CN102199114B - Method for preparing raw material for producing dicumyl peroxide - Google Patents
Method for preparing raw material for producing dicumyl peroxide Download PDFInfo
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- CN102199114B CN102199114B CN2011100596726A CN201110059672A CN102199114B CN 102199114 B CN102199114 B CN 102199114B CN 2011100596726 A CN2011100596726 A CN 2011100596726A CN 201110059672 A CN201110059672 A CN 201110059672A CN 102199114 B CN102199114 B CN 102199114B
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- isopropyl benzene
- dcp
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Abstract
The invention discloses a method for preparing a raw material for producing dicumyl peroxide (DCP), and belongs to the technical field of catalytic oxidization of isopropylbenzene. In the method, a mixture of alkaline ionic liquid and sodium carbonate is taken as a catalyst, air is taken as an oxygen source, and the isopropylbenzene is subjected to catalytic oxidation to form a mixture of cumyl hydroperoxide and dimethyl-benzyl alcohol in a ratio of approximately 1:1. The obtained mixture is directly condensed to form the DCP, a reduction step in the process of producing the raw material of DCP is saved, and the production cost of DCP is reduced.
Description
Technical field
The present invention relates to a kind of preparation method of the raw material for the production of dicumyl peroxide, belong to isopropyl benzene catalyzed oxidation technical field.
Background technology
Dicumyl peroxide (DCP) is important novel organo-peroxide auxiliary agent, is optimum good initiator, vulcanizing agent, linking agents of the macromolecular materials such as natural gum, synthetical glue, polyvinyl resin, and purposes is widely arranged.
The production process of DCP, generally take isopropyl benzene as raw material, sodium carbonate or sodium hydroxide are catalyzer, under the oxidation of air or oxygen, cumene oxidation is become to hydrogen phosphide cumene, again hydrogen phosphide cumene is reduced into to dimethyl benzyl alcohol with S-WAT, dimethyl benzyl alcohol and hydrogen phosphide cumene are condensed into to DCP in the ratio of 1: 1 under sour catalysis.Reaction process is as shown in Figure 1:
At present, about patent and the bibliographical information of DCP fewer, Patents also majority concentrates on cumene oxidation decomposition production phenol field, main purpose is all on the selectivity of transformation efficiency in order to improve isopropyl benzene and hydrogen phosphide cumene, as U.S. Pat 6291718, all mentioned in US6476276 in the oxidation of alkylbenzene and to have added a kind of special compound that can Mulberry Extract.Add 2,2,6 of 18mg in the mixture of 144g isopropyl benzene and 36g isopropyl benzene hydroperoxide, 6-tetramethyl piperidine oxide compound, all these joins 0.05% the Na of 90g
2CO
3In the aqueous solution, after reacting 3 hours, the selectivity of isopropyl benzene hydroperoxide is 91mol%.Be catalyst oxidation isopropyl benzene and diisopropylbenzene(DIPB) as mentioned with alkali ionic liquid in Chinese patent 200810102379.1, can improve significantly the transformation efficiency of diisopropylbenzene(DIPB) and to the selectivity of hydrogen peroxide product.
Summary of the invention
Purpose of the present invention is reduced into the link of benzylalcohol by hydrogen phosphide cumene in the DCP production process, and a kind of preparation method of the raw material for the production of DCP is provided, and gained mixture direct polycondensation of the present invention can be generated to DCP.
For achieving the above object, technical scheme of the present invention: adopt the mixture of alkali ionic liquid and sodium carbonate as catalyzer, using air as oxygen source, isopropyl benzene is made to the mixture of hydrogen phosphide cumene and dimethyl benzyl alcohol through catalyzed oxidation.
Alkali ionic liquid of the present invention is imidazole type, pyridine type, quaternary ammonium or quaternary alkylphosphonium salt type alkali ionic liquid, and concrete structure is as follows:
X-=OH in above formula
-, R, R
1, R
2, R
3, R
4, R ' is C
1-C
18Alkyl, be preferably C
1-C
16Alkyl, R, R
1, R
2, R
3, R
4, R ' can be identical, also can be not identical.
The known art methods preparation that the present invention's alkali ionic liquid used adopts those skilled in the art to know.
The mass ratio of described alkali ionic liquid and sodium carbonate is 1-100: 1.
The quality that adds ionic liquid in catalytic oxidation process is isopropyl benzene 0.001～1 times, be preferably: 0.002～0.5 times.
The temperature of reaction of catalyzed oxidation is 60～150 ℃, and air flow quantity is 25～120L/ (hmol isopropyl benzene), and the reaction times is 2～72 hours, is preferably 15～36 hours.
The invention effect: method of the present invention adopts alkali ionic liquid and sodium carbonate mixture as catalyzer, in the rate of oxidation that has improved isopropyl benzene, produce a considerable amount of hydrogen phosphide cumenes and dimethyl benzyl alcohol, being about to cumene oxidation becomes hydrogen phosphide cumene and dimethyl benzyl alcohol ratio to approach the mixture of 1: 1, avoided in the DCP production process, hydrogen phosphide cumene being reduced into the link of benzylalcohol, this mixture direct polycondensation can generate DCP.Can directly carry out condensation and obtain DCP, save the reduction step in DCP raw material production process, reduce the DCP production cost.And adopt the alkali ionic liquid polymkeric substance as catalyzer, not only improve the rate of oxidation of alkylbenzene and the selectivity of raising hydroperoxide, catalyzer easily separates with reactant flow simultaneously, has reduced the shadow to subsequent technique.
The accompanying drawing explanation
Fig. 1 isopropyl benzene prepares the reaction process of DCP.
Embodiment
Comparative Examples 1
Comparative Examples 1 is the base catalysis method for oxidation usually adopted.
Getting the 15g isopropyl benzene is put in the there-necked flask with backflow device, stirring, add the mass percentage concentration 1.5gNaOH aqueous solution (mass concentration 2%), 90 ℃ of temperature of reaction, pass into air 200ml/min, react after 24 hours, the transformation efficiency of isopropyl benzene is 30%, and the selectivity of hydrogen phosphide cumene is 90%.
Embodiment 1
Getting the 15g isopropyl benzene is put in the there-necked flask with backflow device, stirring, add 0.08g hydroxide 1-methyl, the 3-butyl imidazole, 0.02g sodium carbonate, 60 ℃ of temperature of reaction, pass into air 200ml/min, react after 24 hours, the transformation efficiency of isopropyl benzene is 80%, and the selectivity of hydrogen phosphide cumene is 45%, the selectivity 40% of dimethyl benzyl alcohol.
Embodiment 2
Getting the 15g isopropyl benzene is put in the there-necked flask with backflow device, stirring, add 0.1g hydroxide 1-methyl, 3-hexyl imidazoles, 0.1g sodium carbonate, 90 ℃ of temperature of reaction, pass into air 150ml/min, after reacting 36 hours, the transformation efficiency of isopropyl benzene is 94%, and the selectivity of hydrogen phosphide cumene is 37%.The selectivity 40% of dimethyl benzyl alcohol.
Embodiment 3
Get the 15g isopropyl benzene and be put in the there-necked flask with backflow device, stirring, add 6.69g hydroxide butyl-pyridinium, 1.02g sodium carbonate, 90 ℃ of temperature of reaction, pass into air 150ml/min, after reacting 36 hours, the transformation efficiency of isopropyl benzene is 94%, and the selectivity of hydrogen phosphide cumene is 42%.The selectivity 40% of dimethyl benzyl alcohol.
Embodiment 4
Getting the 20g isopropyl benzene is put in the there-necked flask with backflow device, stirring, add the 1.54g tetraethyl ammonium hydroxide, 0.62g 100 ℃ of sodium carbonate temperature of reaction, pass into air 160ml/min, react after 33 hours, the transformation efficiency of isopropyl benzene is 99%, and the selectivity of hydrogen phosphide cumene is 35%, the selectivity 30% of dimethyl benzyl alcohol
Embodiment 5
Getting the 15g isopropyl benzene is put in the there-necked flask with backflow device, stirring, add 0.07g hydroxide 1-methyl 3-ethyl imidazol(e), 0.02g sodium carbonate, 105 ℃ of temperature of reaction, pass into air 100ml/min, after reacting 20 hours, the transformation efficiency of isopropyl benzene is 75%, the selectivity of hydrogen peroxide isopropyl benzene is 46%, the selectivity 42% of dimethyl benzyl alcohol
Embodiment 6
Getting the 15g isopropyl benzene is put in the there-necked flask with backflow device, stirring, add 2.00g hydroxide 1-methyl 3-octadecyl imidazoles, 0.02g sodium carbonate, 100 ℃ of temperature of reaction, pass into air 100ml/min, after reacting 16 hours, the transformation efficiency of isopropyl benzene is 85%, the selectivity of hydrogen peroxide isopropyl benzene is 49%, the selectivity 44% of dimethyl benzyl alcohol.
Claims (3)
1. the preparation method for the production of the raw material of dicumyl peroxide, it is characterized in that, adopt the mixture of alkali ionic liquid and sodium carbonate as catalyzer, using air as oxygen source, isopropyl benzene is made to the mixture of hydrogen phosphide cumene and dimethyl benzyl alcohol through catalyzed oxidation;
Alkali ionic liquid is imidazole type, pyridine type, quaternary ammonium Huo quaternary phosphine salt type alkali ionic liquid, and concrete structure is as follows:
X in above formula
-=OH
-, R, R
1, R
2, R
3, R
4, R' is C
1-C
18Alkyl, R, R
1, R
2, R
3, R
4, R' can be identical, also can be not identical;
The mass ratio of alkali ionic liquid and sodium carbonate is 1-100:1; The quality of ionic liquid is 0.001～1 times of isopropyl benzene; The temperature of reaction of catalyzed oxidation is 60～150 ℃, and air flow quantity is 25～120L/ (hmol isopropyl benzene), and the reaction times is 2～72 hours.
2. according to the method for claim 1, it is characterized in that, the quality of ionic liquid is isopropyl benzene 0.002～0.5 times.
3. according to the method for claim 1, it is characterized in that, the reaction times is 15～36 hours.
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| CN2011100596726A CN102199114B (en) | 2011-03-11 | 2011-03-11 | Method for preparing raw material for producing dicumyl peroxide |
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| CN102199114B true CN102199114B (en) | 2013-12-04 |
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| CN104860861B (en) * | 2015-04-01 | 2017-08-08 | 中石化上海工程有限公司 | The method for producing cumyl peroxide |
| CN115403446B (en) * | 2022-09-01 | 2023-12-29 | 山东阳谷华泰化工股份有限公司 | Synthesis method of alpha, alpha' -dihydroxyl-1, 3-diisopropylbenzene |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB681990A (en) * | 1949-01-25 | 1952-11-05 | Distillers Co Yeast Ltd | Oxidation of aromatic hydrocarbons |
| US2681936A (en) * | 1950-08-03 | 1954-06-22 | Allied Chem & Dye Corp | Sodium carbonate in cumene oxidation |
| CN101538020A (en) * | 2008-03-21 | 2009-09-23 | 北京化工大学 | Method for producing hydroperoxides by catalytic oxidation of aromatic hydrocarbons containing isopropyl |
-
2011
- 2011-03-11 CN CN2011100596726A patent/CN102199114B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB681990A (en) * | 1949-01-25 | 1952-11-05 | Distillers Co Yeast Ltd | Oxidation of aromatic hydrocarbons |
| US2681936A (en) * | 1950-08-03 | 1954-06-22 | Allied Chem & Dye Corp | Sodium carbonate in cumene oxidation |
| CN101538020A (en) * | 2008-03-21 | 2009-09-23 | 北京化工大学 | Method for producing hydroperoxides by catalytic oxidation of aromatic hydrocarbons containing isopropyl |
Non-Patent Citations (4)
| Title |
|---|
| 《异丙苯催化氧化的研究进展》;郭建维等;《化学反应工程与工艺》;20010331;第17卷(第1期);第73-77页 * |
| 《异丙苯氧化的研究进展 》;吴俊荣等;《广州化工》;20060331;第34卷(第3期);第7-10页 * |
| 吴俊荣等.《异丙苯氧化的研究进展 》.《广州化工》.2006,第34卷(第3期),第7-10页. |
| 郭建维等.《异丙苯催化氧化的研究进展》.《化学反应工程与工艺》.2001,第17卷(第1期),第73-77页. |
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