CN104277486A - Synthesis method of vat yellow 3RR - Google Patents
Synthesis method of vat yellow 3RR Download PDFInfo
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- CN104277486A CN104277486A CN201410468738.0A CN201410468738A CN104277486A CN 104277486 A CN104277486 A CN 104277486A CN 201410468738 A CN201410468738 A CN 201410468738A CN 104277486 A CN104277486 A CN 104277486A
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Abstract
The invention relates to the technical field of dyes and discloses a synthesis method of vat yellow 3RR. The synthesis method comprises the steps of condensation, water boiling, cyclization, isolation and distillation, oxidation, acidification, purification and the like. According to the synthesis method disclosed by the invention, 1, 5-diaminoanthraquinone and 1-chloroanthraquinone are taken as raw materials to prepare trianthraquinone amide, a crude vat yellow 3RR crude dye is further prepared under the action of aluminum trichloride and pyridine, and acidification and purification are performed by using sulfuric acid and sodium hydrosulfite. The synthesis process is simple, the product quality is good, the color is bright, and the brightness is high.
Description
Technical field
The present invention relates to technical field of dye, refer more particularly to the synthetic method of vat yellow 3RR.
Background technology
Vat dyes is that a veriety is numerous, chromatogram is complete, brightly painted high-grade dyestuff, is mainly used in the senior goods of cellulosic fibre and the dyeing of functional article and stamp, famous with the fastness of dyeing of its excellence.Because vat dyes is not containing azo-group, and it is as pigment type compound, also without special biochemical treatment problem, therefore also cannot replace completely with other dyestuffs at present concerning technical fabric.So although vat dyes manufactures complicated, still have stronger vitality, market development prospect is better.Due to the singularity that it is produced, more American-European traditional vat dyes big producing countries were limited to resource, manpower, environmental protection pressure and just successively stopped Dyestuff synthesis before 20 years, transferred to purchase former dyestuff to third world countries and carried out commercialization processing or direct purchase commodity dyestuff.Through the development of nearly decades, China, India etc. have become vat dyes producing country main in the world at present, and wherein the annual production of China's vat dyes has accounted for more than 50% of global vat dyes ultimate production.
Chinese patent 201210117440.6 discloses the production method of a kind of vat yellow 3RT, and preparation process is: by 1,5-dichloroanthraquinone, 1-aminoanthraquinone, soda ash, copper catalyst mixing and stirring, is warming up to 120 ~ 130 DEG C, dehydration, continues to be warming up to 210 ~ 260 DEG C, insulation; Be cooled to less than 60 DEG C, discharging, obtain imines crude product; Be added to the water by the crude product obtained, boil, filter after being down to room temperature, washing is to neutral, dry, obtains refining imines; Get pyridine, stir and heat up, in 70 ~ 115 DEG C, drop into aluminum chloride; Adjustment temperature to 80 ~ 115 DEG C, add refining imines, then are warming up to 140 ~ 160 DEG C, be incubated 1 ~ 5 hour; After insulation terminates, Distillation recovery pyridine; Filter, be washed to neutrality, obtain the thick dyestuff of vat yellow 3RT; Water intaking, throws the thick dyestuff of vat yellow 3RT, adds potassium permanganate, clorox after making beating; Be warming up to 90-95 DEG C, filter, be washed to neutrality, obtain vat yellow 3RT.This invention condensation solid state reaction replaces liquid phase reaction, not only eliminates the carcinogenic and bad courageous and upright of oil of mirbane, and saves the mass energy of distillation needed for oil of mirbane, decrease acidification step, saved production cost, improve quality product.But this invention synthetic method products obtained therefrom yield is low, and obtained vat yellow 3RT is of low quality, brightness is inadequate, and product easily produces the defect of color spot, color dot in dyeing course.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of simple to operate, and raw material is easy to get, the synthetic method of yield height vat yellow 3RR.
For solving the problems of the technologies described above, the present invention by the following technical solutions:
A synthetic method of vat yellow 3RR, is characterized in that, comprises following steps:
(1) condensation reaction: by weight, by 1,5-diamino-anthraquinone 70 ~ 150 parts, 1-chloro anthraquinone 150 ~ 250 parts, copper catalyst 5 ~ 10 parts, anhydrous sodium carbonate 78 ~ 84 parts adds in reactor, stir, be warming up to 100 ~ 120 DEG C, dewater after 1.5 ~ 4 hours, continue to be heated to 200 ~ 275 DEG C, be incubated after 4 ~ 4.5 hours, be cooled to 60 DEG C, and pulverize, discharging after 4 hours, weighs, and obtains thick three anthraquinone imines;
(2) poach reaction: thick three anthraquinone imines step (1) obtained add in 3000 parts of water, are warming up to 90 ~ 95 DEG C, are incubated after 1 hour, filter after being down to room temperature, washing is to neutral, dry, obtains refining three anthraquinone imines;
(3) ring-closure reaction: by weight, pyridine 1000 ~ 1400 parts is stirred and heats up, aluminum chloride 500 ~ 800 parts is slowly added at 70 ~ 135 DEG C, be incubated after 10 ~ 15 minutes, adjustment temperature to 90 ~ 125 DEG C, slowly add refining three anthraquinone imines 400 ~ 500 parts, be then warming up to 145 ~ 170 DEG C, the insulation 3 ~ 3.5 hours when refluxing;
(4) segregation distillation: 1000 ~ 1900 parts, sodium hydroxide is added to the water, preparation alkalescence end water, the material obtained after then step (3) being incubated adds in 4000 parts, alkalescence end water, and then heat up distillation, Distillation recovery pyridine; Distill complete, filter, be washed to alkalescence, obtain the former dyestuff of thick vat yellow 3RR;
(5) oxidizing reaction: fetch water 800 parts, stir the thick vat yellow 3RR crude product dyestuff 200 ~ 220 parts of lower input, pull an oar 1 hour, then add liquid caustic soda 200 ~ 500 parts, stir after 15 minutes, be warming up to 85 ~ 100 DEG C, add 100 ~ 180 parts, potassium permanganate and chlorine bleach liquor 5000 ~ 6000 parts, be down to room temperature, be washed to neutrality, discharging, obtains being oxidized filter cake;
(6) acidification: fetch water 500 parts, the oxidation filter cake that step (5) obtains is dropped under stirring, pull an oar after 2 hours, add 2000 parts of water, 150 ~ 250 parts, sulfuric acid and sub-50 ~ 150 parts, two sodium sulfate, be warming up to 90 ~ 95 DEG C, be incubated 1 hour, be down to room temperature, be washed to neutrality, discharging, obtains the former dyestuff of vat yellow 3RR.
Preferably, described step (1) copper catalyst is copper powder.
Preferably, described step (4) is washed to the pH value of alkalescence is 7-9.
Preferably, described step (5) oxidizing reaction is 90 ~ 95 DEG C.
Reaction scheme of the present invention is as follows:
The invention has the beneficial effects as follows:
The present invention uses 1,5-diamino-anthraquinone, 1-chloro anthraquinone are as the obtained three anthraquinone imines of raw material, then the obtained former dyestuff of thick vat yellow 3RR under the effect of aluminum chloride and pyridine, sulfuric acid and sub-two sodium sulfate are used to carry out acidifying purification, synthesis technique is simple, good product quality, bright in colour, brightness is high.
Embodiment
Below in conjunction with embodiment, technical scheme of the present invention is further described in detail.
Embodiment one:
(1) condensation reaction: by weight, by 1,5-diamino-anthraquinone 70kg, 1-chloro anthraquinone 150kg, copper catalyst 5kg, anhydrous sodium carbonate 78kg adds in reactor, stir, be warming up to 100 DEG C, dewater after 1.5 hours, continue to be heated to 200 DEG C, be incubated after 4 hours, be cooled to 60 DEG C, and pulverize, discharging after 4 hours, weighs, and obtains thick three anthraquinone imines;
(2) poach reaction: thick three anthraquinone imines step (1) obtained add in 3000L water, are warming up to 90 DEG C, are incubated after 1 hour, filter after being down to room temperature, washing is to neutral, dry, obtains refining three anthraquinone imines;
(3) ring-closure reaction: by weight, stirs pyridine 1000kg and heats up, at 70 DEG C, slowly add aluminum chloride 500kg, be incubated after 10 minutes, adjustment temperature to 90 DEG C, slowly adds refining three anthraquinone imines 400kg, then 145 DEG C are warming up to, the insulation 3 hours when refluxing;
(4) segregation distillation: sodium hydroxide 1000kg is added to the water, preparation alkalescence end water, the material obtained after then step (3) being incubated adds in alkalescence end water 4000L, and then heat up distillation, Distillation recovery pyridine 986kg; Distill complete, filter, being washed to pH value is 7, obtains the former dyestuff of thick vat yellow 3RR;
(5) oxidizing reaction: water intaking 800L, stir the thick vat yellow 3RR crude product dyestuff 200kg of lower input, pull an oar 1 hour, then add liquid caustic soda 200kg, stir after 15 minutes, be warming up to 85 DEG C, add potassium permanganate 100kg and chlorine bleach liquor 5000kg, be incubated after 4 hours, be down to room temperature, be washed to neutrality, discharging, obtain being oxidized filter cake;
(6) acidification: water intaking 500L, the oxidation filter cake that step (5) obtains is dropped under stirring, pull an oar after 2 hours, add 2000L water, sulfuric acid 150kg and sub-two sodium sulfate 50kg, be warming up to 90 DEG C, be incubated 1 hour, be down to room temperature, be washed to neutrality, discharging, obtains the former dyestuff 188kg of vat yellow 3RR.
Embodiment two:
(1) condensation reaction: by weight, by 1,5-diamino-anthraquinone 150kg, 1-chloro anthraquinone 250kg, copper catalyst 10kg, anhydrous sodium carbonate 84kg adds in reactor, stir, be warming up to 120 DEG C, dewater after 4 hours, continue to be heated to 275 DEG C, be incubated after 4.5 hours, be cooled to 60 DEG C, and pulverize, discharging after 4 hours, weighs, and obtains thick three anthraquinone imines;
(2) poach reaction: thick three anthraquinone imines step (1) obtained add in 3000L water, are warming up to 95 DEG C, are incubated after 1 hour, filter after being down to room temperature, washing is to neutral, dry, obtains refining three anthraquinone imines;
(3) ring-closure reaction: by weight, pyridine 1400kg is stirred and heats up, aluminum chloride 800kg is slowly added at 135 DEG C, be incubated after 15 minutes, adjustment temperature to 125 DEG C, slowly add refining three anthraquinone imines 500kg, be then warming up to 170 DEG C, the insulation 3.5 hours when refluxing;
(4) segregation distillation: sodium hydroxide 1900kg is added to the water, preparation alkalescence end water, the material obtained after then step (3) being incubated adds in alkalescence end water 4000L, and then heat up distillation, Distillation recovery pyridine 1360kg; Distill complete, filter, being washed to pH value is 9, obtains the former dyestuff of thick vat yellow 3RR;
(5) oxidizing reaction: water intaking 800L, stir the thick vat yellow 3RR crude product dyestuff 220kg of lower input, pull an oar 1 hour, then add liquid caustic soda 500kg, stir after 15 minutes, be warming up to 100 DEG C, add potassium permanganate 180kg and chlorine bleach liquor 6000kg, be incubated after 6 hours, be down to room temperature, be washed to neutrality, discharging, obtain being oxidized filter cake;
(6) acidification: water intaking 500kg, the oxidation filter cake that step (5) obtains is dropped under stirring, pull an oar after 2 hours, add 2000L water, sulfuric acid 250kg and sub-two sodium sulfate 150kg, be warming up to 95 DEG C, be incubated 1 hour, be down to room temperature, be washed to neutrality, discharging, obtains the former dyestuff 212kg of vat yellow 3RR.
Embodiment three:
(1) condensation reaction: by weight, by 1,5-diamino-anthraquinone 100kg, 1-chloro anthraquinone 200kg, copper catalyst 8kg, anhydrous sodium carbonate 80kg adds in reactor, stir, be warming up to 110 DEG C, dewater after 3 hours, continue to be heated to 250 DEG C, be incubated after 4.3 hours, be cooled to 60 DEG C, and pulverize, discharging after 4 hours, weighs, and obtains thick three anthraquinone imines;
(2) poach reaction: thick three anthraquinone imines step (1) obtained add in 3000L water, are warming up to 92 DEG C, are incubated after 1 hour, filter after being down to room temperature, washing is to neutral, dry, obtains refining three anthraquinone imines;
(3) ring-closure reaction: by weight, pyridine 1200kg is stirred and heats up, aluminum chloride 600kg is slowly added at 100 DEG C, be incubated after 13 minutes, adjustment temperature to 100 DEG C, slowly add refining three anthraquinone imines 450kg, be then warming up to 150 DEG C, the insulation 3.2 hours when refluxing;
(4) segregation distillation: sodium hydroxide 1500kg is added to the water, preparation alkalescence end water, the material obtained after then step (3) being incubated adds in alkalescence end water 4000L, and then heat up distillation, Distillation recovery pyridine 1490kg; Distill complete, filter, being washed to pH value is 8, obtains the former dyestuff of thick vat yellow 3RR;
(5) oxidizing reaction: water intaking 800L, stir the thick vat yellow 3RR crude product dyestuff 210kg of lower input, pull an oar 1 hour, then add liquid caustic soda 400kg, stir after 15 minutes, be warming up to 90 DEG C, add potassium permanganate 150kg and chlorine bleach liquor 5500kg, be incubated after 5 hours, be down to room temperature, be washed to neutrality, discharging, obtain being oxidized filter cake;
(6) acidification: water intaking 500L, the oxidation filter cake that step (5) obtains is dropped under stirring, pull an oar after 2 hours, add 2000L water, sulfuric acid 200kg and sub-two sodium sulfate 100kg, be warming up to 93 DEG C, be incubated 1 hour, be down to room temperature, be washed to neutrality, discharging, obtains the former dyestuff 200.5kg of vat yellow 3RR.
Embodiment four:
(1) condensation reaction: by weight, by 1,5-diamino-anthraquinone 120kg, 1-chloro anthraquinone 220kg, copper catalyst 8kg, anhydrous sodium carbonate 82kg adds in reactor, stir, be warming up to 115 DEG C, dewater after 2 hours, continue to be heated to 260 DEG C, be incubated after 4.4 hours, be cooled to 60 DEG C, and pulverize, discharging after 4 hours, weighs, and obtains thick three anthraquinone imines;
(2) poach reaction: thick three anthraquinone imines step (1) obtained add in 3000L water, are warming up to 92 DEG C, are incubated after 1 hour, filter after being down to room temperature, washing is to neutral, dry, obtains refining three anthraquinone imines;
(3) ring-closure reaction: by weight, pyridine 1300kg is stirred and heats up, aluminum chloride 700kg is slowly added at 120 DEG C, be incubated after 14 minutes, adjustment temperature to 120 DEG C, slowly add refining three anthraquinone imines 500kg, be then warming up to 160 DEG C, the insulation 3.1 hours when refluxing;
(4) segregation distillation: sodium hydroxide 1700kg is added to the water, preparation alkalescence end water, the material obtained after then step (3) being incubated adds in alkalescence end water 4000L, and then heat up distillation, Distillation recovery pyridine 1295kg; Distill complete, filter, being washed to pH value is 8, obtains the former dyestuff of thick vat yellow 3RR;
(5) oxidizing reaction: water intaking 800L, stir the thick vat yellow 3RR crude product dyestuff 205kg of lower input, pull an oar 1 hour, then add liquid caustic soda 300kg, stir after 15 minutes, be warming up to 95 DEG C, add potassium permanganate 160kg and chlorine bleach liquor 5000kg, be incubated after 5 hours, be down to room temperature, be washed to neutrality, discharging, obtain being oxidized filter cake;
(6) acidification: water intaking 500L, the oxidation filter cake that step (5) obtains is dropped under stirring, pull an oar after 2 hours, add 2000L water, sulfuric acid 180kg and sub-two sodium sulfate 120kg, be warming up to 92 DEG C, be incubated 1 hour, be down to room temperature, be washed to neutrality, discharging, obtains the former dyestuff 199.8kg of vat yellow 3RR.
Product primary quality measure of the present invention:
| Index name | Index |
| Intensity (ratios for standard substance) point | 100±3 |
| Coloured light (with standard substance ratio) | Approximate ~ microstage |
| Outward appearance | Reddish-brown uniform powder or particle |
| Moisture/% | ≤9 |
| Diffusion/level | ≥4 |
| Copper content/ppm | ≤500 |
| Iron level/ppm | ≤500 |
| Particle fineness (> 2 μm of particles) is individual | ≤3 |
The fastness of dyeing of product of the present invention on cotton fabric:
It should be noted last that, above embodiment is only in order to illustrate technical scheme of the present invention and unrestricted, although with reference to preferred embodiment to invention has been detailed description, those of ordinary skill in the art is to be understood that, can modify to technical scheme of the present invention or equivalent replacement, and not departing from the spirit and scope of technical solution of the present invention, it all should be encompassed in the middle of right of the present invention.
Claims (4)
1. a synthetic method of vat yellow 3RR, is characterized in that, comprises following steps:
(1) condensation reaction: by weight, by 1,5-diamino-anthraquinone 70 ~ 150 parts, 1-chloro anthraquinone 150 ~ 250 parts, copper catalyst 5 ~ 10 parts, anhydrous sodium carbonate 78 ~ 84 parts adds in reactor, stir, be warming up to 100 ~ 120 DEG C, dewater after 1.5 ~ 4 hours, continue to be heated to 200 ~ 275 DEG C, be incubated after 4 ~ 4.5 hours, be cooled to 60 DEG C, and pulverize, discharging after 4 hours, weighs, and obtains thick three anthraquinone imines;
(2) poach reaction: thick three anthraquinone imines step (1) obtained add in 3000 parts of water, are warming up to 90 ~ 95 DEG C, are incubated after 1 hour, filter after being down to room temperature, washing is to neutral, dry, obtains refining three anthraquinone imines;
(3) ring-closure reaction: by weight, pyridine 1000 ~ 1400 parts is stirred and heats up, aluminum chloride 500 ~ 800 parts is slowly added at 70 ~ 135 DEG C, be incubated after 10 ~ 15 minutes, adjustment temperature to 90 ~ 125 DEG C, slowly add refining three anthraquinone imines 400 ~ 500 parts, be then warming up to 145 ~ 170 DEG C, the insulation 3 ~ 3.5 hours when refluxing;
(4) segregation distillation: 1000 ~ 1900 parts, sodium hydroxide is added to the water, preparation alkalescence end water, the material obtained after then step (3) being incubated adds in 4000 parts, alkalescence end water, and then heat up distillation, Distillation recovery pyridine; Distill complete, filter, be washed to alkalescence, obtain the former dyestuff of thick vat yellow 3RR;
(5) oxidizing reaction: fetch water 800 parts, stir the thick vat yellow 3RR crude product dyestuff 200 ~ 220 parts of lower input, pull an oar 1 hour, then add liquid caustic soda 200 ~ 500 parts, stir after 15 minutes, be warming up to 85 ~ 100 DEG C, add 100 ~ 180 parts, potassium permanganate and chlorine bleach liquor 5000 ~ 6000 parts, be incubated after 4 ~ 6 hours, be down to room temperature, be washed to neutrality, discharging, obtain being oxidized filter cake;
(6) acidification: fetch water 500 parts, the oxidation filter cake that step (5) obtains is dropped under stirring, pull an oar after 2 hours, add 2000 parts of water, 150 ~ 250 parts, sulfuric acid and sub-50 ~ 150 parts, two sodium sulfate, be warming up to 90 ~ 95 DEG C, be incubated 1 hour, be down to room temperature, be washed to neutrality, discharging, obtains the former dyestuff of vat yellow 3RR.
2. the synthetic method of vat yellow 3RR according to claim 1, is characterized in that, described step (1) copper catalyst is copper powder.
3. the synthetic method of vat yellow 3RR according to claim 1, is characterized in that, the pH value that described step (4) is washed to alkalescence is 7-9.
4. the synthetic method of vat yellow 3RR according to claim 1, is characterized in that, described step (5) oxidizing reaction is 90 ~ 95 DEG C.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106317955A (en) * | 2016-07-26 | 2017-01-11 | 萧县凯奇化工科技有限公司 | Brown reduction dye and preparation method thereof |
| CN111072658A (en) * | 2019-12-26 | 2020-04-28 | 江苏亚邦染料股份有限公司 | Method for synthesizing vat black 25 |
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| GB190915846A (en) * | 1909-07-07 | 1910-06-23 | Philip Arthur Newton | Manufacture and Production of New Dyestuffs of the Anthracene Series. |
| GB238523A (en) * | 1924-08-13 | 1926-09-02 | Hoechst Ag | Manufacture of vat dyestuffs of the anthracene series |
| GB856804A (en) * | 1955-12-30 | 1960-12-21 | Gen Aniline & Film Corp | Heterocyclic vat dyestuffs |
| GB1222331A (en) * | 1968-01-02 | 1971-02-10 | Vyzk Ustav Organ Syntez | Process for carbazolising anthrimides in the preparation of diphthaloylcarbazols |
| US4349478A (en) * | 1980-10-14 | 1982-09-14 | Ciba-Geigy Ag | Process for the carbazolation of anthrimides |
| US20060010620A1 (en) * | 2002-08-24 | 2006-01-19 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Textile spun-dyed fiber material and use thereof for producing camouflage articles |
| US20070180630A1 (en) * | 2004-03-26 | 2007-08-09 | Wella Ag | Hair colorants with vat dyes |
| CN102660131A (en) * | 2012-04-19 | 2012-09-12 | 徐州开达精细化工有限公司 | Method for producing vat yellow 3RT |
-
2014
- 2014-09-15 CN CN201410468738.0A patent/CN104277486A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB190915846A (en) * | 1909-07-07 | 1910-06-23 | Philip Arthur Newton | Manufacture and Production of New Dyestuffs of the Anthracene Series. |
| GB238523A (en) * | 1924-08-13 | 1926-09-02 | Hoechst Ag | Manufacture of vat dyestuffs of the anthracene series |
| GB856804A (en) * | 1955-12-30 | 1960-12-21 | Gen Aniline & Film Corp | Heterocyclic vat dyestuffs |
| GB1222331A (en) * | 1968-01-02 | 1971-02-10 | Vyzk Ustav Organ Syntez | Process for carbazolising anthrimides in the preparation of diphthaloylcarbazols |
| US4349478A (en) * | 1980-10-14 | 1982-09-14 | Ciba-Geigy Ag | Process for the carbazolation of anthrimides |
| US20060010620A1 (en) * | 2002-08-24 | 2006-01-19 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Textile spun-dyed fiber material and use thereof for producing camouflage articles |
| US20070180630A1 (en) * | 2004-03-26 | 2007-08-09 | Wella Ag | Hair colorants with vat dyes |
| CN102660131A (en) * | 2012-04-19 | 2012-09-12 | 徐州开达精细化工有限公司 | Method for producing vat yellow 3RT |
Non-Patent Citations (1)
| Title |
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| 何海兰: "《精细化工产品手册 染料》", 31 October 2004, article "还原黄3RT" * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106317955A (en) * | 2016-07-26 | 2017-01-11 | 萧县凯奇化工科技有限公司 | Brown reduction dye and preparation method thereof |
| CN111072658A (en) * | 2019-12-26 | 2020-04-28 | 江苏亚邦染料股份有限公司 | Method for synthesizing vat black 25 |
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