CN114085229A - Application method of fatty acid in copper phthalocyanine synthesis process - Google Patents
Application method of fatty acid in copper phthalocyanine synthesis process Download PDFInfo
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- CN114085229A CN114085229A CN202111237700.9A CN202111237700A CN114085229A CN 114085229 A CN114085229 A CN 114085229A CN 202111237700 A CN202111237700 A CN 202111237700A CN 114085229 A CN114085229 A CN 114085229A
- Authority
- CN
- China
- Prior art keywords
- copper phthalocyanine
- acid
- percent
- fatty acid
- octadecyl
- 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.)
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- 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 66
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 48
- 239000000194 fatty acid Substances 0.000 title claims abstract description 48
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 48
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 28
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 22
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 49
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 30
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 235000021357 Behenic acid Nutrition 0.000 claims description 6
- 229940116226 behenic acid Drugs 0.000 claims description 6
- KFEVDPWXEVUUMW-UHFFFAOYSA-N docosanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 KFEVDPWXEVUUMW-UHFFFAOYSA-N 0.000 claims description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 4
- 239000011609 ammonium molybdate Substances 0.000 claims description 4
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 claims description 4
- 229940010552 ammonium molybdate Drugs 0.000 claims description 4
- 235000018660 ammonium molybdate Nutrition 0.000 claims description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 4
- 229940045803 cuprous chloride Drugs 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000001256 steam distillation Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000003513 alkali Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000000576 coating method Methods 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
- 238000005516 engineering process Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention discloses an application method of fatty acid in the copper phthalocyanine synthesis process, and particularly relates to the technical field of copper phthalocyanine synthesis, wherein a proper amount of fatty acid is added in the copper phthalocyanine synthesis process, wherein the fatty acid is any one of octadecyl acid, dodecyl acid or docodecyl acid; fatty acids of the general formula: R-COOH; in the formula: r is CnH2n +1(n is 6-22); any one of octadecyl acid, dodecyl acid or docodecyl acid can be added while preparing the copper phthalocyanine, so that the material compatibility can be improved, the reaction can be promoted to be more complete, the product yield is improved by 3-5%, and the unit consumption of raw materials and the discharge of three wastes are correspondingly reduced.
Description
Technical Field
The invention particularly relates to the technical field of copper phthalocyanine synthesis, and particularly relates to an application method of fatty acid in a copper phthalocyanine synthesis process.
Background
The phthalocyanine blue has the characteristics of bright blue, high tinting strength, excellent fastness, light resistance, heat resistance, acid and alkali resistance, organic solvent resistance and the like, and has extremely good stability, and the like, and is widely used in the aspects of coatings, printing ink, paint, rubber, plastics and the like, and in addition, has special application in industries of semiconductors, atomic energy, laser and the like.
In the invention, a proper amount of fatty acid (0.1-10% of the total amount of phthalic anhydride) is added in the copper phthalocyanine synthesis process to improve the compatibility of materials, promote the reaction to be more complete, improve the product yield by 3-5%, and correspondingly reduce the unit consumption of raw materials and the discharge of three wastes.
Disclosure of Invention
The invention aims to provide an application method of fatty acid in a copper phthalocyanine synthesis process, and aims to solve the problems of poor material compatibility, incomplete reaction, low product yield, high raw material unit consumption and high discharge of three wastes in the traditional copper phthalocyanine synthesis process proposed in the background technology.
In order to achieve the purpose, the invention provides the following technical scheme:
an application method of fatty acid in the copper phthalocyanine synthesis process comprises adding appropriate amount of fatty acid in the copper phthalocyanine synthesis process, wherein the fatty acid is any one of octadecyl acid, dodecyl acid or docodecyl acid; fatty acids of the general formula: R-COOH; in the formula: r is CnH2n +1(n is 6-22);
the preparation method of the copper phthalocyanine comprises the following steps: adding 310 g of fatty acid, 310 g of 100 percent phthalic anhydride, 231 g of urea and 1500 ml of solvent alkylbenzene into a 3000 ml three-necked bottle provided with a stirrer, a thermometer and a condenser, stirring and heating for 4 hours, uniformly heating to 170 ℃, and preserving heat for 2 hours; 231 g of urea is added, the temperature is uniformly raised to 190 ℃ in hour time, and the temperature is kept for 2 hours;
then adding 61 g of 100% cuprous chloride and 4 g of 100% ammonium molybdate, uniformly heating to 210 ℃ within 5 hours, preserving heat, stirring, reacting for 6 hours, and cooling to 100 ℃;
50 g of 30% sodium hydroxide solution is added, the solvent alkylbenzene is recovered by steam distillation, no solvent is distilled off after about 5 hours, and the distillation is finished. Filtering, washing and drying.
As a further technical scheme of the invention, when the fatty acid is octadecyl acid, 3 g of octadecyl acid is used for preparing copper phthalocyanine, 305 g of copper phthalocyanine with the content of 92 percent and the yield of 93 percent is obtained.
As a further technical scheme of the invention, when the fatty acid is octadecyl acid, 1 g of octadecyl acid is taken for preparing copper phthalocyanine, the content of the copper phthalocyanine is 300 g, the content of the copper phthalocyanine is 92 percent, and the yield is 91.5 percent.
As a further technical scheme of the invention, when the fatty acid is octadecyl acid, 2 g of octadecyl acid is taken for preparing the copper phthalocyanine, 304 g of the copper phthalocyanine is obtained, the content is 92 percent, and the yield is 92.7 percent.
As a further technical scheme of the invention, when the fatty acid is octadecyl acid, 5 g of octadecyl acid is taken for preparing the copper phthalocyanine, 305 g of the copper phthalocyanine is obtained, the content is 91.5 percent, and the yield is 92.5 percent.
As a further technical scheme of the invention, when the fatty acid is dodecyl acid, 3 g of the dodecyl acid is used for preparing the copper phthalocyanine, 305 g of the copper phthalocyanine is obtained, the content is 92 percent, and the yield is 93 percent.
As a further technical scheme of the invention, when the docosanoic acid is selected as the fatty acid, 3 g of docosanoic acid is used for preparing the copper phthalocyanine, 305 g of the copper phthalocyanine is obtained, the content is 92 percent, and the yield is 93 percent.
Compared with the prior art, the invention has the beneficial effects that:
adding 310 g of 100 percent phthalic anhydride, 231 g of urea and 1500 ml of solvent alkylbenzene into a 3000 ml three-mouth bottle provided with a stirrer, a thermometer and a condenser, uniformly heating to 170 ℃ for 4 hours under stirring, and preserving heat for 2 hours; then 231 g of urea is added, the temperature is uniformly raised to 190 ℃ in hour time, and the temperature is kept for 2 hours; then adding 61 g of 100% cuprous chloride and 4 g of 100% ammonium molybdate, uniformly heating to 210 ℃ within 5 hours, preserving heat, stirring and reacting for 6 hours; when the temperature is reduced to 100 ℃, adding 50 g of 30% sodium hydroxide solution, introducing steam for distillation to recover the solvent alkylbenzene, and after about 5 hours, no solvent is discharged, and the distillation is finished; any one of octadecyl acid, dodecyl acid or docodecyl acid can be added while preparing the copper phthalocyanine, so that the material compatibility can be improved, the reaction can be promoted to be more complete, the product yield is improved by 3-5%, and the unit consumption of raw materials and the discharge of three wastes are correspondingly reduced.
Detailed Description
The technical solutions in the embodiments of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
In the embodiment of the invention, an application method of fatty acid in the copper phthalocyanine synthesis process is characterized in that a proper amount of fatty acid is added in the copper phthalocyanine synthesis process, wherein the fatty acid is any one of octadecyl acid, dodecyl acid or docodecyl acid; fatty acids of the general formula: R-COOH; in the formula: r is CnH2n +1(n is 6-22);
the preparation method of the copper phthalocyanine comprises the following steps: adding 310 g of fatty acid, 310 g of 100 percent phthalic anhydride, 231 g of urea and 1500 ml of solvent alkylbenzene into a 3000 ml three-necked bottle provided with a stirrer, a thermometer and a condenser, stirring and heating for 4 hours, uniformly heating to 170 ℃, and preserving heat for 2 hours; 231 g of urea is added, the temperature is uniformly raised to 190 ℃ in hour time, and the temperature is kept for 2 hours;
then adding 61 g of 100% cuprous chloride and 4 g of 100% ammonium molybdate, uniformly heating to 210 ℃ within 5 hours, preserving heat, stirring, reacting for 6 hours, and cooling to 100 ℃;
50 g of 30% sodium hydroxide solution is added, the solvent alkylbenzene is recovered by steam distillation, no solvent is distilled off after about 5 hours, and the distillation is finished. Filtering, washing and drying.
Example one
When the fatty acid is octadecyl acid, 3 g of octadecyl acid is used for preparing copper phthalocyanine, 305 g of copper phthalocyanine is obtained, the content is 92 percent, and the yield is 93 percent.
Example two
When the fatty acid is octadecyl acid, 1 g of octadecyl acid is used for preparing copper phthalocyanine, the content of the copper phthalocyanine is 300 g, the content of the copper phthalocyanine is 92 percent, and the yield is 91.5 percent.
EXAMPLE III
When the fatty acid is octadecyl acid, 2 g of octadecyl acid is used for preparing copper phthalocyanine, 304 g of copper phthalocyanine with the content of 92 percent and the yield of 92.7 percent is obtained.
Example four
When the fatty acid is octadecyl acid, 5 g of octadecyl acid is used for preparing copper phthalocyanine, 305 g of copper phthalocyanine is obtained, the content is 91.5 percent, and the yield is 92.5 percent.
EXAMPLE five
When the fatty acid is dodecyl acid, 3 g of dodecyl acid is used for preparing copper phthalocyanine, 305 g of copper phthalocyanine with the content of 92 percent and the yield of 93 percent is obtained.
EXAMPLE six
When the docosanoic acid is selected as the fatty acid, 3 g of docosanoic acid is used for preparing the copper phthalocyanine, 305 g of the copper phthalocyanine is obtained, the content is 92 percent, and the yield is 93 percent.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.
Claims (7)
1. An application method of fatty acid in the copper phthalocyanine synthesis process is characterized in that: adding a proper amount of fatty acid in the copper phthalocyanine synthesis process, wherein the fatty acid is any one of octadecyl acid, dodecyl acid or docodecyl acid; fatty acids of the general formula: R-COOH; in the formula: r is CnH2n +1(n is 6-22);
the preparation method of the copper phthalocyanine comprises the following steps: adding 310 g of fatty acid, 310 g of 100 percent phthalic anhydride, 231 g of urea and 1500 ml of solvent alkylbenzene into a 3000 ml three-necked bottle provided with a stirrer, a thermometer and a condenser, stirring and heating for 4 hours, uniformly heating to 170 ℃, and preserving heat for 2 hours; 231 g of urea is added, the temperature is uniformly raised to 190 ℃ in hour time, and the temperature is kept for 2 hours;
then adding 61 g of 100% cuprous chloride and 4 g of 100% ammonium molybdate, uniformly heating to 210 ℃ within 5 hours, preserving heat, stirring, reacting for 6 hours, and cooling to 100 ℃;
50 g of 30% sodium hydroxide solution is added, the solvent alkylbenzene is recovered by steam distillation, no solvent is distilled off after about 5 hours, and the distillation is finished. Filtering, washing and drying.
2. The method of using fatty acids in the synthesis of copper phthalocyanine according to claim 1, wherein: when the fatty acid is octadecyl acid, 3 g of octadecyl acid is used for preparing copper phthalocyanine, 305 g of copper phthalocyanine is obtained, the content is 92 percent, and the yield is 93 percent.
3. The method of using fatty acids in the synthesis of copper phthalocyanine according to claim 1, wherein: when the fatty acid is octadecyl acid, 1 g of octadecyl acid is used for preparing copper phthalocyanine, the content of the copper phthalocyanine is 300 g, the content of the copper phthalocyanine is 92 percent, and the yield is 91.5 percent.
4. The method of using fatty acids in the synthesis of copper phthalocyanine according to claim 1, wherein: when the fatty acid is octadecyl acid, 2 g of octadecyl acid is used for preparing copper phthalocyanine, 304 g of copper phthalocyanine with the content of 92 percent and the yield of 92.7 percent is obtained.
5. The method of using fatty acids in the synthesis of copper phthalocyanine according to claim 1, wherein: when the fatty acid is octadecyl acid, 5 g of octadecyl acid is used for preparing copper phthalocyanine, 305 g of copper phthalocyanine is obtained, the content is 91.5 percent, and the yield is 92.5 percent.
6. The method of using fatty acids in the synthesis of copper phthalocyanine according to claim 1, wherein: when the fatty acid is dodecyl acid, 3 g of dodecyl acid is used for preparing copper phthalocyanine, 305 g of copper phthalocyanine with the content of 92 percent and the yield of 93 percent is obtained.
7. The method of using fatty acids in the synthesis of copper phthalocyanine according to claim 1, wherein: when the docosanoic acid is selected as the fatty acid, 3 g of docosanoic acid is used for preparing the copper phthalocyanine, 305 g of the copper phthalocyanine is obtained, the content is 92 percent, and the yield is 93 percent.
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CN202111237700.9A CN114085229A (en) | 2021-10-22 | 2021-10-22 | Application method of fatty acid in copper phthalocyanine synthesis process |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114181542A (en) * | 2021-11-03 | 2022-03-15 | 双乐颜料泰兴市有限公司 | Application method of alkyl sulfonic acid in copper phthalocyanine synthesis process |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1061609A (en) * | 1990-11-12 | 1992-06-03 | 上海染料化工十二厂 | Solvent method for production of raw copper phthalocyanine |
CN1230573A (en) * | 1998-03-26 | 1999-10-06 | 东洋油墨制造株式会社 | Process for production of metal phthalocyanine |
CN101376109A (en) * | 2008-09-22 | 2009-03-04 | 宣城亚邦化工有限公司 | Sodium-molybdenum series composite catalyst for synthesizing copper phthalocyanine |
WO2009034169A1 (en) * | 2007-09-14 | 2009-03-19 | University College Cork - National University Of Ireland, Cork | Processes for the preparation of the alpha crystal polymorph of metal phthalocyanines |
CN106700597A (en) * | 2016-12-27 | 2017-05-24 | 宣城亚邦化工有限公司 | Production method of copper phthalocyanine |
-
2021
- 2021-10-22 CN CN202111237700.9A patent/CN114085229A/en active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1061609A (en) * | 1990-11-12 | 1992-06-03 | 上海染料化工十二厂 | Solvent method for production of raw copper phthalocyanine |
CN1230573A (en) * | 1998-03-26 | 1999-10-06 | 东洋油墨制造株式会社 | Process for production of metal phthalocyanine |
WO2009034169A1 (en) * | 2007-09-14 | 2009-03-19 | University College Cork - National University Of Ireland, Cork | Processes for the preparation of the alpha crystal polymorph of metal phthalocyanines |
CN101376109A (en) * | 2008-09-22 | 2009-03-04 | 宣城亚邦化工有限公司 | Sodium-molybdenum series composite catalyst for synthesizing copper phthalocyanine |
CN106700597A (en) * | 2016-12-27 | 2017-05-24 | 宣城亚邦化工有限公司 | Production method of copper phthalocyanine |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114181542A (en) * | 2021-11-03 | 2022-03-15 | 双乐颜料泰兴市有限公司 | Application method of alkyl sulfonic acid in copper phthalocyanine synthesis process |
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Application publication date: 20220225 |