CN1631539A - Amino acid salt ion liquid and its preparation - Google Patents
Amino acid salt ion liquid and its preparation Download PDFInfo
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Abstract
The invention offers a new kind of amino acids sald ion liquid and its producing way. The amino acids sald ion molecular formula is [A]n plus Xn minus, [A]n+ is amino acids positive ion, Xn is one yuan strong acid, chosen from nitric acid, 4F-B acid, 6-F-P acid, 3-F yi acid, HBr acid, HI acid, one sulphur acid, Cl sulphur acid, benzene sulphur acid, n is 1--4. The producing way is: 1. Mix the amino acids and one of nitric acid, 4F-B acid, 6-F-P acid, 3-F yi acid, HBr acid, HI acid, one sulphur acid, Cl sulphur acid, benzene sulphur acid: 2. Vaporize the liquid to dissolve the water, and we get the amino acids salt ion liquid. The amino acids salt ion liquid has the feature of ion liquid, at the same time, it has the feature of hand material and B acid, and it costs little, produce easily: no pollution and other things in the producing: the pure degree of the product is high, so it is proper to industrial production and application.
Description
Technical Field
The invention relates to an ionic liquid and a preparation method thereof, in particular to a novel amino acid salt ionic liquid and a preparation method thereof, belonging to the technical field of novel chemical materials and preparation thereof.
Background
The ionic liquid is a low-temperature molten salt, is a low-viscosity liquid completely composed of ions at the temperature close to room temperature (<150 ℃), and is generally composed of organic cations and inorganic or organic anions. The study of ionic liquids dates back to 1914, the first study was ethylamine nitrate. Ionic liquids have been used as an excellent electrolyte, and early research on ionic liquids has focused on the field of electrochemistry. By the middle of the 80's of the 20 th century, it was discovered that ionic liquid is a good solvent and a completely new catalytic material, and has properties incomparable with organic solvents and traditional catalysts. In the field of catalytic research, ionic liquids replace traditional catalysts and organic solvents, and improve a plurality of well-known chemical reaction processes, such as Diels-Alder reaction, Friedel-Crafts reaction, Heck reaction, hydrogenation reaction, olefin hydroformylation reaction and the like. Research shows that the ionic liquid can replace traditional catalyst and organic solvent and raise reaction activity greatly. The organic solvent has the advantages of non-volatility, adjustable polarity, higher thermal stability and the like, can provide a non-aqueous environment, is easy to recycle, has unique performances incomparable with a plurality of molecular solvents, and is considered as a green solvent capable of replacing common volatile organic solvents. In the 80 s, research institutes such as BP corporation, british, and IFP of france began to more systematically explore the possibility of ionic liquids as solvents and catalysts. In the 90 s, the successful synthesis of a series of ionic liquids with stable performance makes the application research of the ionic liquids in the fields of catalysis and organic synthesis active. The cations of the existing ionic liquids consist of quaternary alkylammonium cations or quaternary alkylammonium phosphonium cations, the most common of which are N, N-dialkylimidazolium cations, N-alkylpyridinium cations, and the anions are often Cl-、Br-、AlCl4 -、BF4 -、PF6 -、NO3 -、(CF3SO3)2N-、CF3COO-And a monovalent anion. The ionic liquid obtained by combining different anions and cations has different physical properties and chemical properties, and the research on the correlation between the property change and the structure change of the combined ionic liquid is the application research of the ionic liquidThe important contents of (a). In recent years, the variety of ionic liquids has increased rapidly, for example, patent document CN1383920 describes chiral ionic liquids of L-amino acid sulfate type and a preparation method thereof, and patent document CN1383921 describes chiral ionic liquids of L-amino acid sulfate typeA body and a method of making the same. However, the monobasic strong acid amino acid salt ionic liquid related to the invention is not disclosed so far, and the preparation method thereof is also mentioned for the first time by the invention.
Disclosure of Invention
The invention aims to provide a novel amino acid salt ionic liquid and a preparation method of the ionic liquid.
According to one aspect of the present invention, the amino acid salt ionic liquid provided by the present invention has the following general formula:
[A]n+Xn -
wherein [ A]is]n+Is an amino acid cation selected from the group consisting of glycine, D-alanine, L-alanine, DL-alanine, D-valine, L-valine, DL-valine, D-leucine, L-leucine, DL-leucine, D-isoleucine, L-isoleucine, DL-isoleucine, D-phenylalanine, L-phenylalanine, DL-phenylalanine, D-cysteine, L-cysteine, DL-cysteine, D-cystine, L-cystine, DL-cystine, D-threonine, L-threonine, DL-threonine, D-glutamic acid, L-glutamic acid, DL-glutamic acid, D-glutamine, L-glutamine, DL-glutamine, D-aspartic acid, L-aspartic acid, DL-aspartic acid, D-asparagine, L-asparagine, DL-asparagine, D-methionine, L-methionine, DL-methionine, D-serine, L-serine, DL-serine, D-proline, L-tyrosine, L-tryptophan, L-tyrosine, L-arginine, L-tyrosine, L-arginine, L-4-histidine, L-arginine, L-lysine, L-arginine, L-threonine, L-cysteine, L-threonine, L-glutamine, L-cysteine, L-threonine, L-cysteine, L-glutamine, LAcid, 3-aminoisobutyric acid, 2-aminopentanoic acid, 2-aminocaproic acid, 6-aminocaproic acid, o-aminophenylpropionic acid, p-aminophenylpropionic acid, m-aminophenylpropionic acid.
Further, an anion X in the formulan -Is a monobasic strong acid radical which can be any one of nitrate radical, tetrafluoroborate radical, hexafluorophosphate radical, trifluoroacetate radical, hydrobromate radical, hydroiodide radical, methanesulfonate radical, chlorosulfonate radical, benzenesulfonate radical and p-methylbenzenesulfonate radical.
Further, the value range of n in the general formula is 1 to 4 according to different amino acid cations.
According to another aspect of the present invention, the present invention also provides a method forpreparing an amino acid salt ionic liquid, which comprises the following steps:
(1) directly adding amino acid and monobasic strong acid according to the molar ratio of 1: 1 to 1: 4;
(2) volatilizing the liquid obtained in the step (1) to remove water to obtain the amino acid salt ionic liquid.
The amino acid cation is selected from glycine, D-alanine, L-alanine, DL-alanine, D-valine, L-valine, D-leucine, L-leucine, DL-leucine, D-isoleucine, L-isoleucine, DL-isoleucine, D-phenylalanine, L-phenylalanine, DL-phenylalanine, D-cysteine, L-cysteine, D-cystine, L-cystine, DL-cystine, D-threonine, L-threonine, DL-threonine, D-glutamic acid, L-glutamic acid, DL-glutamic acid, D-glutamine, L-glutamine, DL-glutamine, D-aspartic acid, L-aspartic acid, DL-aspartic acid, D-asparagine, L-asparagine, DL-methionine, D-arginine, L-amino-tyrosine, L-alanine, L-arginine, L-valine, L-arginine, L-tyrosine, L-valine, L-arginine, L-valine, L-arginine, L-leucine, L-threonine, L-glutamine, L-arginine, L.
The amino acid salt ionic liquid provided by the invention mainly comprises the following components: glycine nitrate ionic liquid, glycine tetrafluoroborate ionic liquid, glycine hexafluorophosphate ionic liquid, D-alanine nitrate ionic liquid, L-alanine trifluoroacetate ionic liquid, L-alanine methanesulfonate ionic liquid, L-alanine chlorosulfonate ionic liquid, L-alanine benzenesulfonate ionic liquid, L-alanine p-toluenesulfonate ionic liquid, L-leucine hydrobromide ionic liquid, DL-valine hydroiodide ionic liquid, L-histidine nitrate ionic liquid, L-arginine nitrate ionic liquid, 6-aminocaproic acid nitrate ionic liquid.
Compared with the prior art, the amino acid salt ionic liquid and the preparation method thereof provided by the invention have the following remarkable effects:
1. the invention provides a new type of ionic liquid, and develops a new type of ionic liquid;
2. the raw materials for preparing the product provided by the invention are easy to obtain, and the price is low, so the preparation cost is low;
3. the method provided by the invention utilizes direct addition reaction, is easy to operate, requires simple equipment, can obtain very pure products, and is suitable for large-scale production and application;
4. the amino acid salt ions provided by the invention have the characteristics of ionic liquid and chiral substances: such as chiral separation, chiral catalysis, and the nature of chiral solvents;
5. the amino acid salt ions provided by the invention have the characteristics of ionic liquid and Bronsted acid acidity, and can replace solid acid to be used as an acidic material;
6. according to the method provided by the invention, the preparation process is an atom economic reaction without discharging pollutants, and belongs to an environment-friendly green preparation process.
Detailed Description
The invention is further illustrated by the following preferred examples.
Example 1: glycine nitrate ionic liquid and preparation method thereof
3.75g (0.05mol) of glycine and 4.85g (0.05mol) of 65% nitric acid are dissolved in 20mL of water according to the molar ratio of 1: 1, the solution is volatilized in an oil bath at 60 ℃ to remove water, the solution is dried for 24 hours in vacuum to obtain colorless transparent liquid, and the colorless transparent liquid is cooled to obtain white solid, namely the glycine nitrate ionic liquid. The reaction formula is as follows:
example 2: glycine tetrafluoroborate ionic liquid and preparation method thereof
3.75g (0.05mol) of glycine and 10.98g (0.05mol) of 40% tetrafluoroboric acid are dissolved in 20mL of water according to the molar ratio of 1: 1, the solution is volatilized in an oil bath at 60 ℃ to remove water, and the solution is dried in vacuum for 24 hours to obtain colorless transparent liquid, namely the tetrafluoroborate ionic liquid of the glycine. The reaction formula is as follows:
example 3: glycine hexafluorophosphate ionic liquid and preparation method thereof
3.75g (0.05mol) of glycine and 12.16g (0.05mol) of 60% hexafluorophosphoric acid are dissolved in 20mL of water according to the molar ratio of 1: 1, the solution is volatilized in an oil bath at 60 ℃ to remove water, the solution is dried for 24 hours in vacuum to obtain colorless transparent liquid, and the colorless transparent liquid is cooled to obtain white solid, namely the hexafluorophosphoric acid glycine ionic liquid. The reaction formula is as follows:
example 4: d-alanine nitrate ionic liquid and preparation method thereof
Dissolving 4.46g (0.05mol) of D-alanine and 4.85g (0.05mol) of 65% nitric acid in 20mL of water according to the molar ratio of 1: 1, volatilizing the water of the solution in an oil bath at 60 ℃, drying for 24 hours in vacuum to obtain colorless transparent liquid, and cooling to obtain white solid, namely D-alanine nitrate ionic liquid. The reaction formula isas follows:
example 5: l-alanine trifluoroacetate ionic liquid and preparation method thereof
Dissolving 4.46g (0.05mol) of L-alanine and 5.75g (0.05mol) of trifluoroacetic acid in 10mL of water according to the molar ratio of 1: 1, volatilizing the solution in an oil bath at 60 ℃ to remove water, drying for 24 hours in vacuum to obtain colorless transparent liquid, and cooling to obtain white solid, namely the L-alanine trifluoroacetate ionic liquid. The reaction formula is as follows:
example 6: l-alanine mesylate ionic liquid and preparation method thereof
Dissolving 4.46g (0.05mol) of L-alanine and 4.81g (0.05mol) of methanesulfonic acid in 20mL of water according to the molar ratio of 1: 1, volatilizing the solution in an oil bath at 60 ℃ to remove water, drying for 24 hours in vacuum to obtain colorless transparent liquid, and cooling to obtain white solid, namely the L-alanine methanesulfonate ionic liquid. The reaction formula is as follows:
example 7: l-alanine chlorosulfonate ionic liquid and preparation method thereof
Dissolving 4.46g (0.05mol) of L-alanine and 5.83g (0.05mol) of chlorosulfonic acid in 20mL of water according to the molar ratio of 1: 1, volatilizing the water of the solution in an oil bath at 60 ℃, drying for 24 hours in vacuum to obtain colorless transparent liquid, and cooling to obtain white solid, namely the L-alanine chlorosulfonate ionic liquid. The reaction formula is asfollows:
example 8: l-alanine benzene sulfonate ionic liquid and preparation method thereof
Dissolving 4.46g (0.05mol) of L-alanine and 7.91g (0.05mol) of benzenesulfonic acid in 20mL of water according to the molar ratio of 1: 1, volatilizing the solution in an oil bath at 60 ℃ to remove water, and drying in vacuum for 24 hours to obtain colorless transparent liquid, namely the L-alanine benzene sulfonate ionic liquid. The reaction formula is as follows:
example 9: l-alanine p-toluenesulfonate ionic liquid and preparation method thereof
Dissolving 4.46g (0.05mol) of L-alanine and 9.51g (0.05mol) of p-toluenesulfonic acid in 20mL of water according to the molar ratio of 1: 1, volatilizing the solution in an oil bath at 60 ℃ to remove water, drying for 24 hours in vacuum to obtain colorless transparent liquid, and cooling to obtain a white solid, namely the L-alanine p-toluenesulfonic acid salt ionic liquid. The reaction formula is as follows:
example 10: l-leucine hydrobromide ionic liquid and preparation method thereof
Dissolving 6.56g (0.05mol) of L-leucine and 4.85g (0.05mol) of 65% nitric acid in 20mL of water according to a molar ratio of 1: 1, volatilizing the solution in an oil bath at 60 ℃ to remove water, drying for 24 hours in vacuum to obtain colorless transparent liquid, and cooling to obtain a white solid, namely the L-leucine hydrobromide ionic liquid. The reaction formula is as follows:
example 11: DL-valine hydroiodide ionic liquid and preparation method thereof
According to the molar ratio of 1: 1, 5.86g (0.05mol) of DL-valine and 4.85g (0.05mol) of 65% nitric acid are dissolved in 30mL of water, the solution is volatilized in an oil bath at 60 ℃ to remove water, vacuum drying is carried out for 24 hours to obtain colorless transparent liquid, and cooling is carried out to obtain white solid, namely the DL-valine hydroiodide ionic liquid. The reaction formula is as follows:
example 12: preparation method of L-histidine nitrate ionic liquid
3.88g (0.025mol) of L-histidine and 4.85g (0.05mol) of 65% nitric acid are dissolved in 20mL of water according to the molar ratio of 1: 2, the solution is volatilized in an oil bath at 60 ℃ to remove water, the solution is dried for 24 hours in vacuum to obtain colorless transparent liquid, and the colorless transparent liquid is cooled to obtain white solid, namely the L-histidine nitrate ionic liquid. The reaction formula is as follows:
example 13: l-arginine nitrate ionic liquid and preparation method thereof
Dissolving 2.61g (0.015mol) of L-arginine and 5.82g (0.06mol) of 65% nitric acid in 30mL of water according to the molar ratio of 1: 4, volatilizing the solution in an oil bath at 60 ℃ to remove water, drying for 24 hours in vacuum to obtain colorless transparent liquid, and cooling to obtain white solid, namely the L-arginine nitrate ionic liquid. The reaction formula is as follows:
example 14: 6-aminocaproic acid nitrate ionic liquid
6.56g (0.05mol) of 6-aminocaproic acid and 4.85g (0.05mol) of 65% nitric acid are dissolved in 20mL of water according to the molar ratio of 1: 1, the solution is volatilized in an oil bath at 60 ℃ to remove water, the solution is dried in vacuum for 24 hours to obtain colorless transparent liquid, and the colorless transparent liquid is cooled to obtain white solid, namely 6-aminocaproic acid nitrate ionic liquid. The reaction formula is as follows:
Claims (6)
1. an amino acid salt ionic liquid, which has a molecular formula as follows:
[A]n+Xn -
characterized in that in the general formula of the molecular formula, [ A]]n+Is an amino acid cation, an anion Xn -Is a monobasic strong acid radical, and the value range of n is 1 to 4.
2. The amino acid salt ionic liquid of claim 1, wherein the strong monobasic acid is selected from the group consisting of: nitrate radical, tetrafluoroborate radical, hexafluorophosphate radical, trifluoroacetate radical, hydrobromate radical, hydroiodide radical, methanesulfonate radical, chlorosulfonate radical, benzenesulfonate radical and p-methylbenzenesulfonate radical.
3. The amino acid salt ionic liquid according to claim 1 or 2, wherein the amino acid is selectedfrom the group consisting of glycine, D-alanine, L-alanine, DL-alanine, D-valine, L-valine, DL-valine, D-leucine, L-leucine, D-isoleucine, L-isoleucine, DL-isoleucine, D-phenylalanine, L-phenylalanine, DL-phenylalanine, D-cysteine, L-cysteine, DL-cysteine, D-cystine, L-cystine, DL-cystine, D-threonine, L-threonine, DL-threonine, D-glutamic acid, L-glutamic acid, DL-glutamic acid, D-glutamine, L-glutamine, DL-glutamine, D-asparagine, D-aspartic acid, L-aspartic acid, DL-aspartic acid, D-asparagine, L-asparagine, DL-asparagine, D-methionine, L-methionine, DL-methionine, D-serine, L-proline, L-aspartic acid, L-histidine, L-arginine, L-alanine, L-histidine, L-arginine, L-amino-arginine, L-tyrosine, L-arginine, L-tyrosine, L-amino-tyrosine, L-phenylalanine, L-tyrosine, L-aspartic acid, L-histidine, L-arginine, L-tyrosine, D-tyrosine, L-tyrosine, D-aspartic acid, L-tyrosine, D-tyrosine, L-aspartic acid, L-histidine, D-histidine, L-histidine.
4. A preparation method of an amino acid salt ionic liquid comprises the following steps:
(1) directly adding amino acid and monobasic strong acid according to the molar ratio of 1: 1 to 1: 4;
(2) volatilizing the liquid obtained in the step (1) to remove water to obtain the amino acid salt ionic liquid.
5. The method of claim 4, wherein the strong monobasic acid is selected from the group consisting of: nitric acid, tetrafluoroboric acid, hexafluorophosphoric acid, trifluoroacetic acid, hydrobromic acid, hydroiodic acid, methanesulfonic acid, chlorosulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid.
6. The method for producing an amino acid salt ionic liquid according to claim 4 or 5, wherein the amino acid is selected from the group consisting of glycine, D-alanine, L-alanine, DL-alanine, D-valine, L-valine, DL-valine, D-leucine, L-leucine, D-isoleucine, L-isoleucine, DL-isoleucine, D-phenylalanine, L-phenylalanine, DL-phenylalanine, D-cysteine, L-cysteine, D-cystine, L-cystine, DL-cystine, D-threonine, L-threonine, DL-threonine, D-glutamic acid, L-glutamic acid, DL-glutamic acid, D-glutamine, L-glutamine, DL-asparagine, D-aspartic acid, DL-aspartic acid, D-asparagine, L-asparagine, DL-methionine, L-methionine, DL-methionine, D-serine, L-aspartic acid, L-histidine, L-arginine, L-histidine, L-arginine, L-2-histidine, L-alanine, L-arginine, L-threonine, L-glutamic acid, L-threonine, L-glutamic acid, L-glutamine, L-glutamic acid, L-arginine, L-glutamic acid, L-glutamic.
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