CN111909093B - Method for synthesizing ionic liquid by aqueous two-phase synthesis - Google Patents
Method for synthesizing ionic liquid by aqueous two-phase synthesis Download PDFInfo
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
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Abstract
The invention belongs to the field of chemical synthesis, and discloses a method for synthesizing ionic liquid by using aqueous two phases, which comprises the following steps: cationic precursor [ Cat ]]+[X]‑And an anionic precursor [ M]+[A]‑Dissolving in water, adding layering reagent, stirring for reaction, standing to obtain two layered liquids, separating to obtain ionic liquid [ Cat]+[A]‑(ii) a The layering reagent is selected from at least one of sugar, sugar alcohol or amino acid. The method relates to the use of a layering reagent, realizes a more universal new method for synthesizing the ionic liquid, does not require an inorganic salt reactant to have high water solubility, avoids using organic solvents or harmful substances such as silver salts and the like in the traditional method, is very environment-friendly, and can repeatedly use the layering reagent; the prepared ionic liquid [ Cat]+[A]‑The purity of (A) is more than 98%.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a method for synthesizing ionic liquid by using aqueous two phases.
Background
Ionic liquids (or ionic liquids) refer to liquids that are composed entirely of ions. Organic ionic liquids (Organic ionic liquids) are a class of Organic molten salts that are composed of Organic cations and inorganic or Organic anions and that are liquid at or near room temperature. The volume of the ions forming the ionic liquid is large, and the charges are fully delocalized and dispersed on the anions and the cations by the conjugate effect, so that the electrostatic acting force between the anions and the cations is weakened; the volume difference between the anions and cations is large and extremely asymmetric, and the orderliness of the whole system is reduced, so that the ionic compound can be in a liquid state at room temperature. Based on the environmentally friendly properties of ionic liquids, unique microscopic ionic environment and solubility, and rich designability, ionic liquid research has undergone a development from the first generation to the third generation, and its applications have also progressed from the first simple solvents and electrolytes (first generation ionic liquids), to the latter soft functional materials (second generation ionic liquids), and more recently, bioactive substances (third generation ionic liquids).
So far, most of the research on ionic liquids is still in the laboratory exploration stage, and the ionic liquids are not put into practical use on a large scale. This is not only because of their high price, but also because ionic liquids are not as "environmentally friendly" as one would expect. Ionic liquids, like most chemicals, are more or less toxic. Toxicity generally increases with increasing hydrophobicity because hydrophobic, especially long side chain-containing ionic liquids, readily interact with phospholipid molecules in cell membranes, disrupting the membrane bilayer structure. In addition, the preparation process of the ionic liquid is not 'green and environment-friendly', is often accompanied by the use of organic solvents, noble metal silver salts or toxic substances, and has the disadvantages of complex process, long time consumption and high cost.
In the prior art, the synthesis of the ionic liquid mainly comprises a one-step method and a two-step method. The one-step process generally employs an alkylating agent (such as dialkyl sulfate, etc.) to directly perform a quaternization reaction with a lewis basic organic substance to form the target product. The method has simple process, high reaction rate and high yield. But subject to alkylationThe one-step method is only suitable for synthesizing some specific ionic liquids. And the (electro) chemical stability of the anions is not high, the anions have strong coordination or electron donating capability, and the ionic liquid formed by the anions is not a good inert solvent or electrolyte. In contrast, the two-step method has higher applicability and flexibility, is a method generally adopted at present, and is particularly suitable for preparing the functionalized ionic liquid by 'cutting design'. The two-step process mainly comprises two steps of quaternization and anion exchange, wherein the anion exchange is the focus and difficulty of research. First, a haloalkane (R [ X ]]R represents an alkyl group, [ X ]]Representing a halogen atom) with a basic organic substance to produce an organic cationic halide ([ Cat)]+[X]-，[Cat]+Representing an organic cation). Since the obtained product is an ionic compound, the ionic compound can be separated from the molecular reactant and the solvent by recrystallization, washing and the like, and purified. Secondly, by means of an anion exchange reaction, i.e. [ Cat ]]+[X]-+[M]+[A]-Generation of [ Cat]+[A]-+[M]+[X]-Will [ Cat ]]+[X]-Halogen anion of [ X ]]-Replacement by the target anion [ A ]]-And obtaining [ Cat ]]+[A]-Ionic liquid product. Since the reactants and the product in the anion exchange reaction are ionic compounds containing at least four ions, their existing forms in the solution are very complicated, including individual ions, solvated ions, ion pairs of mutually matched anions and cations, and ion clusters of various types, etc., it is difficult to directly separate the product from the complicated reaction system, or the product is often a mixture in which a large amount of reactant ions ([ M ] may remain]+、[X]-)。
Therefore, the research on an efficient ion exchange method, particularly a technology for effectively separating and obtaining a pure ionic liquid product from a complex reaction system, is the key for improving the environmental friendliness of the ionic liquid, reducing the cost and promoting the large-scale production and application.
In the earlier stage research of ionic liquid synthesis, excessive inorganic salt reactant is added, and the salting-out effect is generated by utilizing the high water solubility of the inorganic salt reactant, so that the liquid/liquid phase separation of the ionic liquid product and a water phase reaction medium is realized, and a green ionic liquid synthesis method is invented on the basis of the salting-out effect, and an issued patent is applied: CN 105481773B. However, this method requires a high water solubility of the inorganic salt reactant to ensure a sufficient salting-out effect to achieve phase separation of the product from the aqueous reaction medium, and therefore, has certain substrate limitations. For example, patent CN105481773B must use potassium acetate (233g/100mL @20 ℃, namely 233g of potassium acetate can be dissolved in 100mL at 20 ℃) with extremely high water solubility so as to ensure enough salting-out effect and realize liquid/liquid separation to synthesize the acetate ionic liquid. Such synthetic methods have significant limitations.
Therefore, it is desirable to provide a novel method for synthesizing ionic liquid by aqueous two-phase method, which does not require high solubility for the water solubility of inorganic salts involved in the reaction process, and which can synthesize more types of ionic liquids with universality.
Disclosure of Invention
The present invention is directed to solving at least one of the problems of the prior art described above. Therefore, the invention provides a method for synthesizing ionic liquid by using aqueous two phases, which relates to the use of a layering reagent, realizes a more universal new method for synthesizing the ionic liquid, and does not require an inorganic salt reactant to have high water solubility. For example, in the synthesis of acetate ionic liquid, the patent CN105481773B must use potassium acetate (233g/100mL @20 ℃) with extremely high water solubility so as to ensure enough salting-out effect and realize liquid/liquid layering; in contrast, the present invention can utilize less water soluble inorganic salts (e.g., sodium acetate 46.4/100mL @20 deg.C., lithium acetate 40.8/100mL @20 deg.C.) as the inorganic salt reactant due to the addition of the layering agent. In addition, the method used in this project can also be used to synthesize products that could not be synthesized by the method of the CN105481773B patent, for example, by [ CH ]3SO3]-、[BOB]-(Bisbioxaoxoborate), [ DFOB ]]-(difluoro oxalato borate) and the like are anionic ionic liquids.
The invention provides a method for synthesizing ionic liquid by aqueous two phases, which realizes green and efficient synthesis of the ionic liquid, and promotes ionic liquid products and reaction media to form liquid/liquid layered aqueous two phases by adding a recyclable layered reagent (a non-ionic layered reagent), so that the ionic liquid is simply and efficiently prepared, and harmful substances such as organic solvents or silver salts and the like in the traditional method are avoided.
The application of a layering reagent in the preparation of ionic liquid;
the layering reagent is selected from at least one of sugar, sugar alcohol or amino acid.
A method for synthesizing ionic liquid by aqueous two-phase synthesis comprises the following steps:
cationic precursor [ Cat ]]+[X]-And an anionic precursor [ M]+[A]-(anion precursor [ M)]+[A]-Also called inorganic salt reactant) is dissolved in water, then a layering reagent is added, stirred for reaction and kept stand to obtain two layered liquids, and the two layered liquids are separated to prepare the ionic liquid [ Cat]+[A]-(ii) a Said [ Cat]+、[M]+Represent different cations; said [ X ]]-、[A]-Represent different anions.
Preferably, the layering reagent is selected from at least one of monosaccharides, disaccharides, sugar alcohols or amino acids.
Preferably, the layering reagent is selected from at least one of ribose, xylose, arabinose, glucose, mannose, galactose, rhamnose, fructose, sucrose, maltose, lactose, wintergreen sugar, fava sugar, sophorose, rutinose, neoorange sugar, xylitol, lactitol, sorbitol, mannitol, maltitol, erythritol, glycine, alanine, valine, leucine, isoleucine, methionine, proline, tryptophan, serine, tyrosine, cysteine, phenylalanine, asparagine, glutamine, threonine, aspartic acid, glutamic acid, lysine, arginine, or histidine.
Preferably, the ionic liquid [ Cat]+[A]-The structural formula of (A) is as follows:
r in formula (I)1、R2、R3、R4Are independently H, -CnH2n+1、-CnH2nOCmH2m+1、-CnH2nCO2CmH2m+1or-CnH2nOne of CN; wherein n is any integer between 1 and 20; m is any integer between 0 and 10; x is any integer between 1 and 5; a. the-Is [ BF ]4]-、[PF6]-、[SbF6]-、[CN]-、[SCN]-、[NO3]-、[ClO4]-、[MnO4]-、[HCO2]-、[CH3CO2]-、[CF3CO2]-，[CH3SO3]-、[C2H5SO3]-、[CH3OSO3]-、[C2H5OSO3]-、[CF3SO3]-、[C2F5SO3]-、[CF3OSO3]-、[C2F5OSO3]-、[N(CN)2]-、[C(CN)3]-、[B(CN)4]-、[(FSO2)2N]-、[(CF3CO)2N]-、[(CF3SO2)2N]-、[BOB]-(bis oxalato borate) or [ DFOB]-(difluoro oxalic acid borate).
Further preferably, n is any integer between 1 and 10, and m is any integer between 0 and 10.
Preferably, said [ Cat]+[X]-In (1) [ X ]]-Is selected from [ F]-、[Cl]-、[Br]-Or [ I]-At least one of; further preferably, [ X ] is]-Is selected from [ Cl]-、[Br]-Or [ I]-At least one of (1).
Preferably, said [ M ]]+[A]-In [ M ]]+Is [ H ]]+、[Li]+、[Na]+、[K]+Or [ NH ]4]+At least one of (1).
Preferably, the cationic precursor [ Cat+][X-]And an anionic precursor [ M+][A-]The molar ratio of (1) to (2.5-0.5); further preferably, the cationic precursor [ Cat+][X-]And an anionic precursor [ M+][A-]The molar ratio of (1) to (2).
Preferably, the water is deionized water.
Preferably, the layering reagent is reacted with an anionic precursor [ M ]+][A-]In a molar ratio of 1: (0.3-5); further preferred, the layering reagent is combined with an anionic precursor [ M ]+][A-]In a molar ratio of 1: (0.8-2.5).
Preferably, the layering reagent is added in an amount such that liquid/liquid layering occurs (one layer is [ Cat ])]+[A]-The enriched layer and the other layer comprise a layering reagent, water, [ M ]]+、[X]-Mixture of) and an ionic liquid rich layer (i.e., [ Cat ]]+[A]-Concentrated layer) no longer changes volume.
Preferably, the stirring time is 0.5 to 2 hours. The effect of the thorough stirring is to allow the reaction to proceed sufficiently.
Preferably, after completion of the reaction, the reaction mixture is allowed to stand, and not only liquid/liquid separation (one layer is [ Cat ]]+[A]-The enriched layer and the other layer comprise a layering reagent, water, [ M ]]+、[X]-Mixtures of (b) and by-products [ M ] may also occur]+[X]-And (4) precipitating. By-product [ M]+[X]-For the precipitate [ M]+[X]-Washing with saturated water solution for 2-3 times to obtain byproduct [ M ] with purity of more than 98%]+[X]-。
Preferably, not only the ionic liquid [ Cat ] is obtained after the liquid separation]+[A]-And further obtaining a mixture containing a layering reagent, water and [ M ]]+[X]-The solution of (1). The resulting solution containing the layering reagent, water and [ M ]]+[X]-The solution of (2) can be reused.
Preferably, after the ionic liquid is prepared, the method further comprises the following steps: washing the resulting ionic liquid [ Cat ] with an aqueous solution of a layering reagent]+[A]-Then drying, standing and filtering to obtain filtrate, thus obtaining the purified ionic liquid. The purified ionic liquid [ Cat]+[A]-The purity of (A) is more than 98%.
Preferably, the number of washes is 2 to 5.
Preferably, the aqueous solution of the layering reagent is mixed with the ionic liquid [ Cat ] in the washing process]+[A]-The volume ratio of (1) to (0.1): 1; further preferably, an aqueous solution of a layering reagent is mixed with an ionic liquid [ Cat ]]+[A]-The volume ratio of (0.1-5): 1. the purpose of the washing is to remove residual anionic precursor [ M ] from the ionic liquid solution]+[A]-. And collecting the washing liquid for later use.
Preferably, during the washing, the aqueous solution of the layering reagent is a saturated aqueous solution of the layering reagent.
An ionic liquid prepared by the method of the invention has a purity of greater than 98%.
The addition of the layering reagent does not cause additional reaction, and particularly does not cause ion cross contamination; the layering reagent of the invention has high water solubility to ensure enough layering capacity and realize liquid/liquid phase separation of products and reaction media; the miscibility between the layering reagent and the ionic liquid product should be as low as possible to reduce the residue of the layering reagent in the product, simplify subsequent purification steps, and improve product purity.
The ionic liquid synthesized by the invention is prepared by1The purity can be maintained above 98% by analyzing the structure and purity by technical means such as H-NMR nuclear magnetism, ion chromatography, and other chemical analysis methods (such as an indantrione method and an anthrone sulfate method).
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention provides a method for synthesizing ionic liquid by two aqueous phases, which relates to the use of a layering reagent, realizes a more universal new method for synthesizing the ionic liquid, does not require an inorganic salt reactant to have high water solubility, avoids using organic solvents or harmful substances such as silver salts and the like in the traditional method, is very environment-friendly, and can be repeatedly used. The prepared ionic liquid [ Cat]+[A]-The purity of (A) is more than 98%.
(2) The method is essentially a liquid/liquid two-phase reaction, and is characterized by fast mass transfer, short reaction time, simple equipment, convenient operation, easy large-scale production, recyclable layering reagent, environmental protection, high efficiency and contribution to greatly reducing the synthesis cost.
Detailed Description
In order to make the technical solutions of the present invention more apparent to those skilled in the art, the following examples are given for illustration. It should be noted that the following examples are not intended to limit the scope of the claimed invention.
The starting materials, reagents or apparatuses used in the following examples are conventionally commercially available or can be obtained by conventionally known methods, unless otherwise specified.
Example 1: 1-butyl-3-methylimidazolium acetate ionic liquid [ BMIm]+[CH3CO2]-Preparation of
A method for synthesizing ionic liquid by aqueous two-phase synthesis comprises the following steps:
0.10mol of cationic precursor [ BMIm ] was added at 25 deg.C]+[Cl]-And 0.12mol of an anion precursor [ Na ]]+[CH3CO2]-Dissolving in 10mL of water, mixing, adding 0.123mol (18 g) of layering reagent lysine (1 g of lysine is added in batches, layering occurs after the addition amount of the lysine reaches 6g, the addition amount reaches 18g, the volume of an ionic liquid enrichment layer does not change), stirring for reacting for 30 minutes, standing after the reaction is finished, and obtaining a solutionLiquid separation (upper layer is [ BMIm ]]+[CH3CO2]-The ionic liquid, the lower layer is layered reagent lysine, water, [ Na ]]+、[Cl]-Mixtures of (a) and also by-products [ Na ] are present]+[Cl]-Separating the precipitate to obtain ionic liquid [ BMIm]+[CH3CO2]-(ii) a The ionic liquid [ BMIm ] was washed with an aqueous solution of lysine (2.0mL of water +7.0g of lysine)]+[CH3CO2]-2 times, the washed ionic liquid [ BMIm ]]+[CH3CO2]-Vacuum drying at 60 deg.C and 0.1Pa for 10 hr, standing, and filtering to obtain 11.5g colorless ionic liquid [ BMIm]+[CH3CO2]-The yield was 58%.
The above by-product [ Na ]]+[Cl]-Washing the precipitate with 20mL saturated NaCl solution at 80 deg.C under 0.1Pa for 3 times, and drying the solid in a vacuum oven at 80 deg.C for 10 hr to obtain 3.5g white solid NaCl and byproduct [ Na ]]+[Cl]-The recovery of (a) was 60%.
The preparation process includes separating agent lysine, water and Na]+、[Cl]-The mixture(s) can be reused to wash the ionic liquid [ BMIm]+[CH3CO2]-The resulting wash solution can also be reused.
Example 2: 1-butyl-3-methylimidazolium bisoxalato borate ionic liquid [ BMIm]+[BOB]-Preparation of
A method for synthesizing ionic liquid by aqueous two-phase synthesis comprises the following steps:
0.10mol of cationic precursor [ BMIm ] was added at 25 deg.C]+[Cl]-And 0.12mol of the anion precursor lithium bis (oxalato) borate [ Li []+[BOB]-Dissolving in 10mL of water, mixing, adding 0.056mol (10 g) of layered reagent glucose (1 g of glucose is added in batches, when the addition amount of glucose reaches 4g, layering occurs, the addition amount reaches 10g, the volume of the ionic liquid enrichment layer does not change any more), stirring and reacting for 30 minutes, and reactingAfter completion, the mixture was allowed to stand still for liquid/liquid separation (upper layer, [ BMIm ]]+[BOB]-The ionic liquid, the lower layer is layered reagent glucose, water, [ Li ]]+、[Cl]-Mixtures of (ii) and also by-products [ Li ] appear]+[Cl]-Separating the precipitate to obtain ionic liquid [ BMIm]+[BOB]-(ii) a The ionic liquid [ BMIm ] was washed again with an aqueous solution of glucose (2.0mL of water +3.0g of lysine)]+[BOB]-2 times, the washed ionic liquid [ BMIm ]]+[BOB]-Vacuum drying at 60 deg.C and 0.1Pa for 10 hr, standing, and filtering to obtain 19.6g colorless ionic liquid [ BMIm]+[BOB]-The yield was 60%.
The above by-product [ Li]+[Cl]-Washing the precipitate with newly prepared LiCl saturated water solution 3 times, each time in an amount of 20mL, drying the obtained solid in a vacuum oven at 80 deg.C and 0.1Pa for 10 hr to obtain 0.8g white solid LiCl, and byproduct [ Li]+[Cl]-The recovery of (A) was 19%.
The preparation process includes the steps of preparing glucose, water and Li]+、[Cl]-The mixture(s) can be reused to wash the ionic liquid [ BMIm]+[BOB]-The resulting wash solution can also be reused.
Product effectiveness testing
The ionic liquid [ BMIm ] obtained in example 1-2 was used]+[CH3CO2]-And [ BMIm]+[BOB]-The results of the structural and purity analyses are shown in Table 1.
Table 1:
as can be seen from Table 1, the ionic liquids obtained in examples 1-2 of the present invention had a purity of over 98%.
Claims (5)
1. A method for synthesizing ionic liquid by aqueous two phases is characterized by comprising the following steps:
cationic precursor [ Cat ]]+[X]-And an anionic precursor [ M]+[A]-Dissolving in water, adding layering reagent, stirring for reaction, standing to obtain two layered liquids, separating to obtain ionic liquid [ Cat]+[A]-(ii) a The addition amount of the layering reagent is that liquid/liquid layering phenomenon occurs, wherein one layer is [ Cat]+[A]-Enriching layer, another layer is layer separating reagent, water, [ M ]]+[X]-And the ionic liquid-rich layer is [ Cat ]]+[A]+Until the volume of the enrichment layer is not changed any more;
said [ Cat]+、[M]+Represent different cations; said [ X ]]-、[A]-Represent different anions;
said [ A ]]-Is [ HCO ]2]-、[CH3CO2]-、[CF3CO2]-、[BOB]-Or [ DFOB ]]-One of (1);
said [ X ]]-Is selected from [ F]-、[Cl]-、[Br]-Or [ I]-At least one of;
said [ M ]]+Is [ Li ]]+、[Na]+At least one of; the layering reagent is selected from at least one of ribose, xylose, arabinose, glucose, mannose, galactose, rhamnose, fudge, fructose and lysine;
the ionic liquid [ Cat] +[A]-The structural formula of (A) is as follows:
r in the formula (1)1、R2、R3Are independently H, -CnH2n+1One of (1); wherein n is any integer between 1 and 20.
2. The method of claim 1Method, characterized in that the cationic precursor [ Cat ]]+ [X]-And an anionic precursor [ M]+ [A]-The molar ratio of (1) to (2.5-0.5).
3. The method of claim 1, wherein the layering reagent is reacted with an anionic precursor [ M ]]+ [A]-In a molar ratio of 1: (0.3-5).
4. The process according to claim 1, characterized in that an ionic liquid [ Cat ] is produced]+[A]-Then, the method also comprises the following steps: washing the resulting ionic liquid [ Cat ] with an aqueous solution of the layering reagent]+[A]-Then drying, standing and filtering the solution to obtain filtrate and obtain purified ionic liquid [ Cat]+[A]-。
5. The application of a layering reagent in the preparation of ionic liquid;
the layering reagent is selected from at least one of ribose, xylose, arabinose, glucose, mannose, galactose, rhamnose, fudge, fructose and lysine;
an ionic liquid prepared by the process of any one of claims 1 to 4.
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| CN101664612B (en) * | 2009-09-29 | 2011-07-27 | 东华大学 | Method for purifying and separating ionic liquid from water |
| CN102544636A (en) * | 2012-01-06 | 2012-07-04 | 中国科学院过程工程研究所 | Alkaline ion liquid electrolyte for zinc-air battery |
| CN105481773B (en) * | 2015-12-18 | 2019-03-26 | 贵州师范学院 | A kind of new method preparing ionic liquid |
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