离子液体萃取分离烃类化合物的研究进展

doi:10.16085/j.issn.1000-6613.2021-0517

摘要/Abstract

摘要：

溶剂萃取分离技术广泛应用于石油化工领域，为石油石化产品的分离和提纯生产提供了有力的技术支撑。离子液体的结构可设计性、化学稳定性和热稳定性、极低的蒸气压等优点，使其在烃类化合物分离领域受到了研究者广泛关注。本文首先介绍了离子液体的性质及分类，根据分离目标不同，归纳了离子液体在芳烃-饱和烃分离、脱硫脱氮、烯烃-烷烃分离领域取得的最新进展，探讨了离子液体在油品分离领域研究中存在的问题和未来发展方向。文中指出：阳离子烷基侧链和极性是影响其对芳烃萃取效果的关键因素，然而对实际体系芳烃-饱和烃分离还有待进一步研究；离子液体对杂原子含硫含氮化合物均表现出较强的分离能力，但是碱性氮化物和非碱性氮化物不易通过一种离子液体同时脱除；氢键碱性是影响离子液体分离烯烃的关键因素，然而大部分离子液体对烯烃选择性仍然不高。根据不同的分离任务，从分子水平上认识离子液体结构与分离效果的关系，进而设计出兼具高效分离能力和低环境影响的新型离子液体，对提升油品中关键组分的高附加值转化利用具有重要意义。

关键词: 离子液体, 溶剂萃取, 分离, 芳烃, 脱硫脱氮, 烯烃, 分子间相互作用, 石油

Abstract:

Solvent extraction is widely used in the petrochemical industry, which is a powerful technology for the separation and purification of petroleum and petrochemical products. Ionic liquids, as a new type of separation medium, have attracted great attention in recent years, especially in oil extraction and separation due to their advantages such as designable structure, high chemical and thermal stability, and very low vapor pressure. In this paper, the properties and classification of ionic liquids are introduced firstly. Secondly, according to different separation objectives, the latest progress of ionic liquids in the fields of aromatics separation from saturated hydrocarbons, desulfurization and denitrification, separation of olefins from paraffins is summarized. The existing problems and future development directions of ionic liquids in oil separation are discussed. The chain of cationic sides and polarity are the key factors affecting the extraction efficiency of aromatic hydrocarbons. However, the separation of aromatics form saturated hydrocarbons in the real oils needs further study. Ionic liquids show a strong ability to separate heteroatomic sulfur and nitrogen compounds, but it is difficult to remove basic nitrogen and non-basic nitrogen compounds simultaneously by using the same ionic liquid. The alkalinity of hydrogen bond is a key factor affecting the separation of olefins by ionic liquids. However, most ionic liquids have low selectivity to olefins. According to different separation tasks, it is important to understand the relationship between the structure of ionic liquids and their separation performance at molecular level, and then design new ionic liquids with high separation efficiency and low environmental impact, which will maximize the utilization value of the key components in oil.

Key words: ionic liquids, solvent extraction, separation, aromatics, desulfurization and denitrification, olefins, intermolecular interaction, petroleum

中图分类号:

TQ028.3

倪清, 来锦波, 彭东岳, 管翠诗, 龙军. 离子液体萃取分离烃类化合物的研究进展[J]. 化工进展, 2022, 41(2): 619-627.

NI Qing, LAI Jinbo, PENG Dongyue, GUAN Cuishi, LONG Jun. Progress in extraction separation of hydrocarbons by ionic liquids[J]. Chemical Industry and Engineering Progress, 2022, 41(2): 619-627.

图/表 7

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离子液体	温度/K	分离体系	分配系数	选择性	参考文献
1-丁基吡啶四氟硼酸盐	313.2	庚烷+甲苯	0.3~0.4	23.4~74.4	［17］
1-庚基吡啶四氟硼酸盐	313.2	庚烷+甲苯	0.53~0.67	7.4~25.6
1-乙基-3甲基咪唑双三氟甲磺酰亚胺盐	313.2	庚烷+甲苯	0.66~0.88	9.3~37.7	［19］
1-丁基-3甲基咪唑双三氟甲磺酰亚胺盐	313.2	庚烷+甲苯	0.76~1.26	5.9~25.0
1-乙基-3-甲基咪唑甲磺酸盐	313.2	庚烷+甲苯	0.13~0.16	22.0~79.7	［20］
1-乙基-3-甲基咪唑三氟甲烷磺酸盐	313.2	庚烷+甲苯	0.28~0.39	14.5~42.9
1-乙基-3-甲基咪唑四氟乙烷磺酸盐	313.2	庚烷+甲苯	0.25~0.31	16.8~53.8
双（1-乙基-3-甲基咪唑）硫氰钴酸盐	313.2	庚烷+甲苯	0.81~1.28	23.7~68.7	［21］
1-乙基-3-甲基咪唑硫酸氢盐	313.2	庚烷+甲苯	0.03~0.05	23.1~75.4	［29］
1-乙基-3-甲基咪唑硫酸甲酯盐	313.2	庚烷+甲苯	0.2~0.26	17.6~68.1
1，4-双（1-乙基咪唑）己基二双三氟甲磺酰亚胺盐	303.15	环己烷+苯	24.9	2.25	［25］
1-丁基-3-甲基咪唑氯铁酸盐	298.15	环己烷+苯	2.16	11.55	［32］
1-庚基-3-甲基吡啶四氟硼酸盐	313.15	癸烷+丁苯	0.45	49.4	［33］

离子液体	温度/K	分离体系	分配系数	选择性	参考文献
1-丁基吡啶四氟硼酸盐	313.2	庚烷+甲苯	0.3~0.4	23.4~74.4	［17］
1-庚基吡啶四氟硼酸盐	313.2	庚烷+甲苯	0.53~0.67	7.4~25.6
1-乙基-3甲基咪唑双三氟甲磺酰亚胺盐	313.2	庚烷+甲苯	0.66~0.88	9.3~37.7	［19］
1-丁基-3甲基咪唑双三氟甲磺酰亚胺盐	313.2	庚烷+甲苯	0.76~1.26	5.9~25.0
1-乙基-3-甲基咪唑甲磺酸盐	313.2	庚烷+甲苯	0.13~0.16	22.0~79.7	［20］
1-乙基-3-甲基咪唑三氟甲烷磺酸盐	313.2	庚烷+甲苯	0.28~0.39	14.5~42.9
1-乙基-3-甲基咪唑四氟乙烷磺酸盐	313.2	庚烷+甲苯	0.25~0.31	16.8~53.8
双（1-乙基-3-甲基咪唑）硫氰钴酸盐	313.2	庚烷+甲苯	0.81~1.28	23.7~68.7	［21］
1-乙基-3-甲基咪唑硫酸氢盐	313.2	庚烷+甲苯	0.03~0.05	23.1~75.4	［29］
1-乙基-3-甲基咪唑硫酸甲酯盐	313.2	庚烷+甲苯	0.2~0.26	17.6~68.1
1，4-双（1-乙基咪唑）己基二双三氟甲磺酰亚胺盐	303.15	环己烷+苯	24.9	2.25	［25］
1-丁基-3-甲基咪唑氯铁酸盐	298.15	环己烷+苯	2.16	11.55	［32］
1-庚基-3-甲基吡啶四氟硼酸盐	313.15	癸烷+丁苯	0.45	49.4	［33］

离子液体	体系	温度/K	脱除率	参考文献
1-丁基-3-甲基咪唑氯盐	直馏柴油	333.15	含氮量>50%，含硫量<5%	［49］
1-辛基吡啶氯盐	直馏柴油	333.15	含氮量>50%，含硫量<5%	［49］
1-丁基-3-甲基咪唑四氟硼酸盐	正十二烷+苯并噻吩+吡啶+哌啶	303.15	苯并噻吩12%，吡啶45%，哌啶9%	［35］
1-丁基-3-甲基咪唑溴盐-氯化锌	正十二烷+甲苯+喹啉+吲哚	313.15	喹啉94%，吲哚82%	［50］
1-丁基-3-甲基咪唑溴盐-氯化锌	页岩油柴油馏分	343.15	总氮77%	［50］
1-甲基-3-甲基咪唑磷酸二甲酯盐	煤焦油柴油馏分	313.15	碱氮37%，非碱氮50%	［51］
1-丁基-3-甲基咪唑磷酸二乙酯盐	煤焦油柴油馏分	313.15	碱氮36.1%，非碱氮59.7%
1-丁基-3-甲基咪唑磷酸二丁酯盐	煤焦油柴油馏分	313.15	碱氮32.5%，非碱氮58.4%
1-乙基-3-甲基咪唑磷酸二氢盐	煤焦油柴油馏分	313.15	碱氮86.7%，非碱氮60.1%
1-乙基-3-甲基咪唑二氰胺盐	己烷+甲苯+吡啶+咔唑+噻吩+二苯并噻吩	303.15	吡啶69.13%，咔唑100%，噻吩49.2%，二苯并噻吩55.6%	［52］
1-戊基-3-甲基咪唑双三氟甲磺酰亚胺盐	正十二烷+正十六烷+甲苯+吡啶+噻吩+苯并噻吩	303.15	吡啶87.8%，噻吩53.58%，苯并噻吩66.29%	［53］

离子液体	体系	温度/K	脱除率	参考文献
1-丁基-3-甲基咪唑氯盐	直馏柴油	333.15	含氮量>50%，含硫量<5%	［49］
1-辛基吡啶氯盐	直馏柴油	333.15	含氮量>50%，含硫量<5%	［49］
1-丁基-3-甲基咪唑四氟硼酸盐	正十二烷+苯并噻吩+吡啶+哌啶	303.15	苯并噻吩12%，吡啶45%，哌啶9%	［35］
1-丁基-3-甲基咪唑溴盐-氯化锌	正十二烷+甲苯+喹啉+吲哚	313.15	喹啉94%，吲哚82%	［50］
1-丁基-3-甲基咪唑溴盐-氯化锌	页岩油柴油馏分	343.15	总氮77%	［50］
1-甲基-3-甲基咪唑磷酸二甲酯盐	煤焦油柴油馏分	313.15	碱氮37%，非碱氮50%	［51］
1-丁基-3-甲基咪唑磷酸二乙酯盐	煤焦油柴油馏分	313.15	碱氮36.1%，非碱氮59.7%
1-丁基-3-甲基咪唑磷酸二丁酯盐	煤焦油柴油馏分	313.15	碱氮32.5%，非碱氮58.4%
1-乙基-3-甲基咪唑磷酸二氢盐	煤焦油柴油馏分	313.15	碱氮86.7%，非碱氮60.1%
1-乙基-3-甲基咪唑二氰胺盐	己烷+甲苯+吡啶+咔唑+噻吩+二苯并噻吩	303.15	吡啶69.13%，咔唑100%，噻吩49.2%，二苯并噻吩55.6%	［52］
1-戊基-3-甲基咪唑双三氟甲磺酰亚胺盐	正十二烷+正十六烷+甲苯+吡啶+噻吩+苯并噻吩	303.15	吡啶87.8%，噻吩53.58%，苯并噻吩66.29%	［53］

离子液体	温度/K	压力/kPa	体系	选择性	参考文献
1-丁基-3-甲基咪唑三氟甲烷磺酸盐	313	常压	己烯/己烷	1.95	［55］
1-丁基-3-甲基咪唑四氟硼酸盐	313	常压	己烯/己烷	2.6
1-丁基-3-甲基咪唑醋酸盐	313	常压	己烯/己烷	1.86
1-乙基-3-甲基咪唑二氰胺盐	313	常压	己烯/己烷	2.58
1-炔乙基-3-甲基咪唑双三氟甲磺酰亚胺盐	313	60~100	乙烯/乙烷	0.65	［56］
1-氰丙基-3-甲基咪唑二氰胺盐	313	60~100	乙烯/乙烷	0.67
1-丁基-3-甲基咪唑磷酸甲酯盐	313	60~100	乙烯/乙烷	1.45
1-乙基-3-甲基咪唑双三氟甲磺酰亚胺盐	298	常压	环己烯/环己烷	1.9	［57］
1-乙基-3-甲基咪唑三氰基甲烷盐	298	常压	环己烯/环己烷	3
1-苄基-3-甲基咪唑双三氟甲磺酰亚胺盐	298	常压	环己烯/环己烷	1.76
四丁基膦正己酸盐	298	20~160	乙烯/乙炔	21.4	［60］
三己基十四烷基膦醋酸盐	298	20~160	乙烯/乙炔	9.4	［60］
二甲基苯甲酰胺双三氟甲磺酰亚胺银盐	298	100	庚烯/庚烷	5.07	［64］
二甲基苯甲酰胺双三氟甲磺酰亚胺银盐	298	100	辛烯/辛烷	3.39	［64］
盐酸三乙胺-氯化亚铜	303	250	乙烯/乙烷	8.78	［66］