Preparation of supported ionic liquid [HSO3-BMIM][HSO4]/SiO2 and its catalytic property in the esterification of acetic acid and ethanol

doi:10.11949/0438-1157.20220456

Abstract

Abstract:

In order to make the ionic liquids (ILs) easier to separate and recycle while maintaining the catalytic activity, and to reduce the corrosion, a variety of supported ILs were prepared to catalyze the esterification for the synthesis of ethyl acetate (EtAc). The supported ILs are analyzed and characterization by infrared spectroscopy, thermogravimetric, nitrogen adsorption-desorption and scanning electron microscopy. It is found that sol-gel method can immobilize ILs on SiO₂ more effectively than impregnation. In the conditions of R⁰_A∶E = 1, T in the range of 323.15—338.15 K, and x_cat∶HAc in the range of 5%—15%, the supported IL [HSO₃-BMIM][HSO₄]/SiO₂ which prepare by sol-gel method shows fast reaction rate, the conversion of acetic acid (X_HAc) exceeds 50% at the first 30 min, which achieves 70% of the equilibrium conversion (X_HAc = 68%). The LHHW model was used to fit the rate of [HSO₃-BMIM][HSO₄]/SiO₂-catalyzed esterification reaction, and the results showed that the model predicted accurately. The repeatability experimental result showed that X_HAc (t = 4 h) of [HSO₃-BMIM][HSO₄]/SiO₂ in the third run exceeded 60%, which decreased at the 6th run. The catalytic activity and stability of supported IL prepared by sol-gel method are better than that of impregnation. These results show that sol-gel method is more suitable for the preparation of supported ILs.

Key words: ionic liquid, catalyst, ethyl acetate, esterification, immobilization, supported acid

摘要：

为使离子液体(ILs)在保持催化活性的前提下更易分离回收，减轻ILs的腐蚀，制备了固载ILs，并用于催化酯化反应合成乙酸乙酯(EtAc)。通过红外光谱、热失重、N₂吸附-脱附、扫描电镜等对固载ILs进行表征分析，发现溶胶-凝胶(Sol-Gel)法比浸渍法能更有效地固载ILs于二氧化硅(SiO₂)载体上，在催化乙酸乙醇酯化合成EtAc时催化效果较好。反应条件为酸醇比R⁰_A∶E = 1，反应温度T在323.15~338.15 K范围内，催化剂与乙酸质量比x_cat∶HAc在5%~15%范围内时，Sol-Gel法制备的[HSO₃-BMIM][HSO₄]/SiO₂初始反应速率较快，反应30 min时乙酸转化率(X_HAc)超过50%，达到平衡转化率(68%)的约70%。使用LHHW模型拟合[HSO₃-BMIM][HSO₄]/SiO₂催化酯化反应的速率，结果表明该模型预测准确。重复性考察发现，[HSO₃-BMIM][HSO₄]/SiO₂在前三次使用时的X_HAc(t = 4 h)超过60%，经六次使用后有所下降。使用Sol-Gel法制备的固载ILs的催化活性和稳定性优于浸渍法，表明Sol-Gel法更适合用于制备固载ILs。

关键词: 离子液体, 催化剂, 乙酸乙酯, 酯化反应, 固载, 固体酸

CLC Number:

O 621.3

Ruining HE, Yun ZOU, Meng SHI, Yang LI, Jing XU, Zhangfa TONG. Preparation of supported ionic liquid [HSO₃-BMIM][HSO₄]/SiO₂ and its catalytic property in the esterification of acetic acid and ethanol[J]. CIESC Journal, 2022, 73(9): 3880-3894.

何瑞宁, 邹昀, 石萌, 李洋, 徐晶, 童张法. 固载离子液体［HSO₃-BMIM］［HSO₄］/SiO₂的制备及其催化乙酸乙醇酯化反应的研究[J]. 化工学报, 2022, 73(9): 3880-3894.

Figures/Tables 16

Fig.1 Immobilization of ionic liquid [HSO3-BMIM][HSO4] on SiO2 by sol-gel method

Fig.2 The experimental apparatus of the esterification of HAc and EtOH catalyzed by supported ILs

Fig.3 FT-IR spectra of catalystsa ─ SiO2; b ─[HSO3-BMIM][HSO4]; c ─[HSO3-BMIM][HSO4]/SiO2;d ─ reused [HSO3-BMIM][HSO4]/SiO2

Fig.4 TG-DTG analysis of catalysts

Table 1 BET surface properties of the supporters before and after immobilization

样品	S_BET /(m²·g^-1)	D_p/nm
硅胶	640.66	2.51
无固载ILs的硅凝胶SiO₂	533.81	2.07
[HSO₃-BMIM][HSO₄]/SiO₂	70.34	6.77
reused [HSO₃-BMIM][HSO₄]/SiO₂	340.65	5.36

Fig.5 Pore size distribution and N2 adsorption-desorption curve

Fig.6 The surface morphology of catalysts

Fig.7 The distribution of acid strength of [HSO3-BMIM][HSO4]/SiO2 and [HSO3-BMIM][HSO4]/Sil

Fig.8 Influence of reaction temperature on conversion of HAc at xcat∶HAc= 10%, R0A∶E=1 catalyzed by [HSO3-BMIM][HSO4]/SiO2 (solid lines) and [HSO3-BMIM][HSO4]/Sil (dash lines)

Fig.9 Influence of catalyst dosage on conversion of HAc at T= 333.15 K, R0A:E = 1 catalyzed by [HSO3-BMIM][HSO4]/SiO2 (solid lines) and [HSO3-BMIM][HSO4]/Sil (dash lines)

Fig.10 Influence of the mole ratio of HAc to EtOH on conversion of HAc at T = 333.15 K, xcat∶HAc = 10% catalyzed by [HSO3-BMIM][HSO4]/SiO2 (solid lines) and [HSO3-BMIM][HSO4]/Sil (dash lines)

Fig.11 Performance of recycled catalyst

Table 2 The immobilization yield of ILs/SiO2 and ILs/Sil

样品	r_L /%(mass)
[HSO₃-BMIM][HSO₄]/SiO₂	45.06
[HSO₃-BMIM][HSO₄]/Sil	27.19
6th reused [HSO₃-BMIM][HSO₄]/SiO₂	22.82
6th reused [HSO₃-BMIM][HSO₄]/Sil	20.91

Table 3 Intensity of corrosion of ［HSO3-BMIM］［HSO4］/SiO2，［HSO3-BMIM］［HSO4］ and H2SO4

催化剂

不锈钢薄片表面积S/cm²

质量流失/g

腐蚀速率/

(g·m^-2·h^-1)

[HSO₃-BMIM][HSO₄]/SiO₂

Table 4 Parameters of the kinetic equations based on LHHW models

参数	数值
A₊⁰/(L∙mol^-1∙min^-1)	845.12
E_a+/( J∙mol^-1)	27007.51
A_-⁰/(L∙mol^-1∙min^-1)	673.73
E_a-/(J∙mol^-1)	30000.11
k_EtOH/(L∙mol^-1)	10.01
ΔH_EtOH/(J∙mol^-1)	27993.08
$k H 2 O$ /(L∙mol^-1)	32.70
Δ $H H 2 O$ /(J∙mol^-1)	9346.72
MASE	3.153×10^-4

Table 4 Parameters of the kinetic equations based on LHHW models

参数	数值
A₊⁰/(L∙mol^-1∙min^-1)	845.12
E_a+/( J∙mol^-1)	27007.51
A_-⁰/(L∙mol^-1∙min^-1)	673.73
E_a-/(J∙mol^-1)	30000.11
k_EtOH/(L∙mol^-1)	10.01
ΔH_EtOH/(J∙mol^-1)	27993.08
$k H 2 O$ /(L∙mol^-1)	32.70
Δ $H H 2 O$ /(J∙mol^-1)	9346.72
MASE	3.153×10^-4

Fig.12 Data fitting results of LHHW model on XHAc at experimental catalyst dosage (T= 333.15 K, R0A∶E = 1)

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Preparation of supported ionic liquid [HSO₃-BMIM][HSO₄]/SiO₂ and its catalytic property in the esterification of acetic acid and ethanol

固载离子液体［HSO₃-BMIM］［HSO₄］/SiO₂的制备及其催化乙酸乙醇酯化反应的研究

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