CN101992098A - Copper catalyst for preparing isopropyl benzene by alpha, alpha-dimethyl benzyl alcohol hydrogenolysis and preparation method thereof - Google Patents
Copper catalyst for preparing isopropyl benzene by alpha, alpha-dimethyl benzyl alcohol hydrogenolysis and preparation method thereof Download PDFInfo
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- CN101992098A CN101992098A CN2009100578152A CN200910057815A CN101992098A CN 101992098 A CN101992098 A CN 101992098A CN 2009100578152 A CN2009100578152 A CN 2009100578152A CN 200910057815 A CN200910057815 A CN 200910057815A CN 101992098 A CN101992098 A CN 101992098A
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Abstract
The invention relates to a copper catalyst for preparing isopropyl benzene by alpha, alpha-dimethyl benzyl alcohol hydrogenolysis and a preparation method thereof, and mainly solves the problem of poor stability of the Cu catalyst prepared in the prior art. The invention well solves the problem by adopting the technical schemes of the catalyst and the preparation method thereof, wherein the catalyst comprises the following components in percentage by weight: 20.0 to 55.0 percent of CuO, 15.0 to 50.0 percent of ZnO, 10.0 to 45.0 percent of Al2O3 and 1.0 to 20.0 percent of at least one of MnO2, TiO2 and ZrO2; and the catalyst can be used in the industrial production of producing the isopropyl benzene by the alpha, alpha-dimethyl benzyl alcohol hydrogenolysis.
Description
Technical field
The present invention relates to a kind of α, copper catalyst of alpha-alpha-dimethyl benzylalcohol hydrogenolysis preparing isopropylbenzene and preparation method thereof.
Background technology
Expoxy propane is a kind of important petrochemical industry Organic Ingredients.At present, the main production method of expoxy propane is chlorohydrination and ethylbenzene hydroperoxide method.The ethylbenzene hydroperoxide method is that employing ethylbenzene peroxide is that oxidant is an expoxy propane with propylene oxidation.Though this process can avoid investing the advantage of the chlorohydrination of high and long flow path to the severe contamination of environment, but a shortcoming is arranged also, have a large amount of coproduction accessory substances-styrene in the process and generate, thereby make the production cost of the expoxy propane of this technology path can be because of the influence of the price fluctuation of co-product.And be oxygen source with the hydrogen phosphide cumene, also oxidable production of propylene expoxy propane.This process co-product is α, and alpha-alpha-dimethyl benzylalcohol can generate isopropylbenzene by catalytic hydrogenolytic cleavage.Isopropylbenzene can return the peroxidating unit process and obtain hydrogen phosphide cumene.With the technology ratio of ethylbenzene hydroperoxide method oxidation production expoxy propane, this process has advantages such as process route is short, and equipment investment is few, and no co-product and production prices are more stable.
U.S. Pat 6646139B2 has disclosed α, and alpha-alpha-dimethyl benzylalcohol catalytic hydrogenolysis prepares the technical process of isopropylbenzene, and this technology is to be hydrogen source with hydrogen, is catalyst with the Cu-Cr oxide.Though α, the conversion ratio of alpha-alpha-dimethyl benzylalcohol reaches 100%, and selectivity surpasses 97.5%, not mentioned its stable index of this catalyst.
Chinese patent CN1257138C has proposed to use H
2Method with CO gaseous mixture reduction Cu catalyst because its catalyst system therefor remains the Cu-Cr catalyst, does not disclose its stable index in this patent.
The activated centre of copper base hydrogenation catalyst is the metallic copper crystal grain that obtains after the activation under the hydrogen atmosphere.Because the fusing point of metallic copper is lower, makes copper catalyst in being applied to the bigger hydrogenation process of thermal discharge, the phenomenon with sintering of growing up of copper crystal grain usually can take place.Growing up and sintering of copper crystal grain is with the reduction that directly causes the minimizing of activity of such catalysts bits number with catalyst activity.Simultaneously, the decline of hydrogenation activity can be brought out side reaction such as polymerization and take place, and causes the activity of such catalysts position to be aggregated that accessory substance covers and the carrier duct is aggregated thing and stops up, thereby has caused the reduction and the stable decline of catalyst activity.
In sum, the Cu catalyst with prior art for preparing is applied to α, and alpha-alpha-dimethyl benzylalcohol catalytic hydrogenolysis prepares in the isopropylbenzene process, has the problem of poor catalyst stability.
Summary of the invention
One of technical problem to be solved by this invention is, the copper catalyst of prior art for preparing is applied to α, there is the problem of poor stability in alpha-alpha-dimethyl benzylalcohol hydrogenation when producing isopropylbenzene, provide a kind of new α, the copper catalyst of alpha-alpha-dimethyl benzylalcohol producing isopropylbenzene by hydrogenolysis.This catalyst is used for α, in the alpha-alpha-dimethyl benzylalcohol hydrogenolysis preparing isopropylbenzene process, has the advantage of good stability.Two of technical problem solved by the invention provides the Preparation of catalysts method that the related copper catalyst of one of a kind of and technical solution problem adapts.
For one of solving the problems of the technologies described above, the technical solution used in the present invention is as follows: a kind of α, and the copper catalyst of alpha-alpha-dimethyl benzylalcohol hydrogenolysis preparing isopropylbenzene comprises following component by weight percentage:
a)20.0～55.0％CuO；
b)15.0～50.0％ZnO；
c)10.0～45.0％Al
2O
3；
D) 1.0～20.0% auxiliary agents are selected from MnO
2, TiO
2Or ZrO
2In at least a.
In the technique scheme, by weight percentage, the preferable range of CuO consumption is 25.0～45.0%; The preferable range of ZnO consumption is 20.0～40.0%; Al
2O
3The preferable range of consumption is 15.0～40.0%; Be selected from MnO
2, TiO
2Or ZrO
2In at least a consumption preferable range be 1.0～15.0%, more preferably scheme is d) component is selected from MnO
2And TiO
2Or ZrO
2In at least a mixture, by weight percentage, MnO wherein
2Consumption be 0.5～5.0%, be selected from TiO
2Or ZrO
2In at least a consumption be 2.0～14.5%.
For solve the problems of the technologies described above two, the technical solution used in the present invention is as follows: a kind of α, the preparation method of the copper catalyst of alpha-alpha-dimethyl benzylalcohol hydrogenolysis preparing isopropylbenzene may further comprise the steps: 1) aluminium oxide of aequum is mixed making beating with water and obtain slurries I; 2) with Cu, the Zn of aequum and be selected from the mixed solution of at least a salt among Mn, Ti or the Zr and the aqueous solution of sodium carbonate splashes into simultaneously and carries out co-precipitation among the slurries I, the precipitation temperature preferable range is 70～90 ℃, pH value of solution value preferable range is 6.5～8.5, through aging, washing, dry and 300～500 ℃ of roastings after 0.5～8 hour, mixes afterwards to obtain catalyst behind the compression molding with graphite, the water of aequum.The consumption of graphite counts 1～3% with the baked solid percentage by weight, and the consumption of water is 10～30%.The catalyst of gained before use, in order to the 5%H of volumn concentration meter
2-95%N
2Gaseous mixture is used for hydrogenolysis in reduction under 180～230 ℃ after 4～24 hours.
At α, can on the acid centre of catalyst, produce the AMS intermediate in the hydrogenolysis process of α-two benzylalcohol, should make the saturated generation isopropylbenzene of its hydrogenation cause catalysqt deactivation rapidly to prevent the AMS polymerization from generating the activated centre of the duct of macromolecular substances blocking catalyst, covering catalyst.Therefore, the acidic site of catalyst and hydrogenation sites should well be mated.The quantity in the acid site of catalyst and acid strength can be regulated by the content and the handling procedure of aluminium oxide, and the hydrogenation activity of catalyst can be adjusted by the content and the decentralization of metallic copper.Simultaneously, thermal sintering takes place in copper catalyst easily, makes the copper crystallite dimension grow up, and causes activity of such catalysts and stable reduction.The present invention is by reasonably controlling synthesis program and introducing additive, the sintering that has suppressed copper crystal grain with grow up, thereby make copper catalyst keep active preferably and stability.With the copper catalyst of method preparation provided by the invention, it is 1.5 hours at 200 ℃ of reaction temperatures, reaction pressure 0.1MPa, raw material volume space velocity
-1Hydrogen and α, the mol ratio of alpha-alpha-dimethyl benzylalcohol is to be applied to α under 8.0 the reaction condition, alpha-alpha-dimethyl benzylalcohol hydrogenolysis synthesizing iso-propylbenzene process, react after 200 hours, activity of such catalysts and selectivity are constant substantially, α, the copper catalyst of the selectivity ratios prior art for preparing of the conversion ratio of alpha-alpha-dimethyl benzylalcohol and isopropylbenzene has improved 2.0～8.0%, has obtained better technical effect.
The present invention is further elaborated below by embodiment.
The specific embodiment
[embodiment 1]
The aluminium oxide of aequum is mixed making beating obtain slurries I with water, copper nitrate with aequum, the mixed solution of zinc nitrate and manganese nitrate and aqueous sodium carbonate splash into simultaneously and carry out co-precipitation among the slurries A, precipitation temperature is 70 ℃, the pH value of control solution is 6.5, precipitation finishes after under 70 ℃ aging 2 hours, then with washing of precipitate, filter the back 120 ℃ of dryings 4 hours, 400 ℃ of roastings 4 hours, with the graphite of baked solid weight 2%, 10% water mixing back compression molding obtains catalyst a, and (composition of catalyst is 55.0%CuO-20.0%ZnO%-24.0%Al by weight percentage
2O
3-1.0%MnO
2).
[embodiment 2]
(it is 20.0%CuO-50.0%ZnO-25.0%Al that catalyst is formed to catalyst b by weight percentage
2O
3-5.0%MnO
2), precipitation temperature is 80 ℃, and the pH value of control solution is 8.0, and all the other steps, parameter are identical with embodiment 1.
[embodiment 3]
(composition of catalyst is 30.0%CuO-20.0%ZnO%-45.0%Al to catalyst c by weight percentage
2O
3-1.5%MnO
2-3.5%TiO
2), precipitation temperature is 90 ℃, and the pH value of control solution is 8.0, and all the other steps, parameter are identical with embodiment 1.
[embodiment 4]
(composition of catalyst is 35.0%CuO-35.0%ZnO-10.0%Al to catalyst d by weight percentage
2O
3-2.0MnO
2-18.0%TiO
2), preparation process, parameter are identical with embodiment 2.
[embodiment 5]
(composition of catalyst is 30.0%CuO-30.0%ZnO-25.0%Al to catalyst e by weight percentage
2O
3-5.0%MnO
2-10.0%ZrO
2), precipitation temperature is 70 ℃, and the pH value of control solution is 8.5, and all the other preparation processes, parameter are identical with embodiment 1.
[embodiment 6]
(composition of catalyst is 30.0%CuO-15.0%ZnO-45%Al to catalyst f by weight percentage
2O
3-2.5%TiO
2-2.5%ZrO
2-5.0%MnO
2), precipitation temperature is 80 ℃, and the value of control pH solution is 7.0, and all the other preparation processes, parameter are identical with embodiment 1.
[embodiment 7]
(composition of catalyst is 40.0%CuO-20.0%ZnO-20.0%Al to catalyst g by weight percentage
2O
3-20%MnO
2), preparation process, parameter are with identical with embodiment 1.
[embodiment 8]
(it is 30.0%CuO-25.0%ZnO-30.0%Al that catalyst is formed to catalyst h by weight percentage
2O
3-0.5%MnO
2-14.5%ZrO
2), preparation process, parameter are with identical with embodiment 1.
[embodiment 9]
(composition of catalyst is 40.0%CuO-28.0%ZnO-25.0%Al to catalyst i by weight percentage
2O
3-5.0%MnO
2-2.0%TiO
2), preparation process, parameter are identical with embodiment 1.
[embodiment 10]
(composition of catalyst is 35.0%CuO-35.0%ZnO-20.0%Al to catalyst j by weight percentage
2O
3-2.0%MnO
2-5.0%TiO
2-3.0%La
2O
3), preparation process, parameter are identical with embodiment 1.
[comparative example 1]
(the Cu-Cr catalyst, form is 30.0%CuO-70.0%Cr to comparative example 1 catalyst by weight percentage
2O
3), adopt chromic nitrate and the mixed solution and the sodium carbonate liquor coprecipitation of copper nitrate to prepare, preparation process, parameter are identical with embodiment 1.
[comparative example 2]
(the Cu-Zn-Al catalyst, each is formed is 30.0%CuO-30.0%ZnO-25.0%Al to comparative example 2 by weight percentage
2O
3-5.0%MnO
2-10.0%ZrO
2).Method according to patent CN1173779C is provided is made into mixed solution and sodium carbonate liquor co-precipitation with copper nitrate, zinc nitrate, manganese nitrate and zirconium oxychloride and aluminum nitrate, and preparation process, parameter are identical with embodiment 1.
All catalyst are counted 5%H in order to percent by volume before use
2-95%N
2Gaseous mixture be used for hydrogenolysis at 230 ℃ of following reductase 12s after 4 hours.Appreciation condition: reaction raw materials is formed (in weight percent α, alpha-alpha-dimethyl benzylalcohol content is 25.0%, and isopropylbenzene content is 75.0%), and reaction pressure is 0.1MPa, H
2The mol ratio 8.0 of/benzylalcohol, raw material volume space velocity are 1.5 hours
-1Reaction condition under estimate, the hydrogenolysis result can see Table 1.
The α of table 1 different catalysts, alpha-alpha-dimethyl benzylalcohol hydrogenolysis performance
As seen from Table 1, with the copper catalyst of method preparation provided by the invention, it is 1.5 hours at 200 ℃ of reaction temperatures, reaction pressure 0.1MPa, raw material volume space velocity
-1Hydrogen and α, the mol ratio of alpha-alpha-dimethyl benzylalcohol is to be applied to α under 8.0 the reaction condition, alpha-alpha-dimethyl benzylalcohol hydrogenolysis synthesizing iso-propylbenzene process, react after 200 hours, activity of such catalysts and selectivity remain unchanged substantially, α, the copper catalyst of the selectivity ratios prior art for preparing of the conversion ratio of alpha-alpha-dimethyl benzylalcohol and isopropylbenzene has improved 2.0～8.0%, has obtained better technical effect.
Claims (5)
1. α, the copper catalyst of alpha-alpha-dimethyl benzylalcohol hydrogenolysis preparing isopropylbenzene comprises following component by weight percentage:
a)20.0～55.0％CuO；
b)15.0～50.0％ZnO；
c)10.0～45.0％Al
2O
3；
D) 1.0～20.0% auxiliary agents are selected from MnO
2, TiO
2Or ZrO
2In at least a.
2. α according to claim 1, the copper catalyst of alpha-alpha-dimethyl benzylalcohol hydrogenolysis preparing isopropylbenzene is characterized in that the consumption of CuO is 25.0～45.0% by weight percentage, the consumption of ZnO is 20.0～40.0%, Al
2O
3Consumption be 15.0～40.0%, be selected from MnO
2, TiO
2Or ZrO
2In at least a consumption be 1.0～15.0%.
3. α according to claim 1, the copper catalyst of alpha-alpha-dimethyl benzylalcohol hydrogenolysis preparing isopropylbenzene is characterized in that d) component is selected from MnO
2And TiO
2Or ZrO
2In at least a mixture, wherein by weight percentage, MnO
2Consumption be 0.5～5.0%, be selected from TiO
2Or ZrO
2In at least a consumption be 2.0～14.5%.
4. the described α of claim 1, the preparation method of the copper catalyst of alpha-alpha-dimethyl benzylalcohol hydrogenolysis preparing isopropylbenzene may further comprise the steps:
1) aluminium oxide of aequum is mixed making beating with water and obtain slurries I;
2) with Cu, the Zn of aequum and be selected from the mixed solution of at least a salt among Mn, Ti or the Zr and the aqueous solution of sodium carbonate splashes into simultaneously and carries out co-precipitation among the slurries I, through aging, washing, dry and 300～500 ℃ of roastings after 0.5～8 hour, mixes afterwards to obtain catalyst behind the compression molding with graphite, the water of aequum.
5. according to the α described in the claim 4, the preparation method of the copper catalyst of alpha-alpha-dimethyl benzylalcohol hydrogenolysis preparing isopropylbenzene, the temperature that it is characterized in that co-precipitation is 70～90 ℃, the pH value of solution value is 6.5～8.5.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100578152A CN101992098A (en) | 2009-08-31 | 2009-08-31 | Copper catalyst for preparing isopropyl benzene by alpha, alpha-dimethyl benzyl alcohol hydrogenolysis and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100578152A CN101992098A (en) | 2009-08-31 | 2009-08-31 | Copper catalyst for preparing isopropyl benzene by alpha, alpha-dimethyl benzyl alcohol hydrogenolysis and preparation method thereof |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102746100A (en) * | 2011-04-20 | 2012-10-24 | 中国石油化工股份有限公司 | Preparation method of cumene |
| CN108929189A (en) * | 2018-08-07 | 2018-12-04 | 崔九香 | A method of isopropylbenzene is prepared by hydrogenolysis of alpha, alpha-dimethyl benzyl alcohol |
| CN110075857A (en) * | 2019-05-09 | 2019-08-02 | 万华化学集团股份有限公司 | A kind of dimethyl benzyl alcohol hydrogenolysis catalyst and preparation method thereof |
| CN111036222A (en) * | 2019-11-22 | 2020-04-21 | 万华化学集团股份有限公司 | Catalyst for preparing isopropylbenzene by hydrogenolysis of α -dimethyl benzyl alcohol and preparation method and application thereof |
| CN111068747A (en) * | 2018-10-18 | 2020-04-28 | 中国石油化工股份有限公司 | Catalyst for preparing isopropyl benzene by hydrogenolysis and application thereof |
| CN112823883A (en) * | 2019-11-20 | 2021-05-21 | 万华化学集团股份有限公司 | Alpha, alpha-dimethyl benzyl alcohol hydrogenolysis catalyst and preparation method and application thereof |
| CN113058608A (en) * | 2020-01-02 | 2021-07-02 | 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 thereof |
| CN113058585A (en) * | 2020-01-02 | 2021-07-02 | 万华化学集团股份有限公司 | Alpha, alpha-dimethyl benzyl alcohol hydrogenolysis catalyst and preparation method thereof |
| CN114436739A (en) * | 2020-10-16 | 2022-05-06 | 中国石油化工股份有限公司 | Method for preparing isopropyl benzene and obtained 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 |
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2009
- 2009-08-31 CN CN2009100578152A patent/CN101992098A/en active Pending
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102746100A (en) * | 2011-04-20 | 2012-10-24 | 中国石油化工股份有限公司 | Preparation method of cumene |
| CN108929189A (en) * | 2018-08-07 | 2018-12-04 | 崔九香 | A method of isopropylbenzene is prepared by hydrogenolysis of alpha, alpha-dimethyl benzyl alcohol |
| CN108929189B (en) * | 2018-08-07 | 2021-06-11 | 杭州伽南企业管理有限公司 | Method for preparing isopropylbenzene by hydrogenolysis of alpha, alpha-dimethyl benzyl alcohol |
| CN111068747B (en) * | 2018-10-18 | 2023-08-08 | 中国石油化工股份有限公司 | Catalyst for preparing isopropylbenzene by hydrogenolysis and application thereof |
| CN111068747A (en) * | 2018-10-18 | 2020-04-28 | 中国石油化工股份有限公司 | Catalyst for preparing isopropyl benzene by hydrogenolysis and application thereof |
| CN110075857A (en) * | 2019-05-09 | 2019-08-02 | 万华化学集团股份有限公司 | A kind of dimethyl benzyl alcohol hydrogenolysis catalyst and preparation method thereof |
| CN112823883B (en) * | 2019-11-20 | 2022-07-12 | 万华化学集团股份有限公司 | Alpha, alpha-dimethyl benzyl alcohol hydrogenolysis catalyst and preparation method and application thereof |
| CN112823883A (en) * | 2019-11-20 | 2021-05-21 | 万华化学集团股份有限公司 | Alpha, alpha-dimethyl benzyl alcohol hydrogenolysis catalyst and preparation method and application thereof |
| CN111036222B (en) * | 2019-11-22 | 2022-08-05 | 万华化学集团股份有限公司 | Catalyst for preparing isopropylbenzene by hydrogenolysis of alpha, alpha-dimethyl benzyl alcohol and preparation method and application thereof |
| CN111036222A (en) * | 2019-11-22 | 2020-04-21 | 万华化学集团股份有限公司 | Catalyst for preparing isopropylbenzene by hydrogenolysis of α -dimethyl benzyl alcohol and preparation method and application thereof |
| CN113058585A (en) * | 2020-01-02 | 2021-07-02 | 万华化学集团股份有限公司 | Alpha, alpha-dimethyl benzyl alcohol hydrogenolysis catalyst and preparation method thereof |
| CN113058585B (en) * | 2020-01-02 | 2022-07-12 | 万华化学集团股份有限公司 | Alpha, alpha-dimethyl benzyl alcohol hydrogenolysis catalyst and preparation method thereof |
| CN113058608A (en) * | 2020-01-02 | 2021-07-02 | 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 thereof |
| CN113058608B (en) * | 2020-01-02 | 2023-01-13 | 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 thereof |
| CN114436739A (en) * | 2020-10-16 | 2022-05-06 | 中国石油化工股份有限公司 | Method for preparing isopropyl benzene and obtained 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 |
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Application publication date: 20110330 |