CN107537497A - A kind of preparation method and application for being used to prepare the catalyst of adjacent methyl cyclohexanol - Google Patents
A kind of preparation method and application for being used to prepare the catalyst of adjacent methyl cyclohexanol Download PDFInfo
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- CN107537497A CN107537497A CN201710642060.7A CN201710642060A CN107537497A CN 107537497 A CN107537497 A CN 107537497A CN 201710642060 A CN201710642060 A CN 201710642060A CN 107537497 A CN107537497 A CN 107537497A
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Abstract
The invention belongs to the preparation method and purposes of catalyst field, more particularly to a kind of catalyst for ortho-methyl phenol hydrogenation synthesis neighbour's methyl cyclohexanol.Nickel Aluminium Alloy Powder is heated and melted, cobalt powder is then added, after cobalt powder fuses into nickel alumin(i)um alloy, is crushed after carrying out quenching cooling to melt, nickel cobalt Al alloy powder is made, it is extracted with sodium hydrate aqueous solution and activated, is washed with deionized deoxygenated water to pH<8, the catalyst for ortho-methyl phenol hydrogenation synthesis neighbour's methyl cyclohexanol is made.The present invention is a kind of cobalt improved skeleton nickel by adding catalyst prepared by cobalt powder into Nickel Aluminium Alloy Powder, significantly improve the activity and selectivity of conventional skeleton nickel, it is lower than the noble metal catalyst cost such as Pt, Pd, Ru, the alloy structure for the alloy ratio conventional method preparation that the present invention is cooled into using quenching is more homogeneous in addition, performance is more stable, is advantageous to industrialized implementation.
Description
Technical field
The invention belongs to catalyst field, more particularly to a kind of preparation side for being used to prepare the catalyst of adjacent methyl cyclohexanol
Method and application.
Background technology
Adjacent methyl cyclohexanol is a kind of important chemical intermediate, and its is widely used, can be used to synthesize adjacent methyl cyclohexane vinegar
The important chemical products such as acid esters, with popularization of the adjacent methyl cyclohexane acetate as hydrogen peroxide synthetic, people are for it
The research of synthesis material neighbour's methyl cyclohexanol is also increasingly deep.
Adjacent methyl cyclohexanol mainly be prepared by ortho-methyl phenol catalytic hydrogenation, hydrogenation catalyst have Ru/C, Pd/C,
Ni/Al2O3, Raney's nickel etc..Patent CN 104628525A disclose a kind of ortho-methyl phenol Hydrogenation for adjacent methyl cyclohexanol
Method, using Ru/ZrO2、Ir/TiO2、Pd/Al2O3、Ru/SiO2It is catalyzed Deng noble metal catalyst on fixed bed reactors
Hydrogenation is for adjacent methyl cyclohexanol, 120 DEG C, reaction pressure 5MPa of reaction temperature, ortho-methyl phenol air speed 0.6h-1, hydrogen phenol mole
Than 20:1, fixed bed can continuously run 2520h, and ortho-methyl phenol conversion ratio is more than 99.4%, and adjacent methyl cyclohexanol is selectively big
In 99.7%, but the catalyst as the hydrogenation reaction is noble metal catalyst, and its is expensive, and use cost compares
It is high.Patent CN1237039C discloses a kind of ortho-methyl phenol Hydrogenation for the method for adjacent methyl cyclohexanol, uses Ni/Al2O3Urge
Agent, reaction pressure is 0.1~0.5MPa, reaction temperature prepares adjacent methyl cyclohexanol under conditions of being 150~250 DEG C, and this is urged
Agent activity is relatively low, and the yield of adjacent methyl cyclohexanol is relatively low, and the life-span of catalyst is shorter.
At present, for the reaction of adjacent methyl cyclohexanol there is the conversion ratio of ortho-methyl phenol and adjacent methyl in ortho-methyl phenol Hydrogenation
The yield of cyclohexanol is relatively low, catalyst activity is relatively low, catalyst cost is high, is unfavorable for the problems such as industrialized production.
The content of the invention
For the deficiency of the aspects such as poor catalyst activity in the prior art, easy in inactivation, cost height, the present invention provides a kind of use
In the preparation method and application for the catalyst for preparing adjacent methyl cyclohexanol.
The technical solution adopted for the present invention to solve the technical problems is：For preparing the catalyst of adjacent methyl cyclohexanol
Preparation method, its concrete operation step include：
(1) Nickel Aluminium Alloy Powder is heated and melted, then add cobalt powder, after cobalt powder fuses into nickel alumin(i)um alloy, melt is carried out
Quenching cooling, then be crushed to below 200 mesh, nickel cobalt Al alloy powder is made；
(2) nickel cobalt Al alloy powder prepared by step (1) is taken out with the sodium hydrate aqueous solution that mass fraction is 10~25%
Activation is proposed, is washed with deionized deoxygenated water to pH<8, the catalyst for preparing adjacent methyl cyclohexanol is made.
Wherein, in step (1), cobalt/nickel mol ratio is 1:100~1:20, the mass percent of nickel is in Nickel Aluminium Alloy Powder
40~60%, remaining is aluminium, has a kind of structure of conventional skeleton nickel；Cobalt powder is cobalt simple substance.
The mass fraction of the sodium hydrate aqueous solution of step (2) the extracting activation is 20%.
A kind of application for being used to prepare the catalyst of adjacent methyl cyclohexanol, the catalyst are used for ortho-methyl phenol Hydrogenation
Standby adjacent methyl cyclohexanol, its concrete operation step include：
Using ortho-methyl phenol as raw material, under the conditions of existing for solvent and catalyst, it is passed through hydrogen and carries out catalytic reaction system
Standby adjacent methyl cyclohexanol.The temperature of catalytic reaction is 80 DEG C~180 DEG C, and the reaction time is：5~10 hours, it is passed through the pressure of hydrogen
Power is 2MPa~6MPa.Solvent for use is water, methanol, ethanol, one kind in dimethylformamide, ortho-methyl phenol and solvent
Mass ratio is 1：10~2：1, the addition of hydrogenation catalyst used therein accounts for the 5%~20% of ortho-methyl phenol
The beneficial effects of the invention are as follows：The present invention is a kind of by adding catalyst prepared by cobalt powder into Nickel Aluminium Alloy Powder
Cobalt improved skeleton nickel, the aluminium in nickel aluminium or nickel aluminium cobalt alloy is then dissolved using sodium hydroxide, after aluminium is dissolved, the original position of aluminium
Put and reformed into cavity, so as to significantly improve the activity and selectivity of conventional skeleton nickel, the catalyst is more expensive than Pt, Pd, Ru etc.
Metallic catalyst cost is low, and alloy structure prepared by the alloy ratio conventional method that the present invention is cooled into using quenching in addition is more equal
First, performance is more stable, is advantageous to industrialized implementation.
Embodiment
The present invention is described in more detail below by reference to embodiment, but protection scope of the present invention is not limited
In these embodiments.
Embodiment 1
Prepare catalyst：
(1) 100g Nickel Aluminium Alloy Powders are heated and melted, then add 0.5g cobalt powders, it is right after cobalt powder fuses into nickel alumin(i)um alloy
Melt carries out quenching cooling, then is crushed to below 200 mesh, and nickel cobalt Al alloy powder is made；The quality of nickel wherein in Nickel Aluminium Alloy Powder
Percentage is 50%.
(2) with vigorous stirring, nickel cobalt Al alloy powder prepared by step (1) is gradually added into 800ml mass concentrations is
In 20% sodium hydrate aqueous solution, continue stirring 15 minutes after adding, stand 30 minutes, after not molten thing sedimentation, decantation removes
Upper solution is gone, with deionized deoxygenated water washing and depositing thing, adds water 800ml every time, until pH value of solution<8, it is made for preparing neighbour
The catalyst of methyl cyclohexanol.
Prepare adjacent methyl cyclohexanol：
In 100ml autoclave, ortho-methyl phenol 5g, ethanol 25ml, catalyst 0.5g are added, reaction temperature is
140 DEG C, Hydrogen Vapor Pressure 4MPa, 5h is reacted, adjacent methyl cyclohexanol is made.
Embodiment 2
Prepare catalyst：
(1) 100g Nickel Aluminium Alloy Powders are heated and melted, then add 1.25g cobalt powders, it is right after cobalt powder fuses into nickel alumin(i)um alloy
Melt carries out quenching cooling, then is crushed to below 200 mesh, and nickel cobalt Al alloy powder is made；The quality of nickel wherein in Nickel Aluminium Alloy Powder
Percentage is 50%.
(2) with vigorous stirring, nickel cobalt Al alloy powder prepared by step (1) is gradually added into 800ml mass concentrations is
In 20% sodium hydrate aqueous solution, continue stirring 15 minutes after adding, stand 30 minutes, after not molten thing sedimentation, decantation removes
Upper solution is gone, with deionized deoxygenated water washing and depositing thing, adds water 800ml every time, until pH value of solution<8, it is made for preparing neighbour
The catalyst of methyl cyclohexanol.
Prepare adjacent methyl cyclohexanol：
In 100ml autoclave, ortho-methyl phenol 20g, dimethylformamide 20ml, catalyst 2g are added, instead
It is 140 DEG C, Hydrogen Vapor Pressure 4MPa to answer temperature, reacts 5h, and adjacent methyl cyclohexanol is made.
Embodiment 3
Prepare catalyst：
(1) 100g Nickel Aluminium Alloy Powders are heated and melted, then add 2.5g cobalt powders, it is right after cobalt powder fuses into nickel alumin(i)um alloy
Melt carries out quenching cooling, then is crushed to below 200 mesh, and nickel cobalt Al alloy powder is made；The quality of nickel wherein in Nickel Aluminium Alloy Powder
Percentage is 50%.
(2) with vigorous stirring, nickel cobalt Al alloy powder prepared by step (1) is gradually added into 800ml mass concentrations is
In 20% sodium hydrate aqueous solution, continue stirring 15 minutes after adding, stand 30 minutes, after not molten thing sedimentation, decantation removes
Upper solution is gone, with deionized deoxygenated water washing and depositing thing, adds water 800ml every time, until pH value of solution<8, it is made for preparing neighbour
The catalyst of methyl cyclohexanol.
Prepare adjacent methyl cyclohexanol：
In 100ml autoclave, ortho-methyl phenol 30g, ethanol 15ml, catalyst 3g are added, reaction temperature is
140 DEG C, Hydrogen Vapor Pressure 4MPa, reaction time 8h, adjacent methyl cyclohexanol is made.
Embodiment 4
Prepare catalyst：
(1) 100g Nickel Aluminium Alloy Powders are heated and melted, then add 0.5g cobalt powders, it is right after cobalt powder fuses into nickel alumin(i)um alloy
Melt carries out quenching cooling, then is crushed to below 200 mesh, and nickel cobalt Al alloy powder is made；The quality of nickel wherein in Nickel Aluminium Alloy Powder
Percentage is 50%.
(2) with vigorous stirring, nickel cobalt Al alloy powder prepared by step (1) is gradually added into 800ml mass concentrations is
In 20% sodium hydrate aqueous solution, continue stirring 15 minutes after adding, stand 30 minutes, after not molten thing sedimentation, decantation removes
Upper solution is gone, with deionized deoxygenated water washing and depositing thing, adds water 800ml every time, until pH value of solution<8, it is made for preparing neighbour
The catalyst of methyl cyclohexanol.
Prepare adjacent methyl cyclohexanol：
In 100ml autoclave, ortho-methyl phenol 5g, methanol 25ml, catalyst 0.5g are added, reaction temperature is
140 DEG C, Hydrogen Vapor Pressure 2MPa, react 10h.
Embodiment 5
Prepare catalyst：
(1) 100g Nickel Aluminium Alloy Powders are heated and melted, then add 1.25g cobalt powders, it is right after cobalt powder fuses into nickel alumin(i)um alloy
Melt carries out quenching cooling, then is crushed to below 200 mesh, and nickel cobalt Al alloy powder is made；The quality of nickel wherein in Nickel Aluminium Alloy Powder
Percentage is 50%.
(2) with vigorous stirring, nickel cobalt Al alloy powder prepared by step (1) is gradually added into 800ml mass concentrations is
In 20% sodium hydrate aqueous solution, continue stirring 15 minutes after adding, stand 30 minutes, after not molten thing sedimentation, decantation removes
Upper solution is gone, with deionized deoxygenated water washing and depositing thing, adds water 800ml every time, until pH value of solution<8, it is made for preparing neighbour
The catalyst of methyl cyclohexanol.
Prepare adjacent methyl cyclohexanol：
In 100ml autoclave, ortho-methyl phenol 20g, dimethylformamide 20ml, catalyst 2g are added, instead
It is 140 DEG C, Hydrogen Vapor Pressure 3MPa to answer temperature, reacts 6h, and adjacent methyl cyclohexanol is made.
Embodiment 6
Prepare catalyst：
(1) 100g Nickel Aluminium Alloy Powders are heated and melted, then add 2.5g cobalt powders, it is right after cobalt powder fuses into nickel alumin(i)um alloy
Melt carries out quenching cooling, then is crushed to below 200 mesh, and nickel cobalt Al alloy powder is made；The quality of nickel wherein in Nickel Aluminium Alloy Powder
Percentage is 50%.
(2) with vigorous stirring, nickel cobalt Al alloy powder prepared by step (1) is gradually added into 800ml mass concentrations is
In 20% sodium hydrate aqueous solution, continue stirring 15 minutes after adding, stand 30 minutes, after not molten thing sedimentation, decantation removes
Upper solution is gone, with deionized deoxygenated water washing and depositing thing, adds water 800ml every time, until pH value of solution<8, it is made for preparing neighbour
The catalyst of methyl cyclohexanol.
Prepare adjacent methyl cyclohexanol：
In 100ml autoclave, ortho-methyl phenol 30g, ethanol 15ml, catalyst 6g are added, reaction temperature is
120 DEG C, Hydrogen Vapor Pressure 4MPa, reaction time 8h, adjacent methyl cyclohexanol is made.
Embodiment 7
Prepare catalyst：
(1) 100g Nickel Aluminium Alloy Powders are heated and melted, then add 2.5g cobalt powders, it is right after cobalt powder fuses into nickel alumin(i)um alloy
Melt carries out quenching cooling, then is crushed to below 200 mesh, and nickel cobalt Al alloy powder is made；The quality of nickel wherein in Nickel Aluminium Alloy Powder
Percentage is 50%.
(2) with vigorous stirring, nickel cobalt Al alloy powder prepared by step (1) is gradually added into 800ml mass concentrations is
In 20% sodium hydrate aqueous solution, continue stirring 15 minutes after adding, stand 30 minutes, after not molten thing sedimentation, decantation removes
Upper solution is gone, with deionized deoxygenated water washing and depositing thing, adds water 800ml every time, until pH value of solution<8, it is made for preparing neighbour
The catalyst of methyl cyclohexanol.
Prepare adjacent methyl cyclohexanol：
In 100ml autoclave, ortho-methyl phenol 20g, deionized water 20ml, catalyst 2g, reaction temperature are added
Spend for 160 DEG C, Hydrogen Vapor Pressure 3MPa, react 5h, adjacent methyl cyclohexanol is made.
Embodiment 8
(1) 100g Nickel Aluminium Alloy Powders are heated and melted, then add 1.25g cobalt powders, it is right after cobalt powder fuses into nickel alumin(i)um alloy
Melt carries out quenching cooling, then is crushed to below 200 mesh, and nickel cobalt Al alloy powder is made；The quality of nickel wherein in Nickel Aluminium Alloy Powder
Percentage is 50%.
(2) with vigorous stirring, nickel cobalt Al alloy powder prepared by step (1) is gradually added into 800ml mass concentrations is
In 20% sodium hydrate aqueous solution, continue stirring 15 minutes after adding, stand 30 minutes, after not molten thing sedimentation, decantation removes
Upper solution is gone, with deionized deoxygenated water washing and depositing thing, adds water 800ml every time, until pH value of solution<8, it is made for preparing neighbour
The catalyst of methyl cyclohexanol.
Prepare adjacent methyl cyclohexanol：
In 100ml autoclave, ortho-methyl phenol 20g, methanol 20ml, catalyst 1g are added, reaction temperature is
140 DEG C, Hydrogen Vapor Pressure 4MPa, 5h is reacted, adjacent methyl cyclohexanol is made.
Embodiment 9
Prepare catalyst：
(1) 100g Nickel Aluminium Alloy Powders are heated and melted, then add 2.5g cobalt powders, it is right after cobalt powder fuses into nickel alumin(i)um alloy
Melt carries out quenching cooling, then is crushed to below 200 mesh, and nickel cobalt Al alloy powder is made；The quality of nickel wherein in Nickel Aluminium Alloy Powder
Percentage is 50%.
(2) with vigorous stirring, nickel cobalt Al alloy powder prepared by step (1) is gradually added into 800ml mass concentrations is
In 20% sodium hydrate aqueous solution, continue stirring 15 minutes after adding, stand 30 minutes, after not molten thing sedimentation, decantation removes
Upper solution is gone, with deionized deoxygenated water washing and depositing thing, adds water 800ml every time, until pH value of solution<8, it is made for adjacent methyl
Phenol hydrogenation synthesizes the catalyst of adjacent methyl cyclohexanol.
Prepare adjacent methyl cyclohexanol：
In 100ml autoclave, ortho-methyl phenol 20g, water 20ml, catalyst 2g, reaction temperature 140 are added
DEG C, Hydrogen Vapor Pressure 4MPa, 5h is reacted, adjacent methyl cyclohexanol is made.
Comparative example 1
Prepare catalyst：
(1) 100g Nickel Aluminium Alloy Powders are heated and melted, quenching cooling is carried out to melt, then be crushed to below 200 mesh, is made
Nickel Aluminium Alloy Powder；The mass percent of nickel is 50% wherein in Nickel Aluminium Alloy Powder.
(2) with vigorous stirring, Nickel Aluminium Alloy Powder prepared by step (1) is gradually added 800ml mass concentrations as 20%
Sodium hydrate aqueous solution in, continue stirring 15 minutes after adding, stand 30 minutes, after the sedimentation of not molten thing, on decantation removes
Layer solution, with deionized deoxygenated water washing and depositing thing, add water 800ml every time, until pH value of solution<8, it is made for preparing adjacent methyl
The catalyst of cyclohexanol.
Prepare adjacent methyl cyclohexanol：
In 100ml autoclave, ortho-methyl phenol 20g, water 20ml, catalyst 2g, reaction temperature 140 are added
DEG C, Hydrogen Vapor Pressure 4MPa, 5h is reacted, adjacent methyl cyclohexanol is made.
Performance test：
The reaction solution prepared using gas chromatography to embodiment 1~9 and comparative example 1 is analyzed, and calculates hydrogenation reaction
Conversion ratio, selectivity and yield, as a result it is listed in table 1.
The embodiment 1-9 of table 1 and comparative example 1 hydrogenation reaction result
Cobalt improved skeletal nickel catalyst prepared by the explanation the solution of the present invention of table 1 is to ortho-methyl phenol Hydrogenation for adjacent first
Cyclohexanol reaction has higher activity and selectivity, and preparation process is simple, is more preferable catalyst.
It is complete by above-mentioned description, relevant staff using the above-mentioned desirable embodiment according to the present invention as enlightenment
Various changes and amendments can be carried out without departing from the scope of the technological thought of the present invention' entirely.The technology of this invention
Property scope is not limited to the content on specification, it is necessary to determines its technical scope according to right.
Claims (7)
- A kind of 1. preparation method for being used to prepare the catalyst of adjacent methyl cyclohexanol, it is characterised in that：The preparation method is specific Operating procedure includes：(1) Nickel Aluminium Alloy Powder is heated and melted, then added cobalt powder, after cobalt powder fuses into nickel alumin(i)um alloy, melt is quenched Cooling, then be crushed to below 200 mesh, nickel cobalt Al alloy powder is made；(2) sodium hydrate aqueous solution that the nickel cobalt Al alloy powder mass fraction for preparing step (1) is 10~25%, which extracts, lives Change, washed with deionized deoxygenated water to pH<8, the catalyst for preparing adjacent methyl cyclohexanol is made.
- 2. the preparation method as claimed in claim 1 for being used to prepare the catalyst of adjacent methyl cyclohexanol, it is characterised in that：Step (1) mol ratio of cobalt and nickel described in is 1：100~1：20.
- 3. the preparation method as claimed in claim 1 for being used to prepare the catalyst of adjacent methyl cyclohexanol, it is characterised in that：Step (2) mass fraction of the sodium hydrate aqueous solution described in is 20%.
- 4. the application as claimed in claim 1 for being used to prepare the catalyst of adjacent methyl cyclohexanol, it is characterised in that：The catalysis Agent is for adjacent methyl cyclohexanol, its concrete application method for ortho-methyl phenol Hydrogenation：Using ortho-methyl phenol as raw material, under the conditions of existing for solvent and catalyst, it is passed through hydrogen and carries out catalytic reaction preparation neighbour Methyl cyclohexanol.
- 5. the application as claimed in claim 4 for being used to prepare the catalyst of adjacent methyl cyclohexanol, it is characterised in that：Described is molten Agent is one kind in water, methanol, ethanol, dimethylformamide.
- 6. the application as claimed in claim 4 for being used to prepare the catalyst of adjacent methyl cyclohexanol, it is characterised in that：The adjacent first The mass ratio of base phenol and solvent is 1：10~2：1, the dosage of the catalyst is the 5~20% of ortho-methyl phenol.
- 7. the application as claimed in claim 4 for being used to prepare the catalyst of adjacent methyl cyclohexanol, it is characterised in that：Catalytic reaction Temperature be 80~180 DEG C, the reaction time is：5~10 hours, the pressure for being passed through hydrogen was 2~6MPa.
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Cited By (4)
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| CN108067238A (en) * | 2018-01-14 | 2018-05-25 | 常州大学 | It is a kind of to prepare metal Co catalysts of cyclohexanol and preparation method thereof for being catalyzed o-methoxyphenol |
| CN111662157A (en) * | 2020-06-18 | 2020-09-15 | 西安工程大学 | Method for synthesizing 2, 6-di-tert-butyl-4-methylcyclohexanol by cobalt catalysis |
| CN115193436A (en) * | 2022-08-22 | 2022-10-18 | 山东明化新材料有限公司 | Nickel-cobalt metal framework catalyst, preparation method and application thereof |
| CN115245841A (en) * | 2022-08-22 | 2022-10-28 | 山东明化新材料有限公司 | Application of nickel-cobalt metal framework catalyst in preparation of 2,2' -bipyridyl |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111662157B (en) * | 2020-06-18 | 2023-07-07 | 西安工程大学 | Method for synthesizing 2, 6-di-tert-butyl-4-methylcyclohexanol by cobalt catalysis |
| CN115193436A (en) * | 2022-08-22 | 2022-10-18 | 山东明化新材料有限公司 | Nickel-cobalt metal framework catalyst, preparation method and application thereof |
| CN115245841A (en) * | 2022-08-22 | 2022-10-28 | 山东明化新材料有限公司 | Application of nickel-cobalt metal framework catalyst in preparation of 2,2' -bipyridyl |
| CN115193436B (en) * | 2022-08-22 | 2024-01-26 | 山东明化新材料有限公司 | Nickel-cobalt metal framework catalyst, preparation method and application thereof |
| CN115245841B (en) * | 2022-08-22 | 2024-01-26 | 山东明化新材料有限公司 | Application of nickel-cobalt metal framework catalyst in preparation of 2,2' -bipyridine |
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Application publication date: 20180105 |
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| RJ01 | Rejection of invention patent application after publication |