Citation: FU Xinmei, ZHANG Rong, WU Zuwang. Structure identification of reactive dyes by high performance liquid chromatography-photodiode array detection/mass spectrometry[J]. Chinese Journal of Chromatography, ;2014, 32(11): 1172-1180. doi: 10.3724/SP.J.1123.2014.07038 shu

Structure identification of reactive dyes by high performance liquid chromatography-photodiode array detection/mass spectrometry

1.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China

Corresponding author: FU Xinmei,
Received Date: 23 July 2014
Available Online: 27 August 2014

Based on years of experience on analyzing reactive dyes by high performance liquid chromatography-photodiode array detection/mass spectrometry (HPLC-DAD/MS), the essential applications for current structure identification of the commercial reactive dyes are summarized in three aspects. Commercial dyes always include several kinds of components. They are assistants for increasing solubility of synthetic dyes, multi-color synthetic dyes and their by-products derived from synthesis and storage. HPLC-DAD/MS technique can separate most of the components, and provide UV-Vis spectra and mass spectra individually. The separation and analysis can be achieved only through one injection without pre-purification of commercial dyes. Compared with traditional analytical methods, HPLC-DAD/MS technique reduces greatly not only the workload of analysis but also provides fully the actual compositions of the dyestuff. The reactive groups can react with ethanolamine or diethanolamine under moderate condition without structure destruction of dyes. The molecular masses before and after derivatization can be determined by MS, and then the type and number of reactive groups can be ascertained by so called "mass difference by derivative method". The chromophore of the dye can be identified by full spectrum scanning function of DAD. HPLC-DAD/MS analytical technique is very special and useful for the structure analysis of multi-component mixed commercial dyes. As examples, the identifications of three multi-component mixed structures of commercial dyes (Reactive Gray, Reactive Supra Black and Reactive Marine Blue) were given.
1. [1]
  [1] China Dyestuff Industry Association. China Association Communication (中国染料工业协会. 中国染协通讯), 2014(4): 5
2. [2]
  [2] Yang J Z. Analysis of Dyestuff. Beijing: Chemical Industry Press (杨锦宗. 染料分析与剖析. 北京: 化学工业出版社), 1997
3. [3]
  [3] Vankataraman K. The Analytical Chemistry of Synthetic Dyes. New York: John Wiley & Sun, 1977
4. [4]
  [4] Zhao P C, Wang Y J, Cui L, et al. Chinese Journal of Chromatography (赵鹏程, 王彦吉, 崔岚, 等. 色谱), 2001, 19(4): 382
5. [5]
  [5] Lang W, Sirisansaneeyakul S, Martins L O, et al. J Environ Manage, 2014, 132: 155
6. [6]
  [6] Enaud E, Trovaslet M, Bruyneel F, et al. Dyes Pigments, 2010, 85: 99
7. [7]
  [7] Zhu H, Huang K Y, Fu J F, et al. Chinese Journal of Chromatography (朱浩, 黄坤玉, 付建飞, 等. 色谱), 2014, 32(3): 224
8. [8]
  [8] Liu J, Gong Z B. Chinese Journal of Chromatography (刘珺, 弓振斌. 色谱), 2012, 30(6): 624
9. [9]
  [9] Zhu N W, Gu L, Yuan H P, et al. Water Res, 2012, 46: 3859
10. [10]
  [10] Hou X L, Wu Y L, Yang T, et al. J Chromatogr B, 2013, 929: 107
11. [11]
  [11] Zhang S F, Lin Z Z, Chen X Z, et al. Journal of Instrumental Analysis (张水锋, 林珍珍, 陈小珍, 等. 分析测试学报), 2012, 31(10): 1229
12. [12]
  [12] Lin W X, Sun X Q, Zhao X R, et al. Chinese Journal of Chromatography (林维宣, 孙兴权, 赵雪蓉, 等. 色谱), 2012, 30(5): 527
13. [13]
  [13] Chen R Q. Dyestuffs and Coloration (陈荣圻. 染料与染色), 2014, 51(2): 14
14. [14]
  [14] Zou H F, Zhang Y K, Lu P Z. Ion-pair High Performance Liquid Chromatography. Zhengzhou: Henan Science Press (邹汉法, 张玉奎, 卢佩章. 离子对高效液相色谱法. 郑州: 河南科学技术出版社), 1996
15. [15]
  [15] Kucharska A, Grabka J. Talanta, 2010, 80: 1045
16. [16]
  [16] Yamamoto E, Ishihama Y, Asakawa N. Talanta, 2014, 127: 219
17. [17]
  [17] Khan S S, Riaz M. Talanta, 2014, 122: 209
18. [18]
  [18] Horvath C, Melander W, Molnar I, et al. Anal Chem, 1977, 49: 2295
19. [19]
  [19] Stranaban J J, Deming S N. Anal Chem, 1982, 54: 2251
20. [20]
  [20] Michopoulos F, Whalley N, Theodoridis G, et al. J Chromatogr A, 2014, 1349: 60
21. [21]
  [21] Biba M, Welch C J, Foley J P. J Pharm Biomed Anal, 2014, 96: 54
22. [22]
  [22] Li B, Zhou X Z, Li J Y, et al. J Chromatogr B, 2014, 969: 12
23. [23]
  [23] Smyth W F, McClean S, O'Kane E, et al. J Chromatogr A, 1999, 854: 259
24. [24]
  [24] Zhang R.[PhD Dissertation]. Dalian: Dalian University of Technology (张蓉.[博士学位论文]. 大连: 大连理工大学), 2009
25. [25]
  [25] Wu Z W, Wang Z, Zhang Z D. Chemical Industry and Engineering Progress (吴祖望, 王专, 张志达. 化工进展), 2009, 28(5): 874
26. [26]
  [26] Wu Z W, Yang W. Dyestuffs and Coloration (吴祖望, 杨威. 染料与染色), 2007, 44(1): 1
27. [27]
  [27] Athanassios T, Thomas V, Georg R. WO Patent. WO2009-053238, 2009-04-30
28. [28]
  [28] Marie S J, Athanassios T. US Patent. US20080256726, 2005-11-29
29. [29]
  [29] Athanassios T, Herbert K. US Patent. US6537332, 1998-07-27
30. [30]
  [30] Wu Z W, Wang Z, Feng B C, et al. China Patent (吴祖望, 王专, 冯柏成, 等. 中国专利), CN200610047488.9, 2007-02-14
31. [31]
  [31] Wang Z, Wu Z W. Color Technol, 2009, 123: 216
32. [32]
  [32] Wang Z, Wu Z W. Text Res, 2010, 80(5): 448
1. [1]
  Zian Lin , Yingxue Jin . Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry (MALDI-MS) for Disease Marker Screening and Identification: A Comprehensive Experiment Teaching Reform in Instrumental Analysis. University Chemistry, 2024, 39(11): 327-334. doi: 10.12461/PKU.DXHX202403066
2. [2]
  Zunxiang Zeng , Yuling Hu , Yufei Hu , Hua Xiao . Analysis of Plant Essential Oils by Supercritical CO₂Extraction with Gas Chromatography-Mass Spectrometry: An Instrumental Analysis Comprehensive Experiment Teaching Reform. University Chemistry, 2024, 39(3): 274-282. doi: 10.3866/PKU.DXHX202309069
3. [3]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . 液相法制备硫化物固体电解质及其在全固态锂电池中的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2309019-. doi: 10.3866/PKU.WHXB202309019
4. [4]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
5. [5]
  Wanqun Hu , Pingping Zhu , Yuan Zheng , Wanqun Zhang , Wei Shao , Hong Wu , Qiang Zhou , Kaiping Yang , Xiang Sheng . Design and Practice of Ideological and Political Case Study in Instrumental Analysis Experiment Course: the Extraction and Structural Identification of Artemisinin. University Chemistry, 2024, 39(2): 203-207. doi: 10.3866/PKU.DXHX202310062
6. [6]
  Chongjing Liu , Yujian Xia , Pengjun Zhang , Shiqiang Wei , Dengfeng Cao , Beibei Sheng , Yongheng Chu , Shuangming Chen , Li Song , Xiaosong Liu . Understanding Solid-Gas and Solid-Liquid Interfaces through Near Ambient Pressure X-Ray Photoelectron Spectroscopy. Acta Physico-Chimica Sinica, 2025, 41(2): 100013-. doi: 10.3866/PKU.WHXB202309036
7. [7]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
8. [8]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
9. [9]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
10. [10]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
11. [11]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
12. [12]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
13. [13]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
14. [14]
  Jiandong Liu , Zhijia Zhang , Mikhail Kamenskii , Filipp Volkov , Svetlana Eliseeva , Jianmin Ma . Research Progress on Cathode Electrolyte Interphase in High-Voltage Lithium Batteries. Acta Physico-Chimica Sinica, 2025, 41(2): 100011-. doi: 10.3866/PKU.WHXB202308048
15. [15]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
16. [16]
  Tao Jiang , Yuting Wang , Lüjin Gao , Yi Zou , Bowen Zhu , Li Chen , Xianzeng Li . Experimental Design for the Preparation of Composite Solid Electrolytes for Application in All-Solid-State Batteries: Exploration of Comprehensive Chemistry Laboratory Teaching. University Chemistry, 2024, 39(2): 371-378. doi: 10.3866/PKU.DXHX202308057
17. [17]
  Liang MA , Honghua ZHANG , Weilu ZHENG , Aoqi YOU , Zhiyong OUYANG , Junjiang CAO . Construction of highly ordered ZIF-8/Au nanocomposite structure arrays and application of surface-enhanced Raman spectroscopy. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1743-1754. doi: 10.11862/CJIC.20240075
18. [18]
  Lingbang Qiu , Jiangmin Jiang , Libo Wang , Lang Bai , Fei Zhou , Gaoyu Zhou , Quanchao Zhuang , Yanhua Cui . 原位电化学阻抗谱监测长寿命热电池Nb₁₂WO₃₃正极材料的高温双放电机制. Acta Physico-Chimica Sinica, 2025, 41(5): 100040-. doi: 10.1016/j.actphy.2024.100040
19. [19]
  Tao Yang , Kaijiao Duan , Siyu Li , Jing Wei , Qingdi Yang , Qian Wang . A Comprehensive and Innovative Chemical Experimental Teaching: Extraction and Identification of Tea Polyphenols from Pu'er Tea and the Application in Hand Cream Making. University Chemistry, 2024, 39(8): 270-275. doi: 10.3866/PKU.DXHX202312040
20. [20]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(192)
HTML views(8)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142