CN116496636A - Synthesis process of acid yellow - Google Patents
Synthesis process of acid yellow Download PDFInfo
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- CN116496636A CN116496636A CN202310457247.5A CN202310457247A CN116496636A CN 116496636 A CN116496636 A CN 116496636A CN 202310457247 A CN202310457247 A CN 202310457247A CN 116496636 A CN116496636 A CN 116496636A
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- FPVGTPBMTFTMRT-UHFFFAOYSA-L disodium;2-amino-5-[(4-sulfonatophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-UHFFFAOYSA-L 0.000 title claims abstract description 26
- 235000019233 fast yellow AB Nutrition 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 16
- 230000015572 biosynthetic process Effects 0.000 title abstract description 5
- 238000003786 synthesis reaction Methods 0.000 title abstract description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000005859 coupling reaction Methods 0.000 claims abstract description 36
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims abstract description 36
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 34
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000003756 stirring Methods 0.000 claims abstract description 23
- 238000010168 coupling process Methods 0.000 claims abstract description 22
- 239000012954 diazonium Substances 0.000 claims abstract description 22
- 230000008878 coupling Effects 0.000 claims abstract description 21
- 239000007788 liquid Substances 0.000 claims abstract description 19
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 17
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 239000003513 alkali Substances 0.000 claims abstract description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims abstract description 14
- -1 phenethylamino-6-methylpyrimidine Chemical compound 0.000 claims abstract description 14
- 238000010438 heat treatment Methods 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 9
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 9
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 230000001105 regulatory effect Effects 0.000 claims abstract description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 20
- 235000002639 sodium chloride Nutrition 0.000 claims description 19
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 18
- 238000001816 cooling Methods 0.000 claims description 15
- 230000001276 controlling effect Effects 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000011780 sodium chloride Substances 0.000 claims description 9
- 150000001989 diazonium salts Chemical class 0.000 claims description 8
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 6
- 238000010025 steaming Methods 0.000 claims description 4
- 238000000967 suction filtration Methods 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- 239000001103 potassium chloride Substances 0.000 claims description 3
- 235000011164 potassium chloride Nutrition 0.000 claims description 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 3
- 235000011152 sodium sulphate Nutrition 0.000 claims description 3
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims 7
- 238000004043 dyeing Methods 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 7
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 22
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000013078 crystal Substances 0.000 description 6
- 238000004321 preservation Methods 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000012670 alkaline solution Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 241000283070 Equus zebra Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 2
- UEUIKXVPXLWUDU-UHFFFAOYSA-N 4-diazoniobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000009412 basement excavation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical group CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3665—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms
- C09B29/3669—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms from a pyrimidine ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0072—Preparations with anionic dyes or reactive dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis process of acid yellow, which comprises the following steps: s1: diazo reaction: dissolving 2.5-dichloroaniline in hydrochloric acid at a certain ratio, adding emulsifier, adding sodium nitrite solution, and detecting potassium iodide (oxidizing I 2 ) When congo red is blue, sodium nitrite is eliminated by sulfamic acid to obtain diazonium solution; s2: the coupling component is dissolved: mixing 2-dibutylamino-4- (4' -sulfonic acid) phenethylamino-6-methylpyrimidine, an organic solvent and water, regulating pH to 10-11.5 with liquid alkali, stirring until the mixture is fully dissolved, and adding sodium carbonate and ice for later use; s3: adding diazonium solution into the solution for coupling reaction, adjusting pH to 6-6.5 with hydrochloric acid after the reaction is completed, heating up to evaporate butanone, adding salt, stirring at high temperature for 20-40 min, and suction filtering to obtain acid yellow. The invention aims to improve dyeing performance of the dye, improve dyeing fastness, ensure more complete raw material reaction, realize high yield and reduce raw material consumption.
Description
Technical Field
The invention belongs to the field of chemical dye manufacturing, and particularly relates to a synthesis process of acid yellow.
Technical Field
Acid yellow is a dye widely used in the dyeing industry and in the pigment coloring field. The novel heterocyclic azo disperse dye can be dissolved in methanol, methylene dichloride and the like, and the dibutyl amine group is introduced into the coupling component, so that the novel heterocyclic azo disperse dye has the advantages of bright color, large light absorption coefficient, good high-temperature dispersion stability and alkali resistance, excellent fastness and strength performance and the like. The dyeing and printing method is mainly used for dyeing and printing terylene and blended fabrics thereof.
At present, the disclosed preparation method of the acid yellow comprises the following steps of patent application number 202010993593.1, disclosing a C.I. acid yellow 23 dye and a clean production process thereof, coupling by using 2-acetyl-dimethyl succinate and sulfanilic acid diazonium salt, closing a loop, re-coupling with the sulfanilic acid diazonium salt, hydrolyzing, salting out by using mixed salt, separating and recovering the mixed salt, and obtaining the C.I. acid yellow 23 dye. Introducing a biphenylamine compound and an acidic reagent into a reactor, and uniformly stirring and mixing; adding nitrite into a reactor, and stirring and reacting to obtain diazonium salt; preparing an alkaline solution containing 5-pyrazolone, and adding the alkaline solution into a reactor to react with diazonium salt to obtain an azo intermediate I; preparing an alkaline solution of 5-pyrazolone with the same concentration, and adding the alkaline solution into a reactor to react with an azo intermediate I to obtain an azo intermediate II; salting out, filtering and drying to obtain acid yellow N-R powder.
Along with the continuous development and excavation of the application of the acid yellow products, the method has better development prospect, so that the development of a clean production process with low energy consumption, simple operation, safety and environmental protection is urgently needed.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to improve the dyeing property of the dye and the dyeing fastness, the prepared product can meet the application requirement without purification, the production cost is greatly reduced, and the invention is suitable for the requirement of large-scale clean production.
The technical scheme of the invention is summarized as follows:
a process for preparing acid yellow comprising the steps of:
s1: diazo reaction: dissolving 2, 5-dichloroaniline in hydrochloric acid, preserving heat for 1.5-4.5 hours at 40-70 ℃, adding an emulsifying agent, cooling to 25-30 ℃, adding ice for cooling to about 0-5 ℃ within 8-12 minutes, adding sodium nitrite and 2-3 drops of potassium iodide and Congo red solution, slowly heating, preserving heat for 40-80 minutes at 15-20 ℃ by using ice, obtaining diazonium salt when both potassium iodide and Congo red are blue, continuously adding 1-2 mol of ice, and then eliminating residual sodium nitrite by using sulfamic acid to obtain diazonium solution;
s2: the coupling component is dissolved: mixing 2-dibutylamino-4- (4' -sulfonic acid) phenethylamino-6-methylpyrimidine, an organic solvent and water, regulating pH to 10-11.5 with liquid alkali, stirring until the mixture is fully dissolved, and adding sodium carbonate and ice for later use;
s3: coupling reaction: adding diazonium solution into the solution obtained by S2 for coupling reaction, dropwise adding 2-3 drops of resorcinol, stirring for 20-55 minutes, controlling the temperature at 3-10 ℃ by using ice in the middle and later stages, stopping adding ice when the pH value is reduced to 8.5-9, stirring for 5 minutes, continuously adjusting the pH value to be 10-10.5 by using liquid alkali, and continuously coupling, wherein the solution is kept at 3-10 ℃ for 1-3 hours, and then heated to 15-45 ℃ for continuously keeping the temperature for 0.5-1.5 hours until coupling is finished; and slowly adjusting the pH value to 6-6.5 by using hydrochloric acid after reaching the end point, heating to 95-100 ℃ after adjusting, steaming butanone, cooling to 90-95 ℃ slightly, adding salt, stirring at high temperature for 20-40 minutes to obtain a granular product, cooling, and carrying out suction filtration to obtain the acid yellow.
Preferably, the dosage ratio of the 2, 5-dichloroaniline, the hydrochloric acid, the sodium nitrite, the sulfamic acid and the emulsifier in the step S1 is (0.04-0.06) mol, (0.1-0.2) mol, (0.05-0.07) mol, (0.002-0.005) mol, (1-3) g.
Preferably, the ratio of the dosage of the 2, 5-dichloroaniline to the dosage of the hydrochloric acid in the step S1 is 1:3.3.
Preferably, the emulsifier is T-80 or fatty acid methyl ester ethoxylate.
Preferably, the dosage ratio of 2-dibutyl amino-4- (4' -sulfonic acid) phenethyl amino-6-methyl pyrimidine, butanone, liquid alkali and sodium carbonate in the step S2 is (0.04-0.06) mol (1.5-2.5) mol (0.01-0.03) mol (3-5) g.
Preferably, the organic solvent in the step S2 is butanone or acetone.
Preferably, the amount of the organic solvent used in the step S2 is 0.5 to 1.5mol.
Preferably, the salt in the step S3 includes one or more of sodium chloride, potassium chloride and sodium sulfate.
Preferably, the salt is used in an amount of 6 to 12% by volume.
Preferably, the temperature of the cooling and suction filtration in the step S3 is 25-30 ℃.
Preferably, the reaction end point in the step S3 is reached when the interface between resorcinol and the material is not yellow.
The invention has the beneficial effects that:
in the invention, the diazo salt is prepared by diazo reaction of 2.5-dichloroaniline, and the coupling reaction is carried out with 2-dibutylamino-4- (4' -sulfonic acid) phenethylamino-6-methylpyrimidine, so that the produced acid yellow dye has the advantages of sunlight resistance, sublimation, friction resistance and good covering property; the raw materials react more completely, the yield is high, the raw material consumption is reduced, the production cost is saved, the difficult problems of low conventional coupling yield and low production purity are solved, the product can meet the application requirements without purification, the production cost is greatly reduced, and a novel preparation method is provided for the synthesis of the azo dye.
Drawings
FIG. 1 is a flow chart of a process for preparing acid yellow according to the present invention;
Detailed Description
The present invention is described in further detail below with reference to examples to enable those skilled in the art to practice the same by referring to the description.
The preparation method of the acid yellow in the embodiment comprises the following steps:
s1: diazo reaction: dissolving 2, 5-dichloroaniline in hydrochloric acid, preserving heat for 1.5-4.5 hours at 40-70 ℃, adding an emulsifying agent, cooling to 25-30 ℃, adding ice for cooling to about 0-5 ℃ within 8-12 minutes, adding sodium nitrite and 2-3 drops of potassium iodide and Congo red solution, slowly heating, preserving heat for 60 minutes at 15-20 ℃ by using ice, obtaining diazonium salt when the potassium iodide and the Congo red are blue, continuously adding 1-2 mol of ice, and then eliminating residual sodium nitrite by using sulfamic acid to obtain diazonium solution. The dosage ratio of the 2, 5-dichloroaniline, the hydrochloric acid, the sodium nitrite, the sulfamic acid and the emulsifier is (0.04-0.06) mol (0.1-0.2) mol (0.05-0.07) mol (0.002-0.005) mol (1-3) g.
S2: the coupling component is dissolved: mixing 2-dibutylamino-4- (4' -sulfonic acid) phenethylamino-6-methylpyrimidine, an organic solvent and water, regulating pH to 10-11.5 with liquid alkali, stirring until the mixture is fully dissolved, and adding sodium carbonate and ice for later use; the dosage ratio of the 2-dibutylamino-4- (4' -sulfonic acid) phenethylamino-6-methylpyrimidine, butanone, liquid alkali and sodium carbonate is (0.04-0.06) mol, (1.5-2.5) mol, (0.01-0.03) mol, (3-5) g; the organic solvent is butanone or acetone with the mol of 0.5-1.5.
S3: coupling reaction: adding diazonium solution into the solution obtained by S2 for coupling reaction, dropwise adding 2-3 drops of resorcinol, stirring for 20-55 minutes, controlling the temperature at 3-10 ℃ by using ice in the middle and later stages, stopping adding ice when the pH value is reduced to 8.5-9, stirring for 5 minutes, continuously adjusting the pH value to be 10-10.5 by using liquid alkali, and continuously coupling, wherein the solution is kept at 3-10 ℃ for 1-3 hours, and then heated to 15-45 ℃ for continuously keeping the temperature for 0.5-1.5 hours until coupling is finished; and slowly adjusting the pH value to 6-6.5 by using hydrochloric acid after reaching the end point, heating to 95-100 ℃ after adjusting, steaming butanone, cooling to 90-95 ℃ slightly, adding 6-12% by volume of salt, stirring for 20-40 minutes at high temperature, obtaining a granular product, cooling, and carrying out suction filtration to obtain the acid yellow. The salt comprises one or more of sodium chloride, potassium chloride and sodium sulfate.
Example 1
The preparation method of the acid yellow comprises the following steps:
s1: diazo reaction: mixing 20g of hydrochloric acid, 8.1g of zebra 2.5-dichloroaniline and 50g of water, heating to 50 ℃ and preserving heat for 2 hours until no flaky raw materials exist, adding 2g of T-80, cooling to 25-30 ℃, adding 30g of ice to cool to about 0-5 ℃ within 8-12 minutes, adding 3.7g of sodium nitrite, 10g of water and 2-3 drops of potassium iodide and Congo red solution, slowly heating, controlling the temperature at 15-20 ℃ by ice and preserving heat for 60 minutes, obtaining diazonium salt when the potassium iodide and the Congo red both show blue, and continuing adding 20g of ice and then eliminating residual sodium nitrite by using 0.4g of sulfamic acid to obtain diazonium liquid;
s2: the coupling component is dissolved: mixing 21g of zebra-2-dibutyl amino-4- (4' -sulfonic acid) phenethylamino-6-methyl pyrimidine, 70g of butanone and 30g of water, regulating the pH value to be 10-11.5 by using 9g of liquid caustic soda, stirring until the mixture is fully dissolved, and then adding 4g of calcined soda and 90g of ice for later use;
s3: coupling reaction: adding the diazonium solution obtained in the step S1 into the solution obtained in the step S2 for coupling reaction, dropwise adding 2-3 drops of resorcinol, stirring for 40min, controlling the temperature at 5-8 ℃ by using ice in the middle and later stages, stopping adding ice when the pH value is reduced to 8.5-9, stirring for 5 min, continuously adjusting the pH value to 10-10.5 by using liquid alkali for coupling, wherein the solution is subjected to heat preservation at 5-8 ℃ for 2 h, and then is heated to 25-30 ℃ for further heat preservation for 1 h until the coupling is finished; when the joint of resorcinol and the material is not yellow, the pH value is slowly adjusted back to 6-6.5 by hydrochloric acid, the temperature is raised to 95-100 ℃ after the adjustment, butanone is steamed, the temperature is reduced to 90-95 ℃, 35g of sodium chloride is added, the mixture is stirred for 30 minutes at high temperature, the mixture is cooled to 25-30 ℃, 8g of sodium chloride is continuously added without the crystal form to obtain a granular product, 30.02g of yellow crystals is obtained after the temperature is reduced to 25-30 ℃, the yield is 98.1%, the liquid chromatography content is 98.31%, and the application requirement is met without purification.
Example 2
S1: diazo reaction: mixing 21g of hydrochloric acid, 6.5g of zebra 2.5-dichloroaniline and 50g of water, heating to 40 ℃ and preserving heat for 1 hour until no flaky raw materials exist, adding 1.5g of T-80, cooling to 25-30 ℃, adding 30g of ice to cool to about 0-5 ℃ within 8-12 minutes, adding 2.9g of sodium nitrite, 10g of water and 2-3 drops of potassium iodide and Congo red solution, slowly heating, controlling the temperature at 15-20 ℃ by ice and preserving heat for 60 minutes, obtaining diazonium salt when the potassium iodide and the Congo red are blue, continuously adding 20g of ice, and then eliminating residual sodium nitrite by using 0.4g of sulfamic acid to obtain diazonium liquid;
s2: the coupling component is dissolved: 17g of zebra-2-dibutyl amino-4- (4' -sulfonic acid) phenethylamino-6-methyl pyrimidine, 65g of butanone and 30g of water are mixed, pH=10-11.5 is regulated by 7.6g of liquid alkali, and then the mixture is stirred until the mixture is fully dissolved, and then 4g of calcined soda and 90g of ice are added for standby;
s3: coupling reaction: adding the diazonium solution obtained in the step S1 into the solution obtained in the step S2 for coupling reaction, dropwise adding 2-3 drops of resorcinol, stirring for 30min, controlling the temperature at 4-6 ℃ by using ice in the middle and later stages, stopping adding ice when the pH value is reduced to 8.5-9, stirring for 5 min, continuously adjusting the pH value to 10-10.5 by using liquid alkali for coupling, wherein the solution is subjected to heat preservation at 4-6 ℃ for 1 h, then is heated to 15-20 ℃ for further heat preservation for 1 h until the coupling is finished; when the joint of resorcinol and the material is not yellow, the pH value is slowly adjusted back to 6-6.5 by hydrochloric acid, the temperature is raised to 95-100 ℃ after the adjustment, butanone is steamed, the temperature is reduced to 90-95 ℃, 35g of sodium chloride is added, the mixture is stirred for 30 minutes at high temperature, the mixture is cooled to 25-30 ℃, 8g of sodium chloride is continuously added without the crystal form to obtain a granular product, the mixture is cooled to 25-30 ℃ and filtered to obtain 24.98g of yellow crystals, the yield is 97.4%, the liquid chromatography content is 99.24%, and the application requirement is met without purification.
Example 3
S1: diazo reaction: mixing 30g of hydrochloric acid, 9.7g of zebra 2.5-dichloroaniline and 50g of water, heating to 60 ℃ and preserving heat for 3 hours until no flaky raw materials exist, adding 2.5g of T-80, cooling to 25-30 ℃, adding 30g of ice to cool to about 0-5 ℃ within 8-12 minutes, adding 4.2g of sodium nitrite, 10g of water and 2-3 drops of potassium iodide and Congo red solution, slowly heating, controlling the temperature at 15-20 ℃ by ice and preserving heat for 60 minutes, obtaining diazonium salt when the potassium iodide and the Congo red are blue, continuously adding 20g of ice, and then eliminating residual sodium nitrite by using 0.4g of sulfamic acid to obtain diazonium liquid;
s2: the coupling component is dissolved: 25g of zebra-2-dibutyl amino-4- (4' -sulfonic acid) phenethylamino-6-methyl pyrimidine, 75g of butanone and 30g of water are mixed, and are stirred until fully dissolved after the pH value is regulated to be 10-11.5 by 12g of liquid caustic soda, and then 4g of calcined soda and 90g of ice are added for standby;
s3: coupling reaction: adding the diazonium solution obtained in the step S1 into the solution obtained in the step S2 for coupling reaction, dropwise adding 2-3 drops of resorcinol, stirring for 50min, controlling the temperature at 8-10 ℃ by using ice in the middle and later stages, stopping adding ice when the pH value is reduced to 8.5-9, stirring for 5 min, continuously adjusting the pH value to 10-10.5 by using liquid alkali for coupling, wherein the solution is subjected to heat preservation at 8-10 ℃ for 1 h, then is heated to 40-45 ℃ for continuous heat preservation for 1 h until the coupling is finished; when the joint of resorcinol and the material is not yellow, the pH value is slowly adjusted back to 6-6.5 by hydrochloric acid, the temperature is raised to 95-100 ℃ after the adjustment, butanone is steamed, the temperature is reduced to 90-95 ℃, 35g of sodium chloride is added, the mixture is stirred for 30 minutes at high temperature, the mixture is cooled to 25-30 ℃, 8g of sodium chloride is continuously added to the mixture without the crystal form to obtain a granular product, the mixture is cooled to 25-30 ℃ and filtered to obtain 35.38g of yellow crystals, the yield is 95.8%, the liquid chromatography content is 97.32%, and the application requirement is met without purification.
The acid yellow prepared by the method has the advantages of high yield, high product purity, low reaction temperature, energy consumption conservation and the like, and is particularly suitable for industrial production
The above embodiments are provided to illustrate the technical concept and features of the present invention and are intended to enable those skilled in the art to understand the content of the present invention and implement the same, and are not intended to limit the scope of the present invention. All equivalent changes or modifications made in accordance with the spirit of the present invention should be construed to be included in the scope of the present invention.
Claims (9)
1. A method for preparing acid yellow, which is characterized by comprising the following steps:
s1: diazo reaction: dissolving 2, 5-dichloroaniline in hydrochloric acid, preserving heat for 1.5-4.5 hours at 40-70 ℃, adding an emulsifying agent, cooling to 25-30 ℃, adding ice for cooling to about 0-5 ℃ within 8-12 minutes, adding sodium nitrite and 2-3 drops of potassium iodide and Congo red solution, slowly heating, controlling the temperature at 15-20 ℃ by ice, preserving heat for 40-80 minutes to obtain diazonium salt, and removing residual sodium nitrite by sulfamic acid after adding ice to obtain diazonium solution;
s2: the coupling component is dissolved: mixing 2-dibutylamino-4- (4' -sulfonic acid) phenethylamino-6-methylpyrimidine, an organic solvent and water, regulating pH to 10-11.5 with liquid alkali, stirring until the mixture is fully dissolved, and adding sodium carbonate and ice for later use;
s3: coupling reaction: adding diazonium solution into the solution obtained by S2 for coupling reaction, dropwise adding 2-3 drops of resorcinol, stirring for 20-55 minutes, controlling the temperature at 3-10 ℃ by using ice in the middle and later stages, stopping adding ice when the pH value is reduced to 8.5-9, stirring for 5 minutes, continuously adjusting the pH value to be 10-10.5 by using liquid alkali, and continuously reacting, wherein the solution is kept at 3-10 ℃ for 1-3 hours, and then heated to 15-45 ℃ for continuously keeping the temperature for 0.5-1.5 hours until coupling is finished; and slowly adjusting the pH value to 6-6.5 by using hydrochloric acid after reaching the end point, heating to 95-100 ℃ after adjusting, steaming butanone, cooling to 90-95 ℃ after steaming, adding salt, stirring at high temperature for 20-40 minutes to obtain a granular product, and filtering after reducing to a certain temperature to obtain acid yellow.
2. The method for synthesizing acid yellow according to claim 1, wherein the amount ratio of 2, 5-dichloroaniline, hydrochloric acid, sodium nitrite, sulfamic acid and emulsifier in the step S1 is (0.04-0.06) mol, (0.1-0.2) mol, (0.05-0.07) mol, (0.002-0.005) mol, (1-3) g.
3. The method according to claim 1, wherein the emulsifier in the step S1 is T-80 or fatty acid methyl ester ethoxylate.
4. The method for synthesizing acid yellow according to claim 1, wherein the dosage ratio of 2-dibutyl amino-4- (4' -sulfonic acid) phenethyl amino-6-methyl pyrimidine, butanone, liquid caustic soda and sodium carbonate in the step S2 is (0.04-0.06) mol (0.01-0.03) mol (3-5) g.
5. The method for synthesizing acid yellow according to claim 1, wherein the organic solvent in the step S2 is butanone or acetone.
6. The method for synthesizing acid yellow according to claim 5, wherein the amount of the organic solvent is 0.5 to 1.5mol.
7. The method for synthesizing acid yellow according to claim 1, wherein the salt in the step S3 comprises one or more of sodium chloride, potassium chloride and sodium sulfate.
8. The method for synthesizing acid yellow according to claim 7, wherein the salt is used in an amount of 6 to 12% by volume.
9. The method for synthesizing acid yellow according to claim 1, wherein the temperature of the suction filtration after the step S3 is reduced to a certain temperature is 25-30 ℃.
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