C.I.颜料红177中间体的制备工艺改进

doi:10.11944/j.issn.1000-0518.2020.04.190251

摘要/Abstract

摘要：

本文较为系统地研究了铜粉催化剂加入方式对C.I.颜料红177中间体4,4'-二氨基-1,1'-二蒽醌-3,3'-二磺酸(DAS)合成过程中的乌尔曼偶联反应速率的影响规律。研究结果表明,在55 ℃较佳反应温度下,先加入与溴氨酸钠质量比为2:5的铜粉,反应一段时间后再加入与溴氨酸钠的质量比为1:5的铜粉,与一次性加入与溴氨酸钠的质量比为3:5的铜粉相比较,综合反应时间可节省2~3 h。另外,对于DAS中混有的铜盐,采取在制备过程中加入柠檬酸的方法予以去除,此举可提高DAS的纯度。当铜粉与柠檬酸的质量比为6:1时,可使DAS中铜盐的含量小于0.001%。此外还探究了蒸馏后滤液的剩余量对DAS收率的影响,结果表明,滤液的剩余量在20 mL时,DAS的收率在95%以上。基于本文的研究结果提出,欲进一步提高该反应的收率,需要寻找更高效的催化剂。

关键词: C.I.颜料红177中间体, 催化剂, 铜粉, 柠檬酸

Abstract:

The effect of batch addition of the catalyst (copper powder) on the reaction rate during the synthesis of 4,4'-diamino-1,1'-dianthraquinone-3,3'-disulfonic acid (DAS) was investigated systematically. The results indicate that 55 ℃ is the preferred reaction temperature. Copper powder and sodium bromate with a mass ratio of of 2:5 are first added, and the second portion of catalyst with a mass ratio of 1:5 copper powder to sodium bromate is then added during the reaction. The reaction time could be saved for 2~3 h compared to adding copper powder at one time (the mass ratio of copper powder to sodium bromate is 3:5). The copper salt mixed in DAS could be removed efficiently by addition of citric acid during the preparation process, which can improve the purity of DAS. When the mass ratio of copper powder to citric acid is 6:1, the content of copper salt in DAS is less than 0.001%. In addition, the influence of the residual amount of the filtrate after distillation on the yield of DAS is also explored and the yield of DAS is above 95% when the remaining amount of filtrate is 20 mL. The results of this study also indicate that to further improve the yield of the reaction, more efficient catalyst is needed.

Key words: C.I. Pigment red 177 intermediate, catalyst, copper powder, citric acid

张天永, 任忠静, 李彬, 姜爽, 史继星, 石志强, 吕东军. C.I.颜料红177中间体的制备工艺改进[J]. 应用化学, 2020, 37(4): 433-439.

ZHANG Tianyong, Ren Zhongjing, LI Bin, JIANG Shuang, SHI Jixing, SHI Zhiqiang, LÜ Dongjun. An Efficient Method for Improved Preparation of C.I. Pigment Red 177 Intermediate[J]. Chinese Journal of Applied Chemistry, 2020, 37(4): 433-439.

参考文献

[1]	ZHAO Jinbang. Application of Organic Pigments in Coatings Industry and Its Progress[J]. Shanghai Coat, 2008,46(1):25-30(in Chinese). 赵金榜. 有机颜料在涂料中的应用与发展[J]. 上海涂料, 2008,46(1):25-30.
[2]	ZHANG Tianyong. Synthetic Technology of C.I. Pigment Red 177[J]. Chem Intermed, 2004,1(8):72(in Chinese). 张天永. C.I.颜料红177的合成技术[J]. 化工中间体, 2004,1(8):72.
[3]	ZHANG Tianyong, LI Wei, LI Bin, et al. Synthesis of C.I. Pigment Red 177 in Ionic Liquids[J]. Fine Chem, 2014,31(9):1132-1136(in Chinese). 张天永,李威,李彬,等. 离子液中制备颜料红177的方法[J]. 精细化工, 2014,31(9):1132-1136.
[4]	Yoo J, Bum L S, Jang J H. Colored Photosensitive Resin Composition Used in Color Filter of Organic Light Emitting Element for Image Display Apparatus, Comprises Xanthene-Based Dye, and Colorant Including C.I. Yellow Pigments and C.I. Red Pigments: KR,2019107790A[P].2019-09-23.
[5]	Tsunekawa M, Hirano A, Terashima Y. Red Coloring Composition for Forming Color Filter, Comprises Red Dye Including Azo Pigment and Pigment Red, Yellow Dye Containing Pigment Yellow, Alkali-Soluble Resin, Photopolymerizable Monomer and Photoinitiator:JP,2018159749A[P].2018-10-11
[6]	Ullmann F. On a New Formation Manner of Diphenylamine Derivatives[J]. Chem Ber, 1903,36:2382-2384.
[7]	Evans D A, Wood M R, Trotter B W, et al. Total Syntheses of Vancomycin and Eremomycin Aglycons[J]. Angew Chem Int Ed, 1998,37(19):2700-2704.
[8]	Angelo N D, Peterson J J, Bookers K, et al. Effect of Microwave Heating on Ullmann-Type Heterocycle-Aryl Ether Synthesis Using Chloroheterocycles[J]. Tetrahedron Lett, 2006,47(29):5045-5048.
[9]	CIBA Limited. 4,4'-Diamino-1,1'-dianthraquinonyl Compounds and Process for Their Manufacture:GB,926514[P].1963-05-22.
[10]	FEI Xuening, ZHOU Chunlong. Synthesis and Pigmentation of C.I. Pigment Red 177[J]. Mod Paint Finish, 1996,4:4-7(in Chinese). 费学宁,周春隆. 4,4'-二氨基-1,1'-二蒽醌(C.I.颜料红177)合成及其颜料化的研究[J]. 现代涂料与涂装, 1996,4:4-7.
[11]	ZHANG Tianyong, LI Wei, LI Bin, et al. Study on Ullmann Condensation Reaction of Producing DAS Catalyzed by Fresh Copper Powder in One-Pot Method[J]. Spec Petrochem, 2014,31(1):42-45(in Chinese). 张天永,李威,李彬,等. 新鲜铜粉“一锅法”催化Ullmann偶合反应制备4,4'-二氨基-1,1'-二蒽醌-3,3'-二磺酸钠[J]. 精细石油化工, 2014,31(1):42-45.
[12]	ZHANG Tianyong, LI Bin, FEI Xuening, et al. Preparation of Supported Copper Powder Catalyst for Ullmann Condensation Reaction of Bromamine Acid:CN,201310456366.5[P].2015-07-01(in Chinese). 张天永,李彬,费学宁,等. 用于溴氨酸乌尔曼缩合反应的铜粉载体催化剂的制备方法:CN, 201310456366.5[P].2015-07-01.
[13]	ZHANG Tianyong, LI Wei, LI Bin, et al. Synthesis of C.I. Pigment Red 177 in Ionic Liquids:CN, 2014100652772[P].2016-02-17(in Chinese). 张天永,李威,李彬,等. 离子液中制备颜料红177 的方法:CN, 2014100652772[P].2016-02-17.
[14]	ZHANG Tianyong, ZHU Shaodi, LI Bin, et al. Synthesis of 4,4'-Diamino-1,1'-dianthraquinone-3,3'-disulfonic Acid in Organic Solvent Systems[J]. CIESC J, 2017,68(1):146-153(in Chinese). 张天永,朱少迪,李彬,等. 有机溶剂中合成4,4'-二氨基-1,1'-联蒽醌-3,3'-二磺酸[J]. 化工学报, 2017,68(1):146-153.
[15]	FU Dongmei, ZHANG Feifang, WANG Lianzhi, et al. Simultaneous Removal of Nitrobenzene and Phenol by Homogenous Catalytic Wet Air Oxidation[J]. Chinese J Catal, 2015,36(7):952-956(in Chinese). 付冬梅,章飞芳,王联芝,等. 催化湿式共氧化法同时去除硝基苯和苯酚[J]. 催化学报, 2015,(7):952-956.
[16]	HUANG Tianjiao, ZHANG Yaping, ZHUANG Ke, et al. Preparation of Honeycombed Holmium-Modified Fe-Mn/TiO2 Catalyst and Its Performance in the Low Temperatur Selective Catalytic Reduction of NOx[J]. J Fuel Chem Technol, 2018,46(3):319-327(in Chinese). 黄天娇,张亚平,庄柯, 等. 蜂窝状Ho改性Fe-Mn/TiO2催化剂的制备及其低温选择催化还原(SCR)脱硝性能[J]. 燃料化学学报, 2018,46(3):319-327.
[17]	LI Zhihua, ZHANG Guiqing, GUAN Wenjuan, et al. Study on Hydrometallurgical Extraction of Molybdenum and Vanadium from Spent HDS Catalysts[J]. Rare Met Cem Carbides, 2016,44(3):12-16(in Chinese). 李治华,张贵清,关文娟,等. 从HDS废催化剂中湿法提取Mo和V的研究[J]. 稀有金属与硬质合金, 2016,44(3):12-16