CN117019147A - Synthesis method of high-dispersity supported catalyst and method for preparing furfuryl alcohol by catalyzing furfural by using high-dispersity supported catalyst - Google Patents
Synthesis method of high-dispersity supported catalyst and method for preparing furfuryl alcohol by catalyzing furfural by using high-dispersity supported catalyst Download PDFInfo
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- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 title claims abstract description 110
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 title claims abstract description 94
- 239000003054 catalyst Substances 0.000 title claims abstract description 79
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000001308 synthesis method Methods 0.000 title description 3
- 229910052751 metal Inorganic materials 0.000 claims abstract description 13
- 239000002184 metal Substances 0.000 claims abstract description 13
- 229910052802 copper Inorganic materials 0.000 claims abstract description 9
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims description 52
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 238000001035 drying Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 239000008367 deionised water Substances 0.000 claims description 14
- 229910021641 deionized water Inorganic materials 0.000 claims description 14
- 239000011259 mixed solution Substances 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- 229910001220 stainless steel Inorganic materials 0.000 claims description 14
- 239000010935 stainless steel Substances 0.000 claims description 14
- 238000009210 therapy by ultrasound Methods 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 10
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 3
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000011068 loading method Methods 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000000630 rising effect Effects 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 239000010949 copper Substances 0.000 abstract description 64
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 6
- 230000002194 synthesizing effect Effects 0.000 abstract description 4
- 230000003197 catalytic effect Effects 0.000 abstract description 3
- 229910044991 metal oxide Inorganic materials 0.000 abstract description 2
- 150000004706 metal oxides Chemical group 0.000 abstract description 2
- 239000002086 nanomaterial Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 31
- 230000009467 reduction Effects 0.000 description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- 238000005984 hydrogenation reaction Methods 0.000 description 22
- 239000012071 phase Substances 0.000 description 20
- 239000001257 hydrogen Substances 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 238000004064 recycling Methods 0.000 description 12
- 239000012265 solid product Substances 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 229910000510 noble metal Inorganic materials 0.000 description 7
- 239000002028 Biomass Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000003912 environmental pollution Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- 241000609240 Ambelania acida Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- 238000003917 TEM image Methods 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 238000005261 decarburization Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000007849 furan resin Substances 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
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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
- 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
- B01J23/72—Copper
-
- 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
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
-
- 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
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/83—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with rare earths or actinides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
- C07D307/44—Furfuryl alcohol
-
- 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
- Y02P20/584—Recycling of catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
Abstract
The invention relates to the technical field of furfuryl alcohol catalysis by catalyzing furfural, and discloses a method for synthesizing supported catalyst and preparing furfuryl alcohol by catalyzing furfural. The supported catalyst M/N prepared by the invention x O y The carrier is metal oxide, the active metal is copper, and the nano material can catalyze furfural to prepare furfuryl alcohol. The supported catalyst M/N synthesized by the method provided by the invention x O y The catalyst is regular in morphology and good in hydrothermal stability, and the furfuryl alcohol is prepared by catalyzing furfural by the catalyst, so that the catalyst has high catalytic activity and reusability.
Description
Technical Field
The invention belongs to the technical field of biomass chemical preparation, and in particular relates to M/N x O y A method for preparing furfuryl alcohol by synthesizing a supported catalyst and catalyzing furfural.
Background
At present, the increase in energy demand and the excessive use of fossil energy bring about serious fossil energy crisis and environmental pollution, oil fields are being depleted, and the discharge of carbon dioxide generated by the combustion of fossil energy is affecting the climate of the earth, which is also a serious impediment faced by developing countries. Accordingly, much research is being devoted to the search and development of new renewable energy sources. Biomass energy is used as novel renewable energy, the inventionHaving carbon neutral, CO produced 2 And the biomass is also re-consumed, so that the environmental pollution is extremely low, and the biomass is considered as a substitute for fossil energy, and is the best choice of a new generation of main energy. Furfural is an important biomass platform derivative, can be prepared from corncob, waste straw, wheat bran, wood dust, bagasse and other agricultural byproducts, has no environmental pollution and other problems, and has considerable benefits for improving the environment.
Furfural derivatives are diverse and mainly comprise furfuryl alcohol, tetrahydrofurfuryl alcohol, tetrahydrofuran, furan, 2-methylfuran, 2-methyltetrahydrofuran, cyclopentanol and the like. In the hydrogenation of furfural, furfuryl alcohol is one of the most valuable furfural derivatives, and H can be used under the action of a transition metal catalyst 2 Gas phase or liquid phase hydrogenation of furfural. Furfuryl alcohol is the main raw material of light industry and the raw material of chemical products in the fields of agriculture, medical treatment, printing and dying, leather industry and the like, and is especially used for synthesizing furan resin, phenolic resin and furfuryl alcohol-urea formaldehyde values, and is used as a diluent of epoxy resin, a solvent of insoluble pigment such as phenolic resin and the like; can also be used for fine chemical products such as medicines, pesticides, coatings and the like. The production process for preparing furfuryl alcohol by hydrogenating furfural can be divided into liquid phase hydrogenation and gas phase hydrogenation. The liquid phase hydrogenation process is early developed, the reaction is generally carried out under higher pressure (3-8 MPa) and temperature (190-210 ℃), the requirement on the reactor is higher, the separation degree and the selectivity of the catalyst determine the difficulty of product refining, and therefore, the furfuryl alcohol is not generally prepared by adopting the method at present. The gas phase hydrogenation reaction is carried out at normal temperature or low pressure, the catalyst is easy to recycle, chromium pollution is eliminated, and main furfural manufacturers at home and abroad use a gas phase method to produce furfuryl alcohol.
Typically, the hydrogenation of furfural to furfuryl alcohol occurs at the surface of a metal catalyst. Various single-metal and double-metal catalysts are used for the hydrogenation reaction of furfural, and commonly used catalysts are mainly classified into noble metal catalysts and non-noble metal catalysts. Pd, ru, pt, au and the like are often adopted as noble metal catalysts, other side reactions (decarburization, hydrogenolysis and ring hydrogenation) of the noble metal catalysts are almost unavoidable due to the high activity of the noble metal catalysts, and the noble metal catalysts are high in price and are not beneficial to industrial production. Thus, people turn their eyes to the non-noble metals Cu, co, ni, fe, etc. Copper-based catalysts are the earliest applications in industrial furfural hydrogenation, have higher selectivity for c=o bond hydrogenation, can avoid furan ring hydrogenation, and greatly improve the yield of furfuryl alcohol. But the hydrogen decomposition capacity is poor, and improving the hydrogenation activity of the copper-based catalyst becomes a key for improving the selective hydrogenation of furfural to prepare furfuryl alcohol.
The supported copper-based catalyst refers to a catalyst in which active components of the catalyst are uniformly dispersed on a selected carrier, and a plurality of carriers contain acidic or alkaline sites and have certain catalytic performance on the hydrogenation reaction of furfural. Ren et al studied the characteristics of Cu/CuAl-MMO-400 catalyst in the hydrogenation of furfural to indicate that: cu (Cu) + Species are both dehydrogenation and hydrogenation active sites; and Cu is 0 The sites facilitate the transfer of H atoms between the adsorbed substrates. Liu et al have produced the catalyst Cu/MgO by a separate nucleation aging process with high efficiency due to the surface synergy between the catalytically active metallic copper species and the Lewis base sites, which is critical to the hydrogenation reaction associated with hydrogen dissociation and carbonyl activation. Therefore, in the reaction of preparing furfuryl alcohol by catalyzing furfural, a catalyst with both an L acid site and a hydrogenation active site needs to be designed, but the choice of a carrier is not known, so that the supported catalyst is more beneficial to catalyzing the furfural to synthesize the furfuryl alcohol. In this patent we use Cu + Is L acid site, cu 0 Cu is regulated by changing different reduction temperatures for hydrogenation active sites + /Cu 0 The ratio of the two active sites is effectively combined, and the synergistic effect is maximized, so that the reaction proceeds smoothly. Therefore, research and development of a novel supported catalyst M/N x O y The preparation method can efficiently catalyze furfurol to prepare furfuryl alcohol selectively, and the furfuryl alcohol can be a problem to be solved.
Disclosure of Invention
In view of this, the present invention provides supported catalysts M/N x O y A synthesis method of (2),And a method for preparing furfuryl alcohol by catalyzing furfural. The catalyst synthesized by the preparation method has the advantages of simple steps, easy operation, low energy consumption, uniform metal dispersion of the obtained supported catalyst, strong hydrothermal stability and repeated recycling.
In order to achieve the above object, the present invention adopts the following technical scheme:
S 1 mixing the metal salt precursor with water, stirring until the solid is dissolved, adding an oxide carrier, and stirring after ultrasonic treatment for a period of time to obtain a corresponding mixed solution;
S 2 stopping stirring, standing overnight, and then drying in an oven at a certain temperature;
S 3 roasting and H-treating the dried product 2 Reducing under the action to obtain M/N x O y ；
S 4 、M/N x O y The furfuryl alcohol preparing reaction with furfuraldehyde is performed in stainless steel high pressure reactor with N 2 Air in the kettle is replaced for a plurality of times, and then H is introduced 2 After multiple replacement, H in the high-pressure reaction kettle 2 The pressure is kept at a certain pressure, and the catalytic reaction is carried out by stable heating and stirring;
S 5 after the reaction is finished, centrifugally recovering the catalyst M/N x O y The catalyst phase is directly recycled without post-treatment.
The S is 1 The method is characterized in that the water is deionized water, and the metal salt is selected from Cu (NO) 3 ) 2 ·3H 2 O、Cu(CH 3 COO) 2 ·H 2 O、CuSO 4 ·5H 2 One of O and oxide carrier is MgO, znO, ceO 2 、TiO 2 、Al 2 O 3 、SiO 2 The metal loading is 5wt%, the ultrasonic time is 5-30 min, and the stirring time is 10-12 h.
The S is 2 The method is characterized in that the standing is carried out for 10 to 12 hours, the drying temperature is 60 to 80 ℃ and the drying time isFor 6-8 h.
The S is 3 The method is characterized in that the temperature rising rate of the muffle furnace is controlled to be 1-3 ℃/min, the muffle furnace is kept for 2-5 h after the muffle furnace is heated to 400-600 ℃, the tube furnace is controlled to be 1-3 ℃/min, and the muffle furnace is kept for 2-5 h after the muffle furnace is heated to 300-600 ℃.
The S is 4 The method is characterized in that nitrogen is used for replacing air in the kettle for 5-8 times, the nitrogen is used for replacing air in the kettle for 3-5 times, and H 2 The pressure is kept between 2 and 5MPa, M/N x O y And the quality of the furfural is 1 (1-5), the reaction temperature is 100-140 ℃ and the reaction time is 1-3 h.
The S is 5 The method is characterized in that after the reaction is finished, the catalyst M/N is centrifugally recovered x O y And furfuryl alcohol, the catalyst phase is directly recycled without post-treatment.
The supported catalyst M/N prepared by the invention x O y The active metal adopts copper, and the carrier adopts a nano structure of metal oxide. Compared with the prior art, the reduction temperature is regulated to regulate Cu + And Cu 0 The proportion reaches the highly dispersed supported catalyst with the optimal proportion of the active metal. Cu (Cu) 0 Cu as hydrogenation active site + As L acid active sites, the two active sites are effectively combined to maximize the synergistic effect, namely Cu + Selectively adsorb terminal carbonyl group, cu 0 Decomposition of H 2 Is hydrogen proton and then is transferred to Cu + The site, make C=O double bond selective hydrogenation produce furfuryl alcohol, very big improvement the reactivity. After the catalytic reaction is finished, the catalyst and the product can be simply and efficiently separated by utilizing a centrifugal mode, the catalyst phase does not need post-treatment and can be directly reused, the catalytic performance is not obviously reduced after the catalyst phase is reused for 5 times, and the recycling effect is good.
Drawings
FIG. 1 shows a multi-step synthesis of supported catalyst M/N according to the present invention x O y -schematic of the synthesis mechanism of X. .
FIG. 2 shows the supported catalyst M/N according to the present invention x O y SEM of-XAnd TEM images: (a1) Unreduced Cu/MgO-350, (a 2) Cu/MgO-350, (b 1) Cu/MgO-350, (b 2) lattice spacing of Cu, (c 1) - (c 2) lattice spacing of MgO.
FIG. 3 is M/N x O y XRD pattern of X catalyst.
Detailed Description
The invention discloses a method for synthesizing a supported catalyst and a method for preparing furfuryl alcohol by catalyzing furfural. Those skilled in the art can, with the benefit of this disclosure, suitably modify the process parameters to achieve this. It is expressly noted that all such similar substitutions and modifications will be apparent to those skilled in the art, and are deemed to be included herein. While the methods and applications of this invention have been described in terms of preferred embodiments, it will be apparent to those skilled in the relevant art that the methods and applications described herein can be modified or adapted and combined to implement and utilize the technology of this invention without departing from the spirit and scope of this invention.
The present invention will be described in further detail with reference to specific embodiments thereof so that those skilled in the art can better understand the present invention.
Example 1
S 1 Will be 0.32g CuSO 4 ·3H 2 Mixing O and 10.00mL of deionized water in a small beaker with the volume of 10.00mL, stirring until the solid is dissolved, adding an oxide carrier, then adding 1.50g of MgO carrier, carrying out ultrasonic treatment for 30min, stirring at room temperature, and keeping for 12h to obtain a corresponding mixed solution;
S 2 stopping stirring, standing overnight for 12h, and then drying in an oven at 80 ℃ for 6h;
S 3 roasting the dried product in a muffle furnace, wherein the roasting temperature is raised to 500 ℃ at a speed of 1 ℃/min, the roasting time is 3 hours, the obtained solid product is placed in a tube furnace for reduction, the reduction temperature is raised to 350 ℃ at a speed of 2 ℃/min, and the roasting time is 3 hours, so that the product Cu/MgO-350 (S) is obtained;
S 4 placing 0.05mL of furfural, 0.05g of Cu/MgO-350 (S), 5mL of isopropanol and high-temperature magneton in a 50mL high-temperature high-pressure stainless steel reactor, adding nitrogen gas to replace air in the kettle5 times, replacing 3 times by using hydrogen, keeping the pressure in the high-pressure reactor at 2MPa, and heating and stirring at 110 ℃ for 80min;
S 5 after the reaction, the mixture was allowed to stand and cooled to room temperature. And (3) centrifugally recovering the catalyst Cu/MgO-350 (S), and directly recycling the catalyst phase without post-treatment.
The yield of furfural is 99.9%, and the calculation formula of the yield of furfural is as follows:
Y＝S*X
wherein Y is the yield of furfural; x is the conversion rate of furfural; s is the selectivity of furfuryl alcohol; n is n initial The molar amount of the furfural added; n is n final Molar amount of furfuryl alcohol remaining; m is m product Is the molar mass of the product furfuryl alcohol.
Example 2
S 1 0.32g of Cu (NO) 3 ) 2 ·5H 2 Mixing O and 10.00mL of deionized water in a small beaker with the volume of 10.00mL, stirring until the solid is dissolved, adding an oxide carrier, then adding 1.50g of MgO carrier, carrying out ultrasonic treatment for 30min, stirring at room temperature, and keeping for 12h to obtain a corresponding mixed solution;
S 2 stopping stirring, standing overnight for 12h, and then drying in an oven at 80 ℃ for 6h;
S 3 roasting the dried product in a muffle furnace, wherein the roasting temperature is raised to 500 ℃ at a speed of 1 ℃/min, the roasting time is 3 hours, the obtained solid product is placed in a tube furnace for reduction, the reduction temperature is raised to 350 ℃ at a speed of 2 ℃/min, and the roasting time is 3 hours, so that the product Cu/MgO-350 (N) is obtained;
S 4 placing 0.05mL of furfural, 0.05g of Cu/MgO-350 (N), 5mL of isopropanol and high-temperature magneton in a 50mL high-temperature high-pressure stainless steel reactor, adding and using nitrogen for replacementThe air in the kettle is replaced by hydrogen for 3 times for 5 times, so that the pressure in the high-pressure reactor is kept at 2MPa, and the mixture is heated and stirred for 80 minutes at 110 ℃;
S 5 after the reaction, the mixture was allowed to stand and cooled to room temperature. And (3) centrifugally recovering the catalyst Cu/MgO-350 (N), and directly recycling the catalyst phase without post-treatment. The yield of furfuryl alcohol was 11.5%.
Example 3
S 1 0.34g of Cu (CH) 3 COO) 2 ·H 2 Mixing O and 10.00mL of deionized water in a small beaker with the volume of 10.00mL, stirring until the solid is dissolved, adding an oxide carrier, then adding 1.50g of MgO carrier, carrying out ultrasonic treatment for 30min, stirring at room temperature, and keeping for 12h to obtain a corresponding mixed solution;
S 2 stopping stirring, standing overnight for 12h, and then drying in an oven at 80 ℃ for 6h;
S 3 roasting the dried product in a muffle furnace, wherein the roasting temperature is raised to 500 ℃ at a speed of 1 ℃/min, the roasting time is 3 hours, the obtained solid product is placed in a tube furnace for reduction, the reduction temperature is raised to 350 ℃ at a speed of 2 ℃/min, and the roasting time is 3 hours, so that the product Cu/MgO-350 (A) is obtained;
S 4 placing 0.05mL of furfural, 0.05g of Cu/MgO-350 (A), 5mL of isopropanol and high-temperature magnetons into a 50mL high-temperature high-pressure stainless steel reactor, adding nitrogen to replace air in the kettle for 5 times, replacing the air with hydrogen for 3 times, keeping the pressure in the high-pressure reactor at 2MPa, and heating and stirring at 110 ℃ for 80min;
S 5 after the reaction, the mixture was allowed to stand and cooled to room temperature. And (3) centrifugally recovering the catalyst Cu/MgO-350 (A), and directly recycling the catalyst phase without post-treatment. The yield of furfural was 16.8%.
Example 4
S 1 Will be 0.32g CuSO 4 ·3H 2 Mixing O and 10.00mL of deionized water in a small beaker with the volume of 10.00mL, stirring until the solid is dissolved, adding an oxide carrier, then adding 1.50g of MgO carrier, carrying out ultrasonic treatment for 30min, stirring at room temperature, and keeping for 12h to obtain a corresponding mixed solution;
S 2 stopping stirring, standing overnight for 12h, and then drying in an oven at 80 ℃ for 6h;
S 3 roasting the dried product in a muffle furnace, wherein the roasting temperature is raised to 500 ℃ at a speed of 1 ℃/min, the roasting time is 3 hours, the obtained solid product is placed in a tubular furnace for reduction, the reduction temperature is raised to 300 ℃ at a speed of 2 ℃/min, and the roasting time is 3 hours, so that the product Cu/MgO-300 is obtained;
S 4 placing 0.05mL of furfural, 0.05g of Cu/MgO-300, 5mL of isopropanol and high-temperature magnetons into a 50mL high-temperature high-pressure stainless steel reactor, adding nitrogen to replace air in the kettle for 5 times, replacing the air with hydrogen for 3 times, keeping the pressure in the high-pressure reactor at 2MPa, and heating and stirring at 110 ℃ for 80min;
S 5 after the reaction, the mixture was allowed to stand and cooled to room temperature. And (3) centrifugally recovering the catalyst Cu/MgO-300, and directly recycling the catalyst phase without post-treatment. The yield of furfural was 34.8%.
Example 5
S 1 Will be 0.32g CuSO 4 ·3H 2 Mixing O and 10.00mL of deionized water in a small beaker with the volume of 10.00mL, stirring until the solid is dissolved, adding an oxide carrier, then adding 1.50g of MgO carrier, carrying out ultrasonic treatment for 30min, stirring at room temperature, and keeping for 12h to obtain a corresponding mixed solution;
S 2 stopping stirring, standing overnight for 12h, and then drying in an oven at 80 ℃ for 6h;
S 3 roasting the dried product in a muffle furnace, wherein the roasting temperature is raised to 500 ℃ at a speed of 1 ℃/min, the roasting time is 3 hours, the obtained solid product is placed in a tubular furnace for reduction, the reduction temperature is raised to 400 ℃ at a speed of 2 ℃/min, and the roasting time is 3 hours, so that the product Cu/MgO-400 is obtained;
S 4 placing 0.05mL of furfural, 0.05g of Cu/MgO-400, 5mL of isopropanol and high-temperature magnetons into a 50mL high-temperature high-pressure stainless steel reactor, adding nitrogen to replace air in the kettle for 5 times, replacing the air with hydrogen for 3 times, keeping the pressure in the high-pressure reactor at 2MPa, and heating and stirring at 110 ℃ for 80min;
S 5 after the reaction, the mixture was allowed to stand and cooled to room temperature. And (3) centrifugally recycling the catalyst Cu/MgO-400, wherein the catalyst phase is directly recycled without post-treatment. The yield of furfural was 55.7%.
Example 6
S 1 Will be 0.32g CuSO 4 ·3H 2 Mixing O and 10.00mL of deionized water in a small beaker with the volume of 10.00mL, stirring until the solid is dissolved, adding an oxide carrier, then adding 1.50g of MgO carrier, carrying out ultrasonic treatment for 30min, stirring at room temperature, and keeping for 12h to obtain a corresponding mixed solution;
S 2 stopping stirring, standing overnight for 12h, and then drying in an oven at 80 ℃ for 6h;
S 3 roasting the dried product in a muffle furnace, wherein the roasting temperature is raised to 500 ℃ at a speed of 1 ℃/min, the roasting time is 3 hours, the obtained solid product is placed in a tube furnace for reduction, the reduction temperature is raised to 450 ℃ at a speed of 2 ℃/min, and the roasting time is 3 hours, so that the product Cu/MgO-450 is obtained;
S 4 placing 0.05mL of furfural, 0.05g of Cu/MgO-300, 5mL of isopropanol and high-temperature magnetons into a 50mL high-temperature high-pressure stainless steel reactor, adding nitrogen to replace air in the kettle for 5 times, replacing the air with hydrogen for 3 times, keeping the pressure in the high-pressure reactor at 2MPa, and heating and stirring at 110 ℃ for 80min;
S 5 after the reaction, the mixture was allowed to stand and cooled to room temperature. And (3) centrifugally recycling the catalyst Cu/MgO-450, wherein the catalyst phase is directly recycled without post-treatment. The yield of furfural was 40.8%.
Example 7
S 1 Will be 0.32g CuSO 4 ·3H 2 Mixing O and 10.00mL of deionized water in a small beaker with the volume of 10.00mL, stirring until the solid is dissolved, adding an oxide carrier, then adding 1.50g of MgO carrier, carrying out ultrasonic treatment for 30min, stirring at room temperature, and keeping for 12h to obtain a corresponding mixed solution;
S 2 stopping stirring, standing overnight for 12h, and then drying in an oven at 80 ℃ for 6h;
S 3 will be spentRoasting the dried product in a muffle furnace, wherein the roasting temperature is raised to 500 ℃ at a speed of 1 ℃/min, the roasting time is 3 hours, the obtained solid product is placed in a tubular furnace for reduction, the reduction temperature is raised to 500 ℃ at a speed of 2 ℃/min, and the roasting time is 3 hours, so that the product Cu/MgO-500 is obtained;
S 4 placing 0.05mL of furfural, 0.05g of Cu/MgO-500, 5mL of isopropanol and high-temperature magnetons into a 50mL high-temperature high-pressure stainless steel reactor, adding nitrogen to replace air in the kettle for 5 times, replacing the air with hydrogen for 3 times, keeping the pressure in the high-pressure reactor at 2MPa, and heating and stirring at 110 ℃ for 80min;
S 5 after the reaction, the mixture was allowed to stand and cooled to room temperature. And (3) centrifugally recycling the catalyst Cu/MgO-500, wherein the catalyst phase is directly recycled without post-treatment. The yield of furfural was 29.5%.
Example 8
S 1 Will be 0.32g CuSO 4 ·3H 2 Mixing O and 10.00mL of deionized water in a small beaker with the volume of 10.00mL, stirring until the solid is dissolved, adding an oxide carrier, then adding 1.50g of ZnO carrier, carrying out ultrasonic treatment for 30min, stirring at room temperature, and keeping for 12h to obtain a corresponding mixed solution;
S 2 stopping stirring, standing overnight for 12h, and then drying in an oven at 80 ℃ for 6h;
S 3 roasting the dried product in a muffle furnace, wherein the roasting temperature is raised to 500 ℃ at a speed of 1 ℃/min, the roasting time is 3 hours, the obtained solid product is placed in a tubular furnace for reduction, the reduction temperature is raised to 350 ℃ at a speed of 2 ℃/min, and the roasting time is 3 hours, so that the product Cu/ZnO is obtained;
S 4 0.05mL of furfural, 0.05g of Cu/ZnO, 5mL of isopropanol and high-temperature magnetons are placed in a 50mL high-temperature high-pressure stainless steel reactor, the air in the reactor is replaced by nitrogen for 5 times and hydrogen for 3 times, the pressure in the high-pressure reactor is kept at 2MPa, and the reactor is heated and stirred at 110 ℃ for 80 minutes.
S 5 After the reaction, the mixture was allowed to stand and cooled to room temperature. And (3) centrifugally recovering the catalyst Cu/ZnO, and directly recycling the catalyst phase without post-treatment. FurfuralThe yield thereof was found to be 10.3%.
Example 9
S 1 Will be 0.32g CuSO 4 ·3H 2 O was mixed with 10.00mL deionized water in a small 10.00mL beaker, stirred until the solids dissolved, then the oxide support was added, then 1.50g CeO was added 2 Carrying out ultrasonic treatment on the carrier for 30min, stirring at room temperature, and keeping for 12h to obtain a corresponding mixed solution;
S 2 stopping stirring, standing overnight for 12h, and then drying in an oven at 80 ℃ for 6h;
S 3 roasting the dried product in a muffle furnace, wherein the roasting temperature is raised to 500 ℃ at a speed of 1 ℃/min, the roasting time is 3 hours, the obtained solid product is placed in a tubular furnace for reduction, the reduction temperature is raised to 350 ℃ at a speed of 2 ℃/min, and the roasting time is 3 hours, so that the product CeO is obtained 2 ；
S 4 0.05mL of furfural and 0.05g of Cu/CeO 2 Placing 5mL of isopropanol and high-temperature magneton in a 50mL high-temperature high-pressure stainless steel reactor, adding nitrogen to replace air in the kettle for 5 times, replacing the air with hydrogen for 3 times, keeping the pressure in the high-pressure reactor at 2MPa, and heating and stirring at 110 ℃ for 80min;
S 5 after the reaction, the mixture was allowed to stand and cooled to room temperature. Centrifugally recovering Cu/CeO as catalyst 2 The catalyst phase is directly recycled without post-treatment. The yield of furfural was 42.6%.
Example 10
S 1 Will be 0.32g CuSO 4 ·3H 2 O was mixed with 10.00mL deionized water in a small 10.00mL beaker, stirred until the solids dissolved, then the oxide support was added, then 1.50g Al was added 2 O 3 Carrying out ultrasonic treatment on the carrier for 30min, stirring at room temperature, and keeping for 12h to obtain a corresponding mixed solution;
S 2 stopping stirring, standing overnight for 12h, and then drying in an oven at 80 ℃ for 6h;
S 3 roasting the dried product in a muffle furnace, wherein the roasting temperature is raised to 500 ℃ at a speed of 1 ℃/min, the roasting time is 3 hours,the obtained solid product is placed in a tube furnace for reduction, the reduction temperature is increased to 350 ℃ at the speed of 2 ℃/min, the roasting time is 3 hours, and the product Cu/Al is obtained 2 O 3 ；
S 4 0.05mL furfural, 0.05g Cu/Al 2 O 3 Placing 5mL of isopropanol and high-temperature magneton in a 50mL high-temperature high-pressure stainless steel reactor, adding nitrogen to replace air in the kettle for 5 times, replacing the air with hydrogen for 3 times, keeping the pressure in the high-pressure reactor at 2MPa, and heating and stirring at 110 ℃ for 80min;
S 5 after the reaction, the mixture was allowed to stand and cooled to room temperature. Centrifugal recovery of catalyst Cu/Al 2 O 3 The catalyst phase is directly recycled without post-treatment. The yield of furfural was 68.7%.
Example 11
S 1 Will be 0.32g CuSO 4 ·3H 2 O was mixed with 10.00mL deionized water in a small 10.00mL beaker, stirred until the solids dissolved, then the oxide support was added, then 1.50g TiO was added 2 Carrying out ultrasonic treatment on the carrier for 30min, stirring at room temperature, and keeping for 12h to obtain a corresponding mixed solution;
S 2 stopping stirring, standing overnight for 12h, and then drying in an oven at 80 ℃ for 6h;
S 3 roasting the dried product in a muffle furnace, wherein the roasting temperature is raised to 500 ℃ at a speed of 1 ℃/min, the roasting time is 3 hours, the obtained solid product is placed in a tubular furnace for reduction, the reduction temperature is raised to 350 ℃ at a speed of 2 ℃/min, and the roasting time is 3 hours, so that the product Cu/TiO is obtained 2 ；
S 4 Placing 0.05mL of furfural, 0.05g of Cu/MgO, 5mL of isopropanol and high-temperature magnetons into a 50mL high-temperature high-pressure stainless steel reactor, adding nitrogen to replace air in the kettle for 5 times, replacing the air with hydrogen for 3 times, keeping the pressure in the high-pressure reactor at 2MPa, and heating and stirring at 110 ℃ for 80min;
S 5 after the reaction, the mixture was allowed to stand and cooled to room temperature. Centrifugally recovering Cu/TiO catalyst 2 The catalyst phase is directly recycled without post-treatment. The yield of furfural was 11.5%。
Example 12
S 1 Will be 0.32g CuSO 4 ·3H 2 O was mixed with 10.00mL deionized water in a small 10.00mL beaker, stirred until the solids dissolved, then the oxide support was added, then 1.50g SiO was added 2 Carrying out ultrasonic treatment on the carrier for 30min, stirring at room temperature, and keeping for 12h to obtain a corresponding mixed solution;
S 2 stopping stirring, standing overnight for 12h, and then drying in an oven at 80 ℃ for 6h;
S 3 roasting the dried product in a muffle furnace, wherein the roasting temperature is raised to 500 ℃ at a speed of 1 ℃/min, the roasting time is 3 hours, the obtained solid product is placed in a tubular furnace for reduction, the reduction temperature is raised to 350 ℃ at a speed of 2 ℃/min, and the roasting time is 3 hours, so that the product Cu/SiO is obtained 2 ；
S 4 Placing 0.05mL of furfural, 0.05g of Cu/MgO, 5mL of isopropanol and high-temperature magnetons into a 50mL high-temperature high-pressure stainless steel reactor, adding nitrogen to replace air in the kettle for 5 times, replacing the air with hydrogen for 3 times, keeping the pressure in the high-pressure reactor at 2MPa, and heating and stirring at 110 ℃ for 80min;
S 5 after the reaction, the mixture was allowed to stand and cooled to room temperature. Centrifugal recovery of catalyst Cu/SiO 2 The catalyst phase is directly recycled without post-treatment. The yield of furfural was 17.7%.
Example 13
The experimental conditions and steps were the same as in example 1, except that the catalyst was changed to the catalyst recovered in example 1, and 5 times of recycling experiments were performed, and the yield of furfural after 5 times of recycling was 94.7%.
The foregoing is merely a preferred embodiment of the present invention and it should be noted that modifications and adaptations to those skilled in the art may be made without departing from the principles of the present invention, which are intended to be comprehended within the scope of the present invention.
Claims (6)
1.M/N x O y Synthesis and catalysis of supported catalystsThe method for preparing the furfural by the furfural is characterized by comprising the following steps:
S 1 mixing the metal salt precursor with water, stirring until the solid is dissolved, adding an oxide carrier, and stirring after ultrasonic treatment for a period of time to obtain a corresponding mixed solution;
S 2 stopping stirring, standing overnight, and then drying in an oven at a certain temperature;
S 3 roasting and H-treating the dried product 2 Reducing under the action to obtain M/N x O y ；
S 4 、M/N x O y The furfuryl alcohol preparing reaction with furfuraldehyde is performed in stainless steel high pressure reactor with N 2 Air in the kettle is replaced for a plurality of times, and H is introduced 2 After multiple replacement, H in the high-pressure reaction kettle 2 The pressure is kept at a certain pressure, and the catalytic reaction is carried out by stable heating and stirring;
s5, after the reaction is finished, centrifugally recovering the catalyst M/N x O y The catalyst phase is directly recycled without post-treatment.
2. S as claimed in claim 1 1 The method is characterized in that the water is deionized water, and the metal salt is selected from Cu (NO) 3 )·3H 2 O、Cu(CH 3 COO) 2 ·H 2 O、CuSO 4 ·5H 2 One of O and oxide carrier is MgO, znO, ceO 2 、TiO 2 、Al 2 O 3 、SiO 2 The metal loading is 5wt%, the ultrasonic time is 5-30 min, and the stirring time is 10-12 h.
3. S as claimed in claim 1 2 The method is characterized in that the standing is carried out for 10 to 12 hours, the drying temperature is 60 to 80 ℃, and the drying time is 6 to 8 hours.
4. S as claimed in claim 1 3 The method is characterized in that the temperature rising rate of the muffle furnace is controlled to be 1-3 ℃/minThe temperature is maintained for 2 to 5 hours after the temperature is raised to 400 to 600 ℃, the temperature raising rate of the tube furnace is controlled to be 1 to 3 ℃/min, and the temperature is maintained for 2 to 5 hours after the temperature is raised to 300 to 600 ℃.
5. S as claimed in claim 1 4 The method is characterized in that nitrogen is used for replacing air in the kettle for 5-8 times, the nitrogen is used for replacing air in the kettle for 3-5 times, and H 2 The pressure is kept between 2 and 5MPa, M/N x O y And the quality of the furfural is 1 (1-5), the reaction temperature is 100-140 ℃ and the reaction time is 1-3 h.
6. S as claimed in claim 1 5 Method, after the reaction is finished, centrifugally recovering the catalyst M/N x O y And furfuryl alcohol, the catalyst phase is directly recycled without post-treatment.
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