CN116173963B - Catalyst for preparing mesitylene by pseudocumene isomerization and preparation method thereof - Google Patents
Catalyst for preparing mesitylene by pseudocumene isomerization and preparation method thereof Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims abstract description 63
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 title claims abstract description 60
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 238000006317 isomerization reaction Methods 0.000 title claims abstract description 18
- 239000003999 initiator Substances 0.000 claims abstract description 38
- 239000002159 nanocrystal Substances 0.000 claims abstract description 37
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims description 62
- 239000008367 deionised water Substances 0.000 claims description 38
- 229910021641 deionized water Inorganic materials 0.000 claims description 38
- 238000001027 hydrothermal synthesis Methods 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- 238000002156 mixing Methods 0.000 claims description 24
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 claims description 23
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 20
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 claims description 13
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical group [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 claims description 13
- 238000005406 washing Methods 0.000 claims description 11
- 229910052782 aluminium Inorganic materials 0.000 claims description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- 229910052759 nickel Inorganic materials 0.000 claims description 10
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims description 9
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 9
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims description 9
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical group [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 claims description 9
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical group [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 claims description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 8
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000002131 composite material Substances 0.000 abstract description 28
- 239000002253 acid Substances 0.000 abstract description 26
- 238000006243 chemical reaction Methods 0.000 abstract description 15
- 230000003197 catalytic effect Effects 0.000 abstract description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 4
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- 239000013078 crystal Substances 0.000 abstract description 2
- 239000006185 dispersion Substances 0.000 abstract description 2
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 238000012512 characterization method Methods 0.000 description 29
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
- 229910021529 ammonia Inorganic materials 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 238000002441 X-ray diffraction Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001833 catalytic reforming Methods 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
Classifications
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- 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
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2729—Changing the branching point of an open chain or the point of substitution on a ring
- C07C5/2732—Catalytic processes
- C07C5/2735—Catalytic processes with metal oxides
-
- 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
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
-
- 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
- B01J23/74—Iron group metals
- B01J23/755—Nickel
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/20—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state
- B01J35/23—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state in a colloidal state
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/617—500-1000 m2/g
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- 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
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0018—Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)
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- 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
- B01J37/03—Precipitation; Co-precipitation
- B01J37/036—Precipitation; Co-precipitation to form a gel or a cogel
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- 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
- B01J37/08—Heat treatment
- B01J37/10—Heat treatment in the presence of water, e.g. steam
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- C07C2523/74—Iron group metals
- C07C2523/755—Nickel
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Abstract
The invention discloses a catalyst for preparing mesitylene by using pseudocumene isomerization and a preparation method thereof, which firstly adopts a nanocrystal initiator method to prepare nano Al 2 O 3 Due to the addition of the nanocrystal initiator, the NiO composite catalyst forms a large amount of crystal nuclei in the preparation process and is highly uniformly dispersed, thereby being beneficial to forming Al with uniform grain size, nanoscale, high crystallinity, high dispersion and high yield 2 O 3 -NiO composite catalyst. The catalyst has small grain size, large specific surface area, large number of exposed catalytic active sites, and long catalytic life, and the acidity is mainly medium strong acid, so that carbon deposit is not easy to generate. The specific surface area is large, so that the raw materials are easily adsorbed on the surface of the catalyst and fully contacted with the catalytic active site; the catalyst has high catalytic activity, so that the reaction temperature is low, the reaction energy consumption is reduced, and the conversion rate of the pseudocumene and the yield of the mesitylene are high.
Description
Technical Field
The invention belongs to the technical field of solid acid catalytic material preparation, and particularly relates to a catalyst for preparing mesitylene by using pseudocumene isomerization and a preparation method thereof.
Background
Mesitylene is an important organic chemical raw material, can be used for producing various dye intermediates such as trimesic acid, pyromellitic anhydride and the like, and can also be used for producing antioxidants, polyester resin curing agents, stabilizers, alkyd resin plasticizers and the like; and is a solvent with good performance, and can be used as a developer of a silicone photosensitive sheet in the electronic industry. Mesitylene can be obtained by separating C9 aromatic hydrocarbon, but the common rectification separation is difficult because the boiling point of mesitylene is similar to that of o-methyl ethyl benzene; the catalyst can also be prepared by dehydration reaction of acetone under the catalysis of sulfuric acid, but the yield is lower, and the problems of equipment corrosion and the like exist. The C9-C10 aromatic hydrocarbon obtained by catalytic reforming or naphtha cracking contains a large amount of pseudocumene, and the preparation of the mesitylene by isomerizing the pseudocumene is an effective way for high-value utilization of the pseudocumene.
At present, in the technology for preparing the mesitylene by the isomerization of the pseudocumene, most of the used catalysts are molecular sieves, or the noble metal and other catalysts are loaded on the molecular sieves, so that the preparation process is complicated, the condition is complex, the cost is high, the defects of low pseudocumene conversion rate, low mesitylene yield and the like exist, and the large-scale industrialization difficulty is high. Therefore, the research and development of the catalyst with high conversion rate of the pseudocumene and high yield of the mesitylene, simple preparation process and low cost is a key for realizing the large-scale industrialization of the technology for preparing the mesitylene by the pseudocumene isomerization.
Disclosure of Invention
The invention aims to: aiming at the problems of complex preparation method, higher cost, lower conversion rate of the pseudocumene, lower yield of the pseudocumene and the like in the existing technology for preparing the mesitylene by the pseudocumene isomerization, the invention provides the preparation method of the catalyst for preparing the mesitylene by the pseudocumene isomerization, which is simple and has high conversion rate of the pseudocumene and high yield of the mesitylene.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
a preparation method of a catalyst for preparing mesitylene by using pseudocumene isomerization, which comprises the following steps:
(1) Preparation of nanocrystal initiators: mixing an aluminum source, a nickel source, a template agent, ammonia water and deionized water, uniformly stirring at room temperature, and then performing hydrothermal reaction to obtain a nanocrystal initiator;
(2) Mixing an aluminum source, a template agent, ammonia water and deionized water, and uniformly stirring at room temperature to obtain a solution A;
(3) Mixing a nickel source with deionized water, and uniformly stirring at room temperature to obtain a solution B;
(4) Synchronously dripping the solution B and the nanocrystal initiator obtained in the step (1) into the solution A, and stirring to form sol-gel;
(5) Carrying out hydrothermal reaction on the sol-gel obtained in the step (4) at the temperature of 100-150 ℃ for 24-72 h;
(6) Filtering, washing and drying the hydrothermal reaction product obtained in the step (5), and finally roasting at 500-550 ℃ for 1-3 hours to obtain the catalyst.
Further, in the step (1), the aluminum source is aluminum nitrate, aluminum isopropoxide or aluminum chloride, and the amount of the aluminum source is Al 2 O 3 Calculating; the nickel source is nickel nitrate or nickel chloride, and the dosage is calculated by NiO; the dosage of the ammonia water is NH 3 Calculating; the template agent is tetraethylammonium hydroxide, tetrapropylammonium hydroxide or tetrabutylammonium hydroxide;
the raw materials are NiO to Al according to the mole ratio 2 O 3 Template agent NH 3 :H 2 O=1 (1.5-3), 1.5-3, 2-3, 20-80, stirring speed is 60-80 r/min, and stirring time is controlled to be 1-3 h.
Further, in the step (1), the temperature of the hydrothermal reaction is controlled to be 40-60 ℃, and the hydrothermal reaction time is 1-3 days.
Further, in the step (2), the aluminum source is aluminum nitrate, aluminum isopropoxide or aluminum chlorideAluminum, the dosage is Al 2 O 3 Calculating; the dosage of the ammonia water is NH 3 Calculating; the template agent is tetraethylammonium hydroxide, tetrapropylammonium hydroxide or tetrabutylammonium hydroxide;
the raw materials are Al according to the mole ratio 2 O 3 Template agent NH 3 :H 2 O=1, (0.5-2) 0.6-2, (6-53) and stirring for 1-3 h at room temperature at the stirring rate of 60-80 r/min.
Further, in the step (3), the nickel source is nickel nitrate or nickel chloride, and the dosage is calculated by NiO; the nickel source and deionized water are NiO to H in a mole ratio 2 O=1, (20-50) and stirring for 1-3 h at room temperature at a stirring rate of 60-80 r/min.
Further, in the step (4), the usage amount of the nanocrystal initiator is 1.0-10.0% of the total mass of the solution A and the solution B; the mass ratio of the solution A to the solution B is 1.8-2.3.
Further, in the step (4), the solution B and the nanocrystal initiator are synchronously added into the solution A in a dropwise manner at a dropwise rate of 0.1-0.6 mL/min, and then stirred for 3-5 h at a stirring rate of 80-120 r/min at a temperature of 40-60 ℃ to form sol-gel.
Further, in the step (5), deionized water is adopted for washing until the pH value of the filtrate is 7.0; drying is carried out for 12-24 h at 100-120 ℃.
Further, the catalyst for preparing mesitylene by the isomerization of the pseudocumene, which is prepared by the preparation method, is also in the protection scope of the invention.
Furthermore, the invention also claims the application of the catalyst in preparing mesitylene by using the pseudocumene isomerization.
The beneficial effects are that:
the invention adopts the nano crystal initiator method to prepare nano Al for the first time 2 O 3 Due to the addition of the nanocrystal initiator, the NiO composite catalyst forms a large amount of crystal nuclei in the preparation process and is highly uniformly dispersed, thereby being beneficial to forming Al with uniform grain size, nanoscale, high crystallinity, high dispersion and high yield 2 O 3 -NiO composite catalyst. The catalyst has small grain size, large specific surface area, large number of exposed catalytic active sites, and long catalytic life, and the acidity is mainly medium strong acid, so that carbon deposit is not easy to generate. The specific surface area is large, so that the raw materials are easily adsorbed on the surface of the catalyst and fully contacted with the catalytic active site; the catalyst has high catalytic activity, so that the reaction temperature is low, the reaction energy consumption is reduced, and the conversion rate of the pseudocumene and the yield of the mesitylene are high.
Drawings
The foregoing and/or other advantages of the invention will become more apparent from the following detailed description of the invention when taken in conjunction with the accompanying drawings and detailed description.
FIG. 1 shows Al prepared in example 4 and comparative example 2 O 3 XRD pattern of NiO composite catalyst.
FIG. 2 shows Al prepared in example 4 and comparative example 2 O 3 NH of NiO composite catalyst sample 3 -TPD map.
Detailed Description
The invention will be better understood from the following examples.
Example 1
9.2g of nickel nitrate (calculated as NiO) and 8.0g of aluminum nitrate (calculated as Al) 2 O 3 Calculated, 30.5g of tetraethylammonium hydroxide (TPAOH), 6.8g of ammonia (amount NH) 3 Calculated) and 18g deionized water, wherein the molar ratio of the deionized water is NiO to Al 2 O 3 :TPAOH:NH 3 :H 2 Mixing O=1:1.5:3:2:20, stirring at room temperature for 2 hours at a stirring rate of 80r/min, transferring into a hydrothermal reaction kettle, and carrying out hydrothermal reaction at 60 ℃ for 1 day to obtain a nanocrystal initiator; 8.0g of aluminum nitrate (used in Al 2 O 3 Calculated, 30.5g of tetraethylammonium hydroxide (TPAOH), 6.8g of ammonia (amount NH) 3 Calculated by the mol ratio), 18g of deionized water, according to the mol ratio of Al 2 O 3 :TPAOH:NH 3 :H 2 Mixing O=1:2:1.3:13, and stirring for 2 hours at room temperature at a stirring rate of 80r/min to obtain a solution A; 9.2g of nickel nitrate (calculated as NiO) and 18g of deionized water were added in a molar ratio of NiO to H 2 Mixing O=1:20, stirring at room temperature for 1h at a stirring rate of 80r/min to obtainSolution B; the solution B and the nano-crystal initiator are synchronously added into the solution A in a dropwise manner at a dropwise rate of 0.1mL/min, the mass of the nano-crystal initiator is 9.1g, which accounts for 10.0 percent of the total mass of the solution A, B, and the solution B and the nano-crystal initiator are stirred for 3 hours at a stirring rate of 80r/min at a temperature of 60 ℃ to form sol-gel; transferring the sol-gel into a hydrothermal reaction kettle, performing hydrothermal reaction at 100 ℃ for 24 hours, filtering the obtained hydrothermal reaction product, washing with deionized water until the pH value of the filtrate is 7.0, drying at 120 ℃ for 12 hours, and finally roasting at 550 ℃ for 3 hours to obtain Al 2 O 3 -NiO composite catalyst with a yield of 96.1%. For the prepared Al 2 O 3 SEM characterization of the NiO composite catalyst to obtain the grain size; the crystallinity is obtained through XRD characterization; the specific surface area is obtained through BET characterization; by NH 3 -TPD characterization, resulting in acid quantity and acid strength. The characterization results are shown in table 1.
Example 2
6.5g of nickel chloride (calculated as NiO) and 16.0g of aluminum nitrate (calculated as Al) 2 O 3 Calculated), 19.4g tetrabutylammonium hydroxide (TBAOH), 10.2g ammonia (amount NH) 3 Calculated) and 72g deionized water, wherein the molar ratio of the deionized water is NiO to Al 2 O 3 :TBAOH:NH 3 :H 2 Mixing O=1:3:1.5:3:80, stirring at room temperature at a stirring rate of 60r/min for 1h, transferring into a hydrothermal reaction kettle, and carrying out hydrothermal reaction at 40 ℃ for 3 days to obtain a nanocrystal initiator; 16.0g of aluminum nitrate (amount of Al 2 O 3 Calculated), 19.4g tetrabutylammonium hydroxide (TBAOH), 10.2g ammonia (amount NH) 3 Calculated by the mol ratio), 72g of deionized water, according to the mol ratio of Al 2 O 3 :TPAOH:NH 3 :H 2 Mixing O=1:0.5:1:27, and stirring for 1h at room temperature at a stirring rate of 60r/min to obtain a solution A; 6.5g of nickel chloride (calculated as NiO) and 45g of deionized water were added in a molar ratio of NiO to H 2 Mixing O=1:50, and stirring for 1h at room temperature at a stirring rate of 60r/min to obtain a solution B; solution B and nanocrystal initiator were simultaneously added dropwise to solution A at a drop rate of 0.6mL/min, the mass of nanocrystal initiator being 1.7g, 1.0% of the total mass of solution A, B, and at a stirring rate of 80r at 40 ℃Stirring for 3 hours in min to form sol-gel; transferring the sol-gel into a hydrothermal reaction kettle, performing hydrothermal reaction at 150 ℃ for 48 hours, filtering the obtained hydrothermal reaction product, washing with deionized water until the pH value of the filtrate is 7.0, drying at 100 ℃ for 12 hours, and finally roasting at 500 ℃ for 2 hours to obtain Al 2 O 3 -NiO composite catalyst with 97.5% yield. For the prepared Al 2 O 3 SEM characterization of the NiO composite catalyst to obtain the grain size; the crystallinity is obtained through XRD characterization; the specific surface area is obtained through BET characterization; by NH 3 -TPD characterization, resulting in acid quantity and acid strength. The characterization results are shown in table 1.
Example 3
6.5g of nickel chloride (calculated as NiO) and 10.2g of aluminum isopropoxide (calculated as Al) 2 O 3 Calculated), 14.7g tetraethylammonium hydroxide (TEAOH), 8.5g ammonia (in NH) 3 Calculated) and 27g deionized water, wherein the molar ratio of the deionized water is NiO to Al 2 O 3 :TEAOH:NH 3 :H 2 Mixing O=1:2:2:2.5:30, stirring at the stirring rate of 70r/min for 2 hours at room temperature, transferring into a hydrothermal reaction kettle, and carrying out hydrothermal reaction at 50 ℃ for 2 days to obtain a nanocrystal initiator; 10.2g of aluminum isopropoxide (in an amount of Al 2 O 3 Calculated), 14.7g tetraethylammonium hydroxide (TEAOH), 8.5g ammonia (in NH) 3 Calculated by the mol ratio), 27g of deionized water, according to the mol ratio of Al 2 O 3 :TEAOH:NH 3 :H 2 Mixing O=1:1:1.25:15, and stirring for 2 hours at room temperature at a stirring rate of 70r/min to obtain a solution A; 6.5g of nickel chloride (calculated as NiO) and 27g of deionized water were added in a molar ratio of NiO to H 2 Mixing O=1:30, and stirring for 2 hours at room temperature at a stirring rate of 70r/min to obtain a solution B; the solution B and the nano-crystal initiator are synchronously added into the solution A in a dropwise manner at a dropwise rate of 0.6mL/min, the mass of the nano-crystal initiator is 1.7g, which accounts for 2.0 percent of the total mass of the solution A, B, and the solution B and the nano-crystal initiator are stirred for 2 hours at a stirring rate of 70r/min at 50 ℃ to form sol-gel; transferring the sol-gel into a hydrothermal reaction kettle, performing hydrothermal reaction at 120 ℃ for 48 hours, filtering the obtained hydrothermal reaction product, washing with deionized water, and washing until filtrate is obtainedThe pH value is 7.0, then the mixture is dried for 12 hours at 120 ℃, and finally baked for 2 hours at 500 ℃ to obtain the Al 2 O 3 -NiO composite catalyst with a yield of 98.1%. For the prepared Al 2 O 3 SEM characterization of the NiO composite catalyst to obtain the grain size; the crystallinity is obtained through XRD characterization; the specific surface area is obtained through BET characterization; by NH 3 -TPD characterization, resulting in acid quantity and acid strength. The characterization results are shown in table 1.
Example 4
9.2g of nickel nitrate (calculated as NiO) and 12.8g of aluminum isopropoxide (calculated as Al) 2 O 3 Calculated, 25.4g tetrapropylammonium hydroxide (TPAOH), 8.5g ammonia (amount NH) 3 Calculated) and 54g of deionized water, wherein the molar ratio of the deionized water is NiO to Al 2 O 3 :TPAOH:NH 3 :H 2 Mixing O=1:2.5:2.5:2.5:60, stirring at room temperature at a stirring rate of 80r/min for 2h, transferring into a hydrothermal reaction kettle, and carrying out hydrothermal reaction at 60 ℃ for 2 days to obtain a nanocrystal initiator; 2.8g of aluminum isopropoxide (in an amount of Al 2 O 3 Calculated, 25.4g tetrapropylammonium hydroxide (TPAOH), 8.5g ammonia (amount NH) 3 Calculated by the mol ratio), 54g of deionized water, according to the mol ratio of Al 2 O 3 :TPAOH:NH 3 :H 2 Mixing O=1:1:1:24, and stirring for 2 hours at room temperature at a stirring rate of 80r/min to obtain a solution A; 9.2g of nickel nitrate (calculated as NiO) and 36g of deionized water were added in a molar ratio of NiO to H 2 Mixing O=1:40, and stirring for 2 hours at room temperature at a stirring rate of 80r/min to obtain a solution B; the solution B and the nano-crystal initiator are synchronously added into the solution A in a dropwise manner at a dropwise rate of 0.5mL/min, the mass of the nano-crystal initiator is 6.8g, which accounts for 5.0 percent of the total mass of the solution A, B, and the solution B and the nano-crystal initiator are stirred for 2 hours at a stirring rate of 80r/min at a temperature of 60 ℃ to form sol-gel; transferring the sol-gel into a hydrothermal reaction kettle, performing hydrothermal reaction at 130 ℃ for 72 hours, filtering the obtained hydrothermal reaction product, washing with deionized water until the pH of the filtrate is 7.0, drying at 100 ℃ for 12 hours, and finally roasting at 550 ℃ for 2 hours to obtain Al 2 O 3 -NiO composite catalyst with 98.5% yield. For the prepared Al 2 O 3 NiO composite catalystSEM characterization, obtaining grain size; the crystallinity is obtained through XRD characterization; the specific surface area is obtained through BET characterization; by NH 3 -TPD characterization, resulting in acid quantity and acid strength. The characterization results are shown in table 1. Al obtained by the preparation 2 O 3 XRD patterns of NiO composite catalyst are shown in figure 1, NH 3 The TPD profile is shown in figure 2.
Example 5
6.5g of nickel chloride (calculated as NiO) and 9.3g of aluminum chloride (calculated as Al) 2 O 3 Calculated, 20.3g tetrapropylammonium hydroxide (TPAOH), 8.5g ammonia (amount NH) 3 Calculated) and 54g of deionized water, wherein the molar ratio of the deionized water is NiO to Al 2 O 3 :TPAOH:NH 3 :H 2 Mixing O=1:2.8:2:2.5:60, stirring at the stirring rate of 70r/min at room temperature for 3 hours, transferring into a hydrothermal reaction kettle, and carrying out hydrothermal reaction at 60 ℃ for 3 days to obtain a nanocrystal initiator; 9.3g of aluminum chloride (amount of Al 2 O 3 Calculated, 20.3g tetrapropylammonium hydroxide (TPAOH), 8.5g ammonia (amount NH) 3 Calculated by the mol ratio), 54g of deionized water, according to the mol ratio of Al 2 O 3 :TEAOH:NH 3 :H 2 Mixing O=1:0.7:0.9:21.4, and stirring at room temperature for 3 hours at a stirring rate of 70r/min to obtain a solution A; 6.5g of nickel chloride (calculated as NiO) and 36g of deionized water were added in a molar ratio of NiO to H 2 Mixing O=1:40, and stirring for 3 hours at room temperature at a stirring rate of 70r/min to obtain a solution B; the solution B and the nano-crystal initiator are synchronously added into the solution A in a dropwise manner at a dropwise rate of 0.6mL/min, the mass of the nano-crystal initiator is 10.8g, which accounts for 8.0 percent of the total mass of the solution A, B, and the solution B and the nano-crystal initiator are stirred for 3 hours at a stirring rate of 70r/min at a temperature of 60 ℃ to form sol-gel; transferring the sol-gel into a hydrothermal reaction kettle, performing hydrothermal reaction at 140 ℃ for 48 hours, filtering the obtained hydrothermal reaction product, washing with deionized water until the pH value of the filtrate is 7.0, drying at 120 ℃ for 12 hours, and finally roasting at 550 ℃ for 2 hours to obtain Al 2 O 3 -NiO composite catalyst with 97.8% yield. For the prepared Al 2 O 3 SEM characterization of the NiO composite catalyst to obtain the grain size; the crystallinity is obtained through XRD characterization; by BET tableObtaining the specific surface area; by NH 3 -TPD characterization, resulting in acid quantity and acid strength. The characterization results are shown in table 1.
Comparative example
Preparation of Al by non-nanocrystalline initiator method 2 O 3 NiO composite catalyst, in contrast to example 4: 2.8g of aluminum isopropoxide (in an amount of Al 2 O 3 Calculated, 25.4g tetrapropylammonium hydroxide (TPAOH), 8.5g ammonia (amount NH) 3 Calculated by the mol ratio), 54g of deionized water, according to the mol ratio of Al 2 O 3 :TPAOH:NH 3 :H 2 Mixing O=1:1:1:24, and stirring for 2 hours at room temperature at a stirring rate of 80r/min to obtain a solution A; 9.2g of nickel nitrate (calculated as NiO) and 36g of deionized water were added in a molar ratio of NiO to H 2 Mixing O=1:40, and stirring for 2 hours at room temperature at a stirring rate of 80r/min to obtain a solution B; the solution B and the nano-crystal initiator are synchronously added into the solution A in a dropwise manner at a dropwise rate of 0.5mL/min, the mass of the nano-crystal initiator is 6.8g, which accounts for 5.0 percent of the total mass of the solution A, B, and the solution B and the nano-crystal initiator are stirred for 2 hours at a stirring rate of 80r/min at a temperature of 60 ℃ to form sol-gel; transferring the sol-gel into a hydrothermal reaction kettle, performing hydrothermal reaction at 130 ℃ for 72 hours, filtering the obtained hydrothermal reaction product, washing with deionized water until the pH of the filtrate is 7.0, drying at 100 ℃ for 12 hours, and finally roasting at 550 ℃ for 2 hours to obtain Al 2 O 3 -NiO composite catalyst with a yield of 76.3%. Al obtained by the preparation 2 O 3 XRD patterns of NiO composite catalyst are shown in figure 1, NH 3 The TPD profile is shown in figure 2. For the prepared Al 2 O 3 SEM characterization of the NiO composite catalyst to obtain the grain size; the crystallinity is obtained through XRD characterization; the specific surface area is obtained through BET characterization; by NH 3 -TPD characterization, resulting in acid quantity and acid strength. The characterization results are shown in table 1.
TABLE 1
Pseudocumene-iso-benzeneThe reaction for the structured preparation of mesitylene is carried out in a fixed bed reactor. Al (Al) 2 O 3 The dosage of the NiO composite catalyst is 5.0g, the reaction temperature is 280 ℃, and the mass space velocity is 5.0h -1 The Al produced in each of examples and comparative examples was reacted under normal pressure for 2 hours 2 O 3 The reactivity of the NiO composite catalyst is shown in table 2. As can be seen from the experimental data in Table 2, the catalyst prepared in the examples of this patent showed higher conversion of pseudocumene and yield of mesitylene, and the amount of carbon deposit generated after the reaction was significantly lower than that in the comparative examples, showing excellent catalytic life.
TABLE 2
FIG. 1 is Al prepared in example 4 and comparative example 2 O 3 XRD pattern of NiO composite catalyst. As can be seen from the figure, al prepared in example 4 2 O 3 On the NiO composite catalyst, the intensity of each characteristic peak is significantly higher than that of the catalyst prepared in the comparative example, showing higher crystallinity.
FIG. 2 is Al prepared in example 4 and comparative example 2 O 3 NH of NiO composite catalyst 3 -TPD map. From the figure, the desorption peak between 200 and 400 ℃ is classified as a medium strong acid position, the desorption peak higher than 400 ℃ is classified as a strong acid position, the medium strong acid is beneficial to improving the yield of mesitylene, and the strong acid is easy to cause the generation of carbon deposit. Al prepared in example 4 2 O 3 On the NiO composite catalyst, the peak intensity of the medium strong acid is significantly higher than that of the strong acid, whereas on the catalyst prepared in the comparative example, the peak intensity of the strong acid is significantly higher than that of the medium strong acid; and the peak intensity of the strong acid on the catalyst prepared in example 4 was significantly higher than that of the catalyst prepared in comparative example, while the peak intensity of the strong acid on the catalyst prepared in example 4 was significantly lower than that of the catalyst prepared in comparative example.
In conclusion, the invention adopts the nanocrystal initiator method to prepare the nano Al 2 O 3 NiO composite catalystThe catalyst has the advantages of small grain size, high crystallinity, large specific surface area, large total acid amount, large medium and strong acid amount and the like, thereby showing excellent catalytic performances such as high pseudocumene conversion rate, high mesitylene yield and the like.
The invention provides a catalyst for preparing mesitylene by using pseudocumene isomerization and a method for preparing the catalyst, and the thought and the method for preparing the catalyst, wherein the method and the way for realizing the technical scheme are numerous, the above is only a preferred embodiment of the invention, and it should be pointed out that a plurality of improvements and modifications can be made by a person of ordinary skill in the art without departing from the principle of the invention, and the improvements and the modifications are also regarded as the protection scope of the invention. The components not explicitly described in this embodiment can be implemented by using the prior art.
Claims (6)
1. A method for preparing a catalyst for preparing mesitylene by using pseudocumene isomerization, which is characterized by comprising the following steps:
(1) Preparation of nanocrystal initiators: mixing an aluminum source, a nickel source, a template agent, ammonia water and deionized water, uniformly stirring at room temperature, and then performing hydrothermal reaction to obtain a nanocrystal initiator;
(2) Mixing an aluminum source, a template agent, ammonia water and deionized water, and uniformly stirring at room temperature to obtain a solution A;
(3) Mixing a nickel source with deionized water, and uniformly stirring at room temperature to obtain a solution B;
(4) Synchronously dripping the solution B and the nanocrystal initiator obtained in the step (1) into the solution A, and stirring to form sol-gel;
(5) Carrying out hydrothermal reaction on the sol-gel obtained in the step (4) at the temperature of 100-150 ℃ for 24-72 h;
(6) Filtering, washing and drying the hydrothermal reaction product obtained in the step (5), and finally roasting at 500-550 ℃ for 1-3 hours to obtain the catalyst;
in the step (1), the aluminum source is aluminum nitrate, aluminum isopropoxide or aluminum chloride, and the dosage is Al 2 O 3 Calculating; the nickel source is nickel nitrate or chloridizedNickel, the dosage is calculated by NiO; the dosage of the ammonia water is NH 3 Calculating; the template agent is tetraethylammonium hydroxide, tetrapropylammonium hydroxide or tetrabutylammonium hydroxide;
the raw materials are NiO to Al according to the mole ratio 2 O 3 Template agent NH 3 :H 2 O=1, (1.5-3): (2-3): (20-80), the stirring speed is 60-80 r/min, and the stirring time is controlled to be 1-3 h;
in the step (1), the temperature of the hydrothermal reaction is controlled to be 40-60 ℃, and the hydrothermal reaction time is 1-3 days;
in the step (2), the aluminum source is aluminum nitrate, aluminum isopropoxide or aluminum chloride, and the dosage is Al 2 O 3 Calculating; the dosage of the ammonia water is NH 3 Calculating; the template agent is tetraethylammonium hydroxide, tetrapropylammonium hydroxide or tetrabutylammonium hydroxide;
the raw materials are Al according to the mole ratio 2 O 3 Template agent NH 3 :H 2 O=1, (0.5-2), (0.6-2), (6-53) mixing, stirring at room temperature at a stirring rate of 60-80 r/min for 1-3 h;
in the step (4), the dosage of the nanocrystal initiator is 1.0-10.0% of the total mass of the solution A and the solution B; the mass ratio of the solution A to the solution B is 1.8-2.3.
2. The method for preparing a catalyst for the isomerization of pseudocumene to mesitylene according to claim 1, wherein in the step (3), the nickel source is nickel nitrate or nickel chloride, and the amount is calculated as NiO; the nickel source and deionized water are NiO to H in a mole ratio 2 O=1, (20-50) and stirring at room temperature at a stirring rate of 60-80 r/min for 1-3 h.
3. The method for preparing a catalyst for the isomerization of pseudocumene to mesitylene according to claim 1, wherein in the step (4), the solution B and the nanocrystal initiator are simultaneously added to the solution a at a dropping rate of 0.1 to 0.6mL/min, and then stirred at a stirring rate of 80 to 120r/min at a temperature of 40 to 60 ℃ for 3 to 5h to form a sol-gel.
4. The method for preparing a catalyst for the isomerization of pseudocumene to mesitylene according to claim 1, wherein in step (5), the washing is carried out with deionized water until the pH of the filtrate is 7.0; drying is carried out for 12-24 hours at 100-120 ℃.
5. The catalyst for preparing mesitylene by the isomerization of the pseudocumene, which is prepared by the preparation method of any one of claims 1 to 4.
6. Use of the catalyst of claim 5 for the preparation of mesitylene by the isomerisation of pseudocumene.
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