CN102618061A - 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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- CN102618061A CN102618061A CN2012100631669A CN201210063166A CN102618061A CN 102618061 A CN102618061 A CN 102618061A CN 2012100631669 A CN2012100631669 A CN 2012100631669A CN 201210063166 A CN201210063166 A CN 201210063166A CN 102618061 A CN102618061 A CN 102618061A
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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 reaction on 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)-4-[(2,6-two chloro-4-nitrophenyls) azo] anilino] ETHYLE ACETATE by name, structural formula is following:
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 polyester-viscose blended coloration of textile materials and cotton-polyester blend cloth.The main working method of DISPERSE ORANGE 30 200 30 is with 2 of technical grade at present, and 6-dichloro p-Nitroaniline is a raw material, in sulfuric acid medium, drips nitrosyl sulfuric acid and carries out diazotization reaction, and then make with coupling component N-cyanoethyl-N-acetyl oxygen ethyl coupling.Because at present domestic technical grade 2.6-two-chlorine p-nitrophenyl amine content is all about 95%, and contain the world forbidding by product polychlorobiphenyl amine about 4.5%.Therefore DISPERSE ORANGE 30 200 30 coloured light of producing with this method are dark partially, and intensity is low, and especially weak point is to contain polychlorobiphenyl amine in the product, has hindered product and has marched to the world market.
Summary of the invention
technical problem to be solved by this invention is the deficiency that overcomes 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:
The preparation method of
a kind of DISPERSE ORANGE 30 200 30 comprises (1), diazotization reaction: make 2,6-dichloro p-Nitroaniline carries out diazotization reaction with nitrosyl sulfuric acid and obtains diazonium product solution in sulfuric acid medium; (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 the 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 the step (1), said diazotization reaction is carried out under 0～5 ℃ of temperature.
preferably, step (1) is employed 2,6-dichloro p-Nitroaniline is by technical grade 2; 6-dichloro p-Nitroaniline obtains through refining, and said treating process is following: with technical grade 2,6-dichloro p-Nitroaniline joins in the mixed system of being made up of water, ethylene glycol monomethyl ether and Dispersant MF; Fully stir, and be heated to 75 ℃～85 ℃, filter; Drain, and then with 75 ℃～85 ℃ hot wash 2 ~ 3 times, the filter cake oven dry promptly gets.In the 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.
are according to a concrete aspect of the present invention; Step (1) detailed process is: with purified 2; 6-dichloro p-Nitroaniline adds in the reactor drum, adds the sulfuric acid of 98wt%, cools to 0 ~ 5 ℃; Drip nitrosyl sulfuric acid then and make the generation diazotization reaction, reaction finishes promptly to get diazonium product solution.
preferably; The coupled reaction of step (2) is carried out in the presence of catalyzer, and said catalyzer can be paregal O, dispersion agent NNO or the combination of the two; Catalyst consumption 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: in reactor drum, add entry, 0 ℃～10 ℃ of controlled temperature; Add catalyzer then, drip step (1) the gained diazonium product solution that cools to-5 ~ 0 ℃ at last, open the valve of N-cyanoethyl-N-acetyl oxygen MEA simultaneously; N-cyanoethyl-N-acetyl oxygen MEA and diazonium product are carried out and flow coupled reaction, after coupling finishes material is continued to stir 1.5～2.5 hours, get into sheet frame then; Binder; Arrive neutrality with cold water washing again, dry up, promptly get DISPERSE ORANGE 30 200 30 products.
Because adopt the enforcement of above technical scheme, the present invention compared with prior art has following advantage:
(1) do not contain international forbidding by product polychlorobiphenyl amine in the inventive method products obtained therefrom, allusion quotation has been decided the basis in order to explore world market;
The yield of
(2), product is high, purity is high, and coloured light is gorgeous.
Embodiment
Embodiment 1
Preparing method according to the DISPERSE ORANGE 30 200 30 of present embodiment comprises the steps:
(1), 2,6-dichloro p-Nitroaniline refining:, the 1000ml beaker of whipping appts adds entry 500 grams in being housed, water-soluble solvent ethylene glycol monomethyl ether 10 grams, Dispersant MF 1 gram fully stirs.Add commercially available technical grade 2 then, 6-dichloro p-Nitroaniline 300 grams fully stir and are warmed up to 80 ℃; Filtered while hot is drained, and then with 80 ℃ hot wash 2 ~ 3 times; Filter cake is a purified 2,6-dichloro p-Nitroaniline, and its chromatogram content is more than the 99.8wt%; Polychlorobiphenyl amine content wherein is lower than 5ppm, filter cake dry 195 the gram.
(2), diazotization reaction: get above-mentioned purified 2,6-dichloro p-Nitroaniline 195 gram adds 98% sulfuric acid 300 grams, cools to 0 ~ 5 ℃ and drips nitrosyl sulfuric acid then and make and diazotization reaction takes place obtain diazonium product solution.
(3), coupled reaction: the ice and the water that in 2000 milliliters beaker, add some amount; Add 1 gram paregal O then, then the above-mentioned diazonium product drips of solution that cools to-5 ~ 0 ℃ is added in the beaker, open the valve of coupling component N-cyanoethyl-N-acetyl oxygen MEA simultaneously; Coupling component and diazonium product are carried out and flow coupled reaction; After coupling finishes material is continued to stir 2 hours, then carry out suction filtration and drain, arrive neutral again with cold water washing; Dry up, promptly get the finished product.Through measuring, in the 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
Preparing method according to the DISPERSE ORANGE 30 200 30 of present embodiment comprises the steps:
(1), 2,6-dichloro p-Nitroaniline refining:, the 1000ml beaker of whipping appts adds entry 500 grams in being housed, water-soluble solvent ethylene glycol monomethyl ether 10 grams, Dispersant MF 1 gram fully stirs.Add commercially availablely 2 then, 6-dichloro p-Nitroaniline 300 grams fully stir and are warmed up to 80 ℃; Filtered while hot is drained, and then with 80 ℃ hot wash 2 ~ 3 times; Filter cake is a purified 2,6-dichloro p-Nitroaniline, and its chromatogram content is more than the 99.8wt%; Polychlorobiphenyl amine content wherein is lower than 5ppm, filter cake dry 195 the gram.
(2), diazotization reaction: get above-mentioned purified 2,6-dichloro p-Nitroaniline 195 gram adds 98% sulfuric acid 300 grams, cools to 0 ~ 5 ℃ and drips nitrosyl sulfuric acid then and make and diazotization reaction takes place obtain diazonium product solution.
(3), coupled reaction: the ice and the water that in 2000 milliliters beaker, add some amount; Add 1 gram dispersion agent NNO then, then the above-mentioned diazonium product drips of solution that cools to-5 ~ 0 ℃ is added in the beaker, open the valve of coupling component N-cyanoethyl-N-acetyl oxygen MEA simultaneously; Coupling component and diazonium product are carried out and flow coupled reaction; After coupling finishes material is continued to stir 2 hours, then carry out suction filtration and drain, arrive neutral again with cold water washing; Dry up, promptly get the finished product.Through measuring, in the 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
Preparing method according to the DISPERSE ORANGE 30 200 30 of present embodiment comprises the steps:
(1), 2,6-dichloro p-Nitroaniline refining:, the 1000ml beaker of whipping appts adds entry 500 grams in being housed, water-soluble solvent ethylene glycol monomethyl ether 10 grams, Dispersant MF 1 gram fully stirs.Add commercially availablely 2 then, 6-dichloro p-Nitroaniline 300 grams fully stir and are warmed up to 80 ℃, filtered while hot; Drain, and then with 80 ℃ hot wash 2 ~ 3 times, filter cake is a purified 2; 6-dichloro p-Nitroaniline, its chromatogram content is more than the 99.8wt%, filter cake dry 195 the gram.
(2), diazotization reaction: get above-mentioned purified 2,6-dichloro p-Nitroaniline 195 gram adds 98% sulfuric acid 300 grams, cools to 0 ~ 5 ℃ and drips nitrosyl sulfuric acid then and make and diazotization reaction takes place obtain diazonium product solution.
(3), coupled reaction: the ice and the water that in 2000 milliliters beaker, add some amount; Add 0.5 gram dispersion agent NNO and 0.5 gram paregal O then, then the above-mentioned diazonium product drips of solution that cools to-5 ~ 0 ℃ is added in the beaker, open the valve of coupling component N-cyanoethyl-N-acetyl oxygen MEA simultaneously; Coupling component and diazonium product are carried out and flow coupled reaction; After coupling finishes material is continued to stir 2 hours, then carry out suction filtration and drain, arrive neutral again with cold water washing; Dry up, promptly get the finished product.Through measuring, in the 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 gram, (chromatogram content is 95.3wt%) add 98% sulfuric acid 300 grams and cool to 10 ~ 15 degree and drip nitrosyl sulfuric acid then and make it to take place diazotization reaction and obtain diazonium product solution;
(2) coupled reaction: step (1) gained diazonium product solution is cooled to-5 ~ 0 ℃, join side by side in the coupling beaker with coupling component N-cyanoethyl-N-acetyl oxygen MEA gram then.After coupling finishes material is continued to stir 2 hours, then get into the sheet frame binder, arrive neutrality with cold water washing again, dry up, promptly get the finished product.In the 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.
are visible with comparative example and embodiment 1 ~ 3 contrast, and Comparative Examples 1 its product yield is lower than the present invention, and wherein contain suitable world forbidding by product polychlorobiphenyl amine.
More than the present invention has been done detailed description; Its purpose is to let the personage that is familiar with this art can understand content of the present invention and implements; Can not limit protection scope of the present invention with this; All equivalences of doing according to spirit of the present invention change or modify, and all should be encompassed in protection scope of the present invention
Claims (7)
1. the preparation method of a DISPERSE ORANGE 30 200 30 comprises (1), diazotization reaction: make 2,6-dichloro p-Nitroaniline carries out diazotization reaction with nitrosyl sulfuric acid and obtains diazonium product solution in sulfuric acid medium; (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, it is characterized in that:
As 2 of raw material use, the chromatogram content of 6-dichloro p-Nitroaniline is more than 99.8wt%, and polychlorobiphenyl amine content wherein is lower than 5ppm in the step (1);
In the step (1), said diazotization reaction is carried out under 0～5 ℃ of temperature.
2. the preparation method of DISPERSE ORANGE 30 200 30 according to claim 1 is characterized in that: step (1) is employed 2, and 6-dichloro p-Nitroaniline is by technical grade 2; 6-dichloro p-Nitroaniline obtains through refining, and said treating process is following: with technical grade 2,6-dichloro p-Nitroaniline joins in the mixed system of being made up of water, ethylene glycol monomethyl ether and Dispersant MF; Fully stir; And be heated to 75 ℃～85 ℃, and filter, drain; And then with 75 ℃～85 ℃ hot wash 2 ~ 3 times, the filter cake oven dry promptly gets.
3. the preparation method of DISPERSE ORANGE 30 200 30 according to claim 2 is characterized in that: in the said treating process, and 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.
4. according to the preparation method of claim 2 or 3 described DISPERSE ORANGE 30 200s 30; It is characterized in that: step (1) detailed process is: with purified 2; 6-dichloro p-Nitroaniline adds in the reactor drum, adds the sulfuric acid of 98wt%, cools to 0 ~ 5 ℃; Drip nitrosyl sulfuric acid then and make the generation diazotization reaction, reaction finishes promptly to get diazonium product solution.
5. 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 in the presence of catalyzer; Said catalyzer is a paregal O; Dispersion agent NNO or the combination of the two, catalyst consumption are N-cyanoethyl-N-acetyl oxygen ethyl 0.8% ~ 1.2% of quality that feeds intake.
6. according to the preparation method of claim 1 or 5 described DISPERSE ORANGE 30 200s 30, it is characterized in that: the temperature of the coupled reaction of step (2) is 0 ℃～10 ℃.
7. the preparation method of DISPERSE ORANGE 30 200 30 according to claim 5 is characterized in that: the detailed process of step (2) is: in reactor drum, add entry, 0 ℃～10 ℃ of controlled temperature; Add catalyzer then, drip step (1) the gained diazonium product solution that cools to-5 ~ 0 ℃ at last, open the valve of N-cyanoethyl-N-acetyl oxygen MEA simultaneously; N-cyanoethyl-N-acetyl oxygen MEA and diazonium product solution are carried out and flow coupled reaction, after coupling finishes material is continued to stir 1.5～2.5 hours, get into sheet frame then; Binder; Arrive neutrality with cold water washing again, dry up, promptly get 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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Cited By (6)
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| CN105038296A (en) * | 2015-07-02 | 2015-11-11 | 沈阳化工研究院有限公司 | Preparation method of heterocyclic azo dye |
| CN105462284A (en) * | 2015-12-15 | 2016-04-06 | 浙江闰土研究院有限公司 | Method for preparing environment-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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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105038296A (en) * | 2015-07-02 | 2015-11-11 | 沈阳化工研究院有限公司 | Preparation method of heterocyclic azo dye |
| CN105462284A (en) * | 2015-12-15 | 2016-04-06 | 浙江闰土研究院有限公司 | Method for preparing environment-friendly disperse dye |
| 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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