CN115583905A - Preparation method of m-di-tert-butylperoxydiisopropylbenzene - Google Patents
Preparation method of m-di-tert-butylperoxydiisopropylbenzene Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 53
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
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- 239000002994 raw material Substances 0.000 claims abstract description 12
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
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- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 16
- 238000009833 condensation Methods 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 230000005494 condensation Effects 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 claims description 7
- 229910001488 sodium perchlorate Inorganic materials 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 238000004090 dissolution Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 3
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- 238000001914 filtration Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
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- 238000004321 preservation Methods 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 8
- 238000007086 side reaction Methods 0.000 abstract description 8
- 238000006482 condensation reaction Methods 0.000 abstract description 6
- AXWJKQDGIVWVEW-UHFFFAOYSA-N 2-(dimethylamino)butanedioic acid Chemical compound CN(C)C(C(O)=O)CC(O)=O AXWJKQDGIVWVEW-UHFFFAOYSA-N 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 4
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- 239000000243 solution Substances 0.000 description 25
- 230000000694 effects Effects 0.000 description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- JGDSPOCXKKSJTF-UHFFFAOYSA-N C(C)(C)(C)OOC1=CC(=C(C=C1C(C)C)C(C)C)OOC(C)(C)C Chemical compound C(C)(C)(C)OOC1=CC(=C(C=C1C(C)C)C(C)C)OOC(C)(C)C JGDSPOCXKKSJTF-UHFFFAOYSA-N 0.000 description 2
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- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 1
- UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 description 1
- UGPWRRVOLLMHSC-UHFFFAOYSA-N 2-[3-(2-hydroxypropan-2-yl)phenyl]propan-2-ol Chemical compound CC(C)(O)C1=CC=CC(C(C)(C)O)=C1 UGPWRRVOLLMHSC-UHFFFAOYSA-N 0.000 description 1
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 1
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of m-di-tert-butylperoxy diisopropylbenzene, which is characterized in that mixed DC is taken as a raw material, dichloromethane is taken as a solvent, perchloric acid is taken as a catalyst, and the method comprises the following steps: dissolving raw materials, separating and crystallizing, condensing and feeding, removing a water layer, reacting and synthesizing, and performing post-treatment to obtain the m-di-tert-butylperoxydiisopropylbenzene. Compared with the prior art, the invention has the following beneficial effects: refining the raw materials before the condensation reaction to obtain high-purity meta-DC; the side reaction is less, the reaction is rapid and single, the yield is higher, the side reaction products are less, and the purity of the obtained final product is higher; the safety of the reaction is increased; improves the yield and the content of the bis (tert-butyl peroxyisopropyl) benzene product.
Description
Technical Field
The invention relates to the field of organic synthesis, and particularly relates to a preparation method of m-di-tert-butylperoxydiisopropylbenzene.
Technical Field
1,3-bis (tert-butylperoxy) diisopropylbenzene, also known as m-bis (tert-butylperoxy) diisopropylbenzene, is abbreviated as meta-BIPB. BIPB is widely applied to vulcanizing agents of nitrile rubber, ethylene propylene rubber, rubber and polyurethane, and can obviously improve the properties of heat resistance, wear resistance, oil resistance and the like of polymers (2002,18 (11): 25, author Cai Shuming, tan Yongsheng and Feng Yidong of novel tasteless cross-linking agent BIPB published in China rubber magazine). Because meta-BIPB is free from odor generated by using dicumyl peroxide (DCP) cross-linking agent in the using process and materials prepared from meta-BIPB, the meta-BIPB is also called as an odorless cross-linking agent and is an environment-friendly cross-linking agent, and the market demand of the meta-BIPB is increased along with the increasing environmental requirements; since BIPB contains two peroxy bonds, the active oxygen content is higher and the amount used is less.
Compared with mixed BIPB, the pure meta-BIPB has higher melting point and higher purity, does not contain acetophenone per se or hardly generates acetophenone in the use process, is suitable for applications with high environmental protection requirements, and has a more efficient crosslinking effect.
In the BIPB production process, the isomerized DC is used as a raw material, namely 1,3 (1,4, 1,2) -bis (2-hydroxy-2-propyl) benzene, and the isomerized DC has three structures of ortho-position DC, meta-position DC and para-position DC, so that three structures of ortho-position to meta-position BIPB can also appear in a final product. The ortho-position DC is obtained by oxidation reduction of ortho-position diisopropylbenzene, and the ortho-position DC is difficult to form due to the high molecular steric hindrance effect of the ortho-position diisopropylbenzene, can form a cyclic ether structure through self-condensation after oxidation, can be partially present in the DC, and is difficult to completely separate. The speed of forming para-BIPB by para-DC is faster than that of meta-DC, and the para-BIPB generated after the rapid reaction can continuously generate side reaction in a reaction system, so that the impurity content is increased, and the main component content is reduced; and the meta DC has mild reaction and few side reactions due to the meta-diisopropylbenzene, so that the main peak content of the meta DC can be greatly improved, and the content of the acetophenone can be well controlled.
The condensation synthesis of meta-BIPB is generally understood as 1,3-bis (2-hydroxy-2-propyl) benzene, i.e. a process for producing BIPB by condensation dehydration reaction of meta-DC and tert-butyl hydroperoxide (TBHB) under certain conditions (see 2010,35 (12): 9-12, research on oxidation process in production of bis- (tert-butylperoxyisopropyl) benzene, published in Shanghai chemical, section Han Wenhua).
The condensation synthesis of meta-BIPB is mainly a heterogeneous reaction which takes sulfuric acid solution as a reaction system and is reported at present (see 2008, 11 (1): 38-41. The synthesis research of a novel cross-linking agent bis-tert-butylperoxydicumyl peroxide published in the chemical world, author Ding Xiangdong). However, the condensation reaction is an equilibrium reaction, and a large amount of water is generated in the reaction, so that the sulfuric acid concentration in the sulfuric acid solution is low, the reaction is incomplete, unilateral peroxide is increased, side reactions such as DC dehydration and the like occur, the yield is low, and impurities are more, so the sulfuric acid solution is eliminated quickly.
The condensation synthesis of meta-BIPB is also a method which takes acid as a catalyst to carry out double bond addition on meta-tert-butyl hydroperoxide (TBHB) and di (isopropenyl) benzene, but the method has low yield and harsh conditions and is difficult to realize industrialization.
CN106588735B discloses a production method of bis (tert-butylperoxyisopropyl) benzene, which is to use di- (2-hydroxyisopropyl) benzene and tert-butyl hydrogen peroxide aqueous solution as raw materials, perchloric acid aqueous solution as a catalyst, and toluene as a solvent, and carry out a condensation dehydration reaction method under a negative pressure condition to prepare BIPB. The preparation method accelerates the reaction process, but has the defects of higher boiling point of the toluene, poor water separation effect and difficult solvent removal in the later period.
Disclosure of Invention
The invention aims to provide a preparation method of m-di-tert-butylperoxy diisopropylbenzene, which aims to solve the problems in the prior art.
In order to achieve the purpose of the invention, the technical scheme adopted by the invention is as follows: a preparation method of m-di-tert-butylperoxydiisopropylbenzene is characterized in that mixed DC is used as a raw material, dichloromethane is used as a solvent, perchloric acid is used as a catalyst, and the method comprises the following steps:
a preparation method of m-di-tert-butylperoxydiisopropylbenzene is characterized in that mixed DC is used as a raw material, dichloromethane is used as a solvent, perchloric acid is used as a catalyst, and the method comprises the following steps:
(1) Raw material dissolution: adding ethanol into the mixed DC, heating, and completely dissolving;
(2) Separation and crystallization: standing the solution obtained in the step 1 for cooling, filtering and collecting solids while the solution is hot after heat preservation to obtain high-purity meta-DC;
(3) Condensation charging: adding dichloromethane and sodium perchlorate into another container, stirring, adding a sulfuric acid solution, stirring, cooling the temperature in the container, and adding a tert-butyl hydroperoxide (TBHB) solution;
(4) Removing a water layer: standing the mixture obtained in the step (3) and removing a water layer;
(5) Reaction synthesis: adding the high-purity meta DC obtained in the step 2 into the mixed material obtained in the step 4, stirring, decompressing and refluxing, and adding cold water to stop the reaction when the color of the reaction is changed;
(6) And (3) post-treatment: and (4) washing the mixture synthesized by the reaction in the step (5) by using a sodium hydroxide solution, washing by using hot water, and distilling at low temperature under reduced pressure to remove the solvent to obtain the product.
Preferably, the mixed DC is a mixture of meta DC and para DC, the mass ratio of the mixed DC to ethanol in step 1 is 1:1-2, and the mass ratio of sodium perchlorate, dichloromethane, sulfuric acid solution, tert-butyl hydroperoxide (80% tbhb in water) in step 3 is 1: 3; the mass ratio of the sodium hydroxide solution in the step 6 to the composition obtained in the step 5 is 1:2.
Preferably, the temperature is raised to 55-60 ℃ in the step 1; standing the ethanol solution of the DC in the step 2, cooling to 32-38 ℃, and preserving heat for 10-20 minutes; the cooling temperature in the container in the step 3 is within 10 ℃; standing the mixed material in the step 4 for 15-25 minutes; in the step 5, the temperature of reduced pressure reflux is controlled to be 35-45 ℃, and the pressure is controlled to be-0.035-0.04 MPa; the time is controlled within 2-3.5 hours.
Preferably, 95% industrial ethanol is added in the step 1; adding a 70% sulfuric acid solution and an 80% tert-butyl hydroperoxide (TBHB) solution in the step 3; in step 6, the solution is washed with 10% sodium hydroxide solution.
Preferably, the content of meditopdc in the mixed DC in step 2 is 10 to 90%.
Because the activity of the meta DC is higher than that of the para DC, pure meta DC is needed in high-end materials, and in the prior art, the pure para DC cannot be extracted, and the meta DC must be mixed in the para DC, the invention is based on the technical background that the pure para DC cannot be extracted at present to extract high-purity meta DC to prepare the m-di-tert-butylperoxydiisopropylbenzene.
Because meta DC, para DC and impurities have larger solubility difference in ethanol, the invention selects ethanol with different parts by mass, selects different dissolving temperatures and standing cooling temperatures, uses the ethanol to heat and dissolve a DC mixture, cools and crystallizes after full dissolution, filters when hot, and separates the meta DC from the mixture in the dissolving and separating process to obtain the high-purity meta DC. More ethanol is added, the concentration of the DC is too dilute, the meta-DC is difficult to separate out, and the ethanol is too little, so that the meta-and para-DC can be directly separated out, and the aim of extracting the meta-DC cannot be achieved, therefore, the optimal extraction effect can be achieved by selecting the optimal proportion.
In the condensation reaction process, water is continuously generated, and the safety of the reaction system can be ensured due to the existence of the water in the reaction system because of the existence of sulfuric acid and sodium perchlorate; but the catalyst is easy to dissolve in water, the reaction is too slow due to high water content, byproducts are increased, dichloromethane is slightly soluble in water and can be mutually soluble with other solvents, an organic phase in a water phase can be effectively extracted, water generated in the reaction can be well removed through reduced pressure reflux, the influence of water in the condensation reaction can be weakened, the reaction process can be accelerated, and meanwhile, part of water in the system is kept, so that the sulfuric acid concentration in the system can be reduced, and the explosion risk is reduced; in the final solvent removal stage, methylene chloride is easy to distill off due to low boiling point; meanwhile, the dichloromethane is an incombustible solvent, so that the safety of the reaction is greatly improved. If the amount of the dichloromethane is too small, the reaction is too fast, and side reactions are increased, so that the optimal effect can be achieved by selecting a proper proportion.
According to the technical scheme of the invention, the obtained high-purity meta-DC is added with a sulfuric acid solution and a tert-butyl hydroperoxide (TBHB) solution by taking dichloromethane as a solvent and sodium perchlorate as a catalyst according to the following reaction formula:
since the reactants and the products of neutralization all contain peroxide, the temperature of the synthesis reaction in the step 5 is controlled not to exceed 40 ℃ in order to ensure the safety of the experiment and the reactivity.
Compared with the prior art, the invention has the following beneficial effects:
1. the raw materials are refined before the condensation reaction to obtain the high-purity meta-DC.
2. The side reaction is less, the reaction is rapid and single, the yield is higher, the side reaction products are less, and the purity of the obtained final product is higher.
3. Methylene dichloride is used as a condensation solvent, and has good dissolving capacity, so that the influence of water in condensation is weakened, the reaction process is accelerated, part of water is kept in a system, the concentration of sulfuric acid in the system is reduced, and the explosion risk is reduced; methylene chloride is a nonflammable solvent, and the safety of the reaction is greatly improved.
4. The dichloromethane is a solvent, is beneficial to the condensation reaction, has high reaction speed, short reaction time, good dehydration effect, less solvent loss, low boiling point of dichloromethane, easy volatilization and easy distillation removal, and is more beneficial to the improvement of the yield and the content of the bis (tert-butylperoxyisopropyl) benzene product.
5. The product obtained by the invention is pure meta-BIPB, and because the activity of the meta-BIPB is higher than that of para-BIPB, the cross-linking effect of the product is better than that of pure para-BIPB and mixed BIPB, the reaction rate is faster, the addition amount is lower, and the product can be used as a cross-linking agent of some processing environments relative to harsh materials, and is more favorable for market acceptance.
Drawings
In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the drawings used in the implementation of the present invention will be briefly described below, the drawings are only a part of representative chromatographic results in the stage experiment of the present invention, and for those skilled in the art, the remaining drawings can be obtained according to the embodiments listed in the present invention or other embodiments without creative efforts.
FIG. 1 shows the results of step 1 mixed DC chromatography;
FIG. 2 shows the results of high purity meta-DC chromatography obtained after the refining in step 2;
FIG. 3 shows the chromatography results of the meta BIPB obtained in step 6.
It can be seen in sequence from fig. 1,2, 3 of the drawings: according to the preparation method, a mixture of 59% of meta DC and 38% of para DC in figure 1 is refined into pure meta DC in figure 2, and then meta BIPB with 98% of single side and double side in figure 3 is synthesized.
Detailed Description
The following description of the present invention is provided to enable those skilled in the art to better understand the technical solutions in the embodiments of the present invention and to make the above objects, features and advantages of the present invention more comprehensible.
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual values, and between the individual values may be combined with each other to yield one or more new ranges of values, which ranges of values should be considered as specifically disclosed herein.
A preparation method of m-di-tert-butylperoxydiisopropylbenzene comprises the following steps:
(1) Raw material dissolution: adding 95% ethanol into the mixed DC, heating, and dissolving completely;
(2) Separation and crystallization: standing the solution obtained in the step 1 for cooling, preserving the temperature for 10-15 minutes, filtering while the solution is hot, and collecting solids to obtain high-purity meta-DC;
(3) Condensation charging: adding dichloromethane and sodium perchlorate into another container, stirring for 5-10 min, adding 70% sulfuric acid solution, stirring for 5-10 min, cooling the temperature in the container to be within 10 ℃, adding 80% tert-butyl hydroperoxide (TBHB) solution, and stirring for 10 min;
(4) Removing the water layer: standing the mixed material obtained in the step 3 for 20 minutes, and removing a lower water layer;
(5) Reaction synthesis: adding the high-purity meta-position DC obtained in the step 2 into the mixed material obtained in the step 4, stirring and decompressing at the temperature of 40 ℃ to-0.04 MPa, refluxing for 3 hours, and adding cold water to stop the reaction when the color of the reaction is changed;
(6) And (3) post-treatment: and (3) weighing the mixture synthesized by the reaction in the step (5), washing the mixture by using a 10% sodium hydroxide solution (such as 1000 g of the mixture and 500 g of the sodium hydroxide solution) with the mass percent of 50%, washing the mixture by using hot water for 2 times, and distilling the oil layer at low temperature under reduced pressure to remove the solvent to obtain the product.
And performing liquid phase detection on the oil phase system obtained after the reaction to obtain the content of meta-BIPB and the content of total peroxide.
The following table shows the mass of the materials added in each step of the specific examples, and the temperature of the materials is the temperature finally required to be reached by the reaction in each example:
the foregoing examples are merely illustrative of some embodiments of the present invention, and the scope of the invention is not limited thereto, as the various aspects and embodiments of the invention disclosed herein are merely illustrative of specific ways to make and use the invention. Neither the front and rear sequence of the embodiments nor the specific operation thereof should limit the present invention, and any modifications and variations which can be easily conceived by those skilled in the art within the technical scope of the present invention are included in the protection scope of the present invention.
Claims (5)
1. A preparation method of m-di-tert-butylperoxydiisopropylbenzene is characterized in that mixed DC is used as a raw material, dichloromethane is used as a solvent, perchloric acid is used as a catalyst, and the method comprises the following steps:
(1) Raw material dissolution: adding ethanol into the mixed DC, heating, and dissolving completely;
(2) Separation and crystallization: standing the solution obtained in the step 1 for cooling, filtering and collecting solids while the solution is hot after heat preservation to obtain high-purity meta-DC;
(3) Condensation charging: adding dichloromethane and sodium perchlorate into another container, stirring, adding a sulfuric acid solution, stirring, cooling the temperature in the container, and adding a tert-butyl hydroperoxide (TBHB) solution;
(4) Removing the water layer: standing the mixture obtained in the step (3) and removing a water layer;
(5) Reaction synthesis: adding the high-purity meta DC obtained in the step 2 into the mixed material obtained in the step 4, stirring, decompressing and refluxing, and adding cold water to stop the reaction when the color of the reaction is changed;
(6) And (3) post-treatment: and (3) washing the mixture synthesized by the reaction in the step (5) with a sodium hydroxide solution, washing with hot water, and distilling at low temperature under reduced pressure to remove the solvent to obtain the product.
2. The method for preparing m-di-tert-butylperoxydiisopropylbenzene as claimed in claim 1, wherein the mixed DC is a mixture of m-DC and p-DC, the mass ratio of the mixed DC to ethanol in step 1 is 1:1-2, and the mass ratio of sodium perchlorate, dichloromethane, sulfuric acid solution and m-tert-butyl hydroperoxide (TBHB) solution in step 3 is 1: 3; the mass ratio of the sodium hydroxide solution in the step 6 to the composition obtained in the step 5 is 1:2.
3. The method for preparing m-di-tert-butylperoxydiisopropylbenzene as claimed in claim 1, wherein the temperature in step 1 is raised to 55-60 ℃; standing the ethanol solution of the DC in the step 2, cooling to 32-38 ℃, and preserving heat for 10-20 minutes; the cooling temperature in the container in the step 3 is within 10 ℃; standing the mixed material in the step 4 for 15-25 minutes; in the step 5, the temperature of the reduced pressure reflux is controlled to be 35-45 ℃, and the pressure is controlled to be-0.035-0.04 MPa; the time is controlled within 2-3.5 hours.
4. The method for preparing m-di-tert-butylperoxydiisopropylbenzene as claimed in claim 1, wherein 95% industrial ethanol is added in the step 1; adding a 70% sulfuric acid solution and an 80% tert-butyl hydroperoxide (TBHB) solution in the step 3; in step 6, the mixture is washed with 10% sodium hydroxide solution.
5. The method for preparing m-di-tert-butylperoxydiisopropylbenzene as claimed in claim 2, wherein the content of the mixed DC in the step 2 is 10-90%.
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| CN202211374703.1A CN115583905A (en) | 2022-11-04 | 2022-11-04 | Preparation method of m-di-tert-butylperoxydiisopropylbenzene |
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| CN104418706A (en) * | 2013-09-10 | 2015-03-18 | 中国石油化工集团公司 | Method for refining bi(2-hydroxyl isopropyl) benzene |
| CN106588735A (en) * | 2015-10-20 | 2017-04-26 | 中国石油化工集团公司 | Bis(t-butylperoxyisopropyl)benzene production method |
| CN112679317A (en) * | 2019-10-18 | 2021-04-20 | 中国石油化工股份有限公司 | Method for separating m-di- (2-hydroxyisopropyl) benzene and p-di- (2-hydroxyisopropyl) benzene |
| CN112679403A (en) * | 2019-10-18 | 2021-04-20 | 中国石油化工股份有限公司 | Method for preparing m-diisopropylbenzene hydroperoxide and p-diisopropylbenzene hydroperoxide |
| CN114308122A (en) * | 2022-01-12 | 2022-04-12 | 万华化学集团股份有限公司 | Quaternary ammonia base phase transfer catalyst, preparation method and application thereof in preparation of 1, 3-di (2-hydroxy isopropyl) benzene |
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| CN104418706A (en) * | 2013-09-10 | 2015-03-18 | 中国石油化工集团公司 | Method for refining bi(2-hydroxyl isopropyl) benzene |
| CN106588735A (en) * | 2015-10-20 | 2017-04-26 | 中国石油化工集团公司 | Bis(t-butylperoxyisopropyl)benzene production method |
| CN112679317A (en) * | 2019-10-18 | 2021-04-20 | 中国石油化工股份有限公司 | Method for separating m-di- (2-hydroxyisopropyl) benzene and p-di- (2-hydroxyisopropyl) benzene |
| CN112679403A (en) * | 2019-10-18 | 2021-04-20 | 中国石油化工股份有限公司 | Method for preparing m-diisopropylbenzene hydroperoxide and p-diisopropylbenzene hydroperoxide |
| CN114308122A (en) * | 2022-01-12 | 2022-04-12 | 万华化学集团股份有限公司 | Quaternary ammonia base phase transfer catalyst, preparation method and application thereof in preparation of 1, 3-di (2-hydroxy isopropyl) benzene |
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