CN110563595A - synthetic method of low-toxicity low-harm environment-friendly disperse violet 27 - Google Patents
synthetic method of low-toxicity low-harm environment-friendly disperse violet 27 Download PDFInfo
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- CN110563595A CN110563595A CN201910906419.6A CN201910906419A CN110563595A CN 110563595 A CN110563595 A CN 110563595A CN 201910906419 A CN201910906419 A CN 201910906419A CN 110563595 A CN110563595 A CN 110563595A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
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- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl derivatives
- C09B1/5145—N-aryl derivatives only amino and hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
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Abstract
The invention relates to a synthetic method of low-toxicity low-harm environment-friendly disperse violet 27, which comprises the following steps: (a) adding N-butylimidazole and acetone into a reaction container, and then dropwise adding 2-bromoethanol for reaction to obtain ionic liquid; (b) adding 1, 4-dihydroxy anthraquinone, 1, 4-dihydroxy anthraquinone leuco body and aniline into the ionic liquid, and carrying out condensation reaction to obtain a first mixed solution; (c) and cooling the first mixed solution, carrying out suction filtration to obtain a filter cake and filtrate, washing and soaking the filter cake with hot water to obtain a washing and soaking solution, and carrying out post-treatment on the washed filter cake to obtain disperse violet 27. According to the invention, the synthesized ionic liquid is used as a solvent, and the organic cation of the ionic liquid is selected, so that the condensation reaction is a single condensation reaction, the selectivity is high, the product purity is improved to more than 95%, the yield is more than 94%, meanwhile, the ionic liquid can be recycled, the production cost is reduced, and the pollutant discharge amount is reduced; the disperse violet 27 dye has a delta E of less than 1.0, a delta C of more than 0.5 and a pressure value of less than 0.6.
Description
Technical Field
The invention relates to a synthesis method of a dye, in particular to a synthesis method of low-toxicity low-harm environment-friendly disperse violet 27.
Background
Disperse violet 27, also known as solvent blue 90, disperse blue 72, its chemical name is 1-phenylamino-4-hydroxyanthraquinone, its English name is disperseViolet 27, its molecular formula is C20H13NO3Molecular weight 315.32, CAS number 19286-75-0. The product is purple black powder, is insoluble in water, is soluble in organic solvent such as benzene, chlorobenzene, xylene, DMF, etc., is dark green in concentrated sulfuric acid, and generates olive to red light blue precipitate after dilution. The disperse violet 27 can be used for coloring various resin plastics, such as polyacrylic resin, ABS resin, polystyrene, organic glass, polyester resin, polycarbonate and the like, so as to obtain red light and blue light; has excellent heat resistance, sun resistance and migration resistance, good tinting strength, high transparency and wide application range.
At present, the general process for producing disperse violet 27 is as follows: adding n-butyl alcohol into a condensation kettle through a metering tank, starting stirring, adding aniline, boric acid, 1, 4-dihydroxy anthraquinone and 1, 4-dihydroxy anthraquinone leuco bodies, sealing a cover after adding, opening a condenser to feed in and discharge water, heating by steam in a jacket for about 1 hour, heating to 80-110 ℃, preserving heat for 6 hours under a reflux state, continuously cooling to 40-50 ℃, starting a kettle bottom valve to discharge materials, feeding into a filtration tank, vacuumizing to dry mother liquor, and washing a filter cake to be neutral by hot water at 80-90 ℃; and drying the filter cake in an oven, crushing, mixing and packaging to obtain the disperse violet 27 finished product. The disperse violet 27 product produced by the process has poor quality and poor color and light consistency, the hue delta E is more than 0.5 and accounts for about 60 percent of the total yield, and partial single-batch products can reach qualified quality only by solvent refining, thereby causing resource waste and pollution to the environment; the reaction yield is low, about 84%, and the competitive double condensation and hydrolysis side reactions generated in the reaction process are not easy to control, so that the reaction selectivity is influenced, and further the product yield is influenced.
Disclosure of Invention
the invention aims to overcome the defects of the prior art and provide a method for synthesizing disperse violet 27 with high conversion rate.
In order to achieve the purpose, the invention adopts the technical scheme that: a synthetic method of low-toxicity low-harm environment-friendly disperse violet 27 comprises the following steps:
(a) Adding N-butylimidazole and acetone into a reaction container, slowly dropwise adding 2-bromoethanol under stirring for reaction, and continuously stirring to obtain ionic liquid;
(b) heating the ionic liquid to 40-55 ℃, adding 1, 4-dihydroxyanthraquinone, 1, 4-dihydroxyanthraquinone leuco body and aniline into the ionic liquid, stirring, heating to 80-85 ℃, and carrying out condensation reaction to obtain a first mixed solution;
(c) Cooling the first mixed solution to 40-50 ℃, carrying out suction filtration to obtain a filter cake and filtrate, washing and soaking the filter cake with hot water to obtain a washing and soaking solution, combining the washing and soaking solution and the filtrate, and distilling to obtain a second mixed solution; and carrying out post-treatment on the filter cake obtained by washing to obtain the disperse violet 27.
in the step (a), the feeding mass ratio of the N-butylimidazole to the 2-bromoethanol is 1-1.1: 1.
specifically, in the step (a), the feeding mass ratio of the acetone to the N-butylimidazole is 1.0-1.2: 1.
Specifically, in the step (b), the ratio of the feeding mass of the aniline to the total feeding mass of the 1, 4-dihydroxy anthraquinone and the 1, 4-dihydroxy anthraquinone leuco body is 1: 2.4-2.6.
Specifically, the ratio of the feeding mass of the N-butylimidazole to the total feeding mass of the 1, 4-dihydroxyanthraquinone and the 1, 4-dihydroxyanthraquinone leuco body is 0.4-0.56: 1.
Specifically, in the step (c), the temperature is reduced to 40-45 ℃ for suction filtration.
Specifically, in the step (c), the second mixed solution is heated to 100-110 ℃ for dehydration to obtain a first recovered solution, the first recovered solution is reused as the ionic liquid in the step (a), and the steps (b) and (c) are further performed to obtain the disperse violet 27.
specifically, in the step (c), the temperature of the hot water is 80-90 ℃, and the post-treatment is to wash the filter cake to be neutral by using the hot water at 80-100 ℃ and then dry the filter cake.
In the invention, as the Ionic Liquids (ILs for short) have non-volatility, VOC emission caused by volatilization in the processes of material pumping, filtering and distillation of the traditional organic solvent and solvent loss caused by volatilization can be avoided in the industrial production process; the ionic liquid has good high-temperature stability, the safety of the industrial production process is greatly improved, although the ionic liquid is 2-4 times more expensive than the traditional organic solvent at the present stage, the ionic liquid can be recycled for many times after being heated to 110 ℃ for dehydration, the loss is extremely low, and the overall cost is not obviously increased. The ionic liquid has the advantages of no odor, no pollution, no flammability, easy separation from products, easy recovery, repeated and repeated recycling, convenient use and the like, is an ideal substitute of the traditional volatile solvent, effectively avoids the problems of serious environment, health, safety, equipment corrosion and the like caused by the use of the traditional organic solvent, and is a genuine and environment-friendly green solvent. Is suitable for the cleaning technology advocated at present and the requirement of sustainable development, and has been widely accepted and accepted by people.
The reaction equation of the present invention is as follows:
Due to the application of the technical scheme, compared with the prior art, the invention has the following advantages: the invention relates to a synthesis method of low-toxicity low-harm environment-friendly disperse violet 27, which is characterized in that the synthesized ionic liquid is used as a solvent, and organic cations in the ionic liquid are selected, so that the condensation reaction is a single condensation reaction, the high selectivity is realized, impurities generated by low selectivity due to competitive double condensation and hydrolysis side reactions in the prior art are avoided, the product purity is obviously improved to more than 95%, the yield is more than 94%, in addition, the synthesized ionic liquid can be recycled, the production cost is greatly reduced, the economic benefit is obvious, and the pollutant discharge amount is reduced; the obtained disperse violet 27 dye has delta E of less than 1.0, delta C of more than 0.5 and pressure value of less than 0.6, and the product quality can meet the application requirements of high-end customers.
Drawings
FIG. 1 is a schematic process flow diagram of the present invention.
Detailed Description
The synthetic method of the low-toxicity low-harm environment-friendly disperse violet 27 comprises the following steps:
(a) Adding N-butylimidazole and acetone into a reaction container, slowly dropwise adding 2-bromoethanol under stirring for reaction, and continuously stirring to obtain ionic liquid; the feeding mass ratio of the N-butylimidazole to the 2-bromoethanol is 1-1.1: 1; the feeding mass ratio of the acetone to the N-butylimidazole is 1.0-1.2: 1;
(b) Heating the ionic liquid to 45-55 ℃, adding 1, 4-dihydroxy anthraquinone, 1, 4-dihydroxy anthraquinone leuco body and aniline into the ionic liquid, stirring, heating to 80-85 ℃, and carrying out condensation reaction to obtain a first mixed solution; the ratio of the feeding mass of the aniline to the total feeding mass of the 1, 4-dihydroxy anthraquinone and 1, 4-dihydroxy anthraquinone leuco bodies is 1: 2.4-2.6; the ratio of the feeding mass of the N-butylimidazole to the total feeding mass of the 1, 4-dihydroxyanthraquinone and 1, 4-dihydroxyanthraquinone leuco bodies is 0.4-0.56: 1;
(c) Cooling the first mixed solution to 40-50 ℃, carrying out suction filtration to obtain a filter cake and filtrate, washing and soaking the filter cake with hot water at 80-90 ℃ to obtain a bubble washing solution, combining the bubble washing solution and the filtrate, and distilling to obtain a second mixed solution; and carrying out post-treatment on the washed filter cake (washing the filter cake to be neutral by hot water at the temperature of 80-100 ℃, and then drying the filter cake) to obtain disperse violet 27. And (3) heating the second mixed solution to 100-110 ℃ for dehydration to obtain a first recovery solution, and repeatedly using the first recovery solution as the ionic liquid in the step (a), and then performing the steps (b) and (c) to obtain disperse violet 27.
The invention will be further described with reference to specific examples, but the scope of protection of the invention is not limited thereto:
example 1
the embodiment provides a synthesis method of low-toxicity low-harm environment-friendly disperse violet 27, which comprises the following steps:
(a) Adding 800 kg of N-butylimidazole and 800 kg of acetone into a reaction container, slowly dropwise adding 800 kg of 2-bromoethanol while stirring and cooling for reaction, continuously stirring for 5 hours, and removing the acetone by reduced pressure distillation to obtain ionic liquid;
(b) Heating the ionic liquid to 50 ℃, adding 1200 kg of 1, 4-dihydroxy anthraquinone, 300 kg of 1, 4-dihydroxy anthraquinone leuco body and 580 kg of aniline into the ionic liquid, stirring, heating to 85 ℃, and carrying out condensation reaction to obtain a first mixed solution;
(c) Cooling the first mixed solution to 45 ℃, carrying out suction filtration to obtain a filter cake and filtrate, washing and soaking the filter cake with hot water of 90 ℃ to obtain a washing and soaking solution, combining the washing and soaking solution and the filtrate, and carrying out distillation to obtain a second mixed solution; then, carrying out post-treatment on the filter cake obtained by washing (washing the filter cake to be neutral by hot water at 100 ℃, drying again), drying, crushing and packaging to obtain 1854 kg of disperse violet 27 finished products; the yield thereof was found to be 94.1%. HPLC content 95.23%, Δ E0.872, Δ C0.714 gay, pressure value 0.43.
Example 2
this example provides a method for synthesizing low-toxicity, low-harm and environment-friendly disperse violet 27, which is substantially the same as that in example 1, except that the amount of aniline added in step (b) is 625 kg; finally, 1887 kg of disperse violet 27 finished products are obtained after drying, crushing and packaging; the yield was 95.8%, HPLC content was 95.15%, Δ E0.641, Δ C0.502 was slightly brilliant, and pressure value was 0.59.
example 3
This example provides a method for synthesizing low-toxicity, low-harm and environment-friendly disperse violet 27, which is substantially the same as that in example 1, except that the amount of aniline added in step (b) is 600 kg; finally, the disperse violet 27 finished product 1868 kg is obtained after drying, crushing and packaging; the yield was 94.8%, the HPLC content was 95.12%, Δ E was 0.961, Δ C was 0.519 brilliant, and the pressure value was 0.53.
Example 4
This example provides a method for synthesizing low-toxicity, low-harm and environment-friendly disperse violet 27, which is substantially the same as that in example 1, except that in step (a), 600 kg of N-butylimidazole, 600 kg of bromoethanol and 600 kg of acetone are added; finally, the disperse violet 27 finished product 1867 kg is obtained after drying, crushing and packaging; the yield was 94.7%, HPLC content was 95.07%, Δ E was 0.825, Δ C was 0.517 brilliant, and pressure value was 0.22.
Example 5
this example provides a method for synthesizing low-toxicity, low-harm, and environmentally friendly disperse violet 27, which is substantially the same as that in example 1, except that N-butylimidazole is added in an amount of 840 kg in step (a), bromoethanol is added in an amount of 840 kg, and acetone is added in an amount of 840 kg; finally drying, crushing and packaging to obtain 1852 kg of disperse violet 27 finished products; the yield is 94.0%, the HPLC content is 95.82%, the Delta E is 0.86%, the Delta C is 0.693 and the pressure value is 0.36.
example 6
This example provides a method for synthesizing low-toxicity, low-harm and environment-friendly disperse violet 27, which is substantially the same as that in example 1, except that the amount of bromoethanol added in step (a) is 727 kg, and the amount of acetone added in step (a) is 960 kg; finally, the disperse violet 27 finished product 1864 kg is obtained after drying, crushing and packaging; the yield was 94.6%, the HPLC content was 95.63%, Δ E was 0.89, Δ C was 0.645 brilliant, and the pressure value was 0.34.
Example 7
The embodiment provides a synthesis method of low-toxicity low-harm environment-friendly disperse violet 27, which is basically the same as that in embodiment 1, except that in the step (b), the temperature is raised to 95 ℃ for reaction, and finally 1902 kg of disperse violet 27 finished products are obtained through drying, crushing and packaging; the yield was 96.5%, the HPLC content was 95.16%, Δ E was 0.749, Δ C was 0.507, and the pressure value was 0.31.
Example 8
This example provides a method for synthesizing low-toxicity, low-harm, and environmentally friendly disperse violet 27, which is substantially the same as that in example 1, except that the ionic liquid in step (a) of example 1 does not need to be synthesized, the second mixed solution in example 1 is heated to 105 ℃ for dehydration to obtain a first recovered solution, which is used as the ionic liquid for reuse, and then steps (b) and (c) are performed to obtain 1860 kg of finished disperse violet 27; the yield is 94.4%, the HPLC content is 95.32%, the Delta E is 0.97%, the Delta C is 0.633 and the pressure value is 0.35.
Comparative example 1
The embodiment provides a comparative production method of disperse violet 27 dye, which is carried out by adopting a general process, and specifically comprises the following steps: 2200 kg of n-butanol is added into a condensation kettle through a metering tank, stirring is started, 450 kg of aniline, 100 kg of boric acid, 800 kg of 1, 4-dihydroxy anthraquinone and 180 kg of 1, 4-dihydroxy anthraquinone leuco body are added, a cover is closed after the addition, a condenser is opened to feed water and discharge water, jacket steam is fed to raise the temperature to 80-110 ℃ about 1 hour, the temperature is kept for 8 hours under a reflux state, the temperature is kept to be 40-50 ℃, a kettle bottom valve is started to discharge the materials to enter a suction filtration tank, mother liquor is vacuum-drained, and filter cakes are washed to be neutral by hot water at 80-90 ℃; and drying the filter cake in an oven, crushing, mixing and packaging to obtain 1090 kg of a finished disperse violet 27 product, wherein the yield is 84.6%, the HPLC content is 93.86%, the Delta E is 0.791, the Delta C-0.673 is dark, and the pressure value is 0.44.
Comparative example 2
This comparative example provides a synthesis of a low toxicity, low harm, environmentally friendly disperse Violet 27, which is essentially the same as that of example 1 except that an ionic liquid was usedSubstituting the ionic liquid synthesized in the step (a) to obtain 1540 kg of finished disperse violet 27; the yield was 78.2%, HPLC content was 92.75%, Δ E was 0.521%, Δ C-0.509 was slightly dark, and pressure value was 0.61.
The above embodiments are merely illustrative of the technical ideas and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (8)
1. A synthetic method of low-toxicity low-harm environment-friendly disperse violet 27 is characterized by comprising the following steps:
(a) Adding N-butylimidazole and acetone into a reaction container, slowly dropwise adding 2-bromoethanol under stirring for reaction, reducing pressure to remove excessive bromoethanol and acetone, and continuously stirring to obtain ionic liquid;
(b) Heating the ionic liquid to 40-55 ℃, adding 1, 4-dihydroxyanthraquinone, 1, 4-dihydroxyanthraquinone leuco body and aniline into the ionic liquid, stirring, heating to 80-95 ℃, and carrying out condensation reaction to obtain a first mixed solution;
(c) Cooling the first mixed solution to 40-50 ℃, carrying out suction filtration to obtain a filter cake and filtrate, washing and soaking the filter cake with hot water to obtain a washing and soaking solution, combining the washing and soaking solution and the filtrate, and distilling to obtain a second mixed solution; and carrying out post-treatment on the filter cake obtained by washing to obtain the disperse violet 27.
2. the method for synthesizing the low-toxicity low-harm environment-friendly disperse violet 27 according to claim 1, which is characterized by comprising the following steps: in the step (a), the feeding mass ratio of the N-butylimidazole to the 2-bromoethanol is 1-1.1: 1.
3. the method for synthesizing the low-toxicity low-harm environment-friendly disperse violet 27 according to claim 1, which is characterized by comprising the following steps: in the step (a), the feeding mass ratio of the acetone to the N-butylimidazole is 1.0-1.2: 1.
4. The method for synthesizing the low-toxicity low-harm environment-friendly disperse violet 27 according to claim 1, which is characterized by comprising the following steps: in the step (b), the ratio of the feeding mass of the aniline to the total feeding mass of the 1, 4-dihydroxy anthraquinone and the 1, 4-dihydroxy anthraquinone leuco body is 1: 2.4-2.6.
5. The method for synthesizing the low-toxicity low-harm environment-friendly disperse violet 27 according to claim 1, which is characterized by comprising the following steps: the feeding mass of the N-butylimidazole and the total feeding mass of the 1, 4-dihydroxyanthraquinone and the 1, 4-dihydroxyanthraquinone leuco body are in a ratio of 0.4-0.56: 1.
6. The method for synthesizing the low-toxicity low-harm environment-friendly disperse violet 27 according to claim 1, which is characterized by comprising the following steps: and (c) cooling to 40-45 ℃ and carrying out suction filtration.
7. The method for synthesizing the low-toxicity low-harm environment-friendly disperse violet 27 according to claim 1, which is characterized by comprising the following steps: in the step (c), the second mixed solution is heated to 100-110 ℃ for dehydration to obtain a first recovered solution which is used as the ionic liquid in the step (a) for repeated use, and then the step (b) and the step (c) are carried out to obtain the disperse violet 27.
8. The method for synthesizing the low-toxicity low-harm environment-friendly disperse violet 27 according to claim 1, which is characterized by comprising the following steps: in the step (c), the temperature of the hot water is 80-90 ℃, and the post-treatment is to wash the filter cake to be neutral by using the hot water of 80-100 ℃ and then dry the filter cake.
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