CN106748833B - A kind of preparation method of 63 dyestuff of solvent blue - Google Patents
A kind of preparation method of 63 dyestuff of solvent blue Download PDFInfo
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- CN106748833B CN106748833B CN201611074318.XA CN201611074318A CN106748833B CN 106748833 B CN106748833 B CN 106748833B CN 201611074318 A CN201611074318 A CN 201611074318A CN 106748833 B CN106748833 B CN 106748833B
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- toluidine
- methylamino
- bromoanthraquinone
- solvent blue
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- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000000975 dye Substances 0.000 title description 10
- 239000002904 solvent Substances 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 39
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000003756 stirring Methods 0.000 claims abstract description 14
- GBAJQXFGDKEDBM-UHFFFAOYSA-N 1-(methylamino)-4-(3-methylanilino)anthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(NC)=CC=C1NC1=CC=CC(C)=C1 GBAJQXFGDKEDBM-UHFFFAOYSA-N 0.000 claims abstract description 13
- IIPRUQZTMZETSL-UHFFFAOYSA-N 1-bromo-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC=C2NC IIPRUQZTMZETSL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 150000001879 copper Chemical class 0.000 claims abstract description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 7
- 238000002955 isolation Methods 0.000 claims abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 6
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical group [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims 1
- 229910000000 metal hydroxide Inorganic materials 0.000 claims 1
- 150000004692 metal hydroxides Chemical class 0.000 claims 1
- 238000005406 washing Methods 0.000 abstract description 14
- 239000002351 wastewater Substances 0.000 abstract description 7
- 230000035484 reaction time Effects 0.000 abstract description 3
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract description 2
- 238000007086 side reaction Methods 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 10
- 238000001035 drying Methods 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/325—Dyes with no other substituents than the amino groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及一种溶剂蓝63染料的制备方法，它包括以下步骤：（a）向反应容器中加入间甲苯胺，在搅拌条件下依次加入1‑甲氨基‑4‑溴蒽醌、碱金属氢氧化物和铜盐，随后升温至100~130℃，反应4‑7小时至终点；所述1‑甲氨基‑4‑溴蒽醌、间甲苯胺、碱金属氢氧化物和铜盐的质量比为6：12~16：3~4：0.04~0.08；（b）将步骤（a）的产物降温至60~70℃，随后加入甲醇进行离析；搅拌后降温至30~50℃，经过滤、洗涤、烘干即可。得到的反应纯度高，副反应少，反应时间短；更重要的是产品结晶明显，易洗涤，生产洗涤废水量少。The invention relates to a preparation method of solvent blue 63 dye, which comprises the following steps: (a) adding m-toluidine into a reaction vessel, adding 1-methylamino-4-bromoanthraquinone and alkali metal hydrogen in sequence under stirring conditions Oxide and copper salt, then be heated to 100 ~ 130 ℃, react for 4-7 hours to the end; the mass ratio of the 1-methylamino-4-bromoanthraquinone, m-toluidine, alkali metal hydroxide and copper salt 6: 12~16: 3~4: 0.04~0.08; (b) Cool the product of step (a) to 60~70°C, then add methanol for isolation; after stirring, cool down to 30~50°C, filter, Just wash and dry. The obtained reaction has high purity, less side reactions, and short reaction time; more importantly, the product has obvious crystallization, is easy to wash, and has less waste water for washing.
Description
技术领域technical field
本发明涉及一种染料的制备方法，具体涉及一种溶剂蓝63染料的制备方法。The invention relates to a method for preparing a dye, in particular to a method for preparing a solvent blue 63 dye.
背景技术Background technique
溶剂蓝63，中文名为：1-(甲基氨基)-4-[(3-甲基苯基)氨基]蒽醌，其分子式为：C22H18N2O2， CAS号为6408-50-0。现有溶剂蓝63，的生产工艺反应时间长，反应纯度低，生产用洗涤废水量大，容易对环境造成污染。Solvent Blue 63, the Chinese name is: 1-(methylamino)-4-[(3-methylphenyl)amino]anthraquinone, its molecular formula is: C 22 H 18 N 2 O 2 , and its CAS number is 6408- 50-0. The existing production process of solvent blue 63 has long reaction time, low reaction purity, large amount of washing wastewater for production, and is easy to cause pollution to the environment.
发明内容Contents of the invention
本发明目的是为了克服现有技术的不足而提供一种溶剂蓝63染料的制备方法。The object of the invention is to provide a kind of preparation method of solvent blue 63 dye in order to overcome the deficiencies in the prior art.
为达到上述目的，本发明所采用的技术方案为：一种溶剂蓝63染料的制备方法，它包括以下步骤：In order to achieve the above object, the technical scheme adopted in the present invention is: a kind of preparation method of solvent blue 63 dye, it comprises the following steps:
(a)向反应容器中加入间甲苯胺，在搅拌条件下依次加入1-甲氨基-4-溴蒽醌、碱金属氢氧化物和铜盐，随后升温至100～130℃，反应4-7小时至终点；所述1-甲氨基-4-溴蒽醌、间甲苯胺、碱金属氢氧化物和铜盐的质量比为6：12～16：3～4：0.04～0.08；(a) Add m-toluidine to the reaction vessel, add 1-methylamino-4-bromoanthraquinone, alkali metal hydroxide and copper salt in sequence under stirring, then raise the temperature to 100-130°C, and react 4-7 Hours to the end; the mass ratio of the 1-methylamino-4-bromoanthraquinone, m-toluidine, alkali metal hydroxide and copper salt is 6:12～16:3～4:0.04～0.08;
(b)将步骤(a)的产物降温至60～70℃，随后加入甲醇进行离析；搅拌后降温至30～50℃，经过滤、洗涤、烘干即可。(b) Cooling the product of step (a) to 60-70°C, then adding methanol for isolation; cooling to 30-50°C after stirring, filtering, washing and drying.
优化地，所述碱金属氢氧化物为氢氧化钠或氢氧化钾，所述硫酸铜。Optimally, the alkali metal hydroxide is sodium hydroxide or potassium hydroxide, and the copper sulfate.
优化地，所述间甲苯胺和所述甲醇的比例为3g：5～7.5ml。Optimally, the ratio of the m-toluidine to the methanol is 3g:5-7.5ml.
由于上述技术方案运用，本发明与现有技术相比具有下列优点：本发明溶剂蓝63染料的制备方法，通过采用间甲苯胺为溶剂，与1-甲氨基-4-溴蒽醌、碱金属氢氧化物和铜盐等按一定比例和特定温度条件下进行反应，得到的反应纯度高，副反应少，反应时间短；更重要的是产品结晶明显，易洗涤，生产洗涤废水量少。Due to the use of the above-mentioned technical scheme, the present invention has the following advantages compared with the prior art: the preparation method of solvent blue 63 dyestuff of the present invention, by adopting m-toluidine as solvent, with 1-methylamino-4-bromoanthraquinone, alkali metal Hydroxide and copper salt are reacted in a certain proportion and under specific temperature conditions, and the obtained reaction has high purity, less side reactions, and short reaction time; more importantly, the product has obvious crystallization, is easy to wash, and produces less washing wastewater.
具体实施方式Detailed ways
下面将结合对本发明优选实施方案进行详细说明。The preferred embodiments of the present invention will be described in detail below.
实施例1Example 1
本实施例提供一种溶剂蓝63染料的制备方法，它包括以下步骤：The present embodiment provides a kind of preparation method of solvent blue 63 dyes, and it comprises the following steps:
(a)向250ml的反应容器中加入间甲苯胺120g，在搅拌条件下依次加入1-甲氨基-4-溴蒽醌60g、氢氧化钠30g和硫酸铜0.4g，随后升温至100℃，反应7小时至终点；(a) Add m-toluidine 120g to a 250ml reaction vessel, add 60g of 1-methylamino-4-bromoanthraquinone, 30g of sodium hydroxide and 0.4g of copper sulfate successively under stirring conditions, then heat up to 100°C, and react 7 hours to the end;
(b)将步骤(a)的产物降温至60℃，随后加入100ml甲醇进行离析；搅拌后降温至30℃，经过滤、洗涤(用100ml甲醇分2～5次洗涤滤饼，再用500ml、60℃左右热水洗涤，)、烘干即可，得产品59.2g，产率为92％，纯度为99％，洗涤废水量为600mL。(b) Cool the product of step (a) to 60°C, then add 100ml methanol for isolation; cool to 30°C after stirring, filter and wash (wash the filter cake 2 to 5 times with 100ml methanol, then use 500ml, Washing in hot water at about 60° C.), and drying to obtain 59.2 g of the product, the yield is 92%, the purity is 99%, and the amount of washing wastewater is 600 mL.
实施例2Example 2
本实施例提供一种溶剂蓝63染料的制备方法，它包括以下步骤：The present embodiment provides a kind of preparation method of solvent blue 63 dyes, and it comprises the following steps:
(a)向250ml的反应容器中加入间甲苯胺160g，在搅拌条件下依次加入1-甲氨基-4-溴蒽醌60g、氢氧化钠40g和硫酸铜0.8g，随后升温至130℃，反应4小时至终点；(a) Add m-toluidine 160g to a 250ml reaction vessel, add 60g of 1-methylamino-4-bromoanthraquinone, 40g of sodium hydroxide and 0.8g of copper sulfate successively under stirring conditions, then heat up to 130°C, and react 4 hours to the end;
(b)将步骤(a)的产物降温至70℃，随后加入150ml甲醇进行离析；搅拌后降温至50℃，经过滤、洗涤(用160ml甲醇分2～5次洗涤滤饼，再用500ml、60℃左右热水洗涤，)、烘干即可，得产品58.5g，产率为91％，纯度为99％，洗涤废水量为650mL。(b) The product of step (a) is cooled to 70°C, and then 150ml of methanol is added for isolation; after stirring, the temperature is lowered to 50°C, filtered and washed (washing the filter cake 2 to 5 times with 160ml of methanol, and then with 500ml, Washing with hot water at about 60°C, drying, and then obtaining 58.5 g of the product, the yield is 91%, the purity is 99%, and the amount of washing wastewater is 650 mL.
实施例3Example 3
本实施例提供一种溶剂蓝63染料的制备方法，它包括以下步骤：The present embodiment provides a kind of preparation method of solvent blue 63 dyes, and it comprises the following steps:
(a)向250ml的反应容器中加入间甲苯胺150g，在搅拌条件下依次加入1-甲氨基-4-溴蒽醌60g、氢氧化钠35g和硫酸铜0.5g，随后升温至120℃，反应5小时至终点；(a) Add 150 g of m-toluidine to a 250 ml reaction vessel, add 60 g of 1-methylamino-4-bromoanthraquinone, 35 g of sodium hydroxide and 0.5 g of copper sulfate in sequence under stirring, then heat up to 120° C., and react 5 hours to the end;
(b)将步骤(a)的产物降温至65℃，随后加入120ml甲醇进行离析；搅拌后降温至35℃，经过滤、洗涤(用150ml甲醇分2～5次洗涤滤饼，再用300ml、60℃左右热水洗涤，)、烘干即可，得产品58.5g，产率为91％，纯度为99％，洗涤废水量为600mL。(b) The product of step (a) is cooled to 65°C, and then 120ml of methanol is added for isolation; after stirring, the temperature is lowered to 35°C, filtered and washed (washing the filter cake 2 to 5 times with 150ml of methanol, and then with 300ml, Washing in hot water at about 60°C, drying, and 58.5 g of the product were obtained, with a yield of 91%, a purity of 99%, and a washing wastewater volume of 600 mL.
对比例1Comparative example 1
本对比例提供一种常规溶剂蓝63染料的制备方法，它包括以下步骤：This comparative example provides a kind of preparation method of conventional solvent blue 63 dyes, and it comprises the following steps:
(a)向250ml的反应容器中加入间甲苯胺40g、氯苯160g，在搅拌条件下依次加入1-甲氨基-4-溴蒽醌60g、氢氧化钠60g和硫酸铜0.8g，随后升温至130℃，反应10小时至终点；(a) add m-toluidine 40g, chlorobenzene 160g in the reaction container of 250ml, add 1-methylamino-4-bromoanthraquinone 60g, sodium hydroxide 60g and copper sulfate 0.8g successively under stirring condition, be warming up to 130°C, react for 10 hours to the end;
(b)将步骤(a)的产物降温至70℃，随后加入160ml甲醇进行离析；搅拌后降温至50℃，经过滤、洗涤(先用160ml甲醇分2～5次洗涤滤饼，再用1500ml、60℃的热水洗涤)、烘干即可，得产品54.5g，产率为85％，纯度为97.5％，洗涤废水量为1600mL。(b) Cool the product of step (a) to 70°C, then add 160ml methanol for isolation; after stirring, cool down to 50°C, filter and wash (wash the filter cake 2 to 5 times with 160ml methanol, then wash the filter cake with 1500ml , hot water washing at 60° C.) and drying to obtain 54.5 g of the product, with a yield of 85%, a purity of 97.5%, and a washing wastewater volume of 1600 mL.
上述实施例只为说明本发明的技术构思及特点，其目的在于让熟悉此项技术的人士能够了解本发明的内容并据以实施，并不能以此限制本发明的保护范围。凡根据本发明精神实质所作的等效变化或修饰，都应涵盖在本发明的保护范围之内。The above-mentioned embodiments are only to illustrate the technical concept and characteristics of the present invention, and the purpose is to enable those skilled in the art to understand the content of the present invention and implement it accordingly, and not to limit the protection scope of the present invention. All equivalent changes or modifications made according to the spirit of the present invention shall fall within the protection scope of the present invention.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5978367A (en) * | 1982-10-27 | 1984-05-07 | Canon Inc | Production of toner |
| US5367075A (en) * | 1986-12-01 | 1994-11-22 | Sumitomo Chemical Company, Limited | Anthrapyridone compounds, their production process and their use |
| WO2011081200A1 (en) * | 2009-12-28 | 2011-07-07 | 大日本印刷株式会社 | Method for producing a lake compound |
| JP2014101486A (en) * | 2012-05-31 | 2014-06-05 | Nippon Kayaku Co Ltd | Dye, composition and colored body |
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| JP2016204651A (en) * | 2015-04-17 | 2016-12-08 | キヤノン株式会社 | Ink set and sheet for thermal ink-transfer recording |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5978367A (en) * | 1982-10-27 | 1984-05-07 | Canon Inc | Production of toner |
| US5367075A (en) * | 1986-12-01 | 1994-11-22 | Sumitomo Chemical Company, Limited | Anthrapyridone compounds, their production process and their use |
| WO2011081200A1 (en) * | 2009-12-28 | 2011-07-07 | 大日本印刷株式会社 | Method for producing a lake compound |
| JP2014101486A (en) * | 2012-05-31 | 2014-06-05 | Nippon Kayaku Co Ltd | Dye, composition and colored body |
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| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method of solvent blue 63 dye Granted publication date: 20180803 Pledgee: Tongling Branch of China Everbright Bank Co.,Ltd. Pledgor: ANHUI QINGKE RUIJIE NEW MATERIAL CO.,LTD. Registration number: Y2024980048812 |