CN102295837B - Preparation method for disperse yellow dye - Google Patents
Preparation method for disperse yellow dye Download PDFInfo
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- CN102295837B CN102295837B CN201110148288.3A CN201110148288A CN102295837B CN 102295837 B CN102295837 B CN 102295837B CN 201110148288 A CN201110148288 A CN 201110148288A CN 102295837 B CN102295837 B CN 102295837B
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- Prior art keywords
- disperse yellow
- carboxylic acid
- water
- phthalic anhydride
- filter cake
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- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000001043 yellow dye Substances 0.000 title claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000012065 filter cake Substances 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 7
- 238000006482 condensation reaction Methods 0.000 claims abstract description 6
- 238000010792 warming Methods 0.000 claims description 9
- 238000009413 insulation Methods 0.000 claims description 8
- CXDPUSMFYPQXCV-UHFFFAOYSA-N (2,6-dichlorophenyl)boronic acid Chemical compound OB(O)C1=C(Cl)C=CC=C1Cl CXDPUSMFYPQXCV-UHFFFAOYSA-N 0.000 claims description 5
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 5
- 238000002386 leaching Methods 0.000 claims description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract description 11
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract description 11
- 238000009833 condensation Methods 0.000 abstract description 6
- 230000005494 condensation Effects 0.000 abstract description 6
- 239000003960 organic solvent Substances 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000002351 wastewater Substances 0.000 abstract description 5
- 238000001816 cooling Methods 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000004898 kneading Methods 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000007599 discharging Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- 238000004043 dyeing Methods 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- FDTLQXNAPKJJAM-UHFFFAOYSA-N 2-(3-hydroxyquinolin-2-yl)indene-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C1=NC2=CC=CC=C2C=C1O FDTLQXNAPKJJAM-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 1
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 1
- RTZYVAQWQXPIAC-UHFFFAOYSA-N 4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound C1=CC(O)=CC=C1N=NC1=CC=C(N=NC=2C=CC=CC=2)C=C1 RTZYVAQWQXPIAC-UHFFFAOYSA-N 0.000 description 1
- 229920004934 Dacron® Polymers 0.000 description 1
- 229920001410 Microfiber Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- 229920004935 Trevira® Polymers 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention provides a preparation method for a disperse yellow E-3G. The method comprises: adding 4-carboxylic acid and phthalic anhydride to a kneading device, starting the stirring, heating to a temperature of 170-200 DEG C, holding the temperature and carrying out condensation reaction until no gas is released; cooling to the temperature less than 60 DEG C after completing the reaction, then transferring the condensation compound in the kneading devices into water, then heating to the temperature of 90-100 DEG C, then holding for 1-3 h; carrying out filtering, and washing the filter cake through the water to obtain the filter cake of the disperse yellow dye. With the present invention, during the preparation process for the disperse yellow E-3G, the raw materials such as the 4-carboxylic acid and the phthalic anhydride are directly subjected to the condensation reaction in the kneading device, such that the disadvantage of the requirement of adding a plurality of an organic solvent DMF in the existing condensation process is overcome, the feeding ratio of the 4-carboxylic acid to the phthalic anhydride is reduced, such that the raw material consuming is substantially reduced, the production cost is saved, the waste water discharging is reduced; the method has characteristics of simple process, convenient operation and suitability to popularization and application; significant economic benefits and social benefits are provided.
Description
(1) technical field
The present invention relates to a kind of preparation method of quinoline disperse yellow dye.
(2) background technology
DISPERSE YELLOW E-3G (C.I. DISPERSE YELLOW 54) 2-(3-hydroxyl-2-quinolyl) indane-1,3-diketone, its structural formula is as follows:
DISPERSE YELLOW E-3G is mainly used in dyeing or the stamp of terylene, also can be used for dyeing or stamp that polyamide fibre, vinegar fiber and wash/wool blend are knitted etc., is also applicable to the dyeing of dacron ultrafine fiber.DISPERSE YELLOW E-3G belongs to E type high-quality bright yellow dispersed dye, while dyeing separately, light fastness reaches 6～7 grades, other performance all can reach 4～5 grades, it is Disperse Yellow RGFL (C.I. DISPERSE YELLOW 23, this dyestuff has good dyeing behavior, but owing to easily decomposing and producing carcinogenic aromatic amine under given conditions, can not meet the environmental requirement of increasingly stringent) best substitute.In addition, DISPERSE YELLOW E-3G can be combined into bright-coloured fruit green with DISPERSE BLUE 2BLN or bright blue S-GL, also can risk ash, shallow coffee to black tone with blue 3GE and Disperse Red 3B, and market demand amount is large.
The common synthetic method of DISPERSE YELLOW E-3G is: 2-methyl-3-hydroxyquinoline-4-carboxylic acid and Tetra hydro Phthalic anhydride are placed in to high boiling organic solvent (as the organic solvent such as trichlorobenzene, DMF) and mix, condensation reaction 8h at approximately 200 ℃, react rear cooling room temperature, filtered and obtain product.In the method, the usage quantity of high boiling organic solvent is larger, and follow-up need increase techniques such as reclaiming solvent, and have increased waste water; In addition, raw material phthalic anhydride consumption is also large, and having wasted resource has increased again waste water.
(3) summary of the invention
For overcoming above-mentioned deficiency, the invention provides the synthetic method of a kind of DISPERSE YELLOW E-3G, the method adopts kneader, do not need to use high boiling organic solvent, directly 4-carboxylic acid and phthalic anhydride are placed in to kneader and carry out condensation reaction, greatly reduce cost, reduce discharge of wastewater, there is significant economic benefit and social benefit.
The technical solution used in the present invention is:
A kind of structure is suc as formula the preparation method of the disperse yellow dye shown in (I), and described method comprises:
(1) 2-methyl-3-hydroxyquinoline-4-carboxylic acid (hereinafter to be referred as 4-carboxylic acid) and Tetra hydro Phthalic anhydride (hereinafter to be referred as phthalic anhydride) are added in kneader, open and stir, be warming up to 170～200 ℃, heat-preserving condensation reaction is to emitting without gas;
(2) after having reacted, reaction solution is cooled to below 60 ℃, the condenses in kneader is transferred in water, then be warming up to 90～100 ℃ of insulation 1～3h, filter with the removal of impurities of water washing filter cake, obtain the filter cake of disperse yellow dye shown in formula (I);
In described step (1) 2-methyl-3-hydroxyquinoline-4-carboxylic acid and Tetra hydro Phthalic anhydride molar ratio be preferably 1: 1.2～1.8.
Preferably, in described step (2), condenses is transferred in the water that quality is 2～4 times of described condenses quality, washing leaching cake water used is the hot water of 75～85 ℃.Conventionally be advisable in filter cake washing to washing lotion pH6～7.
Beneficial effect of the present invention is embodied in: in the preparation process of DISPERSE YELLOW E-3G, raw material 4-carboxylic acid and phthalic anhydride directly carry out condensation in kneader, abandon the process that former condensation operation need add a large amount of organic solvent DMF, and reduce the feed ratio of 4-carboxylic acid and phthalic anhydride, thereby the raw material consumption of greatly reducing, save production cost, also reduced discharge of wastewater; Technique is simple, easy to operate, suitable to be applied, and economic benefit and social benefit are remarkable.
(4) embodiment
Below in conjunction with specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in this:
Embodiment 1:
The phthalic anhydride of the 4-carboxylic acid dry product of 812g and 769.6g is dropped in the kneader of 4L, open and stir, slowly heat up, temperature of charge is controlled to 180～190 ℃, insulation reaction 2h, to without after Bubble formation, is cooled to 55 ℃, after material is cooling, this material is transferred in 4.8L water, is warming up to 90～95 ℃, insulation 1～2h, filter, with the hot wash filter cake of 80 ℃ to pH6.5.
Embodiment 2:
The phthalic anhydride of the 4-carboxylic acid dry product of 609g and 666g is dropped in the kneader of 4L, open and stir, slowly heat up, temperature of charge is controlled to 190～200 ℃, insulation reaction 2h, to without after Bubble formation, be cooled to room temperature, this material is transferred in 3L water, be warming up to 90～95 ℃, insulation 1～2h, filter, with the hot wash filter cake of 75 ℃ to pH6.5.
Comparative example 1:
The 4-carboxylic acid dry product of 260g, the phthalic anhydride of 568g and the DMF of 390L are dropped in condensation pot, kettle temperature is raised to 60 ℃ and opens stirring, continue to be warming up to 150～160 ℃, insulation reaction one hour, be more slowly warming up to 190～200 ℃ of insulation reaction 4 hours.Slowly putting into DMF780L makes temperature be down to 120～130 degree, stir one hour, material in condensation pot is put into cooling pan, start and stir, open chuck water coolant, suction filtration after material is cooled to 40 ℃ by continuation, after mother liquor is all drained, with the hot water of 60 ℃ of left and right, filter cake is washed till to pH6.5 again, finally reclaims the DMF in filtrate.
Application Example:
The filter cake that above-mentioned reaction is obtained, makes finished product by the commercialization treatment process of dispersed dye filter cake routine.Make slurries as added conventional dispersing auxiliary in toward filter cake after as Dispersant MF, NNO etc., water blending, the solid content of controlling slurries is 35～45% to be advisable, and grinding distribution is dry, makes finished product.
Respectively getting 0.5 gram of embodiment 1～2 and comparative example 1 reacts the finished product that the filter cake that obtains makes and is dispersed in 500 ml waters, after drawing 20 milliliters, mix with the water of 60 milliliters, adjusting dye bath pH with acetic acid is 5, being warming up to 70 ℃ puts into 2 grams of trevira simultaneously and dyes, in 30 minutes, be warmed up to 130 ℃ by 70 ℃, be incubated 30 minutes, while being cooled to 90 ℃, start sampling.Observe sample cloth coloured light, test its light fastness (xenon lamp), water-fastness, antifriction scrape along colour fastness to perspiration respectively by method definite in ISO105-B02, ISO105-CO3, ISO105 × 12 and ISO105-E04, result is as follows:
Above-mentioned experimental result shows, the DISPERSE YELLOW E-3G that adopts DISPERSE YELLOW E-3G that preparation method of the present invention makes and traditional method to prepare, and its dyeing colour fastness is substantially the same.
Claims (2)
1. a preparation method for the disperse yellow dye of structure as shown in formula I, described method comprises:
(1) 2-methyl-3-hydroxyquinoline-4-carboxylic acid and Tetra hydro Phthalic anhydride are added in kneader, open and stir, be warming up to 170～200 ℃, heat-preserving condensation reaction is to emitting without gas; 2-methyl-3-hydroxyquinoline-4-carboxylic acid and Tetra hydro Phthalic anhydride molar ratio are 1:1.2～1.8;
(2) after having reacted, reaction solution is cooled to below 60 ℃, the condenses in kneader is transferred in water, then be warming up to 90～100 ℃ of insulation 1～3h, filters with water washing filter cake, obtains the filter cake of described disperse yellow dye;
2. the method for claim 1, is characterized in that condenses being transferred in the water that quality is 2～4 times of described condenses quality in described step (2), and washing leaching cake water used is the hot water of 75～85 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110148288.3A CN102295837B (en) | 2011-06-02 | 2011-06-02 | Preparation method for disperse yellow dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110148288.3A CN102295837B (en) | 2011-06-02 | 2011-06-02 | Preparation method for disperse yellow dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102295837A CN102295837A (en) | 2011-12-28 |
| CN102295837B true CN102295837B (en) | 2014-06-04 |
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| CN201110148288.3A Expired - Fee Related CN102295837B (en) | 2011-06-02 | 2011-06-02 | Preparation method for disperse yellow dye |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104559315B (en) * | 2014-12-18 | 2016-09-14 | 江苏迪安化工有限公司 | Yellow mixed crystal type disperse dye |
| CN105669545A (en) * | 2016-03-15 | 2016-06-15 | 江苏华尔化工有限公司 | Preparation technology of dye disperse yellow 54# |
| CN109021607A (en) * | 2018-07-13 | 2018-12-18 | 常州大学 | A kind of production method of disperse yellow 54 |
| CN115850995B (en) * | 2022-12-09 | 2023-12-12 | 河北中化鑫宝化工科技有限公司 | Preparation method of solvent yellow 33 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2006022A (en) * | 1932-11-18 | 1935-06-25 | Gen Aniline Works Inc | Dyestuff of the quinophthalone series of good fastness to light |
| DE1229663B (en) * | 1964-06-27 | 1966-12-01 | Basf Ag | Process for the preparation of 4-bromo-3-hydroxyquinophthalone |
| US3872131A (en) * | 1971-10-01 | 1975-03-18 | Gaf Corp | Method of preparing quinophthalone dyes |
| DE19636880A1 (en) * | 1996-09-11 | 1998-03-12 | Bayer Ag | Process for the production of quinophthalones |
| CN102070523B (en) * | 2010-12-30 | 2013-07-10 | 浙江山峪染料化工有限公司 | Novel method for preparing 3-hydroxylquinaldine-4-carboxylic acid |
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- 2011-06-02 CN CN201110148288.3A patent/CN102295837B/en not_active Expired - Fee Related
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| CN102295837A (en) | 2011-12-28 |
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Granted publication date: 20140604 Termination date: 20200602 |