CN112661686A - Method for producing peroxycarboxylic acid alkyl ester based on titanium silicalite molecular sieve composite catalyst - Google Patents
Method for producing peroxycarboxylic acid alkyl ester based on titanium silicalite molecular sieve composite catalyst Download PDFInfo
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Abstract
The invention relates to a method for synthesizing alkyl peroxycarboxylate based on a titanium silicalite molecular sieve composite catalyst, belonging to the technical field of peroxide production. The invention overcomes the defects of the prior art, and adopts the titanium silicalite molecular sieve and the metal oxide composite catalyst to synthesize the peroxycarboxylic acid alkyl ester. In the chemical reaction process of tert-butyl hydroperoxide or tert-amyl hydroperoxide and carboxylic acid to generate tert-butyl peroxycarboxylate or tert-amyl peroxycarboxylate, reaction water is generated. The reaction water is removed from the reaction mixture in good time. Azeotropic distillation and molecular distillation are generally adopted for dehydration. However, these processes require relatively high temperatures, which are detrimental to the stability and safety of the alkyl peroxycarboxylate. The catalyst of the invention contains metal oxide, and can absorb reaction to generate water in time, thereby ensuring that the synthesis reaction can be successfully completed.
Description
Technical Field
The invention relates to a method for producing alkyl peroxycarboxylate based on a titanium silicalite molecular sieve composite catalyst, belonging to the technical field of peroxide production.
Background
Tert-butyl peroxycarboxylate and t-amyl peroxycarboxylate are commercially important initiators for the polymerization of monomers, particularly polyacrylic acid, polyethylene, polyvinyl chloride, and polystyrenic products.
Chinese patent CN110981778A discloses a preparation method of cumyl peroxyneodecanoate and solvent-type CNP, wherein the preparation method utilizes the reaction of cumyl peroxyl, alkali liquor and neodecanoyl chloride to obtain water-in-oil emulsion.
Chinese patent CN106902869A discloses an immobilized phase transfer catalyst, which is prepared by the following method: adding the carrier into an organic solvent containing a phase transfer catalyst, heating, refluxing, reacting for 10-20 h, and then washing and filtering to obtain an immobilized quaternary ammonium salt phase transfer catalyst; the immobilized phase transfer catalyst can be applied to preparation of cumyl peroxyneodecanoate.
Chinese patent CN110256320A discloses a synthesis method of di (2-ethylhexyl) peroxydicarbonate, which adopts a micro-channel continuous flow reactor to mix hydrogen peroxide, sodium hydroxide and chlorinated ester for reaction to prepare the di (2-ethylhexyl) peroxydicarbonate product.
Chinese patent CN109265384A discloses a method for preparing di (2-ethylhexyl) peroxydicarbonate, which comprises performing a synthesis reaction in a microreactor, and using aqueous hydrogen peroxide, aqueous sodium hydroxide and (2-ethyl) chloroformate as raw materials to synthesize di (2-ethylhexyl) peroxydicarbonate.
Chinese patent CN109180549A discloses a safe production process of di-ethylhexyl peroxydicarbonate initiator, which is prepared from the following raw materials in parts by weight: 35-55 parts of chlorinated ester, 15-20 parts of hydrogen peroxide and 5-8 parts of sodium hydroxide.
Chinese patent CN109134334A discloses a safe production process of cumyl peroxyneodecanoate initiator, which is prepared from the following raw materials in parts by weight: 40-60 parts of cumyl hydroperoxide, 12-16 parts of sodium hydroxide and 15-19 parts of neodecyl chloroformate.
Chinese patent CN107827801A discloses a method for preparing an initiator for polymer synthesis, namely a method for preparing solvent type tert-butyl peroxyneodecanoate. Mixing and stirring neodecanoyl chloride, an alkaline solution and tert-butyl hydroperoxide for reaction at the temperature of 10-30 ℃, separating mother liquor, washing a reaction product to be neutral, and adding an alkane solvent to prepare the solvent type tert-butyl peroxyneodecanoate.
Chinese patent CN105693584A discloses cumyl peroxyneodecanoate and a method for preparing cumyl peroxyneodecanoate by a phase transfer catalyst.
Chinese patent CN105237454A discloses a preparation method of cumyl neodecanoate, wherein the raw materials are 7% of hydrogen peroxide, 46% of potassium hydroxide and chlorinated ester to synthesize the target product.
Chinese patent CN104592080A discloses a method for preparing tert-butyl peroxyneodecanoate (BNP) by continuous flow, wherein neodecanoyl chloride solution reacts with the product of alkaline aqueous solution and tert-butyl hydrogen peroxide aqueous solution to prepare a solvent type or emulsion type tert-butyl peroxyneodecanoate (BNP).
Chinese patent CN1491210A discloses a method for preparing peroxyester, which uses hydroperoxide salt and acyl halide or acid anhydride as raw materials, and is implemented in aqueous medium, and the obtained peroxyester product is aqueous emulsion.
The commercial synthesis of tert-butyl peroxycarboxylate is prepared from tert-butyl hydroperoxide and the corresponding acid chloride. In the prior art, tert-butyl peroxypivalate is synthesized by taking tert-butyl hydroperoxide, NaOH aqueous solution and pivaloyl chloride as raw materials. Tert-amyl peroxypivalate and tert-heptyl peroxypivalate can also be synthesized in a similar manner.
As is clear from the above, the above synthesis method is basically a synthesis method using an acid chloride under strongly alkaline conditions. One disadvantage of using acid chlorides is that they are themselves very expensive, and another disadvantage is that the use of acid chlorides can form the corrosive substance hydrogen chloride. In addition, the use of acyl chloride as a raw material also presents environmental problems in the form of chloride waste water and waste solids. Accordingly, there is a need for improved processes for the production of t-butyl peroxycarboxylate and t-amyl peroxycarboxylate.
Disclosure of Invention
The invention aims to provide a method for producing alkyl peroxycarboxylate based on a titanium-silicon molecular sieve composite catalyst, which can timely adsorb the generated water of the reaction due to the metal oxide, thereby ensuring the smooth synthesis reaction, and simultaneously, does not use acyl chloride as a raw material, and avoids the formation of corrosive substance hydrogen chloride.
The invention relates to a method for producing peroxycarboxylic acid alkyl ester based on a titanium silicalite molecular sieve composite catalyst, which comprises the steps of contacting carboxylic acid with alkyl hydroperoxide in the presence of the titanium silicalite molecular sieve composite catalyst, and dehydrating to synthesize peroxycarboxylic acid alkyl ester; the titanium silicalite molecular sieve composite catalyst is prepared by compounding a titanium silicalite molecular sieve and a metal oxide.
Wherein:
the mass ratio of the titanium-silicon molecular sieve to the metal oxide is 1: 1-1000, preferably 1: 20-500, more preferably 1: between 20 and 200.
The metal oxide is one or more of calcium oxide or barium oxide; when the calcium oxide and the barium oxide are combined, the mass ratio of the calcium oxide to the barium oxide is 0.5-2: 0.5-1, and the mass ratio of the two is preferably 1: 1.
the titanium-silicon molecular sieve composite catalyst accounts for 20-200% of the total mass of the alkyl hydroperoxide, preferably 50-150%, and more preferably 80-120%.
The carboxylic acid is contacted with alkyl hydroperoxide, and the carboxylic acid alkyl peroxide is synthesized by dehydration at the temperature of-20 to 100 ℃; the synthesis time is 1-8 h.
The water generated during the synthesis of alkyl peroxycarboxylate by dehydration is removed by the metal oxide.
The preparation method of the titanium silicalite molecular sieve composite catalyst comprises the steps of uniformly mixing a titanium silicalite molecular sieve and a metal oxide in an oil phase to obtain slurry, carrying out vacuum filtration, drying and cooling to obtain the titanium silicalite molecular sieve composite catalyst.
The oil phase is one or more of methylbenzene, ethylbenzene or isopropylbenzene, the drying temperature is 150-250 ℃, and the drying time is 2-5 hours.
In the presence of a titanium-silicon molecular sieve composite catalyst and a solvent, carboxylic acid is contacted with alkyl hydroperoxide, and carboxylic acid alkyl peroxide is synthesized by dehydration. The invention can also react in the presence of a solvent, wherein the solvent can be petroleum ether, toluene or isododecane and the like.
The carboxylic acid has the structural formula R1-COOH，R1The group is a straight chain or branched chain or C1-C16 group with aromatic ring; the structural formula of the alkyl hydroperoxide is R2-OOH。
The R is1The group is methyl, ethyl, propyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, tert-pentyl, cyclopentyl, cyclohexyl, phenyl, benzyl, phenethyl, phenylpropyl, isooctyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, 1-ethylpentyl or 1-ethyl-1, 4-dimethylpentyl, etc.; the R is2The group is tert-butyl or tert-pentyl.
In actual work in laboratory, we found a new composite catalyst to prepare alkyl peroxycarboxylate, which avoids the disadvantages of using acyl chloride as raw material to prepare alkyl peroxycarboxylate.
The invention relates to a method for preparing carboxylic acid alkyl peroxide by carboxylic acid and alkyl hydroperoxide under the action of a titanium silicalite molecular sieve and a metal oxide composite catalyst. Such as t-butyl peroxyneodecanoate, t-butyl peroxy-2-ethylhexanoate, and the like.
The invention adopts titanium-silicon molecular sieve and metal oxide composite catalyst to synthesize peroxycarboxylic acid alkyl ester, in particular to peroxycarboxylic acid tert-butyl ester and peroxycarboxylic acid tert-amyl ester initiator which is applied to the fields of polyacrylic acid, polyethylene, polyvinyl chloride and polystyrene. The invention overcomes the defects of the prior art, and adopts the titanium silicalite molecular sieve and the metal oxide composite catalyst to synthesize the peroxycarboxylic acid alkyl ester.
The invention takes a commercial titanium silicalite molecular sieve and a commercial metal oxide as raw materials, and compounds the commercial titanium silicalite molecular sieve and the commercial metal oxide into a catalyst by uniformly mixing a laboratory oil phase, thereby obtaining the titanium silicalite molecular sieve composite catalyst with catalytic action.
Commercial titanium silicalite molecular sieves come in a variety of varieties, such as TS-1, TS-2, Ti-ZSM-48, Ti-FER, Ti-Beta, TPSO-5, Ti-ZSM-12, Ti-MOR, Ti-MCM-68, Ti-ITQ-7, Ti-MWW, Ti-UTD-1, Ti-MCM-41, Ti-MCM-48, Ti-SBA-15, Ti-HMS, Ti-MTS-9, and the like. The invention preferably selects the TS-1 type commercial titanium silicalite molecular sieve product.
The commercial metal oxide used for the composition with the titanium silicalite is generally calcium oxide, barium oxide, etc., with calcium oxide being preferred.
More preferably, the weight ratio of calcium oxide to barium oxide is 1: 1 mixing the obtained composite metal oxide.
The composite ratio of the titanium silicalite molecular sieve to the metal oxide is 1: 1-1000, preferably 1: 20 to 500, more preferably 1: 50 to 200.
Generally, the alkyl hydroperoxide and carboxylic acid can be reacted in a wide range of molar ratios in order to increase the yield of the reaction product. Typical molar ratios of e.g. tert-butyl hydroperoxide to carboxylic acid vary between 0.1 and 5. In the process of the invention, it is preferred to react equimolar amounts of tert-butyl hydroperoxide and carboxylic acid.
The amount of titanium silicalite and metal oxide composite catalyst added depends on several factors known to those skilled in the art of peroxide reaction, including the reactivity between t-butyl hydroperoxide and carboxylic acid; the synthesis reaction conditions are temperature and reaction time, stirring speed and the like. In the present invention, the amount of the titanium silicalite molecular sieve and the metal oxide composite catalyst is usually 20 to 200%, preferably 50 to 150%, more preferably 80 to 120% based on the weight of the added tert-butyl hydroperoxide or tert-amyl hydroperoxide.
According to the process of the present invention, the synthetic peroxide reaction can be carried out over a wide temperature range. The reaction temperature is usually controlled to be between-20 ℃ and 100 ℃, preferably between 0 ℃ and 80 ℃, more preferably between 10 ℃ and 60 ℃. The reaction temperature is usually varied according to the physicochemical properties of the product itself.
The chemical reaction formula of the invention is as follows:
H2O+CaO→Ca(OH)2
H2O+BaO→Ba(OH)2
the reaction mechanism of the present invention is presumed as follows:
the invention has the following beneficial effects:
in the chemical reaction process of tert-butyl hydroperoxide or tert-amyl hydroperoxide and carboxylic acid to generate tert-butyl peroxycarboxylate or tert-amyl peroxycarboxylate, reaction water is generated. The reaction water needs to be removed from the reaction mixture in good time. Azeotropic distillation and molecular distillation are generally adopted for dehydration. However, these processes require relatively high temperatures, which are disadvantageous for the stability and safety of the alkyl peroxycarboxylate and may even result in side reactions. The invention overcomes the defects of the prior art, adopts the titanium-silicon molecular sieve and the metal oxide composite catalyst to synthesize the peroxycarboxylic acid alkyl ester, and ensures the smooth completion of the synthesis reaction because the composite catalyst contains the metal oxide and absorbs and reacts in time to generate water.
Meanwhile, the invention avoids the use of acyl chloride, saves chemical raw materials and avoids the formation of corrosive substance hydrogen chloride. More importantly, the method solves the problems of chloride wastewater and waste solids caused by taking acyl chloride as a raw material. Therefore, the invention is an environment-friendly production method.
Drawings
FIG. 1 is a gas chromatogram of a solution containing tert-butyl peroxyneodecanoate of example 1.
Detailed Description
The present invention is further illustrated by the following specific examples.
Example 1
In a 500ml three-necked flask, 20 ml of isododecane was added, 30g of t-butyl hydroperoxide having a purity of 99.5 wt.% was added, 57.3g of neodecanoic acid was added, and 20g of the composite catalyst A was added. The mixture was stirred at 0 ℃ for 6 hours. The composite catalyst A was recovered by filtration with a sand core filter to obtain 74.5g of a solution containing tert-butyl peroxyneodecanoate. The yield was 78% based on the mass of the raw materials charged. The gas chromatography analysis solution contained 60.8% of tert-butyl peroxyneodecanoate. See fig. 1.
Gas chromatography experimental conditions: 2m x phi 3mm stainless steel column; stationary phase: coating 5% SE-30 on 60-80 mesh white supporter; the column temperature is 40 ℃, the vaporization temperature is 90 ℃, and the detector FID temperature is 110 ℃.
Example 2
50 ml of isododecane was charged into a 500ml three-necked flask, 30g of t-butyl hydroperoxide having a purity of 99.5 wt.% was added, 57.3g of neodecanoic acid was added, and 15g of the composite catalyst B was added. The mixture was stirred at 10 ℃ for 6 hours. The composite catalyst B was recovered by filtration with a sand core filter to obtain 112.4g of a solution containing tert-butyl peroxyneodecanoate in a yield of 86% by mass of the charged raw materials. The gas chromatography analysis solution contained 19.0% of tert-butyl peroxyneodecanoate.
Example 3
100 ml of toluene was added to a 500ml three-necked flask, 30g of t-butyl hydroperoxide having a purity of 99.5 wt.% was added, 57.3g of neodecanoic acid was added, and 15g of the composite catalyst C was added. The mixture was stirred at 20 ℃ for 4 hours. The composite catalyst C was recovered by filtration with a sand core filter to obtain 161.6g of a solution containing tert-butyl peroxyneodecanoate, which was obtained in a yield of 89% based on the mass of the charged raw materials. The gas chromatography analysis solution contained 17.5% of tert-butyl peroxyneodecanoate.
Example 4
50 ml of toluene was added to a 500ml three-necked flask, 25g of t-butyl hydroperoxide having a purity of 99.5 wt.% was added, 40g of 2-ethylhexanoic acid was added, and 20g of composite catalyst D was added. The mixture was stirred at 40 ℃ for 4 hours. The composite catalyst D was recovered by filtration with a sand core filter to obtain 82.5g of a solution containing tert-butyl peroxy-2-ethylhexanoate at a yield of 75% by mass of the charged raw materials. The GC analysis solution contained 32.5% t-butyl peroxy-2-ethylhexanoate.
Example 5
In a 500ml three-necked flask, 15 ml of toluene was added, 25g of t-butyl hydroperoxide having a purity of 99.5 wt.% was added, 40g of 2-ethylhexanoic acid was added, and 20g of composite catalyst E was added. The mixture was stirred at 60 ℃ for 2 hours. The composite catalyst E was recovered by filtration with a sand core filter to obtain 58.8g of a solution containing tert-butyl peroxy-2-ethylhexanoate in a yield of 78% by mass of the charged raw materials. The GC analysis solution contained 41.5% t-butyl peroxy-2-ethylhexanoate.
Comparative example 1
Adding 100g of 25 wt.% sodium hydroxide solution into a 500ml three-necked bottle, and stirring and cooling to 5 ℃; dropwise adding 30g of tert-butyl hydroperoxide with the purity of 99.5 wt.% to react for 30 minutes, and controlling the temperature to be 10-30 ℃; after stirring uniformly, slowly dripping 35g of pivaloyl chloride with the concentration of 80 wt.% and 50g of solvent oil into a three-neck flask, controlling the reaction temperature at 10-30 ℃, completing the addition within 1.5 hours, and stirring and reacting for 30 minutes after the pivaloyl chloride solution is added; stopping stirring after the reaction is finished, standing for 40 minutes, separating out reaction mother liquor, and washing a reaction product until the pH value is 5-7; 95g of tert-butyl peroxyneodecanoate was obtained in a yield of 86%.
The composite catalyst in the examples was synthesized as follows:
1. 500 g of toluene is added into a 1000 ml three-neck flask, stirring is started, and the rotating speed is controlled within 200 r/min. Adding 1g of TS-1 type commercial titanium silicalite molecular sieve product, adding 200g of calcium oxide, and stirring for 30 minutes to obtain uniform slurry.
2. And transferring the uniform slurry into a sand core filter, performing vacuum filtration to obtain the required composite catalyst on the sand core filter, and recycling the filtered toluene.
3. The composite catalyst obtained above was put into a vacuum oven at 200 ℃ and activated for 4 hours.
4. And cooling to obtain the composite catalyst A with catalytic activity.
The composite catalyst B was obtained according to the above preparation method by replacing 200g of calcium oxide in the above step with 200g of barium oxide.
Composite catalyst C was obtained according to the above preparation method by replacing 200g of calcium oxide in the above step with 100g of mixed metal oxide of calcium oxide and 100g of barium oxide.
Composite catalyst D was obtained according to the above preparation method by replacing 200g of calcium oxide in the above step with 150g of mixed metal oxide of calcium oxide and 50g of barium oxide.
Composite catalyst E was obtained according to the above preparation method by replacing 200g of calcium oxide in the above step with 50g of mixed metal oxide of calcium oxide and 150g of barium oxide.
The preparation methods of the composite catalyst can be various, and the mass composite proportion of the titanium-silicon molecular sieve and the metal oxide can be 1: 1; 1: 20; 1: 50; 1: 100, respectively; 1: 150; 1: 500, a step of; 1: 1000, etc., as long as the mass composite ratio of the titanium-silicon molecular sieve to the metal oxide is 1: 1-1000.
Claims (10)
1. A method for producing alkyl peroxycarboxylate based on a titanium silicalite molecular sieve composite catalyst is characterized in that: in the presence of a titanium silicalite molecular sieve composite catalyst, carboxylic acid is contacted with alkyl hydroperoxide, and carboxylic acid alkyl peroxide is synthesized by dehydration; the titanium silicalite molecular sieve composite catalyst is prepared by compounding a titanium silicalite molecular sieve and a metal oxide.
2. The method for producing alkyl peroxycarboxylate based on titanium silicalite molecular sieve composite catalyst as claimed in claim 1, wherein: the mass ratio of the titanium-silicon molecular sieve to the metal oxide is 1: 1 to 1000.
3. The method for producing alkyl peroxycarboxylate based on titanium silicalite molecular sieve composite catalyst as claimed in claim 1, wherein: the metal oxide is one or more of calcium oxide or barium oxide; when the calcium oxide and the barium oxide are combined, the mass ratio of the calcium oxide to the barium oxide is 0.5-2: 0.5 to 1.
4. The method for producing alkyl peroxycarboxylate based on titanium silicalite molecular sieve composite catalyst as claimed in claim 1, wherein: the titanium-silicon molecular sieve composite catalyst accounts for 20-200% of the total mass of the alkyl hydroperoxide; the carboxylic acid is contacted with alkyl hydroperoxide, and the carboxylic acid alkyl peroxide is synthesized by dehydration at the temperature of-20 to 100 ℃; the synthesis time is 1-8 h; the water generated during the synthesis of alkyl peroxycarboxylate by dehydration is removed by the metal oxide.
5. The method for producing alkyl peroxycarboxylate based on titanium silicalite molecular sieve composite catalyst as claimed in claim 1, wherein: the preparation method of the titanium silicalite molecular sieve composite catalyst comprises the steps of uniformly mixing a titanium silicalite molecular sieve and a metal oxide in an oil phase to obtain slurry, carrying out vacuum filtration, drying and cooling to obtain the titanium silicalite molecular sieve composite catalyst.
6. The method for producing alkyl peroxycarboxylate based on titanium silicalite molecular sieve composite catalyst as claimed in claim 1, wherein: the oil phase is one or more of methylbenzene, ethylbenzene or isopropylbenzene, the drying temperature is 150-250 ℃, and the drying time is 2-5 hours.
7. The method for producing alkyl peroxycarboxylate based on titanium silicalite molecular sieve composite catalyst as claimed in any one of claims 1 to 6, wherein: in the presence of a titanium-silicon molecular sieve composite catalyst and a solvent, carboxylic acid is contacted with alkyl hydroperoxide, and carboxylic acid alkyl peroxide is synthesized by dehydration.
8. The method for producing alkyl peroxycarboxylate based on titanium silicalite molecular sieve composite catalyst as claimed in claim 1, wherein: the solvent is petroleum ether, toluene or isododecane.
9. Titanium-based according to claim 1The method for producing the peroxycarboxylic acid alkyl ester by using the silicon molecular sieve composite catalyst is characterized by comprising the following steps: the carboxylic acid has the structural formula R1-COOH，R1The group is a straight chain or branched chain or C1-C16 group with aromatic ring; the structural formula of the alkyl hydroperoxide is R2-OOH。
10. The method for producing alkyl peroxycarboxylate based on titanium silicalite molecular sieve composite catalyst of claim 9, wherein: the R is1The group is methyl, ethyl, propyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, tert-pentyl, cyclopentyl, cyclohexyl, phenyl, benzyl, phenethyl, phenylpropyl, isooctyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, 1-ethylpentyl or 1-ethyl-1, 4-dimethylpentyl; the R is2The group is tert-butyl or tert-pentyl.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115557870A (en) * | 2022-10-17 | 2023-01-03 | 辽宁中茂新材料有限公司 | Synthesis method of peroxy-2-ethylhexanoate tert-amyl ester |
| CN115850537A (en) * | 2022-12-29 | 2023-03-28 | 乌鲁木齐市华泰隆化学助剂有限公司 | Organic peroxide initiator using alkaline earth metal catalyst and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20010021369A1 (en) * | 1999-12-24 | 2001-09-13 | Min Lin | Titanium-silicalite molecular sieve and the method for its preparation |
| CN1346705A (en) * | 2001-09-13 | 2002-05-01 | 大连理工大学 | Process for preparing composite catalyst and its application |
| CN102441429A (en) * | 2010-10-11 | 2012-05-09 | 中国石油化工股份有限公司 | Olefin epoxidation catalyst, preparation method, and method for epoxidation of olefin |
| CN109331871A (en) * | 2018-11-20 | 2019-02-15 | 淄博正华助剂股份有限公司 | The synthetic method of the tertiary fourth/pentyl ester of carboxylic acid peroxide |
-
2020
- 2020-12-25 CN CN202011565101.5A patent/CN112661686B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20010021369A1 (en) * | 1999-12-24 | 2001-09-13 | Min Lin | Titanium-silicalite molecular sieve and the method for its preparation |
| CN1346705A (en) * | 2001-09-13 | 2002-05-01 | 大连理工大学 | Process for preparing composite catalyst and its application |
| CN102441429A (en) * | 2010-10-11 | 2012-05-09 | 中国石油化工股份有限公司 | Olefin epoxidation catalyst, preparation method, and method for epoxidation of olefin |
| CN109331871A (en) * | 2018-11-20 | 2019-02-15 | 淄博正华助剂股份有限公司 | The synthetic method of the tertiary fourth/pentyl ester of carboxylic acid peroxide |
Non-Patent Citations (2)
| Title |
|---|
| LIANG GE ET AL.: "Iron-Catalyzed Vinylic C−H Alkylation with Alkyl Peroxides", 《CHEMISTRY AN ASIAN JOURNAL》 * |
| 王基铭等: "《石油化工技术进展》", 31 December 2002 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115557870A (en) * | 2022-10-17 | 2023-01-03 | 辽宁中茂新材料有限公司 | Synthesis method of peroxy-2-ethylhexanoate tert-amyl ester |
| CN115557870B (en) * | 2022-10-17 | 2023-11-21 | 辽宁中茂新材料有限公司 | Synthesis method of tert-amyl peroxy-2-ethylhexanoate |
| CN115850537A (en) * | 2022-12-29 | 2023-03-28 | 乌鲁木齐市华泰隆化学助剂有限公司 | Organic peroxide initiator using alkaline earth metal catalyst and preparation method thereof |
| CN115850537B (en) * | 2022-12-29 | 2024-01-26 | 乌鲁木齐市华泰隆化学助剂有限公司 | Preparation method of organic peroxide initiator using alkaline earth metal catalyst |
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