CN101492423A - Method for preparing achromatic imidazole ionic liquids - Google Patents
Method for preparing achromatic imidazole ionic liquids Download PDFInfo
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- CN101492423A CN101492423A CNA2009100666204A CN200910066620A CN101492423A CN 101492423 A CN101492423 A CN 101492423A CN A2009100666204 A CNA2009100666204 A CN A2009100666204A CN 200910066620 A CN200910066620 A CN 200910066620A CN 101492423 A CN101492423 A CN 101492423A
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Abstract
The invention aims at providing a method for preparing colorless imidazole ion liquid. The colorless imidazole ion liquid is 1-alkyl-3-methyl imidazole bromine, and a general formula of the ion liquid is as above. The preparation method uses water as solvent, thereby reducing the use of organic solvent and achieving the goal of being friendly to the environment. Under the protection of nitrogen, a reaction product is dissolved in water to remove brominated alkane which does not react at an underlayer for recycling; and the water in the reaction product and the residual brominated alkane are removed by decompressing and distilling to obtain the colorless 1-alkyl-3-methyl imidazole bromine ion liquid. A reaction mixture is colorless during the whole reaction process, the obtained product of the imidazole ion liquid is also colorless, and subsequent decolorization and purification treatment is not required, thereby greatly reducing the nondeterminacy and the limit of the ion liquid in the application.
Description
Technical field
The present invention relates to a kind of preparation method of achromatic imidazole ionic liquids.
Background technology
Ionic liquid is as environment amenable solvent, fields such as separation, reaction, electrochemistry have been widely used at present, comprise 1,3-dialkylimidazolium salt has the irreplaceable advantage of other organic solvents at interior ionic liquid. but ion liquid building-up process often is not green, often will use the poisonous organic solvents that environment had pollution such as toluene in preparation process.Most of ionic liquid should be colourless in theory, but has color when synthetic.Through the research in twoth century, have the reason of color for ionic liquid, people do not provide clear and definite explanation yet.For example, be often used as 1 of synthetic other ionic liquid raw materials, 3-dialkylimidazolium halogenide, although think that by analytical procedures such as nuclear-magnetism, mass spectrum, chromatogram sign its purity is very high, it usually is yellow or dark-brown.The ionic liquid that has a color is known from experience and is brought uncertainty for its application at aspects such as photochemistry, original position ultraviolets, even can limit its application in these areas.Therefore, the whole bag of tricks is used to solve pollution problem and the ion liquid color problem in the ionic liquid building-up process.For example, for fear of with an organic solvent, microwave assisting method (M.Deetlefs, K.R.Seddon.Improved preparations of ionic liquidsusing microwave irradiation.Green Chem., 2003,5,181-186) with ultrasonic auxiliary law (V.V.Namboodiri and R.S.Varma.Solvent-FreeSonochemical Preparation of Ionic Liquids.Org.Lett., 2002,4,3161-3163.) be used to solvent-free ionic liquid and synthesize.In order to prepare colourless ionic liquid, people often take some precautionary measures or purify (M.J.Earle after preparations in preparation process, C.M.Gordon, N.V.Plechkova, K.R.Seddon and T.Welton.Decolorization of Ionic Liquids for Spectroscopy.Anal.Chem., 2007,79,758-764.).Above method operation more complicated, the cost height can not satisfy the large-scale application requirement, and people are still trying to explore a kind of simple, economic, gentle, environment amenable colourless ion liquid method.
Summary of the invention
The preparation method who the purpose of this invention is to provide a kind of achromatic imidazole ionic liquids, described achromatic imidazole ionic liquids is 1-alkyl-3-Methylimidazole bromine salt, this ion liquid general formula is:
A kind of preparation method of achromatic imidazole ionic liquids, be with water as solvent, reduced the use of organic solvent, reached environment amenable purpose.And the most important thing is that reaction mixture is colourless in entire reaction course, the products therefrom glyoxaline ion liquid also is colourless, does not need subsequent decolorization and purification treatment, has reduced the uncertain and restriction of ionic liquid in application facet widely.
The purpose of this invention is to provide the as follows of a kind of achromatic imidazole ionic liquids:
Its reaction scheme method is:
Preparation method's step and condition are as follows: with volume ratio is that 1: 1～6: 1 bromoalkane and 1-Methylimidazole mix, and the chemical formula of described bromoalkane is C
nH
2n+1Br, wherein 2≤n≤6; In mixture, add aqueous solvent; the volume ratio of water and said mixture is 0.2: 1～2: 1; under nitrogen protection; 40 ℃～100 ℃ backflow 12h～48h; reaction product is dissolved in water; the unreacted bromo alkane of lower floor is shifted out recycle, and water in the reaction product and remaining bromo alkane are removed at 40 ℃～100 ℃ underpressure distillation 4h～10h, obtain a kind of achromatic imidazole ionic liquids.
Beneficial effect: the purpose of this invention is to provide a kind of preparation method of achromatic imidazole ionic liquids, described achromatic imidazole ionic liquids is 1-alkyl-3-Methylimidazole bromine salt method.This preparation method be with water as solvent, reduced the use of organic solvent, reached environment amenable purpose.And the most important thing is that reaction mixture is colourless in entire reaction course, the products therefrom glyoxaline ion liquid also is colourless, does not need subsequent decolorization and purification treatment, has reduced the uncertain and restriction of ionic liquid in application facet widely.
Embodiment
Embodiment 1:
When n=2, bromo alkane is monobromethane.With volume ratio is that 1: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted monobromethane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 2:
When n=2, bromo alkane is monobromethane.With volume ratio is that 3: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted monobromethane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 3:
When n=2, bromo alkane is monobromethane.With volume ratio is that 6: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted monobromethane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 4:
When n=2, bromo alkane is monobromethane.With volume ratio is that 1: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 1.2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted monobromethane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 5:
When n=2, bromo alkane is monobromethane.With volume ratio is that 1: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted monobromethane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 6:
When n=2, bromo alkane is monobromethane.With volume ratio is that 1: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 80 ℃, backflow 12h.Remove the unreacted monobromethane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 7:
When n=2, bromo alkane is monobromethane.With volume ratio is that 1: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 100 ℃, backflow 12h.Remove the unreacted monobromethane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 8:
When n=2, bromo alkane is monobromethane.With volume ratio is that 1: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 100 ℃, backflow 24h.Remove the unreacted monobromethane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 9:
When n=2, bromo alkane is monobromethane.With volume ratio is that 1: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 100 ℃, backflow 48h.Remove the unreacted monobromethane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 10:
When n=2, bromo alkane is monobromethane.With volume ratio is that 1: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 100 ℃, backflow 48h.Remove the unreacted monobromethane of lower floor, 100 ℃ of underpressure distillation 10h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 11:
When n=2, bromo alkane is monobromethane.With volume ratio is that 1: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 100 ℃, backflow 48h.Remove the unreacted monobromethane of lower floor, 80 ℃ of underpressure distillation 10h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 12:
When n=2, bromo alkane is monobromethane.With volume ratio is that 1: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 100 ℃, backflow 48h.Remove the unreacted monobromethane of lower floor, 80 ℃ of underpressure distillation 6h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 13:
When n=2, bromo alkane is monobromethane.With volume ratio is that 3: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 100 ℃, backflow 48h.Remove the unreacted monobromethane of lower floor, 40 ℃ of underpressure distillation 4h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 14:
When n=2, bromo alkane is monobromethane.With volume ratio is that 6: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 80 ℃, backflow 48h.Remove the unreacted monobromethane of lower floor, 40 ℃ of underpressure distillation 4h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 15:
When n=2, bromo alkane is monobromethane.With volume ratio is that 3: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 1.2: 1, under nitrogen protection 80 ℃, backflow 48h.Remove the unreacted monobromethane of lower floor, 40 ℃ of underpressure distillation 6h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 16:
When n=2, bromo alkane is monobromethane.With volume ratio is that 6: 1 monobromethane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 1.2: 1, under nitrogen protection 100 ℃, backflow 48h.Remove the unreacted monobromethane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted monobromethane in the product, colourless 1-ethyl-3-Methylimidazole bromine salt.
Embodiment 17:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 1: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted bromination of n-butane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 18:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 3: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted bromination of n-butane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 19:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 6: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted bromination of n-butane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 20:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 6: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted bromination of n-butane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 21:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 1: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 1.2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted bromination of n-butane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 22:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 1: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted bromination of n-butane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 23:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 1: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 65 ℃, backflow 12h.Remove the unreacted bromination of n-butane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 24:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 1: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 100 ℃, backflow 12h.Remove the unreacted bromination of n-butane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 25:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 1: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 40 ℃, backflow 24h.Remove the unreacted bromination of n-butane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 26:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 1: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 40 ℃, backflow 48h.Remove the unreacted bromination of n-butane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 27:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 1: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 65 ℃, backflow 12h.Remove the unreacted bromination of n-butane of lower floor, 80 ℃ of underpressure distillation 4h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 28:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 1: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 65 ℃, backflow 12h.Remove the unreacted bromination of n-butane of lower floor, 100 ℃ of underpressure distillation 6h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 29:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 3: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 1.2: 1, under nitrogen protection 65 ℃, backflow 12h.Remove the unreacted bromination of n-butane of lower floor, 80 ℃ of underpressure distillation 6h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 30:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 6: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 1.2: 1, under nitrogen protection 65 ℃, backflow 12h.Remove the unreacted bromination of n-butane of lower floor, 80 ℃ of underpressure distillation 6h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 31:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 6: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 65 ℃, backflow 12h.Remove the unreacted bromination of n-butane of lower floor, 100 ℃ of underpressure distillation 10h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 32:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 3: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 65 ℃, backflow 24h.Remove the unreacted bromination of n-butane of lower floor, 100 ℃ of underpressure distillation 10h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 33:
When n=4, bromo alkane is bromination of n-butane.With volume ratio is that 1: 1 bromination of n-butane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 65 ℃, backflow 12h.Remove the unreacted bromination of n-butane of lower floor, 80 ℃ of underpressure distillation 10h remove water and the unreacted bromination of n-butane in the product, colourless 1-butyl-3-Methylimidazole bromine salt.
Embodiment 34:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 1: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted bromo normal hexane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 35:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 3: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted bromo normal hexane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 36:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 6: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted bromo normal hexane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 37:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 1: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 1.2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted bromo normal hexane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 38:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 1: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted bromo normal hexane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 39:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 1: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 65 ℃, backflow 12h.Remove the unreacted bromo normal hexane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 40:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 1: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 0.2: 1, under nitrogen protection 100 ℃, backflow 12h.Remove the unreacted bromo normal hexane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 41:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 1: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 1.2: 1, under nitrogen protection 40 ℃, backflow 24h.Remove the unreacted bromo normal hexane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 42:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 1: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 1.2: 1, under nitrogen protection 40 ℃, backflow 48h.Remove the unreacted bromo normal hexane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 43:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 3: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 1.2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted bromo normal hexane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 44:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 3: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted bromo normal hexane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 45:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 6: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 1.2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted bromo normal hexane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 46:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 6: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 40 ℃, backflow 12h.Remove the unreacted bromo normal hexane of lower floor, 40 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 47:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 3: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 1.2: 1, under nitrogen protection 100 ℃, backflow 12h.Remove the unreacted bromo normal hexane of lower floor, 40 ℃ of underpressure distillation 6h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 48:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 1: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 1.2: 1, under nitrogen protection 100 ℃, backflow 12h.Remove the unreacted bromo normal hexane of lower floor, 100 ℃ of underpressure distillation 6h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 49:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 6: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 1.2: 1, under nitrogen protection 100 ℃, backflow 24h.Remove the unreacted bromo normal hexane of lower floor, 80 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 50:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 6: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 65 ℃, backflow 48h.Remove the unreacted bromo normal hexane of lower floor, 100 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 51:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 6: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 1.2: 1, under nitrogen protection 65 ℃, backflow 24h.Remove the unreacted bromo normal hexane of lower floor, 100 ℃ of underpressure distillation 6h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Embodiment 52:
When n=6, bromo alkane is the bromo normal hexane.With volume ratio is that 1: 1 bromo normal hexane and 1-Methylimidazole mix, to wherein adding aqueous solvent, and the volume ratio of water and said mixture 2: 1, under nitrogen protection 100 ℃, backflow 48h.Remove the unreacted bromo normal hexane of lower floor, 100 ℃ of underpressure distillation 10h remove water and the unreacted bromo normal hexane in the product, colourless 1-hexyl-3-Methylimidazole bromine salt.
Claims (1)
1. the preparation method who the purpose of this invention is to provide a kind of achromatic imidazole ionic liquids, described achromatic imidazole ionic liquids is 1-alkyl-3-Methylimidazole bromine salt, this ion liquid general structure is:
The reaction scheme method of this method is:
Preparation method's step and condition are as follows: with volume ratio is that 1: 1～6: 1 bromoalkane and 1-Methylimidazole mix, and the chemical formula of described bromoalkane is C
nH
2n+1Br, wherein 2≤n≤6; In mixture, add aqueous solvent; the volume ratio of water and said mixture is 0.2: 1～2: 1; under nitrogen protection; 40 ℃～100 ℃ backflow 12h～48h; reaction product is dissolved in water; the unreacted bromo alkane of lower floor is shifted out recycle, and water in the reaction product and remaining bromo alkane are removed at 40 ℃～100 ℃ underpressure distillation 4h～10h, obtain a kind of achromatic imidazole ionic liquids.
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| CNA2009100666204A CN101492423A (en) | 2009-03-12 | 2009-03-12 | Method for preparing achromatic imidazole ionic liquids |
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| CN102603644A (en) * | 2012-01-19 | 2012-07-25 | 林州市科能材料科技有限公司 | Production method of alkylimidazole ionic liquid |
| WO2013168145A1 (en) | 2012-05-10 | 2013-11-14 | Bromine Compounds Ltd. | Additives for zinc-bromine membraneless flow cells |
| WO2014122641A1 (en) | 2013-02-07 | 2014-08-14 | Bromine Compounds Ltd. | Processes for preparing l-alkyl-3-alkyl-pyridinium bromide and uses thereof as additives in electrochemical cells |
| US9905874B2 (en) | 2011-09-22 | 2018-02-27 | Bromine Compounds Ltd. | Additives for hydrogen/bromine cells |
| CN109199884A (en) * | 2018-10-12 | 2019-01-15 | 辽宁石化职业技术学院 | A kind of ion liquid type coloring agent |
| CN109289778A (en) * | 2018-10-12 | 2019-02-01 | 辽宁石化职业技术学院 | A kind of active carbon adsorption material of novel load glyoxaline ion liquid |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US9905874B2 (en) | 2011-09-22 | 2018-02-27 | Bromine Compounds Ltd. | Additives for hydrogen/bromine cells |
| CN102603644A (en) * | 2012-01-19 | 2012-07-25 | 林州市科能材料科技有限公司 | Production method of alkylimidazole ionic liquid |
| WO2013168145A1 (en) | 2012-05-10 | 2013-11-14 | Bromine Compounds Ltd. | Additives for zinc-bromine membraneless flow cells |
| US9722272B2 (en) | 2012-05-10 | 2017-08-01 | Bromine Compounds Ltd. | Additives for zinc-bromine membraneless flow cells |
| WO2014122641A1 (en) | 2013-02-07 | 2014-08-14 | Bromine Compounds Ltd. | Processes for preparing l-alkyl-3-alkyl-pyridinium bromide and uses thereof as additives in electrochemical cells |
| US9722281B2 (en) | 2013-02-07 | 2017-08-01 | Bromine Compounds Ltd. | Processes for preparing 1-alkyl-3-alkyl-pyridinium bromide and uses thereof as additives in electrochemical cells |
| CN109199884A (en) * | 2018-10-12 | 2019-01-15 | 辽宁石化职业技术学院 | A kind of ion liquid type coloring agent |
| CN109289778A (en) * | 2018-10-12 | 2019-02-01 | 辽宁石化职业技术学院 | A kind of active carbon adsorption material of novel load glyoxaline ion liquid |
| CN114950075A (en) * | 2022-04-12 | 2022-08-30 | 北京化工大学 | Ionic liquid agent for treating benzene series VOCs waste gas and absorption process |
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