purification liquid is low in cost, green and pollution-free. The results of the examples show that the purity of the 1, 1-bis (tert-butylperoxy) cyclohexane product obtained by the purification method is more than or equal to 97 percent, and the residual quantity of cyclohexanone in the product is less than or equal to 0.1 percent.
Detailed Description
The invention provides a method for purifying 1, 1-bis (tert-butylperoxy) cyclohexane, which comprises the following steps:
mixing the 1, 1-bis (tert-butyl peroxy) cyclohexane crude product with the purification solution, and carrying out oxidation-reduction reaction to obtain an oxidation reaction product; the 1, 1-bis (tert-butyl peroxy) cyclohexane crude product comprises cyclohexanone, and the purification liquid is a mixed aqueous solution of strong base and hydrogen peroxide;
layering the oxidation reaction product, and separating to obtain an oil layer and a water layer, wherein the oil layer contains 1, 1-bis (tert-butylperoxy) cyclohexane, and the water layer contains adipic acid;
and washing and drying the oil layer to obtain a pure product of the 1, 1-bis (tert-butylperoxy) cyclohexane.
The invention mixes the 1, 1-bis (tert-butyl peroxy) cyclohexane crude product with the purification liquid to carry out oxidation-reduction reaction, and obtains an oxidation reaction product. In the invention, the 1, 1-bis (tert-butyl peroxy) cyclohexane crude product is preferably a 1, 1-bis (tert-butyl peroxy) cyclohexane crude product prepared by an acid catalysis synthesis method, the 1, 1-bis (tert-butyl peroxy) cyclohexane crude product comprises cyclohexanone, and the content of the cyclohexanone is preferably 0.5-2 wt%, and more preferably 1-1.5 wt%.
The present invention also preferably comprises subjecting the crude 1, 1-bis (t-butylperoxy) cyclohexane to an alkaline wash prior to mixing the crude 1, 1-bis (t-butylperoxy) cyclohexane with the purification solution. In the invention, the alkali washing alkaline solution is preferably a sodium hydroxide solution, and the concentration of the sodium hydroxide solution is preferably 4-7 wt%, and more preferably 5-6 wt%. The invention has no special requirements on the specific operation mode of the alkali washing, and the washing mode which is well known to the technical personnel in the field can be used. According to the invention, the oxidizing agent tert-butyl hydroperoxide in the 1, 1-bis (tert-butyl peroxy) cyclohexane crude product can be removed through the alkali washing.
In the invention, the crude product of the 1, 1-bis (tert-butyl peroxy) cyclohexane comprises cyclohexanone, and the purification solution is a mixed aqueous solution of strong base and hydrogen peroxide. In the present invention, the strong base is preferably an alkali metal hydroxide, more preferably sodium hydroxide and/or potassium hydroxide. In the invention, the concentration of the strong base in the purification solution is preferably 0.2 to 1 wt%, more preferably 0.4 to 0.8 wt%, and further preferably 0.5 to 0.6 wt%; the concentration of the hydrogen peroxide is preferably 1 to 5 wt%, more preferably 2 to 4 wt%, and further preferably 3 wt%. In the invention, the pH value of the purification liquid is preferably not less than 12, and more preferably 12-13.
The preparation method of the purification liquid has no special requirement, and the purification liquid is prepared by mixing strong base, hydrogen peroxide and water in proportion. In the present invention, the sodium hydroxide is preferably added in the form of liquid sodium hydroxide, i.e., liquid alkali.
The invention mixes the 1, 1-bis (tert-butyl peroxy) cyclohexane crude product with the purification liquid to carry out oxidation-reduction reaction, and obtains an oxidation reaction product. The invention does not require any particular mixing means, such as stirring, known to the person skilled in the art. In the present invention, the mass ratio of the crude 1, 1-bis (tert-butylperoxy) cyclohexane to the strong base and hydrogen peroxide is preferably 1: (0.001-0.01): (0.005-0.05), more preferably 1: (0.003-0.008): (0.02-0.04). In the invention, when the concentration of the strong base in the purification liquid is 0.2-1 wt% and the concentration of the hydrogen peroxide is 1-5 wt%, the mass ratio of the crude 1, 1-bis (tert-butylperoxy) cyclohexane to the purification liquid is preferably 1-2: 1, more preferably 1.2-1.8: 1, and further preferably 1.5-1.6: 1.
in the invention, the temperature of the oxidation-reduction reaction is preferably 10-25 ℃, and more preferably 15-20 ℃; the time is preferably 3 to 5 hours, and more preferably 4 hours. In the invention, under alkaline conditions, cyclohexanone in the crude product of 1, 1-bis (tert-butyl peroxy) cyclohexane and hydrogen peroxide react to generate adipic acid through oxidation-reduction reaction.
After the oxidation-reduction reaction is completed, the oxidation reaction product is stood, an oil layer and a water layer are separated, and the obtained oil layer contains 1, 1-bis (tert-butylperoxy) cyclohexane. In the invention, the standing is preferably performed at room temperature, and the standing time is preferably 30-90 min, and more preferably 40-70 min.
The present invention does not require any particular means for separating the oil and water layers, and may employ separation means well known to those skilled in the art.
After the oil layer is obtained, the oil layer is preferably subjected to post-treatment in the invention, and the post-treatment mode preferably comprises the following steps:
and washing and drying the obtained oil layer sequentially to obtain a pure product of the 1, 1-bis (tert-butylperoxy) cyclohexane.
In the present invention, the water for washing is preferably process water, and the drying agent is preferably anhydrous sodium sulfate or anhydrous magnesium sulfate. In the present invention, after the oil layer is dried using a drying agent, it is also preferable to separate the drying agent in the oil layer by performing solid-liquid separation on the oil layer.
The purity of the 1, 1-bis (tert-butylperoxy) cyclohexane product obtained by the purification method provided by the invention is more than or equal to 97%, and the residual amount of cyclohexanone in the product is less than or equal to 0.1%.
The following examples are provided to illustrate the purification method of 1, 1-bis (t-butylperoxy) cyclohexane provided by the present invention in detail, but they should not be construed as limiting the scope of the present invention.
Example 1
The crude product of 1, 1-bis (tert-butylperoxy) cyclohexane is synthesized by the method of Chinese patent CN102863369A, and the purity and cyclohexanone content of 1-bis (tert-butylperoxy) cyclohexane are analyzed by GC detection.
The purity of the obtained 1, 1-bis (tert-butyl peroxy) cyclohexane is 90.6 percent and the content of cyclohexanone is 1.61 percent.
Putting 540kg of 1, 1-bis (tert-butylperoxy) cyclohexane synthetic crude product into a 1000L reaction kettle, starting the reaction kettle to stir, controlling the temperature in the kettle to be 15-25 ℃, putting 270kg of 5 wt% sodium hydroxide solution into the reaction kettle, keeping the temperature and stirring for 30min, standing for layering, and removing a water layer to obtain a first oil layer.
Putting the first oil layer into a 1000L reaction kettle, starting the reaction kettle to stir, controlling the temperature in the kettle to be 25 ℃, and putting 270kg of purification liquid into the reaction kettle, wherein the content of sodium hydroxide in the extracting solution is 0.5 wt%, and the content of hydrogen peroxide is 2.1 wt%; carrying out oxidation-reduction reaction for 3h under the stirring condition, then standing for 30min, and layering to obtain a second oil layer;
and continuously putting the second oil layer into a 1000L reaction kettle, starting the reaction kettle to stir, adding 270kg of process water, stirring for 30min, standing for layering, separating out a water layer, adding anhydrous sodium sulfate, stirring for 30min, and performing suction filtration and solid-liquid separation to obtain a pure 1, 1-bis (tert-butylperoxy) cyclohexane product.
The purity of the obtained 1, 1-bis (t-butylperoxy) cyclohexane was 97.11% by GC assay, with a cyclohexanone content of 0.07 wt%.
Example 2
The crude product of 1, 1-bis (tert-butylperoxy) cyclohexane is synthesized by the method of Chinese patent CN102863369A, and the purity and cyclohexanone content of 1-bis (tert-butylperoxy) cyclohexane are analyzed by GC detection.
Through detection, the purity of the obtained 1, 1-bis (tert-butyl peroxy) cyclohexane is 90.2%, and the content of cyclohexanone is 1.71%.
Adding 500kg of 1, 1-bis (tert-butylperoxy) cyclohexane into a 1000L reaction kettle to synthesize a crude product, starting the reaction kettle to stir, controlling the temperature in the kettle to be 15-25 ℃, adding 270kg of 6 wt% sodium hydroxide solution, keeping the temperature and stirring for 30min, standing for layering, and removing a water layer to obtain a first oil layer.
Putting the first oil layer into a 1000L reaction kettle, starting the reaction kettle to stir, controlling the temperature in the kettle to be 25 ℃, and putting 270kg of purification liquid into the reaction kettle, wherein the content of potassium hydroxide in the extracting solution is 0.3 wt%, and the content of hydrogen peroxide is 1.5 wt%; carrying out oxidation-reduction reaction for 4h under the stirring condition, then standing for 50min, and layering to obtain a second oil layer;
and continuously putting the second oil layer into a 1000L reaction kettle, starting the reaction kettle to stir, adding 270kg of process water into the reaction kettle, stirring for 30min, standing for layering, separating out a water layer, adding anhydrous magnesium sulfate into the water layer, stirring for 30min, and performing suction filtration and solid-liquid separation to obtain a pure 1, 1-bis (tert-butylperoxy) cyclohexane product.
The purity of the obtained 1, 1-bis (t-butylperoxy) cyclohexane was 97.31% by GC assay, wherein the cyclohexanone content was 0.05 wt%.
Example 3
The crude product of 1, 1-bis (tert-butylperoxy) cyclohexane is synthesized by the method of Chinese patent CN102863369A, and the purity and cyclohexanone content of 1-bis (tert-butylperoxy) cyclohexane are analyzed by GC detection.
The purity of the obtained 1, 1-bis (tert-butyl peroxy) cyclohexane is 91.1% and the content of cyclohexanone is 1.33%.
Adding 270kg of 1, 1-bis (tert-butylperoxy) cyclohexane into a 1000L reaction kettle to synthesize a crude product, starting the reaction kettle to stir, controlling the temperature in the kettle to be 15-25 ℃, adding 270kg of 6.5 wt% sodium hydroxide solution, keeping the temperature and stirring for 30min, standing for layering, and removing a water layer to obtain a first oil layer.
Putting the first oil layer into a 1000L reaction kettle, starting the reaction kettle to stir, controlling the temperature in the kettle to be 15 ℃, and putting 270kg of purification liquid into the reaction kettle, wherein the content of sodium hydroxide in the extracting solution is 1 wt%, and the content of hydrogen peroxide is 4 wt%; carrying out oxidation-reduction reaction for 5h under the stirring condition, then standing for 90min, and layering to obtain a second oil layer;
and continuously putting the second oil layer into a 1000L reaction kettle, starting the reaction kettle to stir, adding 270kg of process water into the reaction kettle, stirring for 30min, standing for layering, separating out a water layer, adding anhydrous magnesium sulfate into the water layer, stirring for 30min, and performing suction filtration and solid-liquid separation to obtain a pure 1, 1-bis (tert-butylperoxy) cyclohexane product.
The purity of the obtained 1, 1-bis (t-butylperoxy) cyclohexane was 98.36% by GC assay, wherein the cyclohexanone content was 0.02% by weight.
Comparative example 1
Comparative example 1 differs from example 1 in that the extract contained no sodium hydroxide, the same procedure was followed, and the test results showed that 1, 1-bis (t-butylperoxy) cyclohexane was obtained with a purity of 95.8% and a cyclohexanone content of 0.72% by weight.
Comparative example 2
Comparative example 2 differs from example 1 in that the alkali in the extract was ammonia water, and the rest of the operations were the same, and the test results showed that the purity of the obtained 1, 1-bis (t-butylperoxy) cyclohexane was 95.1% and the cyclohexanone content was 1.1% by weight.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (10)
1. A method for purifying 1, 1-bis (tert-butylperoxy) cyclohexane comprises the following steps:
mixing the 1, 1-bis (tert-butyl peroxy) cyclohexane crude product with the purification solution, and carrying out oxidation-reduction reaction to obtain an oxidation reaction product; the 1, 1-bis (tert-butyl peroxy) cyclohexane crude product comprises cyclohexanone, and the purification liquid is a mixed aqueous solution of strong base and hydrogen peroxide;
layering the oxidation reaction product, and separating to obtain an oil layer and a water layer, wherein the oil layer contains 1, 1-bis (tert-butylperoxy) cyclohexane, and the water layer contains adipic acid;
and washing and drying the oil layer to obtain a pure product of the 1, 1-bis (tert-butylperoxy) cyclohexane.
2. The purification method according to claim 1, wherein the strong base is an alkali metal hydroxide.
3. The purification method according to claim 1 or 2, wherein the concentration of the strong base in the purification solution is 0.2 to 1 wt%, and the concentration of the hydrogen peroxide is 1 to 5 wt%.
4. The purification method according to claim 1 or 3, wherein the mass ratio of the crude 1, 1-bis (tert-butylperoxy) cyclohexane to the strong base and the hydrogen peroxide in the purification solution is 1: (0.001-0.01): (0.005-0.05).
5. The purification method according to claim 1, wherein the temperature of the redox reaction is 10 to 25 ℃ and the time is 3 to 5 hours.
6. The purification method according to claim 1, wherein the layering is static layering, and the time for static layering is 30-90 min.
7. The purification method as claimed in claim 1, further comprising subjecting the crude 1, 1-bis (t-butylperoxy) cyclohexane to alkali washing before mixing the crude 1, 1-bis (t-butylperoxy) cyclohexane with the purification solution.
8. The purification method according to claim 7, wherein the alkali washing lye is a sodium hydroxide solution, and the concentration of the sodium hydroxide solution is 4-7 wt%.
9. The purification method as claimed in claim 1, wherein the content of cyclohexanone in the crude 1, 1-bis (tert-butylperoxy) cyclohexane is 0.5-2 wt%.
10. The purification method according to claim 1, wherein the purity of the purified 1, 1-bis (t-butylperoxy) cyclohexane is not less than 97%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110679367.0A CN113307755A (en) | 2021-06-18 | 2021-06-18 | Purification method of 1, 1-bis (tert-butyl peroxy) cyclohexane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110679367.0A CN113307755A (en) | 2021-06-18 | 2021-06-18 | Purification method of 1, 1-bis (tert-butyl peroxy) cyclohexane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113307755A true CN113307755A (en) | 2021-08-27 |
Family
ID=77379347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110679367.0A Pending CN113307755A (en) | 2021-06-18 | 2021-06-18 | Purification method of 1, 1-bis (tert-butyl peroxy) cyclohexane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113307755A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3935278A (en) * | 1970-03-04 | 1976-01-27 | Atlantic Richfield Company | Process for preparing diperoxide from an organic hydro-peroxide and a ketone |
| US4052464A (en) * | 1975-07-21 | 1977-10-04 | The Dow Chemical Company | Process for the manufacture of di-t-butylperoxy ketals |
| CN101479239A (en) * | 2006-04-27 | 2009-07-08 | 阿克马法国公司 | Process for synthesizing selected organic peroxides |
-
2021
- 2021-06-18 CN CN202110679367.0A patent/CN113307755A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3935278A (en) * | 1970-03-04 | 1976-01-27 | Atlantic Richfield Company | Process for preparing diperoxide from an organic hydro-peroxide and a ketone |
| US4052464A (en) * | 1975-07-21 | 1977-10-04 | The Dow Chemical Company | Process for the manufacture of di-t-butylperoxy ketals |
| CN101479239A (en) * | 2006-04-27 | 2009-07-08 | 阿克马法国公司 | Process for synthesizing selected organic peroxides |
Non-Patent Citations (1)
| Title |
|---|
| 张福莲，等: "催化氧化环己酮合成己二酸研究进展", 《广东化工》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2821384B1 (en) | Production process for preparing cyclohexanol and cyclohexanone by cyclohexane oxidation | |
| CN108570021B (en) | Vulcanization accelerator CBS and continuous production method thereof | |
| WO2023056740A1 (en) | Production process for rubber vulcanization accelerator mbts | |
| JPH0615484B2 (en) | Process for producing cyclohexanol and cyclohexanone | |
| CN115557927A (en) | Preparation method of vinyl sulfate | |
| CN102311420B (en) | Method for synthesizing epsilon-caprolactone | |
| CN113307755A (en) | Purification method of 1, 1-bis (tert-butyl peroxy) cyclohexane | |
| CN111825590A (en) | Preparation method of tert-butyl peroxybenzoate | |
| CN110981778B (en) | Preparation method of cumyl peroxyneodecanoate and solvent-based CNP | |
| CN112079753A (en) | Production process of p-toluenesulfonamide urea | |
| CN110128258B (en) | Synthetic method of sitagliptin intermediate 2,4, 5-trifluorophenylacetic acid | |
| CN101899020A (en) | DZ synthesized by mixing mother solution | |
| JP3492052B2 (en) | Process for producing dihydroxybenzene and diisopropylbenzene dicarbinol | |
| US2889368A (en) | Process for the acid decomposition of | |
| CN113582944B (en) | Production process of accelerant DCBS | |
| CN106749108B (en) | A method of preparing perfluor -2,3- epoxy -2- methylpentane | |
| CN108610322B (en) | Preparation method of R-glyceraldehyde acetonide | |
| CN111269196A (en) | Method for preparing NS by UHP oxidation | |
| CN115286593B (en) | Preparation method of dibenzothiazyl disulfide serving as rubber vulcanization accelerator | |
| CN113735737B (en) | Preparation method of p-benzoquinone dioxime | |
| CN116178234B (en) | Preparation method of solvent type peroxy-2-ethylhexyl tert-butyl carbonate | |
| CN115521237B (en) | Method for preparing tert-butyl peroxybenzoate in high yield | |
| CN112679320A (en) | Process for preparing resorcinol and hydroquinone | |
| CN109232347A (en) | A kind of recoverying and utilizing method of 1,1- bis(t-butylperoxy) -3,3,5- trimethyl-cyclohexane soda-wash water | |
| US4036890A (en) | Preparation of organic hydroperoxides |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |