CN102618061B - Preparation method for 2-[N-(2-cyanoethyl)-4-[(2,6-dichloro-4-nitrobenzophenone)azo]anilino]ethyl acetate - Google Patents
Preparation method for 2-[N-(2-cyanoethyl)-4-[(2,6-dichloro-4-nitrobenzophenone)azo]anilino]ethyl acetate Download PDFInfo
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Abstract
The invention relates to a preparation method for disperse orange 30. The preparation method comprises the following steps of: (1) undergoing a diazotization reaction: undergoing a diazotization reaction on 2,6-dichloroparanitroaniline and nitrosyl sulfuric acid in a sulfuric acid medium to obtain a diazonium product solution; and (2) undergoing a coupling reaction: undergoing a coupling reactionon the diazonium product solution obtained in the step (1) and N-cyanoethyl-N-acetoxyethyl to generate disperse orange 30. Particularly, the chromatograph content of 2,6-dichloro paranitroaniline serving as a raw material used in the step (1) is over 99.8 percent by weight, the content of polychlorinated biphenyl amine is lower than 5 ppm, and the diazotization reaction is undergone at the temperature of 0-5 DEG C in the step (1). A product prepared with the method does not contain any international forbidden byproduct, i.e., polychlorinated biphenyl amine, and a basis is laid for the development of the international market; and moreover, the product prepared with method has high yield, high purity and gorgeous chromatic light.
Description
Technical field
The present invention relates to a kind of preparation method of DISPERSE ORANGE 30 200 30.
Background technology
DISPERSE ORANGE 30 200 30, chemistry 2-[N-(2-cyanoethyl) by name-4-[(2,6-bis-chloro-4 nitrophenyls) azo] anilino] ethyl acetate, structural formula is as follows:
DISPERSE ORANGE 30 200 is the mass-tone in the high temperature modification dispersed dye, and its Exposure to Sunlight and sublimation fastness are good, are mainly used in polyester-cotton blend, the direct printing of the dyeing of polyester-viscose blended fabric and cotton-polyester blend cloth.The main production method of DISPERSE ORANGE 30 200 30 is that 6-dichloro p-Nitroaniline is raw material with 2 of technical grade at present, drips nitrosyl sulfuric acid and carry out diazotization reaction in sulfuric acid medium, and then make with coupling component N-cyanoethyl-N-acetyl oxygen ethyl coupling.Due at present domestic technical grade 2.6-bis--chlorine p-nitrophenyl amine content all in 95% left and right, and the world of containing 4.5% left and right forbidding by product polychlorobiphenyl amine.Therefore DISPERSE ORANGE 30 200 30 coloured light of producing by this method are partially dark, and intensity is low, and especially weak point is to contain polychlorobiphenyl amine in product, has hindered product and has marched to world market.
Summary of the invention
Technical problem to be solved by this invention is to overcome the deficiencies in the prior art, and a kind of preparation method of improved DISPERSE ORANGE 30 200 30 is provided.
For solving above technical problem, the present invention takes following technical scheme:
A kind of preparation method of DISPERSE ORANGE 30 200 30 comprises (1), diazotization reaction: make 2,6-dichloro p-Nitroaniline carry out diazotization reaction with nitrosyl sulfuric acid in sulfuric acid medium and obtain diazonium product solution; (2) coupled reaction: make step (1) gained diazonium product solution and N-cyanoethyl-N-acetyl oxygen ethyl generation coupled reaction generate described DISPERSE ORANGE 30 200 30, particularly, in step (1), as raw material, use 2, the chromatogram content of 6-dichloro p-Nitroaniline is more than 99.8wt%, and polychlorobiphenyl amine content wherein is lower than 5ppm; In step (1), described diazotization reaction is carried out at 0～5 ℃ of temperature.
Preferably, step (1) use 2,6-dichloro p-Nitroaniline is by technical grade 2,6-dichloro p-Nitroaniline obtains through refining, described treating process is as follows: by technical grade 2,6-dichloro p-Nitroaniline joins in the mixed system be comprised of water, ethylene glycol monomethyl ether and Dispersant MF, fully stirs, and is heated to 75 ℃～85 ℃, filter, drain, and then with the hot wash of 75 ℃～85 ℃ 2～3 times, filter cake is dried and be get final product.In treating process, technical grade 2, the weight proportion of 6-dichloro p-Nitroaniline, water, ethylene glycol monomethyl ether and Dispersant MF is 300: 400～600: 5～15: 1.
According to a concrete aspect of the present invention, step (1) detailed process is: will make with extra care 2,6-dichloro p-Nitroaniline adds in reactor, the sulfuric acid that adds 98wt%, cool to 0～5 ℃, then drip nitrosyl sulfuric acid and make to occur diazotization reaction, reaction finishes and obtains diazonium product solution.
Preferably, the coupled reaction of step (2) is carried out under the existence of catalyzer, and described catalyzer can be paregal O, dispersion agent NNO or the combination of the two, the consumption of catalyzer is N-cyanoethyl-N-acetyl oxygen ethyl 0.8%～1.2% of quality that feeds intake, for example 1%.
The preferred temperature of the coupled reaction of step (2) is 0 ℃～10 ℃.
According to another concrete aspect of the present invention, the detailed process of step (2) is: add water in reactor, control 0 ℃～10 ℃ of temperature, then add catalyzer, finally drip step (1) the gained diazonium product solution that cools to-5～0 ℃, open the valve of N-cyanoethyl-N-acetyl oxygen ethylaniline simultaneously, N-cyanoethyl-N-acetyl oxygen ethylaniline and diazonium product are carried out and flow coupled reaction, after coupling, material is continued to stir 1.5～2.5 hours, then enter sheet frame, binder, then with cold water washing, arrive neutral, dry up, obtain DISPERSE ORANGE 30 200 30 products.
Due to the enforcement that adopts above technical scheme, the present invention compared with prior art has following advantage:
(1) the international forbidding of the inventive method products obtained therefrom Zhong Buhan by product polychlorobiphenyl amine, in order to explore world market, allusion quotation has been determined basis;
(2), the yield of product is high, purity is high, coloured light is gorgeous.
Embodiment
Embodiment 1
Preparation method according to the DISPERSE ORANGE 30 200 30 of the present embodiment comprises the steps:
(1), 2,6-dichloro p-Nitroaniline refining: add water 500 grams in the 1000ml beaker of whipping appts is housed, water-soluble solvent ethylene glycol monomethyl ether 10 grams, Dispersant MF 1 gram, fully stir evenly.Then add commercially available technical grade 2,6-dichloro p-Nitroaniline 300 grams, fully stir and be warmed up to 80 ℃, filtered while hot, drain, and then with the hot wash of 80 ℃ 2～3 times, filter cake is for refining 2,6-dichloro p-Nitroaniline, and its chromatogram content is more than 99.8wt%, polychlorobiphenyl amine content wherein is lower than 5ppm, and filter cake is dried to obtain 195 grams.
(2), diazotization reaction: get above-mentioned refiningly 2,6-dichloro p-Nitroaniline 195 grams, add 98% sulfuric acid 300 grams, cools to 0～5 ℃ and then drip nitrosyl sulfuric acid and make to occur diazotization reaction and obtain diazonium product solution.
(3), coupled reaction: the ice and the water that add some amount in the beaker of 2000 milliliters, then add 1 gram paregal O, then the above-mentioned diazonium product solution that cools to-5～0 ℃ is added drop-wise in beaker, open the valve of coupling component N-cyanoethyl-N-acetyl oxygen ethylaniline simultaneously, make coupling component and diazonium product carry out and flow coupled reaction, after coupling, material is continued to stir 2 hours, then carrying out suction filtration drains, arrive neutrality with cold water washing again, dry up, obtain the finished product.After measured, in products obtained therefrom, DISPERSE ORANGE 30 200 30 chromatogram content are 99.6%, and polychlorobiphenyl amine content wherein is lower than 5ppm; Product yield 98%; The intensity of the former dyestuff of product is 380%, and coloured light is gorgeous.
Embodiment 2
Preparation method according to the DISPERSE ORANGE 30 200 30 of the present embodiment comprises the steps:
(1), 2,6-dichloro p-Nitroaniline refining: add water 500 grams in the 1000ml beaker of whipping appts is housed, water-soluble solvent ethylene glycol monomethyl ether 10 grams, Dispersant MF 1 gram, fully stir evenly.Then add commercially available 2,6-dichloro p-Nitroaniline 300 grams, fully stir and be warmed up to 80 ℃, filtered while hot, drain, and then with the hot wash of 80 ℃ 2～3 times, filter cake is for refining 2,6-dichloro p-Nitroaniline, and its chromatogram content is more than 99.8wt%, polychlorobiphenyl amine content wherein is lower than 5ppm, and filter cake is dried to obtain 195 grams.
(2), diazotization reaction: get above-mentioned refiningly 2,6-dichloro p-Nitroaniline 195 grams, add 98% sulfuric acid 300 grams, cools to 0～5 ℃ and then drip nitrosyl sulfuric acid and make to occur diazotization reaction and obtain diazonium product solution.
(3), coupled reaction: the ice and the water that add some amount in the beaker of 2000 milliliters, then add 1 gram dispersion agent NNO, then the above-mentioned diazonium product solution that cools to-5～0 ℃ is added drop-wise in beaker, open the valve of coupling component N-cyanoethyl-N-acetyl oxygen ethylaniline simultaneously, coupling component and diazonium product are carried out and flow coupled reaction, after coupling, material is continued to stir 2 hours, then carrying out suction filtration drains, with cold water washing, arrive again neutral, dry up, obtain the finished product.After measured, in products obtained therefrom, DISPERSE ORANGE 30 200 30 chromatogram content are 99.0%, and polychlorobiphenyl amine content wherein is lower than 5ppm; Product yield 98%; The intensity of the former dyestuff of product is 375%, and coloured light is gorgeous.
Embodiment 3
Preparation method according to the DISPERSE ORANGE 30 200 30 of the present embodiment comprises the steps:
(1), 2,6-dichloro p-Nitroaniline refining: add water 500 grams in the 1000ml beaker of whipping appts is housed, water-soluble solvent ethylene glycol monomethyl ether 10 grams, Dispersant MF 1 gram, fully stir evenly.Then add commercially availablely 2,6-dichloro p-Nitroaniline 300 grams, fully stir and be warmed up to 80 ℃, filtered while hot, drain, and then with the hot wash of 80 ℃ 2～3 times, filter cake is refining 2,6-dichloro p-Nitroaniline, its chromatogram content is more than 99.8wt%, filter cake is dried to obtain 195 grams.
(2), diazotization reaction: get above-mentioned refiningly 2,6-dichloro p-Nitroaniline 195 grams, add 98% sulfuric acid 300 grams, cools to 0～5 ℃ and then drip nitrosyl sulfuric acid and make to occur diazotization reaction and obtain diazonium product solution.
(3), coupled reaction: the ice and the water that add some amount in the beaker of 2000 milliliters, then add 0.5 gram dispersion agent NNO and 0.5 gram paregal O, then the above-mentioned diazonium product solution that cools to-5～0 ℃ is added drop-wise in beaker, open the valve of coupling component N-cyanoethyl-N-acetyl oxygen ethylaniline simultaneously, coupling component and diazonium product are carried out and flow coupled reaction, after coupling, material is continued to stir 2 hours, then carrying out suction filtration drains, with cold water washing, arrive again neutral, dry up, obtain the finished product.After measured, in products obtained therefrom, DISPERSE ORANGE 30 200 30 chromatogram content are 99.5%, and polychlorobiphenyl amine content wherein is lower than 5ppm; Product yield 98%; The intensity of the former dyestuff of product is 375%, and coloured light is gorgeous.
Comparative example
This Comparative Examples provides a kind of preparation method of DISPERSE ORANGE 30 200 30, and it comprises the steps:
(1), diazotization reaction: get commercially available industrial goods 2,6-dichloro p-Nitroaniline 195 grams, (chromatogram content is 95.3wt%) adds 98% sulfuric acid 300 grams to cool to 10～15 degree then to drip nitrosyl sulfuric acid and make it to occur diazotization reaction and obtain diazonium product solution;
(2) coupled reaction: step (1) gained diazonium product solution is cooled to-5～0 ℃, then join side by side in the coupling beaker with coupling component N-cyanoethyl-N-acetyl oxygen ethylaniline gram.After coupling, material is continued to stir 2 hours, then enter the sheet frame binder, then arrive neutrality with cold water washing, dry up, obtain the finished product.In product, DISPERSE ORANGE 30 200 30 chromatogram content are 91%, polychlorobiphenyl amine content 4.5%, and product yield 93%, the intensity of the former dyestuff of product is 330%, coloured light is approximate.
Comparative example and embodiment 1～3 contrast is visible, and Comparative Examples 1 its product yield is lower than the present invention, and wherein contains suitable world forbidding by product polychlorobiphenyl amine.
Above the present invention is described in detail; its purpose is to allow the personage who is familiar with this art can understand content of the present invention and be implemented; can not limit the scope of the invention with this; the equivalence that all spirit according to the present invention are done changes or modifies, and all should be encompassed in protection scope of the present invention.
Claims (5)
1. the preparation method of a DISPERSE ORANGE 30 200 30, comprise (1), diazotization reaction: make 2,6-dichloro p-Nitroaniline carry out diazotization reaction with nitrosyl sulfuric acid in sulfuric acid medium and obtain diazonium product solution; (2) coupled reaction: make step (1) gained diazonium product solution and N-cyanoethyl-N-acetyl oxygen ethylaniline generation coupled reaction generate described DISPERSE ORANGE 30 200 30, it is characterized in that:
In step (1), as raw material, use 2, the chromatogram content of 6-dichloro p-Nitroaniline is more than 99.8wt%, and polychlorobiphenyl amine content wherein is lower than 5ppm, wherein used 2, 6-dichloro p-Nitroaniline is by technical grade 2, 6-dichloro p-Nitroaniline obtains through refining, described treating process is as follows: by technical grade 2, 6-dichloro p-Nitroaniline joins by water, in the mixed system that ethylene glycol monomethyl ether and Dispersant MF form, fully stir, and be heated to 75 ℃～85 ℃, filter, drain, and then with the hot wash of 75 ℃～85 ℃ 2～3 times, filter cake is dried and be get final product, in described treating process, technical grade 2, 6-dichloro p-Nitroaniline, water, the weight proportion of ethylene glycol monomethyl ether and Dispersant MF is 300:400～600:5～15:1,
In step (1), described diazotization reaction is carried out at 0～5 ℃ of temperature.
2. the preparation method of DISPERSE ORANGE 30 200 30 according to claim 1, it is characterized in that: step (1) detailed process is: will make with extra care 2,6-dichloro p-Nitroaniline adds in reactor, the sulfuric acid that adds 98wt%, cool to 0～5 ℃, then drip nitrosyl sulfuric acid and make to occur diazotization reaction, reaction finishes and obtains diazonium product solution.
3. the preparation method of DISPERSE ORANGE 30 200 30 according to claim 1, it is characterized in that: the coupled reaction of step (2) is carried out under the existence of catalyzer, described catalyzer is paregal O, dispersion agent NNO or the combination of the two, the consumption of catalyzer is N-cyanoethyl-N-acetyl oxygen ethylaniline 0.8%～1.2% of quality that feeds intake.
4. according to the preparation method of the described DISPERSE ORANGE 30 200 30 of claim 1 or 3, it is characterized in that: the temperature of the coupled reaction of step (2) is 0 ℃～10 ℃.
5. the preparation method of DISPERSE ORANGE 30 200 30 according to claim 4, it is characterized in that: the detailed process of step (2) is: add water in reactor, control 0 ℃～10 ℃ of temperature, then add catalyzer, finally drip step (1) the gained diazonium product solution that cools to-5～0 ℃, open the valve of N-cyanoethyl-N-acetyl oxygen ethylaniline simultaneously, N-cyanoethyl-N-acetyl oxygen ethylaniline and diazonium product solution are carried out and flow coupled reaction, after coupling, material is continued to stir 1.5～2.5 hours, then enter sheet frame, binder, with cold water washing, arrive again neutral, dry up, obtain DISPERSE ORANGE 30 200 30 products.
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| CN 201210063166 CN102618061B (en) | 2012-03-12 | 2012-03-12 | Preparation method for 2-[N-(2-cyanoethyl)-4-[(2,6-dichloro-4-nitrobenzophenone)azo]anilino]ethyl acetate |
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| CN105038296B (en) * | 2015-07-02 | 2017-08-25 | 沈阳化工研究院有限公司 | A kind of preparation method of heterocycle azo dyestuff |
| CN105462284B (en) * | 2015-12-15 | 2017-07-25 | 浙江闰土研究院有限公司 | A kind of preparation method of environmental-friendly disperse dye |
| CN108129871A (en) * | 2017-12-29 | 2018-06-08 | 东营安诺其纺织材料有限公司 | A kind of production technology of disperse orange |
| CN109438255A (en) * | 2018-12-12 | 2019-03-08 | 东营安诺其纺织材料有限公司 | A kind of processing method and its application of digit printing disperse dyes |
| CN111517963A (en) * | 2020-06-02 | 2020-08-11 | 杭州福莱蒽特科技有限公司 | Preparation method of environment-friendly 2, 6-dichloro-4-nitroaniline |
| CN114437560A (en) * | 2022-01-24 | 2022-05-06 | 苏州市罗森助剂有限公司 | Preparation process of disperse dye |
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