CN117865970A - Application of fatty amide compound in copper phthalocyanine synthesis process - Google Patents
Application of fatty amide compound in copper phthalocyanine synthesis process Download PDFInfo
- Publication number
- CN117865970A CN117865970A CN202311849542.1A CN202311849542A CN117865970A CN 117865970 A CN117865970 A CN 117865970A CN 202311849542 A CN202311849542 A CN 202311849542A CN 117865970 A CN117865970 A CN 117865970A
- Authority
- CN
- China
- Prior art keywords
- urea
- fatty amide
- copper phthalocyanine
- hours
- synthesis process
- 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
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 title claims abstract description 34
- -1 fatty amide compound Chemical class 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 25
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 23
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 48
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000004202 carbamide Substances 0.000 claims abstract description 33
- 229940045136 urea Drugs 0.000 claims abstract description 33
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract description 19
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims abstract description 16
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 claims abstract description 16
- 239000011609 ammonium molybdate Substances 0.000 claims abstract description 16
- 229940010552 ammonium molybdate Drugs 0.000 claims abstract description 16
- 235000018660 ammonium molybdate Nutrition 0.000 claims abstract description 16
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims abstract description 16
- 229940045803 cuprous chloride Drugs 0.000 claims abstract description 16
- 229940083608 sodium hydroxide Drugs 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims description 25
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 6
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 238000001256 steam distillation Methods 0.000 claims description 2
- VPNOHCYAOXWMAR-UHFFFAOYSA-N docosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN VPNOHCYAOXWMAR-UHFFFAOYSA-N 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 9
- 239000002699 waste material Substances 0.000 abstract description 5
- 238000003756 stirring Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 3
- ORAWFNKFUWGRJG-UHFFFAOYSA-N Docosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCCC(N)=O ORAWFNKFUWGRJG-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical group 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229910001385 heavy metal Chemical class 0.000 description 1
- 229940116335 lauramide Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention relates to the technical field of copper phthalocyanine synthesis, in particular to application of fatty amide compounds in the copper phthalocyanine synthesis process; the application discloses application of fatty amide compounds in a copper phthalocyanine synthesis process, wherein the fatty amide compounds are reacted with phthalic anhydride, first urea, second urea, cuprous chloride, ammonium molybdate and sodium hydroxide to prepare copper phthalocyanine; the application discloses application of fatty amide compounds in a copper phthalocyanine synthesis process, wherein a proper amount of fatty amide compounds are added as raw materials in the copper phthalocyanine synthesis process, so that the product yield is improved, the raw material consumption is reduced, and the three wastes are reduced.
Description
Technical Field
The invention relates to the technical field of copper phthalocyanine synthesis, in particular to application of fatty amide compounds in the copper phthalocyanine synthesis process.
Background
The phthalocyanine pigment is an aromatic macrocyclic organic compound, the structure of which is similar to that of porphyrin, and the compound forms a conjugated aromatic system with stable eighteen pi electrons. The phthalocyanine does not have any color, and the phthalocyanine is dissolved in a proper auxiliary agent, so that the phthalocyanine and heavy metal salt undergo a complex reaction at a high temperature, and the formed macromolecular complex has a bright color and can be applied to printing and dyeing.
In the related technology, the phthalocyanine is prepared from phthalic anhydride, urea, cuprous chloride, a catalyst and alkylbenzene as raw materials, and can be used as raw materials for producing phthalocyanine blue and other products after refining and purification, the yield of the prepared product is relatively low, and the crude product is usually purified by adopting a high-temperature acid treatment process in the prior art, but the process has the defects of high acid wastewater production amount, high concentration of pollution factors such as CODcr, ammonia nitrogen and copper ions, and the like, and has high environmental protection treatment difficulty and higher recycling difficulty.
Therefore, how to effectively improve the yield of copper phthalocyanine and reduce the discharge of three wastes is a problem to be solved by a plurality of factories.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention aims to provide the application of the fatty amide compound in the copper phthalocyanine synthesis process.
The application provides application of fatty amide compounds in the copper phthalocyanine synthesis process, which adopts the following technical scheme:
the application of fatty amide compounds in the synthesis process of copper phthalocyanine.
Preferably, the synthetic process comprises the following steps: and (3) reacting the fatty amide compound with phthalic anhydride, first urea, second urea, cuprous chloride, ammonium molybdate and sodium hydroxide to prepare the copper phthalocyanine.
Preferably, the synthetic process comprises the following steps:
(1) Mixing fatty amide compounds, phthalic anhydride and a first part of urea, heating to 160-180 ℃ for 4 hours, and reacting for 1-3 hours;
(2) Adding a second part of urea, heating to 180-200 ℃ for 1 hour, and reacting for 1-3 hours;
(3) Adding cuprous chloride and ammonium molybdate, heating to 200-220 ℃ for 5 hours, reacting for 5-7 hours, cooling to 90-110 ℃, adding sodium hydroxide for mixing, distilling, filtering, washing with water, and drying to obtain copper phthalocyanine.
Preferably, the mass ratio of the fatty amide compound to phthalic anhydride to the first urea to the second urea to cuprous chloride to ammonium molybdate to sodium hydroxide is (0.31-31): 310:231:231:61:4:50.
More preferably, the mass ratio of the fatty amide compound to phthalic anhydride to the first urea to the second urea to cuprous chloride to ammonium molybdate to sodium hydroxide is (1-5): 310:231:231:61:4:50.
Preferably, the solvent used is alkylbenzene.
Preferably, the structural formula of the fatty amide compound is shown as formula 1;
wherein: r is R 1 ＝C n H 2n+1 N is selected from natural numbers from 0 to 22;
R 2 ＝C m H 2m+1 m is selected from natural numbers from 0 to 22;
R 3 ＝C z H 2Z+1 the method comprises the steps of carrying out a first treatment on the surface of the z is selected from natural numbers from 0 to 22.
Preferably, the fatty amide compound is at least one of octadecanoamide, dodecanoamide and behenamide.
Preferably, the distillation steps are as follows: the solvent is recovered by steam distillation for 4-6 hours.
In the method, a proper amount (0.1-10% of the total amount of phthalic anhydride) of fatty amide compound is added in the copper phthalocyanine synthesis process to improve the material compatibility, so that the reaction is more complete, the product yield is improved by 3-5%, and the unit consumption of raw materials and the emission of three wastes are correspondingly reduced.
In summary, the present application includes at least one of the following beneficial technical effects:
the application discloses application of fatty amide compounds in a copper phthalocyanine synthesis process, wherein a proper amount of fatty amide compounds are added as raw materials in the copper phthalocyanine synthesis process, so that the product yield is improved, the raw material consumption is reduced, and the three wastes are reduced.
Detailed Description
The raw materials used in the present application are commercially available products, and the present application will be further described in detail with reference to examples and comparative examples.
Example 1:
6 g of octadecanoamide, 620 g of phthalic anhydride (with the purity of 100 percent), 462 g of urea and 3000 ml of solvent alkylbenzene are added into a 5000 ml three-port bottle provided with a stirrer, a thermometer and a condenser, and the temperature is evenly increased to 170 ℃ for 2 hours under stirring; 462 g of urea is added, and the temperature is evenly increased to 190 ℃ for 1 hour and kept for 2 hours; 122 g of cuprous chloride (with the purity of 100%) and 8 g of ammonium molybdate (with the purity of 100%) are added, the temperature is evenly increased to 210 ℃ for 5 hours, the temperature is kept, the stirring and the reaction are carried out for 6 hours, and the temperature is reduced to 100 ℃; adding 100 g of sodium hydroxide solution (the mass concentration is 30%), introducing water vapor, distilling to recover solvent alkylbenzene, and distilling for about 5 hours without solvent; filtering, washing with water and drying; 610 g of copper phthalocyanine is obtained, the content is 92.7%, and the yield is 93%.
Example 2:
2 g of octadecanoamide, 620 g of phthalic anhydride (with the purity of 100 percent), 462 g of urea and 3000 ml of solvent alkylbenzene are added into a 5000 ml three-port bottle provided with a stirrer, a thermometer and a condenser, and the temperature is evenly increased to 170 ℃ for 2 hours under stirring; 462 g of urea is added, and the temperature is evenly increased to 190 ℃ for 1 hour and kept for 2 hours; 122 g of copper (with the purity of 100%) and 8 g of ammonium molybdate (with the purity of 100%) are added, the temperature is evenly increased to 210 ℃ for 5 hours, the temperature is kept, the stirring and the reaction are carried out for 6 hours, and the temperature is reduced to 100 ℃; adding 100 g of sodium hydroxide solution (the mass concentration is 30%), introducing water vapor, distilling to recover solvent alkylbenzene, and distilling for about 5 hours without solvent; filtering, washing and drying to obtain 600 g of copper phthalocyanine with 92.2 percent of content and 91.5 percent of yield.
Example 3:
4 g of octadecanoamide, 620 g of phthalic anhydride (with the purity of 100 percent), 462 g of urea and 3000 ml of solvent alkylbenzene are added into a 5000 ml three-port bottle provided with a stirrer, a thermometer and a condenser, and the temperature is evenly increased to 170 ℃ for 2 hours under stirring; 462 g of urea is added, and the temperature is evenly increased to 190 ℃ for 1 hour and kept for 2 hours; 122 g of cuprous chloride (with the purity of 100%) and 8 g of ammonium molybdate (with the purity of 100%) are added, the temperature is evenly increased to 210 ℃ for 5 hours, the temperature is kept, the stirring and the reaction are carried out for 6 hours, and the temperature is reduced to 100 ℃; adding 100 g of sodium hydroxide solution (the mass concentration is 30%), introducing water vapor, distilling to recover solvent alkylbenzene, and distilling for about 5 hours without solvent; filtering, washing and drying to obtain 608 g of copper phthalocyanine with 92% of content and 92.3% of yield.
Example 4:
10 g of octadecanoamide, 620 g of phthalic anhydride (with the purity of 100 percent), 462 g of urea and 3000 ml of solvent alkylbenzene are added into a 5000 ml three-port bottle provided with a stirrer, a thermometer and a condenser, and the temperature is evenly increased to 170 ℃ for 2 hours under stirring; 462 g of urea is added, and the temperature is evenly increased to 190 ℃ for 1 hour and kept for 2 hours; 122 g of cuprous chloride (with the purity of 100%) and 8 g of ammonium molybdate (with the purity of 100%) are added, the temperature is evenly increased to 210 ℃ for 5 hours, the temperature is kept, the stirring and the reaction are carried out for 6 hours, and the temperature is reduced to 100 ℃; adding 100 g of sodium hydroxide solution (the mass concentration is 30%), introducing water vapor, distilling to recover solvent alkylbenzene, and distilling for about 5 hours without solvent; filtering, washing with water and drying; 610 g of copper phthalocyanine is obtained, the content is 91.7%, and the yield is 92.5%.
Example 5:
6 g of lauramide, 620 g of phthalic anhydride (with the purity of 100%), 462 g of urea and 3000 ml of solvent alkylbenzene are added into a 5000 ml three-port bottle provided with a stirrer, a thermometer and a condenser, and the temperature is uniformly raised to 170 ℃ for 2 hours under stirring; 462 g of urea is added, and the temperature is evenly increased to 190 ℃ in an hour and kept for 2 hours; 122 g of cuprous chloride (with the purity of 100%) and 8 g of ammonium molybdate (with the purity of 100%) are added, the temperature is evenly increased to 210 ℃ for 5 hours, the temperature is kept, the stirring and the reaction are carried out for 6 hours, and the temperature is reduced to 100 ℃; adding 100 g of sodium hydroxide solution (the mass concentration is 30%), introducing water vapor, distilling to recover solvent alkylbenzene, and distilling for about 5 hours without solvent; filtering, washing with water and drying; 610 g of copper phthalocyanine is obtained, the content is 91.5%, and the yield is 92.9%.
Example 6:
6 g of behenyl amide, 620 g of phthalic anhydride (with the purity of 100 percent), 462 g of urea and 3000 ml of solvent alkylbenzene are added into a 5000 ml three-port bottle provided with a stirrer, a thermometer and a condenser, and the temperature is evenly increased to 170 ℃ for 2 hours under stirring; 462 g of urea is added, and the temperature is evenly increased to 190 ℃ in an hour and kept for 2 hours; 122 g of cuprous chloride (with the purity of 100%) and 8 g of ammonium molybdate (with the purity of 100%) are added, the temperature is evenly increased to 210 ℃ for 5 hours, the temperature is kept, the stirring and the reaction are carried out for 6 hours, and the temperature is reduced to 100 ℃; adding 100 g of sodium hydroxide solution (the mass concentration is 30%), introducing water vapor, distilling to recover solvent alkylbenzene, and distilling for about 5 hours without solvent; filtering, washing with water and drying; 610 g of copper phthalocyanine is obtained, the content is 91.6%, and the yield is 92.7%.
Example 7:
in order to verify the effect of the addition amount of the different fatty amide compounds on the synthesis effect of copper phthalocyanine, the addition amount of the octadecanoamide in example 1 was adjusted, and the effect of the addition amount of the different fatty amide compounds on the synthesis effect of copper phthalocyanine was shown in table 1, with the other components and the reaction conditions unchanged.
TABLE 1 influence of the addition amount of stearamide on the Synthesis effect of copper phthalocyanine
In the method, a proper amount (0.1-10% of the total amount of phthalic anhydride) of fatty amide compound is added in the copper phthalocyanine synthesis process to improve the material compatibility, so that the reaction is promoted to be more complete.
Comparative example 1:
620 g of phthalic anhydride (with the purity of 100%), 462 g of urea and 3000 ml of solvent alkylbenzene are added into a 5000 ml three-port bottle provided with a stirrer, a thermometer and a condenser, and the temperature is evenly raised to 170 ℃ for 2 hours under stirring; 462 g of urea is added, and the temperature is evenly increased to 190 ℃ for 1 hour and kept for 2 hours; 122 g of cuprous chloride (with the purity of 100%) and 8 g of ammonium molybdate (with the purity of 100%) are added, the temperature is evenly increased to 210 ℃ for 5 hours, the temperature is kept, the stirring and the reaction are carried out for 6 hours, and the temperature is reduced to 100 ℃; adding 100 g of sodium hydroxide solution (the mass concentration is 30%), introducing water vapor, distilling to recover solvent alkylbenzene, and distilling for about 5 hours without solvent; filtering, washing with water and drying; 590 g of copper phthalocyanine is obtained, the content is 90% and the yield is 88%.
By combining examples 1-7 and comparative example 1, the addition of a proper amount of fatty amide compounds in the synthesis of copper phthalocyanine has obvious effect of improving the product yield by 3-5%, and correspondingly reduces the unit consumption of raw materials and the emission of three wastes.
The present embodiment is merely illustrative of the present application and is not intended to be limiting, and those skilled in the art, after having read the present specification, may make modifications to the present embodiment without creative contribution as required, but is protected by patent laws within the scope of the claims of the present application.
Claims (9)
1. The application of fatty amide compounds in the synthesis process of copper phthalocyanine.
2. The use according to claim 1, characterized in that the synthesis process comprises the following steps: and (3) reacting the fatty amide compound with phthalic anhydride, first urea, second urea, cuprous chloride, ammonium molybdate and sodium hydroxide to prepare the copper phthalocyanine.
3. The use according to claim 1, characterized in that the synthesis process comprises the following steps:
(1) Mixing fatty amide compounds, phthalic anhydride and a first part of urea, heating to 160-180 ℃ for 4 hours, and reacting for 1-3 hours;
(2) Adding a second part of urea, heating to 180-200 ℃ for 1 hour, and reacting for 1-3 hours;
(3) Adding cuprous chloride and ammonium molybdate, heating to 200-220 ℃ for 5 hours, reacting for 5-7 hours, cooling to 90-110 ℃, adding sodium hydroxide for mixing, distilling, filtering, washing with water, and drying to obtain copper phthalocyanine.
4. A use according to claim 3, characterized in that: the mass ratio of the fatty amide compound to the phthalic anhydride to the first part of urea to the second part of urea to the cuprous chloride to the ammonium molybdate to the sodium hydroxide is (0.31-31) 310:231:231:61:4:50.
5. The use according to claim 4, characterized in that: the mass ratio of the fatty amide compound to the phthalic anhydride to the first part of urea to the second part of urea to the cuprous chloride to the ammonium molybdate to the sodium hydroxide is (1-5) 310:231:231:61:4:50.
6. Use according to claim 3, characterized in that the solvent used is alkylbenzene.
7. The use according to any one of claims 1 to 5, wherein the fatty amide compound has a structural formula shown in formula 1;
wherein: r is R 1 ＝C n H 2n+1 N is selected from natural numbers from 0 to 22;
R 2 ＝C m H 2m+1 m is selected from natural numbers from 0 to 22;
R 3 ＝C z H 2Z+1 the method comprises the steps of carrying out a first treatment on the surface of the z is selected from natural numbers from 0 to 22.
8. The use according to claim 7, characterized in that: the fatty amide compound is at least one of octadecyl amide, dodecyl amide and docosyl amide.
9. Use according to claim 3, characterized in that the step of distillation is as follows: the solvent is recovered by steam distillation for 4-6 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311849542.1A CN117865970A (en) | 2023-12-29 | 2023-12-29 | Application of fatty amide compound in copper phthalocyanine synthesis process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311849542.1A CN117865970A (en) | 2023-12-29 | 2023-12-29 | Application of fatty amide compound in copper phthalocyanine synthesis process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117865970A true CN117865970A (en) | 2024-04-12 |
Family
ID=90580366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202311849542.1A Pending CN117865970A (en) | 2023-12-29 | 2023-12-29 | Application of fatty amide compound in copper phthalocyanine synthesis process |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117865970A (en) |
-
2023
- 2023-12-29 CN CN202311849542.1A patent/CN117865970A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111763174A (en) | Method for reducing distillation residues of 5-acetoacetylaminobenzimidazolone mother liquor | |
| CN117865970A (en) | Application of fatty amide compound in copper phthalocyanine synthesis process | |
| US20030008770A1 (en) | Encapsulated oxo-bridged organometallic cluster catalyst and a process for the preparation thereof | |
| CN111362806B (en) | Co-production method of 3-nitro-2-methylbenzoic acid and 3-nitrophthalic acid | |
| CN104030927A (en) | Method for preparing 1-nitroanthraquinone by using metal-modified molecular sieve as catalyst | |
| CN108276261B (en) | Method for preparing 2-bromofluorenone by catalyzing molecular oxygen oxidation in aqueous phase | |
| CN115746006A (en) | Application of alcohol compound in copper phthalocyanine synthesis process | |
| CN117865971A (en) | Application of phosphate compound in copper phthalocyanine synthesis process | |
| CN114085229A (en) | Application method of fatty acid in copper phthalocyanine synthesis process | |
| CN117946124A (en) | Application of fatty sulfonamide compound in copper phthalocyanine synthesis process | |
| CN114181219A (en) | Application method of alkyl polyoxyethylene ether in copper phthalocyanine synthesis process | |
| CN111187240B (en) | Preparation method of 4, 4-diphenyl ether dianhydride | |
| KR910003006B1 (en) | Process for the preparation of maleimide | |
| CN111253272B (en) | Method for preparing benzamide compound | |
| CN110642707B (en) | Purification production method of low-cost environment-friendly sodium salicylate | |
| CN107556188B (en) | Method for synthesizing benzyl ester by phase transfer catalysis | |
| CN113999120A (en) | Preparation method of halogenated aniline compound | |
| CN104496794B (en) | A kind of naphthalene method phthalic anhydride wastewater reclaims the pre-treating method of fumaric acid | |
| CN102108043B (en) | Synthesis method of 1,3,5,7-tetrahydroxyadamantane | |
| CN109734645B (en) | Synthetic process of isatin | |
| CN1974577A (en) | Process of synthesizing copper phthalocyanine in ionic liquid | |
| CN1111158C (en) | Process for preparing crystal violet lactone | |
| CN111592478B (en) | Method for reducing chroma of pentaerythritol ester | |
| CN113603621B (en) | Preparation method of mercaptopropionate series compounds | |
| CN103787529B (en) | Method for treating DCC (N,N'-dicyclohexylcarbodiimide) oxidation wastewater |
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 |