CN105772082A - Preparing method and catalytic application of ruthenium nanocomposite - Google Patents
Preparing method and catalytic application of ruthenium nanocomposite Download PDFInfo
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- CN105772082A CN105772082A CN201610217534.9A CN201610217534A CN105772082A CN 105772082 A CN105772082 A CN 105772082A CN 201610217534 A CN201610217534 A CN 201610217534A CN 105772082 A CN105772082 A CN 105772082A
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- 230000003197 catalytic effect Effects 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 14
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 229910052707 ruthenium Inorganic materials 0.000 title claims abstract description 11
- 239000002114 nanocomposite Substances 0.000 title description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229910021389 graphene Inorganic materials 0.000 claims abstract description 29
- 239000002105 nanoparticle Substances 0.000 claims abstract description 22
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- -1 aromatic sulfamide compound Chemical class 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 4
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical group N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims description 31
- 238000006555 catalytic reaction Methods 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 239000002243 precursor Substances 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 7
- 230000001105 regulatory effect Effects 0.000 claims description 6
- 239000011943 nanocatalyst Substances 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 238000000643 oven drying Methods 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- ZDOBFUIMGBWEAB-XGFHMVPTSA-N cucurbit[7]uril Chemical compound N1([C@H]2[C@H]3N(C1=O)CN1[C@H]4[C@H]5N(C1=O)CN1[C@H]6[C@H]7N(C1=O)CN1[C@H]8[C@H]9N(C1=O)CN1[C@H]%10[C@H]%11N(C1=O)CN([C@@H]1N(C%12=O)CN%11C(=O)N%10CN9C(=O)N8CN7C(=O)N6CN5C(=O)N4CN3C(=O)N2C2)C3=O)CN4C(=O)N5[C@H]6[C@@H]4N2C(=O)N6CN%12[C@@H]1N3C5 ZDOBFUIMGBWEAB-XGFHMVPTSA-N 0.000 claims 1
- 239000006185 dispersion Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 11
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 230000009881 electrostatic interaction Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000000969 carrier Substances 0.000 abstract description 3
- 239000002245 particle Substances 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract 4
- 238000007036 catalytic synthesis reaction Methods 0.000 abstract 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 5
- 239000003223 protective agent Substances 0.000 description 5
- 229910019891 RuCl3 Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 208000035126 Facies Diseases 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 241000219112 Cucumis Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- MSBXTPRURXJCPF-DQWIULQBSA-N cucurbit[6]uril Chemical compound N1([C@@H]2[C@@H]3N(C1=O)CN1[C@@H]4[C@@H]5N(C1=O)CN1[C@@H]6[C@@H]7N(C1=O)CN1[C@@H]8[C@@H]9N(C1=O)CN([C@H]1N(C%10=O)CN9C(=O)N8CN7C(=O)N6CN5C(=O)N4CN3C(=O)N2C2)C3=O)CN4C(=O)N5[C@@H]6[C@H]4N2C(=O)N6CN%10[C@H]1N3C5 MSBXTPRURXJCPF-DQWIULQBSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002082 metal nanoparticle Substances 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000001637 plasma atomic emission spectroscopy Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/063—Polymers comprising a characteristic microstructure
-
- B01J35/393—
-
- B01J35/399—
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
- B01J2231/4283—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues using N nucleophiles, e.g. Buchwald-Hartwig amination
Abstract
The invention provides a method of preparing a ruthenium nano-particle catalyst with cucurbit urils and reduction-oxidation graphene serving as common carriers in a synthesis mode, and the catalyst is used for catalytic synthesis of an aromatic sulfamide compound. The chemical component of the nano-particle catalyst is ruthenium, cucurbit urils and reduction-oxidation graphene, cucurbit urils and reduction-oxidation graphene serve as the common carriers, reduction-oxidation graphene is effectively prevented from agglomerating by means of the electrostatic interaction and volume effect of cucurbit urils, and the prepared ultra-small Ru nano-particles are uniform in particle size and are dispersed evenly. The prepared nano-particle catalyst is high in catalytic activity and stability and capable of efficiently catalyzing a sulfamide and aromatic alcohol reaction to prepare the aromatic sulfamide compound. The catalyst can be repeatedly used while activity is not reduced obviously. The method has the advantages of being simple in synthesis, convenient to operate, wide in application range, mild in preparation condition, simple and low in cost, and special equipment is not needed.
Description
Technical field
The present invention relates to the use of melon ring and redox graphene be uniformly dispersed as the synthesis of common carrier, the method for the extra small ruthenium nano-particle of uniform particle diameter.Utilize electrostatic interaction and the bulk effect of melon ring, redox graphene is carried out special adsorption, obtain the redox graphene that will not occur to reunite.Melon ring and redox graphene, as common carrier and protective agent, effectively limit the reunion of ruthenium nano-particle and growth, obtain showing the ruthenium nanocatalyst of excellence in organic catalysis.The invention belongs to catalysis material field.
Background technology
Effectively construct new carbon-nitrogen bond and be always up the focus in organic catalysis field.Aromatic amide compound containing carbon-nitrogen bond is the basic construction unit of many medicines, luminous organic material.Being generally adopted amine and sulfonic acid chloride and synthesize corresponding aromatic amide compound as substrate, but Halogen aromatic toxicity is relatively big, by-product environmental pollution is serious.The by-product that the aromatic alcohol of sulfonic acid chloride obtains after the reaction can be replaced and only have water, and nontoxic, it is the synthetic route of Atom economy.But the electrophilicity of aromatic alcohol is but very weak, it is possible to the catalyst of effectively this reaction of catalysis becomes the key of this circuit combination aromatic amide compound.The coordination compound of metal Ru as homogeneous catalyst can effectively catalysis various organic reactions, but needed for some coordination compounds, part preparation process is numerous and diverse, expensive, coordination compound itself also be difficult to from product separate, it is difficult to recycling.Nano-particle has higher specific surface area, is also easy to carry out finishing, is capable of homogeneousization of catalytic process as catalyst.Meanwhile, nano-particle also is able to by multiple method, as filtered or magnetic-adsorption etc., separates so that the last handling process out-phase of synthesis from reaction system.Owing to nano-particle catalysis has the advantage of homogeneous catalysis and heterocatalysis simultaneously, so nano-catalytic becomes the focus forward position of commercial production and scientific research.
At present, surface protectant is less, the stability of the nano-particle with higher catalytic activity is bad, occurs as soon as the phenomenons such as reunion inactivation after twice catalytic reaction.And protected dose of the surface of the higher nanocatalyst of those stability covers serious, so catalysis activity is bad.These problems mostly come from protective agent and the carrier that nano-particle is used in building-up process.Redox graphene (rGO) and melon ring (cucurbituril, CB) are the two kinds of novel carriers and the protective agent that are respectively provided with plane layer structure and annular rigid structure.Redox graphene has good electric conductivity, it is possible to strengthen the catalytic performance of the catalytic reaction relating to electron transfer.But the layer of redox graphene is extremely easily reunited together, significantly weaken various performance.Melon ring then can carry out stabilized nanoscale material by electrostatic interaction and bulk effect.As emerging bearer type in recent years, the melon toroidal molecule of ring-type has insoluble in common solvents, and has the advantages such as higher chemical stability and heat stability.Melon ring and redox graphene is utilized to prepare the research of finely dispersed extra small metal nanoparticle catalyst it is not yet reported that mistake as common carrier and protective agent.By regulating multiple reaction condition, such as the Acidity of Aikalinity of system, the material ratio etc. between metal precursor salt and carrier, it is possible to prepare and be uniformly dispersed, grain is through homogeneous extra small Ru nanoparticle catalyst.This nano-particle is prepared aromatic amide compound for catalysis sulfonamide and aromatic alcohol reaction and is shown excellent catalysis activity and stability.
Summary of the invention
It is an object of the invention to provide one and prepared metal Ru nanoparticle catalyst by melon ring and redox graphene as common carrier, and the catalytic reaction being applied to sulfonamide and aromatic alcohol prepares aromatic amide compound.Nanoparticle catalyst prepared by the present invention has excellent catalysis activity and stability, it is possible to repeatedly use.
The preparation method that another object of the present invention is to provide above-mentioned catalyst.
The chemical composition of the nanoparticle catalyst of the present invention is metal Ru, melon ring and redox graphene.Wherein the content of catalytic active component Ru can be adjusted to 30% (mass percent) from 2%.Melon ring and redox graphene are as common carrier and protective agent, and the electrostatic interaction of melon ring and bulk effect effectively prevent the reunion of redox graphene, and the extra small Ru nano-particle grain prepared is through homogeneous and be uniformly dispersed.Melon ring and redox graphene are indispensable, only use the Ru nano-particle that a kind of carrier prepares disperse uneven and be prone to reunite, and catalysis activity is not high.The another one key factor preparing this nanocatalyst is exactly the Acidity of Aikalinity of reaction system, and lot of experiments determines that catalysis sulfonamide and aromatic alcohol reaction are prepared aromatic amide compound and had the most excellent catalytic performance by the Ru/ melon ring prepared in neutral conditions/redox graphene composite Nano catalysis material (Ru/CB/rGO).Nano catalytic material provided by the invention, has technique simple, easy to operate, and the feature such as have wide range of applications.
The present invention uses following technical scheme:
1. provide method to be synthetically derived melon ring and graphene oxide according to document.
2. under room temperature, a certain amount of metal precursor salt RuCl3Aqueous solution, regulation system pH value is in particular range；
3. melon ring and graphene oxide solid join step 2 in solution, stir the suspension being uniformly mixed for 4 hours；
4. by five times of equivalents in metal precursor RuCl3NaBH4Solid is dissolved in ethanol, obtains reducing agent；
5. the reducing agent of step 4 is added in the suspension of step 3, magnetic agitation 3 hours after sealing；
6. the product arrived of step 5 centrifugal after, wash twice, washing with alcohol once, oven drying.
Nano catalytic material provided by the present invention has the advantage that
(1) granule of active component is extra small, grain through homogeneous, be uniformly dispersed.
(2) adjustment of content of metal can be realized by regulating rate of charge.
(3) adjustment of ratio can realize the adjustment of different loads effect to pass through to be total between carrier.
(4) catalytic performance of this nano catalytic material is excellent, it is possible under mild conditions, completes catalytic reaction, and catalysis activity is not decreased obviously after repeatedly recycling in the short period.
Accompanying drawing explanation
Fig. 1: the transmission electron microscope photo of the Ru/CB/rGO that pH value prepares when being 7
The grain of Fig. 2: Ru/CB/rGO is through statistical distribution
Fig. 3: only with the transmission electron microscope photo (Ru/CB) of a kind of support C B Ru nano-particle prepared
Fig. 4: only with the transmission electron microscope photo (Ru/rGO) of a kind of carrier rGO Ru nano-particle prepared.
Fig. 5: the transmission electron microscope photo of Ru/CB/rGO after catalysis.
Fig. 6: catalytic cycle service condition.
Detailed description of the invention
Embodiment 1:
The preparation of Ru/CB/rGO, by 0.2mL (0.1mmol/mL) RuCl3Aqueous solution join in the deionized water of 300mL, regulating its pH value with the sodium hydrate aqueous solution of 0.1M is 7；50mg hexa-atomic melon ring (CB [6]) and 50mg graphene oxide (GO) solid join in the solution of above-mentioned metal precursor salt, after stirring 4 hours to homogeneous suspension；190mgNaBH4After being dissolved in 200mL ethanol, fast drop is in above-mentioned suspension；Being centrifuged after continuously stirred 3 hours in airtight environment, water washing twice, washing with alcohol are once.Dried ethanol disperses, and transmission electron microscope observing product is grain through for 1.25 ± 0.25nm, finely dispersed extra small Ru nano-particle (Ru/CB/rGO).Plasma emission spectroscopy (ICP) is analyzed result and is shown that the content of Ru is 2%.
Embodiment 2:
By 3mL (0.1mmol/mL) RuCl3Aqueous solution join in the deionized water of 300mL, regulating its pH value with the sodium hydrate aqueous solution of 0.1M is 7；50mg hexa-atomic melon ring (CB [6]) and 50mg graphene oxide (GO) solid join in the solution of above-mentioned metal precursor salt, after stirring 4 hours to homogeneous suspension；2.85gNaBH4After being dissolved in 400mL ethanol, fast drop is in above-mentioned suspension；Being centrifuged after continuously stirred 3 hours in airtight environment, water washing twice, washing with alcohol are once.Icp analysis result shows that the content of Ru is 30%.
Embodiment 3:
Institute is identical with embodiment 1 in steps, except hexa-atomic melon ring changes eight yuan of melon rings into, obtains Ru/CB [8]/rGO, and icp analysis result shows that the content of Ru is 12%.
Embodiment 4:
Institute is identical with embodiment 1 in steps, except pH value need not regulate, obtains Ru/CB/rGO-2.
Embodiment 5:
Ru/CB/rGO catalysis sulfonamide and aromatic alcohol prepare aromatic amide compound, 138mgK2CO3, p-methylphenyl sulphonylamine (1mmol), 1mL benzyl alcohol and 10mgRu/CB/rGO add in the pressure reaction bulb of 35mL, react 6 hours when 130 degrees Celsius after airtight.Reaction adds 5mL water after terminating, and is then extracted with ethyl acetate organic facies.The part that aqueous phase contains catalyst fines, through separating and respectively washing once with water, ethanol, reclaims catalyst after drying.Organic facies obtains product through column chromatography for separation, and isolated yield is 98%.In employing embodiment 4, preparation-obtained material is as catalyst, and catalysis productivity is 60% under the same conditions.
Above said content is only the basic explanation under present inventive concept, and according to any equivalent transformation that technical scheme is done, all should belong to protection scope of the present invention.
Claims (7)
1. being carried on a ruthenium nanoparticle catalyst for melon ring and redox graphene, chemistry skeleton symbol is: Ru/CB/rGO, wherein the content of active component Ru can be adjusted to 30% from 2%；Wherein melon ring and redox graphene are as common carrier.
2. a preparation method for the catalyst described in claim 1, comprises the steps:
(1) melon ring and graphene oxide are first synthesized；
(2) pH value of metal Ru precursor salt aqueous solution is regulated in particular range with sodium hydrate aqueous solution；
(3) melon ring step (1) synthesized and graphene oxide and metal Ru precursor salt add in the solution of step (2) according to certain mass ratio, stir 4 hours, and dispersion obtains mixture；
(4) sodium borohydride that mol ratio is five times in ruthenium precursor salt is dissolved in ethanol, obtains reducing agent；
(5) reducing agent of step (4) is rapidly injected in the mixture of step (3), magnetic agitation 3 hours；
(6) step (5) product is by centrifugal, wash twice, washing with alcohol once after, oven drying obtains final nano catalytic material；
(7) step (2), (3) must add each amount of substance according to certain ratio；
(8) the melon ring of different proportion, graphene oxide and metal precursor are added, it is possible to obtain the nanocatalyst that a series of active component content is different；The surface nature of the active component regulating the pH nanocatalyst prepared under different acid, alkali and neutrallty condition is different.
3. method according to claim 2, it is characterised in that: in described step (2), the aqueous solution of ruthenium precursor salt needs to regulate pH at particular range with sodium hydrate aqueous solution.
4. method according to claim 2, it is characterized in that: the kind of melon ring affiliated in described step (3) is different, can obtaining the ruthenium nano catalytic material of different loads and catalytic effect, wherein the kind of melon ring is mainly five yuan of melon rings, hexa-atomic melon ring, cucurbit(7)uril and eight yuan of melon rings.
5. method according to claim 2, it is characterised in that: melon ring affiliated in described step (3) and the mass ratio of graphene oxide can regulate within the scope of full scale, obtain load and the different nano catalytic material of catalytic effect.
6. method according to claim 2, it is characterised in that: the melon ring added in step (3) and the gross mass of graphene oxide are adjusted with the mass ratio of metal precursor salt, it is possible to obtain the nano catalytic material of active component different loads amount.
7. the nano catalytic material described in claim 1 prepares aromatic amide compound for catalysis sulfonamide and aromatic alcohol reaction.
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| CN110368988A (en) * | 2019-08-13 | 2019-10-25 | 辽宁大学 | A kind of vitamin B12With the difunctional graphite alkene catalysis material of ruthenium complex and its preparation method and application |
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| CN114016071A (en) * | 2021-07-29 | 2022-02-08 | 中国科学院福建物质结构研究所 | Multi-element copper-based composite material and preparation method and application thereof |
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| CN106492757A (en) * | 2016-10-31 | 2017-03-15 | 中国工程物理研究院材料研究所 | A kind of hydroxyl melon ring/graphene oxide composite material and preparation method thereof |
| CN110368988A (en) * | 2019-08-13 | 2019-10-25 | 辽宁大学 | A kind of vitamin B12With the difunctional graphite alkene catalysis material of ruthenium complex and its preparation method and application |
| CN111013579A (en) * | 2019-11-20 | 2020-04-17 | 珠海复旦创新研究院 | Limited-area carbon material loaded with palladium single atom or palladium nano-particles and preparation method thereof |
| CN111013579B (en) * | 2019-11-20 | 2022-07-05 | 珠海复旦创新研究院 | Limited-area carbon material loaded with palladium single atom or palladium nano-particles and preparation method thereof |
| CN114016071A (en) * | 2021-07-29 | 2022-02-08 | 中国科学院福建物质结构研究所 | Multi-element copper-based composite material and preparation method and application thereof |
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