CN102020610A - Low-viscosity ionic liquid - Google Patents
Low-viscosity ionic liquid Download PDFInfo
- Publication number
- CN102020610A CN102020610A CN2009100924850A CN200910092485A CN102020610A CN 102020610 A CN102020610 A CN 102020610A CN 2009100924850 A CN2009100924850 A CN 2009100924850A CN 200910092485 A CN200910092485 A CN 200910092485A CN 102020610 A CN102020610 A CN 102020610A
- Authority
- CN
- China
- Prior art keywords
- liquid
- ionic liquid
- chloride
- iron
- viscosity
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 67
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 7
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 22
- 239000007788 liquid Substances 0.000 claims description 16
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
- 229910052742 iron Inorganic materials 0.000 claims description 12
- 239000002994 raw material Substances 0.000 claims description 12
- -1 glyoxaline compound Chemical class 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 238000010907 mechanical stirring Methods 0.000 claims description 4
- KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical compound C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 claims description 3
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 claims description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 3
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 3
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- IYVYLVCVXXCYRI-UHFFFAOYSA-N 1-propylimidazole Chemical compound CCCN1C=CN=C1 IYVYLVCVXXCYRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims 4
- 238000005660 chlorination reaction Methods 0.000 claims 3
- 238000001035 drying Methods 0.000 claims 2
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 230000001012 protector Effects 0.000 claims 1
- 230000003647 oxidation Effects 0.000 abstract description 6
- 238000007254 oxidation reaction Methods 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 5
- 238000009776 industrial production Methods 0.000 abstract description 4
- 238000011160 research Methods 0.000 abstract description 3
- 239000002250 absorbent Substances 0.000 abstract description 2
- 230000002745 absorbent Effects 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 150000001805 chlorine compounds Chemical class 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000002892 organic cations Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OGMMPDKNASYKQC-UHFFFAOYSA-N 1,3-dibutyl-1,2-dihydroimidazol-1-ium;chloride Chemical compound [Cl-].CCCCN1C[NH+](CCCC)C=C1 OGMMPDKNASYKQC-UHFFFAOYSA-N 0.000 description 2
- IAZSXUOKBPGUMV-UHFFFAOYSA-N 1-butyl-3-methyl-1,2-dihydroimidazol-1-ium;chloride Chemical compound [Cl-].CCCC[NH+]1CN(C)C=C1 IAZSXUOKBPGUMV-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- HVUKATMIYDUATC-UHFFFAOYSA-N 3-benzyl-1-dodecyl-1,2-dihydroimidazol-1-ium;chloride Chemical compound [Cl-].C1=C[NH+](CCCCCCCCCCCC)CN1CC1=CC=CC=C1 HVUKATMIYDUATC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002891 organic anions Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000033116 oxidation-reduction process Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- VITRLXDSBBVNCZ-UHFFFAOYSA-K trichloroiron;hydrate Chemical compound O.Cl[Fe](Cl)Cl VITRLXDSBBVNCZ-UHFFFAOYSA-K 0.000 description 2
- 239000002912 waste gas Substances 0.000 description 2
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- AWUXTOKKDIWYEK-UHFFFAOYSA-N dodecane;hydrochloride Chemical compound Cl.CCCCCCCCCCCC AWUXTOKKDIWYEK-UHFFFAOYSA-N 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 229910021432 inorganic complex Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical class CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及一种低黏度离子液体的制备方法。此离子液体为摩尔比大于1∶1的氯化烷基咪唑化合物与氯化铁在开放环境中直接混合反应得到的油相产物。该离子液体不仅黏度低且疏水性强,表现出较高的热稳性高和氧化能力。该离子液体作为溶剂、催化剂或吸收剂可以广泛应用于科研及工业生产中。The invention relates to a preparation method of a low-viscosity ionic liquid. The ionic liquid is an oil phase product obtained by directly mixing and reacting alkylimidazole chloride compound and ferric chloride with a molar ratio greater than 1:1 in an open environment. The ionic liquid not only has low viscosity and strong hydrophobicity, but also exhibits high thermal stability and oxidation ability. The ionic liquid can be widely used in scientific research and industrial production as a solvent, catalyst or absorbent.
Description
技术领域technical field
本发明涉及低黏度离子液体的制备方法,特别涉及一种黏度低和疏水性强的铁基离子液体的制备,该离子液体所表现出的高热稳定性和强氧化性,可作为溶剂、催化剂、吸收剂广泛应用于科研与工业生产中。The invention relates to a preparation method of a low-viscosity ionic liquid, in particular to a preparation of an iron-based ionic liquid with low viscosity and strong hydrophobicity. The high thermal stability and strong oxidative properties of the ionic liquid can be used as solvents, catalysts, Absorbents are widely used in scientific research and industrial production.
技术背景technical background
离子液体是在室温及相邻温度下呈液态的物质,由不对称的有机阳离子和有机或无机阴离子组成,离子液体由此可以分为两大类,一类是由有机阳离子和有机阴离子组成的纯有机离子液体,另一类是由有机阳离子与无机络合阴离子组成的金属基离子液体。离子液体的合成均是通过离子交换来实现的。离子液体的这种结构和合成特点使得离子液体称为“结构可设计”的化合物,离子液体的种类难以计数。Ionic liquids are substances that are liquid at room temperature and adjacent temperatures, and are composed of asymmetric organic cations and organic or inorganic anions. Ionic liquids can be divided into two categories, one is composed of organic cations and organic anions Pure organic ionic liquids, and another type of metal-based ionic liquids composed of organic cations and inorganic complex anions. The synthesis of ionic liquids is achieved by ion exchange. The structure and synthesis characteristics of ionic liquids make ionic liquids called "structurally designable" compounds, and the types of ionic liquids are difficult to count.
不仅如此,研究表明离子液体具有溶解能力强,挥发性低,热稳定性高的优点,因此离子液体又被称为“绿色溶剂”。离子液体不仅应用于电化学中的电解质,而且在有机合成中作为环境友好溶剂以及多相催化中的固定相等方面,均有大量的研究报道,离子液体的潜在工业应用前景也备受关注。Not only that, studies have shown that ionic liquids have the advantages of strong solvency, low volatility, and high thermal stability, so ionic liquids are also called "green solvents". Ionic liquids are not only used as electrolytes in electrochemistry, but also as environmentally friendly solvents in organic synthesis and immobilized phases in heterogeneous catalysis. There are a lot of research reports on the potential industrial application of ionic liquids.
但是至今,离子液体在工业中的应用未见有大规模的报道,其中主要因为:(1)现有的离子液体价格昂贵;(2)离子液体的黏度大,不利于工业操作;(3)离子液体水溶性较大,流失较为严重,不利于循环再利用。因此,发展绿色的离子液体合成方法,开发低廉的离子液体,尤其是低黏度离子液体的合成,才能满足离子液体在工业生产中的要求,最终实现大规模应用。But so far, the application of ionic liquids in industry has not seen large-scale reports, mainly because: (1) the existing ionic liquids are expensive; (2) the viscosity of ionic liquids is large, which is not conducive to industrial operations; (3) Ionic liquids have high water solubility and serious loss, which is not conducive to recycling. Therefore, the development of green ionic liquid synthesis methods and the development of low-cost ionic liquids, especially the synthesis of low-viscosity ionic liquids, can meet the requirements of ionic liquids in industrial production and finally achieve large-scale applications.
铁基离子液体是金属基离子液体中研究最为广泛的离子液体之一,主要应用有机合成的催化体系。起初,大多的铁基离子液体是将氯化烷基咪唑化合物与无水三氯化铁在密封干燥的惰性气氛环境中进行反应,以避免空气中的水分干扰。自2004年日本科学家首次报道在开放环境中采用水合氯化铁混合反应直接合成可以与水自动分相的铁基离子液体。这是一种可以采用廉价原料并在开放环境的简易合成离子液体的方法。由此可以通过优化原料的配比,获得组分不同,物化特性各异的离子液体,尤其降低离子液体的黏度,使得这种集有机离子液体的超溶解特性、强疏水性和高的热稳定性离子液体和过渡金属离子的氧化性能于一体的离子液体能够满足工业生产的要求,发展其在工业有机溶媒的分离回收和还原性废气的净化方面广泛应用。Iron-based ionic liquids are one of the most widely studied ionic liquids among metal-based ionic liquids, and are mainly used in catalytic systems for organic synthesis. Initially, most iron-based ionic liquids react alkylimidazole chloride compounds with anhydrous ferric chloride in a sealed and dry inert atmosphere to avoid interference from moisture in the air. Since 2004, Japanese scientists reported for the first time that an iron-based ionic liquid that can automatically phase-separate with water was directly synthesized by using ferric chloride hydrate mixed reaction in an open environment. This is a facile method for synthesizing ionic liquids using cheap raw materials and in an open environment. Therefore, by optimizing the ratio of raw materials, ionic liquids with different components and different physical and chemical properties can be obtained, especially the viscosity of ionic liquids can be reduced, so that this kind of organic ionic liquid has super solubility, strong hydrophobicity and high thermal stability. The ionic liquid that integrates the oxidation properties of the active ionic liquid and the transition metal ion can meet the requirements of industrial production, and it is widely used in the separation and recovery of industrial organic solvents and the purification of reducing waste gas.
发明内容Contents of the invention
本发明的目的是针对功能化离子液体合成过程中为了实现离子液体的特殊功能而必需选择具有特定结构的原料及设定复杂的合成工艺的技术难题,提供一种低黏度的离子液体的简单易行的合成方法。这种离子液体是由有机阳离子与络合铁阴离子组合而成,通过调控络合铁阴离子含量可以获得黏度很低的离子液体,为实现离子液体在工业应用奠定基础。此离子液体同时将有机离子液体的超溶解能力、疏水性强和热稳定性高,以及过渡金属基离子液体的氧化性能集于一体,在分离回收工业有机溶媒及净化还原性废气方面有广泛的应用前景。The purpose of the present invention is to provide a low-viscosity ionic liquid that is simple and easy to use in order to realize the special function of the ionic liquid in the synthesis process of the functionalized ionic liquid. Row synthesis method. This ionic liquid is composed of organic cations and complex iron anions. By adjusting the content of complex iron anions, an ionic liquid with very low viscosity can be obtained, which lays the foundation for the industrial application of ionic liquids. This ionic liquid combines the supersolvability, strong hydrophobicity and high thermal stability of organic ionic liquids, and the oxidation performance of transition metal-based ionic liquids. It has a wide range of applications in the separation and recovery of industrial organic solvents and the purification of reducing waste gases. Application prospects.
本发明的目的是通过如下的技术方案实现的:The purpose of the present invention is achieved through the following technical solutions:
低黏度离子液体的制备包括以下步骤:The preparation of low viscosity ionic liquid comprises the following steps:
1)以咪唑类化合物为原料,与氯烷烃物质直接混合(无需助溶剂)于带有回流冷凝管的反应装置.水浴加热到60~90℃,恒温反应30~90小时,用乙酸乙酯多次洗涤,再减压蒸馏得氯化烷基咪唑离子液体产物。1) Use imidazole compounds as raw materials, mix directly with chloroalkane substances (no co-solvent required) in a reaction device with a reflux condenser. Heat in a water bath to 60-90°C, and react at a constant temperature for 30-90 hours. washing, and then distilled under reduced pressure to obtain the alkylimidazolium chloride ionic liquid product.
2)将上述方法合成的氯化烷基咪唑离子液体与氯化铁以一定摩尔比混合,在室温下的开放环境中长时间搅拌,离心分层得低黏度离子液体。2) Mix the alkylimidazolium chloride ionic liquid synthesized by the above method with ferric chloride in a certain molar ratio, stir for a long time in an open environment at room temperature, and centrifuge and layer to obtain a low-viscosity ionic liquid.
上述方法反应式如下:Above-mentioned method reaction formula is as follows:
所述咪唑原料的结构式为:The structural formula of the imidazole raw material is:
其中R代表碳原子数为1~4的烷基取代基,R1代表碳原子数为3~16的烷基取代基(包括苄基取代基和萘基取代基等)Where R represents an alkyl substituent with 1 to 4 carbon atoms, and R1 represents an alkyl substituent with 3 to 16 carbon atoms (including benzyl substituents and naphthyl substituents, etc.)
所述的咪唑类化合物是可以是N-甲基咪唑,也可以是N-丁基咪唑、N-丙基咪唑、N-苄基咪唑等The imidazole compound can be N-methylimidazole, N-butylimidazole, N-propylimidazole, N-benzylimidazole, etc.
所述的氯代烷烃可以是氯代正丁烷,也可以是氯代正辛烷等的3~16个碳的氯代烷烃等。The chlorinated alkanes may be chlorinated n-butane, or chlorinated alkanes with 3-16 carbons such as chlorinated n-octane, etc.
所述的氯化铁可以是含六个结晶水的水合氯化铁,也可以是无水氯化铁。The ferric chloride can be ferric chloride hydrate containing six crystal waters, or anhydrous ferric chloride.
所述的开放环境是指没有除水密封干燥的保护装置和惰性气氛保护的常压条件下的自然环境。The open environment refers to a natural environment under normal pressure without a water-removing, sealed and dry protective device and an inert atmosphere.
本发明所述的离子液体黏度在室温条件下用旋转粘度计测定。The viscosity of the ionic liquid of the present invention is measured with a rotational viscometer at room temperature.
本发明所述的离子液体的氧化还原电位采用氧化还原电极直接测定。The oxidation-reduction potential of the ionic liquid described in the present invention is directly measured by an oxidation-reduction electrode.
本发明所述的离子液体的热稳定性测量过程如下:将盛放样品坩埚放置在马弗炉中,在空气气氛中100℃为始点每10℃设置一样品加热1小时,样品开始固化为临界点,即为离子液体的热稳定性。The thermal stability measurement process of the ionic liquid of the present invention is as follows: the crucible containing the sample is placed in a muffle furnace, and a sample is set at 100° C. in an air atmosphere and heated for 1 hour every 10° C., and the sample begins to solidify to a critical temperature. The point is the thermal stability of the ionic liquid.
本发明所述的离子液体疏水性能是在离子液体与水组成的液液两相体系中,采用卡尔费休法测定离子液体中的水份含量。The hydrophobic property of the ionic liquid in the present invention is that in the liquid-liquid two-phase system composed of the ionic liquid and water, the water content in the ionic liquid is measured by the Karl Fischer method.
下面通过具体的实施例对本发明的技术方案作进一步的介绍,但本发明不限于此实例。The technical solution of the present invention will be further introduced through specific examples below, but the present invention is not limited to this example.
实施例1Example 1
在带有冷凝回流装置的250ml三口烧瓶中放入N-丁基咪唑(65g,0.52mol)和氯丁烷(58.14g,0.62mol),反应混合物在78℃机械搅拌反应72个小时,反应混合物冷却后用乙酸乙酯洗涤3~5次,去除未反应完全的原料,再减压蒸馏得淡黄色粘稠液体,1-丁基-3-丁基氯化咪唑110g,产率90%。Put N-butylimidazole (65g, 0.52mol) and chlorobutane (58.14g, 0.62mol) in the 250ml there-necked flask that has condensing reflux device, reaction mixture was reacted 72 hours at 78 ℃ of mechanical stirring, reaction mixture After cooling, it was washed with ethyl acetate for 3 to 5 times to remove unreacted raw materials, and then distilled under reduced pressure to obtain a light yellow viscous liquid, 110 g of 1-butyl-3-butyl imidazole chloride, with a yield of 90%.
把产物1-丁基-3-丁基氯化咪唑分成四份,以物质量比(1∶1,1∶2,1∶3,1∶4)加入FeCl3·6H2O,常温下搅拌24h,离心静止分层,1∶1的取下层液体,1∶2,1∶3,1∶4的分别取上层液体。Divide the product 1-butyl-3-butylimidazole chloride into four parts, add FeCl 3 6H 2 O at a mass ratio (1:1, 1:2, 1:3, 1:4), and stir at room temperature After 24 hours, centrifuge to separate layers, take the lower layer liquid for 1:1, and take the upper layer liquid for 1:2, 1:3, and 1:4 respectively.
以下是四种铁基离子液体的物理数据和检测数据。The following are the physical data and detection data of four iron-based ionic liquids.
实施例2Example 2
在带有冷凝回流装置的250ml三口烧瓶中放入N-苄基咪唑(80g,0.5mol)和氯代十二烷(113.7g,0.556mol),反应混合物在85℃机械搅拌反应72个小时,反应混合物冷却后加乙酸乙酯,加热到85℃回流一段时间,再冷却到室温分离出乙酸乙酯,重复以上操作3~5次,去除未反应完全的原料,再减压加热到85℃蒸馏,得黄褐色固体1-苄基-3-十二烷基氯化咪唑182g,产率94%。Put N-benzyl imidazole (80g, 0.5mol) and dodecane chloride (113.7g, 0.556mol) in the 250ml there-necked flask with condensing reflux device, the reaction mixture reacted 72 hours at 85 ℃ of mechanical stirring, After the reaction mixture is cooled, add ethyl acetate, heat to 85°C and reflux for a period of time, then cool to room temperature to separate ethyl acetate, repeat the above operation 3 to 5 times, remove unreacted raw materials, and then heat to 85°C under reduced pressure for distillation 182 g of tan solid 1-benzyl-3-dodecyl imidazole chloride was obtained with a yield of 94%.
把1-苄基-3-十二烷基氯化咪唑分成四份,以物质量比(1∶1,1∶2,1∶3,1∶4)加入FeCl3·6H2O,水浴加热到45℃搅拌24h,离心静止分层,1∶1的取下层液体,1∶2,1∶3,1∶4的分别取上层液体。Divide 1-benzyl-3-dodecyl imidazole chloride into four parts, add FeCl 3 6H 2 O at a mass ratio (1:1, 1:2, 1:3, 1:4), heat in a water bath Stir at 45°C for 24 hours, centrifuge statically to separate layers, take the lower layer liquid for 1:1, and take the upper layer liquid for 1:2, 1:3, and 1:4 respectively.
以下是四种铁基离子液体的物理数据和检测数据The following are the physical data and test data of four iron-based ionic liquids
实施例3Example 3
在带有冷凝回流装置的250ml三口烧瓶中放入433.3gN-甲基咪唑和氯丁烷512.9g,反应混合物在78℃机械搅拌反应72个小时,反应混合物冷却后用乙酸乙酯洗涤3~5次,去除未反应完全的原料,再减压蒸馏得淡黄色粘稠液体,即1-甲基-3-丁基氯化咪唑852.9g,产率90.13%。Put 433.3g of N-methylimidazole and 512.9g of chlorobutane into a 250ml three-neck flask with a condensing reflux device, and the reaction mixture was mechanically stirred at 78°C for 72 hours. After the reaction mixture was cooled, it was washed with ethyl acetate for 3 to 5 Once, the unreacted raw materials were removed, and then distilled under reduced pressure to obtain a light yellow viscous liquid, namely 852.9 g of 1-methyl-3-butyl imidazole chloride, with a yield of 90.13%.
把产物1-甲基-3-丁基氯化咪唑分成四份,以物质量比(1∶1,1∶1.5,1∶2,1∶2.5)加入FeCl3·6H2O,常温下搅拌24h,离心静止分层,1∶1和1∶1.5的取下层液体,,1∶2和1∶2.5的分别取上层液体。Divide the product 1-methyl-3-butylimidazole chloride into four parts, add FeCl 3 6H 2 O at a mass ratio (1:1, 1:1.5, 1:2, 1:2.5), and stir at room temperature After 24 hours, centrifuge statically to separate layers, take the lower layer liquid for 1:1 and 1:1.5, and take the upper layer liquid for 1:2 and 1:2.5 respectively.
四种离子液体的物理数据和检测数据如下:The physical data and detection data of the four ionic liquids are as follows:
四种离子液体的溶解能力:体积比为1/20离子液体在相应溶剂中的溶解情况如下:Solubility of four kinds of ionic liquids: the volume ratio of 1/20 ionic liquids dissolves in corresponding solvents as follows:
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009100924850A CN102020610A (en) | 2009-09-16 | 2009-09-16 | Low-viscosity ionic liquid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009100924850A CN102020610A (en) | 2009-09-16 | 2009-09-16 | Low-viscosity ionic liquid |
Publications (1)
Publication Number | Publication Date |
---|---|
CN102020610A true CN102020610A (en) | 2011-04-20 |
Family
ID=43862430
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2009100924850A Pending CN102020610A (en) | 2009-09-16 | 2009-09-16 | Low-viscosity ionic liquid |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN102020610A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102911120A (en) * | 2012-10-22 | 2013-02-06 | 北京化工大学 | Method for synthesizing iron-base ionic liquid through water-phase cyclic utilization |
CN102993101A (en) * | 2012-11-29 | 2013-03-27 | 南京工业大学 | Imidazole ionic liquid and application thereof |
CN103254031A (en) * | 2012-02-17 | 2013-08-21 | 北京化工大学 | Method for separating alcohol-water system by extracting through using hydrophobic Fe-based ionic liquid |
CN105198815A (en) * | 2015-08-24 | 2015-12-30 | 四川大学 | Iron-based imidazole ionic liquid for removing SO2 in flue gas and preparation method thereof |
CN106064053A (en) * | 2016-06-03 | 2016-11-02 | 华中科技大学 | A kind of flue gas demercuration adsorbent and preparation method thereof |
CN116656331A (en) * | 2023-05-30 | 2023-08-29 | 西南石油大学 | Corrosion agent and method for enhancing adsorption gas desorption of corrosion modified shale gas layer |
-
2009
- 2009-09-16 CN CN2009100924850A patent/CN102020610A/en active Pending
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103254031A (en) * | 2012-02-17 | 2013-08-21 | 北京化工大学 | Method for separating alcohol-water system by extracting through using hydrophobic Fe-based ionic liquid |
CN103254031B (en) * | 2012-02-17 | 2014-12-10 | 北京化工大学 | Method for separating alcohol-water system by extracting through using hydrophobic Fe-based ionic liquid |
CN102911120A (en) * | 2012-10-22 | 2013-02-06 | 北京化工大学 | Method for synthesizing iron-base ionic liquid through water-phase cyclic utilization |
CN102993101A (en) * | 2012-11-29 | 2013-03-27 | 南京工业大学 | Imidazole ionic liquid and application thereof |
CN102993101B (en) * | 2012-11-29 | 2015-02-18 | 南京工业大学 | Imidazole ionic liquid and application thereof |
CN105198815A (en) * | 2015-08-24 | 2015-12-30 | 四川大学 | Iron-based imidazole ionic liquid for removing SO2 in flue gas and preparation method thereof |
CN106064053A (en) * | 2016-06-03 | 2016-11-02 | 华中科技大学 | A kind of flue gas demercuration adsorbent and preparation method thereof |
CN116656331A (en) * | 2023-05-30 | 2023-08-29 | 西南石油大学 | Corrosion agent and method for enhancing adsorption gas desorption of corrosion modified shale gas layer |
CN116656331B (en) * | 2023-05-30 | 2024-11-22 | 西南石油大学 | A dissolving agent and method for dissolving and transforming shale gas layers to enhance desorption of adsorbed gas |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101386597B (en) | Alkyl imidazoles perrhenate ion liquid and preparation method thereof | |
CN102020610A (en) | Low-viscosity ionic liquid | |
CN107382803A (en) | A kind of preparation method of β hydroxy phenyls selenide compound | |
CN101787042A (en) | Copper-nitrogen compound and application thereof | |
McNeice et al. | Quinine based ionic liquids: A tonic for base instability | |
CN104610178B (en) | A kind of preparation method of the double fluorine benzheterocycle conjugative monomers of iodine atom substitution | |
JP2009269917A (en) | Method for producing tetrafluoroboric acid quaternary ammonium salt | |
CN114349674B (en) | Thiourea compound and preparation method thereof | |
Liu et al. | DBU-based dicationic ionic liquids promoted esterification reaction of carboxylic acid with primary chloroalkane under mild conditions | |
Zhang et al. | Preparation and characterization of novel ionic liquid based on benzotriazolium cation | |
CN114349706A (en) | A kind of hydroxyl functional ionic liquid and preparation method thereof | |
US10844081B2 (en) | Protected organoboronic acids with tunable reactivity, and methods of use thereof | |
CN100532359C (en) | Synthetic method of room temperature ionic liquid | |
CN107311896A (en) | A kind of method of utilization sulfur dioxide synthesizing aryl sulfinic acid | |
CN102993114A (en) | Method for producing 1H-tetrazole-5-acetic acid | |
CN106632437A (en) | Lithium oxalyldifluroborate and lithium tetrafluoroborate separating method | |
CN105439969B (en) | A kind of method for preparing the triazole of 3,5 dioxo 1,2,4 | |
CN106674261A (en) | Lithium oxalyldifluoroborate purification method | |
CN101143848B (en) | A kind of imidazole ion salt with push-pull electronic structure, preparation method and use thereof | |
CN108047114B (en) | Halogenated trifluoromethylpyrrole derivatives and preparation method and application thereof | |
CN107382895B (en) | A kind of synthetic method of 2-phenylbenzoxazole compound | |
CN114733570B (en) | A kind of solid catalyst based on sodium carboxymethyl cellulose, preparation method and application thereof | |
CN105175297A (en) | Synthesis and application of 4-formyl benzoic acid adamantine ester condensed o-aminobenzene thiophenol schiff base nickel complex | |
CN103980077B (en) | A kind of synthetic polyfluoro of suzuki reaction of catalysis of ligand-free palladium is for the method for para-terpheny derivative | |
CN105669517B (en) | A kind of process for catalytic synthesis of Benzazole compounds |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20110420 |