CN102718713A - Chiral ionic liquid magnetic nanoparticle product and preparation method and application thereof - Google Patents
Chiral ionic liquid magnetic nanoparticle product and preparation method and application thereof Download PDFInfo
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- CN102718713A CN102718713A CN2012102343581A CN201210234358A CN102718713A CN 102718713 A CN102718713 A CN 102718713A CN 2012102343581 A CN2012102343581 A CN 2012102343581A CN 201210234358 A CN201210234358 A CN 201210234358A CN 102718713 A CN102718713 A CN 102718713A
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Abstract
The invention relates to a chiral ionic liquid magnetic nanoparticle product and a preparation method and application thereof. The preparation method comprises the following steps: dissolving FeCl3.6H2O, succinic acid and urea into 1,2-propanediol, putting the solution into a reaction kettle, and reacting to obtain an Fe3O4 magnetic nanoparticle; adding the Fe3O4 magnetic nanoparticle into a mixed solvent of H2O and EtOH, adding NH3.H2O and TEOS (tetraethoxysilane), and reacting to obtain Fe3O4/SiO2; and adding the Fe3O4/SiO2 into dimethyl sulfoxide, adding 1-alkyl-3-methylimidazolyl-L-proline salt or 1-alkyl-3-methylimidazolyl-L-lactate ionic liquid, and adding hexamethylene-1,6-diisocyanate to obtain the chiral imidazole ionic liquid magnetic nanoparticle. During application of the chiral ionic liquid magnetic nanoparticle to chiral separation of 1-phenyl-1,2-ethylene glycol and 1-hydroxy acenaphthene, the separation time is short, the operation is simple and convenient, and the separation effect of a chiral compound is good.
Description
Technical field
The present invention relates to a kind of chiral ionic liquid magnetic nano-particle product and preparation and application.
Background technology
Chipal compounds is meant that molecular weight, molecular structure are identical, but the molecule that does not overlap with its mirror image in kind.Two molecules with mirror in kind each other are enantiomer (abbreviation enantiomorph); Except that opticity; Enantiomorph has identical physical properties; But in chiral environment, can show the different functions characteristic, for example the enantiomorph in medicine, foodstuff additive, agricultural chemicals, seasonings and the spices can show pharmacology and the qualitative difference of clinical application.The chipal compounds separation receives increasing concern; Separation method to chipal compounds mainly contains chemical resolution method, crystallization Split Method, biological Split Method, film Split Method and chromatogram Split Method at present, and the chromatogram Split Method mainly comprises chromatogram chiral stationary phase method and chiral additives method.Developed multiple liquid chromatography chiral stationary phase at present; Like protein type, Prikle type, polysaccharide derivates type, ligand exchange type and Schardinger dextrins type etc.; And these separation are high to instrument performance, material purity requirement; Cost an arm and a leg, length consuming time, have the difficult problems such as being prone to cause waste and pollution that reclaim simultaneously, it is vital therefore developing more effective chiral separation material.Ionic liquid is meant in room temperature or near presenting organic salt liquid, that be made up of zwitterion fully under the room temperature.Ionic liquid has the many character that is different from water and OOS, like designability, lower melting point, high thermal stability, high chemical stability, extremely-low vapor pressure and good dissolving ability etc.Wherein, chiral ionic liquid combines the advantage and the characteristic of ionic liquid and chiral material two aspects, can be used as chiral solvent or chiral induction agent, and aspects such as, chiral catalysis synthetic in chirality and chiral separation have very big application potential.Nano material is meant the material of being made up of at the nanoparticle of 1 ~ 100nm size, and wherein magnetic Nano material mainly is red stone (γ-Fe
2O
3, Fe
3O
4) nanoparticle caused widely and to pay close attention to that the research in this field has also obtained significant achievement.Research through nearly decades shows that magnetic ferric oxide nano particles has developed quite maturation on technology of preparing, and its chemical synthesis mainly comprises: sol-gel method, microemulsion method, solvent-thermal method and coprecipitation method etc.Because characteristics such as the ferric oxide nano particles size is little, specific surface area is big, the surface atom number increases, Atomic coordinate deficiency; Make it have very big surperficial Gibbs free energy; Show as thermodynamic instability; Owing to the existence of dipole-dipole effect, therefore very easily spontaneously reunion, oxidation carried out finishing to nanoparticle and be very important to improve its stability simultaneously.Silicon-dioxide has excellent biological compatibility, has not only strengthened Fe
3O
4Stability in solution, and the silanol that the surface exists is easy to further derive, and therefore selecting tetraethoxy is that properties-correcting agent is at Fe
3O
4Surface coated inorganic thing SiO
2, formed and had nucleocapsid structure Fe
3O
4/ SiO
2Composite nanoparticle.Select for use 1-ethyl-3-Methylimidazole-L-proline salt (EMIMLpro) ionic liquid as chiral source, hexa-methylene-1,6-vulcabond (DIH) is modified Fe as linking agent with chiral ionic liquid
3O
4/ SiO
2The composite magnetic nanoparticle surface, thus prepare Fe
3O
4/ SiO
2The multi-functional composite magnetic nanoparticle that this type of/DIH/EMIMLpro not only had the chiral recognition ability but also had magnetic.Utilize the chiral ionic liquid magnetic nano-particle for preparing to two kinds of racemize medicine (1-phenyl-1 at last; 2-terepthaloyl moietie, 1-hydroxyl acenaphthene) carry out the chiral separation preliminary study, and through performance liquid chromatography and optically-active separating resulting is analyzed.Find that it has certain chiral separation ability to racemic compound, and under externally-applied magnetic field with after end liquid thoroughly separates, reach recovery fully basically, environmental protection is economical again, and practical value is high.
Summary of the invention
The object of the invention provides a kind of chiral ionic liquid functionalized magnetic nano particle; It is bonded chiral ionic liquid on magnetic nano-particle; Thereby obtain the chiral ionic liquid functionalized magnetic nano particle, and realize its application aspect commercially available racemic compound separation.
The chiral ionic liquid magnetic nano-particle, its structural formula is:
Wherein,
Represent Fe
3O
4Magnetic nano-particle;
Represent coated Si O
2The silicon shell;
Represent coated Si O
2The Fe of silicon fiml
3O
4Magnetic nano-particle; R
1Be selected from C
1-C
16Alkyl;
Or
Wherein,
Represent Fe
3O
4Magnetic nano-particle;
Represent coated Si O
2The silicon shell;
Represent coated Si O
2The Fe of silicon fiml
3O
4Magnetic nano-particle; R
2Be selected from C
1-C
16Alkyl;
The preparation method of chiral ionic liquid magnetic nano-particle of the present invention:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 0.5-1.5g, succsinic acid 0.1-1g, urea 0.1-1g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 5-10h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.1-1g, add H
2O and EtOH volume ratio are in the mixed solvent of 1-5, and ultra-sonic dispersion 10-50min stirs adding NH down
3.H
2O is adjusted to pH=9-10, adds the 0.25-2.5ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 4-12h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind the 50-100 ℃ of vacuum drying
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.1g-1g joins in the 30-100ml DMSO 99.8MIN. (DMSO); The back adds 0.2-2ml1-alkyl-3-Methylimidazole-L-proline salt (EMIMLpro) or 1-alkyl-3-Methylimidazole-L-lactate ions liquid; Behind the ultra-sonic dispersion; Add 0.1-1ml hexa-methylene-1,6-vulcabond (DIH) is at 50-100 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 12-48 hour, use acetone and washing with alcohol successively after reducing to room temperature, 50-100 ℃ of vacuum drying promptly obtains product chiral imidazole ionic liquid magnetic nano-particle.Alkyl is selected from C
1-C
16Alkyl.
Reaction formula:
The evaluation of chirality magnetic nano-particle chiral separation sexuality
Use above-mentioned chiral ionic liquid magnetic nano-particle; To 1-phenyl-1; 2-terepthaloyl moietie, 1-hydroxyl acenaphthene carry out chiral separation, through performance liquid chromatography, specific rotation test, prove that the chiral ionic liquid magnetic Nano material of preparation has certain chiral separation ability.
The present invention have disengaging time short, simple to operation, to advantage such as the chirality compound separation is effective.And this chirality magnetic particle can thoroughly separate with end liquid under externally-applied magnetic field, neither can pollute and can reclaim fully the target isolate, thereby reach economy both sides' purpose of environmental protection again.
Embodiment
Embodiment 1:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 0.5g, succsinic acid 0.1g, urea 0.1g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 5h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.1g, add H
2O and EtOH volume ratio are in 1 the mixed solvent, and ultra-sonic dispersion 10min stirs and adds NH down
3.H
2O is adjusted to pH=9, adds the 0.5ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 4h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 50 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.1g joins in the 30ml DMSO 99.8MIN., and the back adds 0.2ml 1-ethyl-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.1ml hexa-methylene-1, and the 6-vulcabond is at 50 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 12 hours, use acetone and washing with alcohol successively after reducing to room temperature, 50 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 2:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 0.6g, succsinic acid 0.2g, urea 0.2g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 5h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.2g, add H
2O and EtOH volume ratio are in 1 the mixed solvent, and ultra-sonic dispersion 10min stirs and adds NH down
3.H
2O is adjusted to pH=9, adds the 0.5ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 5h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 50 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.2g joins in the 30ml DMSO 99.8MIN., and the back adds 0.4ml 1-ethyl-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.2ml hexa-methylene-1, and the 6-vulcabond is at 50 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 16 hours, use acetone and washing with alcohol successively after reducing to room temperature, 50 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 3:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 0.6g, succsinic acid 0.3g, urea 0.3g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 6h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.3g, add H
2O and EtOH volume ratio are in 2 the mixed solvent, and ultra-sonic dispersion 20min stirs and adds NH down
3.H
2O is adjusted to pH=9, adds the 0.75ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 6h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 60 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.3g joins in the 40ml DMSO 99.8MIN., and the back adds 0.6ml 1-ethyl-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.3ml hexa-methylene-1, and the 6-vulcabond is at 60 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 18 hours, use acetone and washing with alcohol successively after reducing to room temperature, 60 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 4:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 0.8g, succsinic acid 0.4g, urea 0.4g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 6h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.4g, add H
2O and EtOH volume ratio are in 2 the mixed solvent, and ultra-sonic dispersion 20min stirs and adds NH down
3.H
2O is adjusted to pH=9, adds the 0.1ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 7h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 60 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.4g joins in the 50ml DMSO 99.8MIN., and the back adds 0.8ml 1-ethyl-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.4ml hexa-methylene-1, and the 6-vulcabond is at 60 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 20 hours, use acetone and washing with alcohol successively after reducing to room temperature, 60 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 5:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 0.9g, succsinic acid 0.5g, urea 0.5g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 7h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.5g, add H
2O and EtOH volume ratio are in 3 the mixed solvent, and ultra-sonic dispersion 30min stirs and adds NH down
3.H
2O is adjusted to pH=9, adds the 1.25ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 8h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 70 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.5g joins in the 60ml DMSO 99.8MIN., and the back adds 1ml 1-ethyl-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.5ml hexa-methylene-1, and the 6-vulcabond is at 70 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 24 hours, use acetone and washing with alcohol successively after reducing to room temperature, 70 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 6:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 1.0g, succsinic acid 0.6g, urea 0.6g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 7h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.6g, add H
2O and EtOH volume ratio are in 3 the mixed solvent, and ultra-sonic dispersion 30min stirs and adds NH down
3.H
2O is adjusted to pH=10, adds the 1.5ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 8h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 70 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.6g joins in the 70ml DMSO 99.8MIN., and the back adds 1.2ml 1-ethyl-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.6ml hexa-methylene-1, and the 6-vulcabond is at 70 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 28 hours, use acetone and washing with alcohol successively after reducing to room temperature, 70 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 7:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 1.1g, succsinic acid 0.7g, urea 0.7g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 8h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.7g, add H
2O and EtOH volume ratio are in 4 the mixed solvent, and ultra-sonic dispersion 40min stirs and adds NH down
3.H
2O is adjusted to pH=10, adds the 1.75ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 9h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 80 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.7g joins in the 70ml DMSO 99.8MIN., and the back adds 1.4ml 1-ethyl-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.7ml hexa-methylene-1, and the 6-vulcabond is at 80 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 32 hours, use acetone and washing with alcohol successively after reducing to room temperature, 80 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 8:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 1.2g, succsinic acid 0.8g, urea 0.8g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 8h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.8g, add H
2O and EtOH volume ratio are in 4 the mixed solvent, and ultra-sonic dispersion 40min stirs and adds NH down
3.H
2O is adjusted to pH=10, adds the 2ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 10h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 80 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.8g joins in the 80ml DMSO 99.8MIN., and the back adds 1.6ml1-ethyl-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.8ml hexa-methylene-1, and the 6-vulcabond is at 80 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 36 hours, use acetone and washing with alcohol successively after reducing to room temperature, 80 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 9:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 1.3g, succsinic acid 0.9g, urea 0.9g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 9h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.9g, add H
2O and EtOH volume ratio are in 5 the mixed solvent, and ultra-sonic dispersion 50min stirs and adds NH down
3.H
2O is adjusted to pH=10, adds the 2.25ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 11h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 90 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.9g joins in the 90ml DMSO 99.8MIN., and the back adds 1.8ml 1-ethyl-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.9ml hexa-methylene-1, and the 6-vulcabond is at 90 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 40 hours, use acetone and washing with alcohol successively after reducing to room temperature, 90 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 10:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 1.5g, succsinic acid 1g, urea 1g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 10h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
41g adds H
2O and EtOH volume ratio are in 5 the mixed solvent, and ultra-sonic dispersion 50min stirs and adds NH down
3.H
2O is adjusted to pH=10, adds the 2.5ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 12h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 100 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 1g joins in the 100ml DMSO 99.8MIN., and the back adds 2ml 1-ethyl-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 1ml hexa-methylene-1, and the 6-vulcabond is at 100 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 48 hours, use acetone and washing with alcohol successively after reducing to room temperature, 100 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 11:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 0.5g, succsinic acid 0.1g, urea 0.1g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 5h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.1g, add H
2O and EtOH volume ratio are in 1 the mixed solvent, and ultra-sonic dispersion 10min stirs and adds NH down
3.H
2O is adjusted to pH=9, adds the 0.5ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 4h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 50 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.1g joins in 30 DMSO 99.8MIN.s, and the back adds 0.2ml 1-propyl group-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.1ml hexa-methylene-1, and the 6-vulcabond is at 50 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 12 hours, use acetone and washing with alcohol successively after reducing to room temperature, 50 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 12:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 0.6g, succsinic acid 0.2g, urea 0.2g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 5h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.2g, add H
2O and EtOH volume ratio are in 1 the mixed solvent, and ultra-sonic dispersion 10min stirs and adds NH down
3.H
2O is adjusted to pH=9, adds the 0.5ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 5h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 50 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.2g joins in the 30ml DMSO 99.8MIN., and the back adds 0.4ml1-butyl-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.2ml hexa-methylene-1, and the 6-vulcabond is at 50 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 16 hours, use acetone and washing with alcohol successively after reducing to room temperature, 50 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 13:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 0.6g, succsinic acid 0.3g, urea 0.3g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 6h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.3g, add H
2O and EtOH volume ratio are in 2 the mixed solvent, and ultra-sonic dispersion 20min stirs and adds NH down
3.H
2O is adjusted to pH=9, adds the 0.75ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 6h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 60 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.3g joins in the 40ml DMSO 99.8MIN., and the back adds 0.6ml 1-amyl group-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.3ml hexa-methylene-1, and the 6-vulcabond is at 60 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 18 hours, use acetone and washing with alcohol successively after reducing to room temperature, 60 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 14:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 0.8g, succsinic acid 0.4g, urea 0.4g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 6h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.4g, add H
2O and EtOH volume ratio are in 2 the mixed solvent, and ultra-sonic dispersion 20min stirs and adds NH down
3.H
2O is adjusted to pH=9, adds the 0.1ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 7h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 60 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.4g joins in the 50ml DMSO 99.8MIN., and the back adds 0.8ml1-hexyl-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.4ml hexa-methylene-1, and the 6-vulcabond is at 60 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 20 hours, use acetone and washing with alcohol successively after reducing to room temperature, 60 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 15:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 0.9g, succsinic acid 0.5g, urea 0.5g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 7h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.5g, add H
2O and EtOH volume ratio are in 3 the mixed solvent, and ultra-sonic dispersion 30min stirs and adds NH down
3.H
2O is adjusted to pH=9, adds the 1.25ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 8h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 70 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.5g joins in the 60ml DMSO 99.8MIN., and the back adds 1ml 1-heptyl-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.5ml hexa-methylene-1, and the 6-vulcabond is at 70 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 24 hours, use acetone and washing with alcohol successively after reducing to room temperature, 70 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 16:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 1.0g, succsinic acid 0.6g, urea 0.6g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 7h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.6g, add H
2O and EtOH volume ratio are in 3 the mixed solvent, and ultra-sonic dispersion 30min stirs and adds NH down
3.H
2O is adjusted to pH=10, adds the 1.5ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 8h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 70 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.6g joins in the 70ml DMSO 99.8MIN., and the back adds 1.2ml 1-octyl group-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.6ml hexa-methylene-1, and the 6-vulcabond is at 70 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 28 hours, use acetone and washing with alcohol successively after reducing to room temperature, 70 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 17:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 1.1g, succsinic acid 0.7g, urea 0.7g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 8h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.7g, add H
2O and EtOH volume ratio are in 4 the mixed solvent, and ultra-sonic dispersion 40min stirs and adds NH down
3.H
2O is adjusted to pH=10, adds the 1.75ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 9h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 80 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.7g joins in the 70ml DMSO 99.8MIN., and the back adds 1.4ml 1-nonyl-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.7ml hexa-methylene-1, and the 6-vulcabond is at 80 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 32 hours, use acetone and washing with alcohol successively after reducing to room temperature, 80 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 18:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 1.2g, succsinic acid 0.8g, urea 0.8g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 8h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.8g, add H
2O and EtOH volume ratio are in 4 the mixed solvent, and ultra-sonic dispersion 40min stirs and adds NH down
3.H
2O is adjusted to pH=10, adds the 2ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 10h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 80 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.8g joins in the 80ml DMSO 99.8MIN., and the back adds 1.6ml1-decyl-3-Methylimidazole-L-proline salt ionic liquid, behind the ultra-sonic dispersion, adds 0.8ml hexa-methylene-1, and the 6-vulcabond is at 80 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 36 hours, use acetone and washing with alcohol successively after reducing to room temperature, 80 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 19:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 1.3g, succsinic acid 0.9g, urea 0.9g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 9h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.9g, add H
2O and EtOH volume ratio are in 5 the mixed solvent, and ultra-sonic dispersion 50min stirs and adds NH down
3.H
2O is adjusted to pH=10, adds the 2.25ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 11h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 90 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.9g joins in the 90ml DMSO 99.8MIN., and the back adds 1.8ml1-ethyl-3-Methylimidazole-L-lactate ions liquid, behind the ultra-sonic dispersion, adds 0.9ml hexa-methylene-1, and the 6-vulcabond is at 90 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 40 hours, use acetone and washing with alcohol successively after reducing to room temperature, 90 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 20:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 1.4g, succsinic acid 0.9g, urea 0.9g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 9h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.9g, add H
2O and EtOH volume ratio are in 5 the mixed solvent, and ultra-sonic dispersion 50min stirs and adds NH down
3.H
2O is adjusted to pH=10, adds the 2.25ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 11h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 90 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.9g joins in the 90ml DMSO 99.8MIN., and the back adds 1.8ml 1-propyl group-3-Methylimidazole-L-lactate ions liquid, behind the ultra-sonic dispersion, adds 0.9ml hexa-methylene-1, and the 6-vulcabond is at 90 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 40 hours, use acetone and washing with alcohol successively after reducing to room temperature, 90 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 21:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 0.5g, succsinic acid 0.1g, urea 0.1g is dissolved in 30ml1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 5h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.1g, add H
2O and EtOH volume ratio are in 1 the mixed solvent, and ultra-sonic dispersion 10min stirs and adds NH down
3.H
2O is adjusted to pH=9, adds the 0.25ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 4h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 50 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.1g joins in the 100ml DMSO 99.8MIN., and the back adds 0.2ml 1-butyl-3-Methylimidazole-L-lactate ions liquid, behind the ultra-sonic dispersion, adds 0.1ml hexa-methylene-1, and the 6-vulcabond is at 50 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 12 hours, use acetone and washing with alcohol successively after reducing to room temperature, 50 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 22:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 0.8g, succsinic acid 0.3g, urea 0.2g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 6h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.3g, add H
2O and EtOH volume ratio are in 2 the mixed solvent, and ultra-sonic dispersion 30min stirs and adds NH down
3.H
2O is adjusted to pH=9, adds the 0.75ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 6h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 60 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.25g joins in the 50ml DMSO 99.8MIN., and the back adds 0.6ml 1-heptyl-3-Methylimidazole-L-lactate ions liquid, behind the ultra-sonic dispersion, adds 0.3ml hexa-methylene-1, and the 6-vulcabond is at 60 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 20 hours, use acetone and washing with alcohol successively after reducing to room temperature, 60 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 23:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 1.1g, succsinic acid 0.5g, urea 0.5g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 7h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.5g, add H
2O and EtOH volume ratio are in 3 the mixed solvent, and ultra-sonic dispersion 40min stirs and adds NH down
3.H
2O is adjusted to pH=10, adds the 1.5ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 8h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 70 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.5g joins in the 70ml DMSO 99.8MIN., and the back adds 1.2ml 1-ethyl-3-Methylimidazole-L-lactate ions liquid, behind the ultra-sonic dispersion, adds 0.7ml hexa-methylene-1, and the 6-vulcabond is at 70 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 28 hours, use acetone and washing with alcohol successively after reducing to room temperature, 80 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 24:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 1.3g, succsinic acid 0.8g, urea 0.7g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 8h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.8g, add H
2O and EtOH volume ratio are in 4 the mixed solvent, and ultra-sonic dispersion 40min stirs and adds NH down
3.H
2O is adjusted to pH=10, adds the 1.8ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 10h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 80 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.7g joins in the 80ml DMSO 99.8MIN., and the back adds 1.6ml 1-ethyl-3-Methylimidazole-L-lactate ions liquid, behind the ultra-sonic dispersion, adds 0.8ml hexa-methylene-1, and the 6-vulcabond is at 80 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 36 hours, use acetone and washing with alcohol successively after reducing to room temperature, 100 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Embodiment 25:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 1.5g, succsinic acid 1g, urea 1g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 10h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
41g adds H
2O and EtOH volume ratio are in 5 the mixed solvent, and ultra-sonic dispersion 50min stirs and adds NH down
3.H
2O is adjusted to pH=10, adds the 2.5ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 12h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind 100 ℃ of vacuum dryings
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 1g joins in the 100ml DMSO 99.8MIN., and the back adds 2ml 1-octyl group-3-Methylimidazole-L-lactate ions liquid, behind the ultra-sonic dispersion, adds 1ml hexa-methylene-1, and the 6-vulcabond is at 100 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 48 hours, use acetone and washing with alcohol successively after reducing to room temperature, 100 ℃ of vacuum dryings promptly obtain product chiral imidazole ionic liquid magnetic nano-particle.
Claims (4)
1. chiral ionic liquid magnetic nano-particle, its structural formula does;
Wherein,
Represent Fe
3O
4Magnetic nano-particle;
Represent coated Si O
2The silicon shell;
Represent coated Si O
2The Fe of silicon fiml
3O
4Magnetic nano-particle; R
1Be selected from C
1-C
16Alkyl; Or
Wherein,
Represent Fe
3O
4Magnetic nano-particle;
Represent coated Si O
2The silicon shell;
Represent coated Si O
2The Fe of silicon fiml
3O
4Magnetic nano-particle; R
2Be selected from C
1-C
16Alkyl.
2. the preparation method of the described chiral ionic liquid magnetic nano-particle of claim 1 is characterized in that:
(1) Fe
3O
4The preparation of magnetic nano-particle: with FeCl
3.6H
2O 0.5-1.5g, succsinic acid 0.1-1g, urea 0.1-1g is dissolved in 30ml 1; In the 2-Ucar 35, put into the 50ml reaction kettle in 200 ℃ of reaction 5-10h, after the cooling respectively with ethanol and deionized water ultrasonic give a baby a bath on the third day after its birth inferior; Use externally-applied magnetic field to separate, promptly obtain Fe with preserving behind the ethanol ultra-sonic dispersion at last
3O
4Magnetic nano-particle;
(2) Fe
3O
4/ SiO
2The preparation of composite magnetic nanoparticle: weighing the first step product F e
3O
40.1-1g, add H
2O and EtOH volume ratio are in the mixed solvent of 1-5, and ultra-sonic dispersion 10-50min stirs adding NH down
3.H
2O is adjusted to pH=9-10, adds the 0.25-2.5ml tetraethoxy in solution, regulates pH=7 with the HCl aqueous solution behind the insulation reaction 4-12h, uses externally-applied magnetic field to separate, and with deionized water and EtOH washing, obtains product F e behind the 50-100 ℃ of vacuum drying
3O
4/ SiO
2
(3) preparation of chiral ionic liquid magnetic nano-particle: with the Fe that makes
3O
4/ SiO
2Composite magnetic nanoparticle 0.1g-1g joins in the 30-100ml DMSO 99.8MIN.; The back adds 0.2-2ml1-alkyl-3-Methylimidazole-L-proline salt or 1-alkyl-3-Methylimidazole-L-lactate ions liquid; Behind the ultra-sonic dispersion; Add 0.1-1ml hexa-methylene-1, the 6-vulcabond is at 50-100 ℃, mechanical stirring, logical N
2Reaction conditions refluxed 12-48 hour, use acetone and washing with alcohol successively after reducing to room temperature, 50-100 ℃ of vacuum drying promptly obtains product chiral imidazole ionic liquid magnetic nano-particle, alkyl is selected from C
1-C
16Alkyl.
3. the application of the described chiral ionic liquid magnetic nano-particle of claim 1 is characterized in that: use the chiral ionic liquid magnetic nano-particle, racemic compound is carried out chiral separation.
4. the application of the described chiral ionic liquid magnetic nano-particle of claim 3 is characterized in that: the chiral ionic liquid magnetic nano-particle, carry out chiral separation to 1-phenyl-1,1-hydroxyl acenaphthene.
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| CN104909414A (en) * | 2015-06-09 | 2015-09-16 | 天津大学 | SiO2-Fe3O4 nano-particles prepared by ultrasonic-assisted method and preparation method |
| CN106540749A (en) * | 2016-10-17 | 2017-03-29 | 吉林化工学院 | A kind of magnetic resolving agent and preparation method thereof |
| CN111530431A (en) * | 2018-11-30 | 2020-08-14 | 北京化工大学 | Magnetic super-crosslinked organic polymer material, preparation method and application |
| CN113368834A (en) * | 2020-02-25 | 2021-09-10 | 中国石油化工股份有限公司 | Composite magnetic nano particle and preparation method and application thereof |
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