CN101260051A - Biodegradable choline-like ionic liquid - Google Patents
Biodegradable choline-like ionic liquid Download PDFInfo
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- CN101260051A CN101260051A CNA2008101048036A CN200810104803A CN101260051A CN 101260051 A CN101260051 A CN 101260051A CN A2008101048036 A CNA2008101048036 A CN A2008101048036A CN 200810104803 A CN200810104803 A CN 200810104803A CN 101260051 A CN101260051 A CN 101260051A
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Abstract
The invention provides choline ion liquids which are generated by taking one of three major types of compounds of naphthenic acid, fatty acid and amino acid as anion donor, and one of choline compounds as cation donor and utilizing the one-step reaction under the normal temperature and pressure. The synthesized ion liquids are measured by the corresponding biodegradability measurement method, and the degradation ratio is more than 60 percent, showing that the ion liquids can be easily bio-degraded, thereby effectively resolving the bottleneck problem that after the conventional ion liquids are finally discharged or accidentally leaked, the liquids remain in the environment and are not degraded and remain in natural environments such as water body, etc. which seriously inhibits the further large scale industrial application of ion liquids.
Description
Invention field: the present invention relates to the synthetic of a kind of biodegradable choline-like ionic liquid of chemical field.
Background of invention:
Ionic liquid with its liquid temperature wide ranges, physics and chemical stability height, steam force down, good physico-chemical property such as dissolving power is strong, designability is good, caused its research boom, and be widely used in fields such as reaction, separation, electrochemistry, material and life sciences.
Successful realization along with ion liquid scale operation and substantive industrial application, people just begin to take all factors into consideration the variety of issue in its whole life, ionic liquid is carried out environmental risk assessment, consider the environmental influence that ionic liquid may bring in application process or after finishing.People such as Jastorff suggestion to ionic liquid discharge, the multiple dimensioned risk analysis of five aspects such as space-time unique, biological accumulation, biological activity, uncertainty.People such as Scammells during institute's ignored problems, except ion liquid purity and stability problem, have also highlighted problems such as ion liquid degradability, toxicity and returnability in proposing the ionic liquid research process.Yet a series of studies show that, the conventional ionic liquid degradability as imidazoles, pyridines is very poor, this just means, these ionic liquids are after final discharging or accidental the leakage, can remain in and can not get degraded in the environment, they must be difficult for removing by present most popular biological treatment, also are difficult for reducing gradually by natural biological self-purification its content after being discharged in the physical environment such as water body.Therefore, they can constantly be accumulated in natural mediums such as water body, soil, even may enter organism and enrichment gradually by food chain, enter human body at last, are detrimental to health.This has not only seriously run counter in 12 principles of Green Chemistry the 10th: " Chemicals should be designed to not stay for a long time and be degraded to nontoxic product in environment after finishing mission ", also must seriously limit ion liquid further large-scale industrial application.Therefore, it is extremely urgent, very urgent to develop biodegradable ionic liquid.
Summary of the invention
The objective of the invention is to synthetic a kind of biodegradable ionic liquid, institute's synthetic ionic liquid is the negatively charged ion donor with naphthenic acid, lipid acid, amino acid three major types series compound, is the positively charged ion donor with the choline bases derivative.
Concrete grammar of the present invention is: choose the naphthenic compound: Cyclopentane carboxylic acid, NSC 60134, hexahydrobenzoic acid, 1-methyl isophthalic acid-hexahydrobenzoic acid, cyclohexylpropionic acid, 4-amyl group hexahydrobenzoic acid, dicyclohexyl acetate, cyclohexenecarboxylic acid, phenylformic acid, acetylsalicylic acid, Chlorlacetic Acid, 9-anthryl carboxylic acid, sylvic acid, Septochol, 5 β-ursodeoxycholic acid, 18-β-glycyrrhetinic acid, lithocholic acid, fatty acid compound: lauric acid, myristic acid, Palmiticacid, stearic acid, eicosanoic acid, oleic acid, linolic acid, linolenic acid, arachidonic acid, amino acids: glycine, leucine, methionine(Met), tyrosine, Histidine, Threonine, L-Ala, Isoleucine, tryptophane, halfcystine, Methionin, Xie Ansuan, phenylalanine, proline(Pro), Serine, arginine, aspartic acid, l-asparagine, L-glutamic acid, glutamine, 4-Hydroxyproline, the 5-hydroxylysine, a kind of in the 6-N-methyllysine is the negatively charged ion donor; Choose the choline bases derivative: a kind of for the positively charged ion donor in choline, choline chloride 60, vagusstoff, Phosphorylcholine, BuCh, benzoylcholine, the phosphatidylcholine generates choline-like ionic liquid by single step reaction under normal temperature, normal pressure.Institute's synthetic ionic liquid is in corresponding biological degradability measuring method, and degradation rate can reach more than 60%, show such ionic liquid be can and be easy to biodegradable.
Embodiment:
The present invention illustrates with following example, but the present invention is not limited to following embodiment, under the scope of described aim, changes and implements to be included in the technical scope of the present invention before and after not breaking away from.
Embodiment 1
Precision takes by weighing 0.2mol hexahydrobenzoic acid meter 25.6g, adds in the round-bottomed flask, again to wherein adding 100ml ethanol, and fully stir hexahydrobenzoic acid dissolved fully as reaction medium, the homogeneous phase solution of clear.Then under stirring condition, to the choline solution meter 52.5g that wherein slowly drips 45wt%.React 2h at ambient temperature.Reactant is rotary evaporation in vacuo 90min under 50 ℃ condition, most of ethanol is removed, liquid with gained places 50 ℃ of dry 48h of vacuum drying oven then, final that proterties is product 43.6g colourless, thick liquid, this ionic liquid closes a bottle experiment test through OECD 301D, it is in 28 days time, and degradation efficiency is 69.1%.
Embodiment 2
Precision takes by weighing Whitfield's ointment 27.6g, adds in the round-bottomed flask, again to wherein adding 100ml ethanol, and fully stir Whitfield's ointment dissolved fully as reaction medium, the homogeneous phase solution of clear.Then under stirring condition, to the choline solution 53.1g that wherein slowly drips 45wt%.Under 25 ℃ temperature condition, react 20h.Reactant is rotary evaporation in vacuo 60min under 50 ℃ condition, and most of ethanol is removed, and the liquid with gained places 50 ℃ of dry 48h of vacuum drying oven then, and is final that proterties is product 45.3g faint yellow, thick liquid.This ionic liquid closes a bottle experiment test through OECD 301D, and it is in 28 days time, and degradation efficiency is 71.4%.
Embodiment 3
Precision takes by weighing oleic acid 28.3g, adds in the round-bottomed flask, again to wherein adding 100ml ethanol, and fully stir oleic acid dissolved fully as reaction medium, the homogeneous phase solution of clear.Then under stirring condition, to the methanol solution 42.00g of the benzyltrimethylammonium hydroxide that wherein slowly drips 40wt%.Under 20 ℃ temperature condition, react 2h.Reactant is rotary evaporation in vacuo 90min under 40 ℃ condition, and most of methyl alcohol is removed, and the product with gained places 50 ℃ of dry 48h of vacuum drying oven then, the final product 43.7g that gets.This ionic liquid closes a bottle experiment test through OECD 301D, and it is in 28 days time, and degradation efficiency is 79.2%.
Embodiment 4
Precision takes by weighing L-Ala 8.91g, adds in the round-bottomed flask, again to wherein adding 10ml ethanol, and fully stir L-Ala dissolved fully as reaction medium, the homogeneous phase solution of clear.Then under stirring condition, to the methanol solution 42.00g of the benzyltrimethylammonium hydroxide that wherein slowly drips 40wt%.Under 15 ℃ temperature condition, react 24h.Reactant is rotary evaporation in vacuo 60min under 40 ℃ condition, methyl alcohol in the methanol solution of most of reaction medium ethanol and benzyltrimethylammonium hydroxide is removed, product with gained places 50 ℃ of dry 48h of vacuum drying oven then, the final product 22.9g that gets.This ionic liquid closes a bottle experiment test through OECD 301D, and it is in 28 days time, and degradation efficiency is 74.6%.
Claims (6)
1. biodegradable choline-like ionic liquid, it is characterized in that such ionic liquid is is the negatively charged ion donor with degradable monobasic organic acid carboxylic-acid series compound, with the choline is the positively charged ion donor, reaction certain hour synthetic under certain temperature, pressure condition.
2. method according to claim 1, wherein such ion liquid negatively charged ion donor is an organic carboxyl acid class series compound, mainly comprise naphthenic acid, lipid acid, the amino acid three major types, wherein naphthenic acid mainly comprises Cyclopentane carboxylic acid, NSC 60134, hexahydrobenzoic acid, 1-methyl isophthalic acid-hexahydrobenzoic acid, cyclohexylpropionic acid, 4-amyl group hexahydrobenzoic acid, dicyclohexyl acetate, cyclohexenecarboxylic acid, phenylformic acid, acetylsalicylic acid, Chlorlacetic Acid, 9-anthryl carboxylic acid, sylvic acid, Septochol, 5 β-ursodeoxycholic acid, 18-β-glycyrrhetinic acid, lithocholic acid, lipid acid mainly comprises lauric acid, myristic acid, Palmiticacid, stearic acid, eicosanoic acid, oleic acid, linolic acid, linolenic acid, arachidonic acid, amino acid mainly comprise glycine, leucine, methionine(Met), tyrosine, Histidine, Threonine, L-Ala, Isoleucine, tryptophane, halfcystine, Methionin, Xie Ansuan, phenylalanine, proline(Pro), Serine, arginine, aspartic acid, l-asparagine, L-glutamic acid, glutamine, 4-Hydroxyproline, the 5-hydroxylysine, the 6-N-methyllysine.
3. method according to claim 1, wherein such ion liquid positively charged ion donor is a choline, mainly comprises choline, choline chloride 60, vagusstoff, Phosphorylcholine, BuCh, benzoylcholine, phosphatidylcholine.
4. according to the described method of claim 1～3, wherein such ion liquid synthetic mainly be to choose a kind of in the above-mentioned yin, yang ion donor compound separately, finish by a step neutralization reaction.
5. method according to claim 1, wherein such ionic liquid is under normal pressure, 10～90 ℃ temperature condition is reaction 1～24h synthetic down.
6. method according to claim 1, such ionic liquid closes in the bottle experiment at the biological degradability measuring method, and degradation rate can reach more than 60%, shows that such ionic liquid is can be biodegradable.
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| CNA2008101048036A CN101260051A (en) | 2008-04-24 | 2008-04-24 | Biodegradable choline-like ionic liquid |
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| CNA2008101048036A CN101260051A (en) | 2008-04-24 | 2008-04-24 | Biodegradable choline-like ionic liquid |
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Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102190589A (en) * | 2010-03-04 | 2011-09-21 | 中国科学院过程工程研究所 | Amino acid ionic liquid for foodstuffs and medical treatments |
| CN102333462A (en) * | 2009-01-12 | 2012-01-25 | Vtu控股有限公司 | Tobacco filter |
| JP2012031137A (en) * | 2010-06-29 | 2012-02-16 | Miyoshi Oil & Fat Co Ltd | Hydrophilic ionic liquid |
| CN103031762A (en) * | 2011-09-30 | 2013-04-10 | 中国科学院过程工程研究所 | Method for preparing material rich in cellulose in degradable ionic liquid solvent |
| CN103242176A (en) * | 2013-05-15 | 2013-08-14 | 台州学院 | Functional ionic liquid based on choline chloride, and preparation method of same |
| CN103710393A (en) * | 2013-12-31 | 2014-04-09 | 浙江工业大学 | Method for preparing chiral alcohol by use of small peptides-containing ionic liquid reaction system |
| CN103896871A (en) * | 2014-04-17 | 2014-07-02 | 安徽工业大学 | Method for preparing 5-arylmethylene-2, 4-thiazolidinedione derivative through catalysis of degradable basic ionic liquid |
| CN104645874A (en) * | 2015-02-05 | 2015-05-27 | 中国林业科学研究院林产化学工业研究所 | Rosin-based choline quaternary ammonium salt surfactant and preparation method thereof |
| CN105916969A (en) * | 2013-11-28 | 2016-08-31 | 贝尔法斯特女王大学 | Removal of free fatty acids from glyceride oils |
| CN107312109A (en) * | 2016-04-26 | 2017-11-03 | 中国科学院过程工程研究所 | Chitin separating and extracting process in a kind of shrimp and crab shells based on degradable ionic liquid |
| CN108794652A (en) * | 2017-04-26 | 2018-11-13 | 中国科学院过程工程研究所 | A kind of chitin integraterd manufacturing system and its processing method |
| CN109575023A (en) * | 2018-12-03 | 2019-04-05 | 深圳市萱嘉生物科技有限公司 | A kind of matrine long chain fatty acids ionic liquid and the preparation method and application thereof |
| CN109970584A (en) * | 2019-03-22 | 2019-07-05 | 天津大学 | A kind of preparation method of choline amino acid ion liquid |
| CN112674106A (en) * | 2021-01-06 | 2021-04-20 | 沈阳农业大学 | Soluble agent and preparation method thereof |
| CN115232048A (en) * | 2021-04-22 | 2022-10-25 | 南京毓浠医药技术有限公司 | Ionic liquid and preparation method and application thereof |
| CN115594773A (en) * | 2022-09-22 | 2023-01-13 | 黔南民族师范学院（Cn） | Eucommia ulmoides leaf extraction method with high polysaccharide yield and application thereof |
| CN116199880A (en) * | 2023-03-16 | 2023-06-02 | 烟台先进材料与绿色制造山东省实验室 | Amino acid-based ionic liquid, preparation method and application thereof, and water-based lubricant |
-
2008
- 2008-04-24 CN CNA2008101048036A patent/CN101260051A/en active Pending
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102333462A (en) * | 2009-01-12 | 2012-01-25 | Vtu控股有限公司 | Tobacco filter |
| CN102190589A (en) * | 2010-03-04 | 2011-09-21 | 中国科学院过程工程研究所 | Amino acid ionic liquid for foodstuffs and medical treatments |
| JP2012031137A (en) * | 2010-06-29 | 2012-02-16 | Miyoshi Oil & Fat Co Ltd | Hydrophilic ionic liquid |
| CN103031762A (en) * | 2011-09-30 | 2013-04-10 | 中国科学院过程工程研究所 | Method for preparing material rich in cellulose in degradable ionic liquid solvent |
| CN103031762B (en) * | 2011-09-30 | 2014-11-05 | 中国科学院过程工程研究所 | Method for preparing material rich in cellulose in degradable ionic liquid solvent |
| CN103242176A (en) * | 2013-05-15 | 2013-08-14 | 台州学院 | Functional ionic liquid based on choline chloride, and preparation method of same |
| CN103242176B (en) * | 2013-05-15 | 2015-12-09 | 台州学院 | Based on the functional ion liquid and preparation method thereof of choline chloride 60 |
| CN105916969B (en) * | 2013-11-28 | 2020-03-20 | 贝尔法斯特女王大学 | Removal of free fatty acids from glyceride oils |
| CN105916969A (en) * | 2013-11-28 | 2016-08-31 | 贝尔法斯特女王大学 | Removal of free fatty acids from glyceride oils |
| CN103710393B (en) * | 2013-12-31 | 2016-03-09 | 浙江工业大学 | Utilize the method preparing chiral alcohol containing small peptide class ionic liquid reaction system |
| CN103710393A (en) * | 2013-12-31 | 2014-04-09 | 浙江工业大学 | Method for preparing chiral alcohol by use of small peptides-containing ionic liquid reaction system |
| CN103896871A (en) * | 2014-04-17 | 2014-07-02 | 安徽工业大学 | Method for preparing 5-arylmethylene-2, 4-thiazolidinedione derivative through catalysis of degradable basic ionic liquid |
| CN103896871B (en) * | 2014-04-17 | 2015-10-07 | 安徽工业大学 | The method of 5-aryl methylene-2,4-thiazolidinedione derivative is prepared in the catalysis of a kind of degradable alkali ionic liquid |
| CN104645874A (en) * | 2015-02-05 | 2015-05-27 | 中国林业科学研究院林产化学工业研究所 | Rosin-based choline quaternary ammonium salt surfactant and preparation method thereof |
| CN107312109A (en) * | 2016-04-26 | 2017-11-03 | 中国科学院过程工程研究所 | Chitin separating and extracting process in a kind of shrimp and crab shells based on degradable ionic liquid |
| CN108794652A (en) * | 2017-04-26 | 2018-11-13 | 中国科学院过程工程研究所 | A kind of chitin integraterd manufacturing system and its processing method |
| CN109575023A (en) * | 2018-12-03 | 2019-04-05 | 深圳市萱嘉生物科技有限公司 | A kind of matrine long chain fatty acids ionic liquid and the preparation method and application thereof |
| CN109970584B (en) * | 2019-03-22 | 2022-04-05 | 天津大学 | Preparation method of choline amino acid ionic liquid |
| CN109970584A (en) * | 2019-03-22 | 2019-07-05 | 天津大学 | A kind of preparation method of choline amino acid ion liquid |
| CN112674106A (en) * | 2021-01-06 | 2021-04-20 | 沈阳农业大学 | Soluble agent and preparation method thereof |
| CN112674106B (en) * | 2021-01-06 | 2021-12-07 | 沈阳农业大学 | Soluble agent and preparation method thereof |
| CN115232048A (en) * | 2021-04-22 | 2022-10-25 | 南京毓浠医药技术有限公司 | Ionic liquid and preparation method and application thereof |
| WO2022222844A1 (en) * | 2021-04-22 | 2022-10-27 | 南京毓浠医药技术有限公司 | Ionic liquid, preparation method therefor, and application thereof |
| CN115232048B (en) * | 2021-04-22 | 2024-02-27 | 南京毓浠医药技术有限公司 | Ionic liquid and preparation method and application thereof |
| CN115594773A (en) * | 2022-09-22 | 2023-01-13 | 黔南民族师范学院（Cn） | Eucommia ulmoides leaf extraction method with high polysaccharide yield and application thereof |
| CN116199880A (en) * | 2023-03-16 | 2023-06-02 | 烟台先进材料与绿色制造山东省实验室 | Amino acid-based ionic liquid, preparation method and application thereof, and water-based lubricant |
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