CN102010283A - Method for preparing anion chiral ionic liquid - Google Patents

Method for preparing anion chiral ionic liquid Download PDF

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CN102010283A
CN102010283A CN2010105415262A CN201010541526A CN102010283A CN 102010283 A CN102010283 A CN 102010283A CN 2010105415262 A CN2010105415262 A CN 2010105415262A CN 201010541526 A CN201010541526 A CN 201010541526A CN 102010283 A CN102010283 A CN 102010283A
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chiral
salt
ionic liquids
ionic liquid
solubility
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CN2010105415262A
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吴建一
宗乾收
屠晓华
缪程平
闻立新
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嘉兴学院
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Abstract

The invention discloses a method for preparing anion chiral ionic liquid, which comprises the following steps of: reacting chiral carboxylate with a halogenated nitrogen heterocyclic salt in an organic solvent to generate the anion chiral ionic liquid and an inorganic alkali metal halogenated salt; and removing the halogenated salt through separation to obtain the anion chiral ionic liquid, wherein the minimum ratio is selected by measuring the dissolubility of the chiral carboxylate and the halogenated salt in the organic solvent in advance to obtain ratios, so the exchange temperature is determined, and the chiral carboxylate reacts with the halogenated nitrogen heterocyclic salt in the organic solvent at the temperature. The method is used for synthesizing the anion chiral ionic liquid by using a dissolubility ratio method. Because an appropriate temperature is selected, and the halogenated salt generated in the reaction has very low dissolubility in the organic solvent, the halogenated salt can be separated and removed easily to obtain the anion chiral ionic liquid with high purity.

Description

一种制备阴离子手性离子液体的方法 A method of anionic chiral ionic liquids prepared

技术领域 FIELD

[0001] 本发明涉及一种离子液体的制备方法,一种制备阴离子手性离子液体的方法。 [0001] The present invention relates to a method for preparing an ionic liquid, a method anionic chiral ionic liquids prepared. 背景技术 Background technique

[0002] 离子液体是一类含有机官能团熔融盐,离子液体可以引进各种官能团,实现离子液体功能化来满足特定的需求。 [0002] Ionic liquids are a class of functional group-containing molten salt, an ionic liquid can introduce various functional groups, to realize the function of ionic liquids to meet specific needs. 将手性有机小分子嫁接到离子液体得到手性离子液, 成为手性催化剂或手性溶剂。 The chiral organic molecules grafted to ionic liquids, chiral ionic liquids become a chiral catalyst or a chiral solvent. 手性有机小分子嫁接离子液体以共价键连接的,成为阳离子手性离子液体;以离子键连接的,则成为阴离子手性离子液体。 Chiral ionic liquids grafted small organic molecules covalently linked, to a cationic chiral ionic liquids; ionically linked, anionic become chiral ionic liquids. 阴离子手性离子液体是一类应用性强的新型手性催化剂。 Anionic chiral ionic liquids are a novel class of applications strong chiral catalyst.

[0003] 目前有文献报道酸碱中和法合成20种氨基酸为阴离子的手性离子液体OhnoCT. Am.Chem.Soc.[J], 2005,127(8) : 2398-2399.)和手性离子液体1-丁基-3-甲基-咪唑-L-乳酸盐的合成Sdeeon (Green Chem.[J],1999,1:232.)。 [0003] It has been reported that the acid-base and 20 amino acids were synthesized as chiral ionic liquids OhnoCT anion Am.Chem.Soc [J], 2005,127 (8):... 2398-2399) and chiral ionic liquid 1-butyl-3-methyl - imidazole -L- Sdeeon lactate synthesis (Green Chem [J], 1999,1: 232..). 酸碱中和合成手性离子液体时,可利用中和时产生水分离得到较纯的手性离子液体,但应用范围有一定的局限性;而Sdeeon合成的手性离子液体1-丁基-3-甲基-咪唑-L-乳酸盐纯度无法了解,没有较好的纯度的手性离子液体也就无法了解该物质的比旋光度等物理参数。 Acid synthesis and chiral ionic liquids, may be generated when using water and isolated in relatively pure chiral ionic liquids, but the scope of application has some limitations; and Sdeeon synthesized chiral ionic liquids 1-butyl - methyl - imidazole -L- lactate purity can not understand, there is no better purity chiral ionic liquids will not be able to understand the physical parameters of rotation than the other substances.

发明内容 SUMMARY

[0004] 本发明旨在提出一种制备手性离子液的方法,一种制备阴离子手性离子液体的方法,能得到纯度较高的手性离子液体。 [0004] The present invention is directed to a process for preparing chiral ionic liquid, a method of anionic chiral ionic liquids prepared with high purity can be obtained chiral ionic liquids.

[0005] 这种制备阴离子手性离子液体的方法是:通过测定手性羧酸盐和无机碱金属卤化盐在有机溶剂中的溶解度并得比值,选择最小的比值,从而确定反应温度,在此温度下将手性羧酸盐与卤代氮杂环盐在有机溶剂中反应,生成阴离子手性离子液体和卤化盐,再分离除去卤化盐得到阴离子手性离子液体。 [0005] This method of preparing an anionic chiral ionic liquids are: by measuring the solubility of the salts of chiral carboxylic acids and inorganic alkali metal halide salt in an organic solvent and have the ratio, selecting the minimum ratio, to determine the reaction temperature in this the temperature of the chiral salt with a halogenated carboxylic acid salts azetidin reaction in an organic solvent, anion generation chiral ionic liquids and halide salts, halide salts and then separated and removed to obtain an anionic chiral ionic liquids.

[0006] 本发明的方法是一种应用溶解度比值法合成阴离子手性离子液体的方法,由于选择了合适的温度,反应生成的卤化盐在有机溶剂中的溶解度很低,因而较易将卤化盐分离去除,并得到纯度较高的阴离子手性离子液体。 [0006] The method of the present invention is a process for the anionic synthetic chiral ionic liquids solubility ratio method an application, since the selection of the appropriate temperature, the resulting reaction halide salt solubility in organic solvents is very low, thus easier halide salt separated and removed, and the obtained high purity anionic chiral ionic liquids.

附图说明 BRIEF DESCRIPTION

[0007] 图1为NaCl与Na[RHPA]在甲醇中的溶解度; [0007] FIG. 1 is NaCl and Na [RHPA] The solubility in methanol;

[0008] 图2为NaCl与Na[RHPA]在甲醇溶剂中的溶解度之比; [0008] FIG. 2 is NaCl and Na [RHPA] ratio of the solubility of the methanol solvent;

[0009] 图3为KBr与K[PAL]在丙酮中的溶解度; [0009] FIG. 3 is a KBr and K [PAL] solubility in acetone;

[0010] 图4为KBr与K[PAL]在丙酮中的溶解度之比; [0010] FIG. 4 is a KBr and K [PAL] ratio of solubility in acetone;

[0011] 图5为NaCl与Na[RHPA]在甲醇中的溶解度; [0011] FIG. 5 is NaCl and Na [RHPA] The solubility in methanol;

[0012] 图6为NaCl与Na[RHPA]在甲酮中的溶解度之比; [0012] FIG. 6 is NaCl and Na [RHPA] A ratio of the solubility of the ketone;

[0013] 图7为KCl与K[PAL]在丙酮中的溶解度; [0013] FIG. 7 is KCl and K [PAL] solubility in acetone;

[0014] 图8为KCl与K[PAL]在丙酮中的溶解度之比。 [0014] FIG. 8 is KCl and K [PAL] ratio of solubility in acetone. 具体实施方式 Detailed ways

[0015] 本方法通过测定组成阴离子手性离子液体的阳离子和阴离子相应的盐在某有机溶剂中的溶解度,然后得到二种物质的溶解度比值,并绘出溶解度比值曲线,从曲线上找出溶解度比值最小时的温度作为该溶剂中进行离子交换的最合适的温度,使用手性羧酸盐与卤代氮杂环盐反应交换产生阴离子手性离子液体和卤化盐,通过分离除去卤化盐,得到阴离子手性离子液体。 [0015] The present method determine the composition of the chiral ionic liquids anionic cations and anions corresponding solubility in an organic solvent, then solubility ratio to give two kinds of materials, and draw ratio of the solubility curves, from the solubility curve to find the ratio of the minimum temperature of the most suitable temperature ion exchange as the solvent using a chiral salt with a halogenated carboxylic acid salts azetidin anion exchange generates chiral ionic liquids and halide salts, halide salts removed by separation to give anionic chiral ionic liquids.

[0016] 本方法中的手性有机羧酸盐是指: [0016] The present method of organic carboxylic acid salt of chiral means:

[0017] [0017]

R-(CH2)nI-COOM H R- (CH2) nI-COOM H

[0018] 式中R代表苯基、η= 1-3的自然数,Z代表氨基和羟基,M代表金属钠或钾。 [0018] wherein R represents a phenyl group, η = a natural number of 1-3, Z represents an amino group and a hydroxyl group, M for the metal sodium or potassium.

[0019] 卤代氮杂环离子液体指以下两种结构中之一种的物质: [0019] azetidin haloalkyl ionic liquid refers to a structure of the following two materials:

[0020] [0020]

场-CH3 Field -CH3

P ^ P ^

[0021 ] 式中R代表苄基或CH3 (CH2) η,(η = 3、4) ; X代表氯或溴。 [0021] wherein R represents a benzyl group or CH3 (CH2) η, (η = 3,4); X represents chlorine or bromine. [0022] 设所用的卤化盐在所用的溶剂中的溶解度为SMX,所用卤代氮杂环盐在此溶剂中的溶解度为Srqxjm,两者的比值为S',即S'= SMX/SRe(X)M。 Solubility [0022] provided the salt used halide solvent used is from SMX, the solubility of the halogenated azetidin salt in this solvent used is Srqxjm, the ratio between them is S ', i.e. S' = SMX / SRe ( X) M. 经实验测得S'的值和产物阴离子手性离子液体的纯度,并可建立产物的纯度与S'关系式如下所示: The experiment measured S 'values ​​and purity of the chiral ionic liquid anion product, and to establish the purity of the product S' relationship is as follows:

1 1 11

w w

[0023] , [0023],

r ο 、2 r ο, 2

S、 S,

network

C C

^[RCOOM]」 ^ [RCOOM]. "

1 + 1 +

[0024] 表示产物中手性离子液体的质量百分数,α是个常数,与分子量有关。 [0024] indicates a mass of the chiral ionic liquids percent product, [alpha] is a constant related to the molecular weight.

[0025] 由上述公式可知,产物中手性离子液体的纯度跟常数α和S'有关,在合适的温度和溶剂中寻找最小的S',可制得纯度较高的阴离子手性离子液体。 [0025] From the above equation, the product purity with chiral ionic liquids constants α and S 'is related to find a suitable temperature in the solvent and the smallest S', can be obtained with high purity anionic chiral ionic liquids. 当S'小于0.05时, 合成的产物纯度可以达98%以上。 When S 'is less than 0.05, purity of a synthesized product may be more than 98%. 因此,选择S'小于0.05的溶剂和温度将卤代氮杂环离子液与手性羧酸盐在有机溶剂中通过离子交换合成阴离子手性离子液体,可得到满意的结果。 Thus, selecting S 'of less than 0.05 and a temperature of the solvent halogenated ionic liquid nitrogen heterocycle salt with a chiral carboxylic acid in an organic solvent exchanged synthetic anionic ion by chiral ionic liquids, satisfactory results are obtained.

[0026] 这种通过测定无机盐与有机盐在有机溶剂中的溶解度,通过二种溶解度的比值及溶解度的比值与产物纯度的关系,测算出合成手性阴离子离子液体纯度,可在手性阴离子合成时在原料和反应参数的选择上应用。 [0026] Such inorganic and organic by measuring the solubility in an organic solvent in the salt, the ratio of two kinds of relationships by the solubility and solubility product purity ratio, measure the anion of the ionic liquid synthesis of chiral purity, chiral anion can be application of the choice of starting materials and reaction parameters of the synthesis.

[0027] 实施例1 [0027] Example 1

[0028] 制备1-苄基-3-甲基咪唑-(_) -2-羟基-4-苯丁酸盐 [0028] Preparation of 1-benzyl-3-methylimidazolium - (_) - 2-hydroxy-4-phenylbutyrate

[0029] (1)原料 [0029] (1) Raw material

[0030] (a)手性有机羧酸盐:选择(_) -2-羟基-4-苯丁酸钠(Na[RHPA]) (R =苯基、η [0030] (a) a chiral organic carboxylates: Select (_) -2-hydroxy-4-phenyl butyrate Sodium (Na [RHPA]) (R = phenyl, η

4=2、Z =羟基、M =钠) 4 = 2, Z = hydroxy, M = sodium)

[0031] (b)卤代氮杂环离子液体:选择氯化-1-苄基-3-甲基咪唑(R=苄基、X=氯) [0031] (b) halo azetidin ionic liquids: Select chloride imidazole 1-benzyl-3-methyl (R = benzyl, X = chloro)

[0032] (2)制备过程 [0032] (2) Preparation process

[0033] (a)参数选择:测定氯化钠和(R)_2-羟基-4-苯丁酸钠在乙醇中的溶解度,绘制15-65°C的溶解度曲线如图1,得到溶解度比值与温度的关系如图2,从中选择S'= 0.040,对应的反应温度为65°C,因此在该温度下进行反应,此时由公式⑴计算得到的理论纯度为98.9%。 [0033] (a) parameter selection: Determination of sodium chloride and (R) _2- hydroxy-4-Buphenyl solubility in ethanol, solubility curves plotted in FIG. 1 15-65 ° C, to give a ratio of solubility temperature relationship in FIG 2, select S '= 0.040, corresponding to the reaction temperature of 65 ° C, so the reaction was carried out at a temperature at this time is given by equation theoretical purity of 98.9% obtained ⑴.

[0034] (b)操作过程:在50ml三口烧瓶中加入乙醇20ml、氯化苄基_3_甲基咪唑2.08g(0.01mol)、(R) -2-羟基-4-苯丁酸钠2.02g(O.Olmol),在65°C下搅拌8h,过滤出氯化钠,蒸干乙醇,经过离心沉淀器将液体中的少量固体杂质去除,得到1-苄基-3-甲基咪唑-(-)-2-羟基-4-苯丁酸盐,经离子色谱测得纯度为98.4%。 [0034] (b) Procedure: Add 20ml of ethanol in 50ml three-necked flask, benzyltriethylammonium chloride _3_ methylimidazole 2.08g (0.01mol), (R) -2- hydroxy-4-phenyl butyrate Sodium 2.02 g (O.Olmol), stirred at 65 ° C 8h, sodium chloride was filtered off, ethanol evaporated to dryness, a small amount through centrifugation will remove solid impurities in the liquid, to give 1-benzyl-3-methylimidazolium - (-) - 2-hydroxy-4-phenylbutyrate, as measured by an ion chromatographic purity of 98.4%.

[0035] 实施例2 [0035] Example 2

[0036] 制备丁基吡啶-L-苯丙氨酸盐 [0036] Preparation butylpyridine -L- phenylalanine salt

[0037] (1)原料 [0037] (1) Raw material

[0038] (a)手性有机羧酸盐:选择L-苯丙氨酸钾(K[PAL]) (R =苯基、η = 1、Z =氨基、M=钾) [0038] (a) a chiral organic carboxylic acid salt: potassium benzene select L- phenylalanine (K [PAL]) (R = phenyl, η = 1, Z = amino, M = K)

[0039] (b)卤代氮杂环离子液体:选择溴化丁基吡啶([BP]Br) (R = 丁基、X =溴) [0039] (b) halo azetidin ionic liquids: select brominated butyl pyridine ([BP] Br) (R = butyl, X = bromine)

[0040] (2)制备过程 [0040] (2) Preparation process

[0041] (a)参数选择:测定溴化钾和L-苯丙氨酸钾在丙酮中的溶解度,绘制5-50°C 的溶解度曲线如图3,得到溶解度比值与温度的关系如图4,从中选择S'= 0.055,对应的反应温度为5°C,因此在该温度下进行反应,此时由公式⑴计算得到的理论纯度为99.3%。 [0041] (a) parameter selection: determine the solubility of potassium bromide and potassium L- phenylalanine in acetone, 5-50 ° C solubility curves plotted in FIG. 3, to give a ratio of the temperature dependence of the solubility of FIG. 4 , select S '= 0.055, corresponding to the reaction temperature of 5 ° C, so the reaction was carried out at a temperature at this time is given by equation theoretical purity of 99.3% obtained ⑴.

[0042] (b)操作过程:在50ml三口烧瓶中加入乙醇20ml、溴化丁基吡啶2.08g (O.Olmol)、L-苯丙氨酸钾2.02g (O.Olmol),在5°C下搅拌8h,过滤出溴化钾,蒸干乙醇,经过离心沉淀器将液体中的少量固体杂质去除,得到丁基吡啶-L-苯丙氨酸盐, 经离子色谱测得纯度为96.6%。 [0042] (b) Procedure: Add three-necked flask 50ml of ethanol 20ml, bromobutyl pyridine 2.08g (O.Olmol), L- phenylalanine potassium 2.02g (O.Olmol), between 5 ° C under stirring 8h, potassium bromide was filtered off, ethanol evaporated to dryness, a small amount through centrifugation will remove solid impurities in the liquid, give butylpyridine -L- phenylalanine salt by ion chromatography purity is 96.6%.

[0043] 实施例3 [0043] Example 3

[0044] 制备苄基吡啶_ (_) -2-羟基-4-苯丁酸盐 [0044] Preparation of benzyl pyridine _ (_) -2-hydroxy-4-phenylbutyrate

[0045] (1)原料 [0045] (1) Raw material

[0046] (a)手性有机羧酸盐:选择(_) -2-羟基-4-苯丁酸钠(Na[RHPA]) (R =苯基、η =2、Z =羟基、M =钠) [0046] (a) a chiral organic carboxylates: Select (_) -2-hydroxy-4-phenyl butyrate Sodium (Na [RHPA]) (R = phenyl, η = 2, Z = hydroxy, M = sodium)

[0047] (b)卤代氮杂环离子液体:选择氯化苄基吡啶([BnP]Cl) (R = 丁基、X =氯) [0047] (b) halo azetidin ionic liquids: Select benzyltriethylammonium chloride pyridine ([BnP] Cl) (R = butyl, X = chloro)

[0048] (2)制备过程 [0048] (2) Preparation process

[0049] (a)参数选择:测定氯化钠和(_)-2-羟基-4-苯丁酸钠在甲醇中的溶解度,绘制5-60°C的溶解度曲线如图5,得到溶解度比值与温度的关系如图6,从中选择S' = 0.400, 对应的反应温度为5°C,因此在该温度下进行反应,此时由公式⑴计算得到的理论纯度为46.9% ο [0049] (a) parameter selection: Determination of sodium chloride, and (_) - 2-hydroxy-4-phenyl sodium butyrate in methanol solubility, solubility curves plotted in FIG. 5 5-60 ° C, to give a ratio of solubility 6 and temperature relationship, select S '= 0.400, corresponding to a reaction temperature of 5 ° C, so the reaction was carried out at a temperature, calculated by the theoretical formula ⑴ purity obtained at this time is 46.9% ο

[0050] (b)操作过程:在50ml三口烧瓶中加入甲醇20ml、氯化苄基吡啶2.06g(O.Olmol) > (_)_2_ 羟基-4-苯丁酸钠2.02g(O.Olmol),在5°C 下搅拌8h,过滤出氯化钠,蒸干甲醇,经过离心沉淀器将液体中的少量固体杂质去除,得到苄基吡啶_ (_) -2-羟基-4-苯丁酸盐,经离子色谱测得纯度为44.6 %。 [0050] (b) Procedure: methanol was added 50ml three-necked flask 20ml, benzyl chloride, pyridine 2.06g (O.Olmol)> (_) _ 2_ hydroxy-4-phenylbutyrate sodium 2.02g (O.Olmol) the mixture was stirred at 5 ° C 8h, sodium chloride was filtered off, the methanol evaporated to dryness, a small amount through centrifugation will remove solid impurities in the liquid to give benzyl pyridine _ (_) -2-hydroxy-4-phenylbutyric acid salt by ion chromatography purity is 44.6%.

[0051] 实施例4 [0051] Example 4

[0052] 制备1- 丁基-3-甲基咪唑-L-苯丙氨酸盐 [0052] Preparation of 1-butyl-3-methylimidazolium phenylalanine salt -L-

[0053] (1)原料 [0053] (1) Raw material

[0054] (a)手性有机羧酸盐:选择L-苯丙氨酸钾(K[PAL]) (R =苯基、η = 1、Z =氨基、M=钾) [0054] (a) a chiral organic carboxylic acid salt: potassium benzene select L- phenylalanine (K [PAL]) (R = phenyl, η = 1, Z = amino, M = K)

[0055] (b)卤代氮杂环离子液体:选择氯化-1-丁基-3-甲基咪唑(R= 丁基、X=氯) [0055] (b) halo azetidin ionic liquids: select 3-methylimidazolium chloride, 1-butyl (R = butyl, X = chloro)

[0056] (2)制备过程 [0056] (2) Preparation process

[0057] (a)参数选择:测定氯化钾和L-苯丙氨酸钾在丙酮中的溶解度,绘制5-50°C的溶解度曲线如图7,得到溶解度比值与温度的关系如图8,从中选择S'= 0.00015,对应的反应温度为50°C,因此在该温度下进行反应,此时由公式⑴计算得到的理论纯度为99.9%。 [0057] (a) parameter selection: Relationship determine the solubility of potassium chloride and potassium L- phenylalanine in acetone, 5-50 ° C solubility curves plotted in FIG. 7, to obtain the temperature ratio of solubility in FIG. 8 , select S '= 0.00015, corresponding to the reaction temperature of 50 ° C, so the reaction was carried out at a temperature, calculated by the theoretical formula ⑴ purity obtained at this time was 99.9%.

[0058] (b)操作过程:在50ml三口烧瓶中加入丙酮20ml、氯化丁基_3_甲基咪唑1.75g(0.01mol)、L-苯丙氨酸钾2.04g(0.01mol),在50°C下搅拌8h,过滤出氯化钾,蒸干 [0058] (b) Procedure: In 20ml of acetone was added 50ml three-necked flask, butyl methylimidazolium chloride _3_ 1.75g ​​(0.01mol), L- phenylalanine potassium 2.04g (0.01mol), in was stirred 8h at 50 ° C, potassium chloride was filtered off, evaporated to dryness

丙酮,经过离心沉淀器将液体中的少量固体杂质去除,得到1- 丁基-3-甲基咪唑-L-苯丙氨酸盐,经离子色谱测得纯度为97.6%。 Acetone, a small amount through centrifugation will remove solid impurities in the liquid, to give 1-butyl-3-methylimidazolium phenylalanine salt -L- by ion chromatography Purity is 97.6%.

Claims (2)

1. 一种制备阴离子手性离子液体的方法,将手性羧酸盐与卤代氮杂环盐在有机溶剂中反应,生成阴离子手性离子液体和无机碱金属卤化盐,再分离除去卤化盐得到阴离子手性离子液体,其特征是预先通过测定手性羧酸盐和商化盐在有机溶剂中的溶解度并得比值,选择最小的比值,从而确定反应温度,在此温度下将手性羧酸盐与卤代氮杂环盐在有机溶剂中反应。 1. A method of preparing an anionic chiral ionic liquids, the chiral azacyclic ring with a halogenated carboxylate salt in an organic solvent, to yield the chiral ionic liquids and anionic inorganic alkali metal halide salts, halide salts and then separated and removed An anionic chiral ionic liquids, wherein the solubility is determined in advance by chiral salts of carboxylates and supplier in an organic solvent and have the ratio, selecting the minimum ratio, to determine the temperature of the reaction at this temperature chiral carboxylic salt with a halogenated nitrogen heterocycle salt in an organic solvent.
2.如权利要求1所述的一种制备阴离子手性离子液体的方法,其特征是选择的反应温度为所述商化盐在此溶剂中的溶解度与所述商代氮杂环盐在此溶剂中的溶解度的比值小于0.05。 2. A method for preparing anionic chiral ionic liquids according to claim 1, wherein the reaction temperature is selected as the quotient of the solubility of this salt in a solvent and the salt in this Shang azetidin solubility of the ratio is less than 0.05.
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004277351A (en) * 2003-03-17 2004-10-07 Yuichi Ishikawa Ionic liquid for chiral separation
WO2005009935A1 (en) * 2003-07-25 2005-02-03 Postech Foundation Method of preparation of optically active alcohols
CN1651089A (en) * 2004-12-06 2005-08-10 河北师范大学 Non-toxic ionic liquid, preparation method and its application
CN1749249A (en) * 2005-09-09 2006-03-22 浙江大学 Chiral ionic liquid and its preparing method
CN101108827A (en) * 2007-07-27 2008-01-23 浙江工业大学 Method for manufacturing acetic acid type ionic liquid
WO2010097412A1 (en) * 2009-02-25 2010-09-02 Dublin City University Ionic liquid solvents

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004277351A (en) * 2003-03-17 2004-10-07 Yuichi Ishikawa Ionic liquid for chiral separation
WO2005009935A1 (en) * 2003-07-25 2005-02-03 Postech Foundation Method of preparation of optically active alcohols
CN1651089A (en) * 2004-12-06 2005-08-10 河北师范大学 Non-toxic ionic liquid, preparation method and its application
CN1749249A (en) * 2005-09-09 2006-03-22 浙江大学 Chiral ionic liquid and its preparing method
CN101108827A (en) * 2007-07-27 2008-01-23 浙江工业大学 Method for manufacturing acetic acid type ionic liquid
WO2010097412A1 (en) * 2009-02-25 2010-09-02 Dublin City University Ionic liquid solvents

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
JIE DING,ET AL: "Chiral Ionic Liquids: Synthesis and Applications", 《CHIRALITY》 *
KATHARINA BICA,ET AL: "Applications of Chiral Ionic Liquids", 《EUROPEAN JOURNAL OF ORGANIC CHEMISTRY》 *
仇深杰,等: "手性离子液体的合成及其应用", 《化学通报》 *
孙洪海,等: "手性离子液体的合成", 《化学进展》 *
曹霞,等: "手性离子液体的合成", 《有机化学》 *

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