CN104403040B - Ion exchange resin - Google Patents
Ion exchange resin Download PDFInfo
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- CN104403040B CN104403040B CN201410513260.9A CN201410513260A CN104403040B CN 104403040 B CN104403040 B CN 104403040B CN 201410513260 A CN201410513260 A CN 201410513260A CN 104403040 B CN104403040 B CN 104403040B
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Abstract
The invention provides ion exchange resin, which is obtained by reacting nonporous styrene-divinyl benzene resin with epoxide group or halogenation group on surface and a compound possessing a formula (I). According to the invention, a function group of ion exchange resin can be obtained by grafting epoxide group or halogenation group on ion exchange resin and the compound possessing the formula (I), then the anion coating resin with completely covered surface, and the resin has high resolution and recovery rate for separation of chiral carbon nanotube. The experiment result shows that the resin of the present invention has more than 90% of recovery rate for separation of chiral carbon nanotube.
Description
Technical field
The present invention relates to analysis technical field, more particularly, to a kind of ion exchange resin.
Background technology
CNT is artificial three-dimensional carbon crystallization, and crystal has different diameter and helicity.CNT has uniqueness
Mechanical, hot, optics and Electronic Performance.CNT is constituted simply, is the carbon atom being covalently attached under various column structures
Hexagonal network thing.Wherein, the Electronic Performance of SWCN (SWNTs) is very quick to the fine difference on geometry
Sense, therefore the nanotube for having fine difference in form is likely to show different band gaps, or close metal, or be close to and partly lead
Body.Although being readily available on these elasticity theories, produce nanotube all methods obtain is semiconductor type
With the mixture of metalline type.And above-mentioned poor controllability limits it in ultra micro electronics (ultra-miniaturized
Electronics the application) and in photoelectronics.
Metal tube and transistor can be separated using the difference of physics and chemistry, but by chiral index, and spiral
Property and further separation of the diameter to transistor it is more difficult because diameter and the physics caused by helicity angle change and/
Or the difference of chemistry is that naked eyes are difficult to discover, the difference of pipe range can become the principal element of physical separation method.Therefore, institute
The method for having known manufacture nanotube can only produce the mixture with different Chiral properties pipes.This is to including Subminiature electronic
Equipment and photoelectricity cause a huge obstacle in interior basic research and application, because in these research field nanometer management and control
The good electronic property of system is necessary.
Prior art has been disclosed the ionic energy transfer of numerous DNA SWCNs (SWCNTs).Such as, doctor Zheng and
DNA sequence motifs for structure-specific recognition and disclosed in its partner
What separation of carbon nanotube pointed out that they utilize be Biochroms companies of the U.S. (Lafayette,
Indiana ion-exchange chromatography).These chromatographic columns are that designed, therefore these chromatographic columns are separated for DNA oligonucleotides
It is poor to the separating effect of SWCN (SWCNTs).For example, although doctor Zheng and its partner can observe
To the pipe of two different-diameters difference Chiral properties, (9,1) and (6,5) between the temporal difference of precipitation, but due to having
The resolution ratio of limit they obtain never during first separation two kinds enrichment cuts.Ion to Biochroms companies
The rate of recovery is also a big problem for exchange chromatography post.Through calculating, only 30% injection raw material is from ion-exchange chromatography
Reclaim in post, remaining 70% is irreversibly adsorbed on chromatography column resin.This chromatographic column can only keep efficiency about to exist
The sample introduction of 20 times or so.So the life-span of this ion-exchange chromatography is very short.
The content of the invention
In view of this, the technical problem to be solved in the present invention is to provide a kind of ion exchange resin, what the present invention was provided
The chromatographic column that ion exchange resin is prepared carries out the separation of Chiral carbon nanotube and has high-recovery.
The invention provides a kind of ion exchange resin, the non-porous benzene second with epoxide group or halogenated group by surface
Alkene-divinylbenzene resin and the reaction of the compound with formula (I) molecular formula are obtained；
HNR1R2
Formula (I)；
Wherein, R1、R2It is independently selected from hydrogen, the alkyl of C1～C15 or C1～C15 and replaces alkyl, the replacement alkyl
Substituent be selected from C6～C12 aryl, hydroxyl, C1～C8 alkylamino radicals or the heterocyclic radical containing 3～8 annular atoms；The R1、R2
In at most have one for H..
Preferably, the R1、R2It is independently selected from hydrogen, the alkyl of C1～C13 or C1～C13 and replaces alkyl, it is described to take
The substituent of substituted alkyl is selected from C6～C12 aryl, hydroxyl, C2～C8 alkylamino radicals or the heterocyclic radical containing 4～6 annular atoms；Institute
State R1、R2In at most have one for H., the heterocyclic radical is selected from azacyclo- and/or oxa- ring.
Preferably, the compound of formula (I) molecular formula is selected from diethylamine, dibutyl amine, two n-hexylamines, octylame, 4- phenyl
Butylamine, monoethanolamine, diethanol amine, 2- (ethylamino) ethanol, N, N- diethyl ethylenediamines, Pehanorm, 3- (diethyl aminos
Base) propylamine, N, N- dimethyl Asia dipropyl triamine, N- (3'- Propylaminos) -2-Pyrrolidone, N- methyl -2- (2- pyridine radicals) second
One or more in amine, morpholine, 4- (2- amino-ethyls) morpholine, piperidines and 1- (2- amino-ethyls) piperidines.
The invention provides a kind of preparation method of ion exchange resin, including：
Non-porous styrene-divinylbenzene resin of the surface with epoxide group or halogenated group and with formula (I) molecule
The compound of formula reacts obtain in a solvent；
HNR1R2
Formula (I)；
Wherein, R1、R2It is independently selected from hydrogen, the alkyl of C1～C15 or C1～C15 and replaces alkyl, the replacement alkyl
Substituent be selected from C6～C12 aryl, hydroxyl, C1～C8 alkylamino radicals or the heterocyclic radical containing 3～8 annular atoms；The R1、R2
In at most have one for H..
Preferably, the reaction temperature is 0 DEG C～100 DEG C, and the reaction time is 0.1～48h.
Preferably, the surface carries the non-porous styrene-divinylbenzene resin of epoxide group and with formula (I) molecule
The mass ratio of the compound of formula is (0.01～100)：1.
Preferably, the solvent includes organic solvent and water.
Preferably, the volume ratio of the organic solvent and water is (1～3)：(3～1).
The invention provides a kind of ion-exchange chromatography, the ion exchange resin or aforesaid right by described in aforesaid right
It is required that the ion exchange resin that the preparation method of described ion exchange resin is prepared is prepared.
Present invention also offers a kind of separation method of Chiral carbon nanotube, including：Using described in the claims
Ion exchange resin, aforesaid right will be described ion exchange resin the ion exchange resin for preparing of preparation method or on
State the ion-exchange chromatography described in claim to be separated.
Compared with prior art, the invention provides a kind of ion exchange resin, by surface epoxide group or halogenation are carried
The non-porous styrene-divinylbenzene resin of group and the reaction of the compound with formula (I) molecular formula are obtained.What the present invention was provided
The ion that epoxide group or halogenated group on ion exchange resin is obtained with the grafting compounds reaction with formula (I) molecular formula
The functional group of exchanger resin, forms the resin of the anion coating of surface all standing, and the resin divides for Chiral carbon nanotube
From with high-resolution and the rate of recovery.Test result indicate that, the resin of the present invention is big for the separation of Chiral carbon nanotube has
In 90% rate of recovery.
Description of the drawings
Fig. 1 is the precipitation chromatogram of the DNA SWCNs (SWCNTs) of the chromatographic column that the embodiment of the present invention 5 is provided；
Fig. 2 is the DNA single-wall carbon nanotube composite UV-visible spectrums that the embodiment of the present invention 7 is provided.
Specific embodiment
The invention provides a kind of ion exchange resin, the non-porous benzene second with epoxide group or halogenated group by surface
Alkene-divinylbenzene resin and the reaction of the compound with formula (I) molecular formula are obtained；
HNR1R2
Formula (I)；
Wherein, R1、R2It is independently selected from hydrogen, the alkyl of C1～C15 or C1～C15 and replaces alkyl, the replacement alkyl
Substituent be selected from C6～C12 aryl, hydroxyl, C1～C8 alkylamino radicals or the heterocyclic radical containing 3～8 annular atoms；The R1、R2
In at most have one for H.；Preferably, the R1、R2It is independently selected from hydrogen, the alkyl of C1～C13 or C1～C13 and replaces alkane
Base, the substituent of the replacement alkyl is selected from C6～C12 aryl, hydroxyl, C2～C8 alkylamino radicals or containing 4～6 annular atoms
Heterocyclic radical；The R1、R2In at most have one for H., the heterocyclic radical is selected from azacyclo- and/or oxa- ring.
It is furthermore preferred that the compound of formula (I) molecular formula is selected from diethylamine, dibutyl amine, two n-hexylamines, octylame, 4- benzene
Base butylamine, monoethanolamine, diethanol amine, 2- (ethylamino) ethanol, N, N- diethyl ethylenediamines, Pehanorm, 3- (diethyl
Amino) propylamine, N, N- dimethyl Asia dipropyl triamine, N- (3'- Propylaminos) -2-Pyrrolidone, N- methyl -2- (2- pyridine radicals)
One or more in ethamine, morpholine, 4- (2- amino-ethyls) morpholine, piperidines and 1- (2- amino-ethyls) piperidines.
The present invention is for non-porous styrene-divinylbenzene resin of the surface with epoxide group or halogenated group
Source is not limited, and the halogenated group can be chlorine or bromine.Preferably commercially available, such as Sai Fen Science and Technology Ltd.s are commercially available
The non-porous SDVB of epoxide group, trade name：Epoxy resin (Sepax
Technologies,Inc.,Newark,Delaware,USA).Non-porous SDVB tree with halogenated group
Fat, trade name：-Cl,-Br(Sepax Technologies,Inc.,Newark,
Delaware,USA)。
The present invention for the diethylamine, dibutyl amine, two n-hexylamines, octylame, 4- phenyibutylamines, monoethanolamine, diethanol amine,
2- (ethylamino) ethanol, N, N- diethyl ethylenediamines, Pehanorm, 3- (diethylamino) propylamine, N, N- dimethyl is sub-
Dipropyl triamine, N- (3'- Propylaminos) -2-Pyrrolidone, N- methyl -2- (2- pyridine radicals) ethamine, morpholine, 4- (2- amino second
Base) morpholine, the source of piperidines and 1- (2- amino-ethyls) piperidines and purity is not defined, and commercially available chromatographically pure standard items are
Can, it is preferably selected from the purchase of Sigma-Aldrich companies.
The invention provides a kind of preparation method of ion exchange resin, including：
Non-porous styrene-divinylbenzene resin of the surface with epoxide group or halogenated group and with formula (I) molecule
The compound of formula reacts obtain in a solvent；
HNR1R2
Formula (I)；
Wherein, R1、R2It is independently selected from hydrogen, the alkyl of C1～C15 or C1～C15 and replaces alkyl, the replacement alkyl
Substituent be selected from C6～C12 aryl, hydroxyl, C1～C8 alkylamino radicals or the heterocyclic radical containing 3～8 annular atoms；The R1、R2
In at most have one for H。；
Preferably, the R1、R2It is independently selected from hydrogen, the alkyl of C1～C13 or C1～C13 and replaces alkyl, it is described to take
The substituent of substituted alkyl is selected from C6～C12 aryl, hydroxyl, C2～C8 alkylamino radicals or the heterocyclic radical containing 4～6 annular atoms；Institute
State R1、R2In at most have one for H。, the heterocyclic radical is selected from azacyclo- and/or oxa- ring.
It is furthermore preferred that the compound of formula (I) molecular formula is selected from diethylamine, dibutyl amine, two n-hexylamines, octylame, 4- benzene
Base butylamine, monoethanolamine, diethanol amine, 2- (ethylamino) ethanol, N, N- diethyl ethylenediamines, Pehanorm, 3- (diethyl
Amino) propylamine, N, N- dimethyl Asia dipropyl triamine, N- (3'- Propylaminos) -2-Pyrrolidone, N- methyl -2- (2- pyridine radicals)
One or more in ethamine, morpholine, 4- (2- amino-ethyls) morpholine, piperidines and 1- (2- amino-ethyls) piperidines.
The present invention is for non-porous styrene-divinylbenzene resin of the surface with epoxide group or halogenated group
Source is not limited, preferably commercially available, such as Sai Fen Science and Technology Ltd.s.
The present invention for the diethylamine, dibutyl amine, two n-hexylamines, octylame, 4- phenyibutylamines, monoethanolamine, diethanol amine,
2- (ethylamino) ethanol, N, N- diethyl ethylenediamines, Pehanorm, 3- (diethylamino) propylamine, N, N- dimethyl is sub-
Dipropyl triamine, N- (3'- Propylaminos) -2-Pyrrolidone, N- methyl -2- (2- pyridine radicals) ethamine, morpholine, 4- (2- amino second
Base) morpholine, the source of piperidines and 1- (2- amino-ethyls) piperidines and purity is not defined, and commercially available chromatographically pure standard items are
Can, it is preferably selected from the purchase of Sigma-Aldrich companies.
In the present invention, non-porous styrene-divinylbenzene resin of the surface with epoxide group or halogenated group
1 is preferably with the mass ratio of the compound with formula (I) molecular formula：(0.1～4), more preferably 1：(0.12～3.7).
In the present invention, the solvent includes organic solvent and water.The present invention is not defined for the organic solvent,
Conventional organic solvent well known to those skilled in the art, preferably tetrahydrofuran, DMF, DMSO, Dioxane, acetone, second
One kind in alcohol, chloroform and dichloroethanes.
In the present invention, the volume ratio of the organic solvent and water is (1～3)：(3～1), more preferably (2～3)：(3
～2).
In the present invention, non-porous styrene-divinylbenzene resin of the surface with epoxide group or halogenated group
Quality and solvent volume ratio be (0.01～100)：1, more optimized proportion is (0.1～10)：1.
In the present invention, the reaction temperature is preferably 0 DEG C～100 DEG C, more preferably 10 DEG C～80 DEG C, and most preferably 20
DEG C～30 DEG C.The reaction time is preferably greater than 0.1h, most preferably more preferably 0.1～48h, 8～20h.
After obtaining ion exchange resin, filter preferably through after stirring.The present invention is for the stirring and filter type not
It is defined, conventional stirring and filter type in analytical chemistry well known to those skilled in the art.
The resin also includes after filtering, preferably the step of washing.In we are bright, the washing preferably washing and
Organic solvent washing after organic solvent washing, more preferably washing, acid reaction.The organic solvent is preferably acetone.The acid
Preferably sulfuric acid, the concentration of the sulfuric acid is preferably 0.4～1M.
Most preferably, the washing is concretely comprised the following steps：After washing acetone wash, be dried, stirring in water bath, mistake after acid reaction
Filter, then washing, acetone washing.The temperature of the water-bath is 35～45 DEG C.The drying is preferably dried in atmosphere.It is described
Acid is preferably sulfuric acid.
The epoxide group on ion exchange resin or halogenated group and the chemical combination with formula (I) molecular formula that the present invention is provided
The functional group of the ion exchange resin that thing graft reaction is obtained, forms the resin of the anion coating of surface all standing, the resin
For the separation of Chiral carbon nanotube has high-resolution and the rate of recovery.
The invention provides a kind of ion-exchange chromatography, the ion exchange resin or aforesaid right by described in aforesaid right
It is required that the ion exchange resin that the preparation method of described ion exchange resin is prepared is prepared.
The preparation method of the ion-exchange chromatography that the present invention is provided is preferably the amberlite that the present invention is prepared
Fat is filled in form of slurry in chromatographic column.It is specifically as follows：CNTion WAX ion exchange resin prepared by synthesis technique
Chromatographic column is loaded into using homogenate method, particle diameter is 10 μm.CNTion WAX resins make 1.0M sodium acid carbonate slurry solutions,
Under 5000psi pressure, in being filled into the liquid-phase chromatographic column of 7.5x75mm.
The present invention is not defined for the model and specification of the chromatographic column, well known to those skilled in the art for color
The chromatographic column of detached model and specification is composed, such as can be the chromatographic column of 7.8*75mm.
Present invention also offers a kind of separation method of Chiral carbon nanotube, including：Using described in the claims
Ion exchange resin, aforesaid right will be described ion exchange resin the ion exchange resin for preparing of preparation method or on
State the ion-exchange chromatography described in claim to be separated.
In the present invention, it is preferred to, the test and analysis of chromatographic column adopt the liquid chromatographs of Agilent HPLC 120, inspection
Mark sample is using the mixed of natrium nitrosum (0.06 gram per milliliter), adenylate (0.5 gram per milliliter) and guanylic acid (1.5 grams per milliliter)
Close solution.Mobile phase A:10mM Tris, pH=8；Mobile phase B：A+0.1M NaCl. are using isocyatic mobile phase A or wait
Mixed flow phase A and B of concentration is carrying out quality testing analysis.The chromatogram point of the SWCN (SWCNTs) of DNA parcels
Ultraviolet-visible near infrared spectrum is adopted from each component analysis of liquid chromatogram instrument, chromatogram purification is adopted with Fraction collection.
In the present invention, the source of the nanotube and DNA is not defined, can is commercially available, such as from Southwest
The CoMoCAT nanotubes of Nanotechnologies purchases.Single stranded DNA is from Integrated DNA Technologies, Inc.
(Coralville, IA) is customized.
In the present invention, the dispersion of CNT and separation are according to Zheng, M., et al., DNA-assisted dispersion
Method in the document that and separation of carbon nanotubes.Nat Mater.2003.2,338-342 are delivered
Carry out.
In order to further illustrate the present invention, the ion exchange resin to present invention offer and its preparation with reference to embodiments
Method is described in detail.
Embodiment 1
5g with epoxide group non-porous styrene-divinylbenzene resin (Epoxy, 10um particle diameter)
It is suspended in 50mL tetrahydrofurans and water (1：1) in mixed liquor, 1g 3- (diethylin) propylamine is added, obtains mixture.Mixing
Thing is filtered after being stirred at room temperature 16 hours.The resin of collection is washed with water to neutrality, washes 3 times with 30mL acetone afterwards.Resin exists
The sulfuric acid of 1M is added after air drying, is stirred 1 hour under 40 DEG C of waters.Filter mixed liquor is simultaneously washed with water to neutrality, it
Wash 3 times with 15mL acetone afterwards.The final ion exchange resin product 5.02g that air drying is collected after 16 hours.
Embodiment 2
5g with epoxide group non-porous styrene-divinylbenzene resin (Epoxy, 10um particle diameter)
It is suspended in 50mL tetrahydrofurans and water (1：1) in mixed liquor, 0.7g Isosorbide-5-Nitraes-oxygen azo-cycle hexane (morphine beautiful jade) is added, is mixed
Compound.Mixture is filtered after being stirred at room temperature 16 hours.The resin of collection is washed with water to neutrality, washes 3 with 30mL acetone afterwards
It is secondary.Resin adds the sulfuric acid of 1M after being dried in atmosphere, stir 1 hour under 40 DEG C of waters.Filter mixed liquor is simultaneously washed with water
To neutral, 3 times are washed with 15mL acetone afterwards.The final ion exchange resin product 5.01g that air drying is collected after 16 hours.
Embodiment 3
5g with epoxide group non-porous styrene-divinylbenzene resin (Epoxy, 10um particle diameter)
It is suspended in 50mL tetrahydrofurans and water (1：1) in mixed liquor, 1.5g N- (3'- Propylaminos) -2-Pyrrolidone is added, is obtained
Mixture.Mixture is filtered after being stirred at room temperature 16 hours.The resin of collection is washed with water to neutrality, is washed with 30mL acetone afterwards
3 times.Resin adds the sulfuric acid of 1M after being dried in atmosphere, stir 1 hour under 40 DEG C of waters.Filter mixed liquor is simultaneously washed with water
To neutral, 3 times are washed with 15mL acetone afterwards.The final ion exchange resin product 5.02g that air drying is collected after 16 hours.
Embodiment 4
5g with epoxide group non-porous styrene-divinylbenzene resin (Epoxy, 10um particle diameter)
It is suspended in 50mL diethylamine and water (1：1) in mixed liquor, mixture is filtered after stirring 16 hours under 60 DEG C of oil baths.Collect
Resin is water washed with 100mL, washes 3 times with 30mL acetone afterwards.Resin adds the sulfuric acid of 1M after being dried in atmosphere, at 40 DEG C
Stir 1 hour under waters.Filter mixed liquor is simultaneously washed with water to neutrality, washes 3 times with 15mL acetone afterwards.Air drying 16 hours
The final ion exchange resin product 5.12g for collecting afterwards.
Embodiment 5
CNTion WAX ion exchange resin prepared by embodiments in accordance with the present invention 4 loads into chromatogram using homogenate method
Post, particle diameter is 10 μm.CNTion WAX resins make 1.0M sodium acid carbonate slurry solutions, under 5000psi pressure, are filled into
7.5x75mm liquid-phase chromatographic column in.
Embodiment 6
The chiral separation of SWCN is carried out using the ion-exchange chromatography of embodiment 5.Comprise the following steps that：From
The CoMoCAT nanotubes of Southwest Nanotechnologies, Inc. (USA) purchase.Single stranded DNA is from Integrated
DNA Technologies, Inc. (Coralville, IA, USA) are customized.The dispersion and separation of CNT is according to Zheng, M., et
al.,DNA-assisted dispersion and separation of carbon nanotubes.Nat
Method in the document that Mater.2003.2,338-342 is delivered is carried out.The ion-exchange chromatography of d (GT) 20-CNT compounds is such as
Shown in Fig. 1, Fig. 1 is the precipitation chromatogram of the DNA SWCNs (SWCNTs) of the chromatographic column that the embodiment of the present invention 5 is provided.
It is absorption of the eluent in 300nm by can be seen that a lines in Fig. 1.The concentration of d (GT) 20- dispersing Nano carbon tubes is 400 μ g/
ML, sample size is 500 μ L, and mobile phase A is the mixed liquor of 0.03M sodium citrates and 0.3M NaCl, and Mobile phase B is A and 1M
NaSCN mixed liquors.Salting liquid gradient elution is 0-0.9MNaSCN, and flow velocity is 2mL/min, co-elute 80mL.In units of 2mL
Part between collecting 0 to 20 minutes.
Embodiment 7
The component that embodiment 6 is collected is analyzed, as a result as shown in Fig. 2 Fig. 2 is the DNA that the embodiment of the present invention 7 is provided
The single-wall carbon nanotube composite UV-visible spectrum of parcel.CoMoCAT pipes have two kinds of semiconductor types (6,5) and (7,
5).What is represented in Fig. 2 is the absorption curve of 7 elution fractions (a1-a2 and a3-a7).Component a1 and a2 are in 990nm and 574nm
There are two major absorbance peaks.(6,5) 975nm (E11) and 567nm (E22) of pipe is close to, but red shift in this and document.From component
A3 to a7 can see second initiation material (7,5) pipe (E11=1040nm, E22=653nm), but be not present in component
In a1 and a2.These data explanation WAX posts can separate (6,5) with (7,5) pipe.(6,5) that component a2 contains high concentration are single
Wall carbon nano tube, the component of collection has finally been diluted 10 times can just carry out ultraviolet-visible analysis.Illustrated by above-mentioned data, it is right
Two kinds in parent material CoMoCAT have a main component of different helicities, and the ion exchange resin of present invention synthesis can be with
It is isolated.Quantitative analysis results show that ion-exchange chromatography of the present invention has reached 90% rate of recovery.
Embodiment 8
6g with cl radical reactive resin (- Cl) it is suspended in 60mL diethylamine and water (1：1) mixed
In closing liquid.Mixture is filtered after stirring 16 hours under 60 DEG C of oil baths.The resin of collection is water washed with 100mL, and 30mL is used afterwards
Acetone washes 3 times.Resin adds the sulfuric acid of 0.5M after being dried in atmosphere, stir 1 hour under 40 DEG C of waters.Filter mixed liquor
And wash with water to neutrality, wash 3 times with 15mL acetone afterwards.The final ion exchange resin that air drying is collected after 16 hours is produced
Thing 6.1g.
The above is only the preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, under the premise without departing from the principles of the invention, some improvements and modifications can also be made, these improvements and modifications also should
It is considered as protection scope of the present invention.
Claims (8)
1. a kind of separation method of Chiral carbon nanotube, including：Carried out point using ion exchange resin or ion-exchange chromatography
From；The ion-exchange chromatography is prepared by ion exchange resin；
The ion exchange resin, the non-porous styrene-divinylbenzene resin with epoxide group or halogenated group by surface
Obtain with the reaction of the compound with formula (I) molecular formula；
HNR1R2
Formula (I)；
Wherein, R1、R2It is independently selected from hydrogen, the alkyl of C1～C15 or C1～C15 and replaces alkyl, the replacement alkyl takes
Dai Ji is selected from C6～C12 aryl, hydroxyl, C1～C8 alkylamino radicals or the heterocyclic radical containing 3～8 annular atoms；The R1、R2In extremely
There is one for H more.
2. separation method according to claim 1, it is characterised in that the R1、R2It is independently selected from hydrogen, C1～C13
Alkyl or C1～C13 replace alkyl, the substituent of the replacement alkyl to be selected from C6～C12 aryl, hydroxyl, C2～C8 alkylamino radicals
Or the heterocyclic radical containing 4～6 annular atoms；The R1、R2In at most have one for H, the heterocyclic radical selected from azacyclo- and/or
Oxa- ring.
3. separation method according to claim 1, it is characterised in that the compound of formula (I) molecular formula is selected from diethyl
Amine, dibutyl amine, two n-hexylamines, octylame, 4- phenyibutylamines, monoethanolamine, diethanol amine, 2- (ethylamino) ethanol, N, N- diethyl
Ethylenediamine, Pehanorm, 3- (diethylamino) propylamine, N, N- dimethyl Asia dipropyl triamine, N- (3'- Propylaminos)-
2-Pyrrolidone, N- methyl -2- (2- pyridine radicals) ethamine, morpholine, 4- (2- amino-ethyls) morpholine, piperidines and 1- (2- amino second
Base) one or more in piperidines.
4. separation method according to claim 1, it is characterised in that the preparation method of the ion exchange resin, including：
Non-porous styrene-divinylbenzene resin of the surface with epoxide group or halogenated group and with formula (I) molecular formula
Compound reacts obtain in a solvent
HNR1R2
Formula (I)；
Wherein, R1、R2It is independently selected from hydrogen, the alkyl of C1～C15 or C1～C15 and replaces alkyl, the replacement alkyl takes
Dai Ji is selected from C6～C12 aryl, hydroxyl, C1～C8 alkylamino radicals or the heterocyclic radical containing 3～8 annular atoms；The R1、R2In extremely
There is one for H more.
5. separation method according to claim 4, it is characterised in that the reaction temperature is 0 DEG C～100 DEG C, it is described anti-
It is 0.1～48h between seasonable.
6. separation method according to claim 4, it is characterised in that the surface is with epoxide group or halogenated group
The mass ratio of non-porous styrene-divinylbenzene resin and the compound with formula (I) molecular formula is (0.01～100)：1.
7. separation method according to claim 4, it is characterised in that the solvent includes organic solvent and water.
8. separation method according to claim 7, it is characterised in that the volume ratio of the organic solvent and water for (1～
3)：(3～1).
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