Continuous-flow synthesis of Pigment Red 57 in a microreactor system

doi:10.11949/0438-1157.20240304

Abstract

Abstract:

Azo lake pigments are one of the important organic pigment varieties and are widely used in various industrial fields. The continuous-flow synthesis of Pigment Red 57 using the microreactor technology is of great significance for the innovation of azo lake pigments production technology. First, a microreactor system was built, and the reaction conditions of diazotization, coupling and laking process were optimized in the system. Under the optimal reaction conditions, the yield of diazonium salt was greater than 99%, the yield of pigment red was greater than 99%, and the solid recovery after laking was close to 100%. Finally, different alkali metal salts or alkaline earth metal solutions were used for laking process to achieve the regulation of chromatic light. Among them, the chromatic light after Sr²⁺ and Ba²⁺ laking was brighter, and the red and yellow hues were intense. The chromatic light after Zn²⁺, Mg²⁺, Mn²⁺ laking was dark, and the green and blue hues were intense.

Key words: microreactor, microscale, diazotization, coupling, laking, azo lake pigment

摘要：

偶氮色淀颜料属于重要的有机颜料品种之一，广泛应用于各类工业领域。利用微反应器技术实现颜料红57的连续化合成，对于偶氮色淀颜料生产技术的革新有重要意义。首先，搭建微反应器系统，并在系统内对重氮化反应、偶合反应、色淀化反应过程进行反应条件优化。在最优的反应条件下，重氮盐的收率大于99%，颜料红收率大于99%，颜料红色淀后的固体回收率接近100%。然后，采用不同碱金属盐或者碱土金属溶液进行色淀化反应，实现对颜料色光的调控。其中，Sr²⁺、Ba²⁺色淀后色光偏亮，同时偏红偏黄；Zn²⁺、Mg²⁺、Mn²⁺色淀后色光偏暗，同时偏绿偏蓝。

关键词: 微反应器, 微尺度, 重氮化反应, 偶合反应, 色淀化反应, 偶氮色淀颜料

CLC Number:

TQ 052.5

Fajun WANG, An CHEN, Jianhong XU. Continuous-flow synthesis of Pigment Red 57 in a microreactor system[J]. CIESC Journal, 2024, 75(10): 3600-3609.

王法军, 陈安, 徐建鸿. 微反应器内颜料红57连续化合成工艺[J]. 化工学报, 2024, 75(10): 3600-3609.

Figures/Tables 16

Fig.1 Experimental setup for continuous-flow synthesis of Pigment Red 57

Fig.2 Reactions for Pigment Red 57 (Ca2+ laking) synthesis

Table 1 Elution gradient

时间/min	乙酸铵缓冲液比例/%	乙腈比例/%
0	85	15
12.0	45	55
19.0	15	85
19.1	85	15
25.0	85	15

Fig.3 Peak positions in liquid chromatography of the solution

Fig.4 Standard operating curves for different compounds

Table 2 Standard working curve equation

化合物	标准工作曲线方程	R²
4-氨基甲苯-3-磺酸	C=0.1275A	0.9996
2-羟基-3-萘甲酸	C=0.0297A	0.9999
颜料红57	C=0.0695A	1.0000

Fig.5 Effect of reaction temperature on the yield of diazonium salt

Fig.6 Effect of reaction time on the yield of diazonium salt

Fig.7 Effect of N(NaNO2)/N(Ar-NH2) on the yield of diazonium salt

Fig.8 Effect of pH on the residual rate of diazonium salt (X) and the yield of Pigment Red 57 (Y)

Fig.9 Effect of reaction time on the residual rate of diazonium salt (X) and the yield of Pigment Red 57 (Y)

Fig.10 Effect of reaction temperature on the residual rate of diazonium salt (X) and the yield of Pigment Red 57 (Y)

Fig.11 Effect of reaction temperature on the residual rate of Pigment Red 57

Fig.12 Effect of reaction time on the residual rate of Pigment Red 57

Fig.13 Chromatic light diagram of pigment after different ion color laking

Fig.14 Contrast of chromatic light of different ionic lake pigments

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