CN114349706A - A kind of hydroxyl functional ionic liquid and preparation method thereof - Google Patents
A kind of hydroxyl functional ionic liquid and preparation method thereof Download PDFInfo
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 51
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- DOVKIDKLMHZZNH-UHFFFAOYSA-M 1-(3-methylimidazol-3-ium-1-yl)ethanol;bromide Chemical compound [Br-].CC(O)N1C=C[N+](C)=C1 DOVKIDKLMHZZNH-UHFFFAOYSA-M 0.000 claims abstract description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- RZNHHGMCDDENDY-UHFFFAOYSA-N 1-(1-methylimidazol-2-yl)ethanol Chemical compound CC(O)C1=NC=CN1C RZNHHGMCDDENDY-UHFFFAOYSA-N 0.000 claims abstract description 7
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims abstract description 7
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 235000019260 propionic acid Nutrition 0.000 claims abstract description 7
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims abstract description 7
- 239000012043 crude product Substances 0.000 claims abstract description 6
- 239000007787 solid Substances 0.000 claims abstract description 6
- 239000003957 anion exchange resin Substances 0.000 claims abstract description 5
- 239000008367 deionised water Substances 0.000 claims abstract description 5
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000011259 mixed solution Substances 0.000 claims abstract description 3
- 238000001035 drying Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- -1 1-hydroxyethyl-3-methylimidazolic acid Chemical compound 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 2
- UZMBZCOTLFXQNJ-UHFFFAOYSA-N [Br].OC(C)C1=NC=CN1C Chemical compound [Br].OC(C)C1=NC=CN1C UZMBZCOTLFXQNJ-UHFFFAOYSA-N 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 238000000967 suction filtration Methods 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 238000001291 vacuum drying Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 3
- 238000001953 recrystallisation Methods 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 101710134784 Agnoprotein Proteins 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- LOKGSQPYZNBSSL-UHFFFAOYSA-N 1h-imidazol-1-ium;propanoate Chemical compound CCC([O-])=O.[NH2+]1C=CN=C1 LOKGSQPYZNBSSL-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical class BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical compound O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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Abstract
本发明涉及离子液体技术领域，具体的涉及一种羟基功能性离子液体及其制备方法。在氮气的保护下，向N‑甲基咪唑中缓慢滴加2‑溴乙醇和甲苯进行反应，反应完成后用无水乙醚反应洗涤数次，得到固体粗产物1‑羟基乙基‑3‑甲基咪唑溴盐；用乙酸乙酯和乙腈的混合溶液溶解固体粗产物，重结晶后抽滤，干燥；向提纯后的1‑羟基乙基‑3‑甲基咪唑溴盐加入去离子水稀释，倒入氢氧型阴离子交换树脂中，反应完成后接取流出液，丙酸加入到氢氧型中间体1‑羟基乙基‑3‑甲基咪唑中，室温下进行搅拌反应，旋转蒸发除去水分，真空干燥，得到目标产物。本发明所述的方法具有着操作简单，成本低，纯度高，稳定性强的优点。The invention relates to the technical field of ionic liquids, in particular to a hydroxyl functional ionic liquid and a preparation method thereof. Under the protection of nitrogen, 2-bromoethanol and toluene were slowly added dropwise to N-methylimidazole to react, and after the reaction was completed, the reaction was washed with anhydrous ether for several times to obtain a solid crude product 1-hydroxyethyl-3-methyl imidazolium bromide; dissolve the solid crude product with a mixed solution of ethyl acetate and acetonitrile, filter with suction after recrystallization, and dry; add deionized water to the purified 1-hydroxyethyl-3-methylimidazolium bromide to dilute, Pour it into the hydroxide-type anion exchange resin, take the effluent after the reaction is completed, add propionic acid to the hydroxide-type intermediate 1-hydroxyethyl-3-methylimidazole, carry out stirring reaction at room temperature, and remove moisture by rotary evaporation , and dried in vacuo to obtain the target product. The method of the invention has the advantages of simple operation, low cost, high purity and strong stability.
Description
技术领域technical field
本发明涉及离子液体技术领域，具体的涉及一种羟基功能性离子液体及其制备方法。The invention relates to the technical field of ionic liquids, in particular to a hydroxyl functional ionic liquid and a preparation method thereof.
背景技术Background technique
离子液体在电化学、催化反应、色谱、有机合成、生物化学、太阳能电池和分离技术等领域有着广泛的应用，并且离子离子液体还有着良好的热稳定性，高导电率和低电化学窗口以及低可燃性、低熔点、低蒸汽压和高离子密度等优异的物理性质。引起了广泛关注和研究。离子液体是指在室温下呈液态的有机盐，这种液态盐由有机阳离子和有机阴离子或者无机阴离子构成。这种呈液态的熔融盐却又不同与其他离子化合物。Ionic liquids have a wide range of applications in electrochemistry, catalytic reactions, chromatography, organic synthesis, biochemistry, solar cells and separation technology, and ionic liquids also have good thermal stability, high conductivity and low electrochemical window and Excellent physical properties such as low flammability, low melting point, low vapor pressure and high ion density. attracted extensive attention and research. Ionic liquids refer to organic salts that are liquid at room temperature and consist of organic cations and organic or inorganic anions. This liquid molten salt is different from other ionic compounds.
随着科学技术的发展，人们的生产生活中不免有许多酸性气体排出。导致了全球气候变暖，以及一系列的环境问题。因此如何有效的处理酸性气体，是一项重要任务。离子液体具有极大的可调性和可做性，可以用于吸收酸性气体。含有羟基功能性的离子液体对二氧化碳，二氧化硫，硫化氢等酸性气体有着显著的吸收能力。With the development of science and technology, many acid gases are inevitably discharged in people's production and life. It has led to global warming and a series of environmental problems. Therefore, how to effectively deal with acid gas is an important task. Ionic liquids have great tunability and manufacturability and can be used to absorb acid gases. Ionic liquids containing hydroxyl functionality have significant absorption capacity for carbon dioxide, sulfur dioxide, hydrogen sulfide and other acid gases.
发明内容SUMMARY OF THE INVENTION
现阶段的离子液体的研究还不是那么完善，对于新型的离子液体也在不断的出现。本发明的含有羟基的功能型的离子液体，具有着操作简单，成本低，纯度高，稳定性强的优点。At present, the research on ionic liquids is not so perfect, and new types of ionic liquids are constantly appearing. The functional ionic liquid containing hydroxyl group of the present invention has the advantages of simple operation, low cost, high purity and strong stability.
为实现上述目的，本发明的技术方案如下：一种羟基功能性离子液体，具有如(Ⅰ)所示的结构式：In order to achieve the above purpose, the technical scheme of the present invention is as follows: a hydroxyl functional ionic liquid having the structural formula shown in (I):
上述的一种羟基功能性离子液体的制备方法，包括如下步骤：The preparation method of above-mentioned a kind of hydroxyl functional ionic liquid, comprises the steps:
1)1-羟基乙基-3-甲基咪唑溴盐的合成：在氮气的保护下，向N-甲基咪唑中缓慢滴加2-溴乙醇和甲苯进行反应，反应完成后用无水乙醚反应洗涤数次，得到固体粗产物1-羟基乙基-3-甲基咪唑溴盐；1) Synthesis of 1-hydroxyethyl-3-methylimidazolium bromide: under the protection of nitrogen, slowly add 2-bromoethanol and toluene dropwise to N-methylimidazole to react, and use anhydrous ether after the reaction is completed. The reaction was washed several times to obtain a solid crude product 1-hydroxyethyl-3-methylimidazolium bromide;
2)1-羟基乙基-3-甲基咪唑溴盐的提纯：用乙酸乙酯和乙腈的混合溶液溶解固体粗产物，重结晶后抽滤，干燥；2) Purification of 1-hydroxyethyl-3-methylimidazolium bromide: the solid crude product was dissolved in a mixed solution of ethyl acetate and acetonitrile, filtered with suction after recrystallization, and dried;
3)氢氧型中间体1-羟基乙基-3-甲基咪唑的合成：向提纯后的1-羟基乙基-3-甲基咪唑溴盐加入去离子水稀释，倒入氢氧型阴离子交换树脂中，反应完成后接取流出液，收集时，不断用AgNO3-HNO3溶液检测，直至检测液出现沉淀或混浊，停止收集；3) Synthesis of hydroxide intermediate 1-hydroxyethyl-3-methylimidazole: add deionized water to the purified 1-hydroxyethyl-3-methylimidazolium bromide to dilute, pour into hydroxide anion In the exchange resin, after the reaction is completed, the effluent is taken, and during collection, the AgNO 3 -HNO 3 solution is continuously used for detection, until the detection liquid appears precipitation or turbidity, and the collection is stopped;
4)将丙酸加入到氢氧型中间体1-羟基乙基-3-甲基咪唑中，室温下进行搅拌反应，旋转蒸发除去水分，真空干燥，得到目标离子液体1-羟基乙基-3-甲基咪唑丙酸。4) adding propionic acid to the hydroxide intermediate 1-hydroxyethyl-3-methylimidazole, carrying out stirring reaction at room temperature, removing moisture by rotary evaporation, and drying in vacuum to obtain the target ionic liquid 1-hydroxyethyl-3 - Methylimidazole propionic acid.
上述的一种羟基功能性离子液体的制备方法，步骤1)中，N-甲基咪唑和2-溴乙醇的摩尔比为1：1.1。In the above-mentioned preparation method of a hydroxyl functional ionic liquid, in step 1), the molar ratio of N-methylimidazole and 2-bromoethanol is 1:1.1.
上述的一种羟基功能性离子液体的制备方法，步骤1)中，反应温度为110℃，反应时间为48h。In the above-mentioned preparation method of a hydroxyl functional ionic liquid, in step 1), the reaction temperature is 110° C. and the reaction time is 48h.
上述的一种羟基功能性离子液体的制备方法，步骤2)中，按体积比，乙酸乙酯：乙腈＝2:1。In the above-mentioned preparation method of a hydroxyl functional ionic liquid, in step 2), by volume ratio, ethyl acetate:acetonitrile=2:1.
上述的一种羟基功能性离子液体的制备方法，步骤2)中，干燥温度为65℃，干燥时间为24h。In the above-mentioned preparation method of a hydroxyl functional ionic liquid, in step 2), the drying temperature is 65° C., and the drying time is 24 h.
上述的一种羟基功能性离子液体的制备方法，步骤3)中，按体积比，提纯后的1-羟基乙基-3-甲基咪唑溴盐：去离子水＝1:1。In the above-mentioned preparation method of a hydroxyl functional ionic liquid, in step 3), by volume ratio, purified 1-hydroxyethyl-3-methylimidazolium bromide: deionized water=1:1.
上述的一种羟基功能性离子液体的制备方法，步骤4)中，按摩尔比，氢氧型中间体1-羟基乙基-3-甲基咪唑：丙酸＝1：1。In the above-mentioned preparation method of a hydroxyl-functional ionic liquid, in step 4), in a molar ratio, the hydroxyl-oxygen intermediate 1-hydroxyethyl-3-methylimidazole:propionic acid=1:1.
上述的一种羟基功能性离子液体的制备方法，步骤4)中，所述的搅拌反应的时间为48h。In the above-mentioned preparation method of a hydroxyl functional ionic liquid, in step 4), the time of the stirring reaction is 48h.
本发明在溴型的功能性离子液体的基础上，合成了羟基类的功能型离子液体。这次的实验拓展了离子液体的种类，并且，所得产品的纯度得到有效的保证，便于对该离子液体的物化性质得到有效的研究，促进了离子液体的发展。Based on the bromine-type functional ionic liquid, the present invention synthesizes a hydroxyl-type functional ionic liquid. This experiment expands the types of ionic liquids, and the purity of the obtained products is effectively guaranteed, which facilitates effective research on the physicochemical properties of the ionic liquids, and promotes the development of ionic liquids.
附图说明Description of drawings
图1是实施例1制备的羟基功能型离子液体的氢谱。1 is the hydrogen spectrum of the hydroxyl-functional ionic liquid prepared in Example 1.
图2是实施例1制备的羟基功能型离子液体的碳谱。2 is the carbon spectrum of the hydroxyl-functional ionic liquid prepared in Example 1.
具体的实施方式specific implementation
下面通过具体的实施例来进一步说明本发明。本发明不限于实施例，在不脱离所述的范围下，可以有微小的变动。The present invention will be further illustrated by specific examples below. The present invention is not limited to the examples, and slight variations are possible without departing from the scope described.
实施例1 一种羟基功能性离子液体Example 1 A hydroxyl functional ionic liquid
制备方法如下：The preparation method is as follows:
1)含有羟基的功能型咪唑类离子液体溴盐的制备：1) Preparation of functional imidazole ionic liquid bromine salt containing hydroxyl:
将适量80ml N-甲基的咪唑加入到三口烧瓶中，氮气保护下，缓慢加入178ml 2-溴乙醇，滴加完毕后，用油浴锅加热搅拌，110℃下回流反应48h。所得产物用10ml乙酸乙酯和5ml乙腈的混合物洗涤三次，重结晶，抽滤。然后将上述液体置于干燥器中，干燥24h，得到1-羟基乙基-3-甲基咪唑溴盐离子液体。N-甲基咪唑与2-溴乙醇的摩尔比为1:1.1。An appropriate amount of 80 ml of N-methyl imidazole was added to the three-necked flask, and 178 ml of 2-bromoethanol was slowly added under nitrogen protection. The product obtained was washed three times with a mixture of 10 ml of ethyl acetate and 5 ml of acetonitrile, recrystallized and filtered with suction. Then, the above liquid was placed in a desiccator and dried for 24 h to obtain 1-hydroxyethyl-3-methylimidazolium bromide ionic liquid. The molar ratio of N-methylimidazole to 2-bromoethanol was 1:1.1.
2)取717行阴离子交换树脂，经过活化再生，处理得到氢氧型阴离子交换树脂。将氢氧型阴离子交换树脂装柱，水洗至中性，放干。将上述的1-羟基乙基-3-甲基咪唑溴盐离子液体倒入树脂中，反应2-4h。反应完成后接取流出液，收集时，不断用AgNO3-HNO3溶液检测，直至检测液出现沉淀或混浊，停止收集。2) Take row 717 of anion exchange resin, activate and regenerate, and process to obtain hydroxide type anion exchange resin. The hydroxide-type anion exchange resin was packed into a column, washed with water until neutral, and allowed to dry. Pour the above-mentioned 1-hydroxyethyl-3-methylimidazolium bromide ionic liquid into the resin and react for 2-4h. After the reaction was completed, the effluent was taken, and during collection, the AgNO 3 -HNO 3 solution was continuously used for detection, until the detection solution appeared precipitation or turbidity, and the collection was stopped.
3)将上述的60ml氢氧型离子液体和50ml丙酸混合，室温下反应48h，旋转蒸发除去水分，55℃真空干燥3天，得到1-羟基乙基-3-甲基咪唑丙酸盐子液体，产率为85.6％，纯度为98％。1-羟基乙基-3-甲基咪唑溴盐与丙酸的摩尔比为1:1。3) Mix the above-mentioned 60ml of hydroxide ionic liquid and 50ml of propionic acid, react at room temperature for 48h, remove water by rotary evaporation, and vacuum dry at 55°C for 3 days to obtain 1-hydroxyethyl-3-methylimidazole propionate. Liquid, 85.6% yield, 98% purity. The molar ratio of 1-hydroxyethyl-3-methylimidazolium bromide to propionic acid was 1:1.
图1为所制备离子液体的核磁氢谱，各个氢的特征峰与所对应的离子液体的官能团上氢的位置如图1所示，图1氢的特征峰符合1-羟基乙基-3甲基咪唑丙酸盐离子液体所含氢的位置。图2为所制备离子液体的核磁碳谱，各个碳的特征峰与所对应的离子液体碳的位置如图2所示，图2碳的特征峰符合1-羟基乙基-3甲基咪唑丙酸盐离子液体各基团碳的位置。Figure 1 is the hydrogen NMR spectrum of the prepared ionic liquid. The characteristic peaks of each hydrogen and the positions of hydrogen on the functional groups of the corresponding ionic liquids are shown in Figure 1. The characteristic peaks of hydrogen in Figure 1 are consistent with 1-hydroxyethyl-3 methyl The position of the hydrogen contained in the imidazolium propionate ionic liquid. Fig. 2 is the carbon nuclear magnetic spectrum of the prepared ionic liquid, the characteristic peak of each carbon and the position of the corresponding ionic liquid carbon are shown in Fig. 2, the characteristic peak of the carbon in Fig. 2 is consistent with 1-hydroxyethyl-3 methylimidazopropane The position of each group carbon in the acid salt ionic liquid.
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| CN202210013382.6A Pending CN114349706A (en) | 2022-01-06 | 2022-01-06 | A kind of hydroxyl functional ionic liquid and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115536588A (en) * | 2022-11-10 | 2022-12-30 | 辽宁大学 | A kind of hydroxyglycine functional ionic liquid, its preparation method and its application in extracting iodine |
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| CN107353252A (en) * | 2017-08-03 | 2017-11-17 | 辽宁大学 | A kind of ionic liquid with carboxylic acid and its preparation method and application |
| CN107602475A (en) * | 2017-10-31 | 2018-01-19 | 辽宁大学 | Propyl imidazole taurine ionic liquid of 1 methyl 3 and its preparation method and application |
| CN110330459A (en) * | 2019-07-18 | 2019-10-15 | 中国科学院过程工程研究所 | A kind of carboxylate ion liquid and the preparation method and application thereof |
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| CN107353252A (en) * | 2017-08-03 | 2017-11-17 | 辽宁大学 | A kind of ionic liquid with carboxylic acid and its preparation method and application |
| CN107602475A (en) * | 2017-10-31 | 2018-01-19 | 辽宁大学 | Propyl imidazole taurine ionic liquid of 1 methyl 3 and its preparation method and application |
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| CN115536588A (en) * | 2022-11-10 | 2022-12-30 | 辽宁大学 | A kind of hydroxyglycine functional ionic liquid, its preparation method and its application in extracting iodine |
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