CN117364110A - Method for directly and electrochemically oxidizing C-H bond to controllably convert into aldehyde and ketone - Google Patents
Method for directly and electrochemically oxidizing C-H bond to controllably convert into aldehyde and ketone Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 39
- 150000001299 aldehydes Chemical class 0.000 title claims abstract description 9
- 150000002576 ketones Chemical class 0.000 title claims abstract description 9
- 230000001590 oxidative effect Effects 0.000 title abstract description 6
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 claims abstract description 73
- WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 claims abstract description 73
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- 238000005868 electrolysis reaction Methods 0.000 claims abstract description 24
- 239000007772 electrode material Substances 0.000 claims abstract description 17
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 239000003115 supporting electrolyte Substances 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 229910052745 lead Inorganic materials 0.000 claims abstract description 5
- 229910013684 LiClO 4 Inorganic materials 0.000 claims abstract description 4
- 229910020808 NaBF Inorganic materials 0.000 claims abstract description 4
- 239000012046 mixed solvent Substances 0.000 claims abstract description 4
- 239000003792 electrolyte Substances 0.000 claims abstract 2
- 238000006056 electrooxidation reaction Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 230000036632 reaction speed Effects 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000000376 reactant Substances 0.000 abstract description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- ARRNBPCNZJXHRJ-UHFFFAOYSA-M hydron;tetrabutylazanium;phosphate Chemical compound OP(O)([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC ARRNBPCNZJXHRJ-UHFFFAOYSA-M 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101000653548 Homo sapiens Trichoplein keratin filament-binding protein Proteins 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 241001274216 Naso Species 0.000 description 1
- 102100030645 Trichoplein keratin filament-binding protein Human genes 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YCCHNFGPIFYNTF-UHFFFAOYSA-N tertiary cymene hydroperoxide Natural products CC1=CC=C(C(C)(C)OO)C=C1 YCCHNFGPIFYNTF-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/07—Oxygen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/23—Oxidation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Abstract
The invention discloses a method for directly and electrochemically oxidizing and controllably converting C-H bonds into aldehydes and ketones, which is characterized by comprising the following steps: the method comprises the following steps: adding p-isopropyl toluene, supporting electrolyte and solvent into a diaphragm-free electrolytic tank to form electrolyte, wherein the anode electrode material and the cathode electrode material are C/C, C/Pb, pt/C, pt/Pt and Pt/Pb respectively, and generating p-isopropyl benzaldehyde and p-methylacetophenone through constant current electrolysis; the solvent is CH 3 CN and H 2 A mixed solvent of O, wherein the supporting electrolyte is NaBF 4 、LiClO 4 Or SDS; the constant current electrolysis conditions are as follows: the temperature is 20-60 ℃ and the current density is 16-34 mA/cm 2 The rotating speed is more than or equal to 500rpm, and the electrolysis time is 2-12 h. The invention has the advantages of environment protection, low cost, simple and safe operation, high reactant conversion rate and target yieldThe yield of the product is high, and the industrialization is more facilitated.
Description
Technical Field
The invention belongs to the field of electromechanical chemical synthesis, and in particular relates to a constant current electrolysis method for controllably converting p-isopropyl toluene into corresponding aldehyde and ketone.
Background
P-isopropyl toluene (PIT), commonly known as p-cymene, has different types of C-H bonds in its molecule, and by controllable conversion, p-isopropyl benzaldehyde (PIBA), an important fine chemical intermediate, can be converted to p-methylacetophenone (PMAP) accordingly. PIBA is used as a fragrance, and has also been used in the medical industry for its antimicrobial, anti-inflammatory, antifungal, hypoglycemic and anticancer functions (Life Sciences,2022, 298:120525.). PMAP is used both as a flavoring agent and as an intermediate for the production of active pharmaceuticals, perfumes and cosmetics (The Journal of Chemical Thermodynamics,2023, 185:107108.). The conversion to the corresponding aldehydes or ketones by oxidation of C-H bonds is of great interest in organic chemistry, where direct functionalization of the C-H bonds is attractive but also challenging, especially for C (sp 3 ) Functionalization of H bonds (Nature, 2016,533 (7602):230-234.). Conventional chemical oxidation processes typically require harsh conditions, such as high temperature, high pressure, chemical oxidants (O 2 、H 2 O 2 Etc.), while some transition metals are required as catalysts, three wastes are serious. Roman V.Ottenbacher et al uses Mn-based catalysts in H 2 O 2 PIT is catalyzed under conditions with a conversion of up to 52% and with a PMAP yield of 6% (ACS catalyst.2021, 11, 5517-5524). The electrochemical oxidation method is clean and efficient, and can achieve certain controllability by setting certain potential or current. However, the yields of products of the electrochemical oxidation processes reported to date for the preparation of aldehydes and/or ketones remain to be increased.
Disclosure of Invention
In view of the above problems, the present invention provides a constant current electrolytic oxidation method for the controllable conversion of p-isopropylbenzaldehyde into p-isopropylbenzaldehyde (PIBA) and p-methylacetophenone (PMAP) to increase the overall yield of the product.
In order to achieve the above purpose, the invention adopts the following technical scheme:
a method for the controlled conversion of C-H bonds to aldehydes and ketones by direct electrochemical oxidation, said method comprising: adding p-isopropyl toluene into a diaphragm-free electrolytic tank to support electrolysisElectrolyte is composed of a solvent and a substance, anode electrode materials and cathode electrode materials are C/C, C/Pb, pt/C, pt/Pt and Pt/Pb respectively, and p-isopropylbenzaldehyde and p-methylacetophenone are generated through constant current electrolysis; the solvent is CH 3 CN and H 2 Mixed solvent of O, wherein H 2 The content of O is 10-20%, and the supporting electrolyte is NaBF 4 、LiClO 4 Or SDS; the constant current electrolysis conditions are as follows: the temperature is 20-60 ℃ and the current density is 16-34 mA/cm 2 The rotating speed is more than or equal to 500rpm, and the electrolysis time is 2-12 h.
Preferably, the electrolysis reaction temperature is 50 to 60 ℃.
Preferably, the cathode electrode material and the anode electrode material are C/Pb, pt/C, pt/Pt or Pt/Pb respectively.
Preferably, the current density is 22-34 mA/cm 2 Further preferably 28mA/cm 2 。
Preferably, the reaction speed is 500rpm to 1500rpm, more preferably 1500rpm.
Preferably, the electrolysis reaction time is 12 hours.
According to the method for directly and electrochemically oxidizing and controllably converting the C-H bond of the p-isopropylbenzaldehyde into the p-isopropylbenzaldehyde and the p-methylacetophenone, after the electrolysis is finished, the obtained reaction mixed solution is subjected to rotary evaporation and extraction, and column chromatography purification is carried out to obtain the target products of the p-isopropylbenzaldehyde and the p-methylacetophenone.
Compared with the prior art, the invention has the beneficial effects that:
(1) The present invention uses an electrochemical process in which water provides an oxygen source without the addition of an additional chemical oxidant, which is an environmentally friendly process.
(2) Compared with constant potential electrolysis, the method provided by the invention has higher selectivity on the target product, and is more suitable for industrialization.
(3) The cathode electrode material and the anode electrode material adopt C, pb and Pt, and special modification and pretreatment are not needed.
(4) The invention does not need to add acid or alkali as an additive, does not use noble metal as an electrode, has low cost, simple and convenient operation and safety, and is more beneficial to industrialization.
(5) The method has high reactant conversion rate and almost complete conversion in 12 hours.
(6) The method for directly and electrochemically oxidizing and controllably converting the C-H bond into aldehyde and ketone has high yield of target products of p-isopropylbenzaldehyde and p-methylacetophenone.
Detailed Description
The following are specific examples of the present invention for better understanding of the present invention, and the technical solutions of the present invention are further described, but the present invention is not limited to these examples.
The structural formula of the PIT used in the following examples is shown in the following formula (I):
the structures of the PIBA and the PMAP which are correspondingly prepared are shown in formulas (II-III):
the synthetic route is as follows:
on CH 3 CN/H 2 In addition to the above-mentioned products (II) and (III) in the O solution, the products which may be formed are:
the electrolysis steps and results for controllably generating PIBA and PMAP by taking PIT as raw materials are as follows:
the scheme is adopted in CH 3 CN/H 2 In O mixed solvent, by controlling the reactionConditions should be used to obtain different yields of PIBA and PMAP. The specific operation is as follows:
example 1:
a50 mL electrolytic cell was charged with 0.2013g PIT,0.1647g supporting electrolyte NaBF 4 ,30ml CH 3 CN/H 2 The O mixed solution (volume ratio is 9:1) is taken as a solvent, a C rod is taken as a cathode electrode material and an anode electrode material, the rotating speed is 1000rpm, the temperature is 20 ℃, and the rotating speed is 22mA/cm 2 Constant current electrolysis is carried out for 12 hours under the current density to obtain target products PIBA and PMAP. The yield of the electrolysis product was analyzed by a gas chromatograph-mass spectrometer, the analysis method was an area normalization method, and the yield of the product is shown in table 1. The reaction solution was purified by rotary evaporation, extraction and column chromatography (petroleum ether/ethyl acetate=10:1), and then subjected to structural characterization.
The product PIBA structure is characterized as: 1 HNMR(500MHz,CDCl 3 )δ:9.97(s,1H),7.81(d,J=8.1Hz,2H),7.38(d,J=8.1Hz,2H),2.99(hept,J=6.9Hz,1H),1.28(d,J=6.9Hz,6H),GC-MS(EI,70eV)m/z:148.08[M] + 。
the product PMAP structure is characterized as: 1 HNMR(500MHz,CDCl 3 )δ:7.88(d,J=8.1Hz,2H),7.28(d,J=8.1Hz,2H),2.60(s,3H),2.43(s,3H),GC-MS(EI,70eV)m/z:134.06[M] + 。
examples 2-3, comparative example 1:
the procedure and procedure were as in example 1, except that CH was changed 3 CN/H 2 CH in O mixed solution 3 CN and H 2 O ratio, the above constant current electrolysis experiment was performed, and the results are shown in Table 1.
TABLE 1 different CH 3 CN/H 2 PIT controllable generation of PIBA and PMAP under O proportion
As can be seen from Table 1, H in the solvent 2 The content of O has a great influence on the yield of the products PIBA and PMAP, and the yield of the products PIBA and PMAP is higher than that of the products PIBA and PMAP in CH 3 CN/H 2 When the O volume ratio is 9:1, the PIBA yield is highest, and the conversion rate of the reaction substrate is also highest.
Examples 4-8:
the reaction procedure and reaction procedure were as in example 1, except that the reaction temperatures were 30 ℃ (example 4), 40 ℃ (example 5), 50 ℃ (example 6), 60 ℃ (example 7), 70 ℃ (example 8) and constant current electrolysis experiments were conducted, and the results are shown in table 2.
TABLE 2 PIT controlled formation of PIBA and PMAP at different reaction temperatures
From the above table it is clear that the conversion of the reaction substrate is essentially unchanged below 70 ℃, but as the reaction temperature increases, the yield of PMAP increases gradually, whereas the yield of PIBA decreases gradually, probably because a greater activation energy is required for extracting H atoms from the tertiary carbon of the isopropyl group, whereby increasing the temperature favors the production of PMAP and at lower temperatures favors the conversion to PIBA.
Examples 9 to 12:
the procedure and procedure were as in example 7, except that the supporting electrolyte in the reaction system was changed to 0.5129g TBAP (example 9) and 0.1596g LiClO, respectively, equimolar 4 (example 10), 0.2581g CF 3 NaSO 3 (example 11), 0.4326g of Sodium Dodecyl Sulfate (SDS) (example 12) was subjected to a constant current electrolysis test, and the results are shown in Table 3.
TABLE 3 PIT controlled production of PIBA and PMAP with different supporting electrolytes
As can be seen from Table 3, the supporting electrolyte has an effect on the conversion of the reaction substrate and the yield of both products, wherein LiClO 4 The use of SDS as a supporting electrolyte is more advantageous for the production of PMAP and PIBA.
Examples 13 to 17:
the reaction procedure and reaction procedure were the same as in example 7, except that the cathode and anode electrode materials were changed to other electrode materials, respectively, C/Pt (example 13), C/Pb (example 14), pt/C (example 15), pt/Pt (example 16) and Pt/Pb (example 17), and a constant current electrolysis experiment was conducted. The results are shown in Table 4.
TABLE 4 PIT controlled formation of PIBA and PMAP for different electrode materials
As can be seen from table 4, the electrode material has a large influence on the PIT direct electrooxidation reaction, and the yield of PMAP is highest when C is used as the anode and Pb is used as the cathode, whereas the yield of PIBA is highest when both the cathode and anode are Pt.
Examples 18 to 20:
the procedure and the reaction procedure were as in example 14, except that the reaction conditions were changed, and 0.05mol/L NaOH (example 18) and 0.05mol/L H were added, respectively 2 SO 4 Example 19 and 0.1mol/L H 2 SO 4 (example 20) constant current electrolysis experiments were performed and the results are shown in Table 5.
TABLE 5 PIT controlled formation of PIBA and PMAP at different pH' s
As can be seen from Table 5, solutions of different pH have an effect on the yields of both products, with PIBA formation being favored under alkaline conditions and PMAP formation being favored in acidic conditions, probably because the hydroxyl groups of the hydroperoxide intermediate (TCHP) formed in the reaction are more readily acidified, especially at 0.05mol/L H 2 SO 4 The yield of PMAP is highest in the environment.
Examples 21 to 23:
the reaction procedure and the reaction procedure were the same as in example 14, except that the current density was changed to 16mA/cm 2 (example 21), 28mA/cm 2 Example 22 and 34mA/cm 2 Example 23 the above constant current electrolysis experiment was performed and the results are shown in table 6.
TABLE 6 PIT controlled generation of PIBA and PMAP at different current densities
As is clear from Table 6, the PIT yields of PIBA and PMAP at different current densities have similar rules, and the moderate current density is advantageous for both products, so that the preferred current density is 28mA/cm 2 。
Examples 24 to 25:
the reaction procedure and the reaction procedure were the same as in example 22, except that the rotation speed was changed to 500rpm (example 24), and a constant current electrolysis test was conducted at 1500rpm (example 25), and the results are shown in Table 7.
TABLE 7 PIT controllable generation of PIBA and PMAP at different rotational speeds
As can be seen from Table 7, the rotational speed also has a certain effect on the yields of the products PIBA and PMAP. The yield of PMAP increases gradually with increasing rotational speed, and the yield of PMAP is highest at 1500rpm, probably because the reaction is affected by diffusion control. While the yield of the product PIBA remains relatively stable with increasing rotational speed.
The present invention is not limited to the preferred embodiments, and any simple modification, equivalent replacement, and improvement made to the above embodiments by those skilled in the art without departing from the technical scope of the present invention, will fall within the scope of the present invention.
Claims (8)
1. A process for the controlled conversion of C-H bonds to aldehydes and ketones by direct electrochemical oxidation, characterized in that: the method comprises the following steps: adding p-isopropyl toluene, supporting electrolyte and solvent into a diaphragm-free electrolytic tank to form electrolyte, and anode and cathode electrodesThe electrode materials are C/C, C/Pb, pt/C, pt/Pt and Pt/Pb respectively, and p-isopropylbenzaldehyde and p-methylacetophenone are generated through constant current electrolysis; the solvent is CH 3 CN and H 2 Mixed solvent of O, wherein H 2 The content of O is 10-20%, and the supporting electrolyte is NaBF 4 、LiClO 4 Or SDS; the constant current electrolysis conditions are as follows: the temperature is 20-60 ℃ and the current density is 16-34 mA/cm 2 The rotating speed is more than or equal to 500rpm, and the electrolysis time is 2-12 h.
2. The method of claim 1, wherein: the temperature of the electrolytic reaction is 50-60 ℃.
3. The method of claim 1, wherein: the cathode electrode material and the anode electrode material are C/Pb, pt/C, pt/Pt or Pt/Pb respectively.
4. The method of claim 1, wherein: the current density is 22-34 mA/cm 2 。
5. The method of claim 4, wherein: the current density is 28mA/cm 2 。
6. The method of claim 1, wherein: the reaction rotating speed is 500 rpm-1500 rpm.
7. The method of claim 6, wherein: the reaction speed was 1500rpm.
8. The method of claim 1, wherein: the electrolytic reaction time is 12h.
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