Continuous synthesis method for disperse yellow dye

Abstract

The present invention relates to the technical field of fine organic chemicals, and provides a continuous synthesis method for a disperse yellow dye. Continuous tubular reaction technology is used. A continuous tubular reactor provided by the present invention has a small volume, a large specific surface area, and a large heat transfer area per unit volume. The continuous tubular reactor can promptly transfer reaction heat by means of heat exchange and can ensure safety while accelerating the feeding speed. The continuous tubular reaction provided by the present invention precisely controls a raw material ratio, so that a feeding ratio of main raw materials is close to a theoretical value. In addition, by means of introducing an automatic control system, the chemical reaction can be carried out at a raw material ratio that strictly follows an optimal set value. The mass transfer and heat transfer effect of the continuous reactor is relatively good. Following the improvement to the mass transfer and heat transfer effect, the temperature control is more precise, and the generation of by-products is reduced.

Description

A continuous synthesis method for disperse yellow dye Technical Field

[0001] The invention relates to the technical field of fine organic chemical industry, and in particular to a continuous synthesis method of disperse yellow dye. Background Art

[0002] Disperse yellow dyes are an indispensable class of dyes, and heterocyclic disperse yellow dyes from the pyridone series have become the mainstream disperse yellow dyes on the market due to their high intensity, bright color, and excellent color fastness. Examples include Disperse Yellow 114, Disperse Yellow 119, Disperse Yellow 134, Disperse Yellow 211, and Disperse Yellow 241. Diazotization and coupling reactions are two necessary steps in the preparation of azo dyes. Diazotization involves the reaction of aromatic amines with nitrous acid in an acidic environment to form diazonium salt compounds. After the diazotization reaction is completed, a coupling component is added, and alkali is added in batches to neutralize the acid produced, prompting the reaction to proceed in the forward direction. Traditionally, azo dye production is carried out in batch reactors. To improve production efficiency, batch reactors are tens or even hundreds of cubic meters in volume, with a single stirring paddle in the center. The diazotization process in a batch reactor involves first adding ice to the reactor, then adding the diazo component, the aromatic primary amine, and hydrochloric acid. After stirring, the mixture is cooled to below 5°C, and then sodium nitrite solution is quickly added to initiate the diazotization reaction. Because mass and heat transfer rates are slower than the diazotization reaction, the reaction typically takes several hours to complete. If the diazotization reagent is insufficient in some areas of the reaction system, the resulting diazonium salt can quickly convert to the more stable trans-diazo acid, or the locally generated diazonium salt can easily undergo a coupling reaction with unreacted aromatic primary amines in the system. Both of these side reactions can severely impact subsequent coupling reactions or other reactions, leading to the formation of byproducts and negatively impacting product quality. Furthermore, the diazotization reaction is one of the first 18 hazardous chemical processes subject to key regulatory oversight. The diazotization reaction is highly exothermic, and the diazotization reaction solution is unstable at high temperatures and prone to decomposition and explosion. Therefore, the reaction must be conducted at a lower temperature. Due to its instability, the diazotization reaction solution cannot be stored for extended periods, as prolonged storage can lead to quality degradation. Traditional kettle reactions have a relatively large liquid holding capacity. Once the reaction gets out of control, it will cause very serious consequences. The diazotization reaction is highly exothermic, and safety can only be ensured by slowing down the addition rate during the reaction.

[0003] Chinese patent CN102796394A adopts a multi-stage series-connected kettle continuous coupling process, while Chinese patent CN105348847A adopts a series-connected loop reactor (including a reactor and an external circulation pipeline) continuous coupling process. However, these reactors have poor mass transfer effects and are prone to side reactions, resulting in long reaction times and low production efficiency. Microreactors have good mass and heat transfer effects, and many reports have been published in recent years, such as Chinese patents CN110423489A and CN107488361A. However, these all use coil-type microreactors, which are prone to pipe clogging. In particular, azo disperse dyes are insoluble in water, and solid particles are precipitated during the reaction process, making pipe clogging more likely. Technical issues

[0004] In view of this, the purpose of the present invention is to provide a continuous synthesis method for disperse yellow dye. The method provided by the present invention adopts continuous tubular reaction technology, which can transfer the reaction heat in a timely manner through heat exchange, thereby accelerating the feeding speed while ensuring operational safety and reducing the generation of by-products.

[0005] In order to achieve the above object, the present invention provides the following technical solutions:

[0006] The present invention provides a continuous synthesis method of disperse yellow dye. The continuous synthesis reaction of the disperse yellow dye is carried out in a continuous tubular reaction system. The continuous tubular reaction system comprises: a liquid storage tank, a solid material weighing and feeding system, a liquid material weighing and feeding system, a multi-dispersion disk pipeline mixer, a continuous diazotization tubular reaction system, a continuous coupling tubular reaction system, a diazotization reaction liquid filtering and storage system, a diazotization reaction liquid receiving tank, and a coupling liquid receiving and storage tank.

[0007] The aromatic primary amine and concentrated sulfuric acid are respectively conveyed to a multi-dispersion pipeline mixer in a simultaneously metered manner through a solid material feeding system and a liquid material feeding system, and mixed to obtain a mixed liquid; the aromatic primary amine is fed at a rate of 1000 to 2500 g / min, and the concentrated sulfuric acid is fed at a rate of 4000 to 5500 g / min;

[0008] The mixed solution and nitrosyl sulfuric acid are continuously conveyed to a continuous diazotization tubular reaction system in a simultaneously metered manner to carry out a diazotization reaction to obtain a diazotization reaction solution; the flow rate of the mixed solution is 5000 to 8000 g / min, and the flow rate of the nitrosyl sulfuric acid is 3000 to 5000 g / min,

[0009] The diazotization reaction liquid, the sulfamic acid aqueous solution, the ammonia water, and the alkaline aqueous solution of the pyridone derivative are respectively and continuously conveyed to a continuous coupling tubular reaction system in a simultaneous metering manner for coupling reaction to obtain a coupling reaction liquid; the pyridone derivative is 3-cyano-4-methyl-6-hydroxy-N-methylpyridone or 3-cyano-4-methyl-6-hydroxy-N-ethylpyridone;

[0010] The coupling reaction liquid is sequentially subjected to centrifugal separation, beating, sand milling, standardization and spray drying to obtain disperse yellow dye.

[0011] Preferably, the inner diameter of the reaction section of the pipeline of the polydisperse disk pipeline mixer is 5 to 20 mm, and the length is 1000 to 5000 mm.

[0012] Preferably, the continuous diazotization tubular reaction system comprises a circulating cooling system, a temperature and pressure detection system and a continuous diazotization tubular reactor.

[0013] Preferably, the number of the continuous diazotization tubular reactors is 1 to 10; the inner diameter of the reaction section of the continuous diazotization tubular reactor is 5 to 20 mm, and the length is 1500 mm.

[0014] Preferably, the continuous coupled tubular reaction system comprises a circulating cooling system, a temperature and pressure detection system and a continuous coupled tubular reactor.

[0015] Preferably, the number of the continuous coupled tubular reactors is 2 to 10; the inner diameter of the reaction section of the continuous coupled tubular reactor is 5 to 20 mm, and the length is 1500 mm.

[0016] Preferably, the aromatic primary amine includes p-nitroaniline, m-nitroaniline, o-nitroaniline, o-chloro-p-nitroaniline, o-nitro-p-chloroaniline, 3,4-dichloroaniline, 2,5-dichloroaniline or m-phenylsulfonyloxyaniline.

[0017] Preferably, the temperature of the diazotization reaction is 50-75°C.

[0018] Preferably, the coupling reaction temperature is 10-50°C.

[0019] Preferably, the mass percentage of nitrosyl sulfuric acid in the continuous diazotization tubular reaction system during the diazotization reaction is 10-41%.

[0020] Beneficial Technical Effects: This invention provides a continuous synthesis method for disperse yellow dye, utilizing continuous tubular reaction technology. The continuous tubular reactor provided by this invention features a small volume, large specific surface area, and a large heat transfer area per unit volume. This allows for timely transfer of reaction heat through heat exchange, accelerating feeding while ensuring safety. Reaction operations are remotely transmitted to the control room via a DCS system, eliminating the need for on-site operators, requiring only inspectors, ensuring full safety.

[0021] The continuous tubular reactor provided by the present invention accurately controls the raw material ratio, so that the feeding ratio of the main raw materials is close to the theoretical value, and by introducing an automatic control system, the raw material ratio can be strictly followed by the optimal set value for chemical reaction. The mass transfer and heat transfer effect of the continuous reactor is relatively good. After the mass transfer and heat transfer effect is improved, the temperature control is more accurate, the generation of by-products is reduced, and the amount of COD in the wastewater is greatly reduced. Since the stirring effect of the tubular reactor is much better than that of the traditional kettle reactor, the reaction concentration of the material is increased, the amount of wastewater generated is reduced, and the total amount of wastewater is only 35% of that of the kettle reactor. The continuous equipment is more miniaturized, the unorganized gas is reduced, the amount of waste gas generated is reduced, and the investment in waste gas treatment facilities is also reduced accordingly. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] FIG1 is a schematic diagram of a continuous synthesis method of disperse yellow dye. DETAILED DESCRIPTION

[0023] The present invention provides a continuous synthesis method of disperse yellow dye. The continuous synthesis reaction of the disperse yellow dye is carried out in a continuous tubular reaction system. The continuous tubular reaction system comprises: a liquid storage tank, a solid material weighing and feeding system, a liquid material weighing and feeding system, a multi-dispersion disk pipeline mixer, a continuous diazotization tubular reaction system, a continuous coupling tubular reaction system, a diazotization reaction liquid filtering and storage system, a diazotization reaction liquid receiving tank, and a coupling liquid receiving and storage tank.

[0024] The aromatic primary amine and concentrated sulfuric acid are respectively conveyed to a multi-dispersion pipeline mixer in a simultaneously metered manner through a solid material feeding system and a liquid material feeding system, and mixed to obtain a mixed liquid; the aromatic primary amine is fed at a rate of 1000 to 2500 g / min, and the concentrated sulfuric acid is fed at a rate of 4000 to 5500 g / min;

[0025] The mixed solution and nitrosyl sulfuric acid are continuously conveyed to a continuous diazotization tubular reaction system in a simultaneously metered manner to carry out a diazotization reaction to obtain a diazotization reaction solution; the flow rate of the mixed solution is 5000 to 8000 g / min, and the flow rate of the nitrosyl sulfuric acid is 3000 to 5000 g / min,

[0026] The diazotization reaction liquid, the sulfamic acid aqueous solution, the ammonia water, and the alkaline aqueous solution of the pyridone derivative are respectively and continuously conveyed to a continuous coupling tubular reaction system in a simultaneous metering manner for coupling reaction to obtain a coupling reaction liquid; the pyridone derivative is 3-cyano-4-methyl-6-hydroxy-N-methylpyridone or 3-cyano-4-methyl-6-hydroxy-N-ethylpyridone;

[0027] The coupling reaction liquid is sequentially subjected to centrifugal separation, beating, sand milling, standardization and spray drying to obtain disperse yellow dye.

[0028] The present invention continuously delivers aromatic primary amine and concentrated sulfuric acid to a polydisperse disc pipeline mixer through a solid material feeding system and a liquid material feeding system in a simultaneous metering manner to obtain a mixed liquid.

[0029] In the present invention, the primary aromatic amine preferably includes p-nitroaniline, m-nitroaniline, o-nitroaniline, o-chloro-p-nitroaniline, o-nitro-p-chloroaniline, 3,4-dichloroaniline, 2,5-dichloroaniline, or m-phenylsulfonyloxyaniline; the mass concentration of the concentrated sulfuric acid is preferably 80-98%, more preferably 90-95%; the molar ratio of the primary aromatic amine to HSO in the concentrated sulfuric acid is preferably 1-2.5:4-5.5. The flow rate of the primary aromatic amine is preferably 1000-2500 g / min, more preferably 1500-2000 g / min; the flow rate of the concentrated sulfuric acid is preferably 4000-5500 g / min, more preferably 4500-5000 g / min.

[0030] In the present invention, the inner diameter of the pipeline reaction section of the polydisperse disk pipeline mixer is preferably 5-20 mm, more preferably 10-15 mm; the length of the pipeline reaction section of the polydisperse disk pipeline mixer is preferably 1000-5000 mm, more preferably 1000-2000 mm, and most preferably 1500 mm.

[0031] After obtaining the mixed solution, the mixed solution and nitrosyl sulfuric acid are continuously transported to a continuous diazotization tubular reaction system in a simultaneous metering manner to carry out a diazotization reaction to obtain a diazotization reaction solution.

[0032] In the present invention, the continuous diazotization tubular reaction system includes a circulating cooling system, a temperature and pressure detection system and a continuous diazotization tubular reactor.

[0033] In the present invention, the number of the continuous diazotization tubular reactors is preferably 1 to 10, more preferably 5 to 7; the inner diameter of the pipeline reaction section of the continuous diazotization tubular reactor is preferably 5 to 20 mm, more preferably 10 to 15 mm, and the length of the pipeline reaction section is preferably 1500 mm.

[0034] In the present invention, the molar ratio of nitrosyl sulfuric acid to aromatic primary amine is preferably 1-1.2:1, more preferably 1.01-1.05:1; the mass percentage of nitrosyl sulfuric acid in the continuous diazotization tubular reaction system during the diazotization reaction is preferably 10-41%, more preferably 20-30%; the temperature of the diazotization reaction is preferably 50-75°C, more preferably 55-70°C, and most preferably 60-65°C. The temperature of the diazotization reaction is controlled by a water bath system, and the temperature of the water bath system is preferably 45-55°C.

[0035] The present invention preferably detects whether the raw materials have reacted completely at the reaction endpoint, and the diazotization reaction liquid produced by the reaction enters a diazotization reaction liquid filtration receiving tank.

[0036] The present invention adopts a continuous diazotization tubular reaction system to replace the traditional reactor, so that the raw materials can be added continuously and accurately in proportion, which is a continuous continuous flow reaction.

[0037] After obtaining the diazotization reaction liquid, the present invention continuously transports the diazotization reaction liquid, an aqueous solution of sulfamic acid, aqueous ammonia, and an alkaline aqueous solution of a pyridone derivative to a continuous coupling tubular reaction system in a simultaneous metering manner for a coupling reaction to obtain a coupling reaction liquid; the pyridone derivative is 3-cyano-4-methyl-6-hydroxy-N-methylpyridone or 3-cyano-4-methyl-6-hydroxy-N-ethylpyridone, referred to as methylpyridone or ethylpyridone.

[0038] In the present invention, the continuous coupled tubular reaction system includes a ring cooling system, a temperature and pressure detection system and a continuous coupled tubular reactor; the number of the continuous coupled tubular reactors is preferably 2 to 10, more preferably 5 to 7; the inner diameter of the reaction section of the continuous coupled tubular reactor pipeline is preferably 5 to 20 mm, more preferably 10 to 15 mm; and the length is preferably 1500 mm.

[0039] In the present invention, the mass concentration of the sulfamic acid aqueous solution is preferably 5% to 20%, more preferably 12% to 16%; the mass concentration of the ammonia water is preferably 5% to 30%, more preferably 15% to 25%; the molar ratio of the aromatic primary amine diazonium salt in the diazotization reaction solution, the sulfamic acid in the sulfamic acid aqueous solution, the NH in the ammonia water, and the pyridone derivative in the pyridone derivative alkaline aqueous solution is preferably 1 to 2: 0.01 to 0.1: 1 to 10: 1 to 2.4, more preferably 1: 0.05: 6:

[0040] 1.01; The coupling reaction temperature is preferably 10-50°C, more preferably 20-35°C, and most preferably 25-30°C. The present invention controls the coupling reaction temperature using a water bath system, and the temperature of the water bath system is preferably 0-0°C. The present invention preferably detects whether the raw materials have reacted completely at the reaction endpoint, and the coupling reaction liquid generated after the reaction is complete enters a coupling reaction liquid receiving tank.

[0041] After obtaining the coupling reaction liquid, the method sequentially performs centrifugal separation, beating, sand milling, standardization and spray drying on the coupling reaction liquid to obtain disperse yellow dye.

[0042] In the present invention, the beating is preferably performed by mixing the filter cake obtained after centrifugal separation with a dispersant; the dispersant is preferably MF, lignin or NNO; the amount of the dispersant is preferably 10% to 50% of the mass of the filter cake, more preferably 20 to 30%; the sand grinding is preferably performed using a sand grinder.

[0043] In order to better understand the present invention, the content of the present invention is further illustrated below in conjunction with the examples, but the content of the present invention is not limited to the following examples.

[0044] Example 1

[0045] Continuous production of Disperse Yellow 211

[0046] As shown in Figure 1: The raw materials required for Disperse Yellow 211 are: p-chloro-o-nitroaniline, concentrated sulfuric acid (98wt%), nitrosylsulfuric acid, sulfamic acid aqueous solution (20wt%), ammonia water (25wt%), and ethylpyridone alkaline aqueous solution (15wt%). The molar ratio of p-chloro-o-nitroaniline to HSO in concentrated sulfuric acid, sulfamic acid in sulfamic acid aqueous solution, NH3 in ammonia water, and ethylpyridone in ethylpyridone alkaline aqueous solution is 1:3:1.05:0.05:7:1.01. The raw material aromatic primary amine (p-chloro-o-nitroaniline) required for the diazotization reaction is transported through a solid feeding system, and concentrated sulfuric acid is transported through a liquid feeding system to a polydisperse disc pipeline mixer for thorough mixing. The mixture is then subjected to a diazotization reaction with nitrosylsulfuric acid in a continuous diazotization tubular reaction system. The diazotization reaction temperature is controlled at 55-65° C., and the diazotization reaction is cooled in a 50° C. water bath. The p-chloro-o-nitroaniline and concentrated sulfuric acid are added at a rate of 2500 g / min and 4300 g / min, respectively. The mixture is continuously transported to the polydisperse disc pipeline mixer for mixing in a simultaneous metering manner. The reaction section of the polydisperse disc pipeline mixer has an inner diameter of 10 mm and a length of 1500 mm. The resulting mixed solution and nitrosylsulfuric acid are simultaneously and continuously transported to the continuous diazotization tubular reaction system. The nitrosylsulfuric acid and the mixed solution are added at a rate of 4500 g / min and 6800 g / min, respectively. The number of roots of the continuous diazotization tubular reactor is 5, the inner diameter is 10mm, and the length of the pipeline reaction section is 1500mm. The diazo reaction liquid obtained by the reaction is then transported to the continuous coupling tubular reaction system by the liquid material weighing control system, and the aminosulfonic acid aqueous solution, ammoniacal liquor, and ethylpyridone alkali aqueous solution are also continuously transported to the continuous coupling tubular reaction system in a simultaneously metered manner. During the coupling reaction, the reaction temperature is controlled to be 40-50°C with a 10°C water bath cooling. The number of roots of the continuous coupling tubular reactor is 7, the inner diameter of the reaction section is 10mm, and the length is 1500mm. Finally, the coupling feed liquid is obtained and enters the coupling feed liquid receiving tank. Then centrifugation, beating, sand milling, standardization and spray drying are carried out to obtain disperse yellow 211 dye. The HPLC purity of the product obtained by continuous process is 95-97%, and the product HPLC purity obtained by conventional autoclave production is 90-92%. For every ton of product produced, the continuous process generates 12 tons of wastewater, while the conventional kettle process generates 30 tons of wastewater.

[0047] Example 2

[0048] Continuous production of Disperse Yellow 119

[0049] As shown in Figure 1: The raw materials required for Disperse Yellow 119 are: o-nitroaniline, concentrated sulfuric acid (80wt%), nitrosylsulfuric acid, sulfamic acid aqueous solution (15wt%), ammonia water (15wt%), and ethylpyridone alkaline aqueous solution (15wt%). The molar ratio of p-chloro-o-nitroaniline to HSO in concentrated sulfuric acid, sulfamic acid in sulfamic acid aqueous solution, NH3 in ammonia water, and ethylpyridone in ethylpyridone alkaline aqueous solution is 1:2.9:1.05:0.05:6:1.01. The raw material aromatic primary amine (o-nitroaniline) required for the diazotization reaction is conveyed through a solid feeding system, and concentrated sulfuric acid is conveyed to a polydisperse disc pipeline mixer through a liquid feeding system for thorough mixing. The mixture is then subjected to a diazotization reaction with nitrosyl sulfuric acid in a continuous diazotization tubular reaction system. The diazotization reaction temperature is controlled at 50-60°C, and the diazotization reaction is cooled in a 45°C water bath. The o-nitroaniline and concentrated sulfuric acid are fed at a rate of 1800 g / min and 4630 g / min, and the mixture is continuously conveyed to the polydisperse disc pipeline mixer for mixing in a simultaneous metering manner. The inner diameter of the reaction section of the polydisperse disc pipeline mixer is 12 mm, and the length is 1500 mm. The resulting mixed solution and nitrosyl sulfuric acid are simultaneously and continuously conveyed to the continuous diazotization tubular reaction system. The nitrosyl sulfuric acid and the mixed solution are fed at a rate of 4100 g / min and 6430 g / min, respectively. The number of roots of the continuous diazotization tubular reactor is 6, and the inner diameter is 12mm. The length of the pipeline reaction section is 1500m. The diazo reaction liquid obtained by the reaction is then transported to the continuous coupling tubular reaction system by the liquid material weighing control system. The aminosulfonic acid aqueous solution, ammoniacal liquor, and ethyl pyridone are also continuously transported to the continuous coupling tubular reaction system in a simultaneously metered manner. During the coupling reaction, 5 DEG C of water baths are used to cool the reaction temperature to 35-45 DEG C. The number of roots of the continuous coupling tubular reactor is 6, and the inner diameter of the reaction section is 12mm and the length is 1500mm. Finally, the coupling feed liquid is obtained and enters the coupling feed liquid receiving tank. Then centrifugation, beating, sand milling, standardization and spray drying are carried out to obtain Disperse Yellow 119 dye. The HPLC purity of the product obtained by continuous process is 96-98%, and the product HPLC purity obtained by conventional autoclave production is 92-94%. For every ton of product produced, the continuous process generates 10 tons of wastewater, while the conventional kettle process generates 25 tons of wastewater.

[0050] Example 3

[0051] Continuous production of Disperse Yellow 241

[0052] As shown in Figure 1: The raw materials required for Disperse Yellow 241 are 3,4-dichloroaniline, concentrated sulfuric acid (90wt%), nitrosylsulfuric acid, sulfamic acid aqueous solution (10wt%), ammonia (10wt%), and methylpyridone alkaline aqueous solution (15wt%). The molar ratio of p-chloro-o-nitroaniline to HSO in concentrated sulfuric acid, sulfamic acid in sulfamic acid aqueous solution, NH3 in ammonia, and methylpyridone in methylpyridone alkaline aqueous solution is 1:2.5:1.05:0.05:6:1.01. The raw material aromatic primary amine (3,4-dichloroaniline) required for the diazotization reaction is delivered through a solid feeding system, and concentrated sulfuric acid is delivered to a polydisperse disc pipeline mixer through a liquid feeding system for thorough mixing. The raw material aromatic primary amine (3,4-dichloroaniline) is delivered through a solid feeding system, and concentrated sulfuric acid is delivered to a polydisperse disc pipeline mixer through a liquid feeding system for thorough mixing. The raw material aromatic primary amine is then ... The number of roots of the continuous diazotization tubular reactor is 7, and the inner diameter is 10mm. The length of the pipeline reaction section is 1500m. The diazo reaction liquid obtained by the reaction is then transported to the continuous coupling tubular reaction system by the liquid material weighing control system. The aminosulfonic acid aqueous solution, ammoniacal liquor, and methylpyridone alkali aqueous solution are also continuously transported to the continuous coupling tubular reaction system in a simultaneously metered manner. The coupled reaction is cooled with a 5 DEG C water bath to control the reaction temperature of 30-40 DEG C. The number of roots of the continuous coupling tubular reactor is 7, and the inner diameter of the reaction section is 10mm and the length is 1500mm. Finally, the coupling feed liquid is obtained and enters the coupling feed liquid receiving tank. Centrifugation, beating, sand milling, standardization and spray drying are then carried out to obtain Disperse Yellow 241 dye. The HPLC purity of the product obtained by continuous process is 95-97%, and the product HPLC purity obtained by conventional autoclave production is 92-93%. For every ton of product produced, the continuous process generates 12 tons of wastewater, while the conventional kettle process generates 30 tons of wastewater.

[0053] Example 4

[0054] Continuous production of Disperse Yellow 114

[0055] As shown in Figure 1: The raw materials required for Disperse Yellow 114 are m-phenylsulfonyloxyaniline, concentrated sulfuric acid (98wt%), nitrosylsulfuric acid, sulfamic acid aqueous solution (5wt%), ammonia water (30wt%), and methylpyridone alkaline aqueous solution (15wt%). The molar ratio of p-chloro-o-nitroaniline to HSO in concentrated sulfuric acid, sulfamic acid in sulfamic acid aqueous solution, NH3 in ammonia water, and methylpyridone in methylpyridone alkaline aqueous solution is 1:4.15:1.05:0.05:12:1.01. The raw material aromatic primary amine (m-phenylenesulfonyloxyaniline) required for the diazotization reaction is transported to a polydisperse disc pipeline mixer through a solid feeding system for thorough mixing, and then subjected to a diazotization reaction with nitrosylsulfuric acid in a continuous diazotization tubular reaction system. The diazotization reaction temperature is controlled at 25-35°C, and the diazotization reaction is cooled in a 30°C water bath. The m-phenylenesulfonyloxyaniline is fed at a rate of 2400 g / min, and the concentrated sulfuric acid is fed at a rate of 4000 g / min. The raw materials are continuously transported to the polydisperse disc pipeline mixer for mixing in a simultaneous metering manner. The reaction section of the polydisperse disc pipeline mixer has an inner diameter of 12 mm and a length of 1500 mm. The resulting mixed solution and nitrosylsulfuric acid are simultaneously and continuously fed to the continuous diazotization tubular reaction system. The nitrosylsulfuric acid is fed at a rate of 4450 g / min, and the mixed solution is fed at a rate of 6400 g / min. The number of roots of the continuous diazotization tubular reactor is 5, the inner diameter is 15mm, and the length of the pipeline reaction section is 1500m. The diazo reaction liquid obtained by the reaction is then transported to the continuous coupling tubular reaction system by the liquid material weighing control system, and the aminosulfonic acid aqueous solution, ammoniacal liquor, and methylpyridone alkali aqueous solution are also continuously transported to the continuous coupling tubular reaction system in a simultaneously metered manner. During the coupling reaction, 5 DEG C of water baths are used to cool the reaction temperature to 20-30 DEG C. The number of roots of the continuous coupling tubular reactor is 5, the inner diameter of the reaction section is 15mm, and the length is 1500mm. Finally, the coupling liquid is obtained and enters the coupling liquid receiving tank. Then centrifugation, beating, sand milling, standardization and spray drying are carried out to obtain Disperse Yellow 114 dye. The HPLC purity of the product obtained by continuous process is 94-96%, and the product HPLC purity obtained by conventional autoclave production is 90-92%. For every ton of product produced, 9 tons of wastewater is generated using the continuous process, and 25 tons of wastewater is generated using the conventional kettle process.

[0056] Example 5

[0057] Continuous production of Disperse Yellow 134

[0058] As shown in Figure 1: The raw materials required for Disperse Yellow 134 are: 2,5-dichloroaniline, concentrated sulfuric acid (98wt%), nitrosylsulfuric acid, sulfamic acid aqueous solution (20wt%), ammonia (10wt%), and ethylpyridone alkaline aqueous solution (15wt%). The molar ratio of p-chloro-o-nitroaniline to HSO in concentrated sulfuric acid, sulfamic acid in sulfamic acid aqueous solution, NH3 in ammonia, and ethylpyridone in ethylpyridone alkaline aqueous solution is 1:3.3:1.05:0.05:8:1.01. The raw material aromatic primary amine (2,5-dichloroaniline) required for the diazotization reaction is delivered through a solid feeding system, and concentrated sulfuric acid is delivered to a polydisperse disc pipeline mixer through a liquid feeding system for thorough mixing. The mixture is then subjected to a diazotization reaction with nitrosyl sulfuric acid in a continuous diazotization tubular reaction system. The diazotization reaction temperature is controlled at 60-70°C, and the diazotization reaction is cooled in a 50°C water bath. The 2,5-dichloroaniline and concentrated sulfuric acid are fed at a rate of 2200 g / min and 4480 g / min, and the mixture is continuously delivered to the polydisperse disc pipeline mixer for mixing in a simultaneous metering manner. The inner diameter of the reaction section of the polydisperse disc pipeline mixer is 15 mm and the length is 1500 mm. The resulting mixed solution and nitrosyl sulfuric acid are simultaneously and continuously delivered to the continuous diazotization tubular reaction system. The nitrosyl sulfuric acid and the mixed solution are fed at a rate of 4300 g / min and 6680 g / min, respectively. The number of roots of the continuous diazotization tubular reactor is 7, the inner diameter is 10mm, and the length of the pipeline reaction section is 1500m. The diazo reaction liquid obtained by the reaction is then transported to the continuous coupling tubular reaction system by the liquid material weighing control system. The aminosulfonic acid aqueous solution, ammoniacal liquor, and ethylpyridone alkali aqueous solution are also continuously transported to the continuous coupling tubular reaction system in a simultaneously metered manner. The coupling reaction is cooled in a 5 DEG C water bath to control the reaction temperature to 20-30 DEG C. The number of roots of the continuous coupling tubular reactor is 7, the inner diameter of the reaction section is 15mm, and the length is 1500mm. Finally, the coupling liquid is obtained and enters the coupling liquid receiving tank. It is then centrifuged, beaten, sanded, standardized, and spray-dried to obtain Disperse Yellow 134 dye. The HPLC purity of the product obtained by the continuous process is 95-97%, and the HPLC purity of the product obtained by conventional kettle production is 90-92%. For every ton of product produced, the continuous process generates 10 tons of wastewater, while the conventional kettle process generates 25 tons of wastewater.

[0059] The above is only a preferred embodiment of the present invention. It should be pointed out that for ordinary technicians in this technical field, several improvements and modifications can be made without departing from the principles of the present invention. These improvements and modifications should also be regarded as within the scope of protection of the present invention.

Claims

1. A continuous synthesis method of disperse yellow dye, characterized in that, the continuous synthesis reaction of the disperse yellow dye is carried out in a continuous tubular reaction system; the continuous tubular reaction system includes: a liquid storage tank, a solid material weighing and feeding system, a liquid material weighing and feeding system, a multi-dispersion disk pipeline mixer, a continuous diazotization tubular reaction system, a continuous coupling tubular reaction system, a diazo reaction liquid filtration and storage system, a diazo reaction liquid receiving tank and a coupling material liquid receiving storage tank; the aromatic primary amine and concentrated sulfuric acid are continuously transported to the multi-dispersion disk pipeline mixer for mixing in a simultaneous metering manner through the solid material feeding system and the liquid material feeding system respectively, to obtain a mixed liquid; the feeding rate of the aromatic primary amine is 1000-2500 g / min, and the feeding rate of the concentrated sulfuric acid is 4000-5500 g / min; the mixed liquid and nitrosylsulfuric acid are continuously transported to the continuous diazotization tubular reaction system in a simultaneous metering manner to carry out a diazotization reaction, to obtain a diazo reaction liquid; the flow rate of the mixed liquid is 5000-8000 g / min, and the flow rate of the nitrosylsulfuric acid is 3000-5000 g / min, and the diazo reaction liquid, an aqueous solution of sulfamic acid, ammonia water, and an aqueous solution of the base of the pyridone derivative are continuously transported to the continuous coupling tubular reaction system in a simultaneous metering manner to carry out a coupling reaction, to obtain a coupling reaction liquid; the pyridone derivative is 3-cyano-4-methyl-6-hydroxy-N-methylpyridone or 3-cyano-4-methyl-6-hydroxy-N-ethylpyridone; the coupling reaction liquid is centrifuged, slurried, sanded, standardized and spray-dried in sequence to obtain the disperse yellow dye.

2. The method according to claim 1, characterized in that, the inner diameter of the pipeline reaction section of the multi-dispersion disk pipeline mixer is 5-20 mm, and the length is 1000-5000 mm.

3. The method according to claim 1, characterized in that, the continuous diazotization tubular reaction system includes a circulating cooling system, a temperature and pressure detection system and a continuous diazotization tubular reactor.

4. The method according to claim 3, characterized in that, the number of the continuous diazotization tubular reactors is 1-10; the inner diameter of the reaction section of the continuous diazotization tubular reactor is 5-20 mm, and the length is 1500 mm.

5. The method according to claim 1, characterized in that, the continuous coupling tubular reaction system includes a circulating cooling system, a temperature and pressure detection system and a continuous coupling tubular reactor.

6. The method according to claim 5, characterized in that, the number of the continuous coupling tubular reactors is 2-10; the inner diameter of the reaction section of the continuous coupling tubular reactor is 5-20 mm, and the length is 1500 mm.

7. The method according to claim 1, characterized in that, the aromatic primary amine includes p-nitroaniline, m-nitroaniline, o-nitroaniline, o-chloro-p-nitroaniline, o-nitro-p-chloroaniline, 3,4-dichloroaniline, 2,5-dichloroaniline or m-phenylsulfonyloxyaniline.

8. The method according to claim 1, It is characterized in that the temperature of the diazotization reaction is 50 to 75 °C.

9. The method according to claim 1, It is characterized in that the temperature of the coupling reaction is 10 - 50 °C.

10. The method according to claim 1, It is characterized in that the mass percentage content of nitrosyl sulfuric acid in the continuous diazotization tubular reaction system during the diazotization reaction is 10 to 41%.

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