Remove naphthalene from solvent oil by vinyl imidazole ionic liquid and β-cyclodextrin

doi:10.16085/j.issn.1000-6613.2019-1111

Abstract

Abstract:

In this experiment, 1-vinyl-3-butylimidazole brominated ionic liquid ([VBIM]Br) and β-cyclodextrin was used to remove naphthalene in the solvent oil. The effects of different single factor conditions on the removal rate of naphthalene in solvent oil under the joint action of [VBIM]Br ionic liquid and β-cyclodextrin were investigated, and the removal process conditions were optimized by response surface analysis. The experimental results showed that: the removal rate of naphthalene by [VBIM]Br ionic liquid combined with β-cyclodextrin was improved by more than 10% compared with that of [VBIM]Br ionic liquid used alone, and the extraction rate reached 90%. The removal rate of simply-recovered ionic liquid was reduced to 80% after 5 repetitions. The removal mechanism of naphthalene was analyzed by infrared and ultraviolet spectroscopy. In coordination with [VBIM]Br ionic liquid, β-cyclodextrin encapsulated naphthaleneis, and achieved the removal of naphthalene from solvent oil.

Key words: solvent oil, naphthalene, [VBIM]Br, β-cyclodextrin, response surface analysis, extraction

摘要：

采用1-乙烯基-3-正丁基溴代咪唑离子液体（[VBIM]Br）为脱除剂，在β-环糊精协同作用下萃取溶剂油中的萘。本实验考察了不同单因素条件在[VBIM]Br离子液体与β-环糊精共同作用下对溶剂油中脱萘率的影响，同时通过响应面法优化脱除工艺条件。实验结果表明：[VBIM]Br离子液体与β-环糊精共同作用下对萘的萃取率比单独利用[VBIM]Br离子液体提高了15%以上，萃取率达到90%以上。离子液体简单回收后，重复使用5次过后，脱除率仍在80%以上。实验通过红外分析和紫外光谱分析了[VBIM]Br离子液体协同β-环糊精脱萘的机理，与[VBIM]Br离子液体协同作用下，β-环糊精对萘存在包合作用，实现了对溶剂油中萘的脱除。

关键词: 溶剂油, 萘, 1-乙烯基-3-正丁基溴代咪唑离子液体, β-环糊精, 响应面, 萃取

CLC Number:

TQ028.3⁺2

Entian LI,Yang XU,Pei YAO,Yuanyuan ZHU,Yihan ZHANG,Xiashi ZHU. Remove naphthalene from solvent oil by vinyl imidazole ionic liquid and β-cyclodextrin[J]. Chemical Industry and Engineering Progress, 2020, 39(4): 1321-1328.

李恩田,徐洋,姚培,朱媛媛,张怿涵,朱霞石. β-环糊精协同乙烯基咪唑离子液体脱除溶剂油中的萘[J]. 化工进展, 2020, 39(4): 1321-1328.

Figures/Tables 12

References 31

1	童浩. 离子液体萃取分离芳烃/脂肪烃的研究[D]. 北京: 中国石油大学(北京), 2016.
	TONG H. Separation of aromatic and aliphatic hydrocarbon by ionic liquid[D]. Beijing: China University of Petroleum (Beijing), 2016.
2	孔德金, 杨为民. 芳烃生产技术进展[J]. 化工进展, 2011, 30(1): 16-25.
	KONG D J, YANG W M. Advance in technology for production of aromatic hydrocarbons[J]. Chemical Industry and Engineering Progress, 2011, 30(1): 16-25.
3	WEISSERMEL K, ARPE H J. Industrial organic chemistry[M]. Weinheim: Wiley-VCH, 2003: 313-336.
4	MEINDERSMA G W, HANSMEIER A R, DE HAAN A B. Ionic liquids for aromatics extraction present status and future outlook[J]. Industrial & Engineering Chemistry Research, 2010, 49(16): 7530-7540.
5	ANTHONY J L, BRENNECKE J F, HOLBREY J D, et al. Physicochemical properties of ionic liquids[M]. Weinheim: Wiley-VCH Verlag, 2002: 41-126.
6	KHAN Z H, DOND K, YONG C, et al. Ionic liquids based fluorination of organic compounds using electrochemical method[J]. Journal of Industrial and Engineering Chemistry, 2015, 31: 26-38.
7	MUHAMMAD N, MAN Z, MUTALIB M I A. Dissolution and separation of wood biopolymers using ionic liquids[J]. ChemBioEng Reviews, 2015, 2(4): 257-278.
8	周兆骞. 离子液体脱除柴油中氮化物的研究[D]. 抚顺: 辽宁石油化工大学, 2017.
	ZHOU Z Q. Study on removal of nitrogen compounds from fuel oil by ionic liquid[D]. Fushun: Liaoning Shihua University, 2017.
9	DOMÍNGUEZ I, GONZÁLEZ E J, DOMÍNGUEZ A. Liquid extraction of aromatic/cyclic aliphatic hydrocarbon mixtures using ionic liquids as solvent: literature review and new experimental LLE data[J]. Fuel Processing Technology, 2014, 125: 207-216.
10	FERREIRA A R, FREIRE M G, RIBEIRO J C. Overview of the liquid-liquid equilibria of ternary systems composed of ionic liquid and aromatic and aliphatic hydrocarbons, and their modeling by COSMO-RS[J]. Industrial & Engineering Chemistry Research, 2012, 51(8): 3483-3507.
11	曾昭容, 丁立, 彭勇. 用于芳烃/烷烃体系蒸汽渗透分离的离子液体支撑液膜研究[J]. 高校化学工程学报, 2009, 23(5): 762-767.
	ZENG Z R, DING L, PENG Y. Separation of aromatic hydrocarbon/alkane mixtures using supported liquid membrane with ionic liquids [J]. Journal of Chemical Engineering of Chinese Universities, 2009, 23(5): 762-767.
12	冯浩. 离子液体支撑液膜分离甲苯和正庚烷的研究[D]. 北京: 北京化工大学, 2012.
	FENG H. Study on the separation of toluene/n-heptane by supported liquid membrane with ionic liquid[D]. Beijing: Beijing University of Chemical Technology, 2012.
13	ZHANG J, HUANG C, CHEN B. Extraction of aromatic hydrocarbons from aromatic/aliphatic mixtures using chloroaluminate room-temperature ionic liquids as extractants[J]. Energy & Fuels, 2007, 21(3): 1724-1730.
14	CALVAR N, IRENE DOMÍNGUE Z, ELENA GÓME Z, et al. Separation of binary mixtures aromatic aliphatic using ionic liquids: influence of the structure of the ionic liquid, aromatic and aliphatic[J]. Chemical Engineering Journal, 2011, 175: 213-221.
15	CALAVAR N, DOMÍNGUEZ Z, IREN E, et al. Evaluation of ionic liquids as solvent for aromatic extraction: experimental, correlation and COSMO-RS predictions[J]. The Journal of Chemical Thermodynamics, 2013, 67: 5-12.
16	MEINDERSMA G W, DE HAAN A B. Cyano-containing ionic liquids for the extraction of aromatic hydrocarbons from an aromatic/aliphatic mixture[J]. Science China: Chemistry, 2012, 55(8): 1488-1499.
17	MEINDERSMA G W, PODT A, DE HAAN A B.Selection of ionic liquids for the extraction of aromatic hydrocarbons from aromatic/aliphatic mixtures[J]. Fuel Processing Technology, 2005, 87(1): 59-70.
18	CIOLINO L A, DORSEY J G. Silica-based room temperature phosphorescence substrates: wide dynamic ranges, low backgroundand programmable figures of merit[J]. Analytical Chemistry, 1994, 66(19): 3223-3232.
19	郑炳云, 傅明连, 彭黎波, 等. 溴化1-乙烯基-3-烷基咪唑离子液体/环氧丙烯酸酯阻燃涂层性能研究[J].涂料工业, 2019, 49(1): 13-17.
	ZHENG B Y, FU M L, PENG L B, et al. Properties of flame retardant coatings based on 1-vinyl-3-alkylimidazole brominated ionic liquid/epoxy acrylate[J]. Paint & Coatings Industry, 2019, 49(1): 13-17.
20	邢其毅. 基础有机化学[M]. 第3版. 北京: 高等教育出版社, 2005: 385-374.
	XING Q Y. Basic organic chemistry[M]. 3rd edition. Beijing: Higher Education Press, 2005: 385-374.
21	李晓倩, 管萍, 胡小玲,等. 溴化1-乙烯基-3-烷基咪唑离子液体的电化学性能[J]. 化工学报, 2013, 64(11): 4153-4160.
	LI X Q, GUAN P, HU X L, et al. Electrochemical properties of 1-vinyl-3-alkylimidazole bromide ionic liquids[J]. CIESC Journal, 2013, 64(11) :4153-4160.
22	赵亚梅, 李春阳, 郑长征, 等. 溴化1-乙烯基-3-正丁基咪唑功能化离子液体的合成及其聚合性、导电性等研究[J]. 应用化工, 2015, 44(6): 1163-1165.
	ZHAO Y M, LI C Y, ZHENG C Z, et al. Study on synthesis, polymerizability and conductivity of 1-vinyl-3-butylimidazole bromide[J]. Applied Chemical Industry, 2015, 44(6): 1163-1165.
23	刘春雨. 基于大环化合物的新型交联改性渗透汽化膜构建及其性能研究[D]. 天津: 天津工业大学, 2015.
	LIU C Y. Construction and properties of new crosslinked modified pervaporation membrane based on macrocyclic compounds[D]. Tianjin: Tiangong University, 2015.
24	ZHOU J, MAO J, ZHANG S. Ab initio calculations of the interaction between thiophene and ionic liquids[J]. Fuel Processing Technology, 2008, 89(12): 1456-1460.
25	HOSSAIN M A, LEE J S, KIM D M, et al. Ionic liquids as benign solvents for the extraction of aromatics[J]. Bulletin of the Korean Chemical Society, 2012, 33(10): 3241-3247.
26	KAISY A G M J AL, MUTALIB M L A, BUSTAM M A, et al. Liquid-liquid extraction of aromatics and sulfur compounds from base oil using ionic liquids[J]. Journal of Environmental Chemical Engineering, 2016, 4(4): 4786-4793.
27	王伟. 环糊精接枝滤纸固相脱除室温磷光技术的研究与应用[D]. 北京: 首都师范大学, 2009.
	WANG W. Study and application of solid phase removal at room temperature by grafting filter paper with cyclodextrin[D]. Beijing: Capital Normal University, 2009.
28	DONG J, XIN W, LI S. Desulfurization performance of [BMIM]Br_1-_xFeCl₂ ionic liquid[J]. Journal of East China University of Science and Technology(Natural Science Edition), 2010, 36(3): 356-359.
29	HARPER J B, LYNDEN-BELL R M. Macroscopic and microscopic properties of solutions of aromatic compounds in an ionic liquid[J]. Molecular Physics, 2004, 102(1): 10.
30	PEREIRO A B, ARAÚJO J M M, ESPERANÇ A, et al. Ionic liquids in separations of azeotropic systems: a review[J]. The Journal of Chemical Thermodynamics, 2012, 46:2-28.
31	ZARZYCKI P K, LAMPARCZYK H. The equilibrium constant of β-cyclodextrin-phenolphtalein complex; influence of temperature and tetrahydrofuran addition[J]. Journal of Pharmaceutical and Biomedical Analysis, 1998, 18(1/2):165-170.

方差来源	平方和	自由度	均方	F值	P值 Prob＞F	显著性
模型	1191.99	9	132.44	67.29	＜0.0001	极显著
剂油比（A）	654.68	1	654.68	332.64	＜0.0001	极显著
β-环糊精（B）/g·(10mL)^-1	12.25	1	12.25	6.22	0.041	显著
温度（C）/℃	5.83	1	5.83	2.96	0.129	不显著
AB	5.29	1	5.29	2.69	0.145	不显著
AC	16.93	1	16.93	8.60	0.022	显著
BC	1.88	1	1.88	0.95	0.361	不显著
A²	76.49	1	76.49	38.87	0.0004	显著
B²	385.20	1	385.20	195.72	< 0.0001	极显著
C²	4.66	1	4.66	2.37	0.168	不显著
残差	13.78	7	1.97	—	—	—
失拟项	11.45	3	3.82	6.56	0.0504
纯误差	2.33	4	0.58	—	—	—

方差来源	平方和	自由度	均方	F值	P值 Prob＞F	显著性
模型	1191.99	9	132.44	67.29	＜0.0001	极显著
剂油比（A）	654.68	1	654.68	332.64	＜0.0001	极显著
β-环糊精（B）/g·(10mL)^-1	12.25	1	12.25	6.22	0.041	显著
温度（C）/℃	5.83	1	5.83	2.96	0.129	不显著
AB	5.29	1	5.29	2.69	0.145	不显著
AC	16.93	1	16.93	8.60	0.022	显著
BC	1.88	1	1.88	0.95	0.361	不显著
A²	76.49	1	76.49	38.87	0.0004	显著
B²	385.20	1	385.20	195.72	< 0.0001	极显著
C²	4.66	1	4.66	2.37	0.168	不显著
残差	13.78	7	1.97	—	—	—
失拟项	11.45	3	3.82	6.56	0.0504
纯误差	2.33	4	0.58	—	—	—

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