ZIFs椭圆形孔窗的精细调控及糠醛/5-羟甲基糠醛吸附分离性能研究

doi:10.11949/0438-1157.20201071

摘要/Abstract

摘要：

在生物质催化炼制呋喃化合物的过程中，通常得到的是低浓度糠醛（Fur）和5-羟甲基糠醛（5-HMF）的混合物。基于Fur和5-HMF都是椭圆形分子，因此通过设计构筑和调控椭圆形孔窗的吸附剂可以实现Fur和5-HMF的筛分分离。选用二价钴盐和三种烷基取代基团逐渐增大的咪唑配体（2-乙基咪唑/2-eIm、2-丙基咪唑/2-pIm和2-丁基咪唑/2-bIm）合成了三种椭圆形孔窗尺寸逐渐减小的ANA拓扑ZIFs材料：ANA-[Co(eIm)₂]、ANA-[Co(pIm)₂]和ANA-[Co(bIm)₂]。首先解析了这三种ZIFs材料的晶体结构，并对其进行了PXRD、水蒸气吸附、N₂吸脱附和SEM等基本表征，然后采用静态吸附和动态柱吸附研究了这三种材料对Fur和5-HMF的吸附分离性能。静态吸附、单组分动态柱吸附以及综合速率模型模拟计算结果显示：ANA-[Co(pIm)₂]狭窄的椭圆形孔窗与Fur分子尺寸接近，但小于5-HMF，使得Fur分子可以吸附进入椭圆形孔窗，而5-HMF分子几乎不能通过。进一步在双组分Fur/5-HMF（5%/5%，质量分数）动态柱吸附中，ANA-[Co(pIm)₂]对Fur的吸附量为91.7 mg·g^-1，不吸附5-HMF。因此，通过改变咪唑配体取代基团精细调控ZIFs椭圆形孔窗尺寸，并利用ZIFs椭圆形孔窗的位阻效应实现了Fur和5-HMF的筛分分离。

关键词: 沸石咪唑酯骨架材料, 糠醛, 5-羟甲基糠醛, 吸附, 分离, 回收

Abstract:

In the process of refining furan compounds through biomass catalysis, a mixture of low concentration furfural (Fur) and 5-hydroxymethylfurfural (5-HMF) aqueous solution is usually obtained. Based on the fact that both Fur and 5-HMF are elliptical molecules, the sieving separation of Fur and 5-HMF can be achieved by designing and adjusting the elliptical windows of the adsorbents. In this paper, we used divalent cobalt salts and three imidazole ligands with gradually increasing alkyl substituent groups (2-ethylimidazole/2-eIm, 2-propylimidazole/2-pIm and 2-butylimidazole/2-bIm) to synthesize three ANA topology ZIFs materials with gradually decreasing elliptical windows: ANA-[Co(eIm)₂], ANA-[Co(pIm)₂] and ANA-[Co(bIm)₂]. Firstly, the crystal structures of these three ZIFs were analyzed, and basic characterizations such as PXRD, water vapor adsorption, N₂ adsorption and desorption, and SEM were performed, and then batch adsorption and dynamic column adsorption were used to study the adsorptive separation performance of the three materials for Fur and 5-HMF. The results of batch adsorption, single-component dynamic column adsorption and general rate model simulation calculations show that: narrow and elliptical window of ANA-[Co(pIm)₂] is close to the Fur molecular size, but smaller than 5-HMF, so that Fur molecular can be adsorbed into the elliptical windows, while 5-HMF molecular is hardly adsorbed and cannot pass through. Furthermore, the adsorption capacity of ANA-[Co(pIm)₂] for Fur in the binary-component Fur/5-HMF (5%/5%,mass ratio) dynamic column adsorption is 91.7 mg·g^-1, and 5-HMF is not adsorbed. Therefore, by changing the imidazole ligand substituent groups, the size of the elliptical windows of ZIFs was finely adjusted, and the steric hindrance effect of the elliptical windows of ZIFs was used to achieve the sieve separation of Fur and 5-HMF.

Key words: zeolitic imidazolate frameworks, furfural, 5-hydroxymethylfurfural, adsorption, separation, recovery

中图分类号:

TQ 028.3

赵宇, 石琪, 董晋湘. ZIFs椭圆形孔窗的精细调控及糠醛/5-羟甲基糠醛吸附分离性能研究[J]. 化工学报, 2021, 72(1): 555-568.

ZHAO Yu, SHI Qi, DONG Jinxiang. Fine adjustment of elliptical windows of ZIFs and performances of adsorptive separation of furfural/5-hydroxymethylfurfural[J]. CIESC Journal, 2021, 72(1): 555-568.

图/表 15

图1 ZIFs材料椭圆形孔窗的精细调控及Fur/5-HMF的吸附分离示意图

Fig.1 The fine adjustment of the elliptical windows of ZIFs based on adsorptive separation of Fur/5-HMF

表1 ZIFs材料的晶体结构参数

Table 1 Crystal structure parameters of ZIFs materials

ZIFs

(CCDC number)

Cell parameter

a /?

Density/

(g·cm^-3)

Window/?²

S_BET /

(m²·g^-1)

Pore volume/(cm³·g^-1)

ANA-[Co(eIm)₂]

(2017658)

C₁₀H₁₄CoN₄

249.18

cubic

I a 3 ˉ d

ANA-[Co(pIm)₂]

(2017659)

C₁₂H₁₈CoN₄

277.23

cubic

I a 3 ˉ d

ANA-[Co(bIm)₂]

(2017657)

C₁₄H₂₂CoN₄

305.28

cubic

I a 3 ˉ d

表1 ZIFs材料的晶体结构参数

Table 1 Crystal structure parameters of ZIFs materials

ZIFs

(CCDC number)

Empirical formula

Molecular weight

Crystal system

Space group

Cell parameter

a /?

Density/

(g·cm^-3)

Window/?²

S_BET /

(m²·g^-1)

Pore volume/(cm³·g^-1)

ANA-[Co(eIm)₂]

(2017658)

C₁₀H₁₄CoN₄

249.18

cubic

I a 3 ˉ d

26.581(2)

1.058

7.4×4.9/4.2

610

0.268

ANA-[Co(pIm)₂]

(2017659)

C₁₂H₁₈CoN₄

277.23

cubic

I a 3 ˉ d

26.606(2)

1.173

7.5×3.1/4.2

333

0.139

ANA-[Co(bIm)₂]

(2017657)

C₁₄H₂₂CoN₄

305.28

cubic

I a 3 ˉ d

26.340(3)

1.332

7.5×1.3/4.1

—

图2 ANA-[Co(eIm)2]，ANA-[Co(pIm)2]和ANA-[Co(bIm)2]的基本表征

Fig.2 The basic characterizations of ANA-[Co(eIm)2], ANA-[Co(pIm)2] and ANA-[Co(bIm)2]

图3 ZIFs材料的SEM图和造粒形貌图

Fig.3 SEM images and particles pictures of ZIFs

图4 25℃下ZIFs对单组分Fur和5-HMF的静态吸附等温线（误差棒对应每个点的标准偏差）

Fig.4 Static adsorption isotherms of ZIFs for single-component Fur and 5-HMF at the temperature of 25℃ (Error bars correspond to the standard deviation at each point)

表2 Langmuir和Freundlich吸附模型对单组分静态吸附拟合的结果

Table 2 Langmuir adsorption and Freundlich adsorption model for single-component batch adsorption fitting results

ZIFs	Langmuir model						Freundlich model
	Fur			5-HMF			Fur			5-HMF
	K_L/ (L·mg^-1)	q_max/(mg·g^-1)	R²	K_L/ (L·mg^-1)	q_max/(mg·g^-1)	R²	K_F/(mg·g^-1)	n	R²	K_F/ (mg·g^-1)	n	R²
ANA-[Co(eIm)₂]	3.144	271.8	0.981	0.367	318.1	0.981	176.153	3.108	0.841	79.946	1.569	0.941
ANA-[Co(pIm)₂]	0.622	145.2	0.991	0.344	9.2	0.901	52.038	1.968	0.952	2.376	1.710	0.942
ANA-[Co(bIm)₂]	0.064	44.1	0.950	1.014	3.1	0.958	2.672	1.145	0.945	1.403	2.263	0.937

图5 25℃下ZIFs对单组分Fur和5-HMF的动态穿透曲线（填料层：25 cm；柱径：0.4 cm；流量：0.05 ml·min-1）

Fig.5 Breakthrough curves of single-component Fur and 5-HMF on ZIFs at the temperature of 25℃ (length: 25 cm; diameter: 0.4 cm; rate: 0.05 ml·min-1)

表3 综合速率模型对单组分动态柱吸附的拟合结果

Table 3 Fitting results of the general rate model (GRM) for single-component dynamic column adsorption

GRM parameter	ANA-[Co(eIm)₂]		ANA-[Co(pIm)₂]		ANA-[Co(bIm)₂]
GRM parameter	Fur	5-HMF	Fur	5-HMF	Fur	5-HMF
D_ax /(cm²·min^-1)	5.730×10^-4	1.567×10^-4	4.820×10^-4	1.773×10^-4	1.720×10^-4	4.675×10^-4
K_film/(cm·min^-1)	2.740×10^-2	2.360×10^-2	3.510×10^-2	1.350×10^-2	3.490×10^-2	1.900×10^-2
D_pore /(cm²·min^-1)	2.176×10^-3	2.054×10^-4	1.534×10^-3	8.035×10^-5	8.712×10^-5	8.006×10^-5

表4 单组分静态吸附和动态柱吸附的吸附量汇总

Table 4 Summary of adsorption capacity of single-component batch adsorption and dynamic column adsorption

Item	ANA-[Co(eIm)₂] /(mg·g^-1)				ANA-[Co(pIm)₂] /(mg·g^-1)				ANA-[Co(bIm)₂]/(mg·g^-1)
	2%		5%		2%		5%		2%		5%
	Fur	5-HMF	Fur	5-HMF	Fur	5-HMF	Fur	5-HMF	Fur	5-HMF	Fur	5-HMF
single-component batch adsorption	222.3	129.3	251.4	190.8	77.7	3.3	105.1	6.5	4.4	1.9	10.1	2.8
dynamic column adsorption
single	212.8	125.8	245.3	195.8	76.5	3.9	93.8	7.3	4.2	0.1	9.9	1.5
binary	208.9	2.7	239.1	2.3	77.1	—	91.7	—	4.1	—	9.1	—

图6 25℃下ZIFs对双组分Fur/5-HMF的动态穿透曲线（填料层：25 cm；柱径：0.4 cm；流量：0.05 ml·min-1）

Fig.6 Breakthrough curves of binary-component Fur/5-HMF diluted in water on ZIFs at the temperature of 25℃(length: 25 cm; diameter: 0.4 cm; rate: 0.05 ml·min-1)

图7 不同流量下ANA-[Co(pIm)2]对双组分Fur/5-HMF（5%/5%）的动态柱吸脱附曲线（填料层：33 cm，柱径：0.6 cm，吸附温度：25℃，脱附温度：40℃;误差棒对应每个点的标准偏差）

Fig.7 Adsorption-desorption breakthrough curves of binary-component Fur/5-HMF (5%/5%) diluted in water on ANA-[Co(pIm)2] at different flow rates (length: 33 cm, diameter: 0.6 cm, adsorption temperature: 25℃, desorption temperature: 40℃; error bars correspond to the standard deviation at each point)

图8 0.1 ml·min-1流量下ANA-[Co(pIm)2]对双组分Fur/5-HMF（5%/5%）循环5次的动态柱吸脱附曲线（填料层：33 cm，柱径：0.6 cm，吸附温度：25℃，脱附温度：40℃）

Fig.8 Adsorption-desorption breakthrough curves of binary-component Fur/5-HMF (5%/5%) diluted in water on ANA-[Co(pIm)2] in 5 adsorption-desorption cycles at a flow rate of 0.1 ml·min-1 (length: 33 cm, diameter: 0.6 cm, adsorption temperature: 25℃, desorption temperature: 40℃)

图9 ZIFs材料吸附Fur和5-HMF前后和溶剂再生后的PXRD图

Fig.9 PXRD patterns of ZIFs before and after adsorption Fur and 5-HMF and solvent regeneration

图10 25℃下ZSM-5和ANA-[Co(pIm)2]对双组分Fur/5-HMF（5%/5%）的动态穿透曲线（填料层：25 cm；柱径：0.4 cm，流量：0.05 ml·min-1）

Fig.10 Breakthrough curves of binary-component Fur/5-HMF (5%/5%) diluted in water on ZSM-5 and ANA-[Co(pIm)2] at the temperature of 25℃(length: 25 cm, diameter: 0.4 cm, rate: 0.05 ml·min-1)

表5 ZSM-5，MAF-5[21]，ANA-[Co(eIm)2]和ANA-[Co(pIm)2]的动态柱吸附量和吸附选择性汇总

Table 5 Summary of adsorption capacity and selectivity of dynamic column adsorption for ZSM-5, MAF-5[21], ANA-[Co(eIm)2] and ANA-[Co(pIm)2]

Adsorbent	q_Fur/(mg·g^-1)	q_5-HMF /(mg·g^-1)	S_Fur,5-HMF
ZSM-5	112.7	30.1	3.7
MAF-5	220.0	1.9	115.8
ANA-[Co(eIm)₂]	239.1	2.3	104.0
ANA-[Co(pIm)₂]	91.7	—	—

参考文献 35

1	Ragauskas A J, Williams C K, Davison B H, et al. The path forward for biofuels and biomaterials[J]. Science, 2006, 311(5760): 484-489.
2	Zhang X G, Wilson K, Lee A F. Heterogeneously catalyzed hydrothermal processing of C₅-C₆ sugars[J]. Chemical Reviews, 2016, 116(19): 12328-12368.
3	Bozell J J, Petersen G R. Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy's “Top 10” revisited[J]. Green Chemistry, 2010, 12(4): 539-554.
4	Xu S Q, Pan D H, Wu Y F, et al. Direct conversion of wheat straw components into furan compounds using a highly efficient and reusable SnCl₂-PTA/β zeolite catalyst[J]. Industrial & Engineering Chemistry Research, 2019, 58(22): 9276-9285.
5	Widsten P, Murton K, West M. Production of 5-hydroxymethylfurfural and furfural from a mixed saccharide feedstock in biphasic solvent systems[J]. Industrial Crops & Products, 2018, 119: 237-242.
6	聂一凡, 候其东, 李维尊, 等. 糠醛的水解制备和应用研究进展[J]. 化工进展, 2019, 38(5): 2164-2178.
	Nie Y F, Hou Q D, Li W Z, et al. Advances in production furfural via hydrolysis and application of furfural[J]. Chemical Industry and Engineering Progress, 2019, 38(5): 2164-2178.
7	van Putten R J, van der Waal J C, de Jong E D, et al. Hydroxymethylfurfural, a versatile platform chemical made from renewable resources[J]. Chemical Reviews, 2013, 113(3): 1499-1597.
8	Zhang K, Agrawal M, Harper J, et al. Removal of the fermentation inhibitor, furfural, using activated carbon in cellulosic-ethanol production[J]. Industrial & Engineering Chemistry Research, 2011, 50(24): 14055-14060.
9	Rajabbeigi N, Ranjan R, Tsapatsis M, et al. Selective adsorption of HMF on porous carbons from fructose/DMSO mixtures[J]. Microporous and Mesoporous Materials, 2012, 158: 253-256.
10	Jia X M, Li X Y, Liu Z, et al. Adsorption process and mechanism for furfural separation with macroporous resin[J]. Desalination and Water Treatment, 2014, 56(8): 1-11.
11	Ijzer A C, Vriezekolk E, Rolevink E, et al. Performance analysis of aromatic adsorptive resins for the effective removal of furan derivatives from glucose[J]. Journal of Chemical Technology & Biotechnology, 2015, 90(1): 101-109.
12	Anbia M, Mohammadi N. A nanoporous adsorbent for removal of furfural from aqueous solutions[J]. Desalination, 2009, 249(1): 150-153.
13	Ranjan R, Thust S, Gounaris C E, et al. Adsorption of fermentation inhibitors from lignocellulosic biomass hydrolyzates for improved ethanol yield and value-added product recovery[J]. Microporous and Mesoporous Materials, 2009, 122(1): 143-148.
14	Huang X C, Lin Y Y, Zhang J P, et al. Ligand-directed strategy for zeolite-type metal-organic frameworks: zinc (II) imidazolates with unusual zeolitic topologies[J]. Angewandte Chemie International Edition, 2006, 45(10): 1557-1559.
15	Banerjee R, Phan A, Wang B, et al. High-throughput synthesis of zeolitic imidazolate frameworks and application to CO₂ capture[J]. Science, 2008, 319(5865): 939-943.
16	Li J R, Sculley J P, Zhou H C. Metal-organic frameworks for separations[J]. Chemical Reviews, 2012, 112(2): 869-932.
17	王可可, 李亮莎, 黄宏亮, 等. 铪金属-有机骨架材料的孔尺寸调控及其吸附性能[J]. 化工学报, 2014, 65(5): 1696-1705.
	Wang K K, Li L S, Huang H L, et al. Control of pore size in Hf-based metal-organic frameworks and exploration of their adsorption properties[J]. CIESC Journal, 2014, 65(5): 1696-1705.
18	高春苹, 石琪, 董晋湘.憎水性金属多氮唑骨架材料(MAF-6)对糠醛/水吸附分离性能的研究[J].化工进展, 2017, 36(9): 3429-3435.
	Gao C P, Shi Q, Dong J X. Study of the adsorptive separation performance of hydrophobic metal azolate framework(MAF-6) for furfural/water system[J]. Chemical Industry and Engineering Progress, 2017, 36(9): 3429-3435.
19	Jin H, Li Y S, Liu X L, et al. Recovery of HMF from aqueous solution by zeolitic imidazolate frameworks[J]. Chemical Engineering Science, 2015, 124: 170-178.
20	Baerlocher C, McCusker L B, Olson D H. Atlas of Zeolite Framework Types[M]. Elsevier, 2007.
21	Zhao Y, Xu J, Wang J, et al. Adsorptive separation of furfural/5-hydroxymethylfurfural in MAF-5 with ellipsoidal pores[J]. Industrial & Engineering Chemistry Research, 2020, 59 (25): 11734-11742.
22	Jin H, Li Y S, Yang W S. Adsorption of biomass-derived polyols onto metal-organic frameworks from aqueous solutions[J]. Industrial & Engineering Chemistry Research, 2018, 57(35): 11963-11969.
23	Langmuir I. The adsorption of gases on plane surfaces of glass, mica and platinum[J]. Journal of the American Chemical Society, 1918, 40(9): 1361-1403.
24	Foo K Y, Hameed B H. Insights into the modeling of adsorption isotherm systems[J]. Chemical Engineering Journal, 2010, 156(1): 2-10.
25	Schute K, Louven Y, Detoni C, et al. Selective liquid phase adsorption of biogenic HMF on hydrophobic spherical activated carbons[J]. Chemie Ingenieur Technik, 2016, 88(3): 355-362.
26	Yang Q, Runge T. Cross-linked polyethylenimine for selective adsorption and effective recovery of lignocellulose-derived organic acids and aldehydes[J]. ACS Sustainable Chemistry & Engineering, 2018, 7(1): 933-943.
27	Zheng J Y, Pan B Y, Xiao J X, et al. Experimental and mathematical simulation of noncompetitive and competitive adsorption dynamic of formic acid-levulinic acid-5- hydroxymethylfurfural from single, binary, and ternary systems in a fixed-bed column of SY-01 resin[J]. Industrial & Engineering Chemistry Research, 2018, 57: 8518-8528.
28	Zhu A X, Lin R B, Qi X L, et al. Zeolitic metal azolate frameworks (MAFs) from ZnO/Zn(OH)₂ and monoalkyl-substituted imidazoles and 1, 2, 4-triazoles: efficient syntheses and properties[J]. Microporous and Mesoporous Materials, 2012, 157: 42-49.
29	李长海, 石洪仁, 唐洪宇.弱碱性树脂处理β-萘磺酸废水的吸附分离热力学性能[J].化工学报, 2004, 55(7): 1117-1123.
	Li C H, Shi H R, Tang H Y. Adsorption separation of β-naphthalenesulphonic acid wastewater on weakly basic resin and thermodynamics [J]. Journal of Chemical Industry and Engineering(China), 2004, 55(7): 1117-1123.
30	Sulaymon A H, Ahmed K W. Competitive adsorption of furfural and phenolic compounds onto activated carbon in fixed bed column[J]. Environmental Science & Technology, 2008, 42(2): 392-397.
31	Lin X Q, Qi G X, Shi S L, et al. Estimation of fixed-bed column parameters and mathematical modeling of breakthrough behaviors for adsorption of levulinic acid from aqueous solution using SY-01 resin[J]. Separation and Purification Technology, 2017, 174: 222-231.
32	Lin X Q, Wu J L, Jin X H, et al. Selective separation of biobutanol from acetone-butanol-ethanol fermentation broth by means of sorption methodology based on a novel macroporous resin[J].Biotechnology Progress, 2012, 28(4): 962-972.
33	尚华, 白洪灏, 刘佳奇, 等. CH₄-N₂在自支撑颗粒型Silicalite-1上的吸附分离及PSA模拟[J]. 化工学报, 2020, 71(5): 2088-2098.
	Shang H, Bai H H, Liu J Q, et al. PSA simulation and adsorption separation of CH₄-N₂ by self-supporting pellets Silicalite-1[J]. CIESC Journal, 2020, 71(5): 2088-2098.
34	Weil J, Dien B S, Bothast R J, et al. Removal of fermentation inhibitors formed during pretreatment of biomass by polymeric adsorbents[J]. Industrial & Engineering Chemistry Research, 2002, 41(24): 6132-6138.
35	Schute K, Louven Y, Detoni C, et al. Selective liquid phase adsorption of biogenic HMF on hydrophobic spherical activated carbons[J]. Chemie Ingenieur Technik, 2016, 88(3): 355-362.

[1]	晁京伟, 许嘉兴, 李廷贤. 基于无管束蒸发换热强化策略的吸附热池的供热性能研究[J]. 化工学报, 2023, 74(S1): 302-310.
[2]	黄琮琪, 吴一梅, 陈建业, 邵双全. 碱性电解水制氢装置热管理系统仿真研究[J]. 化工学报, 2023, 74(S1): 320-328.
[3]	杨学金, 杨金涛, 宁平, 王访, 宋晓双, 贾丽娟, 冯嘉予. 剧毒气体PH₃的干法净化技术研究进展[J]. 化工学报, 2023, 74(9): 3742-3755.
[4]	赵亚欣, 张雪芹, 王荣柱, 孙国, 姚善泾, 林东强. 流穿模式离子交换层析去除单抗聚集体[J]. 化工学报, 2023, 74(9): 3879-3887.
[5]	郑佳丽, 李志会, 赵新强, 王延吉. 离子液体催化合成2-氰基呋喃反应动力学研究[J]. 化工学报, 2023, 74(9): 3708-3715.
[6]	高燕, 伍鹏, 尚超, 胡泽君, 陈晓东. 基于双流体喷嘴的磁性琼脂糖微球的制备及其蛋白吸附性能探究[J]. 化工学报, 2023, 74(8): 3457-3471.
[7]	刘爽, 张霖宙, 许志明, 赵锁奇. 渣油及其组分黏度的分子层次组成关联研究[J]. 化工学报, 2023, 74(8): 3226-3241.
[8]	张佳怡, 何佳莉, 谢江鹏, 王健, 赵鹬, 张栋强. 渗透汽化技术用于锂电池生产中N-甲基吡咯烷酮回收的研究进展[J]. 化工学报, 2023, 74(8): 3203-3215.
[9]	盛冰纯, 于建国, 林森. 铝基锂吸附剂分离高钠型地下卤水锂资源过程研究[J]. 化工学报, 2023, 74(8): 3375-3385.
[10]	张瑞航, 曹潘, 杨锋, 李昆, 肖朋, 邓春, 刘蓓, 孙长宇, 陈光进. ZIF-8纳米流体天然气乙烷回收工艺的产品纯度关键影响因素分析[J]. 化工学报, 2023, 74(8): 3386-3393.
[11]	邢雷, 苗春雨, 蒋明虎, 赵立新, 李新亚. 井下微型气液旋流分离器优化设计与性能分析[J]. 化工学报, 2023, 74(8): 3394-3406.
[12]	文兆伦, 李沛睿, 张忠林, 杜晓, 侯起旺, 刘叶刚, 郝晓刚, 官国清. 基于自热再生的隔壁塔深冷空分工艺设计及优化[J]. 化工学报, 2023, 74(7): 2988-2998.
[13]	王杰, 丘晓琳, 赵烨, 刘鑫洋, 韩忠强, 许雍, 蒋文瀚. 聚电解质静电沉积改性PHBV抗氧化膜的制备与性能研究[J]. 化工学报, 2023, 74(7): 3068-3078.
[14]	陈吉, 洪泽, 雷昭, 凌强, 赵志刚, 彭陈辉, 崔平. 基于分子动力学的焦炭溶损反应及其机理研究[J]. 化工学报, 2023, 74(7): 2935-2946.
[15]	张缘良, 栾昕奇, 苏伟格, 李畅浩, 赵钟兴, 周利琴, 陈健民, 黄艳, 赵祯霞. 离子液体复合萃取剂选择性萃取尼古丁的研究及DFT计算[J]. 化工学报, 2023, 74(7): 2947-2956.