CN114656366A - Method for synthesizing 1-aminoanthraquinone by electrochemical reduction method - Google Patents
Method for synthesizing 1-aminoanthraquinone by electrochemical reduction method Download PDFInfo
- Publication number
- CN114656366A CN114656366A CN202210344245.0A CN202210344245A CN114656366A CN 114656366 A CN114656366 A CN 114656366A CN 202210344245 A CN202210344245 A CN 202210344245A CN 114656366 A CN114656366 A CN 114656366A
- Authority
- CN
- China
- Prior art keywords
- aminoanthraquinone
- cathode
- electrode
- anode
- electrolyte
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 40
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 6
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims abstract description 18
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 239000003792 electrolyte Substances 0.000 claims abstract description 13
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000758 substrate Substances 0.000 claims abstract description 9
- 239000010936 titanium Substances 0.000 claims abstract description 9
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 9
- HTXDPTMKBJXEOW-UHFFFAOYSA-N dioxoiridium Chemical compound O=[Ir]=O HTXDPTMKBJXEOW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
- 238000005868 electrolysis reaction Methods 0.000 claims description 9
- 230000003647 oxidation Effects 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 229910001220 stainless steel Inorganic materials 0.000 claims description 7
- 239000010935 stainless steel Substances 0.000 claims description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 239000012528 membrane Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 2
- 239000010405 anode material Substances 0.000 claims description 2
- 239000010406 cathode material Substances 0.000 claims description 2
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 13
- 239000002351 wastewater Substances 0.000 abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 239000001301 oxygen Substances 0.000 abstract description 3
- 239000007772 electrode material Substances 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 description 19
- 150000001450 anions Chemical class 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- -1 amino compound Chemical class 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 208000008763 Mercury poisoning Diseases 0.000 description 1
- 206010027439 Metal poisoning Diseases 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
- C25B3/25—Reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- 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
- C25B3/09—Nitrogen containing compounds
Landscapes
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of dye production, and particularly relates to a method for electrochemically synthesizing 1-aminoanthraquinone. The method comprises the steps of placing 1-nitroanthraquinone as a raw material in a cathode tank, adopting electrolytes with the same concentration or concentration difference for a cathode and an anode, adopting different electrode materials for the cathode, adopting a titanium substrate loaded with ruthenium dioxide or iridium dioxide as an oxygen-releasing electrode for the anode to obtain a 1-aminoanthraquinone leuco body, and introducing air into the leuco body to be fully oxidized to obtain a red 1-aminoanthraquinone product. The method has the advantages of simple and convenient process for synthesizing the 1-aminoanthraquinone, recyclable electrolyte and green and pollution-free reaction process, solves the problems of high wastewater yield and difficult treatment in the production process of the 1-aminoanthraquinone, reduces the production cost, and is suitable for industrialization.
Description
Technical Field
The invention relates to the technical field of dye production, in particular to a method for producing and synthesizing 1-aminoanthraquinone by an electrochemical reduction method.
Background
The 1-aminoanthraquinone is mainly used for producing the most important intermediate of anthraquinone dyes, and can be used for further producing various disperse dyes, reactive dyes, acid dyes and vat dyes with excellent performance from the 1-aminoanthraquinone. The method can also be used for producing organic pigments and liquid crystal dyes, has wide application range and occupies an important position in the dye market. With the rapid development of the dye industry in China, the demand of 1-aminoanthraquinone increases year by year. In recent years, some countries such as Europe and America have stopped the production of 1-aminoanthraquinone due to the problem of environmental pollution during the production of dyes, and have turned to buying 1-aminoanthraquinone products in developing countries. Under such a domestic and foreign environment, it is urgent to improve the original process or to seek a clean production process for obtaining high-quality 1-aminoanthraquinone.
The synthesis of 1-aminoanthraquinone is mainly carried out by the following methods. The anthraquinone sulfonation and ammonolysis method is the method for industrially producing 1-aminoanthraquinone, but because the method uses mercury-containing compounds, on one hand, the emission of mercury-containing waste water pollutes the environment, and on the other hand, operators can cause mercury poisoning when using the mercury-containing compounds, and the method is stopped at present. At present, the most common method for producing 1-aminoanthraquinone is to nitrify and refine anthraquinone to obtain 1-nitroanthraquinone, and then reduce the 1-aminoanthraquinone by using sodium sulfide to obtain the 1-aminoanthraquinone. The product reduced by the catalytic hydrogenation method only generates water except the amino compound, and is a green and pollution-free advanced process. However, the catalytic hydrogenation method has great limitations, many nitro compounds can not adopt catalytic hydrogenation technology, such as anthraquinone nitro compounds, almost no good solvent exists, the product can not be completely dissolved, and the catalyst can not be separated. In addition, there are some synthetic methods such as naphthoquinone method, hydrazine hydrate method, metal reduction method, etc., which are still in the laboratory due to high production cost and have not been industrialized.
Disclosure of Invention
In order to solve the problems in the existing 1-aminoanthraquinone production process, the invention aims to provide a green and environment-friendly preparation method of 1-aminoanthraquinone so as to obtain a high-quality 1-aminoanthraquinone product.
The invention opens up a new electrochemical process of nitro reduction, designs a new electrolytic cell, selects a proper ionic membrane, selects a proper material as a cathode electrode, uses electrons as a reducing agent, realizes high-efficiency electrochemical nitro reduction, fundamentally avoids pollution and is a high-efficiency pollution-free reaction.
In order to realize the purpose, the invention is realized by the following technical scheme:
1) electrochemical reduction: placing the raw material 1-nitroanthraquinone and electrolyte in a cathode tank, inserting an electrode in an anode tank which is the electrolyte with the same concentration or with concentration difference, introducing direct current to form an electrolytic cell, and reducing the 1-nitroanthraquinone to generate 1-aminoanthraquinone leuco;
2) and (3) oxidation: introducing air into the reaction liquid obtained in the step 1) under stirring to obtain the 1-aminoanthraquinone.
In the step 1), oxygen release reaction is carried out in an anode tank, and 1-nitroanthraquinone is electrochemically reduced in a cathode tank to synthesize the 1-aminoanthraquinone leuco body.
And (3) cathode reaction:
and (3) anode reaction: 6OH-→3/2O2+3H2O+6e-
In the step 2), air is used as an oxidant and is fully oxidized to generate the 1-aminoanthraquinone.
In the technical scheme, the cathode tank and the anode tank of the electrolytic cell in the step 1) are separated by an anion membrane or a cation membrane.
In the above technical solution, further, the anode material in step 1) is a titanium substrate loaded with ruthenium dioxide or iridium dioxide, and the cathode material is a stainless steel electrode, a nickel foam electrode, a copper electrode, or a graphite electrode.
In the technical scheme, the reaction temperature in the step 1) is 30-100 ℃, preferably 50-90 ℃, and the reaction time is 4-12 h.
In the technical scheme, further, the electrolyte in the step 1) is at least one of a sodium carbonate solution, a potassium hydroxide solution, a sodium hydroxide solution and a sulfuric acid solution, and the mass percentage concentration of the electrolyte is 2-20%.
In the above technical solution, further, when the electrolyte with concentration difference is adopted in step 1), the concentration of the anode should be controlled to be higher than that of the cathode, and the concentration difference is 3-25%.
In the technical scheme, the electrolysis in the step 1) is constant current electrolysis, the current is 0.5-2.0A, and the voltage change is below 6V.
In the above technical scheme, further, the reaction temperature in the step 2) is 0-95 ℃, and room temperature is preferred.
The invention has the beneficial effects that:
aiming at the problems of large amount of sulfur-containing wastewater generated by the 1-aminoanthraquinone synthesis process, high production cost and the like, the invention takes a titanium substrate loaded with ruthenium dioxide or iridium dioxide as an oxidation electrode, a stainless steel electrode, a foamed nickel electrode, a copper electrode, a graphite electrode and the like as reduction electrodes, and replaces the traditional process for producing the 1-aminoanthraquinone by a sodium sulfide reduction method with two steps of electrochemical reduction and oxidation. Specifically, the process has the following advantages:
1) the 'electron' is used as a reducing agent, and the reaction can be carried out towards a preset target by changing the potential of the electrode, so that pollution is avoided from the source, and the method is green and environment-friendly.
2) Air is used as an oxidant, so that the method is green and pollution-free and has low cost.
3) The anode only discharges oxygen, and the environment is not polluted.
4) The electrolyte can be recycled, so that the generation of wastewater is reduced, and the production cost is reduced.
Drawings
FIG. 1 is a schematic view of an electrolytic cell of the present invention.
Detailed Description
The following examples further illustrate the invention.
Example 1
Grinding 2.53g of 1-nitroanthraquinone for 5 hours, putting the ground 1-nitroanthraquinone and 175ml of sodium hydroxide solution with the mass percentage concentration of 4.5% into a cathode tank of 300ml, adding 50ml of sodium hydroxide solution with the mass percentage concentration of 4.5% into an anode tank, wherein an oxidation electrode is a titanium substrate loaded with ruthenium dioxide, a reduction electrode is a 316-type stainless steel electrode, an anion diaphragm is used, the reaction temperature is 80 ℃, and the electrolysis is carried out for 8 hours under the constant current of 0.5A, and the voltage is 3.8-5.3V. After the reduction reaction, the 1-aminoanthraquinone leuco body was taken out, and stirred for 4 hours under the condition of introducing air to obtain red 1-aminoanthraquinone, which was recorded as sample-1. The purity of sample-1 was 95.2% (HPLC analysis) and the yield was 96.7%.
Example 2
Grinding 2.53g of 1-nitroanthraquinone for 5 hours, putting the ground 1-nitroanthraquinone and 150ml of sodium carbonate solution with the mass percentage concentration of 2.1% into a cathode tank of 300ml, adding 50ml of sodium carbonate solution with the mass percentage concentration of 2.1% into an anode tank, wherein an oxidation electrode is a titanium substrate loaded with ruthenium dioxide, a reduction electrode is a 316-type stainless steel electrode, an anion diaphragm is used, the reaction temperature is 80 ℃, electrolysis is carried out for 7 hours under the constant current of 0.5A, and the voltage is 2.8-3.6V. After the reduction reaction is finished, taking out the 1-aminoanthraquinone leuco body, and stirring for 4 hours under the condition of introducing air to obtain red 1-aminoanthraquinone. The product purity was 96.6% (HPLC analysis) and the yield was 97.2%.
Example 3
Grinding 2.53g of 1-nitroanthraquinone for 5 hours, putting the ground 1-nitroanthraquinone and 150ml of 2.1 mass percent sodium carbonate solution into a cathode tank of 300ml, adding 50ml of 2.1 mass percent sodium carbonate solution into an anode tank, wherein an oxidation electrode is a titanium substrate loaded with ruthenium dioxide, a reduction electrode is a foamed nickel electrode, an anion diaphragm is used, the reaction temperature is 80 ℃, electrolysis is carried out for 8 hours under the constant current of 0.5A, and the voltage is 2.5-3.8V. After the reduction reaction is finished, taking out the 1-aminoanthraquinone leuco body, and stirring for 4 hours under the condition of introducing air to obtain red 1-aminoanthraquinone. The product purity was 96.2% (HPLC analysis) and the yield was 98.5%.
Example 4
Grinding 2.53g of 1-nitroanthraquinone for 5 hours, putting the ground 1-nitroanthraquinone and 150ml of sodium hydroxide solution with the mass percentage concentration of 2.1% into a cathode tank of 300ml, adding 50ml of sodium hydroxide solution with the mass percentage concentration of 6.0% into an anode tank, wherein an oxidation electrode is a titanium substrate loaded with ruthenium dioxide, a reduction electrode is a 316-type stainless steel electrode, an anion diaphragm is used, the reaction temperature is 80 ℃, and the electrolysis is carried out for 9 hours under the constant current of 0.5A, and the voltage is 2.4-3.3V. After the reduction reaction is finished, taking out the 1-aminoanthraquinone leuco body, and stirring for 4 hours under the condition of introducing air to obtain red 1-aminoanthraquinone. The product purity was 96.6% (HPLC analysis) and the yield was 98.3%.
Example 5
Grinding 2.53g of 1-nitroanthraquinone for 5 hours, putting the ground 1-nitroanthraquinone and 150ml of sodium hydroxide solution with the mass percentage concentration of 2.1% into a cathode tank of 300ml, adding 50ml of sodium hydroxide solution with the mass percentage concentration of 6.0% into an anode tank, wherein an oxidation electrode is a titanium substrate loaded with ruthenium dioxide, a reduction electrode is a 316-type stainless steel electrode, a cation diaphragm is used, the reaction temperature is 80 ℃, electrolysis is carried out for 9 hours under the constant current of 0.5A, and the voltage is 2.0-3.0V. After the reduction reaction is finished, taking out the 1-aminoanthraquinone leuco body, and stirring for 4 hours under the condition of introducing air to obtain red 1-aminoanthraquinone. The product purity was 97.7% (HPLC analysis) and the yield was 99.2%.
The above description is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of changes or substitutions within the technical scope of the present invention, and all such changes or substitutions are included in the scope of the present invention.
Claims (10)
1. A method for electrochemically synthesizing 1-aminoanthraquinone, said method comprising the steps of:
1) electrochemical reduction: placing the raw material 1-nitroanthraquinone and electrolyte in a cathode tank, inserting an electrode in an anode tank which is the electrolyte with the same concentration or with concentration difference, introducing direct current to form an electrolytic cell, and reducing the 1-nitroanthraquinone to generate 1-aminoanthraquinone leuco;
2) and (3) oxidation: introducing air into the reaction liquid obtained in the step 1) under stirring to obtain the 1-aminoanthraquinone.
2. The method according to claim 1, characterized in that the cathode cell and the anode cell of the electrolytic cell in step 1) are separated by an anionic membrane or a cationic membrane.
3. The method as claimed in claim 1, wherein the anode material in step 1) is a titanium substrate loaded with ruthenium dioxide or iridium dioxide, and the cathode material is a stainless steel electrode, a foamed nickel electrode, a copper electrode or a graphite electrode.
4. The method according to claim 1, wherein the reaction temperature in step 1) is 30-100 ℃ and the reaction time is 4-12 h.
5. The method according to claim 1, wherein the reaction temperature in step 1) is 50 to 90 ℃.
6. The method according to claim 1, wherein the electrolyte in the step 1) is at least one of a sodium carbonate solution, a potassium hydroxide solution, a sodium hydroxide solution and a sulfuric acid solution, and the mass percentage concentration of the electrolyte is 2-20%.
7. The method as claimed in claim 1, wherein when the electrolyte having a concentration difference is used in step 1), the concentration of the anode is controlled to be higher than that of the cathode, and the concentration difference is 3-25%.
8. The method according to claim 1, wherein the electrolysis in the step 1) is constant current electrolysis, the current is 0.5-2.0A, and the voltage variation is below 6V.
9. The method according to claim 1, wherein the reaction temperature in step 2) is 0 to 95 ℃.
10. The method according to claim 1, wherein the reaction temperature in step 2) is room temperature.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210344245.0A CN114656366A (en) | 2022-03-31 | 2022-03-31 | Method for synthesizing 1-aminoanthraquinone by electrochemical reduction method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210344245.0A CN114656366A (en) | 2022-03-31 | 2022-03-31 | Method for synthesizing 1-aminoanthraquinone by electrochemical reduction method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114656366A true CN114656366A (en) | 2022-06-24 |
Family
ID=82032850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210344245.0A Pending CN114656366A (en) | 2022-03-31 | 2022-03-31 | Method for synthesizing 1-aminoanthraquinone by electrochemical reduction method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114656366A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0394085A (en) * | 1989-06-12 | 1991-04-18 | Nippon Shokubai Kagaku Kogyo Co Ltd | Production of 1-aminoanthraquinones |
| US5213665A (en) * | 1988-02-29 | 1993-05-25 | Nippon Shokubai Kagaku Kogyo, Co., Ltd. | Process for producing 1-aminoanthraquinones |
| CN101054681A (en) * | 2007-02-14 | 2007-10-17 | 浙江工业大学 | Electrolytic synthesis method for 1,5-diamino-4,8-dihydroxyanthraquinone by one-step method |
-
2022
- 2022-03-31 CN CN202210344245.0A patent/CN114656366A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5213665A (en) * | 1988-02-29 | 1993-05-25 | Nippon Shokubai Kagaku Kogyo, Co., Ltd. | Process for producing 1-aminoanthraquinones |
| JPH0394085A (en) * | 1989-06-12 | 1991-04-18 | Nippon Shokubai Kagaku Kogyo Co Ltd | Production of 1-aminoanthraquinones |
| CN101054681A (en) * | 2007-02-14 | 2007-10-17 | 浙江工业大学 | Electrolytic synthesis method for 1,5-diamino-4,8-dihydroxyanthraquinone by one-step method |
Non-Patent Citations (2)
| Title |
|---|
| 张玉梅: "1-氨基蒽醌的合成", 《鞍山钢铁学院学报》 * |
| 黄培等: "硝基化合物还原制备芳香胺工艺研究进展", 《南京工业大学学报(自然科学版)》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109659143B (en) | Nickel hydroxide/trinickel disulfide/foamed nickel compound and preparation method and application thereof | |
| CN111074291A (en) | Novel water electrolysis hydrogen production process | |
| CN109136973B (en) | Non-noble metal doped molybdenum carbide hydrogen evolution electrode and preparation method and application thereof | |
| CN114016069A (en) | Preparation method and application of gallium oxide-based liquid metal catalyst | |
| CN102021600B (en) | Method and device for producing potassium iodate through oxygen cathode non-diaphragm electrolysis | |
| WO2022068491A1 (en) | Lead nanosheet-graphene two-dimensional composite, preparation method and application thereof | |
| CN101187028B (en) | Potassium ferrate preparation method | |
| WO2024130917A1 (en) | Method for directly preparing trivalent chromium compound by means of electrochemical oxidation of ferrochromium | |
| CN114656366A (en) | Method for synthesizing 1-aminoanthraquinone by electrochemical reduction method | |
| CN105696017B (en) | A kind of new technique method of iron reduction nitrobenzene | |
| CN114525528B (en) | Synthesis method of 1-amino-1, 2, 3-triazole | |
| CN116083930A (en) | Method for synthesizing 1-amino anthraquinone by electrocatalytic hydrogenation by using palladium nanocluster catalyst | |
| CN105862072B (en) | A kind of new technique method of zinc reduction nitrobenzene | |
| CN103266329A (en) | Electrochemical method for synthesizing 2,2'-dichlorohydrazobenzene by use of supported catalyst ionic membrane | |
| CN114059086A (en) | Device and method for two-step electrolytic hydrogen production based on acidic electrolyte | |
| CN113621983A (en) | Method for preparing sebacate compound by anodic decarboxylation oxidative coupling | |
| CN101349017B (en) | Method for reducing sulfur dyes by electrocatalysis | |
| CN117210832A (en) | Method for electrochemically synthesizing 1-naphthylamine | |
| CN117568822A (en) | Method for electrochemical reduction of 4-nitrotoluene-2-sulfonic acid | |
| CN116180113A (en) | Synthesis method of 1-aminoanthraquinone | |
| CN114686908B (en) | Method for directly generating formic acid by high-efficiency electrocatalytic carbon dioxide reduction | |
| CN115418653A (en) | Method for preparing vanadium battery electrolyte by electrolysis through coupling reaction | |
| Konarev | Electrochemical reduction of 4-chloro-2-nitrophenol | |
| SU1664789A1 (en) | Method for obtaining p-aminobenzoic acid | |
| CN117403262A (en) | Catalytic material for producing hydrogen by water electrolysis and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20220624 |