CN102698761A - Preparation method of catalyst for hexone synthesis by acetone hydrogenation and application - Google Patents
Preparation method of catalyst for hexone synthesis by acetone hydrogenation and application Download PDFInfo
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Abstract
The invention belongs to the technical field of catalysis, and relates to a preparation method of a catalyst for hexone synthesis by acetone hydrogenation and an application; the catalyst is composed of active component nickel loaded on an alumina carrier modified by transition metal oxides. The preparation method of the catalyst comprises two procedures: the first one is that transition metal oxides and alumina are mixed, molded, dried, roasted, and subject to hydro-thermal treatment, and the active component Ni is immersed to obtain the catalyst; the second one is that an alumina carrier is prepared firstly, then transition metal oxides and Ni are introduced by an immersion method, and finally hydro-thermal treatment is performed to obtain the catalyst. The catalyst of the invention adopts non-noble metal as the main active component, is simple in preparation, low in cost, strong in raw material adaptability, long in service life, and high in activity and selectivity, and combines three catalytic functions of acetone condensation, dehydration, and hydrogenation as a whole, and the reaction process flow is simplified greatly.
Description
Technical field
The invention belongs to catalysis technical field, be a kind of method for making and purposes of acetone hydrogenation synthesize methyl-isobutyl ketone catalyst; Technological process in particular to a kind of Preparation of catalysts method of acetone hydrogenation one-step method synthesize methyl-isobutyl ketone and uses thereof hydrogenation one-step method synthesize methyl-isobutyl ketone.
Background technology
Hexone (MIBK) is a kind of good medium-boiling solvent and chemical intermediate, can be used as paint, nitrocellulose, ethyl cellulose, video and audio recording tape, paraffin and multiple natural synthetic resin solvent; Dewaxing agent in the lube oil finishing; The extractant of rare earth metal, tantalum niobium salt; The raw material of age resistor; Agricultural chemicals extractant etc.In recent years, along with the continuous expansion of application, both at home and abroad demand constantly increases, and therefore researchs and develops novel synthetic catalyst and process route has great importance.
Industry is at present gone up production MIBK and is still adopted traditional three-step approach; Be that acetone condensation under base catalysis obtains the dipropyl alcohol ketone; Dipropyl alcohol ketone dehydration generates isopropylidene acetone under the acid catalysis effect then, again nickel or the effect of copper system with in depress hydrogenation and obtain MIBK at last.This technological process is complicated, and the production cycle is long, and cost is high, energy consumption is lacked competitiveness greatly.
In recent years, the research of the synthetic MIBK of acetone one-step method more and more comes into one's own.This method collects ketone condensation, dehydration and hydrogenation three and goes on foot in a reactor and accomplish, and advantage such as have that technological process is short, small investment and production cost are low has been represented the developing direction of MIBK production technology, has broad application prospects.Its technological key is high activity and the optionally exploitation of catalyst.
US3953517, CN 1288782A and CN1457927A disclose the Catalysts and its preparation method of methylisobutanone synthesized from acetone.This catalyst adopts resin as carrier, is reactive metal with the Metal Palladium.Such catalyst conversion ratio and selectivity are all better, and the life-span is longer, but the sulfonate radical on the resin has loss in the running, and equipment is corrosive, and the palladium that is supported on the resin is prone to run off.
CN 1385241A discloses a kind of Catalysts and its preparation method of synthesize methyl-isobutyl ketone.The percentage by weight of catalyst consists of: Pd:0.051～0.750%, ZSM-5 molecular sieve: 99.250～99.949%.At 220 ℃ of temperature, pressure 2.5MPa, volume space velocity 1.5h
-1Under the condition, use this catalyst can acetone one be gone on foot hydrogenation synthesize methyl-isobutyl ketone.CN1069674A and US3666816 disclose the Pd/Al of synthesize methyl-isobutyl ketone respectively
2O
3With the Pd/ molecular sieve catalyst.Palladium be difficult for to run off though such catalyst has, advantage such as etching apparatus not, meet water intensity descend very fast, the life-span short (＜2000h).In addition, owing to use expensive palladium and ZSM-5 as key component, cost is higher, and reaction temperature and pressure are higher, the operating condition harshness.
Summary of the invention
To the deficiency of prior art, the purpose of this invention is to provide a kind of synthetic technological process of Preparation of catalysts method and uses thereof hydrogenation one-step method of acetone hydrogenation one-step method synthesize methyl-isobutyl ketone.Catalyst of the present invention is made up of nickel, transition metal oxide and aluminium oxide; Adopt immersion process for preparing; The preparation method is simple; Have good activity, stability and selectivity, owing to select inorganic carrier for use, the equipment corrosion problem that does not exist the Pd/ resin catalyst to run off and cause at the start of run sulfonate radical; In addition, be active component with base metal nickel, overcome the shortcoming that the palladium series catalyst active component is prone to run off, cost is high, can significantly reduce the production cost of MIBK.
The present invention at first provides a kind of method for making of acetone hydrogenation one-step method synthesize methyl-isobutyl ketone catalyst, it is characterized in that: percentage by weight consists of the nickel of 3.0～40.0wt%, the transition metal oxide of 10.0～50.0wt% and the aluminium oxide of surplus.Described transition metal oxide refers to one or more in zinc oxide, manganese oxide, zirconia, chromium oxide, cupric oxide, iron oxide, vanadium oxide, the titanium dioxide.
Preparation comprises two kinds of operations:
One of operation concrete steps are following:
1) at first aluminium oxide, transition metal oxide, pore creating material and extrusion aid are mixed, moulding, drying, roasting make complex carrier; Baking temperature is 80～150 ℃, preferred 90～120 ℃; Be 6～15 hours drying time, preferred 8～12 hours; Sintering temperature is 400～750 ℃, preferred 450～600 ℃; Time is 1～6 hour, preferred 2～4 hours;
2) carrier that step 1) is made was handled preferred 400～550 ℃ and 4～8 hours 1～10 hour 330～600 ℃ of following pure water vapor; The weight ratio of total water amount and catalyst is 5～15 during processing, preferred weight ratio 6～12;
3) with the aqueous solution impregnation steps 2 of the soluble-salt of nickel) carrier that makes, dry, roasting makes catalyst; The consumption of maceration extract is every gram carrier 0.5～2.0ml during dipping, and the soluble-salt of said nickel is selected from one or more in nickel nitrate, nickel acetate, nickelous sulfate, the nickel chloride etc., preferred nickel nitrate/or nickel acetate; Dipping temperature is room temperature～85 ℃; Baking temperature is 80～150 ℃, preferred 95～120 ℃; Time is 6～15 hours, preferred 8～12 hours; Sintering temperature is 300～550 ℃, preferred 350～500 ℃; Time is 1～6 hour, preferred 2～4 hours.
In this operation method, 2), 3) order in step can put upside down, promptly the carrier that makes of step 1) earlier set by step 3) method introduce active metal nickel, and then set by step 2) method carry out hydrothermal treatment consists.
Two concrete steps of operation are following:
1) aluminium oxide and pore creating material mixed-forming, drying, roasting are made carrier; Baking temperature is 80～150 ℃, preferred 90～120 ℃; Be 6～15 hours drying time, preferred 8～12 hours; Sintering temperature is 400～750 ℃, preferred 450～600 ℃; Time is 1～6 hour, preferred 2～4 hours;
2) soluble-salt and the complexing agent with nickel and transition metal oxide is dissolved in water, and is made into mixed solution impregnation steps 1) carrier that makes, dry, roasting makes catalyst; Described complexing agent is selected from one or more in organic acid such as citric acid, tartaric acid etc. or organic amine such as ethylenediamine, the monoethanolamine etc.; The soluble-salt of said nickel is selected from one or more in nickel nitrate, nickel acetate, nickelous sulfate, the nickel chloride etc., preferred nickel nitrate/or nickel acetate; The soluble-salt of transition metal oxide is selected from one or more in nitrate, acetate, sulfate, the chloride etc., preferably nitrate/or acetate; Dipping temperature is room temperature～85 ℃; Baking temperature is 80～150 ℃, preferred 95～120 ℃; Time is 6～15 hours, preferred 8～12 hours; Sintering temperature is 300～550 ℃, preferred 350～500 ℃; Time is 1～6 hour, preferred 2～4 hours;
3) with step 2) catalyst that makes handled preferred 400～550 ℃ and 4～8 hours 1～10 hour 330～600 ℃ of following pure water vapor; The weight ratio of total water amount and catalyst is 5～15 during processing, preferred weight ratio 6～12.
In this operation method, 2), 3) order in step can put upside down, promptly the carrier that makes of step 1) earlier set by step 3) method carry out hydrothermal treatment consists, and then set by step 2) method introduce active metal nickel.
The shape of catalyst of the present invention can be bar shaped, sphere, sheet shape or graininess, and is preferred spherical.The catalyst of different shape all can adopt conventional method preparation; With the raw material porphyrize, add nitric acid or the aqueous acetic acid of 1～6wt% earlier, mixing, moulding, dry then, roasting makes finished catalyst.
The invention still further relates to the purposes of acetone hydrogenation one-step method synthesize methyl-isobutyl ketone catalyst: catalyst promptly of the present invention is used for the technological process of acetone hydrogenation one-step method synthesize methyl-isobutyl ketone: it is characterized in that: acetone hydrogenation synthesize methyl-isobutyl ketone one-step method course of reaction is carried out at fixed bed reactors; Catalyst at first reduces processing, and reducing condition is pressure 0.1～2.0MPa, 120～600 ℃ of temperature, and 0.5～8 hour time, reducing atmosphere is H
2Or H
2/ N
2Or H
2The gaseous mixture of/He, hydrogen content are 3～95v%, and the flow of reducing gas is 50～450ml/h; Reduction finishes back feeding acetone raw material and carries out hydrogenation reaction, and the reaction stagnation pressure is the volume space velocity 0.2～2.0h of 0.5～3.0MPa, 100～250 ℃ of temperature, acetone feed
-1, hydrogen and acetone mol ratio 1.5～6; Hydrogenation material gets into rectifying column, isolate methyl iso-butyl ketone (MIBK) and other accessory substances after, unreacted acetone recycle gets into fixed bed reactors and continues reaction.
Compared with prior art, advantage of the present invention comprises:
(1) catalyst provided by the invention integrates ketone condensation, dehydration and hydrogenation three big catalytic action; Whole synthetic reaction is carried out in a reactor; Compare with traditional three-step synthesis method; Have advantages such as technological process weak point, small investment and production cost are low, can significantly reduce the production cost of MIBK;
(2) catalyst provided by the invention is a reactive metal with base metal nickel, and cost is lower, and adaptability to raw material is strong, and having overcome is that the palladium-resin catalyst palladium of reactive metal is prone to shortcomings such as loss, cost costliness with the Metal Palladium;
(3) catalyst provided by the invention is a carrier with transition metal oxide/aluminium oxide, and intensity is high, has ketone condensation, dehydration two big catalysis simultaneously concurrently; There is not the problem that the sulfonate radical on the resin runs off and causes in the palladium-resin catalyst running to equipment corrosion, stable performance, the life-span is longer, and operating condition relaxes, and conversion ratio and selectivity are all better.
Figure of description
Fig. 1 is catalyst life test reaction result data and curves figure of the present invention.
The specific embodiment
Embodiment 1
Prepare catalyst of the present invention
42.8g aluminium oxide, 57.2g zinc oxide and 2g methylcellulose were mixed 30 minutes; The 3wt% dilute nitric acid solution that adds 80ml mixes after 20 minutes roller forming 3mm ball in comminutor, 120 ℃ of dryings 12 hours; 600 ℃ of roastings 3 hours make complex carrier; Then the 214.6g nickel nitrate is dissolved in water and makes settled solution, the step impregnation complex carrier, 120 ℃ of dryings 12 hours, 500 ℃ of roastings 3 hours obtain NiO/Al
2O
3-ZnO catalyst; To make spheric catalyst at last and pack in the tubular reactor, and in air, be warming up to 500 ℃ under the normal pressure, and then change water flowing steam treated 6 hours under this temperature, and feed dry air again and purge cooling, total inflow is 250g in the steam treatment process.
The catalyst of above-mentioned preparation is numbered A, and wherein nickel oxide content is 35.3wt%, and zinc oxide content is 37.0wt%, surplus be aluminium oxide.
Embodiment 2
100g aluminium oxide and 2g methylcellulose were mixed 30 minutes, add the 3wt% dilute nitric acid solution of 85ml, mix after 20 minutes roller forming 3mm ball in comminutor, 120 ℃ of dryings 12 hours, 600 ℃ of roastings 3 hours make alumina support; Then 115.8g nickel nitrate, 148.1g manganese nitrate and 10g citric acid are dissolved in water, are made into settled solution, the step impregnation alumina support, 120 ℃ of dryings 12 hours, 500 ℃ of roastings 3 hours make finished catalyst; At last above-mentioned catalyst is packed in the tubular reactor, in air, be warming up to 500 ℃ under the normal pressure, and then change water flowing steam treated 6 hours under this temperature, feed dry air again and purge cooling, total inflow is 250g in the steam treatment process.
The catalyst of above-mentioned preparation is numbered B, and wherein nickel oxide content is 16.3wt%, and manganese oxide content is 28.4wt%, surplus be aluminium oxide.
Embodiment 3
Press other catalyst of method preparation C of embodiment 1, different is earlier complex carrier to be carried out hydrothermal treatment consists, adopts infusion process to introduce active component nickel then.The same catalyst A of constituent content, wherein nickel oxide content is 32.5wt%, zinc oxide content is 39.2wt%, surplus be aluminium oxide.
Embodiment 4
Press other catalyst of method preparation D of embodiment 2, different is earlier alumina support to be carried out hydrothermal treatment consists, adopts infusion process to introduce active component nickel then.The same catalyst A of constituent content, wherein nickel content is 15.7wt%, content of magnesia is 31.2wt%, surplus be aluminium oxide.
Embodiment 5
Press other several kinds of catalyst E-F of method preparation of embodiment 2; Different is to change active component nickel and transition metal oxide type and content, is respectively E (nickel 6.2wt%, zinc oxide 46.1wt%, alumina content are surplus), F (nickel 30.5wt%, zirconia 12.9wt%, alumina content are surplus), G (nickel 15.1wt%, chromium oxide 20.6wt%, alumina content are surplus), H (nickel 25.2wt%, titanium oxide 16.8wt%, alumina content are surplus).
Comparative example 1
Described preparation method prepares Pd/ resin catalyst I according to CN 1457927A patent, and the palladium load capacity is 0.4wt%.
Comparative example 2
Described preparation method prepares Pd/ZSM-5 catalyst J according to CN 1385241A patent, and the palladium load capacity is 0.45wt%.
Embodiment 6
Active appraisal experiment
In the 100ml fixed bed reactors, being respectively charged into 100ml catalyst A-J, is raw material with technical grade acetone, and content of acetone is 98wt%.Catalyst at first reduces processing, and reducing condition is pressure 1.0MPa, 450 ℃ of temperature, and 6 hours time, reducing atmosphere is H
2/ N
2Gaseous mixture, hydrogen content is 10.0v%, the flow of reducing gas is 200ml/h; Reduction finishes back feeding acetone raw material and carries out hydrogenation reaction, and the reaction stagnation pressure is the volume space velocity 1.0h of 1.0MPa, 150 ℃ of temperature, acetone feed
-1, hydrogen and acetone mol ratio 5.The liquid product composition is analyzed with chromatography of gases.The one way reaction result is seen table 1.
Embodiment 7
In the 100ml fixed bed reactors, being respectively charged into the 100ml catalyst A, is raw material with technical grade acetone, and content of acetone is 98wt%.Catalyst at first reduces processing, and reducing condition is pressure 1.0MPa, 450 ℃ of temperature, and 6 hours time, reducing atmosphere is H
2/ N
2Gaseous mixture, hydrogen content is 10.0v%, the flow of reducing gas is 300ml/h; Reduction finishes back feeding acetone raw material and carries out hydrogenation reaction, and the reaction stagnation pressure is the volume space velocity 0.8h of 1.5MPa, 200 ℃ of temperature, acetone feed
-1, hydrogen and acetone mol ratio 5.Test number is A-2, and the liquid product composition is analyzed with chromatography of gases.The one way reaction result is seen table 1.
Embodiment 8
In the 100ml fixed bed reactors, be respectively charged into the 100ml catalyst B and carry out life test, reaction result is seen Fig. 1.
Can know that by Fig. 1 after 2000 hours catalyst B one way life-spans of the present invention, acetone conversion and MIBK selectivity all do not have obvious decline, show that catalyst of the present invention has good activity stability.
Table 1
Claims (3)
1. the method for making of an acetone hydrogenation one-step method synthesize methyl-isobutyl ketone catalyst, it is characterized in that: percentage by weight consists of the nickel of 3.0～40.0wt%, the transition metal oxide of 10.0～50.0wt% and the aluminium oxide of surplus; Described transition metal oxide refers to one or more in zinc oxide, manganese oxide, zirconia, chromium oxide, cupric oxide, iron oxide, vanadium oxide, the titanium dioxide;
Preparation comprises two kinds of operations:
One of operation concrete steps are following:
1) at first aluminium oxide, transition metal oxide, pore creating material and extrusion aid are mixed, moulding, drying, roasting make complex carrier; Baking temperature is 80～150 ℃; Be 6～15 hours drying time; Sintering temperature is 400～750 ℃; Time is 1～6 hour;
2) carrier that step 1) is made was handled 1～10 hour 330～600 ℃ of following pure water vapor; The weight ratio of total water amount and catalyst is 5～15 during processing;
3) with the aqueous solution impregnation steps 2 of the soluble-salt of nickel) carrier that makes, dry, roasting makes catalyst; The consumption of maceration extract is every gram carrier 0.5～2.0ml during dipping, and the soluble-salt of said nickel is selected from one or more in nickel nitrate, nickel acetate, nickelous sulfate, the nickel chloride etc.; Dipping temperature is room temperature～85 ℃; Baking temperature is 80～150 ℃; Time is 6～15 hours; Sintering temperature is 300～550 ℃; Time is 1～6 hour;
In this operation method, 2), 3) order in step or put upside down, promptly the carrier that makes of step 1) earlier set by step 3) method introduce active metal nickel, and then set by step 2) method carry out hydrothermal treatment consists;
Two concrete steps of operation are following:
1) aluminium oxide and pore creating material mixed-forming, drying, roasting are made carrier; Baking temperature is 80～150 ℃; Be 6～15 hours drying time; Sintering temperature is 400～750 ℃; Time is 1～6 hour;
2) soluble-salt and the complexing agent with nickel and transition metal oxide is dissolved in water, and is made into mixed solution impregnation steps 1) carrier that makes, dry, roasting makes catalyst; Described complexing agent is selected from one or more in organic acid such as citric acid, tartaric acid or organic amine such as ethylenediamine, the monoethanolamine; The soluble-salt of said nickel is selected from one or more in nickel nitrate, nickel acetate, nickelous sulfate, the nickel chloride; The soluble-salt of transition metal oxide is selected from one or more in nitrate, acetate, sulfate, the chloride; Dipping temperature is room temperature～85 ℃; Baking temperature is 80～150 ℃; Time is 6～15 hours; Sintering temperature is 300～550 ℃; Time is 1～6 hour;
3) with step 2) catalyst that makes handled 1～10 hour 330～600 ℃ of following pure water vapor; The weight ratio of total water amount and catalyst is 5～15 during processing;
In this operation method, 2), 3) order in step or put upside down, promptly the carrier that makes of step 1) earlier set by step 3) method carry out hydrothermal treatment consists, and then set by step 2) method introduce active metal nickel;
The shape of catalyst of the present invention is bar shaped, sphere, sheet shape or graininess; The catalyst of different shape all adopts conventional method preparation; With the raw material porphyrize, add nitric acid or the aqueous acetic acid of 1～6wt% earlier, mixing, moulding, dry then, roasting makes finished catalyst.
2. the purposes of an acetone hydrogenation one-step method synthesize methyl-isobutyl ketone catalyst: catalyst promptly of the present invention is used for the technological process of acetone hydrogenation one-step method synthesize methyl-isobutyl ketone: it is characterized in that: acetone hydrogenation synthesize methyl-isobutyl ketone one-step method course of reaction is carried out at fixed bed reactors; Catalyst at first reduces processing, and reducing condition is pressure 0.1～2.0MPa, 120～600 ℃ of temperature, and 0.5～8 hour time, reducing atmosphere is H
2Or H
2/ N
2Or H
2The gaseous mixture of/He, hydrogen content are 3～95v%, and the flow of reducing gas is 50～450ml/h; Reduction finishes back feeding acetone raw material and carries out hydrogenation reaction, and the reaction stagnation pressure is the volume space velocity 0.2～2.0h of 0.5～3.0MPa, 100～250 ℃ of temperature, acetone feed
-1, hydrogen and acetone mol ratio 1.5～6; Hydrogenation material gets into rectifying column, isolate methyl iso-butyl ketone (MIBK) and other accessory substances after, unreacted acetone recycle gets into fixed bed reactors and continues reaction.
3. according to the described method for making of claim 1, it is characterized in that: percentage by weight consists of the nickel of 3.2～38.0wt%, the transition metal oxide of 12～48wt% and the aluminium oxide of surplus; Described transition metal oxide refers to one or more in zinc oxide, manganese oxide, zirconia, chromium oxide, cupric oxide, the iron oxide;
Preparation comprises two kinds of operations:
One of operation concrete steps are following:
1) at first aluminium oxide, transition metal oxide, pore creating material and extrusion aid are mixed, moulding, drying, roasting make complex carrier; Baking temperature is 90～120 ℃; Be 8～12 hours drying time; Sintering temperature is 450～600 ℃; Time is 2～4 hours;
2) carrier that step 1) is made was handled 4～8 hours 400～550 ℃ of following pure water vapor; The weight ratio of total water amount and catalyst is 6～12 during processing;
3) with the aqueous solution impregnation steps 2 of the soluble-salt of nickel) carrier that makes, dry, roasting makes catalyst; The consumption of maceration extract is every gram carrier 0.5～2.0ml during dipping, and the soluble-salt of said nickel is selected from nickel nitrate/or nickel acetate; Dipping temperature is room temperature～85 ℃; Baking temperature is 95～120 ℃; Time is 8～12 hours; Sintering temperature is 350～500 ℃; Time is 2～4 hours.
In this operation method, 2), 3) order in step or put upside down, promptly the carrier that makes of step 1) earlier set by step 3) method introduce active metal nickel, and then set by step 2) method carry out hydrothermal treatment consists;
Two concrete steps of operation are following:
1) aluminium oxide and pore creating material mixed-forming, drying, roasting are made carrier; Baking temperature is 90～120 ℃; Be 8～12 hours drying time; Sintering temperature is 450～600 ℃; Time is 2～4 hours;
2) soluble-salt and the complexing agent with nickel and transition metal oxide is dissolved in water, and is made into mixed solution impregnation steps 1) carrier that makes, dry, roasting makes catalyst; Described complexing agent is selected from organic acid such as citric acid, tartaric acid or organic amine such as ethylenediamine, monoethanolamine; The soluble-salt of said nickel is selected from nickel nitrate/or nickel acetate; The soluble-salt of transition metal oxide is selected from nitrate/or acetate; Dipping temperature is room temperature～85 ℃; Baking temperature is 95～120 ℃; Time is 8～12 hours; Sintering temperature is 350～500 ℃; Time is 2～4 hours;
3) with step 2) catalyst that makes handled 4～8 hours 400～550 ℃ of following pure water vapor, and the weight ratio of total water amount and catalyst is 6～12 during processing;
In this operation method, 2), 3) order in step or put upside down, promptly the carrier that makes of step 1) earlier set by step 3) method carry out hydrothermal treatment consists, and then set by step 2) method introduce active metal nickel;
The shape of catalyst of the present invention is spherical; Catalyst adopts conventional method preparation; With the raw material porphyrize, add nitric acid or the aqueous acetic acid of 2～4wt% earlier, mixing, moulding, dry then, roasting makes finished catalyst.
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103801338A (en) * | 2012-11-07 | 2014-05-21 | 中国石油化工股份有限公司 | Catalyst for preparing methyl isobutyl ketone and preparation method |
| CN104549348B (en) * | 2013-10-22 | 2016-11-16 | 中国石油化工股份有限公司 | A kind of catalyst of acetone synthesis diisobutyl ketone and preparation method thereof |
| CN109364962A (en) * | 2018-09-30 | 2019-02-22 | 中国科学院山西煤炭化学研究所 | Nickel phosphide-based catalyst for selective hydrogenation of acetone, preparation method and application thereof |
| CN109701570A (en) * | 2017-10-26 | 2019-05-03 | 中国石油化工股份有限公司 | A kind of methylisobutanone synthesized from acetone and the catalyst of diisobutyl ketone and its preparation method and application |
| CN109701549A (en) * | 2017-10-26 | 2019-05-03 | 中国石油化工股份有限公司 | A kind of acetone through one-step method prepares catalyst of methyl iso-butyl ketone (MIBK) and its preparation method and application |
| CN109701536A (en) * | 2017-10-26 | 2019-05-03 | 中国石油化工股份有限公司 | A kind of acetone synthesizing methyl isobutyl alcohol and the catalyst of isopropanol and its preparation method and application |
| CN109701539A (en) * | 2017-10-26 | 2019-05-03 | 中国石油化工股份有限公司 | A kind of acetone prepares the catalyst and the preparation method and application thereof of methyl iso-butyl ketone (MIBK) and methyl isobutyl alcohol |
| CN109718786A (en) * | 2017-10-30 | 2019-05-07 | 中国石油化工股份有限公司 | A kind of catalyst and its preparation method and application preparing methyl iso-butyl ketone (MIBK) and diisobutyl ketone for condensation of acetone |
| CN110871076A (en) * | 2018-08-30 | 2020-03-10 | 中国石油化工股份有限公司 | Catalyst for preparing methyl isobutyl alcohol, preparation method and application |
| CN116212958A (en) * | 2023-01-03 | 2023-06-06 | 万华化学集团股份有限公司 | Resin catalyst for MIBK production, preparation method and application thereof |
| CN118384927A (en) * | 2024-04-19 | 2024-07-26 | 浙江工业大学 | Preparation method and application of composite oxide carrier |
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Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109701549B (en) * | 2017-10-26 | 2022-03-29 | 中国石油化工股份有限公司 | Catalyst for preparing methyl isobutyl ketone by acetone one-step method and preparation method and application thereof |
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| CN109718786B (en) * | 2017-10-30 | 2022-03-01 | 中国石油化工股份有限公司 | Catalyst for preparing methyl isobutyl ketone and diisobutyl ketone by acetone condensation, and preparation method and application thereof |
| CN110871076A (en) * | 2018-08-30 | 2020-03-10 | 中国石油化工股份有限公司 | Catalyst for preparing methyl isobutyl alcohol, preparation method and application |
| CN110871076B (en) * | 2018-08-30 | 2022-09-20 | 中国石油化工股份有限公司 | Catalyst for preparing methyl isobutyl alcohol, preparation method and application |
| CN109364962B (en) * | 2018-09-30 | 2021-03-02 | 中国科学院山西煤炭化学研究所 | Nickel phosphide-based catalyst for selective hydrogenation of acetone, preparation method and application thereof |
| CN109364962A (en) * | 2018-09-30 | 2019-02-22 | 中国科学院山西煤炭化学研究所 | Nickel phosphide-based catalyst for selective hydrogenation of acetone, preparation method and application thereof |
| CN116212958A (en) * | 2023-01-03 | 2023-06-06 | 万华化学集团股份有限公司 | Resin catalyst for MIBK production, preparation method and application thereof |
| CN118384927A (en) * | 2024-04-19 | 2024-07-26 | 浙江工业大学 | Preparation method and application of composite oxide carrier |
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