CN114345409A - Preparation method of nano-loaded Cu ionic liquid catalyst - Google Patents
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 72
- 238000002360 preparation method Methods 0.000 title claims abstract description 38
- 239000003054 catalyst Substances 0.000 title claims abstract description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 43
- HVUUVUMACNYXNA-UHFFFAOYSA-N 4-(2-pyridin-4-ylsulfanylethylsulfanyl)pyridine Chemical compound C=1C=NC=CC=1SCCSC1=CC=NC=C1 HVUUVUMACNYXNA-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000005543 nano-size silicon particle Substances 0.000 claims abstract description 18
- 235000012239 silicon dioxide Nutrition 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 6
- 238000013329 compounding Methods 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 26
- 238000001035 drying Methods 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 238000010992 reflux Methods 0.000 claims description 13
- 239000008346 aqueous phase Substances 0.000 claims description 10
- 239000012295 chemical reaction liquid Substances 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 6
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 claims description 5
- MPZMVUQGXAOJIK-UHFFFAOYSA-N 4-bromopyridine;hydron;chloride Chemical compound Cl.BrC1=CC=NC=C1 MPZMVUQGXAOJIK-UHFFFAOYSA-N 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 5
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 5
- 239000012141 concentrate Substances 0.000 claims description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 5
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims description 4
- 239000002105 nanoparticle Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 3
- 239000013504 Triton X-100 Substances 0.000 claims description 3
- 229920004890 Triton X-100 Polymers 0.000 claims description 3
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims description 3
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 claims description 3
- 229910021590 Copper(II) bromide Inorganic materials 0.000 claims description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 claims description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(II) bromide Substances [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 claims description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 abstract description 7
- -1 1, 4-disubstituted 1,2, 3-triazole Chemical class 0.000 abstract description 5
- 238000009776 industrial production Methods 0.000 abstract description 4
- 239000007787 solid Substances 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000007210 heterogeneous catalysis Methods 0.000 abstract 1
- 238000007172 homogeneous catalysis Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 238000005406 washing Methods 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
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- 238000001291 vacuum drying Methods 0.000 description 3
- 238000011068 loading method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
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- 230000010355 oscillation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
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Abstract
The invention relates to a catalyst, and in particular relates to a preparation method of a nano-loaded Cu ionic liquid catalyst. The method comprises the following steps: firstly, preparing nano silicon dioxide and 1, 2-bis (4-pyridylthio) ethane; secondly, preparing the supported nano ionic liquid by using nano silicon dioxide and 1, 2-bis (4-pyridylthio) ethane as raw materials; and finally, compounding the supported nano ionic liquid and the Cu (II) compound to obtain the supported nano Cu ionic liquid. Compared with the traditional catalyst synthesis, the ionic liquid is loaded on the surface of the solid carrier, so that the dosage of the ionic liquid can be greatly reduced, and the catalytic system has great advantages in homogeneous catalysis and heterogeneous catalysis. The catalyst prepared by the method has good catalytic effect in catalyzing various 1, 4-disubstituted 1,2, 3-triazole reactions, can greatly reduce the cost of the ionic liquid, has high repeated utilization rate, and is suitable for industrial production.
Description
Technical Field
The invention relates to a catalyst, and in particular relates to a preparation method of a nano-loaded Cu ionic liquid catalyst.
Background
In recent years, ionic liquids have attracted attention because of their advantages such as low vapor pressure, wide liquid range, and good thermal and chemical stability as compared to conventional solvents. At present, the ionic liquid is loaded on the surface of a solid carrier which is easy to recover to prepare a loaded ionic liquid catalyst, so that the dosage of the ionic liquid can be reduced, and the catalyst has the advantages of high activity, high selectivity and easiness in recycling. The ionic liquid with different roles in the supported ionic liquid catalyst plays different roles, and the ionic liquid can be used as a solvent of a catalytic active center to assist in supporting the active center and can also be used for changing and adjusting the surrounding microenvironment of the active center on the surface of the catalyst.
In metal conversion, the Cu (II) compound has wide application in the field of catalysts due to the advantages of low cost, high selectivity, good catalytic performance and the like. The catalyst obtained by compounding the Cu (II) compound and the supported nano ionic liquid has the advantages of the supported nano ionic liquid and the Cu (II) compound, has good catalytic effect in catalyzing organic reactions, particularly various 1, 4-disubstituted 1,2, 3-triazole reactions, can greatly reduce the cost of the ionic liquid, has high repeated utilization rate, and is suitable for industrial production. At present, no report is made on the preparation method of the catalyst.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a preparation method of a nano-load Cu ionic liquid catalyst, and the catalyst prepared by the method has good catalytic effect in catalyzing various 1, 4-disubstituted 1,2, 3-triazole reactions, can greatly reduce the cost of ionic liquid, has high repeated utilization rate and is suitable for industrial production.
The preparation method of the nano-loaded Cu ionic liquid catalyst comprises the following steps:
firstly, preparing nano silicon dioxide and 1, 2-bis (4-pyridylthio) ethane; secondly, preparing the supported nano ionic liquid by using nano silicon dioxide and 1, 2-bis (4-pyridylthio) ethane as raw materials; and finally, compounding the supported nano ionic liquid and the Cu (II) compound to obtain the supported nano Cu ionic liquid.
Preferably, the preparation method of the nano-loading Cu ionic liquid catalyst specifically comprises the following steps:
(1) preparing nano silicon dioxide:
adding a certain amount of cyclohexane, alcohol and surfactant, then transferring water, and stirring for reaction at room temperature; then, adding tetraethoxysilane into the reaction liquid to continue the reaction; and centrifuging the reaction solution to obtain the nano silicon dioxide.
(2) Preparation of 1, 2-bis (4-pyridylthio) ethane:
adding 4-bromopyridine hydrochloride, 1, 2-ethanedithiol and sodium hydroxide into DMF for reaction; after the reaction is finished, extracting and layering to obtain an aqueous phase and an organic phase, then carrying out reduced pressure concentration on the aqueous phase, and finally recrystallizing the obtained concentrate to obtain the 1, 2-bis (4-pyridylthio) ethane.
(3) Preparing a supported nano ionic liquid:
adding nano silicon dioxide and 1, 2-bis (4-pyridylthio) ethane into DMF (dimethyl formamide) for refluxing, centrifuging reaction liquid, and drying to obtain nano particles; and adding the obtained nano particles and toluene into methyl iodide to react at room temperature, centrifuging the reaction solution after the reaction is finished, and drying to obtain the supported nano ionic liquid.
(4) Preparing a supported nano Cu ionic liquid:
and adding the Cu (II) compound and the supported nano ionic liquid into alcohol for refluxing, and after the reaction is finished, centrifuging and drying the reaction liquid to obtain the supported nano Cu ionic liquid.
Wherein:
in the preparation of the nano silicon dioxide, the alcohol is one or more of n-butyl alcohol, n-amyl alcohol, n-hexyl alcohol, n-heptyl alcohol or n-octyl alcohol.
In the preparation of the nano silicon dioxide, the surfactant is one or more of cetyl trimethyl ammonium bromide, sodium dodecyl benzene sulfonate, sodium dodecyl sulfate or triton X-100.
In the preparation of 1, 2-bis (4-pyridylthio) ethane, the solvent used for recrystallization is methanol or ethanol.
In the preparation of the load type nano ionic liquid, the reflux time is 4-6 h, and the drying temperature is 50-60 ℃.
In the preparation of the supported nano Cu ionic liquid, alcohol is methanol or ethanol, the reflux time is 20-24 h, and the drying temperature is 40-50 ℃; the Cu (II) complex being Cu (OTF)2、CuCl2、CuBr2Or CuSO4One of (1), preferably Cu (OTF)2。
Compared with the prior art, the invention has the following beneficial effects:
(1) by loading the ionic liquid on the nano silicon dioxide, the dosage of the ionic liquid can be greatly reduced, so that the production cost is reduced;
(2) the device for preparing the nano-load Cu ionic liquid catalyst is simple, easy to operate, mild in reaction condition and suitable for industrial production;
(3) the nano-loaded Cu ionic liquid catalyst can be used for catalyzing 1, 4-disubstituted 1,2, 3-triazole reaction, and has good catalytic effect and high repeated utilization rate. The 1, 4-disubstituted 1,2, 3-triazole is prepared by using the nano-loaded Cu ionic liquid for catalysis, the dosage of the catalyst is 2-5%, the product yield reaches more than 92%, and the reaction time is shortened by 1/3 compared with the common catalyst.
Detailed Description
The present invention will be further illustrated with reference to the following specific examples, but the present invention is not limited to the following examples. The method is a conventional method unless otherwise specified. The starting materials are commercially available from the open literature unless otherwise specified.
Example 1
(1) Preparation of nano-silica
Preparing a mixed solution of n-hexanol (35ml) and hexadecyl trimethyl ammonium bromide (35g), adding cyclohexane (165ml), uniformly oscillating with ultrasound, adding water (10ml), stirring at room temperature for 30min, and finally adding tetraethoxysilane to continue reacting. Centrifuging, washing with ethanol, and vacuum drying at 100 deg.C for 2 hr to obtain nanometer silica.
(2) Preparation of 1, 2-bis (4-pyridylthio) ethane
4-bromopyridine hydrochloride (10g), 1, 2-ethanedithiol (3ml) and sodium hydroxide (2.5g) are added into DMF (100ml) for reflux reaction for 20 h; after the reaction is finished, adding a certain amount of water and ethyl acetate into the reaction solution, filtering, extracting and layering the filtrate to obtain an aqueous phase and an organic phase, concentrating the aqueous phase under reduced pressure, and finally recrystallizing the obtained concentrate with methanol to obtain the 1, 2-bis (4-pyridylthio) ethane.
(3) Preparation of supported nano ionic liquid
Adding nano silicon dioxide (5.0g), 1, 2-bis (4-pyridylthio) ethane (2g) and DMF (60ml) into a round-bottom flask, condensing and refluxing for 4h at 80 ℃, centrifuging reaction liquid, washing the obtained solid product with methanol, and drying at 40 ℃; and mixing 5g of dried powder with toluene (50ml), adding the mixture into iodomethane (2.5g) at room temperature, stirring for reaction, centrifuging after the reaction is finished, washing a product with petroleum ether, and drying the product at 50 ℃ to obtain the supported nano ionic liquid.
(4) Preparation of supported nano Cu ionic liquid
Mixing Cu (OTF)2(20mg) and supported nano ionic liquid (5g) are added into ethanol (50ml) and refluxed for 20 h. And after the reaction is finished, centrifuging the reaction solution, washing the obtained solid material with methanol, and drying at 40 ℃ to obtain the supported nano Cu ionic liquid.
Example 2
(1) Preparation of nano-silica
Preparing a mixed solution of n-octanol (35ml) and triton X-100(35g), adding cyclohexane (165ml), performing ultrasonic oscillation uniformly, adding water (10ml), stirring at room temperature for 30min, and finally adding tetraethoxysilane for continuous reaction. Centrifuging, washing with ethanol, and vacuum drying at 100 deg.C for 2 hr to obtain nanometer silica.
(2) Preparation of 1, 2-bis (4-pyridylthio) ethane
4-bromopyridine hydrochloride (10g), 1, 2-ethanedithiol (3ml) and sodium hydroxide (2.5g) are added into DMF (100ml) for reflux reaction for 20 h; after the reaction is finished, adding a certain amount of water and ethyl acetate into the reaction solution, filtering, extracting and layering the filtrate to obtain an aqueous phase and an organic phase, concentrating the aqueous phase under reduced pressure, and finally recrystallizing the obtained concentrate with methanol to obtain the 1, 2-bis (4-pyridylthio) ethane.
(3) Preparation of supported nano ionic liquid
Adding nano silicon dioxide (5.0g), 1, 2-bis (4-pyridylthio) ethane (2g) and DMF (60ml) into a round-bottom flask, condensing and refluxing for 5 hours at 80 ℃, centrifuging reaction liquid, washing the obtained solid product with methanol, and drying at 40 ℃; mixing 5g of dried powder with toluene (50ml), adding the mixture into iodomethane (2.5g) at room temperature, stirring for reaction, centrifuging after the reaction is finished, washing a product with petroleum ether, and drying the product at 55 ℃ to obtain the supported nano ionic liquid.
(4) Preparation of supported nano Cu ionic liquid
Mixing Cu (OTF)2(20mg) and supported nano ionic liquid (5g) are added into ethanol (50ml) and refluxed for 22 h. And after the reaction is finished, centrifuging the reaction solution, washing the obtained solid material with methanol, and drying at 45 ℃ to obtain the supported nano Cu ionic liquid.
Example 3
(1) Preparation of nano-silica
Preparing a mixed solution of n-amyl alcohol (35ml) and sodium dodecyl benzene sulfonate (35g), adding cyclohexane (165ml), uniformly oscillating by ultrasonic, transferring water (10ml), stirring at room temperature for 30min, and finally adding tetraethoxysilane to continue reacting. Centrifuging, washing with ethanol, and vacuum drying at 100 deg.C for 2 hr to obtain nanometer silica.
(2) Preparation of 1, 2-bis (4-pyridylthio) ethane
4-bromopyridine hydrochloride (1g), 1, 2-ethanedithiol (0.3ml) and sodium hydroxide (0.3g) are added into DMF (10ml) and reacted for 24h at 80 ℃; after the reaction is finished, adding a certain amount of water and ethyl acetate into the reaction solution, filtering, extracting and layering the filtrate to obtain an aqueous phase and an organic phase, concentrating the aqueous phase under reduced pressure, and finally recrystallizing the obtained concentrate with methanol to obtain the 1, 2-bis (4-pyridylthio) ethane.
(3) Preparation of supported nano ionic liquid
Adding nano silicon dioxide (5.0g), 1, 2-bis (4-pyridylthio) ethane (2g) and DMF (60ml) into a round-bottom flask, condensing and refluxing for 6h at 80 ℃, centrifuging reaction liquid, washing the obtained solid product with methanol, and drying at 40 ℃; mixing 5g of dried powder with toluene (50ml), adding the mixture into iodomethane (2.5g) at room temperature, stirring for reaction, centrifuging after the reaction is finished, washing the product with petroleum ether, and drying the product at 60 ℃ to obtain the supported nano ionic liquid.
(4) Preparation of supported nano Cu ionic liquid
Mixing Cu (OTF)2(20mg) and supported nano ionic liquid (5g) are added into ethanol (50ml) and refluxed for 24 h. And after the reaction is finished, centrifuging the reaction solution, washing the obtained solid material with ethanol, and drying at 60 ℃ to obtain the supported nano Cu ionic liquid.
The principles and embodiments of the present invention are explained herein using specific examples, which are presented only to assist in understanding the core concepts of the present invention. It should be noted that, for those skilled in the art, it is possible to make various improvements and modifications to the present invention without departing from the principle of the present invention, and those improvements and modifications also fall within the scope of the claims of the present invention.
Claims (10)
1. A preparation method of a nano-loaded Cu ionic liquid catalyst is characterized by comprising the following steps: firstly, preparing nano silicon dioxide and 1, 2-bis (4-pyridylthio) ethane; secondly, preparing the supported nano ionic liquid by using nano silicon dioxide and 1, 2-bis (4-pyridylthio) ethane as raw materials; and finally, compounding the supported nano ionic liquid and the Cu (II) compound to obtain the supported nano Cu ionic liquid.
2. The preparation method of the nano-supported Cu ionic liquid catalyst according to claim 1, characterized in that: the preparation steps of the nano silicon dioxide are as follows: adding a certain amount of cyclohexane, alcohol and surfactant, then transferring water, and stirring for reaction at room temperature; then, adding tetraethoxysilane into the reaction liquid to continue the reaction; and centrifuging the reaction solution to obtain the nano silicon dioxide.
3. The preparation method of the nano-supported Cu ionic liquid catalyst according to claim 2, characterized in that: the alcohol is one or more of n-butanol, n-pentanol, n-hexanol, n-heptanol or n-octanol.
4. The preparation method of the nano-supported Cu ionic liquid catalyst according to claim 2, characterized in that: the surfactant is one or more of cetyl trimethyl ammonium bromide, sodium dodecyl benzene sulfonate, sodium dodecyl sulfate or Triton X-100.
5. The preparation method of the nano-supported Cu ionic liquid catalyst according to claim 1, characterized in that: the preparation steps of the 1, 2-di (4-pyridylthio) ethane are as follows: adding 4-bromopyridine hydrochloride, 1, 2-ethanedithiol and sodium hydroxide into DMF for reaction; after the reaction is finished, extracting and layering to obtain an aqueous phase and an organic phase, then carrying out reduced pressure concentration on the aqueous phase, and finally recrystallizing the obtained concentrate to obtain the 1, 2-bis (4-pyridylthio) ethane.
6. The method for preparing a nano-supported Cu ionic liquid catalyst according to claim 5, wherein: the solvent used for recrystallization is methanol or ethanol.
7. The preparation method of the nano-supported Cu ionic liquid catalyst according to claim 1, characterized in that: the preparation method of the supported nano ionic liquid comprises the following steps: adding nano silicon dioxide and 1, 2-bis (4-pyridylthio) ethane into DMF (dimethyl formamide) for refluxing, centrifuging reaction liquid, and drying to obtain nano particles; and adding the obtained nano particles and toluene into methyl iodide to react at room temperature, centrifuging the reaction solution after the reaction is finished, and drying to obtain the supported nano ionic liquid.
8. The method for preparing a nano-supported Cu ionic liquid catalyst according to claim 7, wherein: the reflux time is 4-6 h, and the drying temperature is 50-60 ℃.
9. The preparation method of the nano-supported Cu ionic liquid catalyst according to claim 1, characterized in that: the preparation method of the supported nano Cu ionic liquid comprises the following steps: and adding the Cu (II) compound and the supported nano ionic liquid into alcohol for refluxing, and after the reaction is finished, centrifuging and drying the reaction liquid to obtain the supported nano Cu ionic liquid.
10. The preparation method of the nano-loaded Cu ionic liquid catalyst according to claim 9, characterized in that: the alcohol is methanol or ethanol, the reflux time is 20-24 h, and the drying temperature is 40-50 ℃; the Cu (II) complex being Cu (OTF)2、CuCl2、CuBr2Or CuSO4One kind of (1).
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