CN103242176A - Functional ionic liquid based on choline chloride, and preparation method of same - Google Patents
Functional ionic liquid based on choline chloride, and preparation method of same Download PDFInfo
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Abstract
The invention belongs to the technical field of chemical materials and preparation of the same, and discloses a functional ionic liquid based on choline chloride, and a preparation method of the same. The ionic liquid has the structure shown in a formula, wherein X<-> is methoxyl negative ion, ethyoxyl negative ion, normal propyl alcohol negative ion, isopropyl alcohol negative ion, tertiary butanol negative ion, n-butyl alcohol negative ion, and on the like. The ionic liquid is excellent in solubility, can be used as a catalyst and solvent in organic synthesis, and is simple to prepare, high in yield and high in purity.
Description
Technical field
The invention belongs to chemical material and preparing technical field, specifically, relate to a kind of functional ion liquid based on choline chloride 60 and preparation method thereof.
Background technology
As everyone knows, ionic liquid is to be made of organic cation and inorganic or organic anion, is the salt of liquid state down near room temperature or room temperature.Ionic liquid has advantages such as low volatility, low melting point, structure designability, broadening window, excellent conducting performance and good solubility energy, and it all is widely used in every field.In " ionic liquid-character, preparation and application " book that Deng Youquan writes, introduced the application of ionic liquid at all kinds of organic synthesis operating units.Chinese patent CN101148392, CN1563008, CN1810757, CN1712093 etc. have set forth the application of ionic liquid in extracting and separating.Chinese patent CN101177252, CN11600429, CN101177299 etc. are successfully applied to field of nanometer technology with ionic liquid.Chinese patent CN101164122, CN101248495 etc. have reported the applicable cases of ionic liquid in electro-conductive material and conducting film preparation.At present, ionic liquid can be divided into following a few class substantially: pyridinium ion, alkyl quaternary phosphine ion and quaternary ammonium alkyl ion that the imidazol ion that alkyl replaces, alkyl replace.At present, the ionic liquid ubiquity of report preparation cost higher, have problems such as certain toxicity and non-degradable.
Summary of the invention
Choline chloride 60 (HOC
2H
4N (CH
3)
3 +Cl
-) wide material sources, price very cheap and also do not have any toxicity (document Green chemistry, 2011,13,82-90), the contriver explores the series function ionic liquid that preparation is raw material with the choline chloride 60.
It is the functional ion liquid that positively charged ion constitutes with the positive ion in the choline chloride 60 that the object of the invention is to provide a kind of, and this class preparation method of ionic liquid is provided.Ionic liquid of the present invention is cheap, low toxicity even nontoxic, and the catalyzer or the solvent that can be used as a kind of green are widely used in the organic synthesis.
The objective of the invention is to realize in the following manner:
A kind of functional ion liquid based on choline chloride 60, this functional ion liquid has following structural formula I:
Wherein, X
-Be CH
3O
-, CH
3CH
2O
-, CH
3CH
2CH
2O
-, CH
3(CH
3) CHO
-, (CH
3)
3CO
-, CH
3CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2CH
2CH
2CH
2O
-, or CH
3CH
2CH
2CH
2CH
2CH
2CH
2CH
2CH
2O
-
Preferred X
-Be methoxyl group negative ion, oxyethyl group negative ion, n-propyl alcohol negative ion, Virahol negative ion, trimethyl carbinol negative ion or propyl carbinol negative ion.
Described functional ion liquid is preferably:
The above-mentioned functions preparation method of ionic liquid may further comprise the steps: the metal-salt MX of choline chloride 60 and equimolar amount is to carry out ion exchange reaction under 60～215 ℃ in temperature, obtains functional ion liquid, and its reaction equation is as follows:
Wherein, M is Na
+, or K
+X is CH
3O
-, CH
3CH
2O
-, CH
3CH
2CH
2O
-, CH
3(CH
3) CHO
-, (CH
3)
3CO
-, CH
3CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2CH
2CH
2CH
2O
-, or CH
3CH
2CH
2CH
2CH
2CH
2CH
2CH
2CH
2O
-
X is preferably methoxyl group negative ion, oxyethyl group negative ion, n-propyl alcohol negative ion, Virahol negative ion, trimethyl carbinol negative ion or propyl carbinol negative ion.
The solvent that above-mentioned ion exchange reaction adopts is methyl alcohol, ethanol, n-propyl alcohol, Virahol, the trimethyl carbinol or propyl carbinol.
Above-mentioned preparation method's preferable reaction temperature is 60-100 ℃, and most preferably temperature of reaction is 64.5-97.1 ℃.Reaction times can be 12～24 hours.Reaction finishes, can be under 60～80 ℃ of conditions vacuum-drying 5～10 hours, obtain light yellow transparent liquid, be in a liquid state under the room temperature, its structural formula is as follows:
The reactant that adopts of the present invention particularly
CH
3CH
2CH
2CH
2CH
2CH
2CH
2ONa, CH
3CH
2CH
2CH
2CH
2CH
2CH
2CH
2ONa, CH
3CH
2CH
2CH
2CH
2CH
2CH
2CH
2CH
2ONa, CH
3CH
2CH
2CH
2CH
2CH
2CH
2OK, CH
3CH
2CH
2CH
2CH
2CH
2CH
2CH
2OK, CH
3CH
2CH
2CH
2CH
2CH
2CH
2CH
2CH
2OK, structure is bigger, reacts the sterically hindered bigger of position, sees on the microcosmic to be difficult to reaction, but overcomes above-mentioned difficulties in the preparation process of the present invention, still obtains the higher ionic liquid of catalytic performance.
The ionic liquid of preparation can be used
1H NMR,
13C NMR structural confirmation.
Prior art is compared, and the present invention has following unusual effect:
(1) the present invention prepares the ion exchange reaction that functional ion liquid adopts and belongs to neutralization reaction; technology is simple, and facility investment is few, need not nitrogen protection; gained ionic liquid product yield can be up to 97%, purity can be up to 98%, and no any by product produces in the reaction process.
(2) functional ion liquid of the present invention is good to common organic reagent and material dissolves, and because the existence of hydroxyl in the positively charged ion has certain alkalescence and hydrogen bond donor characteristics, and the useful as catalysts solvent of holding concurrently is applied in the organic synthesis.Functional ion liquid of the present invention is particularly useful for catalysis Knoevenagel condensing aromatic aldehydes and active methylene compound reaction, the catalytic preparation benzopyran derivatives, catalytic preparation beta-amino ketones, ester, nitrile and amide derivatives, and make product have higher yield and purity.
Embodiment
The present invention will be further described below with reference to embodiment, and embodiments of the invention only are used for explanation technical scheme of the present invention, and non-limiting the present invention.
Embodiment 1
Experimental installation mainly is there-necked flask, in order to stir fully, adopts mechanical stirring.The choline chloride 60 of accurate weighing and the methanol solution that contains sodium methylate (with mole such as choline chloride 60) are placed flask, flask places oil bath, under the high-speed stirring, 64.5 ℃ were reacted 12 hours, cooling, filtration, filtrate is washed with ether, underpressure distillation desolventizing then, 60 ℃ of dryings of gained liquid vacuum 5 hours obtain light yellow transparent liquid, yield 97%, purity are 98%.The ionic liquid for preparing:
1H NMR (400M, D
2O): δ 4.05 (m, 2H), 3.49 (t, 2H, J=5.2Hz), 3.36 (s, 3H), 3.20 (s, 9H);
13CNMR (100M, D
2O): δ 67.86,55.73,53.91,53.84,48.92.
Reaction formula is:
Embodiment 2
Experimental installation mainly is there-necked flask, in order to stir fully, adopts mechanical stirring.The choline chloride 60 of accurate weighing and the ethanolic soln that contains sodium ethylate (with mole such as choline chloride 60) are placed flask, flask places oil bath, under the high-speed stirring, 78.4 ℃ were reacted cold filtration 12 hours, filtrate is washed with ether, underpressure distillation desolventizing then, 70 ℃ of dryings of gained liquid vacuum 5 hours obtain light yellow transparent liquid, yield 93%, purity are to be 96%.The ionic liquid for preparing:
1H NMR (400M, D
2O): δ 3.98 (m, 2H), 3.44 (t, 2H, J=4.8Hz), 3.13 (s, 9H), 2.42 (q, 2H, J=7.2Hz), 1.82 (t, 3H, J=7.2Hz);
13C NMR (100M, D
2O): δ 67.42,55.57,53.84,35.6,23.46.
Reaction formula is:
Embodiment 3
Experimental installation mainly is there-necked flask, in order to stir fully, adopts mechanical stirring.The choline chloride 60 of accurate weighing and the n-propyl alcohol solution that contains n-propyl alcohol sodium (with mole such as choline chloride 60) are placed flask, flask places oil bath, under the high-speed stirring, 97.1 ℃ were reacted cold filtration 12 hours, filtrate is washed with ether, underpressure distillation desolventizing then, 80 ℃ of dryings of gained liquid vacuum 5 hours obtain light yellow transparent liquid, yield 96%, purity are 98%.The ionic liquid for preparing:
1H NMR (400M, D
2O): δ 4.03 (m, 2H), 3.48 (t, 2H, J=5.2Hz), 3.16 (s, 9H), 2.26 (t, 2H, J=7.2Hz), 1.82 (m, 2H), 0.86 (t, 3H, J=7.2Hz);
13C NMR (100M, D
2O): δ 67.49,55.68,54.02,53.97 .53.94,39.73,25.8,13.46.
Reaction formula is:
Embodiment 4
Experimental installation mainly is there-necked flask, in order to stir fully, adopts mechanical stirring.The choline chloride 60 of accurate weighing and the t-butanol solution that contains potassium tert.-butoxide (with mole such as choline chloride 60) are placed flask, flask places oil bath, under the high-speed stirring, 82.4 ℃ were reacted cold filtration 24 hours, filtrate is washed with ether, underpressure distillation desolventizing then, 60 ℃ of dryings of gained liquid vacuum 10 hours obtain light yellow transparent liquid, yield 92%, purity are 97%.The ionic liquid for preparing:
1H NMR (400M, D
2O): δ 4.02 (m, 2H), 3.48 (t, 2H, J=4.8Hz), 3.16 (s, 9H), 1.09 (s, 9H);
13C NMR (100M, D
2O): δ 70.42,58.61,56.83,14.82.
Reaction formula is:
Embodiment 5
Experimental installation mainly is there-necked flask, in order to stir fully, adopts mechanical stirring.The choline chloride 60 of accurate weighing and the enanthol solution that contains enanthol potassium (with mole such as choline chloride 60) are placed flask, flask places oil bath, under the high-speed stirring, 176 ℃ were reacted cold filtration 24 hours, filtrate is washed with ether, underpressure distillation desolventizing then, 80 ℃ of dryings of gained liquid vacuum 5 hours obtain light yellow transparent liquid, yield 86%, purity are 95%.The ionic liquid for preparing:
1H NMR (400M, D
2O): δ 3.95 (m, 2H), 3.46 (t, 2H, J=7.2Hz), 3.15 (s, 9H), 2.24 (t, 2H, J=7.2Hz), 1.96-1.71 (m, 10H), 0.88 (t, 3H, J=7.2Hz);
13C NMR (100M, D
2O): δ 67.52,56.01,53.85,54.05 .53.88,40.62,31.68,29.82,28.52,27.63,26.32,13.23.
Reaction formula is:
Embodiment 6
Experimental installation mainly is there-necked flask, in order to stir fully, adopts mechanical stirring.The choline chloride 60 of accurate weighing and the octanol solution that contains octanol potassium (with mole such as choline chloride 60) are placed flask, flask places oil bath, under the high-speed stirring, 184 ℃ were reacted cold filtration 24 hours, filtrate is washed with ether, underpressure distillation desolventizing then, 80 ℃ of dryings of gained liquid vacuum 5 hours obtain light yellow transparent liquid, yield 83%, purity are 96%.The ionic liquid for preparing:
1H NMR (400M, D
2O): δ 4.02 (m, 2H), 3.48 (t, 2H, J=4.8Hz), 3.18 (s, 9H), 2.31 (t, 2H, J=7.2Hz), 1.89-1.73 (m, 12H), 0.83 (t, 3H, J=7.2Hz);
13C NMR (100M, D
2O): δ 67.58,56.03,53.89,54.55 .54.03,40.68,31.75,30.06,29.38,28.63,27.63,26.33,13.35.
Reaction formula is:
Embodiment 7
Experimental installation mainly is there-necked flask, in order to stir fully, adopts mechanical stirring.The choline chloride 60 of accurate weighing and the nonyl alcohol solution that contains nonyl alcohol potassium (with mole such as choline chloride 60) are placed flask, flask places oil bath, under the high-speed stirring, 215 ℃ were reacted cold filtration 24 hours, filtrate is washed with ether, underpressure distillation desolventizing then, 80 ℃ of dryings of gained liquid vacuum 5 hours obtain light yellow transparent liquid, yield 85%, purity are 96%.The ionic liquid for preparing:
1H NMR (400M, D
2O): δ 4.05 (m, 2H), 3.50 (t, 2H, J=4.8Hz), 3.15 (s, 9H), 2.35 (t, 2H, J=7.2Hz), 1.92-1.68 (m, 14H), 0.91 (t, 3H, J=7.2Hz);
13C NMR (100M, D
2O): δ 67.51,56.11,53.85,55.12,54.03,41.05,31.68,30.73,29.78,29.14,28.65,27.22,26.39,14.08.
Reaction formula is:
Embodiment 8
The ionic liquid that phenyl aldehyde (5mmol), propane dinitrile (6mmol), Ketene dimethyl (6mmol), 5mL water, 0.25mmol are prepared according to embodiment 7 methods joins in the 50mL single port bottle, 80 ℃ are stirred 2 hours TLC and detect, raw material disappears, filter, the vacuum-drying filter cake obtains product, yield: 90%, content 98%.The products obtained therefrom structural confirmation:
1H NMR (400MHz, DMSO-d
6) (ppm): 7.29-7.10 (m, 5H), 7.03 (br, s, 2H), 4.15 (s, 1H), 2.51 (br, s, 3H), 2.25 (d, 1H, J=16Hz), 2.08 (d, 1H, J=16Hz), 1.05 (s, 3H), 0.96 (s, 3H);
13C NMR (100MHz, DMSO-d
6) (ppm): 196.3,163.2,159.3,145.6,128.9,127.9,127.2,121.1,113.4,60.1,50.8.
Embodiment 9
The ionic liquid that morpholine (5mmol), methyl acrylate (5.5mmol), 1mmol are prepared according to embodiment 7 methods joins in the 50mL single port bottle successively, stirring at room 2 hours, TLC detects, raw material disappears, use the extracted with diethyl ether reaction solution, merge organic phase, column chromatography for separation obtains product, yield 88%, content 96%.The products obtained therefrom structural confirmation:
1H NMR (400MHz, CDCl
3) (ppm): 3.66 (s, 3H, OCH
3), 3.67-3.65 (m, 4H, morpholinyl), 2.65 (t, 2H, J=6Hz, CH
2), 2.48 (t, 2H, J=6Hz, CH
2), 2.43-2.41 (m, 4H, morpholinyl);
13C NMR (100MHz, CDCl
3) (ppm): 172.8,66.8,53.8,53.3,51.6,31.7.
Embodiment 10
The ionic liquid that phenyl aldehyde (5mmol), propane dinitrile (6mmol), 4mL water, 0.25mmol are prepared according to embodiment 7 methods joins in the 50mL single port bottle successively, 10 minutes TLC of stirring at room detect, raw material disappears, filter, the vacuum-drying filter cake obtains product, yield 96%, content 98%.The products obtained therefrom structural confirmation:
1H NMR (400MHz, CDCl
3) (ppm): 7.91 (d, 2H, J=7.6Hz, ArH), 7.79 (s, 1H, C=CH), 7.64 (t, 1H, J=7.6Hz, ArH), 7.27 (t, 2H, J=7.6Hz, ArH), 7.27 (t, 2H, J=7.6Hz, ArH);
13C NMR (100MHz, CDCl
3) (ppm): 160.0,134.6,130.9,130.7,129.6,113.7,112.5,82.7.
Embodiment 11
The ionic liquid that phenyl aldehyde (5mmol), propane dinitrile (6mmol), Ketene dimethyl (6mmol), 5mL water, 0.25mmol are prepared according to embodiment 6 methods joins in the 50mL single port bottle, 80 ℃ are stirred 2 hours TLC and detect, raw material disappears, filter, the vacuum-drying filter cake obtains product, yield: 88%, content 96%.Products obtained therefrom structure NMR is with embodiment 8.
Embodiment 12
The ionic liquid that morpholine (5mmol), methyl acrylate (5.5mmol), 1mmol are prepared according to embodiment 6 methods joins in the 50mL single port bottle successively, stirring at room 1.5 hours, TLC detects, raw material disappears, use the extracted with diethyl ether reaction solution, merge organic phase, column chromatography for separation obtains product, yield 90%, content 98%.Products obtained therefrom NMR structure is with embodiment 9.
Embodiment 13
The ionic liquid that phenyl aldehyde (5mmol), propane dinitrile (6mmol), 4mL water, 0.25mmol are prepared according to embodiment 6 methods joins in the 50mL single port bottle successively, 10 minutes TLC of stirring at room detect, raw material disappears, filter, the vacuum-drying filter cake obtains product, yield 93%, content 99%.Products obtained therefrom NMR structure is with embodiment 10.
Embodiment 14
The ionic liquid that phenyl aldehyde (5mmol), propane dinitrile (6mmol), Ketene dimethyl (6mmol), 5mL water, 0.25mmol are prepared according to embodiment 5 methods joins in the 50mL single port bottle, 80 ℃ are stirred 1.5 hours TLC and detect, raw material disappears, filter, the vacuum-drying filter cake obtains product, yield: 93%, content 98%.Products obtained therefrom NMR structure is with embodiment 8.
Embodiment 15
The ionic liquid that morpholine (5mmol), methyl acrylate (5.5mmol), 1mmol are prepared according to embodiment 5 methods joins in the 50mL single port bottle successively, stirring at room 1 hour, TLC detects, raw material disappears, use the extracted with diethyl ether reaction solution, merge organic phase, column chromatography for separation obtains product, yield 95%, content 98%.Products obtained therefrom NMR structure is with embodiment 9.
Embodiment 16
The ionic liquid that phenyl aldehyde (5mmol), propane dinitrile (6mmol), 4mL water, 0.25mmol are prepared according to embodiment 5 methods joins in the 50mL single port bottle successively, 10 minutes TLC of stirring at room detect, raw material disappears, filter, the vacuum-drying filter cake obtains product, yield 96%, content 98%.Products obtained therefrom NMR structure is with embodiment 10.
Claims (9)
1. the functional ion liquid based on choline chloride 60 is characterized in that, described functional ion liquid has following structural formula I:
Wherein, X
-Be CH
3O
-, CH
3CH
2O
-, CH
3CH
2CH
2O
-, CH
3(CH
3) CHO
-, (CH
3)
3CO
-, CH
3CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2CH
2CH
2CH
2O
-Or CH
3CH
2CH
2CH
2CH
2CH
2CH
2CH
2CH
2O
-
2. functional ion liquid as claimed in claim 1 is characterized in that, described X
-Be methoxyl group negative ion, oxyethyl group negative ion, n-propyl alcohol negative ion, Virahol negative ion, trimethyl carbinol negative ion or propyl carbinol negative ion.
3. functional ion liquid as claimed in claim 1 is characterized in that, described functional ion liquid is
4. the preparation method of the described functional ion liquid of claim 1, it is characterized in that this method may further comprise the steps: the metal-salt MX of choline chloride 60 and equimolar amount is to carry out ion exchange reaction under 60～215 ℃ in temperature, obtain functional ion liquid, its reaction equation is as follows:
Wherein, M is Na
+, or K
+X is CH
3O
-, CH
3CH
2O
-, CH
3CH
2CH
2O
-, CH
3(CH
3) CHO
-, (CH
3)
3CO
-, CH
3CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2CH
2CH
2O
-, CH
3CH
2CH
2CH
2CH
2CH
2CH
2CH
2O
-Or CH
3CH
2CH
2CH
2CH
2CH
2CH
2CH
2CH
2O
-
5. preparation method as claimed in claim 4 is characterized in that, described X is methoxyl group negative ion, oxyethyl group negative ion, n-propyl alcohol negative ion, Virahol negative ion, trimethyl carbinol negative ion or propyl carbinol negative ion.
6. preparation method as claimed in claim 4 is characterized in that, described temperature of reaction is 60-100 ℃, and the reaction times is 12-24 hour.
7. preparation method as claimed in claim 4 is characterized in that, the solvent that described ion exchange reaction adopts is methyl alcohol, ethanol, n-propyl alcohol, Virahol, the trimethyl carbinol or propyl carbinol.
8. preparation method as claimed in claim 7 is characterized in that, after ion exchange reaction is finished, and cooling, filtration, after filtrate is washed with ether, the underpressure distillation desolventizing.
9. as claim 4 or 7 described preparation methods, it is characterized in that, with the vacuum-drying 5～10 hours under 60～80 ℃ of conditions of gained liquid.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103936768A (en) * | 2014-04-30 | 2014-07-23 | 安徽工业大学 | Green catalysis preparation method of thiazole[3,2-alpha] pyridine derivative |
| CN104016866A (en) * | 2014-05-20 | 2014-09-03 | 上海应用技术学院 | Method for preparing di-2-ethyhexyl carbonate |
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| CN103936768A (en) * | 2014-04-30 | 2014-07-23 | 安徽工业大学 | Green catalysis preparation method of thiazole[3,2-alpha] pyridine derivative |
| CN104016866A (en) * | 2014-05-20 | 2014-09-03 | 上海应用技术学院 | Method for preparing di-2-ethyhexyl carbonate |
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| CN103242176B (en) | 2015-12-09 |
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