Citation: Yuxin Mao, Changlu Zhou, Chaoying Wang, Zhong Xin. Continuous-flow synthesis and crystal modification of Pigment Red 53[J]. Chinese Chemical Letters, ;2023, 34(8): 108061. doi: 10.1016/j.cclet.2022.108061 shu

Continuous-flow synthesis and crystal modification of Pigment Red 53

Yuxin Mao ^a ,
Changlu Zhou ^a ,
Chaoying Wang ^a ,
Zhong Xin ^{a, b, *,}

a.
Shanghai Key Laboratory of Multiphase Materials Chemical Engineering, School of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China
b.
State Key Laboratory of Chemical Engineering, School of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, China

xzh@ecust.edu.cn

Received Date: 6 September 2022
Revised Date: 9 December 2022
Accepted Date: 12 December 2022
Available Online: 16 December 2022

Figures(8)

In this study, a continuous-flow procedure containing four steps has been developed to synthesize Pigment Red 53 and modify its crystal structure. This process avoided the problems of conveying highly insoluble reaction intermediates by removing intermediate operating steps. After optimization, the overall yield of Pigment Red 53:1 reached 97.1% in the total residence time of 80 s by this diazotization-coupling-laking-crystal transition process. From batch to continuous flow, the purity of products increased from 97.1% to 98.2% and the median diameter of pigment particles decreased from 14 µm to 1.9 µm. This process achieved a similar crystal transition effect in 18 s as in batch, producing α, δ and ν crystals of Pigment Red 53:2 as expected. In conclusion, this continuous-flow procedure displays advantages in both synthesis and crystal transition, indicating another potential use for industrial application.
- C.I. Pigment Red 53,
- Continuous synthesis,
- Process optimization,
- Crystal modification
1. [1]
  K. Hunger, P. Mischke, W. Rieper, Ullmann's Encyclopedia of Industrial Chemistry, 5th. ed., Wiley-VCH, Weinheim, 2017.
2. [2]
  U. Nickel, K. Kund, F. Alfter, JP: JP2001–184775, 2002.
3. [3]
  I. Szele, H. Zollinger, Preparative Organic Chemistry, Springer, Berlin Heidelberg, 1983.
4. [4]
  Z. Shi, X. Wang, D. Yin, Org. Process Res. Dev. 26 (2021) 661–669.
5. [5]
  M. Köckinger, B. Wyler, C. Aellig, Org. Process Res. Dev. 24 (2020) 2217–2227. doi: 10.1021/acs.oprd.0c00254
6. [6]
  N. Kockmann, M. Gottsponer, D.M. Roberge, Chem. Eng. J. 167 (2011) 718–726. doi: 10.1016/j.cej.2010.08.089
7. [7]
  S.J. Miller, H. Ishitani, Y. Furiya, Org. Process Res. Dev. 25 (2021) 192–198. doi: 10.1021/acs.oprd.0c00391
8. [8]
  F.M. Akwi, P. Watts, Chem. Commun. 54 (2018) 13894–13928. doi: 10.1039/C8CC07427E
9. [9]
  H. Pennemann, S. Forster, J. Kinkel, Org. Process Res. Dev. 9 (2005) 188–192. doi: 10.1021/op049789e
10. [10]
  Z.Q. Yu, G. Tong, X.X. Xie, Org. Process Res. Dev. 19 (2015) 892–896. doi: 10.1021/acs.oprd.5b00115
11. [11]
  Z.Q. Yu, X.X. Xie, H. Dong, Org. Process Res. Dev. 20 (2016) 774–779. doi: 10.1021/acs.oprd.6b00023
12. [12]
  J. Ren, M. Wu, K. Dong, Chin. Chem. Lett. 34 (2023) 107694. doi: 10.1016/j.cclet.2022.07.037
13. [13]
  Y. Xin, S. Peng, J. Chen, Chin. Chem. Lett. 31 (2020) 1448–1461. doi: 10.1016/j.cclet.2019.09.054
14. [14]
  C. Wille, H.P. Gabski, T. Haller, Chem. Eng. J. 101 (2004) 179–185. doi: 10.1016/j.cej.2003.11.007
15. [15]
  F.J. Wang, A. Chen, S.D. Ling, React. Chem. Eng. 6 (2021) 1462–1474. doi: 10.1039/D1RE00075F
16. [16]
  F.J. Wang, J.P. Huang, J.H. Xu, Org. Process Res. Dev. 23 (2019) 2637–2646. doi: 10.1021/acs.oprd.9b00286
17. [17]
  A. Pomberger, Y.M. Mo, K.Y. Nandiwale, Org. Process Res. Dev. 23 (2019) 2699–2706. doi: 10.1021/acs.oprd.9b00378
18. [18]
  F.J. Wang, Y.C. Ding, J.H. Xu, Ind. Eng. Chem. Res. 58 (2019) 16338–16347. doi: 10.1021/acs.iecr.9b03045
19. [19]
  F.M. Akwi, P. Watts, Beilstein J. Org. Chem. 12 (2016) 1987–2004. doi: 10.3762/bjoc.12.186
20. [20]
  F.J. Wang, J.P. Huang, J.H. Xu, Chem. Eng. Process 127 (2018) 43–49. doi: 10.1016/j.cep.2018.03.014
21. [21]
  C.A. Shukla, M.S. Kute, A.A. Kulkarni, Green Chem. 23 (2021) 6614–6624. doi: 10.1039/D1GC01133B
22. [22]
  W. Herbst, K. Hunger, G. Wilker, Industrial Organic Pigments (Production, Properties, Applications), 3rd ed., Wiley-VCH, Weinheim, 2004.
23. [23]
  T. Gorelik, M.U. Schmidt, J. Bruning, Cryst. Growth Des. 9 (2009) 3898–3903. doi: 10.1021/cg801099r
24. [24]
  A.R. Kennedy, C. Mcnair, W.E. Smith, Angew. Chem. Int. Edit. 39 (2000) 638. doi: 10.1002/(SICI)1521-3773(20000204)39:3<638::AID-ANIE638>3.0.CO;2-K
25. [25]
  W. Luo, F. Liu, Y. Guo, Chin. Chem. Lett. 34 (2023) 107636. doi: 10.1016/j.cclet.2022.06.059
26. [26]
  Y. Mao, Z. Xin, CP: CN202210876093.9, 2022.
27. [27]
  R. Kaminski, U. Lauk, P. Skrabal, Helv. Chim. Acta 66 (1983) 2002–2017. doi: 10.1002/hlca.19830660712
28. [28]
  J. Schröder, Prog. Org. Coat. 16 (1988) 3–17. doi: 10.1016/0033-0655(88)80003-7
29. [29]
  L. Tapmeyer, D. Eisenbeil, M. Bolte, Acta Crystallogr. E Crystallogr. Commun. 77 (2021) 402–405. doi: 10.1107/S2056989021002577
30. [30]
  L. Tapmeyer, S. Hill, M. Bolte, Acta Crystallogr. C: Struct. Chem. 76 (2020) 716–722. doi: 10.1107/S2053229620008530
31. [31]
  S.N. Ivashevskaya, J. Van De Streek, J.E. Djanhan, Acta Crystallogr. B: Struct. Sci. 65 (2009) 212–222. doi: 10.1107/S0108768109001827
32. [32]
  E.A. Kabova, J.C. Cole, O. Korb, J. Appl. Crystallogr. 50 (2017) 1421–1427. doi: 10.1107/S1600576717012596
33. [33]
  S.N. Ivashevskaya, Acta Crystallogr. E Crystallogr. Commun. 73 (2017) 507–510. doi: 10.1107/S2056989017003309
34. [34]
  M.U. Schmidt, EP: EP99110831. 7, 2002.
35. [35]
  S.M.U. Dr., M.H.J. Dr, EP: EP0965616, 1999.
36. [36]
  F. Schui, R. Deubel, N. Wester, Canada Patent: CA1219858 A1, 1987.
1. [1]
  Hui Jin , Qin Cai , Peiwen Liu , Yan Chen , Derong Wang , Weiping Zhu , Yufang Xu , Xuhong Qian . Multistep continuous flow synthesis of Erlotinib. Chinese Chemical Letters, 2024, 35(4): 108721-. doi: 10.1016/j.cclet.2023.108721
2. [2]
  Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896
3. [3]
  Zhixiang Li , Zhirong Yang , Chang Yao , Bin Wu , Gang Qian , Xuezhi Duan , Xinggui Zhou , Jing Zhang . Efficient continuous synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole in a millimeter scale photoreactor. Chinese Chemical Letters, 2024, 35(4): 108893-. doi: 10.1016/j.cclet.2023.108893
4. [4]
  Fengyu Zhang , Yali Liang , Zhangran Ye , Lei Deng , Yunna Guo , Ping Qiu , Peng Jia , Qiaobao Zhang , Liqiang Zhang . Enhanced electrochemical performance of nanoscale single crystal NMC811 modification by coating LiNbO₃. Chinese Chemical Letters, 2024, 35(5): 108655-. doi: 10.1016/j.cclet.2023.108655
5. [5]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
6. [6]
  Shu-Ran Xu , Fang-Xing Xiao . Metal halide perovskites quantum dots: Synthesis, and modification strategies for solar CO2 conversion. Chinese Journal of Structural Chemistry, 2023, 42(12): 100173-100173. doi: 10.1016/j.cjsc.2023.100173
7. [7]
  Chaochao Jin , Kai Li , Jiongpei Zhang , Zhihua Wang , Jiajing Tan . N,O-Bidentated difluoroboron complexes based on pyridine-ester enolates: Facile synthesis, post-complexation modification, optical properties, and applications. Chinese Chemical Letters, 2024, 35(9): 109532-. doi: 10.1016/j.cclet.2024.109532
8. [8]
  Jianmei Han , Peng Wang , Hua Zhang , Ning Song , Xuguang An , Baojuan Xi , Shenglin Xiong . Performance optimization of chalcogenide catalytic materials in lithium-sulfur batteries: Structural and electronic engineering. Chinese Chemical Letters, 2024, 35(7): 109543-. doi: 10.1016/j.cclet.2024.109543
9. [9]
  Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147
10. [10]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
11. [11]
  Jiakun Bai , Junhui Jia , Aisen Li . An elastic organic crystal with piezochromic luminescent behavior. Chinese Journal of Structural Chemistry, 2024, 43(6): 100323-100323. doi: 10.1016/j.cjsc.2024.100323
12. [12]
  Jingping Hu , Jing Xu . Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C₁₄–epi-deoxycalyciphylline H. Chinese Chemical Letters, 2024, 35(4): 108733-. doi: 10.1016/j.cclet.2023.108733
13. [13]
  Wenbi Wu , Yinchu Dong , Haofan Liu , Xuebing Jiang , Li Li , Yi Zhang , Maling Gou . Modification of plasma protein for bioprinting via photopolymerization. Chinese Chemical Letters, 2024, 35(8): 109260-. doi: 10.1016/j.cclet.2023.109260
14. [14]
  Ping Wang , Tianbao Zhang , Zhenxing Li . Reconstruction mechanism of Cu surface in CO2 reduction process. Chinese Journal of Structural Chemistry, 2024, 43(8): 100328-100328. doi: 10.1016/j.cjsc.2024.100328
15. [15]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
16. [16]
  Rongliang Deng , Yihang Chen , Xiaotong Fan , Guolong Chen , Shuli Wang , Changzhi Yu , Xiao Yang , Tingzhu Wu , Zhong Chen , Yue Lin . Break of thermal equilibrium between optical and acoustic phonon branches of CsPbI₃ under continuous-wave light excitation and cryogenic temperature. Chinese Chemical Letters, 2024, 35(7): 109346-. doi: 10.1016/j.cclet.2023.109346
17. [17]
  Peng Meng , Qian-Cheng Luo , Aidan Brock , Xiaodong Wang , Mahboobeh Shahbazi , Aaron Micallef , John McMurtrie , Dongchen Qi , Yan-Zhen Zheng , Jingsan Xu . Molar ratio induced crystal transformation from coordination complex to coordination polymers. Chinese Chemical Letters, 2024, 35(4): 108542-. doi: 10.1016/j.cclet.2023.108542
18. [18]
  Jun Lu , Jinrui Yan , Yaohao Guo , Junjie Qiu , Shuangliang Zhao , Bo Bao . Controlling solid form and crystal habit of triphenylmethanol by antisolvent crystallization in a microfluidic device. Chinese Chemical Letters, 2024, 35(4): 108876-. doi: 10.1016/j.cclet.2023.108876
19. [19]
  Ce Liang , Qiuhui Sun , Adel Al-Salihy , Mengxin Chen , Ping Xu . Recent advances in crystal phase induced surface-enhanced Raman scattering. Chinese Chemical Letters, 2024, 35(9): 109306-. doi: 10.1016/j.cclet.2023.109306
20. [20]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(157)
HTML views(1)

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