CN1308273C - Process for preparing isopropyl benzene by catalytically hydrogenolysis alpha, alpha dimethyl benzyl alcohol - Google Patents
Process for preparing isopropyl benzene by catalytically hydrogenolysis alpha, alpha dimethyl benzyl alcohol Download PDFInfo
- Publication number
- CN1308273C CN1308273C CNB2004100667026A CN200410066702A CN1308273C CN 1308273 C CN1308273 C CN 1308273C CN B2004100667026 A CNB2004100667026 A CN B2004100667026A CN 200410066702 A CN200410066702 A CN 200410066702A CN 1308273 C CN1308273 C CN 1308273C
- Authority
- CN
- China
- Prior art keywords
- alpha
- reaction
- hydrogen
- hydrogenolysis
- 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.)
- Expired - Fee Related
Links
Abstract
The present invention discloses a method for preparing cumene through the catalysis and the hydrogenolysis of alpha, alpha-dimethyl benzyl alcohol. The present invention uses hydrogen gas or organic compounds as a hydrogen source, alpha, alpha-dimethyl benzyl alcohol in solvent is decomposed into cumene in a hydrogen mode under the action of a multi-phase palladium group catalyst, reaction temperature is from 30 to 100 DGE C, the conversion rate of alpha, alpha-dimethyl benzyl alcohol is larger than 96%, and the selectivity of cumene is larger than 99%. The method can be applied to the hydrogenolysis that cumene hydroperoxide is used as an oxidizing agent, alpha-dimethyl benzyl alcohol as co-products generated in the process of the preparation of epoxy propane by the epoxidation of propene, and thereby, the recycle of cumene is realized. One hand, propene in tail gas generated in the process of the production of chloropropene or polypropylene can be recovered by the technique, energy sources are saved, and pollution to the atmosphere is reduced; one the other hand, the technique can be used for building production plants for producing epoxy propane by the epoxidation of propene.
Description
Technical field
The present invention relates to a kind of preparation method of isopropyl benzene, particularly a kind of catalytic hydrogenolysis α, the alpha-alpha-dimethyl phenylcarbinol prepares the method for isopropyl benzene.
Background technology
Isopropyl benzene is important Organic Chemicals, can be used for preparing phenol, acetone, also can be used as the super-gasoline component to improve the quality of gasoline.
Propylene oxide (PO) also is important basic Organic Chemicals, and industrial main employing chlorohydrination and Halcon method (indirect oxidation method) are produced at present.The Halcon method is that the employing organo-peroxide is an oxygenant, and epoxidation propylene gets propylene oxide, and has a large amount of joint product to generate.If be oxygenant epoxidation propylene system propylene oxide with the hydrogen phosphide cumene, its joint product are α, and the alpha-alpha-dimethyl phenylcarbinol can generate isopropyl benzene by catalytic hydrogenolysis, and the raw materials for production that can be used as hydrogen phosphide cumene then recycle.Therefore, in the technological process for oxygenant epoxidation propylene system propylene oxide, can directly utilize the raw material hydrogen phosphide cumene of producing phenol in the petroleum chemical plant to be the oxidant production propylene oxide with the hydrogen phosphide cumene.Can avoid the generation of joint product and build the device of producing oxygenant again.
The patent of sumitomo chemical company provides α, and alpha-alpha-dimethyl phenylcarbinol catalytic hydrogenolysis is produced the technological process of isopropyl benzene, the technology of reporting as following document and patent:
Tsuji，Junpei；Omae，Toshikazu(Sumitomo Chemical Co.，Ltd.，Japan).Patent number：EP1266891，Publication date：2002-12-18
Seo，Takeo；Tsuji，Junpei(Sumitomo Chemical Co.，Ltd.，Japan).Patentnumber：EP1266894，Publication date：2002-12-18
Tsuji，Junpei；Oku，Noriaki(Sumitomo Chemical Co.，Ltd.，Japan).Jpn.Kokai Tokkyo Koho JP 2003081886 A2 19 Mar 2003，3 pp.(Japanese).(Japan).APPLICATION：JP 2001-277701 13 Sep 2001.
Tsuji，Junpei；Ishino，Masaru(Sumitomo Chemical Co.，Ltd.，Japan).Jpn.Kokai Tokkyo Koho JP 2003081887 A2 19 Mar 2003，3 pp.(Japanese).(Japan).APPLICATION：JP 2001-277702 13 Sep 2001.
Tsuji，Junpei；Oku，Nobuaki(Sumitomo Chemical Co.，Ltd.，Japan).Jpn.Kokai Tokkyo Koho JP 2003081888 A2 19 Mar 2003，4 pp.(Japanese).(Japan).APPLICATION：JP 2001-277700 13 Sep 2001。
The technology of above-mentioned bibliographical information is a hydrogen source with hydrogen, and the copper chromated oxide is a catalyzer, though α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol almost reaches 100%, the selectivity 97.5% of isopropyl benzene.But reaction needs to carry out under higher temperature (180 ℃), and there is environmental pollution problems in the copper chromium oxide catalyst.
Summary of the invention
The technical issues that need to address of the present invention are to disclose a kind of catalytic hydrogenolysis α, and the alpha-alpha-dimethyl phenylcarbinol prepares the method for isopropyl benzene, to overcome the defective that prior art exists.
Method of the present invention comprises the steps:
With hydrogen source under the effect of heterogeneous palladium-based catalyst with solvent in α, alpha-alpha-dimethyl phenylcarbinol reaction, temperature of reaction is 30-100 ℃, with catalyst separating, removes and promptly obtains isopropyl benzene after desolvating after reaction finishes.
Said hydrogen source comprises hydrogen or HCOOH, HCOOLi, HCOONa, HCOOK, HCOONH
4, tetrahydrobenzene, HCOONHEt
3, one or more the aqueous solution in indoline, tetrahydroquinoline, methyl alcohol, ethanol, 2-propyl alcohol or the sodium hypophosphite;
According to optimized technical scheme of the present invention, when being hydrogen source with hydrogen, temperature of reaction is 30-100 ℃, reaction pressure 100-300kPa;
The component of said heterogeneous palladium-based catalyst and weight concentration are: the Pd of 0.3-5%wt, the gac of 95-99.7%wt, catalyzer employing document (A.B. department ladder is reined in this. Catalyst Production-laboratory and industrial preparation. and Shanghai: Huadong Chemical College press, dipping-precipitator method of describing 1991:131) are prepared, and carrier is the cocoanut active charcoal that steam treatment is crossed;
Said solvent is selected from unit alcohol or the polyvalent alcohol of C1-C6;
HCOOH, HCOOLi, HCOONa, HCOOK, HCOONH
4, tetrahydrobenzene, HCOONHEt
3, indoline, tetrahydroquinoline, methyl alcohol, ethanol, 2-propyl alcohol or sodium hypophosphite the volumetric concentration of the aqueous solution be 10
-2-100%, add-on is with α, and the weight of alpha-alpha-dimethyl phenylcarbinol is counted 20-150%wt;
α in the solvent, the weight concentration of alpha-alpha-dimethyl phenylcarbinol is 1-20wt%;
According to optimized technical scheme of the present invention, with hydrogen is the α of hydrogen source hydrogenolysis in containing the reaction solution of superoxide, during the alpha-alpha-dimethyl phenylcarbinol, should add halogenated aryl hydrocarbon in the reaction system, to improve the productive rate of isopropyl benzene, the add-on of halogenated aryl hydrocarbon is with α, and the weight of alpha-alpha-dimethyl phenylcarbinol is counted 1-80%wt, and halogenated aryl hydrocarbon is selected from a kind of in chlorobenzene, bromobenzene or the iodobenzene etc.;
Advantage of the present invention is to adopt high performance heterogeneous palladium-based catalyst, can adopt different hydrogen source catalytic hydrogenolysis α, and the alpha-alpha-dimethyl phenylcarbinol prepares isopropyl benzene, the reaction conditions gentleness, and whole process can not pollute environment.If with the organic compound is hydrogen source, be reflected under the normal pressure and carry out, operate simpler.This method can be applicable to be the joint product α that produces in the oxygenant epoxidation propylene system propylene oxide process with the hydrogen phosphide cumene that the hydrogenolysis of alpha-alpha-dimethyl phenylcarbinol makes the isopropyl benzene cycling and reutilization.Adopt present method, α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol can be greater than 96%, and the selectivity of isopropyl benzene can be greater than 99%.
Embodiment
Embodiment 1
Get α, alpha-alpha-dimethyl phenylcarbinol 0.2g, 2%wtPd/C catalyzer 0.1g, (formic acid: 5ml water=3: 12), 10ml ethanol is solvent to formic acid solution, joins in the ground Erlenmeyer flask, is heated to 60 ℃ under stirring and refluxes 4 hours.After finishing, reaction, reaction mixture is carried out stratographic analysis with marker method with the catalyzer centrifugation.α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol are 96%, and the selectivity of isopropyl benzene is 99%.
Embodiment 2
Get α, alpha-alpha-dimethyl phenylcarbinol 0.2g, 2%wtPd/C catalyzer 0.1g, 2-propanol solution 5ml, the 10ml trimethyl carbinol is a solvent, joins in the ground Erlenmeyer flask, is heated to 60 ℃ under stirring and refluxes 4 hours.After finishing, reaction, reaction mixture is carried out stratographic analysis with marker method with the catalyzer centrifugation.α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol are 6.4%, and the selectivity of isopropyl benzene is 65.8%.
Embodiment 3
Get α, alpha-alpha-dimethyl phenylcarbinol 0.2g, 2%wtPd/C catalyzer 0.02g, acetate 5ml, 10ml ethanol is solvent, joins in the stainless steel cauldron of 0.15L, feeds hydrogen in still, treat that pressure reaches behind the 250kPa oil bath of reactor being put into 30 ℃ and heats, under agitation catalytic hydrogenolysis is 2 hours.After finishing, reaction, reaction mixture is carried out stratographic analysis with marker method with the catalyzer centrifugation.α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol are 98%, and the selectivity of isopropyl benzene is 99%.
Embodiment 4
Get α, alpha-alpha-dimethyl phenylcarbinol 0.2g, 2%wtPd/C catalyzer 0.02g, acetate 5ml, the 10ml tetrahydrofuran (THF) is a solvent, joins in the stainless steel cauldron of 0.15L, feeds hydrogen in still, treat that pressure reaches behind the 250kPa oil bath of reactor being put into 30 ℃ and heats, under agitation catalytic hydrogenolysis is 2 hours.After finishing, reaction, reaction mixture is carried out stratographic analysis with marker method with the catalyzer centrifugation.α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol are 96%, and the selectivity of isopropyl benzene is 97%.
Embodiment 5
Get α, alpha-alpha-dimethyl phenylcarbinol 0.2g, 2%wtPd/C catalyzer 0.02g, acetate 5ml, 10ml ethanol is solvent, joins in the stainless steel cauldron of 0.15L, in still, feed hydrogen, after treating that pressure reaches 150kPa, reactor put into 60 ℃ oil bath and heat, under agitation catalytic hydrogenolysis is 2 hours.After finishing, reaction, reaction mixture is carried out stratographic analysis with marker method with the catalyzer centrifugation.α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol are 90%, and the selectivity of isopropyl benzene is 98%.
Embodiment 6
Get α, alpha-alpha-dimethyl phenylcarbinol 0.2g, 0.5%wtPd/C catalyzer 0.02g, acetate 5ml, 10ml ethanol is solvent, joins in the stainless steel cauldron of 0.15L, in still, feed hydrogen, after treating that pressure reaches 250kPa, reactor put into 60 ℃ oil bath and heat, under agitation catalytic hydrogenolysis is 2 hours.After finishing, reaction, reaction mixture is carried out stratographic analysis with marker method with the catalyzer centrifugation.α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol are 70%, and the selectivity of isopropyl benzene is 97%.
Embodiment 7
Get α, alpha-alpha-dimethyl phenylcarbinol 0.2g, 5%wtPd/C catalyzer 0.02g, acetate 5ml, 10ml ethanol is solvent, joins in the stainless steel cauldron of 0.15L, feeds hydrogen in still, treat that pressure reaches behind the 150kPa oil bath of reactor being put into 60 ℃ and heats, under agitation catalytic hydrogenolysis is 2 hours.After finishing, reaction, reaction mixture is carried out stratographic analysis with marker method with the catalyzer centrifugation.α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol are 98%, and the selectivity of isopropyl benzene is 99%.
Embodiment 8
Get product 1 after the 0.9g propylene ring oxidation reaction (essential substance form see attached list), 2%wtPd/C catalyzer 0.1g, and formic acid solution (formic acid: 5ml water=3: 12), 10ml ethanol is solvent, join in the ground Erlenmeyer flask, under agitation be heated to 60 ℃ after backflow hydrogenolysis 8 hours.After finishing, reaction, reaction mixture is carried out stratographic analysis with marker method with the catalyzer centrifugation.α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol are 85%, and the selectivity of isopropyl benzene is 91%.
Embodiment 9
Get the product 1 after the 0.9g propylene ring oxidation reaction, 2%wtPd/C catalyzer 0.1g, glacial acetic acid 5ml, 10ml ethanol is solvent, join in the stainless steel cauldron of 0.15L, in still, feed hydrogen, treat that pressure reaches 250kPa after, the oil bath that reactor is put into 80 ℃ is heated, and under agitation hydrogenolysis is 6 hours.After finishing, reaction, reaction mixture is carried out stratographic analysis with marker method with the catalyzer centrifugation.α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol are 45%, and the selectivity of isopropyl benzene is 90%.
Embodiment 10
Get the product 1 after the 0.9g propylene ring oxidation reaction, 2%wtPd/C catalyzer 0.1g, glacial acetic acid 5ml, chlorobenzene 0.15ml, 10ml ethanol is solvent, joins in the stainless steel cauldron of 0.15L, in still, feed hydrogen, after treating that pressure reaches 250kPa, reactor put into 60 ℃ oil bath and heat, under agitation hydrogenolysis is 4 hours.After finishing, reaction, reaction mixture is carried out stratographic analysis with marker method with the catalyzer centrifugation.α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol are 94%, and the selectivity of isopropyl benzene is 97%.
Embodiment 11
Get product 2 after the 8.0g propylene ring oxidation reaction (essential substance form see attached list), 2%wtPd/C catalyzer 0.1g, glacial acetic acid 5ml, 10ml ethanol is solvent, join in the stainless steel cauldron of 0.15L, in still, feed hydrogen, treat that pressure reaches 250kPa after, reactor put into 60 oil bath and heat, under agitation hydrogenolysis is 4 hours.After finishing, reaction, reaction mixture is carried out stratographic analysis with marker method with the catalyzer centrifugation.α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol are 85%, and the selectivity of isopropyl benzene is 97%.
Embodiment 12
Get product 3 after the 2.1g propylene ring oxidation reaction (essential substance form see attached list), 2%wtPd/C catalyzer 0.1g, glacial acetic acid 5ml, 10ml. ethanol is solvent, join in the stainless steel cauldron of 0.15L, in still, feed hydrogen, treat that pressure reaches 250kPa after, reactor put into 60 oil bath and heat, under agitation hydrogenolysis is 6 hours.After finishing, reaction, reaction mixture is carried out stratographic analysis with marker method with the catalyzer centrifugation.α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol are 82%, and the selectivity of isopropyl benzene is 93%.
Subordinate list: the essential substance of propylene ring oxidation reaction after product is formed
| The material title | Essential substance is formed (mass ratio) (isopropyl benzene: alpha-methyl styrene: α, alpha-alpha-dimethyl phenylcarbinol: hydrogen phosphide cumene) |
| Epoxy product 1 epoxy product 2 epoxy products 3 | 78.9∶1.0∶17.8∶2.3 96.0∶2.0∶2.0∶0 2.9∶69.1∶28.0∶0 |
Comparative Examples 1
Get α, alpha-alpha-dimethyl phenylcarbinol 0.2g, 2%wtPd/ γ-Al
2O
3Catalyzer 0.02g, acetate 5ml, 10ml ethanol is solvent, joins in the stainless steel cauldron of 0.15L, feeds hydrogen in still, treat that pressure reaches 250kPa after, reactor put into 60 ℃ oil bath and heats, under agitation hydrogenolysis is 2 hours.After finishing, reaction, reaction mixture is carried out stratographic analysis with marker method with the catalyzer centrifugation.α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol are 26%, and the selectivity of isopropyl benzene is 87%.
Comparative Examples 2
Get α, alpha-alpha-dimethyl phenylcarbinol 0.2g, 2%wtPd/MCM-41 catalyzer 0.02g, acetate 5ml, 10ml ethanol is solvent, joins in the stainless steel cauldron of 0.15L, in still, feed hydrogen, after treating that pressure reaches 250kPa, reactor put into 60 ℃ oil bath and heat, under agitation hydrogenolysis is 2 hours.After finishing, reaction, reaction mixture is carried out stratographic analysis with marker method with the catalyzer centrifugation.α, the transformation efficiency of alpha-alpha-dimethyl phenylcarbinol are 22%, and the selectivity of isopropyl benzene is 83%.
Claims (8)
1. catalytic hydrogenolysis α, the alpha-alpha-dimethyl phenylcarbinol prepares the method for isopropyl benzene, it is characterized in that, comprises the steps:
With hydrogen source in the presence of heterogeneous palladium-based catalyst with solvent in α, alpha-alpha-dimethyl phenylcarbinol reaction, temperature of reaction is 30-100 ℃, reaction finishes catalyst separating, removes promptly to obtain isopropyl benzene after desolvating;
Said hydrogen source comprises one or more the aqueous solution in hydrogen or HCOOH, HCOOLi, HCOONa, HCOOK, HCOONH4, tetrahydrobenzene, HCOONHEt3, indoline, tetrahydroquinoline, methyl alcohol, ethanol, 2-propyl alcohol or the sodium hypophosphite;
The component and the weight concentration of said heterogeneous palladium-based catalyst comprise: the Pd of 0.3-5%, the gac of 95-99.7%.
2. method according to claim 1 is characterized in that, said solvent is selected from unit alcohol or the polyvalent alcohol of C1-C6.
3. method according to claim 1, it is characterized in that the volumetric concentration of the aqueous solution of HCOOH, HCOOLi, HCOONa, HCOOK, HCOONH4, tetrahydrobenzene, HCOONHEt3, indoline, tetrahydroquinoline, methyl alcohol, ethanol, 2-propyl alcohol or sodium hypophosphite is 10
-2-100%.
4. method according to claim 3, it is characterized in that, the add-on of the aqueous solution of HCOOH, HCOOLi, HCOONa, HCOOK, HCOONH4, tetrahydrobenzene, HCOONHEt3, indoline, tetrahydroquinoline, methyl alcohol, ethanol, 2-propyl alcohol or sodium hypophosphite is with α, and the weight of alpha-alpha-dimethyl phenylcarbinol is counted 20-150%.
5. method according to claim 1 is characterized in that, α in the solvent, and the weight concentration of alpha-alpha-dimethyl phenylcarbinol is 1-20%.
6. method according to claim 1 is characterized in that, is the α of hydrogen source hydrogenolysis in reaction solution with hydrogen, during the alpha-alpha-dimethyl phenylcarbinol, adds halogenated aryl hydrocarbon in the reaction system.
7. method according to claim 6 is characterized in that, the add-on of halogenated aryl hydrocarbon is with α, and the weight of alpha-alpha-dimethyl phenylcarbinol is counted 1-80%, and halogenated aryl hydrocarbon is selected from a kind of in chlorobenzene, bromobenzene or the iodobenzene.
8. method according to claim 1 is characterized in that, when being hydrogen source with hydrogen, temperature of reaction is 30-100 ℃, reaction pressure 100-300kPa.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100667026A CN1308273C (en) | 2004-09-27 | 2004-09-27 | Process for preparing isopropyl benzene by catalytically hydrogenolysis alpha, alpha dimethyl benzyl alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100667026A CN1308273C (en) | 2004-09-27 | 2004-09-27 | Process for preparing isopropyl benzene by catalytically hydrogenolysis alpha, alpha dimethyl benzyl alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1616383A CN1616383A (en) | 2005-05-18 |
| CN1308273C true CN1308273C (en) | 2007-04-04 |
Family
ID=34764935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100667026A Expired - Fee Related CN1308273C (en) | 2004-09-27 | 2004-09-27 | Process for preparing isopropyl benzene by catalytically hydrogenolysis alpha, alpha dimethyl benzyl alcohol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1308273C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101735004B (en) * | 2008-11-21 | 2012-05-23 | 中国石油化工股份有限公司 | Method for producing isopropylbenzene by hydrogenolysis of alpha, alpha-dimethyl benzyl alcohol |
| CN101768044B (en) * | 2009-01-07 | 2013-05-08 | 中国石油化工股份有限公司 | Method for producing isopropyl benzene |
| WO2023108336A1 (en) | 2021-12-13 | 2023-06-22 | 万华化学集团股份有限公司 | Dimethyl benzyl alcohol hydrogenolysis catalyst, and preparation method therefor and use thereof |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104230856B (en) * | 2013-06-17 | 2016-06-08 | 中国石油化工股份有限公司 | The production method of butylene oxide ring |
| CN110563532A (en) * | 2018-09-11 | 2019-12-13 | 深圳大学 | Method for constructing carbon-hydrogen bond by dehydroxylation of alcohol under catalysis of palladium/platinum |
| EP3984984A4 (en) * | 2019-08-09 | 2023-07-19 | Sumitomo Chemical Company, Limited | Method for producing cumene |
| CN113121298B (en) * | 2019-12-31 | 2023-05-02 | 中国石油化工股份有限公司 | Method for producing isopropyl benzene |
| CN113070060B (en) * | 2020-01-03 | 2022-08-05 | 万华化学集团股份有限公司 | Catalyst for preparing isopropylbenzene by hydrogenolysis of alpha-dimethyl benzyl alcohol and preparation method and application thereof |
| CN113651664A (en) * | 2020-05-12 | 2021-11-16 | 中国石油化工股份有限公司 | Method for conversion of benzyl alcohol |
| CN112044466A (en) * | 2020-07-29 | 2020-12-08 | 华东理工大学 | Method for preparing high-value aromatic hydrocarbon by aromatization of MTP (methanol to propylene) byproduct |
| CN115385768A (en) * | 2021-05-19 | 2022-11-25 | 中国石油化工股份有限公司 | Preparation method of cumene, preparation method of propylene oxide and obtained cumene and propylene oxide |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3793369A (en) * | 1971-10-22 | 1974-02-19 | Toray Industries | Process for production of carboxylic esters |
| US5569802A (en) * | 1992-06-27 | 1996-10-29 | Huels Aktiengesellschaft | Catalyst, process for the preparation thereof and process for the selective hydrogenation of unsaturated compounds |
| CN1155450A (en) * | 1996-01-25 | 1997-07-30 | 中国石油化工总公司 | Alkylated catalyst for preparation of alkylbenzene |
| CN1553886A (en) * | 2001-09-13 | 2004-12-08 | ס�ѻ�ѧ��ҵ��ʽ���� | Process for producing cumene |
-
2004
- 2004-09-27 CN CNB2004100667026A patent/CN1308273C/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3793369A (en) * | 1971-10-22 | 1974-02-19 | Toray Industries | Process for production of carboxylic esters |
| US5569802A (en) * | 1992-06-27 | 1996-10-29 | Huels Aktiengesellschaft | Catalyst, process for the preparation thereof and process for the selective hydrogenation of unsaturated compounds |
| CN1155450A (en) * | 1996-01-25 | 1997-07-30 | 中国石油化工总公司 | Alkylated catalyst for preparation of alkylbenzene |
| CN1553886A (en) * | 2001-09-13 | 2004-12-08 | ס�ѻ�ѧ��ҵ��ʽ���� | Process for producing cumene |
Non-Patent Citations (1)
| Title |
|---|
| 溢流床反应器AMS加氢合成异丙苯 李秋先，东北师大学报自然科学版，第35卷第2期 2003 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101735004B (en) * | 2008-11-21 | 2012-05-23 | 中国石油化工股份有限公司 | Method for producing isopropylbenzene by hydrogenolysis of alpha, alpha-dimethyl benzyl alcohol |
| CN101768044B (en) * | 2009-01-07 | 2013-05-08 | 中国石油化工股份有限公司 | Method for producing isopropyl benzene |
| WO2023108336A1 (en) | 2021-12-13 | 2023-06-22 | 万华化学集团股份有限公司 | Dimethyl benzyl alcohol hydrogenolysis catalyst, and preparation method therefor and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1616383A (en) | 2005-05-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1308273C (en) | Process for preparing isopropyl benzene by catalytically hydrogenolysis alpha, alpha dimethyl benzyl alcohol | |
| CN1092173C (en) | Process for making 2,3-dihalopropanols | |
| US9382225B2 (en) | Reduction of C—O bonds by catalytic transfer hydrogenolysis | |
| CN1160300C (en) | Process for preparation of acetic acid product comprising | |
| CN1720208A (en) | Process for producing alcohol | |
| EA025024B1 (en) | Solid base catalyst | |
| CN1847206A (en) | Synthesis process of cyclohexanone and cyclohexanol | |
| CN101073783A (en) | Solid-loaded ionic-liquid catalyst for olefin-dihydroxy reaction, its production and use | |
| CN101037439A (en) | Production technique of benzenetetracarboxylic dianhydride by catalyzing carrier-type polyoxometalates | |
| CN1587244A (en) | Process for producing isononyl aldehyde from mixed octene and synthetic gas | |
| CN112961123B (en) | Method for preparing 3- (2-furyl) -2-methyl-2-acrolein by catalyzing oxidation condensation of furfural and n-propanol | |
| CN1054316C (en) | New method and catalysts on inorganic carriers for converting C1-C4 Hydrocarbons to C2-olefinic hydrocarbons | |
| CN107253904B (en) | Lignin degradation method | |
| CN1204970C (en) | Reaction control phase transferring catalyst for oxidizing reaction and its oxidizing reaction process | |
| CN1161346C (en) | Process for preparing epoxy cyclohexane by catalytic cyclooxidation of cyclohexene | |
| CN102863389A (en) | Method for synthesizing benzimidazole compound | |
| JP2010215473A (en) | Method for producing molded article of sulfonic acid group-containing carbonaceous material and application of the same | |
| CN1171399A (en) | Process of preparation of epoxides from olefins | |
| CN1285554C (en) | Process for producing alkylene glycol | |
| Vivien et al. | MnBr (CO) 5: a commercially available highly active catalyst for olefin hydrosilylation under ambient air and green conditions | |
| CN101613328B (en) | Method for preparing alpha, beta-unsaturated ketone epoxy compound | |
| CN1769254A (en) | Method for synthesizing alkynol by ketone and acetylene | |
| CN113275038A (en) | Method for photocatalytic oxidative cracking of lignin C-O bond and benzene ring | |
| Ukisu | Pd-catalyzed transfer hydrogenolysis of benzylic alcohol in acidic 2-propanol | |
| CN1721384A (en) | Process for producing alkylene glycol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20070404 Termination date: 20160927 |