CN105037062A - Alcohol-based ternary deep-eutectic solvent and preparation method thereof - Google Patents
Alcohol-based ternary deep-eutectic solvent and preparation method thereof Download PDFInfo
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Abstract
An alcohol-based ternary deep-eutectic solvent is composed of a ternary system comprising an alcohol group, a hydrogen-bond donor and quaternary ammonium salt. A preparation method for the alcohol-based ternary deep-eutectic solvent comprises the following steps: uniformly mixing the alcohol group, the hydrogen-bond donor and quaternary ammonium salt, heating the mixture to 60-100 DEG C, and keeping heat for 0.5-2 h until materials are completely dissolved; after completion of reaction, putting the mixture into a drying oven for drying for 12 h at the temperature of 80 DEG C so as to obtain viscous liquid namely the target object; the alcohol-based ternary deep-eutectic solvent is used as a mobile phase additive in high performance liquid chromatography, and used for extraction separation of bioactive components, organic catalytic synthesis and gas absorption. The alcohol-based ternary deep-eutectic solvent has the advantages as follows: the preparation method is simple in process, raw materials are easy to obtain, by-products are not produced in the reaction process, the product can be biodegradable, pollution to the environment is reduced greatly, and the prepared product is high in purity, low in melting point and viscosity, high in stability and suitable for industrial production.
Description
Technical field
The present invention relates to the technology of preparing of solvent, relate in particular to a kind of ternary eutectic solvent based on alcohol radical and preparation method thereof.
Background technology
The unique physicochemical property such as ionic liquid has that steam forces down, non-combustible, solvability and excellent conductivity, electrochemical stability window are wide, receive much attention in fields such as isolation technique, biocatalysis, organic synthesis and electrochemistry.But, the shortcomings such as ionic liquid existence synthesis complexity, purification difficult, cost are higher, thus limit its heavy industrialization application and development.In addition, relevant toxicological study shows, pyridine and glyoxaline ion liquid non-fully " green ", and its toxicity is suitable with conventional organic solvents, is even greater than conventional organic solvents.Therefore, find simple, the economic and more green replace solvents tool of synthesis to be of great significance.
2003, the solvent-eutectic solvent (DeepEutecticSolvents) of a kind of excellent in physical and chemical performance having quaternary ammonium salt and amide compound to be formed of the Late Cambrian such as Abbott.This nontoxic solvent, biodegradable, and building-up process atom utilization reaches 100%, is a kind of novel green solvent.The physical properties of eutectic solvent is extremely similar to ionic liquid, therefore also has people that it is classified as a class novel ion liquid or ionic liquid analogue.At present, eutectic solvent has caused the interest of the investigator of countries in the world, and demonstrates good application prospect in fields such as sepn process, chemical reaction, functional materials and electrochemistry.
Summary of the invention
The object of the invention is for above-mentioned existing problems, a kind of ternary eutectic solvent based on alcohol radical and preparation method thereof is provided, this preparation method's technique is simple, raw material is easy to get, cost is low, and in reaction process not with an organic solvent, also toxic substance can not be discharged, environmental friendliness, no coupling product, biodegradable, be suitable for large-scale industrial production.
Technical scheme of the present invention:
A kind of ternary eutectic solvent based on alcohol radical, be made up of alcohol radical-hydrogen-bond donor-quaternary ammonium salt ternary system, wherein alcohol radical is ethylene glycol, 1,2-PD, glycerol, 1,2-butyleneglycol, 1,3-butyleneglycol, 1,4-butyleneglycol, 2,3-butanediol or 1,6-hexylene glycol, hydrogen-bond donor is oxalic acid, citric acid or urea, and quaternary ammonium salt is choline chloride 60; The mol ratio 0.5-4:1:1 of alcohol radical, hydrogen-bond donor and quaternary ammonium salt.
A described preparation method based on the ternary eutectic solvent of alcohol radical, by alcohol radical, hydrogen-bond donor and quaternary ammonium salt mix, and after being heated to 60-100 DEG C, keep 0.5-2h to dissolve completely to material; Put into baking oven after having reacted at 80 DEG C of temperature dry 12 hours, obtain thick liquid, obtained target compound.
A described application based on the ternary eutectic solvent of alcohol radical, as Mobile Phase Additives in high performance liquid chromatography, for the extraction and isolation of bioactive ingredients, organic catalysis synthesis and gas absorption.
The invention has the beneficial effects as follows:
1) simple, the raw material of this preparation method's technique is easy to get, do not need with an organic solvent in reaction process, also toxic substance can not be discharged, no coupling product, product can biological degradation, and greatly reducing the pollution to environment, obtained product purity is high, separating-purifying that need not be complicated, is applicable to suitability for industrialized production;
2) the inorganic liquid phase that the invention enables some material to become from single solid transformation, also provides new way prepared by a kind of organic-inorganic hybridized material for this reason;
3) because hydrogen-bond donor molecular energy and monovalence halide anion form hydrogen bond, increase steric restriction, distance between zwitterion is increased, thus form the eutectic solvent of low melting point, the eutectic solvent a kind of low melting point (room temperature or lower than room temperature) being prepared by the combination of multiple solid matter, can by the fusing point changing the difference composition of three kinds of components, ratio regulates synthetic materials, specific conductivity and soda acid character;
4) fusing point of ternary eutectic solvent prepared of the present invention and viscosity is lower, stability is higher, placing the several months can keep stable, can be used for the catalysis etc. of organic synthesis as novel dissolvent.
Embodiment
Below in conjunction with specific embodiment, set forth the present invention further.Should be understood that these implement only to be not used in for illustration of the present invention to limit the scope of the invention.In addition should be understood that those skilled in the art can make various changes or modifications the present invention, and these equivalent form of values fall within the application's appended claims limited range equally after the content of having read the present invention's instruction.
Embodiment 1:
Based on a ternary eutectic solvent for alcohol radical, be made up of alcohol radical-hydrogen-bond donor-quaternary ammonium salt ternary system, wherein alcohol radical is 1,2-PD, and hydrogen-bond donor is urea, and quaternary ammonium salt is choline chloride 60; The mol ratio 1:1:1 of alcohol radical, hydrogen-bond donor and quaternary ammonium salt.
The preparation method of the described ternary eutectic solvent based on alcohol radical, by 7.31 milliliters of (0.01mol) 1,2-propylene glycol, 6.00 grams of (0.01mol) urea mix with 14.00 grams of (0.01mol) choline chloride 60s, be heated to 60 DEG C and keep 1h to dissolve completely to material, forming water white transparency clarified liq; Put into baking oven after having reacted at 80 DEG C of temperature dry 12 hours, obtain thick liquid, obtained eutectic solvent 1,2-PD-urea-choline chloride 60.
The application of the described ternary eutectic solvent based on alcohol radical, as Mobile Phase Additives in high performance liquid chromatography, for bioactive ingredients extraction and isolation, organic catalysis synthesis and gas absorption.
Embodiment 2:
Based on a ternary eutectic solvent for alcohol radical, be made up of alcohol radical-hydrogen-bond donor-quaternary ammonium salt ternary system, wherein alcohol radical is ethylene glycol, and hydrogen-bond donor is urea, and quaternary ammonium salt is choline chloride 60; The mol ratio 1:1:1 of alcohol radical, hydrogen-bond donor and quaternary ammonium salt.
The preparation method of the described ternary eutectic solvent based on alcohol radical, 5.58 milliliters of (0.1mol) ethylene glycol, 6.00 grams of (0.01mol) urea are mixed with 14.00 grams of (0.1mol) choline chloride 60s, be heated to 80 DEG C, and keep 1h, form water white transparency clarified liq; Put into baking oven after having reacted at 80 DEG C of temperature dry 12 hours, obtain thick liquid, obtained eutectic solvent ethylene glycol-urea-choline chloride 60.
The application of the described ternary eutectic solvent based on alcohol radical, as Mobile Phase Additives in high performance liquid chromatography, for bioactive ingredients extraction and isolation, organic catalysis synthesis and gas absorption.
Embodiment 3:
Based on a ternary eutectic solvent for alcohol radical, be made up of alcohol radical-hydrogen-bond donor-quaternary ammonium salt ternary system, wherein alcohol radical is ethylene glycol, and hydrogen-bond donor is citric acid, and quaternary ammonium salt is choline chloride 60; The mol ratio 1:1:1 of alcohol radical, hydrogen-bond donor and quaternary ammonium salt.
The preparation method of the described ternary eutectic solvent based on alcohol radical, by 5.58 milliliters of (0.1mol) ethylene glycol, 19.21 grams of (0.1mol) citric acids mix with 14.00 grams of (0.1mol) choline chloride 60s, be heated to 80 DEG C and keep 1h, forming water white transparency clarified liq; Put into baking oven after having reacted at 80 DEG C of temperature dry 12 hours, obtain thick liquid, obtained eutectic solvent ethylene glycol-citric acid-choline chloride 60.
The application of the described ternary eutectic solvent based on alcohol radical, as Mobile Phase Additives in high performance liquid chromatography, for bioactive ingredients extraction and isolation, organic catalysis synthesis and gas absorption.
Embodiment 4:
Based on a ternary eutectic solvent for alcohol radical, be made up of alcohol radical-hydrogen-bond donor-quaternary ammonium salt ternary system, wherein alcohol radical is glycerol, and hydrogen-bond donor is citric acid, and quaternary ammonium salt is choline chloride 60; The mol ratio 1:1:1 of alcohol radical, hydrogen-bond donor and quaternary ammonium salt.
The preparation method of the described ternary eutectic solvent based on alcohol radical, by 7.12 milliliters of (0.1mol) glycerol, 19.21 grams of (0.1mol) citric acids mix with 14.00 grams of (0.1mol) choline chloride 60s, be heated to 80 DEG C, and keep 2h, form water white transparency clarified liq; Put into baking oven after having reacted at 80 DEG C of temperature dry 12 hours, obtain thick liquid, obtained eutectic solvent eutectic solvent glycerol-citric acid-choline chloride 60.
The application of the described ternary eutectic solvent based on alcohol radical, as Mobile Phase Additives in high performance liquid chromatography, for bioactive ingredients extraction and isolation, organic catalysis synthesis and gas absorption.
Embodiment 5:
Based on a ternary eutectic solvent for alcohol radical, be made up of alcohol radical-hydrogen-bond donor-quaternary ammonium salt ternary system, wherein alcohol radical is ethylene glycol, and hydrogen-bond donor is oxalic acid, and quaternary ammonium salt is choline chloride 60; The mol ratio 1:1:1 of alcohol radical, hydrogen-bond donor and quaternary ammonium salt.
The preparation method of the described ternary eutectic solvent based on alcohol radical, by 5.58 milliliters of (0.1mol) ethylene glycol, 9.00 grams of (0.1mol) oxalic acid mix with 14.00 grams of (0.1mol) choline chloride 60s, be heated to 100 DEG C, and keep 1h, form water white transparency clarified liq; Put into baking oven after having reacted at 80 DEG C of temperature dry 12 hours, obtain thick liquid, obtained eutectic solvent eutectic solvent ethylene glycol-oxalic acid-choline chloride 60.
The application of the described ternary eutectic solvent based on alcohol radical, as Mobile Phase Additives in high performance liquid chromatography, for bioactive ingredients extraction and isolation, organic catalysis synthesis and gas absorption.
Embodiment 6:
Based on a ternary eutectic solvent for alcohol radical, be made up of alcohol radical-hydrogen-bond donor-quaternary ammonium salt ternary system, wherein alcohol radical is propylene glycol, and hydrogen-bond donor is oxalic acid, and quaternary ammonium salt is choline chloride 60; The mol ratio 1:1:1 of alcohol radical, hydrogen-bond donor and quaternary ammonium salt.
The preparation method of the described ternary eutectic solvent based on alcohol radical, by 7.31 milliliters of (0.1mol) 1,2-propylene glycol, 9.00 grams of (0.1mol) oxalic acid mix with 14.00 grams of (0.1mol) choline chloride 60s, be heated to 100 DEG C, and keep 2h, form water white transparency clarified liq; Put into baking oven after having reacted at 80 DEG C of temperature dry 12 hours, obtain thick liquid, obtained eutectic solvent 1,2-PD-oxalic acid-choline chloride 60.
The application of the described ternary eutectic solvent based on alcohol radical, as Mobile Phase Additives in high performance liquid chromatography, for bioactive ingredients extraction and isolation, organic catalysis synthesis and gas absorption.
The above; be only part embodiment of the present invention, but protection scope of the present invention is not limited thereto, any those skilled in the art are in the technical scope that the present invention discloses; the change that can expect easily or replacement, all should be encompassed within protection scope of the present invention.
Claims (3)
1. the ternary eutectic solvent based on alcohol radical, it is characterized in that: be made up of alcohol radical-hydrogen-bond donor-quaternary ammonium salt ternary system, wherein alcohol radical is ethylene glycol, 1,2-PD, glycerol, 1,2-butyleneglycol, 1,3-butyleneglycol, 1,4-butyleneglycol, 2,3-butanediol or 1,6-hexylene glycol, hydrogen-bond donor is oxalic acid, citric acid or urea, and quaternary ammonium salt is choline chloride 60; The mol ratio 0.5-4:1:1 of alcohol radical, hydrogen-bond donor and quaternary ammonium salt.
2. as claimed in claim 1 based on a preparation method for the ternary eutectic solvent of alcohol radical, it is characterized in that: by alcohol radical, hydrogen-bond donor and quaternary ammonium salt mix, and after being heated to 60-100 DEG C, keep 0.5-2h to dissolve completely to material; Put into baking oven after having reacted at 80 DEG C of temperature dry 12 hours, obtain thick liquid, obtained target compound.
3., as claimed in claim 1 based on an application for the ternary eutectic solvent of alcohol radical, it is characterized in that: as Mobile Phase Additives in high performance liquid chromatography, for bioactive ingredients extraction and isolation, organic catalysis synthesis and gas absorption.
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Cited By (18)
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| CN105439911A (en) * | 2015-11-27 | 2016-03-30 | 盐城师范学院 | Ethoxyl inner salt based eutectic substance |
| CN105481732A (en) * | 2015-11-27 | 2016-04-13 | 盐城师范学院 | Inner-salt-based three-component eutectic ionic liquid |
| CN106290689A (en) * | 2016-09-27 | 2017-01-04 | 深圳市计量质量检测研究院 | Eutectic solvent extract phase chromatography quickly measures AFB1, Basic Orange II and the method for basic flavine O |
| CN108030809A (en) * | 2018-01-26 | 2018-05-15 | 山西大学 | A kind of extracting method of Fructus Forsythiae anti-inflammatory antioxidant content |
| CN108261801A (en) * | 2018-02-09 | 2018-07-10 | 长治学院 | A kind of stationary phase containing eutectic solvent and its preparation method and application |
| CN108424534A (en) * | 2018-04-09 | 2018-08-21 | 合肥工业大学 | A kind of eutectic solvent and its dissolving method that can dissolve polyethylene glycol |
| CN109609271A (en) * | 2018-11-21 | 2019-04-12 | 浙江工业大学 | A kind of method of essential oil in extraction Chinese medicine |
| CN109851821A (en) * | 2019-03-19 | 2019-06-07 | 合肥工业大学 | A kind of eutectic solvent and its dissolving method that can effectively dissolve hyper-branched polyester |
| CN110590730A (en) * | 2019-09-26 | 2019-12-20 | 浙江工商大学 | Method for extracting perilla leaf anthocyanin by using ternary eutectic solvent |
| CN110760552A (en) * | 2019-11-27 | 2020-02-07 | 湘潭大学 | Pretreatment method for improving saccharification efficiency of lignocellulose |
| CN110845715A (en) * | 2019-12-09 | 2020-02-28 | 东北林业大学 | Method for preparing polyaryl ether polyol by using biomass |
| CN111073458A (en) * | 2019-12-31 | 2020-04-28 | 广州中海环保科技有限公司 | Preparation method for improving drying speed of water-based epoxy primer |
| CN111087299A (en) * | 2019-12-13 | 2020-05-01 | 华南理工大学 | Method for extracting vanillic acid by using eutectic solvent/n-propanol aqueous two-phase system |
| CN111808631A (en) * | 2020-06-22 | 2020-10-23 | 江苏中江材料技术研究院有限公司 | Catalytic oxidation desulfurization method for choline ternary eutectic solvent |
| CN111979280A (en) * | 2020-09-11 | 2020-11-24 | 东北林业大学 | Multi-hydrogen bond association solvent and method for preparing glucose by using wood fiber |
| CN112125894A (en) * | 2020-09-30 | 2020-12-25 | 内蒙古民族大学 | Method for green and efficient extraction of red clover isoflavone by using natural deep eutectic solvent |
| CN113372202A (en) * | 2021-06-24 | 2021-09-10 | 华南理工大学 | Method for extracting and separating eugenol and syringic acid by using aqueous two-phase system |
| CN113764713A (en) * | 2021-08-03 | 2021-12-07 | 江苏大学 | Flow battery based on ternary eutectic solvent |
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| CN105481732A (en) * | 2015-11-27 | 2016-04-13 | 盐城师范学院 | Inner-salt-based three-component eutectic ionic liquid |
| CN105439911A (en) * | 2015-11-27 | 2016-03-30 | 盐城师范学院 | Ethoxyl inner salt based eutectic substance |
| CN106290689A (en) * | 2016-09-27 | 2017-01-04 | 深圳市计量质量检测研究院 | Eutectic solvent extract phase chromatography quickly measures AFB1, Basic Orange II and the method for basic flavine O |
| CN106290689B (en) * | 2016-09-27 | 2018-01-02 | 深圳市计量质量检测研究院 | The method that eutectic solvent extraction liquid chromatography quickly determines aflatoxin B1, Basic Orange II and basic flavine O |
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| CN108424534B (en) * | 2018-04-09 | 2020-10-23 | 合肥工业大学 | Eutectic solvent capable of dissolving polyethylene glycol and dissolving method thereof |
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| CN109609271A (en) * | 2018-11-21 | 2019-04-12 | 浙江工业大学 | A kind of method of essential oil in extraction Chinese medicine |
| CN109851821B (en) * | 2019-03-19 | 2021-08-13 | 合肥工业大学 | Eutectic solvent capable of effectively dissolving hyperbranched polyester and dissolving method thereof |
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| CN110590730A (en) * | 2019-09-26 | 2019-12-20 | 浙江工商大学 | Method for extracting perilla leaf anthocyanin by using ternary eutectic solvent |
| CN110590730B (en) * | 2019-09-26 | 2021-09-03 | 浙江工商大学 | Method for extracting perilla leaf anthocyanin by using ternary eutectic solvent |
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| CN111979280B (en) * | 2020-09-11 | 2022-04-15 | 东北林业大学 | Multi-hydrogen bond association solvent and method for preparing glucose by using wood fiber |
| CN112125894A (en) * | 2020-09-30 | 2020-12-25 | 内蒙古民族大学 | Method for green and efficient extraction of red clover isoflavone by using natural deep eutectic solvent |
| CN112125894B (en) * | 2020-09-30 | 2022-05-27 | 内蒙古民族大学 | Method for green and efficient extraction of red clover isoflavone by using natural deep eutectic solvent |
| CN113372202A (en) * | 2021-06-24 | 2021-09-10 | 华南理工大学 | Method for extracting and separating eugenol and syringic acid by using aqueous two-phase system |
| CN113372202B (en) * | 2021-06-24 | 2022-04-22 | 华南理工大学 | Method for extracting and separating eugenol and syringic acid by using aqueous two-phase system |
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| CN113764713B (en) * | 2021-08-03 | 2023-10-13 | 江苏大学 | Flow battery based on ternary eutectic solvent |
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| C06 | Publication | ||
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Application publication date: 20151111 |