CN101817989B - Method for preparing disperse blue 60 and homologues thereof - Google Patents
Method for preparing disperse blue 60 and homologues thereof Download PDFInfo
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Abstract
The invention discloses a method for preparing disperse blue 60 and homologues thereof. The method comprises the following steps of: adding a 1,4-diamino-2,3-dicarboximide wet product into water, adding gamma-alkoxy propylamine into the mixture, performing condensation reaction under the conditions that the temperature is between 95 and 105 DEG C and the reaction pressure is between 0.07 and 0.18 MPa for 4 to 6 hours, and after the condensation reaction, filtering, washing and drying to obtain the disperse blue 60 and the homologues thereof; and after completing the condensation reaction, re-using the filtered mother solution in the next condensation reaction. In the method for preparing the disperse blue 60 and the homologues thereof, water is used as a solvent, so that the method realizes pollution-free production and circular economy, and has extremely obvious economic and environmental benefits.
Description
Technical field
The invention belongs to preparation of dyestuff field, relate in particular to the preparation method of a kind of Disperse Blue-60 and homologue thereof.
Background technology
The existing production method of Disperse Blue-60 is mainly that to take Isosorbide-5-Nitrae-diamino-anthraquinone leuco compound be raw material, in orthodichlorobenzene medium, reacts and makes 1 with chlorsulfonic acid, 4-diamino-2,3-disulfonic acid anthraquinone, is then adjusted to pH to 8 left and right with liquid caustic soda, utilize steam distillation to steam orthodichlorobenzene, after filtration, join cyaniding pot, carry out cyanogenation, drip dilute sulphuric acid and control pH value, cyanogenation temperature is 98 ℃～100 ℃, after cyaniding completes, adds Sulfothiorine to remove poison; Send again Filter Press to wash to neutrality, dry.In oxidation pot, add the vitriol oil, be no more than under 65 ℃ of conditions, add dried Isosorbide-5-Nitrae-diamino-2,3-dicyan anthraquinone, 60 ℃～90 ℃ insulation reaction, and then add water hydrolysis closed loop and generate Isosorbide-5-Nitrae-diamino-2,3-dicarboximide, after filtering, washing, then add aqueous sodium hydroxide solution, generate suitable sodium salt entirely water-soluble, add activated carbon adsorption to remove out impurity, acidifying becomes 1 again, 4-diamino-2,3-dicarboximide, dry obtain being dried 1,4-diamino-2,3-dicarboximide; Then by 1 of oven dry, 4-diamino-2,3-dicarboximide and γ-methoxy propanamine are in anhydrous ethanol medium, under reflux temperature, carry out condensation reaction, reacted rear filtration, obtain Disperse Blue-60 filter cake, the mother liquor after filtration steams ethanol and γ-methoxy propanamine by distillation again, and the ethanol steaming and γ-methoxy propanamine be the condensation reaction of reuse next batch again.But condensation product Disperse Blue-60 contains certain solubleness in ethanol and γ-methoxy propanamine causes Disperse Blue-60 yield low; In Disperse Blue-60 filter cake after filtration, contain a certain amount of ethanol and γ-methoxy propanamine, cause ethanol and γ-methoxy propanamine to consume high; Isosorbide-5-Nitrae-diamino-2 used, 3-dicarboximide must be dried, and drying course also needs to consume a certain amount of steam; Using dehydrated alcohol is inflammable explosive article, exists certain potential safety hazard in condensation reaction and still-process.
Dye processing plant, Suzhou Wu family health etc. (are improved one key operation that disperses bright blue S-GL coloured light, Wu Jiakang, Shanghai dyestuff, 1998,26 (5): 27) propose to improve the bright blue coloured light method of dispersion, one key operation is wherein that oxide compound is adjusted after basic hydrolysis, before Acid precipitation, solution be filtered to remove insoluble impurities, the coloured light of obtaining, this is mainly Isosorbide-5-Nitrae-diamino-2,3-dicarboximide intermediate method of purification.
Patent documentation CN101130640 mentions a kind of Disperse Blue-60 and homologue synthetic method craft improves, hydrolysis is obtained to 1,4-diamino-anthraquinone-2,3-dicarboximide generates corresponding sodium salt entirely water-soluble with reacting with sodium hydroxide, add again activated carbon to remove impurity, filtered while hot, acidifying closed loop again obtains 1,4-diamino-anthraquinone-2,3-dicarboxylic anhydride, this acid anhydrides obtains Disperse Blue-60 product and homologue thereof in 40-50 ℃ of insulation reaction 2-3 hour in pure γ-methoxy propanamine (or γ-ethoxy propylamine) medium.Due to Isosorbide-5-Nitrae-diamino-anthraquinone-2, the solubleness of 3-dicarboximide in water is poor, does not also have at present bibliographical information to adopt to take the preparation method that water is solvent.
Summary of the invention
The invention provides that a kind of production cost is low, technique is simple and the eco-friendly method of preparing Disperse Blue-60 and homologue thereof.
A preparation method for Disperse Blue-60 and homologue thereof, step comprises:
(1) in sulfonation reaction still, add orthodichlorobenzene, the dehydration that heats up, after dehydration, cooling drops into Isosorbide-5-Nitrae-diamino-anthraquinone, drips chlorsulfonic acid and carries out sulfonation reaction; After sulfonation completes, with liquid adjusting PH with base to 8 left and right, reaction distillation, by distillate suction cyaniding pot; Add sodium cyanide solution, then add reserve salt to carry out cyaniding, drip dilute sulphuric acid and control pH value, cyanogenation temperature is 98 ℃; Cyaniding completes, and in cyaniding product, adds sodium thiosulfate to remove poison, filters, and filter cake washing, to neutrality, is dried; At oxidation pot, add the vitriol oil, at 65 ℃, add dry 1 being no more than, 4-diamino-2,3-dicyan anthraquinone, 60～75 ℃ of insulation reaction, reaction completes, suction dilution pot, dilute with water, filtration, filter cake washing, then join filter cake in aqueous sodium hydroxide solution, regulating pH value is alkalescence, add activated carbon adsorption to remove out impurity, be acidified to pH value for acid, filter the mother liquor obtaining and be collected in mother liquor tank, filter cake washing is neutral to pH, obtain Isosorbide-5-Nitrae-diamino-2,3-dicarboximide anthraquinone;
(2) by Isosorbide-5-Nitrae-diamino-2,3-dicarboximide anthraquinone is put in water, adds γ-alkoxy propyl amine, carries out condensation reaction, and condensation completes filtration, and washing is dried and obtained Disperse Blue-60 and homologue thereof;
In condensation reaction, adopt water as reaction solvent, adding of γ-alkoxy propyl amine, makes Isosorbide-5-Nitrae-diamino-2, and the solubleness of 3-dicarboximide anthraquinone in the aqueous solution increases, and preferably, the mass ratio of water and γ-alkoxy propyl amine is 8: 1～2;
In order to improve raw material Isosorbide-5-Nitrae-diamino-2, the transformation efficiency of 3-dicarboximide anthraquinone, and consider after condensation that mother liquor can recovery, so Isosorbide-5-Nitrae-diamino-2 in condensation reaction, the mol ratio of 3-dicarboximide anthraquinone and γ-alkoxy propyl amine is 1: 2～5;
Wherein, γ-alkoxy propyl amine is preferably γ-methoxy propanamine or γ-ethoxy propylamine.
Wherein, the condition of condensation reaction is: temperature: 95～105 ℃, and pressure: 0.07～0.18MPa, the reaction times is: 4～6h.Selection is controlled at certain temperature, carries out the reaction of certain hour under pressure, is conducive to the raising of the complete and quality product of reaction.
The mother liquor that after condensation reaction completes, filtration obtains can direct reuse in next batch condensation reaction, the a small amount of Disperse Blue-60 or its homologue that in mother liquor, dissolve so both can have been reclaimed, improve productive rate and the rate of recovery of overall product, can avoid again solvent and reagent in mother liquor to reclaim environmental pollution and the energy expenditure of bringing; In addition, also can improve the utilization ratio of γ-methoxy propanamine or γ-ethoxy propylamine; Apply mechanically in the process of mother liquor, if there is unnecessary mother liquor, can reclaim γ-alkoxy propyl amine by the method for distillation, as raw material, use again.
Shown in the following chemical equation of preparation process of Disperse Blue-60 of the present invention and homologue thereof:
Wherein R is methyl or ethyl.
The present invention's raw material reagent used is and is applicable to the commercially available industrial goods that dye well intermediate is used, used 1,4-diamino-2, all to take Isosorbide-5-Nitrae-diamino-anthraquinone leuco compound be raw material to 3-dicarboximide anthraquinone by existing, through chlorosulphonation, distillation, cyaniding, oxidation, hydrolysis, refine etc., obtain 1,4-diamino-2,3-dicarboximide anthraquinone, filtration, washing obtain filter cake, without dry, can be directly used in condensation reaction.
The beneficial effect that the present invention obtains is:
(1) in condensation reaction water consumption substitution take dehydrated alcohol as reaction solvent, solved the consumption problem of using environmental protection, safety problem and ethanol that dehydrated alcohol brings;
(2) the present invention adopts wet product 1,4-diamino-2,3-dicarboximide anthraquinone replaces Isosorbide-5-Nitrae-diamino-2 of dry product, 3-dicarboximide anthraquinone, solved oven dry problem, every batch by 500kg Isosorbide-5-Nitrae-diamino-2 of giving money as a gift, 3-dicarboximide anthraquinone meter, every batch can be reduced 1.2 tons of moisture evaporations, and reducing steam consumption is 1.2 tons of left and right;
(3) by filtering after condensation reaction in the mother liquor reuse next batch condensation reaction obtaining, the Disperse Blue-60 dissolving in the mother liquor that filtration after condensation reaction is obtained etc. is back to next batch condensation reaction, can on the basis of original technique, improve 5～10% yield, solve the waste of distillation γ-alkoxy propyl amine steam consumption and γ-alkoxy propyl amine, reduced distillation energy consumption and the pollution to environment;
(4) condensation reaction adopts and carries out at certain pressure and temperature, has guaranteed the quality of the complete and the finished product of condensation reaction;
(5) adopt method products obtained therefrom Disperse Blue-60 of the present invention and homologue quality thereof good and very stable, product yield is high, and γ-alkoxy propyl amine consumes low.
Embodiment
Embodiment 1
1,4-diamino-2,3-dicarboximide anthraquinone is to adopt method well known in the art synthetic, and concrete steps are: in sulphonation kettle, add 2000kg orthodichlorobenzene, be warming up to 120 ℃ of dehydrations, be cooled to 50 ℃ and drop into 250kg 1,4-diamino-anthraquinone, drips 480kg chlorsulfonic acid at 50～55 ℃ and carries out sulfonation reaction, finishes, slowly be warming up to 140 ℃, 140～145 ℃ of insulation reaction 7 hours; After sulfonation completes, be cooled to 70 ℃, in still kettle with adding water 3000L, the sulfonation material that suction has been got ready, then use liquid adjusting PH with base to 8 left and right, reaction distillation, distillation is finished, and filters; Filtrate proceeds in cyaniding pot, adds 30% sodium cyanide solution 500kg, then adds reserve salt to carry out cyaniding, and dripping dilute sulphuric acid control pH value is 9.0-9.5, and cyanogenation temperature is 98 ℃; Cyaniding is finished, and in cyaniding product, adds sodium thiosulfate to remove poison, and filtration washing, to neutrality, is dried; Add vitriol oil 500L, at 65 ℃, add dry Isosorbide-5-Nitrae-diamino-2 being no more than, 3-dicyan anthraquinone 150kg, 60～75 ℃ of insulation reaction, reaction is finished, then suction dilution pot, being diluted with water to acidity is 20-23%, filters, after washing, then adds the suitable sodium salt of the generation of 50-70kg sodium hydroxide entirely water-soluble, add activated carbon adsorption to remove out impurity, acidifying becomes Isosorbide-5-Nitrae-diamino-2 again, 3-dicarboximide; Filtration washing is neutral to pH, obtains Isosorbide-5-Nitrae-diamino-2,3-dicarboximide anthraquinone wet product, and these Isosorbide-5-Nitrae-diamino-2,3-dicarboximide anthraquinone wet product can be directly used in following condensation reaction.
At the enamel still of 5000L, put into 2000kg water, open and stir, add the wet product 1 of having got ready, 4-diamino-2,3-dicarboximide anthraquinone (450kg gives money as a gift), throws and finishes, add and get γ-methoxy propanamine 400kg ready, build kettle cover, stir half an hour, be warming up to 100 ℃, still internal pressure is 0.12MPa, is incubated 6 hours, then be cooled to 60 ℃, filter, filter the mother liquor obtaining and be collected in mother liquor tank, filter cake is washed to neutrality, obtains Disperse Blue-60.
Embodiment 2:
At the enamel still of 5000L, put into after embodiment 1 condensation reaction completes and filter and obtain mother liquor 2000kg, open and stir, add the wet product 1 of having got ready, 4-diamino-2,3-dicarboximide anthraquinone (450kg gives money as a gift), throws and finishes, and adds and gets γ-methoxy propanamine 150kg ready, build kettle cover, stir half an hour, be warming up to 102 ℃, reaction pressure is 0.13MPa, be incubated 6 hours, then be cooled to 60 ℃, filter, filter the mother liquor obtaining and be collected in mother liquor tank, filter cake is washed to neutrality, obtains Disperse Blue-60.
Embodiment 3:
At the enamel still of 5000L, put into after embodiment 2 condensation reactions complete and filter and obtain mother liquor 1500kg, water 500kg, open and stir, add wet product Isosorbide-5-Nitrae-diamino-2 of having got ready, 3-dicarboximide anthraquinone (450kg gives money as a gift), throw and finish, add and get γ-methoxy propanamine 160kg ready, build pot cover, stir half an hour, be warming up to 95 ℃, reaction pressure is 0.11MPa, is incubated 6 hours, is then cooled to 60 ℃, filter, the mother liquor that filtration obtains is collected in mother liquor tank, and filter cake is washed to neutrality, obtains Disperse Blue-60.
Embodiment 4:
At the enamel still of 5000L, put into after embodiment 3 condensation reactions complete and filter and obtain mother liquor 2500kg, open and stir, add the wet product 1 of having got ready, 4-diamino-2,3-dicarboximide anthraquinone (450kg gives money as a gift), throws and finishes, add and get γ-methoxy propanamine 130kg ready, build pot cover, stir half an hour, be warming up to 95 ℃, reaction pressure is 0.09MPa, is incubated 6 hours, then be cooled to 60 ℃, filter, filter the mother liquor obtaining and be collected in mother liquor tank, filter cake is washed to neutrality, obtains Disperse Blue-60.
Embodiment 5:
At the enamel still of 5000L, put into after embodiment 4 condensation reactions complete and filter and obtain mother liquor 2000kg, open and stir, add the wet product 1 of having got ready, 4-diamino-2,3-dicarboximide anthraquinone (450kg gives money as a gift), throws and finishes, add and get γ-methoxy propanamine 145kg ready, build pot cover, stir half an hour, be warming up to 95 ℃, reaction pressure is 0.14MPa, is incubated 6 hours, then be cooled to 60 ℃, filter, filter the mother liquor obtaining and be collected in mother liquor tank, filter cake is washed to neutrality, obtains Disperse Blue-60.
Comparative example 1:
At the enamel still of 5000L, put into γ-methoxy propanamine 400kg, dehydrated alcohol 1200L, opens and stirs, add wet product Isosorbide-5-Nitrae-diamino-2 of having got ready, 3-dicarboximide anthraquinone (450kg gives money as a gift), throw and finish, first-class pot cover, opens reflux exchanger into and out of water valve, be warming up to 75 ℃, back flow reaction 6 hours, is then cooled to 60 ℃, filter, filtration obtains mother liquor again by Distillation recovery ethanol and γ-methoxy propanamine, and filter cake is washed to neutrality, prepares Disperse Blue-60.
Embodiment 6:
At the enamel still of 5000L, put into 2000kg water, open and stir, add the wet product 1 of having got ready, 4-diamino-2,3-dicarboximide anthraquinone (450kg gives money as a gift), throws and finishes, add and get γ-ethoxy propylamine 460kg ready, build pot cover, stir half an hour, be warming up to 100 ℃, pot inner pressure is 0.12MPa, is incubated 6 hours, then be cooled to 60 ℃, filter, filter the mother liquor obtaining and be collected in mother liquor tank, filter cake is washed to neutrality, prepares the homologue of Disperse Blue-60.
Embodiment 7:
At the enamel still of 5000L, put into after embodiment 6 condensation reactions complete and filter and obtain mother liquor 2000kg, open and stir, add the wet product 1 of having got ready, 4-diamino-2,3-dicarboximide anthraquinone (450kg gives money as a gift), throws and finishes, and adds and gets γ-ethoxy propylamine 160kg ready, build pot cover, stir half an hour, be warming up to 103 ℃, reaction pressure is 0.15MPa, be incubated 5.5 hours, then be cooled to 60 ℃, filter, filter the mother liquor obtaining and be collected in mother liquor tank, filter cake is washed to neutrality, prepares the homologue of Disperse Blue-60.
Embodiment 8:
At the enamel still of 5000L, put into after embodiment 7 condensation reactions complete and filter and obtain mother liquor 2500kg, open and stir, add the wet product 1 of having got ready, 4-diamino-2,3-dicarboximide anthraquinone (450kg gives money as a gift), throws and finishes, and adds and gets γ-ethoxy propylamine 140kg ready, build pot cover, stir half an hour, be warming up to 95 ℃, reaction pressure is 0.08MPa, be incubated 6 hours, then be cooled to 60 ℃, filter, filter the mother liquor obtaining and be collected in mother liquor tank, filter cake is washed to neutrality, prepares the homologue of Disperse Blue-60.
Embodiment 9:
At the enamel still of 5000L, put into after embodiment 8 condensation reactions complete and filter and obtain mother liquor 2000kg, open and stir, add the wet product 1 of having got ready, 4-diamino-2,3-dicarboximide anthraquinone (450kg gives money as a gift), throws and finishes, and adds and gets γ-ethoxy propylamine 150kg ready, build pot cover, stir half an hour, be warming up to 105 ℃, reaction pressure is 0.15MPa, be incubated 6 hours, then be cooled to 60 ℃, filter, filter the mother liquor obtaining and be collected in mother liquor tank, filter cake is washed to neutrality, prepares the homologue of Disperse Blue-60.
Embodiment 10:
At the enamel still of 5000L, put into after embodiment 9 condensation reactions complete and filter and obtain mother liquor 1800kg, open and stir, add the wet product 1 of having got ready, 4-diamino-2,3-dicarboximide anthraquinone (450kg gives money as a gift), throws and finishes, and adds and gets γ-ethoxy propylamine 170kg ready, build pot cover, stir half an hour, be warming up to 100 ℃, reaction pressure is 0.11MPa, be incubated 6 hours, then be cooled to 60 ℃, filter, filter the mother liquor obtaining and be collected in mother liquor tank, filter cake is washed to neutrality, prepares the homologue of Disperse Blue-60.
Disperse Blue-60 and homologue thereof that embodiment 1～10 and comparative example 1 are prepared carry out analytical results as table 1.Reacted mother liquor is meeting under the condition of follow-up condensation reaction, and remaining mother liquor can reclaim γ-alkoxy propyl amine after distillation, and as the raw material use of follow-up condensation reaction, mother liquor described herein is the mother liquor that needs distillation in table 1.
Table 1
Above-mentioned staining power is to be the staining power that standard substance are surveyed with respect to 200% commercialization EX-SF DISPERSE BLUE EX-SF 300, and concrete measuring method is GB/T2394-200.
From above embodiment and comparative example, can draw, process modification by the present invention to Disperse Blue-60, guaranteeing that product staining power is greater than 472, coloured light is in approximate-micro-red situation, can improve the yield (product filter cake is given money as a gift and is greater than 470kg) of product on the one hand, reducing raw material consumption reduces raw material consumption (consumption of every batch of γ-methoxy propanamine is less than 200kg (γ-methoxy propanamine of throwing in comparative example is 400kg under the condition of mother liquor reuse, by distillation, can steam 200kg, actual every batch of consumption γ-methoxy propanamine is 190kg).Can reduce on the other hand the energy expenditure that must drop into due to distillation mother liquor, realize energy-saving and emission-reduction, the object of cleaner production, recycling economy, economic benefit and environmental benefit are remarkable.
Claims (1)
1. a preparation method for Disperse Blue-60, comprising:
In in sulphonation kettle, add 2000kg orthodichlorobenzene, be warming up to 120 ℃ of dehydrations, be cooled to 50 ℃ and drop into 250kg 1,4-diamino-anthraquinone, drips 480kg chlorsulfonic acid at 50 ~ 55 ℃ and carries out sulfonation reaction, finishes, slowly be warming up to 140 ℃, 140 ~ 145 ℃ of insulation reaction 7 hours; After sulfonation completes, be cooled to 70 ℃, in still kettle with adding water 3000L, the sulfonation material that suction has been got ready, then use liquid adjusting PH with base to 8, reaction distillation, distillation is finished, and filters; Filtrate proceeds in cyaniding pot, adds 30% sodium cyanide solution 500kg, then adds reserve salt to carry out cyaniding, and dripping dilute sulphuric acid control pH value is 9.0-9.5, and cyanogenation temperature is 98 ℃; Cyaniding is finished, and in cyaniding product, adds sodium thiosulfate to remove poison, and filtration washing, to neutrality, is dried; Add vitriol oil 500L, at 65 ℃, add dry Isosorbide-5-Nitrae-diamino-2 being no more than, 3-dicyan anthraquinone 150kg, 60 ~ 75 ℃ of insulation reaction, reaction is finished, then suction dilution pot, being diluted with water to acidity is 20-23%, after filtering, washing, then add 50-70kg sodium hydroxide, generate suitable sodium salt entirely water-soluble, add activated carbon adsorption to remove out impurity, then acidifying becomes 1,4-diamino-2,3-dicarboximide; Filtration washing is neutral to pH, obtains Isosorbide-5-Nitrae-diamino-2,3-dicarboximide anthraquinone wet product, and these Isosorbide-5-Nitrae-diamino-2,3-dicarboximide anthraquinone wet product is directly used in following condensation reaction;
At the enamel still of 5000L, put into 2000kg water, open and stir, add the wet product 1 of having got ready, 4-diamino-2,3-dicarboximide anthraquinone, 450kg gives money as a gift, throw and finish, add and get γ-methoxy propanamine 400kg ready, build kettle cover, stir half an hour, be warming up to 100 ℃, still internal pressure is 0.12MPa, be incubated 6 hours, be then cooled to 60 ℃, filter, the mother liquor that filtration obtains is collected in mother liquor tank, and filter cake is washed to neutrality, obtains Disperse Blue-60.
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| CN102199364B (en) * | 2011-03-11 | 2014-04-09 | 河南洛染股份有限公司 | Blue temporary water-soluble disperse dye, preparation method thereof and application thereof |
| CN102212029B (en) * | 2011-04-20 | 2012-11-21 | 江苏亚邦染料股份有限公司 | Synthesis method of disperse blue 60 intermediate |
| CN103242208B (en) * | 2013-05-03 | 2015-01-07 | 盐城市瓯华化学工业有限公司 | Process for preparing 1, 4-diamino-anthraquinone-2, 3-disulfonic acid by nicotinic acid method |
| CN103497142B (en) * | 2013-10-09 | 2015-10-14 | 江苏和利瑞科技发展有限公司 | The preparation method of Disperse Blue-60 and/or its homologue |
| CN109096789A (en) * | 2018-07-20 | 2018-12-28 | 江苏华尔化工有限公司 | A kind of No. 60 blue synthesis in water technique |
| 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 |
| CN112500718A (en) * | 2020-09-21 | 2021-03-16 | 浙江恩盛染料化工有限公司 | Resource utilization method of C.I. disperse blue 60 condensation reclaimed material |
| CN112795207A (en) * | 2020-12-19 | 2021-05-14 | 浙江恩盛染料化工有限公司 | Post-treatment method of disperse blue 60 |
| CN113930085B (en) * | 2021-11-08 | 2023-08-08 | 浙江万丰化工股份有限公司 | Sun-proof anthraquinone disperse dye and preparation method thereof |
| 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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| CN100543012C (en) * | 2006-12-28 | 2009-09-23 | 江苏亚邦染料股份有限公司 | Preparation 1,4-diamino-2, the method for 3-dicyan anthraquinone |
| CN101130640A (en) * | 2007-08-13 | 2008-02-27 | 江苏亚邦染料股份有限公司 | Improved technique for synthesizing dispersion blue 60 |
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