CN102212029A - Synthesis method of disperse blue 60 intermediate - Google Patents
Synthesis method of disperse blue 60 intermediate Download PDFInfo
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- CN102212029A CN102212029A CN2011100994973A CN201110099497A CN102212029A CN 102212029 A CN102212029 A CN 102212029A CN 2011100994973 A CN2011100994973 A CN 2011100994973A CN 201110099497 A CN201110099497 A CN 201110099497A CN 102212029 A CN102212029 A CN 102212029A
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- diamino
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Abstract
The invention relates to a synthesis method of disperse blue 60 intermediate. The synthesis method is characterized by comprising the following steps: based on 1,4-diamido-2,3-dicyano anthraquinone serving as a raw material and concentrated sulfuric acid and an organic solvent serving as reaction mediums, heating, insulating and oxidizing, and then hydrolyzing so as to obtain the disperse blue 60 intermediate, namely 1,4-diamino anthraquinone-2,3-dicarboxylic imine, wherein the organic solvent is toluene, chlorobenzene or dichloroethane, the weight ratio of concentrated sulfuric acid to 1,4-diamido-2,3-dicyano anthraquinone is (2-4):1, and the weight ratio of organic solvent to 4-diamido-2,3-dicyano anthraquinone is (1-3):1. In the method, the concentrated sulfuric acid and the organic solvent are used as the reaction mediums, so that the use amount of sulfuric acid is reduced, the crystals of the disperse blue 60 are regular and can be easily filtered, the solid content of filter cake is improved from 50-60% to above 90%, and the coloured light DC value of the disperse blue 60 product is improved by above 0.5.
Description
Technical field
The present invention relates to a kind of synthetic method of Disperse Blue-60 intermediate, more specifically say, the present invention relates to a kind of Disperse Blue-60 intermediate 1,4-diamino-anthraquinone-2, the synthetic method of 3-dicarboxyl imines.
Background technology
Disperse Blue-60 has another name called EX-SF DISPERSE BLUE EX-SF 300 S-GL, disperses bright blue GL, disperses bright blue S-GL, disperses bright blue S-GLR etc., and it is a kind of terylene and BLENDED FABRIC dyestuff thereof of every excellent performance.1,4-diamino-anthraquinone-2,3-dicarboxyl imines is with 1, and 4-diamino-2,3-dicyan anthraquinone are the important intermediate of the synthetic Disperse Blue-60 of raw material, and its chemical formula is as follows:
The method of at present synthetic Disperse Blue-60 intermediate is: with 1,4-diamino-anthraquinone-2,3-dicyan anthraquinone are that raw material is incubated oxidation in sulfuric acid, and hydrolysis makes then.The main drawback of this method is that the used sulfuric acid of hydrolysis is diluted into dilute sulphuric acid after reaction, produces a large amount of useless dilute sulphuric acids.Though dilute sulphuric acid can be carried out recycling by concentrating, thickening equipment has high input and the energy consumption height.Because above-mentioned oxidizing reaction is thermopositive reaction, if reduce the sulfuric acid consumption merely, again can be too much because of heat, produce the retrogradation that becomes sticky of side reaction and reaction mass, cause the sad filter of material, make Disperse Blue-60 intermediate 1,4-diamino-anthraquinone-2, the quality of 3-dicarboxyl imines reduces, and then causes it and γ-methoxy propanamine or γ-ethoxy propylamine to carry out the yield reduction of condensation reaction and make the coloured light deepening of the finished product Disperse Blue-60.
Summary of the invention
The objective of the invention is: providing a kind of can reduce cost, and improves the quality, and then improves the synthetic method of the Disperse Blue-60 intermediate of Disperse Blue-60 yield and quality.
The technical scheme that realizes the object of the invention is: a kind of synthetic method of Disperse Blue-60 intermediate, it is characterized in that, with 1,4-diamino-2,3-dicyan anthraquinone are raw material, with the vitriol oil and organic solvent is reaction medium, the heat tracing oxidation, hydrolysis then makes Disperse Blue-60 intermediate 1,4-diamino-anthraquinone-2,3-dicarboxyl imines;
Described organic solvent is toluene, chlorobenzene or ethylene dichloride;
The described vitriol oil and 1,4-diamino-2, the weight ratio of 3-dicyan anthraquinone consumption is 2～4:1;
Described organic solvent and 1,4-diamino-2, the weight ratio of 3-dicyan anthraquinone consumption is 1～3:1.
The concrete operations of above-mentioned synthetic method are as follows:
In reactor, add the vitriol oil and organic solvent, add 1 under the stirring at normal temperature, 4-diamino-2, the 3-dicyan anthraquinone heated up then, 60～100 ℃ of insulation oxidations 2～6 hours, after testing 1,4-diamino-2, the 3-dicyan anthraquinone is cooled to≤40 ℃ after disappearing, after adding water and being hydrolyzed 2～8 hours, in reactor, feed steam again and carry out steam distillation, the vapor recovery condensation that steams, standing demix, organic solvent layer is preserved and is utilized, remaining material filtering in the reactor, the gained filter cake is washed to neutrality, is Disperse Blue-60 intermediate 1 after the drying, 4-diamino-anthraquinone-2,3-dicarboxyl imines uses for synthetic Disperse Blue-60;
Described organic solvent is toluene, chlorobenzene or ethylene dichloride;
The described vitriol oil and 1,4-diamino-2, the weight ratio of 3-dicyan anthraquinone consumption is 2～4:1;
Described organic solvent and 1,4-diamino-2, the weight ratio of 3-dicyan anthraquinone consumption is 1～3:1;
The described vitriol oil is that massfraction is 98% industrial sulphuric acid.
Technique effect of the present invention is: the synthetic method of the Disperse Blue-60 intermediate that technical solution of the present invention provides is to adopt organic solvent to substitute part of sulfuric acid to be incubated oxidation hydrolysis again, therefore, has following advantage: 1. adopt organic solvent instead of part sulfuric acid, so both reduced the sulfuric acid consumption, also reduced the quantity discharged of spent acid, overcome of the influence of simple reduction sulfuric acid consumption again quality product; 2. instead of part vitriolic organic solvent toluene, chlorobenzene or ethylene dichloride are organic solvents immiscible with water and that can steam altogether with water, therefore, are convenient to reclaim and can utilize again, and be favourable to reducing cost; 3. adopt organic solvent instead of part vitriolic method to be incubated oxidation hydrolysis again, gained material crystallization rule is easily filtered, and makes Disperse Blue-60 intermediate 1,4-diamino-anthraquinone-2, and the yield of 3-dicarboxyl imines improves; 4. adopt solvent instead of part sulfuric acid to be incubated the oxidation intermediate 1 that makes of hydrolysis again, 4-diamino-anthraquinone-2, when 3-dicarboxyl imines and γ-methoxy propanamine or γ-ethoxy propylamine carry out condensation, the crystal rule of the Disperse Blue-60 that makes, easily filter, the solids content of filter cake can be increased to more than 90% by 50～60%, and the coloured light DC value of Disperse Blue-60 product improves more than 0.5.
Embodiment
Below in conjunction with embodiment the present invention is further described in detail, but not limited.
The raw materials used dye well intermediate that is of each embodiment is produced employed commercially available industrial goods, and wherein, the vitriol oil is that massfraction is 98% industrial sulphuric acid.
Embodiment 1 synthetic Disperse Blue-60 intermediate 1,4-diamino-anthraquinone-2,3-dicarboxyl imines
Having agitator, thermometer, feeder, in the reactor of steam distillation device and register, add vitriol oil 40ml(and amount to 73.6g) and organic solvent ethylene dichloride 40ml(amount to 50.1g), add 1 under the stirring at normal temperature, 4-diamino-2,3-dicyan anthraquinone 20g heated up then, 70 ℃ of insulation oxidations 2 hours, after testing 1,4-diamino-2, the 3-dicyan anthraquinone is cooled to 40 ℃ after disappearing, after adding water and being hydrolyzed 2～8 hours, in reactor, feed steam and carry out steam distillation, the vapor recovery condensation that steams, standing demix, the organic solvent layer ethylene dichloride is preserved and is utilized, remaining material filtering in the reactor, the gained filter cake is washed to neutrality, is Disperse Blue-60 intermediate 1 after the drying, 4-diamino-anthraquinone-2,3-dicarboxyl imines 20.4g, yield is 96.1%, 1,4-diamino-anthraquinone-2,3-dicarboxyl imines content is measured for the 96.5%(planimetry), preserve for synthetic Disperse Blue-60 and use;
Wherein, the vitriol oil (73.6g) and 1,4-diamino-2, the weight ratio of 3-dicyan anthraquinone (20g) consumption is 3.68:1; Organic solvent ethylene dichloride (50.1g) and 1,4-diamino-2, the weight ratio of 3-dicyan anthraquinone (20g) consumption is 2.51:1.
Embodiment 2 synthetic Disperse Blue-60 intermediates 1,4-diamino-anthraquinone-2,3-dicarboxyl imines
Substantially the same manner as Example 1, difference was: 65 ℃ of insulation oxidations 3 hours;
Make Disperse Blue-60 intermediate 1,4-diamino-anthraquinone-2,3-dicarboxyl imines 20.3g, yield is 95.7%, 1,4-diamino-anthraquinone-2,3-dicarboxyl imines content is measured for the 96.2%(planimetry), preserve for synthetic Disperse Blue-60 and use.
Embodiment 3 synthetic Disperse Blue-60 intermediates 1,4-diamino-anthraquinone-2,3-dicarboxyl imines
Substantially the same manner as Example 1, difference is: 40ml(amounts to 34.6g with organic solvent toluene) the replacement ethylene dichloride; Wherein, organic solvent toluene (34.6g) and 1,4-diamino-2, the weight ratio 1.73:1 of 3-dicyan anthraquinone (20g) consumption;
Make Disperse Blue-60 intermediate 1,4-diamino-anthraquinone-2,3-dicarboxyl imines 20.8g, yield is 98.0%, 1,4-diamino-anthraquinone-2,3-dicarboxyl imines content is measured for the 96.8%(planimetry), preserve for synthetic Disperse Blue-60 and use.
Embodiment 4 synthetic Disperse Blue-60 intermediates 1,4-diamino-anthraquinone-2,3-dicarboxyl imines
Substantially the same manner as Example 1, difference is: 40ml(amounts to 41.6g with the organic solvent chlorobenzene) the replacement ethylene dichloride; 70 ℃ of insulation oxidations 3 hours; Wherein, organic solvent chlorobenzene (41.6g) and 1,4-diamino-2, the weight ratio 2.08:1 of 3-dicyan anthraquinone (20g) consumption;
Make Disperse Blue-60 intermediate 1,4-diamino-anthraquinone-2,3-dicarboxyl imines 20.2g, yield is 95.2%, 1,4-diamino-anthraquinone-2,3-dicarboxyl imines content is measured for the 96.0%(planimetry), preserve for synthetic Disperse Blue-60 and use.
Embodiment 5 synthetic Disperse Blue-60 intermediates 1,4-diamino-anthraquinone-2,3-dicarboxyl imines
Having agitator, thermometer, feeder, in the reactor of steam distillation device and register, add vitriol oil 900kg and organic solvent ethylene dichloride 500kg, add 1 under the stirring at normal temperature, 4-diamino-2,3-dicyan anthraquinone 300kg heated up then, 70 ℃ of insulation oxidations 4 hours, after testing 1,4-diamino-2, the 3-dicyan anthraquinone is cooled to 40 ℃ after disappearing, after adding water and being hydrolyzed 2～8 hours, in reactor, feed steam again and carry out steam distillation, the vapor recovery condensation that steams, standing demix, the organic solvent layer ethylene dichloride is preserved and is utilized, remaining material filtering in the reactor, the gained filter cake is washed to neutrality, is Disperse Blue-60 intermediate 1 after the drying, 4-diamino-anthraquinone-2,3-dicarboxyl imines 308.2kg, yield is 96.8%, 1,4-diamino-anthraquinone-2,3-dicarboxyl imines content is measured for the 96.8%(planimetry), preserve for synthetic Disperse Blue-60 and use;
Wherein, the vitriol oil (900kg) and 1,4-diamino-2, the weight ratio of 3-dicyan anthraquinone (300kg) consumption is 3:1; Organic solvent ethylene dichloride (500kg) and 1,4-diamino-2, the weight ratio of 3-dicyan anthraquinone (300kg) consumption is 1.66:1.
Embodiment 6 usefulness have the synthetic Disperse Blue-60 intermediate 1 of method (promptly being incubated oxidation hydrolysis again in sulfuric acid medium), 4-diamino-anthraquinone-2,3-dicarboxyl imines now
For the ease of relatively, the vitriol oil and 1 wherein, 4-diamino-2, the weight ratio of 3-dicyan anthraquinone consumption is identical with embodiment 1～4;
In reactor, add vitriol oil 40ml(and amount to 73.6g), stir adding 1 down, 4-diamino-2,3-dicyan anthraquinone 20g heats up then 70 ℃ of insulation oxidations 2 hours, and after testing 1,4-diamino-2, the 3-dicyan anthraquinone is cooled to 40 ℃ after disappearing, and adds water then and is hydrolyzed, hydrolysis finishes to filter, the gained filter cake is washed to neutrality, is Disperse Blue-60 intermediate 1 after the drying, 4-diamino-anthraquinone-2,3-dicarboxyl imines 20.2g, yield is 95.6%, 1,4-diamino-anthraquinone-2,3-dicarboxyl imines content is measured for the 96.2%(planimetry), preserve for synthetic contrast sample Disperse Blue-60 and use;
Wherein, the vitriol oil (73.6g) and 1,4-diamino-2, the weight ratio of 3-dicyan anthraquinone (20g) consumption is 3.68:1.
Embodiment 7 preparation Disperse Blue-60s
1. appoint and get the Disperse Blue-60 intermediate 1 that one of embodiment 1～5 makes, 4-diamino-anthraquinone-2, be warming up to 80～82 ℃ after 3-dicarboxyl imines 40g and 90g γ-methoxy propanamine and other solvent and carry out condensation reaction, be incubated 4 hours and finish condensation, be cooled to 35 ℃ then, suction filtration is after the washing of gained filter cake is clean, the solids content of measuring filter cake is 91.2%, makes the 45.9g Disperse Blue-60 after the filter cake oven dry; The gained solvent reclaims, and after testing, consumes γ-methoxy propanamine 16.7g.
Press standard dye measure the coloured light of gained Disperse Blue-60: DC for+0.11, DH is+0.02.
2. get the existing method synthetic Disperse Blue-60 intermediate 1 of embodiment 6 usefulness, 4-diamino-anthraquinone-2, be warming up to 80～82 ℃ after 3-dicarboxyl imines 40g and 90g γ-methoxy propanamine and other solvent and carry out condensation reaction, be incubated 4 hours and finish condensation, be cooled to 35 ℃ then, suction filtration is after the washing of gained filter cake is clean, the solids content of measuring filter cake is 58.2%, makes the 45.7g Disperse Blue-60 after the filter cake oven dry; The gained solvent reclaims, and after testing, consumes γ-methoxy propanamine 34.7g.
Press standard dye measure the coloured light of gained Disperse Blue-60: DC for-0.56, DH is-0.62.
With 1. and 2. comparing as can be seen of embodiment 7, the Disperse Blue-60 intermediate that makes with synthetic method of the present invention can make the solids content of filter cake bring up to 91.2% by 58.2%, the crystal rule of the Disperse Blue-60 that proof makes is easily filtered, and is very favourable to enhancing productivity; The coloured light value of gained Disperse Blue-60, the Disperse Blue-60 intermediate that proof makes with the inventive method can improve the coloured light of product, also prove simultaneously the lower sulfuric acid and 1 of the inventive method use, 4-diamino-2, the weight ratio of 3-dicyan anthraquinone consumption, still can guarantee the quality of the Disperse Blue-60 intermediate that obtained and, reduce useless vitriolic growing amount and useless vitriolic processing costs by the quality of its synthetic Disperse Blue-60.
Claims (2)
1. the synthetic method of a Disperse Blue-60 intermediate is characterized in that, with 1, and 4-diamino-2, the 3-dicyan anthraquinone is a raw material, is reaction medium with the vitriol oil and organic solvent, heat tracing oxidation, hydrolysis then, make Disperse Blue-60 intermediate 1,4-diamino-anthraquinone-2,3-dicarboxyl imines;
Described organic solvent is toluene, chlorobenzene or ethylene dichloride;
The described vitriol oil and 1,4-diamino-2, the weight ratio of 3-dicyan anthraquinone consumption is 2～4:1;
Described organic solvent and 1,4-diamino-2, the weight ratio of 3-dicyan anthraquinone consumption is 1～3:1.
2. synthetic method according to claim 1 is characterized in that concrete operations are as follows:
In reactor, add the vitriol oil and organic solvent, add the vitriol oil and organic solvent, add 1 under the stirring at normal temperature, 4-diamino-2,3-dicyan anthraquinone, heat up then, 60～100 ℃ of insulation oxidations 2～6 hours, after testing 1,4-diamino-2, after the 3-dicyan anthraquinone disappears, be cooled to≤40 ℃, after adding water and being hydrolyzed 2～8 hours, in reactor, feed steam again and carry out steam distillation, the vapor recovery condensation that steams, standing demix, organic solvent layer is preserved and is utilized, remaining material filtering in the reactor, and the gained filter cake is washed to neutrality, be Disperse Blue-60 intermediate 1 after the drying, 4-diamino-anthraquinone-2,3-dicarboxyl imines uses for synthetic Disperse Blue-60;
Described organic solvent is toluene, chlorobenzene or ethylene dichloride;
The described vitriol oil and 1,4-diamino-2, the weight ratio of 3-dicyan anthraquinone consumption is 2～4:1;
Described organic solvent and 1,4-diamino-2, the weight ratio of 3-dicyan anthraquinone consumption is 1～3:1;
The described vitriol oil is that massfraction is 98% industrial sulphuric acid.
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Cited By (5)
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| CN103965648A (en) * | 2013-01-31 | 2014-08-06 | 江苏道博化工有限公司 | Disperse blue 359 preparation method |
| CN104448888A (en) * | 2014-11-29 | 2015-03-25 | 萧县凯奇化工科技有限公司 | Preparation method of vat olive green B |
| CN111574484A (en) * | 2020-06-10 | 2020-08-25 | 浙江博澳新材料股份有限公司 | Water-saving and environment-friendly anhydride preparation method |
| CN116082219A (en) * | 2022-08-11 | 2023-05-09 | 山东大学 | Preparation method of disperse blue 60-based disperse dye |
| CN116855099A (en) * | 2023-06-30 | 2023-10-10 | 浙江闰土股份有限公司 | Process for preparing disperse blue 60 and its derivative |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103965648A (en) * | 2013-01-31 | 2014-08-06 | 江苏道博化工有限公司 | Disperse blue 359 preparation method |
| CN103965648B (en) * | 2013-01-31 | 2015-09-30 | 江苏道博化工有限公司 | A kind of method preparing dispersion blue 359 |
| CN104448888A (en) * | 2014-11-29 | 2015-03-25 | 萧县凯奇化工科技有限公司 | Preparation method of vat olive green B |
| CN111574484A (en) * | 2020-06-10 | 2020-08-25 | 浙江博澳新材料股份有限公司 | Water-saving and environment-friendly anhydride preparation method |
| CN111574484B (en) * | 2020-06-10 | 2021-11-09 | 浙江博澳新材料股份有限公司 | Water-saving and environment-friendly anhydride preparation method |
| CN116082219A (en) * | 2022-08-11 | 2023-05-09 | 山东大学 | Preparation method of disperse blue 60-based disperse dye |
| CN116082219B (en) * | 2022-08-11 | 2024-04-26 | 山东大学 | Preparation method of disperse blue 60-based disperse dye |
| CN116855099A (en) * | 2023-06-30 | 2023-10-10 | 浙江闰土股份有限公司 | Process for preparing disperse blue 60 and its derivative |
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