CN102924382A - Disalicylide-functional imidazole Gemini ionic liquid and preparation method thereof - Google Patents
Disalicylide-functional imidazole Gemini ionic liquid and preparation method thereof Download PDFInfo
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Abstract
The invention provides a disalicylide-functional imidazole Gemini ionic liquid and a preparation method thereof. A molecular structure of the disalicylide-functional imidazole Gemini ionic liquid contains functional groups of aldehyde groups, hydroxyl groups and aryl nucleuses. The disalicylide-functional imidazole Gemini ionic liquid can undergo complex reactions and condensation reactions with metal ions, formaldehyde, active methylene compounds, primary amine and hydrazine to produce a small-molecular weight complex ionic liquid and a high-molecular weight complex ionic liquid, or can be used as a monomer for preparation of a polymer ionic liquid.
Description
Technical field
The present invention relates to ionic liquid, particularly a kind of imidazole type gemini ionic liquid of double salicylaldehyde functionalization, the monomer as coordination functionalized ion liquid, preparation coordination functionalized ion liquid polymkeric substance belongs to field of functional materials.
Technical background
Through the development of two more than ten years, the Application Areas of ionic liquid develops the emerging fields such as nano material, clean energy, photoelectric material, bioprobe rapidly also from initial electrochemistry, organic synthesis and catalytic chemistry.Positively charged ion or negatively charged ion that functionalized ion liquid refers to form in the ionic liquid contain specific functional group.Functionalized ion liquid except the properties with ionic liquid self, the more special performance that also has functional group to bring.Development along with functionalized ion liquid, createed the ionic liquid of many unique properties, so that ionic liquid has unprecedented diversified character, various performances are more and more wide in range, the utilization scope is more and more wider, so ionic liquid is called as " planner's solvent ", this design comprises for the functionalization of its physical properties (for example: flowability, density, specific conductivity, liquid scope) with for the functionalization of chemical property (polarity, acidity, chirality, coordination ability, solvability).
Ionic liquid with coordination function is a kind of of functionalized ion liquid, the coordination of traditional NOT-function ionic liquid is very weak, the ionic liquid that design has the coordination function, dentate and central metal ion coordination reaction by wherein fix metal ion, make it the dual function that realization response medium and catalyzer solidify in catalyzed reaction, reduce the loss of metal ion catalyst, this is to using the catalyzed reaction of expensive transition-metal catalyst or expensive ligands, and is significant.Based on above-mentioned consideration, the inventor has designed a kind of imidazole type gemini ionic liquid of double salicylaldehyde functionalization.The step that realization the invention is intended to is to use the two ends of straight-chain paraffin or poly-ethoxy ether chain to connect respectively the 1-imidazolyl, straight-chain paraffin or polyethers that end group is connected with two imidazole rings have been formed, No. 3 positions of two imidazole rings N atom at described straight-chain paraffin or polyethers two ends carries out quaternary ammonium salinization reaction with the 5-chloromethyl salicylaldehyde respectively, make the imidazole type gemini quaternary ammonium salt of double salicylaldehyde functionalization, make afterwards the imidazole type gemini ionic liquid of double salicylaldehyde functionalization by anionresin.
The imidazole type gemini ionic liquid of double salicylaldehyde functionalization of the present invention, can be directly and metal ion carry out the chelating coordination, form the imidazole type gemini ionic liquid of support salicylic aldehyde title complex, be used for catalyst for oxidation reaction, the polymerisation catalysts of profit two-phase; Described double salicylaldehyde functionalization imidazole type gemini ionic liquid contains aldehyde radical, have the number of chemical response characteristic: such as can with azanol reaction, make the imidazole type gemini ionic liquid of double salicylaldehyde oxime grafting, as the extraction agent of catalyst for oxidation reaction, polymerisation catalysts or metal ion in the profit two-phase.
Summary of the invention
The invention provides a kind of imidazole type gemini ionic liquid of double salicylaldehyde functionalization, have structure shown in the general formula (I):
Q is selected from its formula of (I):
C
1～C
20Saturated or unsaturated alkyl,
Or
In a kind of, described n is selected from a kind of in 1～500 positive integer; X is selected from F, Cl, Br, NO
3, HSO
4, CH
3COO, C
3F
7COO, BF
4, PF
6, SbF
6, CF
3SO
3, C
4F
9SO
3, (CF
3SO
2)
3C, (CF
3SO
2)
2A kind of among the N.
The imidazole type gemini ionic liquid of the double salicylaldehyde functionalization of structure is realized according to following synthetic route shown in the general formula provided by the invention (I):
In described synthetic route, Q is selected from:
C
1～C
20Saturated or unsaturated alkyl,
Or
In a kind of, described n is selected from a kind of in 1～500 positive integer; M among the MX is selected from K or Na, and X is selected from F, Cl, Br, NO
3, HSO
4, CH
3COO, C
3F
7COO, BF
4, PF
6, SbF
6, CF
3SO
3, C
4F
9SO
3, (CF
3SO
2)
3C, (CF
3SO
2)
2A kind of among the N.
Concrete preparation process is as follows:
Step 1 takes by weighing general formula (II) and is dissolved in the organic solvent in reactor, makes solution (1), takes by weighing the 5-chloromethyl salicylaldehyde again and is dissolved in the organic solvent, makes solution (2).Control the temperature of described solution (2) between 5～25 ℃, under stirring described solution (1) is added in the described solution (2), react after 2～6 hours, temperature is brought up to 60～85 ℃, and restir reaction 4～12 hours is down to 5～10 ℃ with the reaction product system temperature, filter, filter cake with an organic solvent washs 3～5 times, after the drying, makes general formula (III) Shuangzi imidazole type quaternary ammonium salt.
Wherein said general formula (II) is 1: 2.0～2.5 with the mol ratio of 5-chloromethyl salicylaldehyde, described organic solvent refers to tetrahydrofuran (THF), 1,4-dioxane, glycol dimethyl ether, ethylene glycol diethyl ether, ethyl acetate, acetonitrile, acetone or methylethylketone, the consumption of described organic solvent are general formula (II) and 5-chloromethyl salicylaldehyde quality summation 2～6 times;
The Shuangzi imidazole type quaternary ammonium salt that step 2 takes by weighing structure shown in the synthetic route formula of (III) is dissolved in the Fatty Alcohol(C12-C14 and C12-C18), make solution (3), taking by weighing MX is dissolved in the Fatty Alcohol(C12-C14 and C12-C18) again, make solution (4), the temperature of control solution (4) is between 25～85 ℃, stir lower in solution (3) the adding solution (4), behind the stirring reaction 2～6 hours, the reaction product system temperature is down to-10～10 ℃, filtration makes filter cake, with an organic solvent dissolves described filter cake, the elimination insolubles, revolve steaming filtrate and eliminate organic solvent, make the imidazole type gemini ionic liquid of the double salicylaldehyde functionalization of structure shown in the general formula (I);
Wherein said Fatty Alcohol(C12-C14 and C12-C18) refers to a kind of in methyl alcohol, ethanol, propyl alcohol or the butanols; The consumption of described Fatty Alcohol(C12-C14 and C12-C18) is general formula (III) Shuangzi imidazole type quaternary ammonium salt and MX quality summation 2～6 times; M among the MX is selected from K or Na, and X is selected from F, Cl, Br, NO
3, HSO
4, CH
3COO, C
3F
7COO, BF
4, PF
6, SbF
6, CF
3SO
3, C
4F
9SO
3, (CF
3SO
2)
3C, (CF
3SO
2)
2A kind of among the N, the consumption of MX is 2.0～2.5 times of general formula (III) gemini quaternary ammonium salt molar weight; Described organic solvent is selected from tetrahydrofuran (THF), 1,4-dioxane, glycol dimethyl ether, ethylene glycol diethyl ether, ethyl acetate, chloroform, acetonitrile or methyl-sulphoxide, the consumption of described organic solvent are general formula (III) Shuangzi imidazole type quaternary ammonium salt and MX quality summation 2～6 times.
The raw materials of the imidazole type gemini ionic liquid of the double salicylaldehyde functionalization of structure shown in the general formula provided by the invention (I): general formula (II) compound can be with reference to the intelligent treasure of duty " having the polyethylene glycol type gemini ionic liquid of temperature control two-phase character and the application in organic synthesis thereof ", Institutes Of Technology Of Nanjing, the method for Ph D dissertation report makes; The 5-chloromethyl salicylaldehyde can make with reference to the disclosed method of CN201110063599X, and all the other all derive from existing chemical goods.
The imidazole type gemini ionic liquid of the double salicylaldehyde functionalization shown in the general formula provided by the invention (I) has following characteristics:
1. the method for preparing the imidazole type gemini ionic liquid of described double salicylaldehyde functionalization all is classical organic synthesis technology, and preparation manipulation is simple and easy to do, and the three wastes are few, and product yield and purity are high.
2. by the Q unit in the imidazole type gemini ionic liquid of adjusting described double salicylaldehyde functionalization, can change hydrophilicity and oleophylic performance, fusing point height and the solubleness in polarity and non-polar solvent or ionic liquid of the imidazole type gemini ionic liquid of described double salicylaldehyde functionalization.
3. the imidazole type gemini ionic liquid of described double salicylaldehyde functionalization contains aldehyde radical, the functional group such as hydroxyl and phenyl ring, can with metal ion, formaldehyde, the activity methylene compound, primary amine, complex reaction occurs in hydrazines etc., condensation reaction etc., make ionic polymer, small molecular ion liquid of Schiff's base grafting etc., because of these materials after the imidazole type gemini ionic liquid chemical conversion of described double salicylaldehyde functionalization, may have light, electricity, the functions such as magnetic, the imidazole type gemini ionic liquid of double salicylaldehyde functionalization can be used as Kaolinite Preparation of Catalyst thus, the photo-electroluminescence material, chemical probe, probe biomolecule, the raw material of polymer electrolyte etc.
Specific embodiment
By following embodiment imidazole type gemini ionic liquid and the preparation method of the double salicylaldehyde functionalization shown in the general formula provided by the invention (I) are further specified, its purpose is to understand better content of the present invention.Therefore, imidazole type gemini ionic liquid and the preparation method of double salicylaldehyde functionalization shown in the unlisted general formula (I) should not be considered as limiting the scope of the invention among the embodiment.
The preparation of the imidazole type gemini ionic liquid (I-1) of embodiment 1 double salicylaldehyde functionalization
The preparation of the imidazole type gemini quaternary ammonium salt II-1 of step 1 double salicylaldehyde functionalization
In the four-hole boiling flask of agitator is housed, take by weighing Isosorbide-5-Nitrae-two (1,1 '-imidazolyl) butane 20 grams and be dissolved in 120 milliliters of Isosorbide-5-Nitrae-dioxane, make the Isosorbide-5-Nitrae-dioxane solution of Isosorbide-5-Nitrae-two (1,1 '-imidazolyl) butane.Take by weighing 5-chloromethyl salicylaldehyde 40 grams and be dissolved in 80 milliliters of Isosorbide-5-Nitrae-dioxane, make the Isosorbide-5-Nitrae-dioxane solution of 5-chloromethyl salicylaldehyde.1 of control 5-chloromethyl salicylaldehyde, the temperature of 4-dioxane solution is between 8～15 ℃, stir lower to 1, Isosorbide-5-Nitrae-the dioxane solution of two (1, the 1 '-imidazolyl) butane of 4-slowly adds 1 of 5-chloromethyl salicylaldehyde, in the 4-dioxane solution, react after 4 hours, temperature is brought up to 80～85 ℃, restir reaction 10 hours, the reaction product system temperature is down to 5～10 ℃, filter, filter cake uses Isosorbide-5-Nitrae-dioxane to wash 3～5 times, after the drying, make the imidazole type gemini quaternary ammonium salt II-1 of the double salicylaldehyde functionalization of 53.6 gram oyster white crystal powders, yield 89.3%, 125～127 ℃ of fusing points.Analytical data:
Ultimate analysis: C
26H
28C1
2N
4O
4Measured value (calculated value): C58.18 (58.76), H5.30 (5.31), N10.38 (10.54), Cl13.33 (13.34).
IR (KBr compressing tablet, cm
-1): 3413,3013,2863,2712,1687,1617,1564,1323.
H
1-NMR(DMSO-d
6，δ)：1，74(t，4H)，3.73(t，4H)，4.33(s，4H)，5.35(s，2H)，6.85～7.87(m，12H)，4.33(s，2H)，10.22(s，2H)。
The preparation of the imidazole type gemini ionic liquid (I-1) of step 2 double salicylaldehyde functionalization
The imidazole type gemini quaternary ammonium salt (II-1) that takes by weighing 10 gram double salicylaldehyde functionalization is dissolved in 30 milliliters of ethanol, make the ethanolic soln of II-1, taking by weighing 4.2 gram Potassium Hexafluorophosphates is dissolved in 40 milliliters of ethanol again, make the ethanolic soln of Potassium Hexafluorophosphate, control the temperature of described Potassium Hexafluorophosphate ethanolic soln between 55～60 ℃, under stirring described II-1 ethanolic soln is added in the described Potassium Hexafluorophosphate ethanolic soln, react after 6 hours, reduction reaction product system temperature to 5～8 ℃, filtration makes filter cake, uses 200 milliliters of Isosorbide-5-Nitrae-dioxane dissolving filter cakes, the elimination insolubles, gained filtrate is revolved steaming, remove most of Isosorbide-5-Nitrae-dioxane after, cooling is revolved and is steamed residue temperature to 2～5 ℃, filter, drying makes the imidazole type gemini ionic liquid (I-1) of pale yellow powder shape double salicylaldehyde functionalization, yield 95.5%, 92～94 ℃ of fusing points.
The preparation of the imidazole type gemini ionic liquid (I-2) of embodiment 2 double salicylaldehyde functionalization
According to preparation method and the step of embodiment 1, with the Isosorbide-5-Nitrae-two (1 of step 1 among the embodiment, 1 '-imidazolyl) the butane change is 1, two [2-(1, the 1 '-imidazolyl) oxyethyl group] ethane of 2-namely make the imidazole type gemini ionic liquid (I-2) of double salicylaldehyde functionalization.
The preparation of the imidazole type gemini ionic liquid (I-3) of embodiment 3 double salicylaldehyde functionalization
Preparation method and step according to embodiment 1, with 1 of step 1 among the embodiment, 4-two (1,1 '-imidazolyl) the butane change is 1,2-is two, and [2-(1,1 '-imidazolyl) oxyethyl group] ethane, the Potassium Hexafluorophosphate of step 2 changes and is Sodium tetrafluoroborate among the embodiment 1, namely makes the imidazole type gemini ionic liquid (I-3) of double salicylaldehyde functionalization.
The preparation of the imidazole type gemini ionic liquid (I-4) of embodiment 4 double salicylaldehyde functionalization
According to preparation method and the step of embodiment 1, the Isosorbide-5-Nitrae of step 1 among the embodiment 1-two (1,1 '-imidazolyl) butane changed be compound (1), the Potassium Hexafluorophosphate of step 2 changes and is fluoroboric acid among the embodiment 1
Sodium namely prepares the imidazole type gemini ionic liquid (I-4) of double salicylaldehyde functionalization, and wherein compound (1) structural formula is seen shown in the formula (1).
The preparation of the imidazole type gemini ionic liquid (I-5) of embodiment 5 double salicylaldehyde functionalization
Preparation method and step according to embodiment 1, with 1 of step 1 among the embodiment 1,4-two (1,1 '-imidazolyl) butane changes and is compound (2), the Potassium Hexafluorophosphate of step 2 changes and is Sodium tetrafluoroborate among the embodiment 1, the imidazole type gemini ionic liquid (I-5) of the double salicylaldehyde functionalization of namely making, wherein compound (2) structural formula is seen formula (2).
The character of the imidazole type gemini ionic liquid (I-1～5) of embodiment 6 double salicylaldehyde functionalization
Observe the solubility property of imidazole type gemini ionic liquid (I-1～5) in several organic solvents of double salicylaldehyde functionalization, the results are shown in Table 1.
The dissolving situation of the imidazole type gemini ionic liquid of table 1 double salicylaldehyde functionalization (I-1～5)
Claims (2)
1. the imidazole type gemini ionic liquid of a double salicylaldehyde functionalization, the structure shown in (I) that it is characterized in that having general formula:
Q is selected from its formula of (I):
C
1～C
20Saturated or unsaturated alkyl,
Or
In a kind of, described n is selected from a kind of in 1～500 positive integer; X is selected from F, Cl, Br, NO
3, HSO
4, CH
3COO, C
3F
7COO, BF
4, PF
6, SbF
6, CF
3SO
3, C
4F
9SO
3, (CF
3SO
2)
3C, (CF
3SO
2)
2A kind of among the N.
2. according to the preparation method of the imidazole type gemini ionic liquid of double salicylaldehyde functionalization claimed in claim 1, it is characterized in that realizing according to following synthetic route and preparation process:
In described synthetic route, Q is selected from:
C
1～C
20Saturated or unsaturated alkyl,
Or
In a kind of, described n is selected from a kind of in 1～500 positive integer; M among the MX is selected from K or Na, and X is selected from F, Cl, Br, NO
3, HSO
4, CH
3COO, C
3F
7COO, BF
4, PF
6, SbF
6, CF
3SO
3, C
4F
9SO
3, (CF
3SO
2)
3C, (CF
3SO
2)
2A kind of among the N;
Concrete preparation process is as follows:
Step 1 is in reactor, taking by weighing general formula (II) is dissolved in the organic solvent, make solution (1), taking by weighing the 5-chloromethyl salicylaldehyde is dissolved in the organic solvent again, make solution (2), the temperature of control solution (2) is between 5～25 ℃, under stirring solution (1) is added in the solution (2), react after 2～6 hours, temperature of reaction is brought up to 60～85 ℃, restir reaction 4～12 hours, the reaction product system temperature is down to 5～10 ℃, filters, filter cake with an organic solvent washs 3～5 times, after the drying, make general formula (III) Shuangzi imidazole type quaternary ammonium salt;
Its formula of (II) is 1: 2.0～2.5 with the mol ratio of 5-chloromethyl salicylaldehyde, described organic solvent refers to tetrahydrofuran (THF), 1,4-dioxane, glycol dimethyl ether, ethylene glycol diethyl ether, ethyl acetate, acetonitrile, acetone or methylethylketone, the consumption of described organic solvent are general formula (II) and 5-chloromethyl salicylaldehyde quality summation 2～6 times;
The Shuangzi imidazole type quaternary ammonium salt that step 2 takes by weighing structure shown in the synthetic route formula of (III) is dissolved in the Fatty Alcohol(C12-C14 and C12-C18), make solution (3), taking by weighing MX is dissolved in the Fatty Alcohol(C12-C14 and C12-C18) again, make solution (4), the temperature of control solution (4) is between 25～85 ℃, stir lower in solution (3) the adding solution (4), behind the stirring reaction 2～6 hours, the reaction product system temperature is down to-10～10 ℃, filtration makes filter cake, with an organic solvent dissolves described filter cake, the elimination insolubles, revolve and steam filtrate removal organic solvent, make the imidazole type gemini ionic liquid of the double salicylaldehyde functionalization of structure shown in the general formula (I);
Wherein said Fatty Alcohol(C12-C14 and C12-C18) refers to a kind of in methyl alcohol, ethanol, propyl alcohol or the butanols; The consumption of described Fatty Alcohol(C12-C14 and C12-C18) is general formula (III) Shuangzi imidazole type quaternary ammonium salt and MX quality summation 2～6 times; M among the described MX is selected from K or Na, and X is selected from F, Cl, Br, NO
3, HSO
4, CH
3COO, C
3F
7COO, BF
4, PF
6, SbF
6, CF
3SO
3, C
4F
9SO
3, (CF
3SO
2)
3C, (CF
3SO
2)
2A kind of among the N, the consumption of MX is 2.0～2.5 times of general formula (III) gemini quaternary ammonium salt molar weight; Described organic solvent is selected from tetrahydrofuran (THF), 1,4-dioxane, glycol dimethyl ether, ethylene glycol diethyl ether, ethyl acetate, chloroform, acetonitrile or methyl-sulphoxide, the consumption of described organic solvent are general formula (III) Shuangzi imidazole type quaternary ammonium salt and MX quality summation 2～6 times.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103193701A (en) * | 2013-03-14 | 2013-07-10 | 淮海工学院 | Functional ligand and preparation method thereof |
| CN103965111A (en) * | 2014-05-05 | 2014-08-06 | 淮海工学院 | Gemini quaternary ammonium salt containing salicylaldehyde Schiff base and preparation method thereof |
| CN109772449A (en) * | 2019-03-20 | 2019-05-21 | 淮海工学院 | A kind of polystyrene-supported polyethyleneglycol modified imidazoles coordinated ionic liquid |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105693615A (en) * | 2016-04-15 | 2016-06-22 | 南京工业大学 | Synthesizing method of imidazole type Gemini surfactant |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3642896A (en) * | 1966-09-23 | 1972-02-15 | Allen & Hanburys Ltd | Process for the preparation of alpha**1-tertiary butylaminomethyl - 4 - hydroxy-m-xylene-alpha**1 alpha**3-diol |
| CN101805386A (en) * | 2010-04-13 | 2010-08-18 | 中国科学院过程工程研究所 | Hydrocortisone production process based on ionic liquid |
| CN102020630A (en) * | 2009-09-11 | 2011-04-20 | 中国科学院兰州化学物理研究所 | Method for synthesizing trioxymethylene by catalyzing formaldehyde cyclization reaction through bifunctional ionic liquid |
| CN102134237A (en) * | 2010-12-27 | 2011-07-27 | 西北师范大学 | Crown ether ring imidazole ionic liquid |
| WO2011146326A1 (en) * | 2010-05-18 | 2011-11-24 | 3M Innovative Properties Company | Polymerizable ionic liquid compositions |
-
2012
- 2012-10-10 CN CN201210412822.1A patent/CN102924382B/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3642896A (en) * | 1966-09-23 | 1972-02-15 | Allen & Hanburys Ltd | Process for the preparation of alpha**1-tertiary butylaminomethyl - 4 - hydroxy-m-xylene-alpha**1 alpha**3-diol |
| CN102020630A (en) * | 2009-09-11 | 2011-04-20 | 中国科学院兰州化学物理研究所 | Method for synthesizing trioxymethylene by catalyzing formaldehyde cyclization reaction through bifunctional ionic liquid |
| CN101805386A (en) * | 2010-04-13 | 2010-08-18 | 中国科学院过程工程研究所 | Hydrocortisone production process based on ionic liquid |
| WO2011146326A1 (en) * | 2010-05-18 | 2011-11-24 | 3M Innovative Properties Company | Polymerizable ionic liquid compositions |
| CN102134237A (en) * | 2010-12-27 | 2011-07-27 | 西北师范大学 | Crown ether ring imidazole ionic liquid |
Non-Patent Citations (2)
| Title |
|---|
| 刘霖，等: "功能离子液体催化分子氢氧化醇为醛酮", 《应用化学》, vol. 24, no. 11, 10 November 2007 (2007-11-10), pages 1327 - 1331 * |
| 赵建章: "Schiff碱N，N-双水杨醛缩-1,6-已二胺的光致变色光谱研究", 《高等学校化学学报》, vol. 22, no. 6, 15 July 2001 (2001-07-15), pages 971 - 975 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103193701A (en) * | 2013-03-14 | 2013-07-10 | 淮海工学院 | Functional ligand and preparation method thereof |
| CN103965111A (en) * | 2014-05-05 | 2014-08-06 | 淮海工学院 | Gemini quaternary ammonium salt containing salicylaldehyde Schiff base and preparation method thereof |
| CN109772449A (en) * | 2019-03-20 | 2019-05-21 | 淮海工学院 | A kind of polystyrene-supported polyethyleneglycol modified imidazoles coordinated ionic liquid |
| CN109772449B (en) * | 2019-03-20 | 2021-09-28 | 淮海工学院 | Polystyrene-immobilized polyethylene glycol and imidazole coordination ionic liquid modified by derivative thereof |
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