CN101341872A - Ion liquid anti-virus activities bactericide, synthesis and application thereof - Google Patents
Ion liquid anti-virus activities bactericide, synthesis and application thereof Download PDFInfo
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- CN101341872A CN101341872A CNA2008100716336A CN200810071633A CN101341872A CN 101341872 A CN101341872 A CN 101341872A CN A2008100716336 A CNA2008100716336 A CN A2008100716336A CN 200810071633 A CN200810071633 A CN 200810071633A CN 101341872 A CN101341872 A CN 101341872A
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- ion liquid
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- quaternary ammonium
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Abstract
The invention relates to ionic liquid bactericidal and bacteriostatic agent, and a synthetic method and the application thereof; the invention relates to ionic liquid bactericidal and bacteriostatic agent, and a synthetic method and the application thereof, in particular to a trans-butene diacid monoester anion base ionic liquid bactericidal and bacteriostatic agent and a synthetic method thereof, and the application of the trans-butene diacid monoester anion base ionic liquid bactericidal and bacteriostatic agent and the synthetic method in preparing bactericidal and bacteriostatic medicine. The invention provides novel series compound ionic liquid bactericidal and bacteriostatic agent, and a synthetic method and the application thereof. First, trans-butene diacid monoester is synthesized, and then alkyl methyl imidazole quaternary ammonium hydroxide is synthesized, and finally the ionic liquid bactericidal and bacteriostatic agent is synthesized. The ionic liquid bactericidal and bacteriostatic agent has very strong activity of bactericidal and bacteriostatic agent, and can be used to prepare anti-bacterial medicine. The synthesis route is short, the synthesis process is simple, the raw material cost is low, the environment pollution is small, the requirements for production equipment and environment conditions are not high, and the purity of the synthesized products is high, the yield is high, and the storage, transportation, packaging and use are convenient; therefore, the ionic liquid bactericidal and bacteriostatic agent is very applicable to large-scale industrialized production.
Description
Technical field
The present invention relates to a class ion liquid anti-virus activities bactericide and synthetic method and application, especially relate to a class fumaric acid monoesters anion base ion liquid anti-virus activities bactericide and a synthetic method thereof, and their application in preparation restraining and sterilizing bacteria medicine.
Background technology
The solvability of bacteriostatic agent in You Heshui directly influences its fungistatic effect.This is because microorganism only is present in aqueous phase, so in fact the bacteriostatic agent that enters in the oil phase is loss.Therefore, the design principle of new bacteriostatic agent is to design the little and water-soluble big bacteriostatic agent of oil-soluble.The fumarate class is a widely used class bacteriostatic agent, and their characteristics are that fungicidal spectrum is wide, low to other bio-toxicity, Environmental compatibility good, but its poorly water-soluble in use is prone to layering, greatly influences its result of use.The quaternary ammonium salt bacteriostatic agent is water-soluble and bacteriostatic activity is better, and the bacteriostasis of this class bacteriostatic agent with the universal law of quaternary ammonium salt structural change is: along with the growth of alkyl chain, bacteriostasis strengthens; But to certain-length, antibacterial power descends on the contrary.Do not see as yet so far and introduce the report of ester group and imidazoles quaternary ammonium in the beta-unsaturated carbonyl precursor structure simultaneously at efficient antibacterial α.The present invention is raw material with the maleic anhydride, synthetic fumaric acid monoesters, adopt the mixing together method again, itself and quaternary ammonium base are reacted the synthetic efficient antibacterial α that has, the novel ion liquid anti-virus activities bactericide of beta-unsaturated carbonyl precursor structure and good water solubility, effectively solve the phenomenon of profit layering, strengthen the result of use of fumarate class.(referring to document: [1] N.Bodor, J.J.Kaminski, S.Selk.Soft Drugs.1.Labile Quaternary Ammonium Salts as Soft Antimicrobials.J.Med.Chem.1980,23 (5): 469-474; [2] G.N.Ou, M.X.Zhu, J.R.She, Y.Z.Yuan.Ionic liquid buffers:a newclass of chemicals with potential for controlling pH in non-aqueous media.Chem.Commun.2006, (44): 4626-4628; [3] J.Pernak, I.Goc, I.Mirska.Anti-microbial activities of protic ionic liquidswith lactate anion.Green Chem.2004, (6): 323-329)
In view of ion liquid anti-virus activities bactericide has good prospects for application, adopt the preparation method that synthetic route is short, synthesis technique is simple, cost of material is low, environmental pollution is little, make and accomplish scale production, have realistic meaning.
Summary of the invention
One of purpose of the present invention provides a kind of new series compound ion liquid anti-virus activities bactericide and synthetic method and application.
The general formula of new series compound ion liquid anti-virus activities bactericide [RMIM] [MEF] of the present invention is:
In the general formula, R
1Be alkyl, R
2Be alkyl or any phenyl that replaces.
Alkyl can be the straight or branched alkyl with 1～8 carbon, can be selected from a kind of in methyl, ethyl, propyl group, isopropyl, butyl, the octyl group etc.Arbitrarily the phenyl that replaces can be selected from a kind of in aminomethyl phenyl, ethylphenyl, propyl group phenyl, the halogenophenyl etc.
The synthetic route of ion liquid anti-virus activities bactericide of the present invention [RMIM] [MEF] is:
Reflux is for refluxing in the formula, and Ionic exchange is an ion exchange process; R
1Be alkyl, R
2Be alkyl or any phenyl that replaces.
The synthetic method of ion liquid anti-virus activities bactericide of the present invention may further comprise the steps:
1) fumaric acid monoesters (MEF) is synthetic
Maleic anhydride and alcohol are added thermal response, add anhydrous AlCl again
3Isomery agent and petroleum ether and stirring reflux, and filter, and filtrate boils off solvent and obtains thick product, and thick product adds NaOH solution or Na
2CO
3Solution or NaHCO
3Petroleum ether extraction is used in the solution dissolving, and water is regulated pH=3.5～4.5 with hydrochloric acid, divides the phase of anhydrating, washing, and drying promptly gets the pure product of fumaric acid monoesters (MEF);
2) alkyl methylimidazole quaternary ammonium base ([RMIM] OH) is synthetic
With N-methylimidazole and the reaction of alkyl chloride heated and stirred, tell upper strata unreacting material liquid after the reaction, obtain the thick product of chlorinated hydrocabon ylmethyl imidazoles quaternary ammonium salt ([RMIM] Cl), again through ethyl acetate wash the pure product of [RMIM] Cl, preparation [RMIM] Cl aqueous solution, cross anion-exchange column, get alkyl methylimidazole quaternary ammonium base [RMIM] the OH aqueous solution;
3) [RMIM] [MEF's] is synthetic
Fumaric acid monoesters (MEF) joined in alkyl methyl quaternary ammonium base [RMIM] the OH aqueous solution react, moisture is removed in evaporation, obtains ion liquid anti-virus activities bactericide [RMIM] [MEF].
In step 1), described alcohol preferably passes through dehydration processing, adds thermal response and is preferably under the air-proof condition and carries out; In molar ratio, best maleic anhydride: alcohol=(1.0～1.1): 1, reaction temperature and reaction time are looked raw materials used different the and variation to some extent of kind, reaction temperature can be controlled under the reflux temperature of alcohol, reaction temperature can be 60～90 ℃, and the reaction time can be 0.5～2h, adds anhydrous AlCl again
3The time that isomery agent and petroleum ether and stirring reflux can be 1～2h, and thick product can add excessive 1～2molL
-1The dissolving of NaOH solution; The concentration that NaOH solution is preferably in molar ratio is 1～2mol L
-1, Na
2CO
3Solution and NaHCO
3Solution is preferably saturated solution.
In step 2) in, N-methylimidazole and alkyl chloride are preferably handled through dehydration, decolouring; The most handy anhydrous ethyl acetate of ethyl acetate, the anion exchange degree can be demarcated OH by the HCl standard liquid
-And AgNO
3Standard liquid is demarcated Cl
-In molar ratio, best N-methylimidazole: alkyl chloride=1: (1.2～1.5), the heated and stirred reaction is preferably in heated and stirred reaction under the air-proof condition, it is different and change to some extent that reaction temperature and reaction time are looked raw materials used kind, reaction temperature can be controlled under the reflux temperature of alkyl chloride, reaction time can be 6～20h, and by mass percentage, the concentration of [RMIM] Cl aqueous solution is 70～80%.
In step 3), the concentration of alkyl methyl quaternary ammonium base [RMIM] the OH aqueous solution can determine that the pH of solution is adjusted to 7～8 with the method for demarcating NaOH solution; In molar ratio, fumaric acid monoesters (MEF): alkyl methyl quaternary ammonium base [RMIM] the OH aqueous solution=1: 1.
Detect through experiment, ion liquid anti-virus activities bactericide of the present invention [RMIM] [MEF] has very strong bacteriostatic activity, can be used for preparing antibacterials.
Ion liquid anti-virus activities bactericide [RMIM] [MEF] to colibacillary minimum inhibitory concentration (MIC) below 0.04g/L, to staphylococcus aureus and bacillus subtilis MIC below 0.06g/L, and to the MIC of white Candida and saccharomyces cerevisiae below 0.8g/L.MIC represents not have the sample concentration of the minimum of experimental bacteria growth.Because ion liquid anti-virus activities bactericide [RMIM] [MEF] has very strong bacteriostatic activity, therefore they can be applied to prepare the restraining and sterilizing bacteria medicine.
Compare with existing anti-virus activities bactericide,, therefore can be used for preparing antibacterials because ion liquid anti-virus activities bactericide of the present invention [RMIM] [MEF] has very strong anti-virus activities bactericide activity.Because the synthetic route of the synthetic method of ion liquid anti-virus activities bactericide of the present invention is short, synthesis technique is simple, cost of material is low, environmental pollution is little, less demanding to production equipment and environmental condition, and the product purity height that is synthesized, the productive rate height, be convenient to store, transport, pack and use, therefore be fit to very much large-scale industrial production.
Embodiment
The invention will be further described below in conjunction with specific embodiment.
Embodiment 1
Synthesizing of single-ethyl fumarate Ji Xinji methylimidazole ion liquid anti-virus activities bactericide ([OMIM] [MEF])
1) single-ethyl fumarate (MEF) is synthetic
Add the ethanol (0.05mol) after 4.93g maleic anhydride (0.055mol) and 2.88mL handle through anhydrous sodium sulfate in round-bottomed flask, the oil bath heated and stirred at 80 ℃ of reaction 1h, adds anhydrous AlCl again
380 ℃ of backflow 2h of isomery agent and benzinum.Filter, filtrate boils off solvent and obtains thick product.Thick product adds 26mL 2mol L
-1Petroleum ether extraction is used in the dissolving of NaOH solution, and water is regulated pH=4 with hydrochloric acid, divides the phase of anhydrating, washing, and drying promptly gets the pure product of MEF.
2) octyl group methylimidazole quaternary ammonium base [OMIM] OH's is synthetic
Got N-methylimidazole after the decompression distillation and chloro normal octane 1: 1.2 in molar ratio, and added successively in the 250ml single port flask, reaction system is 80 ℃ of heated and stirred reactions under air-proof condition.Reaction obtains chlorination octyl group methylimidazole quaternary ammonium salt ([OMIM] Cl) behind the 12h, tells upper strata unreacting material liquid, the thick product of [OMIM] Cl add ethyl acetate wash the pure product of [OMIM] Cl.Preparation 70%[OMIM] the Cl aqueous solution, cross anion-exchange column, get octyl group methylimidazole quaternary ammonium base [OMIM] the OH aqueous solution.
3) [OMIM] [MEF's] is synthetic
Quantitative single-ethyl fumarate (MEF) is joined (in molar ratio, being 1: 1) in octyl group methyl quaternary ammonium base [OMIM] the OH aqueous solution, neutralization reaction.Rotary evaporation is removed moisture, obtains ion liquid anti-virus activities bactericide [OMIM] [MEF].
Embodiment 2
Synthesizing of fumaric acid mono octyl ester Ji Xinji methylimidazole ion liquid anti-virus activities bactericide ([OMIM] [MOF])
1) fumaric acid mono octyl ester (MOF) is synthetic
In round-bottomed flask, add the 0.055mol maleic anhydride, the 0.05mol n-octyl alcohol, the oil bath heated and stirred is reacted 45min under 60 ℃ of conditions, adds anhydrous AlCl again
380 ℃ of backflow 2h of isomery agent and benzinum.Filter, filtrate boils off solvent and obtains thick product.Thick product adds 26mL 2mol L
-1Petroleum ether extraction is used in the dissolving of NaOH solution, and water is regulated pH=4 with hydrochloric acid, divides the phase of anhydrating, washing, and drying promptly gets the pure product of MOF.
2) octyl group methylimidazole quaternary ammonium base [OMIM] OH's is synthetic
N-methylimidazole and the chloro normal octane got after the decompression distillation add in the 250ml single port flask than successively with 1: 1.2 (in molar ratio), and reaction system is 80 ℃ of heated and stirred reactions under air-proof condition.Reaction obtains chlorination octyl group methylimidazole quaternary ammonium salt ([OMIM] Cl) behind the 12h, tells upper strata unreacting material liquid, the thick product of [OMIM] Cl add ethyl acetate wash the pure product of [OMIM] Cl.Preparation 70%[OMIM] the Cl aqueous solution, cross anion-exchange column, get octyl group methylimidazole quaternary ammonium base [OMIM] the OH aqueous solution.
3) [OMIM] [MOF's] is synthetic
Quantitative fumaric acid monoesters (MOF) is joined (being 1: 1 in molar ratio) in octyl group methyl quaternary ammonium base [OMIM] the OH aqueous solution, neutralization reaction.Rotary evaporation is removed moisture, obtains ion liquid anti-virus activities bactericide [OMIM] [MOF].
Embodiment 3
Synthesizing of fumaric acid list phenethyl ester Ji Xinji methylimidazole ion liquid anti-virus activities bactericide ([OMIM] [MBF])
1) fumaric acid list phenethyl ester (MBF) is synthetic
In round-bottomed flask, add the 4.93g maleic anhydride, the benzyl carbinol of 6.00mL, the oil bath heated and stirred is reacted 30min under 60 ℃ of conditions, adds anhydrous AlCl again
380 ℃ of backflow 2h of isomery agent and benzinum.Filter, filtrate boils off solvent and obtains thick product.Thick product adds 26mL 2mol L
-1Petroleum ether extraction is used in the dissolving of NaOH solution, and water is regulated pH=4 with hydrochloric acid, divides the phase of anhydrating, washing, and drying promptly gets the pure product of MBF.
2) octyl group methylimidazole quaternary ammonium base [OMIM] OH's is synthetic
N-methylimidazole and the chloro normal octane got after the decompression distillation add in the 250ml single port flask successively with 1: 1.2 (in molar ratio), and reaction system is 80 ℃ of heated and stirred reactions under air-proof condition.Reaction obtains chlorination octyl group methylimidazole quaternary ammonium salt ([OMIM] Cl) behind the 12h, tells upper strata unreacting material liquid, the thick product of [OMIM] Cl add ethyl acetate wash the pure product of [OMIM] Cl.Preparation 70%[OMIM] the Cl aqueous solution, cross anion-exchange column, get octyl group methylimidazole quaternary ammonium base [OMIM] the OH aqueous solution.
3) [OMIM] [MBF's] is synthetic
Quantitative fumaric acid monoesters (MBF) is joined (being 1: 1 in molar ratio) in quaternary ammonium base [OMIM] the OH aqueous solution, neutralization reaction.Rotary evaporation is removed moisture, obtains ion liquid anti-virus activities bactericide [OMIM] [MBF].
Embodiment 4
Synthesizing of fumaric acid list phenylpropyl alcohol ester group octyl group methylimidazole ion liquid anti-virus activities bactericide ([OMIM] [MPF])
1) fumaric acid list phenylpropyl alcohol ester (MPF) is synthetic
In round-bottomed flask, add the 0.055mol maleic anhydride, the 0.05mol phenylpropanol, the oil bath heated and stirred is reacted 45min under 60 ℃ of conditions, adds anhydrous AlCl again
380 ℃ of backflow 2h of isomery agent and benzinum.Filter, filtrate boils off solvent and obtains thick product.Thick product adds 26mL 2mol L
-1Petroleum ether extraction is used in the dissolving of NaOH solution, and water is regulated pH=4 with hydrochloric acid, divides the phase of anhydrating, washing, and drying promptly gets the pure product of MPF.
2) octyl group methylimidazole quaternary ammonium base [OMIM] OH's is synthetic
N-methylimidazole and the chloro normal octane got after the decompression distillation add in the 250ml single port flask than successively with 1: 1.2 (in molar ratio), and reaction system is 80 ℃ of heated and stirred reactions under air-proof condition.Reaction obtains chlorination octyl group methylimidazole quaternary ammonium salt ([OMIM] Cl) behind the 12h, tells upper strata unreacting material liquid, the thick product of [OMIM] Cl add ethyl acetate wash the pure product of [OMIM] Cl.Preparation 70%[OMIM] the Cl aqueous solution, cross anion-exchange column, get octyl group methylimidazole quaternary ammonium base [OMIM] the OH aqueous solution.
3) [OMIM] [MPF's] is synthetic
Quantitative fumaric acid monoesters (MPF) is joined (being 1: 1 in molar ratio) in octyl group methyl quaternary ammonium base [OMIM] the OH aqueous solution, neutralization reaction.Rotary evaporation is removed moisture, obtains ion liquid anti-virus activities bactericide [OMIM] [MPF].
Embodiment 5
Adopting micro-doubling dilution that ion liquid anti-virus activities bactericide is carried out bacteriostatic activity detects.
With sterile water the indicator bacteria of cultivating on the inclined-plane is washed, making thalline or spore concentration is 10
7The bacterium liquid of CFU/mL, 4 ℃ of preservations are standby.During use, (the bacterium final concentration is about 10 with an amount of medium mixing
5CFU/mL, the fungi final concentration is about 10
4CFU/mL).Testing sample is dissolved in the water, is mixed with certain density solution, sample is added in the 96 porocyte plates, adopt micro-doubling dilution dilute sample.Do not add the negative contrast that testing sample only contains indicator bacteria; The blank that is that only contains medium; The positive control indicator bacteria is used ampicillin during for bacterium, and indicator bacteria is used amphotericin B during for fungi.Bacterium is cultivated 24h for 37 ℃, and fungi is cultivated 48h for 25 ℃, and perusal does not have the sample concentration of the minimum of bacteria growing to be MIC.
The result shows that ion liquid anti-virus activities bactericide has very strong bacteriostatic activity (seeing Table 1).
The bacteriostatic activity of table 1 ion liquid anti-virus activities bactericide
Annotate: [OMIM] [MEF] is butene dioic acid mono ethyl ester Ji Xinji methylimidazole ion liquid anti-virus activities bactericide;
[OMIM] [MOF] is butene dioic acid mono octyl ester Ji Xinji methylimidazole ion liquid anti-virus activities bactericide;
[OMIM] [MBF] is butene dioic acid list phenethyl ester Ji Xinji methylimidazole ion liquid anti-virus activities bactericide;
[OMIM] [MPF] is butene dioic acid list phenylpropyl alcohol ester group octyl group methylimidazole ion liquid anti-virus activities bactericide.
Claims (10)
1. ion liquid anti-virus activities bactericide is characterized in that its general formula is:
In the general formula, R
1Be alkyl, R
2Be alkyl or any phenyl that replaces.
2. ion liquid anti-virus activities bactericide as claimed in claim 1 is characterized in that alkyl is the straight or branched alkyl with 1～8 carbon.
3. ion liquid anti-virus activities bactericide as claimed in claim 1 is characterized in that its synthetic route is:
Reflux is for refluxing in the formula, and Ionic exchange is an ion exchange process; R
1Be alkyl, R
2Be alkyl or any phenyl that replaces.
4. the synthetic method of ion liquid anti-virus activities bactericide as claimed in claim 1 is characterized in that may further comprise the steps:
1) the fumaric acid monoesters is synthetic
Maleic anhydride and alcohol are added thermal response, add anhydrous AlCl again
3Isomery agent and petroleum ether and stirring reflux, and filter, and filtrate boils off solvent and obtains thick product, and thick product adds NaOH solution or Na
2CO
3Solution or NaHCO
3Petroleum ether extraction is used in the solution dissolving, and water is regulated pH=3.5～4.5 with hydrochloric acid, divides the phase of anhydrating, washing, and drying promptly gets the pure product of fumaric acid monoesters;
2) alkyl methylimidazole quaternary ammonium base is synthetic
With N-methylimidazole and the reaction of alkyl chloride heated and stirred, tell upper strata unreacting material liquid after the reaction, obtain the thick product of chlorinated hydrocabon ylmethyl imidazoles quaternary ammonium salt, again through ethyl acetate wash the pure product of chlorinated hydrocabon ylmethyl imidazoles quaternary ammonium salt, preparation chlorinated hydrocabon ylmethyl imidazoles quaternary ammonium salt aqueous solution, cross anion-exchange column, get the alkyl methylimidazole quaternary ammonium base aqueous solution;
3) ion liquid anti-virus activities bactericide is synthetic
The fumaric acid monoesters joined in the alkyl methyl quaternary ammonium base aqueous solution react, moisture is removed in evaporation, obtains ion liquid anti-virus activities bactericide.
5. the synthetic method of ion liquid anti-virus activities bactericide as claimed in claim 4 is characterized in that in step 1), and described alcohol is through dehydration processing, and heating is reflected under the air-proof condition to be carried out.
6. the synthetic method of ion liquid anti-virus activities bactericide as claimed in claim 4 is characterized in that in step 1), in molar ratio, maleic anhydride: alcohol=1.0～1.1: 1, reaction temperature is 60～90 ℃, the reaction time is 0.5～2h.
7. the synthetic method of ion liquid anti-virus activities bactericide as claimed in claim 4 is characterized in that in step 2) in, in molar ratio, N-methylimidazole: alkyl chloride=1: 1.2～1.5.
8. the synthetic method of ion liquid anti-virus activities bactericide as claimed in claim 4, it is characterized in that in step 2) in, heated and stirred is reflected at heated and stirred reaction under the air-proof condition, and by mass percentage, the concentration of chlorinated hydrocabon ylmethyl imidazoles quaternary ammonium salt aqueous solution is 70～80%.
9. the synthetic method of ion liquid anti-virus activities bactericide as claimed in claim 4 is characterized in that in step 3), in molar ratio, and fumaric acid monoesters: the alkyl methyl quaternary ammonium base aqueous solution=1: 1.
10. the application of ion liquid anti-virus activities bactericide as claimed in claim 1 in the preparation antibacterials.
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| CN102906133A (en) * | 2010-05-18 | 2013-01-30 | 3M创新有限公司 | Polymerizable ionic liquid compositions |
| CN103242235A (en) * | 2013-05-16 | 2013-08-14 | 西北工业大学 | Chloridized 1-vinyl-3-amino-formyl methyl-imidazole bifunctional ionic liquid and synthetic method thereof |
| CN104073912A (en) * | 2014-06-25 | 2014-10-01 | 杭州师范大学 | Application of sulfur-contained ionic liquid in polyurethane complex fiber |
| CN104884038A (en) * | 2012-12-20 | 2015-09-02 | 高露洁-棕榄公司 | Oral care composition |
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| CN102906133A (en) * | 2010-05-18 | 2013-01-30 | 3M创新有限公司 | Polymerizable ionic liquid compositions |
| CN102906133B (en) * | 2010-05-18 | 2015-11-25 | 3M创新有限公司 | Polymerisable ionic liquid compositions |
| CN104884038A (en) * | 2012-12-20 | 2015-09-02 | 高露洁-棕榄公司 | Oral care composition |
| CN103242235A (en) * | 2013-05-16 | 2013-08-14 | 西北工业大学 | Chloridized 1-vinyl-3-amino-formyl methyl-imidazole bifunctional ionic liquid and synthetic method thereof |
| CN104073912A (en) * | 2014-06-25 | 2014-10-01 | 杭州师范大学 | Application of sulfur-contained ionic liquid in polyurethane complex fiber |
| CN104073912B (en) * | 2014-06-25 | 2016-08-24 | 杭州师范大学 | The application in polyurethane composite fibre of the sulfur-containing anion liquid |
| CN110123653A (en) * | 2019-05-28 | 2019-08-16 | 珠海萱嘉君行健康产业发展有限公司 | A kind of skin care item containing γ-aminobutyric acid matrine ionic liquid |
| CN115197163A (en) * | 2022-07-15 | 2022-10-18 | 广东电网有限责任公司 | Ionic liquid compound and preparation method and application thereof |
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Application publication date: 20090114 |