CN104945435B - A kind of monodentate difunctionalization imidazole type ion liquid and preparation method thereof - Google Patents
A kind of monodentate difunctionalization imidazole type ion liquid and preparation method thereof Download PDFInfo
- Publication number
- CN104945435B CN104945435B CN201510401194.0A CN201510401194A CN104945435B CN 104945435 B CN104945435 B CN 104945435B CN 201510401194 A CN201510401194 A CN 201510401194A CN 104945435 B CN104945435 B CN 104945435B
- Authority
- CN
- China
- Prior art keywords
- organic phase
- product
- phase
- monodentate
- difunctionalization
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Abstract
A kind of monodentate difunctionalization imidazole type ion liquid, the ionic liquid have following structural formula：Wherein, R1It is derived from C3H7、C4H9、C5H11、C6H13In one kind；R2The one kind being derived from Ph, OEt.Present invention also offers the preparation method of above-mentioned ionic liquid.The monodentate difunctionalization imidazole type ion liquid of the present invention, all has the P=O groups that may participate in coordination on anions and canons, has good coordination ability, and preparation method is simple, and cost is low.
Description
Technical field
The invention belongs to field of compound preparation, and in particular to a kind of monodentate difunctionalization imidazole type ion liquid；This hair
The bright preparation method for further relating to above-mentioned ionic liquid.
Background technology
Ionic liquid is made of organic cation and inorganic or organic anion, at a temperature of room temperature or near room temperature
In the salt of liquid condition, compared with conventional organic solvents, there is ionic liquid steam to force down, is nonflammable, liquid temperature scope
The features such as wide.In addition, the structure of ionic liquid has designability, you can passes through modification or the structure or kind of modulation zwitterion
Class regulates and controls the physics of ionic liquid and chemical property, is referred to as " designer's solvent ".By the functionalized ion liquid of design
Refer to the cation or cloudy from for functionalization group being incorporated into ionic liquid, so that as single-minded with specific function, task
The ionic liquid of property.
Varied due to functional group, thus derivative different types of functionalized ion liquid has varied
Purposes, such as be used for absorbing carbon dioxide, catalysis organic reaction, extract with separating, as reaction dissolvent.
Specifically see application of the ionic liquid in extraction and separation：Functionalized ion liquid can be used for extracting organic matter,
Because ionic liquid steam forces down, not volatile and heat endurance is good, after the completion of extraction, steamed by heating extraction phase or decompression
Evaporate, it can be achieved that the separation of organic matter and ionic liquid.Such as, Rogers et al. first Applications hydrophobicity ionic liquid [bmim]
[PF6] benzene derivates such as toluene, benzoic acid, aniline, chlorobenzene are extracted from water；Afterwards, Pereiro et al. ionic liquids 1,
3- methylimidazoles methylsulfuric acid ([mmim] [MeSO4]) heptane in extractant ethanol-heptane azeotropic mixture, it turns out that
[mmim][MeSO4] extraction efficiency it is high, ionic liquid can be recycled.
In addition to extracting organic matter, ion liquid abstraction separating metal ions are also common one kind side in chemical analysis
Method, its difference based on the compound that different metal ions are formed distribution ratio in immiscible two-phase solvent, makes target
Metal ion mutually enters organic phase from water and achievees the purpose that to be separated from each other.Such as, Rogers and Visser et al. are sulphur, urea, sulphur
The different coordination atom such as urea, thioether or structure are incorporated into the substituent on glyoxaline cation, and anion is [PF6]-, obtain 6 kinds
Hydrophobic function ionic liquid, for Metal Ions Cd in extraction water2+And Hg2+。
In addition, the ligand of the group containing P=O has preferable coordination ability with group of the lanthanides, actinides, it is related at present to contain P=O
The research of radical functino ionic liquid focuses primarily upon anionic functional ionic liquid, and related cationic functionalization contains P=O
The ionic liquid correlative study report of group is less.
The content of the invention
For deficiency of the prior art, the present invention provides a kind of monodentate difunctionalization imidazole type ion liquid, it is cloudy,
There is the P=O groups for being coordinated on cation；Present invention also offers the preparation method of the ionic liquid.
The present invention is achieved through the following technical solutions.
A kind of monodentate difunctionalization imidazole type ion liquid, the ionic liquid have following structural formula：
Wherein, R1It is derived from C3H7、C4H9、C5H11、C6H13In one kind；R2The one kind being derived from Ph, OEt.
In above-mentioned ionic liquid, P204 is di-(2-ethylhexyl)phosphoric acid ester, thereon with P=O groups, therefore the present invention
Ionic liquid in, all have on cation and anion and may participate in the P=O groups of coordination, good rare earth element configurational energy
Power is expected.
Present invention also offers the preparation method of above-mentioned ionic liquid, comprise the following steps：
A. the N- alkyl imidazoles, 3- bromopropyl substituent phosphine oxides that molar ratio is 0.85~0.95: 1: 0.85~0.95 are taken
It is spare with di-(2-ethylhexyl)phosphoric acid ester, N- alkyl imidazoles are dissolved in benzene kind solvent, 3- bromines are added dropwise under heating stirring state
When propyl substituent phosphine oxide and small reaction 4~8, reaction solution is obtained, above-mentioned N- alkyl imidazoles are derived from N- propyl imidazoles, N- butyl
One kind in imidazoles, N- amyl groups imidazoles, N- hexyl imidazoliums, above-mentioned 3- bromopropyls substituent phosphine oxide are derived from 3- bromopropyl diethoxies
One kind in base phosphine oxide, 3- bromopropyls diphenyl phosphine oxide, 3- bromopropyl phenyl ethoxy phosphine oxides；
B. the reaction solution in step a is cooled to room temperature, removes solvent, add deionized water dissolving product, after dissolving
To water phase one, with the mixed liquor washings phase one of ethyl acetate and petroleum ether, water phase two is obtained；
When c. by di-(2-ethylhexyl)phosphoric acid ester and small sodium reflux 23~25, obtained sodium salt is dissolved in dichloromethane
In, then by the dichloromethane solution and the water phase two in step b be mixed 2~4 it is small when, liquid separation obtains organic phase one, spends
The ion water washing organic phase one, and organic phase two is obtained after drying；
D. the organic phase two in step c is rotated into removing dichloromethane, and the double work(of the monodentate is obtained after being dried in vacuo
Imidazole type ion liquid can be changed.
Preferably, the benzene kind solvent in the step a is toluene or benzene.
Preferably, the volume of ethyl acetate and petroleum ether in the mixed liquor of ethyl acetate and petroleum ether in the step b
Than for 3: 1.
Preferably, temperature is 65 DEG C~75 DEG C when being dried in vacuo in the step d, vacuum drying time is small for 2.5~4
When.
Compared with prior art, the invention has the advantages that：1) a kind of monodentate difunctionalization imidazole type is provided
Ionic liquid, all has the P=O groups that may participate in coordination on anions and canons, has good coordination ability；2) provide
The preparation method of ionic liquid is stated, preparation method is simple, and cost is low.
Brief description of the drawings
Fig. 1 is the infrared figure of product in embodiment one.
Fig. 2 is the nuclear-magnetism P spectrograms of product in embodiment one.
Fig. 3 is the nuclear-magnetism H spectrograms of product in embodiment one.
Fig. 4 is the nuclear-magnetism C spectrograms of product in embodiment one.
Fig. 5 is the infrared figure of product in embodiment two.
Fig. 6 is the nuclear-magnetism P spectrograms of product in embodiment two.
Fig. 7 is the nuclear-magnetism H spectrograms of product in embodiment two.
Fig. 8 is the nuclear-magnetism C spectrograms of product in embodiment two.
Fig. 9 is the infrared figure of product in embodiment three.
Figure 10 is the nuclear-magnetism P spectrograms of product in embodiment three.
Figure 11 is the nuclear-magnetism H spectrograms of product in embodiment three.
Figure 12 is the nuclear-magnetism C spectrograms of product in embodiment three.
Figure 13 is the infrared figure of product in example IV.
Figure 14 is the nuclear-magnetism P spectrograms of product in example IV.
Figure 15 is the nuclear-magnetism H spectrograms of product in example IV.
Figure 16 is the nuclear-magnetism C spectrograms of product in example IV.
Figure 17 is the positive mass spectrum figure of product in embodiment five.
Figure 18 is the positive mass spectrum figure of product in embodiment six.
Figure 19 is the positive mass spectrum figure of product in embodiment seven.
Figure 20 is the positive mass spectrum figure of product in embodiment eight.
Figure 21 is the nuclear-magnetism P spectrograms of product in embodiment nine.
Embodiment
Below in conjunction with the accompanying drawings with embodiment, the present invention is described further.
Embodiment one
Two neck flasks of 100mL are taken, add N- propyl imidazoles (2.10g, 18.0mmol), 35mL toluene；Heating stirring state
Lower dropwise addition 3- bromopropyl diethoxy phosphine oxides (5.18g, 20.0mmol), and 6h is reacted at 85 DEG C, it is cooled to room temperature.Pour out
Upper toluene, adds 100mL deionized water dissolving products and obtains water phase one, with EtOAc: PE=3: 1 organic phase (30mL × 4)
Washings phase one, separates water phase two；Di-(2-ethylhexyl)phosphoric acid ester (P204) (5.80g, 18.0mmol) is under the action of sodium
Flow back 24h, obtained sodium salt is dissolved in dichloromethane 3h is stirred at room temperature with the water phase two separated before, adds 50mL
CH2Cl2Stirring, separates organic phase one.Organic phase one is washed with deionized water (20mL × 5), organic phase two is obtained after liquid separation, is added
Enter anhydrous Na2SO4Dry organic phase two, filtering, vacuum rotary steam go out most of CH2Cl2, 70 DEG C of vacuum drying 3h, obtain faint yellow glutinous
Thick liquid product 9.45g (yield 86%), product structure formula are as follows：
Fig. 1 is the infrared figure of product in embodiment one, and infrared absorption peak is corresponded in ionic liquid at 1226,1033 liang in figure
Two at P=O groups.
Fig. 2 is the nuclear-magnetism P spectrograms of product in embodiment one, it can clearly be seen that the P of two kinds of different chemical environments, it is corresponding with
In ionic liquid two at P in P=O groups.
Fig. 3 is the nuclear-magnetism H spectrograms of product in embodiment one.
Fig. 4 is the nuclear-magnetism C spectrograms of product in embodiment one.
In embodiment one in the positive mass spectrum data of product, measured value 289.1677, theoretical value 289.1681.
In embodiment one in the ion mass spectrum data of product, measured value is 321.2194, and theoretical value is 321.2195.
Embodiment two
Two neck flasks of 100mL are taken, add N- butyl imidazoles (2.24g, 18.0mmol), 40mL toluene, heating stirring state
Lower dropwise addition 3- bromopropyl diethoxy phosphine oxides (5.18g, 20.0mmol)；6h is reacted at 85 DEG C, is cooled to room temperature.Pour out
Layer toluene, adds 100mL deionized water dissolving products and obtains water phase one, washed with EtOAc: PE=3: 1 organic phase (30mL × 4)
Water phase one is washed, separates water phase two；Di-(2-ethylhexyl)phosphoric acid ester (P204) (5.80g, 18.0mmol)) returned under the action of sodium
24h is flowed, obtained sodium salt is dissolved in dichloromethane 3h is stirred at room temperature with the water phase two separated before, adds 50mL CH2Cl2
Stirring, separates organic phase one.Organic phase one is washed with deionized water (20mL × 5), liquid separation, adds anhydrous Na2SO4It is dried to obtain
Organic phase two, filtering, vacuum rotary steam go out most of CH2Cl2, 70 DEG C of vacuum drying 3h, obtain faint yellow thick liquid 9.78g (yields
87%), product structure formula is as follows：
Fig. 5 is the infrared figure of product in embodiment two, and infrared absorption peak is corresponded in ionic liquid at 1230,1057 liang in figure
Two at P=O groups.
Fig. 6 is the nuclear-magnetism P spectrograms of product in embodiment two, it can clearly be seen that the P of two kinds of different chemical environments, it is corresponding with
In ionic liquid two at P in P=O groups.
Fig. 7 is the nuclear-magnetism H spectrograms of product in embodiment two.
Fig. 8 is the nuclear-magnetism C spectrograms of product in embodiment two.
In embodiment two in the positive mass spectrum data of product, measured value 303.1841, theoretical value is 303.1837.
The positive mass spectrum data of product are identical with the ion mass spectrum data of product in embodiment one in embodiment two, no
Also omitted in repeat specification, following embodiments.
Embodiment three
Two neck flasks of 100mL are taken, add N- amyl groups imidazoles (3.30g, 18.0mmol), 35mL toluene, heating stirring state
Lower dropwise addition 3- bromopropyl diethoxy phosphine oxides (6.10g, 0.022mol), react 6h at 85 DEG C, are cooled to room temperature.Pour out
Layer toluene, adds 100mL deionized water dissolving products and obtains water phase one, washed with EtOAc: PE=3: 1 organic phase (30mL × 4)
Water phase one is washed, liquid separation obtains water phase two；Di-(2-ethylhexyl)phosphoric acid ester (P204) (5.80g, 18mmol) is under the action of sodium
Flow back 24h, obtained sodium salt is dissolved in dichloromethane 4h is stirred at room temperature with the water phase two separated before, adds 50mL
CH2Cl2Stirring, separates organic phase one.Organic phase one is washed with deionized water (20mL × 5), liquid separation obtains organic phase two, adds
Anhydrous Na2SO4Dry organic phase two, filtering, vacuum rotary steam go out most of CH2Cl2, 65 DEG C of vacuum drying 4h, obtain faint yellow sticky
Liquid 10.12g (yield 88%), product have following structural formula：
Fig. 9 is the infrared figure of product in embodiment three, and infrared absorption peak is corresponded in ionic liquid at 1229,1034 liang in figure
Two at P=O groups.
Figure 10 is the nuclear-magnetism P spectrograms of product in embodiment three, it can clearly be seen that the P of two kinds of different chemical environments, corresponding
With the P in P=O groups at two in ionic liquid.
Figure 11 is the nuclear-magnetism H spectrograms of product in embodiment three.
Figure 12 is the nuclear-magnetism C spectrograms of product in embodiment three.
In embodiment three in the positive mass spectrum data of product, measured value 317.1986, theoretical value is 317.1994.
Example IV
Two neck flasks of 100mL are taken, add N- hexyl imidazoliums (2.74g, 18.0mmol), 35mL toluene, heating stirring state
Lower dropwise addition 3- bromopropyl diethoxy phosphine oxides (5.18g, 20.0mmol)；6h is reacted at 85 DEG C, is cooled to room temperature.Pour out
Layer toluene, adds 100mL deionized water dissolving products and obtains water phase one, washed with EtOAc: PE=3: 1 organic phase (30mL × 4)
Water phase one is washed, liquid separation obtains water phase two；Effect of the di-(2-ethylhexyl)phosphoric acid ester (P204) (5.80g, 18.0mmol) in sodium
Lower reflux 25h, obtained sodium salt is dissolved in dichloromethane 2h is stirred at room temperature with the water phase two separated before, adds 50mL
CH2Cl2Stirring, separates organic phase one.Organic phase one is washed with deionized water (20mL × 5), liquid separation obtains organic phase two, adds
Anhydrous Na2SO4Dry organic phase two, filtering, vacuum rotary steam go out most of CH2Cl2, 75 DEG C of vacuum drying 2.5h, obtain faint yellow glutinous
Thick liquid 10.58g (yield 90%), product have following structural formula：
Figure 13 is the infrared figure of product in example IV, and infrared absorption peak corresponds to ionic liquid at 1230,1032 liang in figure
In two at P=O groups.
Figure 14 is the nuclear-magnetism P spectrograms of product in example IV, it can clearly be seen that the P of two kinds of different chemical environments, corresponding
With the P in P=O groups at two in ionic liquid.
Figure 15 is the nuclear-magnetism H spectrograms of product in example IV.
Figure 16 is the nuclear-magnetism C spectrograms of product in example IV.
In example IV in the positive mass spectrum data of product, measured value 331.2155, theoretical value is 331.2151.
Embodiment five
Two neck flasks of 100mL are taken, add N- propyl imidazoles (2.17g, 19.0mmol), 35mL toluene, heating stirring state
Lower dropwise addition 3- bromopropyl diphenyl base phosphine oxides (6.46g, 20.0mmol)；8h is reacted at 85 DEG C, is cooled to room temperature.Pour out
Layer toluene, adds 100mL deionized water dissolving products and obtains water phase one, washed with EtOAc: PE=3: 1 organic phase (30mL × 4)
Water phase one is washed, liquid separation obtains water phase two；Effect of the di-(2-ethylhexyl)phosphoric acid ester (P204) (6.12g, 19.0mmol) in sodium
Lower reflux 23h, obtained sodium salt is dissolved in dichloromethane 3h is stirred at room temperature with the water phase two separated before, adds 50mL
CH2Cl2Stirring, separates organic phase one.Organic phase one is washed with deionized water (20mL × 5), liquid separation obtains organic phase two, adds
Anhydrous Na2SO4Dry organic phase two, filtering, vacuum rotary steam go out most of CH2Cl2, 70 DEG C of vacuum drying 3h, obtain faint yellow sticky
Liquid 10.93g (yield 90%), product have following structural formula：
Figure 17 is the positive mass spectrum figure of product in embodiment five, and measured value 353.1770, theoretical value is 353.1777.
Embodiment six
Two neck flasks of 100mL are taken, add N- butyl imidazoles (2.24g, 18.0mmol), 35mL toluene, heating stirring state
Lower dropwise addition 3- bromopropyl diphenyl base phosphine oxides (6.46g, 20.0mmol)；4h is reacted at 85 DEG C, is cooled to room temperature.Pour out
Layer toluene, adds 100mL deionized water dissolving products and obtains water phase one, washed with EtOAc: PE=3: 1 organic phase (30mL × 4)
Water phase one is washed, liquid separation obtains water phase two；Di-(2-ethylhexyl)phosphoric acid ester (P204) (5.80g, 18.0mmol), in the effect of sodium
Lower reflux 24h, obtained sodium salt is dissolved in dichloromethane 3h is stirred at room temperature with the water phase two separated before, adds 50mL
CH2Cl2Stirring, separates organic phase one.Organic phase one is washed with deionized water (20mL × 5), liquid separation obtains organic phase two, adds
Anhydrous Na2SO4Dry organic phase two, filtering, vacuum rotary steam go out most of CH2Cl2, 70 DEG C of vacuum drying 3h, obtain faint yellow sticky
Liquid 11.16g (yield 90%), product have following structural formula：
Figure 18 is the positive mass spectrum figure of product in embodiment six, and measured value is M+ for 367.1921 theoretical values
367.1934。
Embodiment seven
Take two neck flasks of 100mL, add N- amyl groups imidazoles (2.35g, 17.0mmol), 35mL benzene, under heating stirring state
3- bromopropyl diphenyl base phosphine oxides (6.46g, 20.0mmol) are added dropwise；6h is reacted at 85 DEG C, is cooled to room temperature.Pour out upper strata
Benzene, adds 100mL deionized water dissolving products and obtains water phase one, with EtOAc: PE=3: 1 organic phase (30mL × 4) washings
Xiang Yi, liquid separation obtain water phase two；Di-(2-ethylhexyl)phosphoric acid ester (P204) (5.47g, 17.0mmol) returns under the action of sodium
24h is flowed, obtained sodium salt is dissolved in dichloromethane 3h is stirred at room temperature with the water phase two separated before, adds 50mL CH2Cl2
Stirring, separates organic phase one.Organic phase one is washed with deionized water (20mL × 5), liquid separation obtains organic phase two, adds anhydrous
Na2SO4Dry organic phase two, filtering, vacuum rotary steam go out most of CH2Cl2, 70 DEG C of vacuum drying 3h, obtain faint yellow thick liquid
11.51g (yield 91%), product have following structural formula：
Figure 19 is the positive mass spectrum figure of product in embodiment seven, and measured value 381.2084, theoretical value is 381.2090.
Embodiment eight
Two neck flasks of 100mL are taken, add N- hexyl imidazoliums (2.74g, 18.0mmol), 35mL toluene, heating stirring state
Lower dropwise addition 3- bromopropyl diphenyl base phosphine oxides (6.46g, 20.0mmol)；6h is reacted at 85 DEG C, is cooled to room temperature.Pour out
Layer toluene, adds 100mL deionized water dissolving products and obtains water phase one, washed with EtOAc: PE=3: 1 organic phase (30mL × 4)
Water phase one is washed, liquid separation obtains water phase two；Effect of the di-(2-ethylhexyl)phosphoric acid ester (P204) (5.80g, 18.0mmol) in sodium
Lower reflux 24h, obtained sodium salt is dissolved in dichloromethane 3h is stirred at room temperature with the water phase two separated before, adds 50mL
CH2Cl2Stirring, separates organic phase one.Organic phase one is washed with deionized water (20mL × 5), liquid separation obtains organic phase two, adds
Anhydrous Na2SO4Dry organic phase two, filtering, vacuum rotary steam go out most of CH2Cl2, 70 DEG C of vacuum drying 3h, obtain faint yellow sticky
Liquid 12.00g (yield 93%), product have following structural formula：
Figure 20 is the positive mass spectrum figure of product in embodiment eight, and measured value 395.2238, theoretical value is 395.2247.
Embodiment nine
Two neck flasks of 100mL are taken, add N- propyl imidazoles (2.64g, 18.0mmol), 35mL toluene, heating stirring state
Lower dropwise addition 3- bromopropyl phenyl ethoxy phosphine oxides (6.26g, 20.0mmol)；6h is reacted at 85 DEG C, is cooled to room temperature.Pour out
Upper toluene, adds 100mL deionized water dissolving products and obtains water phase one, with EtOAc: PE=3: 1 organic phase (30mL × 4)
Washings phase one, liquid separation obtain water phase two；Work of the di-(2-ethylhexyl)phosphoric acid ester (P204) (5.60g, 18.0mmol) in sodium
With lower reflux 24h, obtained sodium salt is dissolved in dichloromethane 3h is stirred at room temperature with the water phase two separated before, add 50mL
CH2Cl2Stirring, separates organic phase one.Organic phase one is washed with deionized water (20mL × 5), liquid separation obtains organic phase two, adds
Anhydrous Na2SO4Dry organic phase two, filtering, vacuum rotary steam go out most of CH2Cl2, 70 DEG C of vacuum drying 3h, obtain faint yellow sticky
Liquid 12.50g (yield 94%), product have following structural formula：
Figure 21 is the nuclear-magnetism P spectrograms of product in example IV, it can clearly be seen that the P of two kinds of different chemical environments, corresponding
With the P in P=O groups at two in ionic liquid.
The monodentate difunctionalization imidazole type ion liquid prepared into embodiment nine of above example one, anions and canons
On all have and may participate in the P=O groups of coordination, there is good coordination ability.And preparation method is simple, cost is low, and yield is high.
Protection scope of the present invention includes but not limited to embodiment of above, and protection scope of the present invention is with claims
Subject to, any replacement being readily apparent that to those skilled in the art that this technology is made, deformation, improvement each fall within the present invention's
Protection domain.
Claims (2)
1. a kind of monodentate difunctionalization imidazole type ion liquid, it is characterised in that the ionic liquid has following structural formula：
Wherein, R1It is derived from C3H7、C4H9、C5H11、C6H13In one kind；R2The one kind being derived from Ph, OEt.
A kind of 2. preparation method of monodentate difunctionalization imidazole type ion liquid described in claim 1, it is characterised in that including
Following steps：
A. the N- alkyl imidazoles, 3- bromopropyl substituent phosphine oxides and two that molar ratio is 0.85~0.95: 1: 0.85~0.95 are taken
(2- ethylhexyls) phosphate is spare, and N- alkyl imidazoles are dissolved in benzene kind solvent, and 3- bromopropyls are added dropwise under heating stirring state
When substituent phosphine oxide and small reaction 4~8, reaction solution is obtained, above-mentioned N- alkyl imidazoles are derived from N- propyl imidazoles, N- butyl miaows
One kind in azoles, N- amyl groups imidazoles, N- hexyl imidazoliums, above-mentioned 3- bromopropyls substituent phosphine oxide are derived from 3- bromopropyl diethoxies
One kind in phosphine oxide, 3- bromopropyls diphenyl phosphine oxide, 3- bromopropyl phenyl ethoxy phosphine oxides；
B. the reaction solution in step a is cooled to room temperature, removes solvent, added deionized water dissolving product, water is obtained after dissolving
Xiang Yi, with the mixed liquor washings phase one of ethyl acetate and petroleum ether, obtains water phase two；
When c. by di-(2-ethylhexyl)phosphoric acid ester and small sodium reflux 23~25, obtained sodium salt is dissolved in dichloromethane, then
By the dichloromethane solution and the water phase two in step b be mixed 2~4 it is small when, liquid separation obtains organic phase one, uses deionized water
The organic phase one is washed, and organic phase two is obtained after drying；
D. the organic phase two in step c is rotated into removing dichloromethane, and monodentate difunctionalization is obtained after being dried in vacuo
Imidazole type ion liquid；
Wherein, the benzene kind solvent in the step a is toluene or benzene；The mixed liquor of ethyl acetate and petroleum ether in the step b
The volume ratio of middle ethyl acetate and petroleum ether is 3: 1；Temperature is 65 DEG C~75 DEG C when being dried in vacuo in the step d, and vacuum is done
When the dry time is 2.5~4 small.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510401194.0A CN104945435B (en) | 2015-06-30 | 2015-06-30 | A kind of monodentate difunctionalization imidazole type ion liquid and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510401194.0A CN104945435B (en) | 2015-06-30 | 2015-06-30 | A kind of monodentate difunctionalization imidazole type ion liquid and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104945435A CN104945435A (en) | 2015-09-30 |
| CN104945435B true CN104945435B (en) | 2018-04-27 |
Family
ID=54160551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510401194.0A Expired - Fee Related CN104945435B (en) | 2015-06-30 | 2015-06-30 | A kind of monodentate difunctionalization imidazole type ion liquid and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104945435B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106397499A (en) * | 2016-08-31 | 2017-02-15 | 宁波美康生物科技股份有限公司 | Preparation method of 2,3,4-triacetyl-1-(2-chloro-4-nitro-phenyl)-alpha-L-fucopyranoside |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103374035A (en) * | 2012-04-24 | 2013-10-30 | 宁波大学 | Method for microwave synthesis of organic phosphine-functionalized imidazolium-based ionic liquid |
-
2015
- 2015-06-30 CN CN201510401194.0A patent/CN104945435B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103374035A (en) * | 2012-04-24 | 2013-10-30 | 宁波大学 | Method for microwave synthesis of organic phosphine-functionalized imidazolium-based ionic liquid |
Non-Patent Citations (5)
| Title |
|---|
| An Engineering-Purpose Preparation Strategy for Ammonium-Type Ionic Liquid with High Purity;Xiaoqi Sun等;《AICHE Journal》;20090831;第56卷;第989-996页 * |
| Kinetics of cerium(I V) and fluoride extraction from sulfuric solutions using bifunctionalionic liquid extractant (Bif-ILE)[A336][P204];Hua ling Yang等;《Trans. Nonferrous Met. Soc. China》;20140615;第24卷;第1937-1945页 * |
| 一种新型磷酸酯类功能化离子液体的合成及管内循环流液液微萃取钐(III)的研究;危晶等;《中国稀土学报》;20121231;第30卷(第6期);第666-672页 * |
| 新型功能化离子液体的合成及液－液萃取钕(III)的研究;危晶等;《分析试验室》;20120430;第31卷(第4期);第73-77页 * |
| 有机膦离子液体的合成及其作为功能材料的应用;黄飞隆;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20150315;第1-68页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104945435A (en) | 2015-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wang et al. | Recovery of lithium ions from salt lake brine with a high magnesium/lithium ratio using heteropolyacid ionic liquid | |
| CN105536537B (en) | A kind of method of extract and separate lithium isotope | |
| CN105536536B (en) | A kind of extraction system for extracting lithium isotope | |
| Liu et al. | Toward greener separations of rare earths: bifunctional ionic liquid extractants in biodiesel | |
| CN105330681B (en) | A kind of rare earth cluster metal organic anion skeleton of micropore and its preparation method and application | |
| CN106048221A (en) | Method for extracting light rare earth elements in acidic solution by using ionic liquid [OMIM] BF4 | |
| CN105061496A (en) | Novel ionic liquid preparation method | |
| CN104926869B (en) | A kind of bidentate difunctionalization imidazole type ion liquid and preparation method thereof | |
| CN104945435B (en) | A kind of monodentate difunctionalization imidazole type ion liquid and preparation method thereof | |
| CN104923167B (en) | A kind of stable Nano-meter SiO_22the preparation method of/tributyl phosphate composite adsorbing material | |
| CN105837627B (en) | A kind of difunctionalization quaternary ammonium salt ionic liquid and preparation method thereof | |
| CN110218866A (en) | A kind of P204Adulterate the preparation method and applications of polythiophene light rare earth solid extracting agent | |
| CN102167683A (en) | Bivalent cation magnetic ionic liquids and preparation method thereof | |
| CN102924749A (en) | Ionic liquid-type phosphate fire retardant and preparation method thereof | |
| CN108558765A (en) | A kind of ether functional ionic liquids and preparation method thereof | |
| CN106048261A (en) | Method for extracting vanadium from acidic solution by using ionic liquid [OMIM]BF4 | |
| CN105837628B (en) | A kind of difunctionalization quaternary phosphonium ionic liquid and preparation method thereof | |
| CN104311428A (en) | Pentaalkyl-diethylene-tri-tert-amine and its preparation method and use | |
| CN108383882A (en) | A kind of monosubstituted cobaltocene cationic derivative and high efficiency preparation method | |
| CN106582569A (en) | Ion imprinted impregnating resin and preparation method thereof | |
| CN101768045B (en) | Method for preparing halogenated hydrocarbons from strong acidic ionic liquid | |
| CN105503612B (en) | Ammonium salt of six alkyl triethylene of tetramethyl four and its preparation method and application | |
| CN103772285B (en) | A kind of recovery method of Analgin finished mother liquid | |
| Liu et al. | Efficient selective leaching of ytterbium and lutetium oxides by new hydrophobic deep eutectic solvents | |
| CN106496584A (en) | Phthalic acid cadmium polymer and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20201218 Address after: 257000 Wanda harbor city, No. 25-1, Gangcheng Road, Dongying Port Economic Development Zone, Dongying City, Shandong Province Patentee after: Shandong Xingqiang Chemical Industry Technology Research Institute Co., Ltd Address before: Box 29, Ningbo University, 818 Fenghua Road, Jiangbei District, Ningbo City, Zhejiang Province, 315211 Patentee before: Ningbo University |
|
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20180427 Termination date: 20210630 |