CN107200787B - A kind of imidazoles alginate ionic liquid and its synthetic method - Google Patents

A kind of imidazoles alginate ionic liquid and its synthetic method Download PDF

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CN107200787B
CN107200787B CN201710368724.5A CN201710368724A CN107200787B CN 107200787 B CN107200787 B CN 107200787B CN 201710368724 A CN201710368724 A CN 201710368724A CN 107200787 B CN107200787 B CN 107200787B
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imidazoles
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CN107200787A (en
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陶国宏
汪游
何玲
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Sichuan University
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    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0084—Guluromannuronans, e.g. alginic acid, i.e. D-mannuronic acid and D-guluronic acid units linked with alternating alpha- and beta-1,4-glycosidic bonds; Derivatives thereof, e.g. alginates

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Abstract

The invention discloses a kind of imidazoles alginate ionic liquid and its synthetic methods.The structure of the ionic liquid is for example shown below shown:Wherein R1、R3For H atom, alkyl (carbon chain lengths 1~20) or substituted hydrocarbon radical；R2For H atom or methyl；[Alg]‑For seaweed acid radical anion.The ionic liquid synthesized in the present invention is water-soluble and the state of clear is presented, such ionic liquid can effectively play the characteristic of its seaweed acid radical anion, material carrier, in terms of have important application.Its synthetic method is mainly characterized by: raw material is easy preparation, and cost is relatively low；The substance of reaction condition and process green, nonpollution environment and harmful to human generates；Synthetic method is simple, and products pure no coupling product, purification process is simple, is suitble to high-volume large-scale production.

Description

A kind of imidazoles alginate ionic liquid and its synthetic method
Technical field
The present invention relates to new material technology fields, more particularly to a kind of imidazoles alginate ionic liquid and its synthesis Method.
Background technique
Ionic liquid is that the low temperature or room temperature molten salt that are formed are combined with anion by the cation of different structure.Ion Liquid has many excellent physicochemical properties, such as difficult volatilization, thermostabilization, wider electrochemical window and liquid phase section Deng so that ionic liquid becomes the popular domain of research in recent years, catalyzing and synthesizing, extraction and separation, gas absorbs, analysis is surveyed Examination, electrochemistry etc. have important application.Functionalized design is carried out to the zwitterion building stone of ionic liquid, it can be with Obtain the functionalized ion liquid for having both the two characteristic.
Glyoxaline ion liquid is an important branch in ionic liquid, this has benefited from low caused by glyoxaline cation The advantages of fusing point, low viscosity, high stability, field of ionic liquid was most for the report of this kind of ionic liquids in recent years, closed It is graduallyd mature at research method, it is theoretical gradually perfect.
Natural seaweed hydrochlorate is a kind of natural polymers, in marine organisms seaweed, belongs to a kind of polysaccharide. Sodium alginate is the most common unitary alginate, can be dissolved in water, forms viscous aqueous solution, and heating can promote sodium alginate Dissolution, obtains light yellow transparent solution.Sodium alginate have it is very strong sequestering, stable complexing can be formed for metal ion Object.Therefore, it can be used as a kind of important metal absorbent.Sodium alginate contains more rich-COO—, there is very high ion Function of exchange can be reacted with other materials, obtain different alginate derivatives.Sodium alginate can and Ca2+、 Co2+、Cu2+、Fe2+、Zn2+Equal divalent metals crosslinking, forms a kind of " egg-box " (egg-box) structure, this kind of alginic acid Salt is a kind of good hydrogel, has the function of keeping moisture, carries substance.
Summary of the invention
In order to solve the above technical problems, the present invention provides a kind of imidazoles alginate ionic liquid and its synthetic method.
Of the invention, including
The structural formula of a kind of imidazoles alginate ionic liquid, imidazoles alginate ion is as follows:
Wherein R1、R3For H atom, alkyl (carbon chain lengths 1~20) or substituted hydrocarbon radical；R2For H atom or methyl；[Alg]— For seaweed acid radical anion.
Alkyl (carbon chain lengths 1~20) or substituted hydrocarbon radical can be methyl, ethyl, propyl, butyl, amyl, hexyl, pungent Base, decyl, dodecyl, myristyl, cetyl, octadecyl, allyl, acetonyl, cyanoethyl, ethyl acetate base, Any one in acetenyl.
A kind of synthetic method of imidazoles alginate ionic liquid, comprising the following steps: according to imidazolium hydroxide: Brand-new alginic acid=1:1~1.1 molar ratio mixes the two in a solvent, stirs evenly, and centrifugation is taken out clear after reaction Liquid, and solvent is removed, imidazoles alginate ionic liquid can be obtained.
It is above-mentioned to can be the one or more such as water, dichloroethanes, isopropanol, preferably water or isopropanol using solvent.
Reaction temperature is room temperature to 75 DEG C, preferably room temperature；Reaction time is 1~72 hour.
Imidazoles alginate ionic liquid provided by the invention specifically: 1,3- methylimidazole alginate ionic liquid Body [C1Mim] [Alg], 1- methyl -3- ethyl imidazol(e) alginate ionic liquid [C2Mim] [Alg], 1- methyl -3- butyl imidazole Alginate ionic liquid [C4Mim] [Alg], 1- methyl -3- hexyl imidazolium alginate ionic liquid [C6mim][Alg]、1- Methyl -3- octylimidazole alginate ionic liquid [C8Mim] [Alg], 1- methyl -3- decyl imidazoles alginate ionic liquid [C10Mim] [Alg], 1- methyl -3- dodecyl imidazole alginate ionic liquid [C12Mim] [Alg], 1- methyl -3- 14 Alkyl imidazole alginate ionic liquid [C14Mim] [Alg], 1- methyl -3- cetyl imidazoles alginate ionic liquid [C16Mim] [Alg], 1- methyl -3- octadecyl imidazoles alginate ionic liquid [C18Mim] [Alg], 1- methyl -3- allyl Base imidazoles alginate ionic liquid [Amim] [Alg], 1- methyl -3- acetonyl imidazoles alginate ionic liquid [MeCOCH2Mim] [Alg], 1- methyl -3- cyanoethyl imidazoles alginate ionic liquid [NCCH2Mim] [Alg], 1- methyl -3- Ethyl acetate base imidazoles alginate ionic liquid [CH3CH2OOCCH2Mim] [Alg], 1- methyl -3- acetenyl imidazoles alginic acid Ionic liquid [HCCH2Mim] [Alg], 1- ethyl -3- butyl imidazole alginate ionic liquid [C2C4Im] [Alg], 1- third Base -3- butyl imidazole alginate ionic liquid [C3C4Im] [Alg], 1,3- dibutyl imidazoles alginate ionic liquid [C4C4Im] [Alg], 1- butyl -3- amyl imidazoles alginate ionic liquid [C4C5Im] [Alg], 1- butyl -3- hexyl imidazolium Alginate ionic liquid [C4C6Im] [Alg], 1,2,3- tri-methylimidazolium alginate ionic liquid [C1mmim][Alg]、1, 2- dimethyl -3- ethyl imidazol(e) alginate ionic liquid [C2Mmim] [Alg], 1,2- dimethyl -3- propyl imidazole alginic acid Ionic liquid [C3Mmim] [Alg], 1,2- dimethyl -3- butyl imidazole alginate ionic liquid [C4mmim][Alg]。
The beneficial effects of the present invention are:
(1) seaweed acid ion is introduced into ionic liquid, so that product has both the excellent of ionic liquid and alginate Benign matter has wide Research Prospects.
(2) imidazoles alginate ionic liquid belongs to the crossing domain of natural polymer and ionic liquid, is ionic liquid The impressive progress of body industrial applications.
(3) this synthetic method raw material is easy preparation, and cost is relatively low；Reaction condition and process green, nonpollution environment and The substance of harmful to human generates；Synthetic method is simple, and products pure no coupling product, purification process is simple, is suitble to high-volume scale Production.
(4) imidazoles alginate ionic liquid have tempting application prospect, especially pharmaceutical carrier, water tariff collection, The fields such as heavy metal ion adsorbed and functional polymer preparation have important application potentiality.
Specific embodiment
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention Rather than it limits the scope of the invention.In addition, it should also be understood that, after having read teaching content of the present invention, those skilled in the art The present invention can be made various changes or modifications, such equivalent forms are equally fallen within defined by the application the appended claims Range.
Example 1:1,3- methylimidazole alginate ionic liquid [C1mim][Alg].2.26g will be contained The aqueous isopropanol of (0.020mol) 1,3- methylimidazole hydroxide and the brand-new for containing 3.52g (0.020mol) alginic acid Aqueous solution (solvent swelling state) mixing carries out centrifugal treating to it and takes out clear liquid after stirring 1 hour at room temperature, after removing solvent Obtain 1,3- methylimidazole alginate ionic liquid [C1Mim] [Alg], it is light yellow solid at room temperature.
Example 2:1- methyl -3- ethyl imidazol(e) alginate ionic liquid [C2mim][Alg].2.56g will be contained The aqueous isopropanol of (0.020mol) 1- methyl -3- ethyl imidazol(e) hydroxide with containing 3.52g (0.020mol) alginic acid Brand-new aqueous solution (solvent swelling state) mixing carries out centrifugal treating to it and takes out clear liquid after stirring 1 hour at room temperature, removes molten 1- methyl -3- ethyl imidazol(e) alginate ionic liquid [C is obtained after agent2Mim] [Alg], it is light yellow solid at room temperature.
Example 3:1- methyl -3- butyl imidazole alginate ionic liquid [C4mim][Alg].3.12g will be contained The aqueous isopropanol of (0.020mol) 1- methyl -3- butyl imidazole hydroxide with containing 3.52g (0.022mol) alginic acid Brand-new aqueous solution (solvent swelling state) mixing carries out centrifugal treating to it and takes out clear liquid after stirring 2 hours at room temperature, removes molten 1- methyl -3- butyl imidazole alginate ionic liquid [C is obtained after agent4Mim] [Alg], it is light yellow solid at room temperature.
Example 4:1- methyl -3- hexyl imidazolium alginate ionic liquid [C6mim][Alg].3.69g will be contained The aqueous isopropanol of (0.020mol) 1- methyl -3- hexyl imidazolium hydroxide with containing 3.52g (0.022mol) alginic acid Brand-new aqueous solution (solvent swelling state) mixing carries out centrifugal treating to it and takes out clear liquid after stirring 4 hours at room temperature, removes molten 1- methyl -3- hexyl imidazolium alginate ionic liquid [C is obtained after agent6Mim] [Alg], it is thick pale yellow at room temperature Liquid.
Example 5:1- methyl -3- octylimidazole alginate ionic liquid [C8mim][Alg].4.25g will be contained The aqueous isopropanol of (0.020mol) 1- methyl -3- octylimidazole hydroxide with containing 3.52g (0.022mol) alginic acid Brand-new aqueous solution (solvent swelling state) mixing carries out centrifugal treating to it and takes out clear liquid after stirring 8 hours at room temperature, removes molten 1- methyl -3- octylimidazole alginate ionic liquid [C is obtained after agent8Mim] [Alg], it is thick pale yellow at room temperature Liquid.
Example 6:1- methyl -3- decyl imidazoles alginate ionic liquid [C10mim][Alg].4.81g will be contained The aqueous isopropanol of (0.020mol) 1- methyl -3- decyl imidazolium hydroxide with containing 3.52g (0.020mol) alginic acid Brand-new aqueous solution (solvent swelling state) mixing carries out centrifugal treating to it and takes out clear liquid after stirring 12 hours at room temperature, removes molten 1- methyl -3- decyl imidazoles alginate ionic liquid [C is obtained after agent10Mim] [Alg], it is clear yellow viscous liquid at room temperature Body.
Example 7:1- methyl -3- dodecyl imidazole alginate ionic liquid [C12mim][Alg].5.37g will be contained The aqueous isopropanol of (0.020mol) 1- methyl -3- dodecyl imidazole hydroxide with contain 3.87g (0.022mol) seaweed Brand-new aqueous solution (solvent swelling state) mixing of acid carries out centrifugal treating to it and takes out clear liquid, remove after stirring 24 hours at room temperature 1- methyl -3- dodecyl imidazole alginate ionic liquid [C is obtained after removing solvent12Mim] [Alg], it is yellow at room temperature Color solid.
Example 8:1- methyl -3- myristyl imidazoles alginate ionic liquid [C14mim][Alg].5.93g will be contained The aqueous isopropanol of (0.020mol) 1- methyl -3- myristyl imidazolium hydroxide with contain 3.87g (0.022mol) seaweed Brand-new aqueous solution (solvent swelling state) mixing of acid carries out centrifugal treating to it and takes out clear liquid, remove after stirring 24 hours at room temperature 1- methyl -3- myristyl imidazoles alginate ionic liquid [C is obtained after removing solvent14Mim] [Alg], it is yellow at room temperature Color solid.
Example 9:1- methyl -3- cetyl imidazoles alginate ionic liquid [C16mim][Alg].6.49g will be contained The aqueous isopropanol of (0.020mol) 1- methyl -3- cetyl imidazolium hydroxide with contain 3.87g (0.022mol) seaweed The brand-new aqueous solution (solvent swelling state) of acid mixes, and after stirring 48 hours at 75 DEG C, carries out centrifugal treating to it and takes out clear liquid, remove 1- methyl -3- cetyl imidazoles alginate ionic liquid [C is obtained after removing solvent16Mim] [Alg], it is yellow at room temperature Color solid.
Example 10:1- methyl -3- octadecyl imidazoles alginate ionic liquid [C18mim][Alg].7.05g will be contained The aqueous isopropanol of (0.020mol) 1- methyl -3- octadecyl imidazolium hydroxide with contain 3.87g (0.022mol) seaweed The brand-new aqueous solution (solvent swelling state) of acid mixes, and after stirring 72 hours at 75 DEG C, carries out centrifugal treating to it and takes out clear liquid, remove 1- methyl -3- octadecyl imidazoles alginate ionic liquid [C is obtained after removing solvent18Mim] [Alg], it is yellow at room temperature Color solid.
Example 11:1- methyl -3- allyl imidazole alginate ionic liquid [Amim] [Alg].2.80g will be contained The aqueous isopropanol of (0.020mol) 1- methyl -3- allyl imidazole hydroxide with contain 3.52g (0.022mol) alginic acid Brand-new aqueous solution (solvent swelling state) mixing, at room temperature stir 8 hours after, centrifugal treating is carried out to it and takes out clear liquid, remove 1- methyl -3- allyl imidazole alginate ionic liquid [Amim] [Alg] is obtained after solvent, is that yellow is solid at room temperature Body.
Example 12:1- methyl -3- acetonyl imidazoles alginate ionic liquid [MeCOCH2mim][Alg].It will contain The aqueous isopropanol of 3.12g (0.020mol) 1- methyl -3- acetonyl imidazolium hydroxide with containing 3.87g (0.022mol) sea The brand-new aqueous solution (solvent swelling state) of alginic acid mixes, and after stirring 24 hours at room temperature, carries out centrifugal treating to it and takes out clear liquid, 1- methyl -3- acetonyl imidazoles alginate ionic liquid [MeCOCH is obtained after removing solvent2Mim] [Alg], at room temperature It is light yellow solid.
Example 13:1- methyl -3- cyanoethyl imidazoles alginate ionic liquid [NCCH2mim][Alg].2.78g will be contained The aqueous isopropanol of (0.020mol) 1- methyl -3- cyanoethyl imidazolium hydroxide with contain 3.87g (0.022mol) alginic acid Brand-new aqueous solution (solvent swelling state) mixing, at room temperature stir 24 hours after, centrifugal treating is carried out to it and takes out clear liquid, remove It is formed after solvent and obtains 1- methyl -3- cyanoethyl imidazoles alginate ionic liquid [NCCH2Mim] [Alg], it is at room temperature Light yellow solid.
Example 14:1- methyl -3- ethyl acetate base imidazoles alginate ionic liquid [CH3CH2OOCCH2mim][Alg]。 By the aqueous isopropanol containing 3.72g (0.020mol) 1- methyl -3- ethyl acetate base imidazolium hydroxide and contain 3.87g The brand-new aqueous solution (solvent swelling state) of (0.022mol) alginic acid mixes, and after stirring 24 hours at room temperature, carries out at centrifugation to it Clear liquid is managed and taken out, after removing solvent, obtains 1- methyl -3- ethyl acetate base imidazoles alginate ionic liquid [CH3CH2OOCCH2Mim] [Alg], it is yellow viscous liquid at room temperature.
Example 15:1- methyl -3- acetenyl imidazoles alginate ionic liquid [HCCH2mim][Alg].2.52g will be contained The aqueous isopropanol of (0.020mol) 1- methyl -3- acetenyl imidazolium hydroxide with contain 3.87g (0.022mol) alginic acid Brand-new aqueous solution (solvent swelling state) mixing, at room temperature stir 48 hours after, centrifugal treating is carried out to it and takes out clear liquid, remove 1- methyl -3- acetenyl imidazoles alginate ionic liquid [HCCH is obtained after solvent2Mim] [Alg], it is yellow at room temperature Thick liquid.
Example 16:1- ethyl -3- butyl imidazole alginate ionic liquid [C2C4im][Alg].3.41g will be contained The aqueous isopropanol of (0.020mol) 1- ethyl -3- butyl imidazole hydroxide with containing 3.87g (0.022mol) alginic acid Brand-new aqueous solution (solvent swelling state) mixing carries out centrifugal treating to it and takes out clear liquid after stirring 12 hours at room temperature, removes molten 1- ethyl -3- butyl imidazole alginate ionic liquid [C is obtained after agent2C4Im] [Alg], it is yellow solid at room temperature.
Example 17:1- propyl -3- butyl imidazole alginate ionic liquid [C3C4im][Alg].3.69g will be contained The aqueous isopropanol of (0.020mol) 1- propyl -3- butyl imidazole hydroxide with containing 3.87g (0.022mol) alginic acid Brand-new aqueous solution (solvent swelling state) mixing carries out centrifugal treating to it and takes out clear liquid after stirring 12 hours at room temperature, removes molten 1- propyl -3- butyl imidazole alginate ionic liquid [C is obtained after agent3C4Im] [Alg], it is yellow solid at room temperature.
Example 18:1,2- dibutyl imidazoles alginate ionic liquid [C4C4im][Alg].3.97g will be contained The aqueous isopropanol of (0.020mol) 1,2- dibutyl imidazolium hydroxide and the brand-new for containing 3.87g (0.022mol) alginic acid Aqueous solution (solvent swelling state) mixing carries out centrifugal treating to it and takes out clear liquid after stirring 24 hours at room temperature, after removing solvent Obtain 1,2- dibutyl imidazoles alginate ionic liquid [C4C4Im] [Alg], it is light yellow solid at room temperature.
Example 19:1- butyl -3- amyl imidazoles alginate ionic liquid [C4C5im][Alg].4.25g will be contained The aqueous isopropanol of (0.020mol) 1- butyl -3- amyl imidazolium hydroxide with containing 3.87g (0.022mol) alginic acid Brand-new aqueous solution (solvent swelling state) mixing carries out centrifugal treating to it and takes out clear liquid after stirring 24 hours at room temperature, removes molten 1- butyl -3- amyl imidazoles alginate ionic liquid [C is obtained after agent4C5Im] [Alg], it is light yellow solid at room temperature.
Example 20:1- butyl -3- hexyl imidazolium alginate ionic liquid [C4C6mim][Alg].4.53g will be contained The aqueous isopropanol of (0.020mol) 1- butyl -3- hexyl imidazolium hydroxide with containing 3.87g (0.022mol) alginic acid Brand-new aqueous solution (solvent swelling state) mixing carries out centrifugal treating to it and takes out clear liquid after stirring 24 hours at room temperature, removes molten 1- butyl -3- hexyl imidazolium alginate ionic liquid [C is obtained after agent4C6Mim] [Alg], it is yellow solid at room temperature.
Example 21:1,2,3- tri-methylimidazolium alginate ionic liquid [C1mmim][Alg].2.56g will be contained The aqueous isopropanol of (0.020mol) 1,2,3- tri-methylimidazolium hydroxide with it is new containing 3.87g (0.022mol) alginic acid Aqueous solution (solvent swelling state) mixing processed carries out centrifugal treating to it and takes out clear liquid after stirring 12 hours at room temperature, removes solvent After obtain 1,2,3- tri-methylimidazolium alginate ionic liquid [C1Mmim] [Alg], it is light yellow solid at room temperature.
Example 22:1,2- dimethyl -3- ethyl imidazol(e) alginate ionic liquid [C2mmim][Alg].2.84g will be contained The aqueous isopropanol of (0.020mol) 1,2- dimethyl -3- ethyl imidazol(e) hydroxide with contain 3.87g (0.022mol) seaweed Brand-new aqueous solution (solvent swelling state) mixing of acid carries out centrifugal treating to it and takes out clear liquid, remove after stirring 12 hours at room temperature 1,2- dimethyl -3- ethyl imidazol(e) alginate ionic liquid [C is obtained after removing solvent2Mmim] [Alg], it is yellow at room temperature Color solid.
Example 23:1,2- dimethyl -3- propyl imidazole alginate ionic liquid [C3mmim][Alg].3.12g will be contained The aqueous isopropanol of (0.020mol) 1,2-dimethyl-3- propyl imidazole hydroxide with contain 3.87g (0.022mol) seaweed Brand-new aqueous solution (solvent swelling state) mixing of acid carries out centrifugal treating to it and takes out clear liquid, remove after stirring 24 hours at room temperature 1,2- dimethyl -3- propyl imidazole alginate ionic liquid [C is obtained after removing solvent3Mmim] [Alg], it is yellow at room temperature Color solid.
Example 24:1,2- dimethyl -3- butyl imidazole alginate ionic liquid [C4mmim][Alg].3.41g will be contained The aqueous isopropanol of (0.020mol) 1,2- dimethyl -3- butyl imidazole hydroxide with contain 3.87g (0.022mol) seaweed Brand-new aqueous solution (solvent swelling state) mixing of acid carries out centrifugal treating to it and takes out clear liquid, remove after stirring 24 hours at room temperature 1,2- dimethyl -3- butyl imidazole alginate ionic liquid [C is obtained after removing solvent4Mmim] [Alg], it is yellow at room temperature Color solid.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art For member, without departing from the technical principles of the invention, several improvements and modifications, these improvements and modifications can also be made Also it should be regarded as protection scope of the present invention.

Claims (7)

1. a kind of imidazoles alginate ionic liquid, it is characterised in that: the structural formula of the imidazoles alginate ion are as follows:
Wherein R1、R3For H atom, alkyl or substituted hydrocarbon radical；R2For H atom or methyl；[Alg]—For seaweed acid radical anion；
The alkyl is the alkyl that carbon chain lengths are 1~20；
The substituted hydrocarbon radical is methyl, ethyl, propyl, butyl, amyl, hexyl, octyl, decyl, dodecyl, the tetradecane Base, cetyl, octadecyl, allyl, acetonyl, cyanoethyl, ethyl acetate base, any one in acetenyl.
2. a kind of synthetic method of imidazoles alginate ionic liquid, which comprises the following steps: by imidazoles hydrogen Oxide is mixed with brand-new alginic acid according to the molar ratio of 1:1~1.1 in a solvent, is stirred evenly, after reaction centrifuging and taking Clear liquid out, and solvent is removed, imidazoles alginate ionic liquid can be obtained.
3. the synthetic method of imidazoles alginate ionic liquid according to claim 2, it is characterised in that: solvent can To select water, dichloroethanes, any one or a few in isopropanol.
4. the synthetic method of imidazoles alginate ionic liquid according to claim 2, it is characterised in that: described Solvent is water or isopropanol.
5. the synthetic method of imidazoles alginate ionic liquid according to claim 2, it is characterised in that: reaction temperature Degree is room temperature to 75 DEG C.
6. the synthetic method of imidazoles alginate ionic liquid according to claim 5, it is characterised in that: reaction temperature Degree is room temperature.
7. the synthetic method of imidazoles alginate ionic liquid according to claim 2, it is characterised in that: in solvent Middle mixing, the time for stirring evenly and reacting is 1~72 hour.
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