CN109420510A - A kind of preparing cyclohexane by hydrogenating benzene catalyst and preparation method thereof - Google Patents
A kind of preparing cyclohexane by hydrogenating benzene catalyst and preparation method thereof Download PDFInfo
- Publication number
- CN109420510A CN109420510A CN201710733084.3A CN201710733084A CN109420510A CN 109420510 A CN109420510 A CN 109420510A CN 201710733084 A CN201710733084 A CN 201710733084A CN 109420510 A CN109420510 A CN 109420510A
- Authority
- CN
- China
- Prior art keywords
- catalyst
- hours
- ruthenium
- cobalt
- temperature
- 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.)
- Pending
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8913—Cobalt and noble metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/16—Reducing
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/10—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of aromatic six-membered rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
Bimetallic catalyst preparation method is estimated the invention discloses a kind of activated carbon supported ruthenium and generates the application in hexamethylene reaction in benzene hydrogenation, it include: ruthenium compound and cobalt metal compound to be configured to deionized water or ethanol solution in proportion, and this is immersed on modified active carbon；It is added dropwise to appropriate reducing agent after the drying after generating bubble, through being separated by solid-liquid separation, by solid catalyst precarsor obtained by drying；Catalyst is obtained after it is roasted under an atmosphere of hydrogen.With this catalyst in lower temperature, its preferable catalytic activity and selectivity are shown when converting hexamethylene for benzene compared with low hydrogen pressure.The catalyst preparation is simple, and raw material is easy to get and precious metal raw material uses less, thus has preferable industrial applications prospect.
Description
Technical field
The invention belongs to chemical catalyst development fields, and in particular to a kind of preparing cyclohexane by hydrogenating benzene catalyst.
Background technique
Hexamethylene is a kind of important Organic Chemicals, and 90% is used to produce ethanedioic acid, caprolactam.Furthermore hexamethylene
Or the fine solvent of cellulose ether, resin, cured, grease, rubber, pitch, is organic synthesis and crystallization medium, is coating and clear
The remover etc. of paint.The method of industrial production hexamethylene can be divided into two classes: the fractionation method for refining of benzene hydrogenation method and petroleum hydrocarbon-fraction.
Wherein catalytic benzene hydrogenation method is the primary synthetic methods of hexamethylene, and catalyst is the principal element for influencing reaction.According to work
Property component difference custom catalysts can be divided mainly into nickel system and noble metal catalyst.
Nickel system benzene hydrogenating catalyst is that catalytic activity is good, cheap with the reason on most benzol hydro refining units at home,
And mature production technology has been formed, such as the Ni-based homogeneous Ziegler type of Sinopec Group's HC-402-2 type
Complex catalyst.There is although nickel catalyst is cheap but also distinct disadvantage: if Sulfur tolerance and thermal stability are poor, catalyst
Service life is short, and active temperature region is narrow, is easy to result in blockage to reactor, abrasion cycles equipment etc..
Noble metal catalyst is broadly divided into two classes: platinum group catalyst and ruthenium catalyst, has resistant to sulfur heat resistance good, in
Renewable after poison, product cyclohexane selectivity is high, and product is not required to the advantages that be separated, and is widely adopted on large-scale plant,
But the expensive application for also making it and development are by a degree of restriction.As Nan Hua group researcher successfully opens at home
NGH-1 type platinum group benzene hydrogenating catalyst is sent out, and builds up first using domestic platinum group benzene hydrogenating catalyst process units.Its shortcomings that
In addition to price height, catalyst preparation process is cumbersome outer, the problems such as reduction there is also reaction condition in the production process of hexamethylene.
Chinese patent (CN200819114789.7) describes platinum cobalt benzene hydrogenating catalyst preparation method, though the catalyst exists
Reaction condition is low in hexamethylene production, but the preparation process step of catalyst is more, and total conversion is not high, such as reacts on a fixed bed
90 minutes, maximum conversion only had 32% in example.
Chinese patent (CN201210470139.3) describes the preparation method of ruthenium system benzene hydrogenating catalyst, which urges
It is higher to change activity and selectivity, but the usage amount of noble ruthenium is more, and reaction condition does not also reduce in hexamethylene production.
Summary of the invention
For existing these problems, the present invention provides the preparations of a kind of activated carbon supported ruthenium, cobalt dual-metal catalyst
Method and its application, which can generate hexamethylene by catalytic benzene hydrogenation under low temperature, low pressure, and have preferable stability,
It is suitble to industrial applications.
The technical solution adopted by the present invention are as follows: preparing cyclohexane by hydrogenating benzene catalyst, it is characterised in that the activity of catalyst
Group is divided into ruthenium and cobalt, and carrier is active carbon；Active component precursor salt is impregnated into carrier using equi-volume impregnating by catalyst
On, then preceding body salt is restored using wet reducing method to obtain catalyst precarsor, then roast up to catalyst catalyst precarsor.
Each component ruthenium, cobalt, quality of activated carbon ratio 1:20-200:150-2000 in the catalyst.
The active carbon is modified activated carbon, carries out extraction to active carbon with supercritical methanol and chemical reaction acts on, will
Surface layer and secondary surface layer organic matter clean activated carbon surface carboxyl and the unstable group of other oxygen-containing acid after extracting.
The preparation method of catalyst of the present invention includes the following steps:
(1) soluble ruthenium salt and cobalt salt are configured to maceration extract；
(2) it on maceration extract incipient impregnation to modified activated carbon, is dried after dipping is stirred at room temperature, obtains catalyst Precursors；
(3) prepared reducing agent solution is added in above-mentioned catalyst Precursors and is restored 0.5-6 hours, through washing after removing liquid
It washs, dry and obtain catalyst precarsor；
(4) up to ruthenium and cobalt dual-metal benzene hydrogenating catalyst after above-mentioned catalyst precarsor being roasted.
In the step (1), ruthenium salt is one of ruthenium trichloride, nitric acid ruthenium and acetic acid ruthenium, and the cobalt salt is acetic acid
One of cobalt, cobalt chloride, cobalt nitrate and cobaltous sulfate.
In the step (2), mixing time 3-6 hours, 10 DEG C -90 DEG C of dipping temperature, dip time 8-12 hours, drying
90 DEG C -120 DEG C of temperature, drying time 8-16 hours.
In the step (3), reducing agent is one of formaldehyde, hydrazine class compound, sodium borohydride, potassium borohydride or more
Kind, the concentration of reducing agent is 0.2-4.0mol/L, and washing is with distilled water or to be washed with deionized to pH=7.0, drying temperature
90 DEG C -120 DEG C, drying time 8-16 hours.
In the step (3), reduction process reaction temperature is 0 DEG C -90 DEG C.
In the step (4), maturing temperature is 200 DEG C -800 DEG C, calcining time 3-6 hours.
Catalyst provided by the invention is used for during producing cyclohexane by adding hydrogen in benzene, reaction pressure 0.2MPa-4.0MPa,
80 DEG C -150 DEG C of reaction temperature, liquid air speed 0.5-10h-1, H2/C6H6Molar ratio is 3.0-800 mol/mol, and preferably pressure is
1.0MPa, 110 DEG C of reaction temperature, liquid air speed 2.0h-1, H2/C6H6For 60/1 mol/mol.
Beneficial effect of the present invention: prepared by the method activated carbon supported ruthenium, cobalt dual-metal catalyst can be low
Efficient catalytic producing cyclohexane by adding hydrogen in benzene under temperature, low pressure, the catalyst have thermal stability good, and what can be repeatedly used is superior
Performance is suitable for industrialized production.
Specific embodiment
Technical solution of the present invention is clearly and completely described below in conjunction with specific embodiment, it is clear that described embodiment
Only a part of the embodiment of the present invention, rather than whole embodiments.Based on embodiment ordinary skill people in the present invention
Member's obtained embodiment without making creative work, shall fall within the protection scope of the present invention.
Embodiment 1
A kind of preparation method of activated carbon supported ruthenium, cobalt dual-metal catalyst, comprising the following steps:
The first step, the modification of active carbon
It carries out certain extraction and chemical reaction to appropriate cocoanut active charcoal with supercritical methanol to act on, by surface layer and secondary surface layer
Organic matter takes clearly the unstable group of the oxygen-containing acid such as activated carbon surface carboxyl after extracting；
Second step weighs the ruthenium trichloride of 0.02g containing ruthenium, and the cobalt nitrate of 2.5g containing cobalt prepares the aqueous solution of dipping, by incipient impregnation
Onto 40g modified activated carbon, dipping temperature is 60 DEG C in dipping process, and stirring terminates after 4 hours and continues to impregnate to 10 hours,
Then the drying in 10 hours at 105 DEG C；
Compound concentration is to be added to above-mentioned catalyst at 2.0mol/L solution of potassium borohydride reducing agent is 60 DEG C in temperature by third step
It restores 3 hours on parent, is washed through deionized water washing to PH=7.0 after removing liquid, it is small in 105 DEG C of holdings of temperature dry 12
When obtain catalyst precarsor；
Above-mentioned catalyst precarsor is catalyzed after roasting temperature 4 hours by the 4th step at 300 DEG C up to ruthenium and cobalt dual-metal benzene hydrogenation
Agent.
The evaluation of catalyst carries out on high-pressure hydrogenation micro anti-evaluation device, and 20ml catalyst is taken to be packed into reactor, catalysis
Appropriate porcelain ball, reaction raw materials liquid benzene and hydrogen are loaded by entering reactor above reactor in position to bed up and down, and product is by reacting
Device bottom enters products pot after high pressure, low pressure separation pot.Reaction condition: pressure 1.0MPa, 110 DEG C of reaction temperature, liquid
Air speed 2.0h-1, H2/C6H6Than for 60/1 (mol/mol).Evaluating catalyst result data is shown in Table i.e. evaluating catalyst table and (is derived from 24
Stablize data after hour).
Embodiment 2
It is activated carbon modified to see embodiment 1.
The ruthenium trichloride of 0.02g containing ruthenium is weighed, the cobalt nitrate of 4g containing cobalt prepares the aqueous solution of dipping, by incipient impregnation to 40g
On modified activated carbon, dipping temperature is 60 DEG C in dipping process, and stirring terminates after 4 hours and continues dipping to 10 hours, then
The drying in 10 hours at 105 DEG C.It is to be added at 0.5mol/L solution of potassium borohydride reducing agent is 30 DEG C in temperature by compound concentration
It is restored 3 hours on above-mentioned catalyst Precursors, washs through deionized water washing to PH=7.0 after removing liquid, protected at 105 DEG C of temperature
It holds dry 12 hours and obtains catalyst precarsor.By above-mentioned catalyst precarsor 450 DEG C after roasting temperature 4 hours up to ruthenium and cobalt
Bimetallic benzene hydrogenating catalyst.
Evaluating catalyst is shown in embodiment 1.
Embodiment 3
It is activated carbon modified to see embodiment 1.
The ruthenium trichloride of 0.02g containing ruthenium is weighed, the cobalt nitrate of 6g containing cobalt prepares the aqueous solution of dipping, by incipient impregnation to 40g
On modified activated carbon, dipping temperature is 60 DEG C in dipping process, and stirring terminates after 4 hours and continues dipping to 10 hours, then
The drying in 10 hours at 105 DEG C.It is to be added at 1.0mol/L solution of potassium borohydride reducing agent is 50 DEG C in temperature by compound concentration
It is restored 3 hours on above-mentioned catalyst Precursors, washs through deionized water washing to PH=7.0 after removing liquid, protected at 105 DEG C of temperature
It holds dry 12 hours and obtains catalyst precarsor.By above-mentioned catalyst precarsor 600 DEG C after roasting temperature 4 hours up to ruthenium and cobalt
Bimetallic benzene hydrogenating catalyst.
Evaluating catalyst is shown in embodiment 1.
Embodiment 4
The ruthenium trichloride of 0.025g containing ruthenium is weighed, the cobalt nitrate of 2.5g containing cobalt is prepared the aqueous solution of dipping, changed by incipient impregnation to 40g
Property active carbon on, in dipping process dipping temperature be 60 DEG C, stirring 4 hours after terminate and continue dipping to 10 hours, then exist
Drying in 10 hours at 105 DEG C.It is to be added at 2.0mol/L solution of potassium borohydride reducing agent is 30 DEG C in temperature by compound concentration
It states and is restored 3 hours on catalyst Precursors, wash through deionized water washing to PH=7.0 after removing liquid, kept at 105 DEG C of temperature
Obtain catalyst precarsor within dry 12 hours.By above-mentioned catalyst precarsor 300 DEG C after roasting temperature 4 hours it is double up to ruthenium and cobalt
Metal benzene hydrogenating catalyst.
Evaluating catalyst is shown in embodiment 1.
Embodiment 5
It is activated carbon modified to see embodiment 1.
The ruthenium trichloride of 0.025g containing ruthenium is weighed, the cobalt nitrate of 4g containing cobalt prepares the aqueous solution of dipping, by incipient impregnation to 40g
On modified activated carbon, dipping temperature is 60 DEG C in dipping process, and stirring terminates after 4 hours and continues dipping to 10 hours, then
The drying in 10 hours at 105 DEG C.It is to be added at 1.0mol/L solution of potassium borohydride reducing agent is 50 DEG C in temperature by compound concentration
It is restored 3 hours on above-mentioned catalyst Precursors, washs through deionized water washing to PH=7.0 after removing liquid, protected at 105 DEG C of temperature
It holds dry 12 hours and obtains catalyst precarsor.By above-mentioned catalyst precarsor 450 DEG C after roasting temperature 4 hours up to ruthenium and cobalt
Bimetallic benzene hydrogenating catalyst.
Evaluating catalyst is shown in embodiment 1.
Embodiment 6
It is activated carbon modified to see embodiment 1.
The ruthenium trichloride of 0.025g containing ruthenium is weighed, the cobalt nitrate of 6g containing cobalt prepares the aqueous solution of dipping, by incipient impregnation to 40g
On modified activated carbon, dipping temperature is 60 DEG C in dipping process, and stirring terminates after 4 hours and continues dipping to 10 hours, then
The drying in 10 hours at 105 DEG C.It is to be added at 0.5mol/L solution of potassium borohydride reducing agent is 60 DEG C in temperature by compound concentration
It is restored 3 hours on above-mentioned catalyst Precursors, washs through deionized water washing to PH=7.0 after removing liquid, protected at 105 DEG C of temperature
It holds dry 12 hours and obtains catalyst precarsor.By above-mentioned catalyst precarsor 600 DEG C after roasting temperature 4 hours up to ruthenium and cobalt
Bimetallic benzene hydrogenating catalyst.
Evaluating catalyst is shown in embodiment 1.
Embodiment 7
It is activated carbon modified to see embodiment 1.
The ruthenium trichloride of 0.04g containing ruthenium is weighed, the cobalt nitrate of 2.5g containing cobalt is prepared the aqueous solution of dipping, arrived by incipient impregnation
On 40g modified activated carbon, dipping temperature is 60 DEG C in dipping process, and stirring terminates after 4 hours and continues dipping to 10 hours, so
The drying in 10 hours at 105 DEG C afterwards.It is to add at 0.5mol/L solution of potassium borohydride reducing agent is 60 DEG C in temperature by compound concentration
It restores 3 hours on to above-mentioned catalyst Precursors, is washed through deionized water washing to PH=7.0, at 105 DEG C of temperature after removing liquid
It keeps obtaining catalyst precarsor in dry 12 hours.By above-mentioned catalyst precarsor 300 DEG C after roasting temperature 4 hours up to ruthenium and
Cobalt dual-metal benzene hydrogenating catalyst.
Evaluating catalyst is shown in embodiment 1.
Embodiment 8
It is activated carbon modified to see embodiment 1.
The ruthenium trichloride of 0.04g containing ruthenium is weighed, the cobalt nitrate of 4g containing cobalt prepares the aqueous solution of dipping, by incipient impregnation to 40g
On modified activated carbon, dipping temperature is 60 DEG C in dipping process, and stirring terminates after 4 hours and continues dipping to 10 hours, then
The drying in 10 hours at 105 DEG C.It is to be added at 1.0mol/L solution of potassium borohydride reducing agent is 60 DEG C in temperature by compound concentration
It is restored 3 hours on above-mentioned catalyst Precursors, washs through deionized water washing to PH=7.0 after removing liquid, protected at 105 DEG C of temperature
It holds dry 12 hours and obtains catalyst precarsor.By above-mentioned catalyst precarsor 450 DEG C after roasting temperature 4 hours up to ruthenium and cobalt
Bimetallic benzene hydrogenating catalyst.
Evaluating catalyst is shown in embodiment 1.
Embodiment 9
It is activated carbon modified to see embodiment 1.
The ruthenium trichloride of 0.04g containing ruthenium is weighed, the cobalt nitrate of 6g containing cobalt prepares the aqueous solution of dipping, by incipient impregnation to 40g
On modified activated carbon, dipping temperature is 60 DEG C in dipping process, and stirring terminates after 4 hours and continues dipping to 10 hours, then
The drying in 10 hours at 105 DEG C.It is to be added at 2.0mol/L solution of potassium borohydride reducing agent is 30 DEG C in temperature by compound concentration
It is restored 3 hours on above-mentioned catalyst Precursors, washs through deionized water washing to PH=7.0 after removing liquid, protected at 105 DEG C of temperature
It holds dry 12 hours and obtains catalyst precarsor.By above-mentioned catalyst precarsor 600 DEG C after roasting temperature 4 hours up to ruthenium and cobalt
Bimetallic benzene hydrogenating catalyst.
Evaluating catalyst is shown in embodiment 1.
Evaluating catalyst table
| Sample source | Conversion ratio (%) | Selectivity (%) |
| Embodiment 1 | 96.0 | 97.5 |
| Embodiment 2 | 98.5 | 98.0 |
| Embodiment 3 | 92.0 | 90.0 |
| Embodiment 4 | 99.0 | 99.2 |
| Embodiment 5 | 99.9 | 100 |
| Embodiment 6 | 98.5 | 89.0 |
| Embodiment 7 | 99.2 | 99.9 |
| Embodiment 8 | 99.8 | 99.9 |
| Embodiment 9 | 95.6 | 91.6 |
Claims (10)
1. a kind of preparing cyclohexane by hydrogenating benzene catalyst, it is characterised in that the active component of catalyst is ruthenium and cobalt, and carrier is to live
Property charcoal；Catalyst is impregnated into active component precursor salt on carrier using equi-volume impregnating, then uses wet reducing method
Preceding body salt is restored to obtain catalyst precarsor, then catalyst precarsor is roasted up to catalyst.
2. catalyst according to claim 1, it is characterised in that each component ruthenium, cobalt, quality of activated carbon ratio 1:20- in catalyst
200:150-2000。
3. catalyst according to claim 1, it is characterised in that active carbon is modified activated carbon, with supercritical methanol to activity
Charcoal carry out extraction and chemical reaction effect, by surface layer and secondary surface layer organic matter cleaned after extracting activated carbon surface carboxyl and
The unstable group of other oxygen-containing acid.
4. the preparation method of catalyst includes the following steps: according to claim 1
(1) soluble ruthenium salt and cobalt salt are configured to maceration extract；
(2) it on maceration extract incipient impregnation to modified activated carbon, is dried after dipping is stirred at room temperature, obtains catalyst Precursors；
(3) prepared reducing agent solution is added in above-mentioned catalyst Precursors and is restored 0.5-6 hours, through washing after removing liquid
It washs, dry and obtain catalyst precarsor；
(4) up to ruthenium and cobalt dual-metal benzene hydrogenating catalyst after above-mentioned catalyst precarsor being roasted.
5. method for preparing catalyst according to claim 4, it is characterised in that ruthenium salt described in step (1) be ruthenium trichloride,
One of nitric acid ruthenium and acetic acid ruthenium, the cobalt salt are one of cobalt acetate, cobalt chloride, cobalt nitrate and cobaltous sulfate.
6. method for preparing catalyst according to claim 4, it is characterised in that step (2) described mixing time 3-6 hours, leaching
10 DEG C -90 DEG C of stain temperature, dip time 8-12 hours, 90 DEG C -120 DEG C of drying temperature, drying time 8-16 hours.
7. method for preparing catalyst according to claim 4, it is characterised in that step (3) reducing agent is formaldehyde, hydrazine
One or more of compound, sodium borohydride, potassium borohydride, the concentration of reducing agent are 0.2-4.0mol/L, and washing is to use
Distilled water is washed with deionized to pH=7.0,90 DEG C -120 DEG C of drying temperature, drying time 8-16 hours.
8. method for preparing catalyst according to claim 4, it is characterised in that step (3) the reduction process reaction temperature is
0℃-90℃。
9. method for preparing catalyst according to claim 4, it is characterised in that step (4) maturing temperature be 200 DEG C-
800 DEG C, calcining time 3-6 hours.
10. catalyst according to claim 1, it is characterized in that for during producing cyclohexane by adding hydrogen in benzene, reaction pressure
0.2MPa-4.0MPa, 80 DEG C -150 DEG C of reaction temperature, liquid air speed 0.5-10h-1, H2/C6H6Molar ratio is 3.0-800 mol/
mol。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710733084.3A CN109420510A (en) | 2017-08-24 | 2017-08-24 | A kind of preparing cyclohexane by hydrogenating benzene catalyst and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710733084.3A CN109420510A (en) | 2017-08-24 | 2017-08-24 | A kind of preparing cyclohexane by hydrogenating benzene catalyst and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109420510A true CN109420510A (en) | 2019-03-05 |
Family
ID=65500807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710733084.3A Pending CN109420510A (en) | 2017-08-24 | 2017-08-24 | A kind of preparing cyclohexane by hydrogenating benzene catalyst and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109420510A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110627606A (en) * | 2019-08-27 | 2019-12-31 | 浙江工业大学 | Application of carbon nano tube embedded metal particle catalyst in reaction of synthesizing cyclohexane by benzene selective catalytic hydrogenation |
| CN110665522A (en) * | 2019-08-27 | 2020-01-10 | 浙江工业大学 | Application of catalyst for depositing metal particles in carbon nano tube in reaction of synthesizing cyclohexane through selective catalytic hydrogenation of benzene |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030121826A1 (en) * | 2002-01-03 | 2003-07-03 | Yunjie Ding | Activated carbon supported cobalt based catalyst for direct conversion of synthesis gas to diesel fuels |
| CN1457923A (en) * | 2002-12-25 | 2003-11-26 | 南化集团研究院 | Platinum catalyst for preparing cyclohexane by hydrogenating benzene and its preparing process |
| CN101239888A (en) * | 2008-03-10 | 2008-08-13 | 上海华谊丙烯酸有限公司 | Method for preparing isobutyl alcohol by methylacrolein hydrogenation |
| CN101289365A (en) * | 2008-06-03 | 2008-10-22 | 北京大学 | Low-temperature catalytic benzene hydrogenation method and special catalyst thereof |
| CN101549292A (en) * | 2009-05-08 | 2009-10-07 | 西安凯立化工有限公司 | Catalyst for synthesizing cyclohexene by hydrogenation of benzene ring and preparing method thereof |
-
2017
- 2017-08-24 CN CN201710733084.3A patent/CN109420510A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030121826A1 (en) * | 2002-01-03 | 2003-07-03 | Yunjie Ding | Activated carbon supported cobalt based catalyst for direct conversion of synthesis gas to diesel fuels |
| CN1457923A (en) * | 2002-12-25 | 2003-11-26 | 南化集团研究院 | Platinum catalyst for preparing cyclohexane by hydrogenating benzene and its preparing process |
| CN101239888A (en) * | 2008-03-10 | 2008-08-13 | 上海华谊丙烯酸有限公司 | Method for preparing isobutyl alcohol by methylacrolein hydrogenation |
| CN101289365A (en) * | 2008-06-03 | 2008-10-22 | 北京大学 | Low-temperature catalytic benzene hydrogenation method and special catalyst thereof |
| CN101549292A (en) * | 2009-05-08 | 2009-10-07 | 西安凯立化工有限公司 | Catalyst for synthesizing cyclohexene by hydrogenation of benzene ring and preparing method thereof |
Non-Patent Citations (2)
| Title |
|---|
| A.B.史泰尔斯 等: "《催化剂载体与负载型催化剂》", 31 March 1992, 中国石化出版社 * |
| 徐三魁等: "不同状态甲醇改性活性炭对其表面性质及葡萄糖加氢Ru/C催化性能的影响", 《河南工业大学学报》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110627606A (en) * | 2019-08-27 | 2019-12-31 | 浙江工业大学 | Application of carbon nano tube embedded metal particle catalyst in reaction of synthesizing cyclohexane by benzene selective catalytic hydrogenation |
| CN110665522A (en) * | 2019-08-27 | 2020-01-10 | 浙江工业大学 | Application of catalyst for depositing metal particles in carbon nano tube in reaction of synthesizing cyclohexane through selective catalytic hydrogenation of benzene |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105289592B (en) | It is catalyzed method of the levulic acid Hydrogenation for γ valerolactones | |
| CN101347737B (en) | Selective hydrogenation catalyst of aromatic aldehydes for refinement of terephthalic acid | |
| CN101733123B (en) | Acid-proof catalyst for preparing gamma-valerolactone from levulinic acid, preparation method and application | |
| CN103785408B (en) | A kind of prepared by dimethyl oxalate plus hydrogen is for catalyst and the synthetic method of methyl glycollate | |
| CN101767016B (en) | Aromatic aldehyde selective hydrogenation catalyst for refining terephthalic acid | |
| CN105536779B (en) | A kind of preparation method of Pd/TiO2 nano-wire catalyst, catalyst obtained and its application | |
| CN103848719B (en) | Method for preparing 1,5-pentanediol via selective hydrogenolysis of tetrahydrofurfuryl alcohol | |
| CN103752306B (en) | Preparation method of a kind of prepared from benzene and hydrogen thiacyclohexane catalyst and products thereof and application | |
| CN109420510A (en) | A kind of preparing cyclohexane by hydrogenating benzene catalyst and preparation method thereof | |
| CN101367041A (en) | Preparation of solid base catalyst, uses of the same in hydroxide aldehyde condensation reaction | |
| WO2020192477A1 (en) | Catalyst and method for preparing isopentyl diol | |
| CN106944050B (en) | A kind of catalyst and its preparation method and application synthesizing 1,3- propylene glycol | |
| CN108325535B (en) | Catalyst for preparing n-propanol by hydrogenolysis of glycerol and preparation and use methods thereof | |
| CN101830787B (en) | Method for synthesizing methyl isobutyl ketone and diisobutyl ketone by acetone gas-phase one-step method | |
| CN106890669B (en) | A kind of catalyst producing methyl acetate, preparation method and application | |
| CN105732329B (en) | A kind of synthetic method of 2,2,4,4- tetramethyls -1,3- cyclobutanediols | |
| CN101428226A (en) | Selective hydrogenation catalyst for fine purification of p-benzene dicarboxylic acid | |
| CN103785375A (en) | Catalyst for synthesis of methanol and formaldehyde through selective oxidation of methane, and preparation method and application thereof | |
| CN102886269B (en) | Catalyst for synthesizing crotyl alcohol by crotonic aldehyde through gas phase selective hydrogenating and preparation method | |
| CN102746113B (en) | Preparation method of isopropanol | |
| CN111420657A (en) | Ru-based catalyst for synthesizing 3-pentanone through ethylene conversion and preparation method and application thereof | |
| CN100584813C (en) | Method for preparing terephthalyl alcohol by hydrogenation of terephthalic acid | |
| CN104028302B (en) | One grows flax the preparation method of loaded with nano Pd-Ni catalyst and application | |
| CN109225329B (en) | Catalyst for preparing 1, 3-propylene glycol by hydrogenolysis of glycerol and application thereof | |
| CN112028728B (en) | Method for preparing cyclohexanol and cyclohexane by catalytic hydrogenation of diphenyl ether |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190305 |
|
| RJ01 | Rejection of invention patent application after publication |