CN102199114A - 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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- CN102199114A CN102199114A CN2011100596726A CN201110059672A CN102199114A CN 102199114 A CN102199114 A CN 102199114A CN 2011100596726 A CN2011100596726 A CN 2011100596726A CN 201110059672 A CN201110059672 A CN 201110059672A CN 102199114 A CN102199114 A CN 102199114A
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- CN
- China
- Prior art keywords
- cumene
- ionic liquid
- dcp
- mixture
- isopropyl benzene
- 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.)
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- 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 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 13
- 239000002994 raw material Substances 0.000 title claims abstract description 9
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims abstract description 92
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 26
- 230000003647 oxidation Effects 0.000 claims abstract description 15
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 15
- JESIHYIJKKUWIS-UHFFFAOYSA-N 1-(4-Methylphenyl)ethanol Chemical compound CC(O)C1=CC=C(C)C=C1 JESIHYIJKKUWIS-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002608 ionic liquid Substances 0.000 claims abstract description 13
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000003197 catalytic effect Effects 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 11
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 239000011830 basic ionic liquid Substances 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000004714 phosphonium salts Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 239000003054 catalyst Substances 0.000 abstract description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 13
- 235000017550 sodium carbonate Nutrition 0.000 description 10
- 230000009466 transformation Effects 0.000 description 9
- 239000003513 alkali Substances 0.000 description 8
- 230000005587 bubbling Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 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
- 101000648997 Homo sapiens Tripartite motif-containing protein 44 Proteins 0.000 description 2
- 102100028017 Tripartite motif-containing protein 44 Human genes 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 2
- MRIZMKJLUDDMHF-UHFFFAOYSA-N cumene;hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC=C1 MRIZMKJLUDDMHF-UHFFFAOYSA-N 0.000 description 2
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 description 1
- MNFDTZUJKUWRKQ-UHFFFAOYSA-M 1-butylpyridin-1-ium;hydroxide Chemical compound [OH-].CCCC[N+]1=CC=CC=C1 MNFDTZUJKUWRKQ-UHFFFAOYSA-M 0.000 description 1
- KGWVFQAPOGAVRF-UHFFFAOYSA-N 1-hexylimidazole Chemical class CCCCCCN1C=CN=C1 KGWVFQAPOGAVRF-UHFFFAOYSA-N 0.000 description 1
- RPAVJNIJEFCOCN-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCN1C=CN(C)C1.O Chemical class CCCCCCCCCCCCCCCCCCN1C=CN(C)C1.O RPAVJNIJEFCOCN-UHFFFAOYSA-N 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- -1 hydrogen phosphide cumenes Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明公开了一种用于生产过氧化二异丙苯的原料的制备方法，属于异丙苯催化氧化技术领域。本发明采用碱性离子液体和碳酸钠的混合物作为催化剂，以空气作为氧源，将异丙苯经催化氧化制成过氧化氢异丙苯和二甲基苄醇接近1∶1比例的混合物。将本发明所得混合物直接缩合即可生成DCP，省去了DCP原料生产过程中的还原步骤，降低了DCP生产成本。The invention discloses a method for preparing raw materials for producing dicumyl peroxide, and belongs to the technical field of cumene catalytic oxidation. The invention adopts the mixture of alkaline ionic liquid and sodium carbonate as a catalyst, and uses air as an oxygen source to catalyze and oxidize cumene to prepare a mixture of cumene hydroperoxide and dimethyl benzyl alcohol in a ratio close to 1:1. The DCP can be produced by directly condensing the mixture obtained in the present invention, which saves the reduction step in the production process of the DCP raw material and reduces the production cost of the DCP.
Description
Technical field
The present invention relates to a kind of preparation method who is used to produce the raw material 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 macromolecular materials such as natural gum, synthetical glue, polyvinyl resin, and purposes is widely arranged.
The production process of DCP, it generally is raw material with the isopropyl benzene, yellow soda ash or sodium hydroxide are catalyzer, under the oxidation of air or oxygen, cumene oxidation is become hydrogen phosphide cumene, again hydrogen phosphide cumene is reduced into dimethyl benzyl alcohol with S-WAT, dimethyl benzyl alcohol and hydrogen phosphide cumene are condensed into DCP in 1: 1 ratio under the catalysis of acid.Reaction process is as shown in Figure 1:
At present, about patent and the bibliographical information of DCP fewer, relevant patent also majority concentrates on cumene oxidation decomposition production phenol field, main purpose all is on the selectivity for transformation efficiency that improves isopropyl benzene and hydrogen phosphide cumene, as U.S. Pat 6291718, all mentioned among the US6476276 in the oxidation of alkylbenzene and to have added a kind of special compound that can Mulberry Extract.In the mixture of 144g isopropyl benzene and 36g isopropyl benzene hydroperoxide, add 2,2,6 of 18mg, 6-tetramethyl piperidine oxide compound, all these joins 0.05% the Na of 90g
2CO
3In the aqueous solution, react after 3 hours, the selectivity of isopropyl benzene hydroperoxide is 91mol%.As mentioning with alkali ionic liquid in Chinese patent 200810102379.1 is catalyst oxidation isopropyl benzene and diisopropylbenzene(DIPB), can improve the transformation efficiency of diisopropylbenzene(DIPB) significantly and to the selectivity of hydrogen peroxide product.
Summary of the invention
Purpose of the present invention is reduced into the link of benzylalcohol with hydrogen phosphide cumene in the DCP production process, and a kind of preparation method who is used to produce the raw material of DCP is provided, and the direct condensation of gained mixture of the present invention can be generated DCP.
For achieving the above object, technical scheme of the present invention: the mixture that adopts alkali ionic liquid and yellow soda ash as oxygen source, is made isopropyl benzene the mixture of hydrogen phosphide cumene and dimethyl benzyl alcohol with air as catalyzer 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 the following 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 inequality.
The known art methods preparation that the used alkali ionic liquid of the present invention adopts those skilled in the art to know.
The mass ratio of described alkali ionic liquid and yellow soda ash is 1-100: 1.
Add ion liquid quality in the catalytic oxidation process and be 0.001～1 times of isopropyl benzene, be preferably: 0.002～0.5 times.
The temperature of reaction of catalyzed oxidation is 60～150 ℃, and air flow quantity is 25～120L/ (a 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, when having improved THE AUTOXIDATION OF CUMENE speed, 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 near 1: 1 mixture, avoided in the DCP production process hydrogen phosphide cumene being reduced into the link of benzylalcohol, the direct condensation of this mixture can generate DCP.Can directly carry out condensation and obtain DCP, save the reduction step in the 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 separates with reactant flow easily simultaneously, has reduced the shadow to subsequent technique.
Description of drawings
Fig. 1 isopropyl benzene prepares the reaction process of DCP.
Embodiment
Comparative Examples 1
Comparative Examples 1 is the base catalysis method for oxidation that adopts usually.
Getting the 15g isopropyl benzene is put in the there-necked flask of taking back stream device, stirring, add the mass percentage concentration 1.5gNaOH aqueous solution (mass concentration 2%), 90 ℃ of temperature of reaction, bubbling 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 of taking back stream device, stirring, add 0.08g hydroxide 1-methyl, the 3-butyl imidazole, 0.02g yellow soda ash, 60 ℃ of temperature of reaction, bubbling 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 of taking back stream device, stirring, add 0.1g hydroxide 1-methyl, 3-hexyl imidazoles, 0.1g yellow soda ash, 90 ℃ of temperature of reaction, bubbling air 150ml/min reacts after 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 of taking back stream device, stirring, add 6.69g hydroxide butyl-pyridinium, 1.02g yellow soda ash, 90 ℃ of temperature of reaction, bubbling air 150ml/min reacts after 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 of taking back stream device, stirring, add the 1.54g tetraethyl ammonium hydroxide, 0.62g 100 ℃ of yellow soda ash temperature of reaction, bubbling 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 of taking back stream device, stirring, add 0.07g hydroxide 1-methyl 3-ethyl imidazol(e), 0.02g yellow soda ash, 105 ℃ of temperature of reaction, bubbling air 100ml/min reacted after 20 hours, and 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 of taking back stream device, stirring, add 2.00g hydroxide 1-methyl 3-octadecyl imidazoles, 0.02g yellow soda ash, 100 ℃ of temperature of reaction, bubbling air 100ml/min reacted after 16 hours, and 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 (7)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100596726A CN102199114B (en) | 2011-03-11 | 2011-03-11 | Method for preparing raw material for producing dicumyl peroxide |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100596726A CN102199114B (en) | 2011-03-11 | 2011-03-11 | Method for preparing raw material for producing dicumyl peroxide |
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| Publication Number | Publication Date |
|---|---|
| CN102199114A true CN102199114A (en) | 2011-09-28 |
| CN102199114B CN102199114B (en) | 2013-12-04 |
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|---|---|---|---|
| CN2011100596726A Expired - Fee Related CN102199114B (en) | 2011-03-11 | 2011-03-11 | Method for preparing raw material for producing dicumyl peroxide |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104860861A (en) * | 2015-04-01 | 2015-08-26 | 中石化上海工程有限公司 | Production method for dicumyl peroxide (DCP) |
| CN115403446A (en) * | 2022-09-01 | 2022-11-29 | 山东阳谷华泰化工股份有限公司 | Synthetic method of alpha, alpha' -dihydroxy-1, 3-diisopropylbenzene |
| CN119707768A (en) * | 2024-12-30 | 2025-03-28 | 常州瑞华化工工程技术股份有限公司 | Isobutane oxidation method and system |
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 (2)
| Title |
|---|
| 吴俊荣等: "《异丙苯氧化的研究进展 》", 《广州化工》 * |
| 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》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104860861A (en) * | 2015-04-01 | 2015-08-26 | 中石化上海工程有限公司 | Production method for dicumyl peroxide (DCP) |
| CN115403446A (en) * | 2022-09-01 | 2022-11-29 | 山东阳谷华泰化工股份有限公司 | Synthetic method of alpha, alpha' -dihydroxy-1, 3-diisopropylbenzene |
| 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 |
| CN119707768A (en) * | 2024-12-30 | 2025-03-28 | 常州瑞华化工工程技术股份有限公司 | Isobutane oxidation method and system |
| CN119707768B (en) * | 2024-12-30 | 2025-07-01 | 常州瑞华化工工程技术股份有限公司 | Isobutane oxidation method and system |
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