CN103551118A - Column [5] aromatic bonding silica gel stationary phase as well as preparation method and application thereof - Google Patents
Column [5] aromatic bonding silica gel stationary phase as well as preparation method and application thereof Download PDFInfo
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- CN103551118A CN103551118A CN201310549876.7A CN201310549876A CN103551118A CN 103551118 A CN103551118 A CN 103551118A CN 201310549876 A CN201310549876 A CN 201310549876A CN 103551118 A CN103551118 A CN 103551118A
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 230000005526 G1 to G0 transition Effects 0.000 title claims abstract description 30
- 239000000741 silica gel Substances 0.000 title claims abstract description 27
- 229910002027 silica gel Inorganic materials 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical group CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 229910003978 SiClx Inorganic materials 0.000 claims description 11
- 239000003292 glue Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- 239000011159 matrix material Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims description 3
- 150000001263 acyl chlorides Chemical class 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 2
- 238000013375 chromatographic separation Methods 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000009471 action Effects 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical group NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000000536 complexating effect Effects 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000004255 ion exchange chromatography Methods 0.000 description 3
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000004986 phenylenediamines Chemical group 0.000 description 2
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000007445 Chromatographic isolation Methods 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- -1 arene compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000012434 mixed-mode chromatography Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BBNQQADTFFCFGB-UHFFFAOYSA-N purpurin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC(O)=C3C(=O)C2=C1 BBNQQADTFFCFGB-UHFFFAOYSA-N 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of chromatographic separation, and particularly relates to a column [5] aromatic bonding silica gel stationary phase, and a preparation method and application thereof. The column [5] aromatic bonding silica gel stationary phase disclosed by the invention has the characteristics of high bonding amount, stable bonding layer and low cost, and is simple and convenient to prepare.
Description
Technical field
The invention belongs to chromatographic separation technology field, particularly a kind of post [5] aromatic hydrocarbons bonded silica gel stationary phase and preparation method thereof and application.
Background technology
Chromatogram is a kind of isolation technics being most widely used now, and its principle is that different component moves with the caused component differential of difference of fixing active force between phase or mobile phase.Chromatographic stationary phases is chromatographic isolation " heart ", and liquid chromatogram has polytype, comprises reverse-phase chromatography (RPLC), normal-phase chromatography (NPLC), HC (HIC), ion-exchange chromatography (IEC) etc.For these traditional fixedly phases, its separating mechanism and pattern are single, mainly rely on mutually the separated apolar substance of hydrophobic effect as reverse-phase chromatography C18 is fixing, and ion-exchange chromatography is by ion exchange isolating ions type compound.In the face of complex sample as character, to form complicated natural products, multi-component while of Food and environment sample separated, fixing that these are traditional suffered from very large challenge mutually, a lot of components cannot obtain complete separation, and this certainly will affect the accurate quantitative analysis of component.Mixed mode chromatogram (Mixed-mode chromatography, MMC) the fixing functional group that comprises mutually two or more, only by changing the character of mobile phase and forming, can obtain different type of separation, be conducive to improve separation selectivity and expand range of application.With traditional fixing comparing of single-mode, mixed mode is fixed has the advantages such as high selectivity, high power capacity, Gao Zhuxiao mutually.Along with the development of supramolecular chemistry, post aromatic hydrocarbons is synthesized as the new macrocycle molecule of a class, and post aromatic hydrocarbons is that by methylene bridge, the contraposition at phenyl ring connects by hydroquinones or Hydroquinone ether, and knot forms a columned class cyclic oligomer.Due to chemistry and the space structure of its uniqueness, post arene compounds combines characteristic and the advantage of multiple existing host compound: post aromatic hydrocarbons has highly symmetrical space structure, and it can be modified and just can identify the guest molecule of ad hoc structure without complexity; The easy decorating sites such as hydroxyl are contained in post aromatic hydrocarbons bridging benzene ring structure both sides, make its chemical modification method be similar to cyclodextrin; In addition, post aromatic hydrocarbons also has special dissolution properties, in organic solvent, can effectively carry out Host-guest Recognition.Post aromatic hydrocarbons has shown good molecular recognition performance, it not only can be identified electron acceptors such as purpurine, pyridiniujm, quaternary ammonium salt and ionic liquids as electron donor, also can and neutral diimidazole alkane guest molecule between by a plurality of C-H π, interact and form stable host-guest complex; From molecular structure, post aromatic hydrocarbons has the action site of potential chromatographic stationary phases, as aromatic ring (hydrophobic effect and π-π effect), phenolic hydroxyl group (hydrogen bond action, dipole-dipole effect), large annulated column chamber (inclusion effect) etc., predictably, if the post aromatic hydrocarbons of usining is applied to Stationary Phase of HPLC as separating medium, to developing the chromatographic stationary phases of the novel high selectivity of a class, the research contents of enriching supramolecular chemistry chromatographic stationary phases has important theory significance and using value.
Summary of the invention
The object of this invention is to provide a kind of post [5] aromatic hydrocarbons bonded silica gel stationary phase; This fixing phase not only has traditional ODS reverse-phase chromatography performance, and multiple action sites such as containing complexing, hydrogen bond action, π-π effect and space coupling can be provided simultaneously.
For solving the problems of the technologies described above, the technical solution used in the present invention is as follows:
[5] an aromatic hydrocarbons bonded silica gel stationary phase, described fixedly phase structure is suc as formula shown in I:
Formula I.
The invention discloses the post aromatic hydrocarbons bonded silica gel stationary phase that a kind of bonded amount is high, bonded layer is stable.It not only has traditional ODS reverse-phase chromatography performance, multiple action sites such as containing complexing, hydrogen bond action, π-π effect and space coupling can be provided simultaneously, thereby to a certain extent can substitute-ODS, also the material of difficult separation provides separated possibility simultaneously.
The present invention also further provides the preparation method of described post [5] aromatic hydrocarbons bonded silica gel stationary phase, decompression after formula II compound acetic acid pilum [5] aromatic hydrocarbons and thionyl chloride backflow is extracted to post [5] aromatic hydrocarbons that thionyl chloride obtains the acyl chlorides activation shown in formula III, then obtain described post [5] aromatic hydrocarbons bonded silica gel stationary phase with the separation and purification in 20-24 hour of inorganic matrix filler room temperature reaction;
Formula II formula III.
Its preparation process can be expressed as:
On described post [5] aroamtic hydrocarbon raw material, lower edge contains acetate.
Described inorganic matrix filler is aminopropyl triethoxysilane SiClx glue.
Aminopropyl triethoxysilane SiClx glue is diameter 5 μ m, and specific area is 250-300m
2the spherical silica gel of/g.
It is 15-20ml that 1g formula II compound adds the volume of thionyl chloride.
Formula III compound reacts in organic solvent with inorganic matrix filler, formula II compound (g): aminopropyl triethoxysilane SiClx glue (g): organic solvent (mL) is preferably 1:3-4:40-70.
Organic solvent can be carrene, chloroform, oxolane etc.
Described separation and purification is: reaction is filtered after stopping, and filter cake is used DMF, water, methyl alcohol, washed with dichloromethane successively, vacuum drying 12-24 h at 60-100 ℃.
Described post [5] aromatic hydrocarbons bonded silica gel stationary phase can be used for the liquid chromatogram separation of organic compound.
In common only need adjusting mobile phase, the ratio of methyl alcohol and water just can meet the compartment analysis requirement of sample.
Compared with prior art, tool has the following advantages in the present invention:
It is higher that post of the present invention [5] aromatic hydrocarbons bonded silica gel stationary phase has bonded amount, and bonded layer is stable, and preparation method is easy, lower-cost feature.
Accompanying drawing explanation
Fig. 1 is Polycyclic Aromatic Hydrocarbon Mixture sample at the fixing chromatographic fractionation figure of going up mutually of the present invention, and the peak that wherein each material is corresponding is number as follows: benzene (1), naphthalene (2), anthracene (3), (4) ， perylenes (5) in the wrong; Mobile phase is methyl alcohol: water=60:40(volume ratio, lower same), detecting wavelength is 254 nm, flow rate of mobile phase is 1 mL/min.
Fig. 2 be aniline and phenylenediamine position different structure mixture at the fixing chromatographic fractionation figure of going up mutually of the present invention, the peak that wherein each material is corresponding is number as follows: ortho-aminotoluene (1), 2,6-dimethylaniline (2), naphthylamines (3), paranitroanilinum (4); Mobile phase is methyl alcohol: water=55:45, and detecting wavelength is 254 nm, and flow rate of mobile phase is 1 mL/min.
Fig. 3 is substituted benzene at the fixing chromatographic fractionation figure of going up mutually of the present invention, and the peak that wherein each material is corresponding is number as follows: toluene (1), ethylbenzene (2), n-proplbenzene (3), n-butyl benzene (4), positive penta benzene (5); Mobile phase is methyl alcohol: water=75:25, and detecting wavelength is 254 nm, and flow rate of mobile phase is 1 mL/min.
The specific embodiment
With specific embodiment, technical scheme of the present invention is described below, but protection scope of the present invention is not limited to this:
Embodiment 1
Post [5] aromatic hydrocarbons bonded silica gel stationary phase, makes by following step:
1) activated silica gel: take a certain amount of Bio-sil and immerse HCl/H
2in O (1:3, v/v), silica gel weight (g) and hydrochloric acid volume (ml) are than being 1:15-1:20; Soak 12 h, the 24-36 h that refluxes under magnetic agitation removes metal ion, then with the sand core funnel of G5, filter, with secondary redistilled water, repeatedly rinse to neutrality, finally use acetone washed twice, at 160 ℃, dry 10 h, to slough surface solvent and water, obtain the activated silica gel of surface uniform distribution hydroxyl, are stored in drier standby.
2) preparation of aminopropyl triethoxysilane SiClx glue (also can adopt commercial goods): N is being housed
2ingress pipe, condenser pipe, CaCl
2in the drying device of drying tube and magnetic agitation, add a certain amount of aminopropyl triethoxysilane, add again dry toluene, under magnetic agitation, (20 r/min) adds activated silica gel at a slow speed, silica gel weight (g): aminopropyl triethoxysilane (ml): dry toluene (ml) is generally: 3-5: 5:45.Be warming up to rapidly 110 ℃-130 ℃, and accelerate mixing speed, at N
2lower 24 h that reflux of protection.Stop reaction, with the sand core funnel of G5, filter, repeatedly, with methyl alcohol, secondary redistilled water, acetone washing, vacuum drying 10 h at 70 ℃, obtain aminopropyl triethoxysilane SiClx glue and are stored in drier standby.
3) N is being housed
2ingress pipe, condenser pipe, CaCl
2in the drying device of drying tube and magnetic agitation, get 800mg carboxyl post [5] aromatic hydrocarbons and 15mL thionyl chloride and add 100mL flask, backflow 2h, decompression is steamed except excess chlorination sulfoxide as far as possible, obtains white solid, and product is not purified can react for next step.Post [5] aromatic hydrocarbons of above-mentioned acyl chlorides activation is dissolved in 50mL anhydrous methylene chloride, add 3g aminopropyl triethoxysilane SiClx glue, after room temperature reaction 24h, add 10mL methyl alcohol to continue reaction 6h, with G5 sand core funnel suction filtration, use successively DMF, water, methyl alcohol, washed with dichloromethane, fixing phase, 60 ℃ of vacuum drying.
The post of preparation of the present invention [5] Arene Stationary Phase and aminopropyl triethoxysilane SiClx glue results of elemental analyses are as shown in table 1 below, wherein bonded amount calculates gained according to carbon element content, by the visible the present invention of table 1 is fixing, there is mutually higher bonded amount, can bonding 70umol post aromatic hydrocarbons above every gram of silica gel.In the scope of mobile phase pH=3-9, repeatedly alternately rinsed four months chromatogram column efficiencies, 7% left and right that declined, the RSD(n=6 that aniline retention time changes) < 2%, this shows under neutrality, weak acid and weak basic condition, the chemical property of post of the present invention [5] aromatic hydrocarbons bonded stationary phase is more stable, and the reappearance of chromatographic column is better.
Table 1
| ? | C% | H% | N% | Bonded amount (umol/g) |
| Aminopropyl triethoxysilane SiClx glue | 5.91 | 1.32 | 1.89 | — |
| Post [5] Arene Stationary Phase | 9.84 | 1.25 | 1.24 | 70 |
Adopting homogenate method, is homogenate with dioxane and carbon tetrachloride (volume ratio is 2:3), does displacement fluid, by prepared fixedly packing in stainless steel tube under 50MPa with methyl alcohol.
Application: fixedly phase of the present invention can be effectively separated for the liquid chromatogram of most of organic compounds, it not only has traditional ODS reverse-phase chromatography performance, multiple action sites such as containing complexing, hydrogen bond action, π-π effect and space coupling can be provided simultaneously, thereby to a certain extent can substitute-ODS, also the material of difficult separation provides separated possibility simultaneously.Fig. 1,2,3 is respectively Polycyclic Aromatic Hydrocarbon Mixture sample, aniline and phenylenediamine position different structure mixture, substituted benzene at the fixing chromatographic fractionation figure of going up mutually of the present invention.
Claims (8)
1. post [5] aromatic hydrocarbons bonded silica gel stationary phase, is characterized in that, described fixedly phase structure is suc as formula shown in I:
Formula I.
2. the preparation method of post [5] aromatic hydrocarbons bonded silica gel stationary phase described in claim 1, it is characterized in that, decompression after formula II compound acetic acid pilum [5] aromatic hydrocarbons and thionyl chloride backflow is extracted to post [5] aromatic hydrocarbons that thionyl chloride obtains the acyl chlorides activation shown in formula III, then obtain described post [5] aromatic hydrocarbons bonded silica gel stationary phase with the separation and purification in 20-24 hour of inorganic matrix filler room temperature reaction;
Formula II formula III.
3. the preparation method of post as claimed in claim 2 [5] aromatic hydrocarbons bonded silica gel stationary phase, is characterized in that, described inorganic matrix filler is aminopropyl triethoxysilane SiClx glue.
4. the preparation method of post as claimed in claim 3 [5] aromatic hydrocarbons bonded silica gel stationary phase, is characterized in that, aminopropyl triethoxysilane SiClx glue is that specific area is 250-300m
2the spherical silica gel of/g.
5. the preparation method of post as claimed in claim 2 [5] aromatic hydrocarbons bonded silica gel stationary phase, is characterized in that, it is 15-20ml that 1g formula II compound adds the volume of thionyl chloride.
6. the preparation method of post as claimed in claim 2 [5] aromatic hydrocarbons bonded silica gel stationary phase, it is characterized in that, formula III compound reacts in organic solvent with inorganic matrix filler, formula II compound (g): aminopropyl triethoxysilane SiClx glue (g): organic solvent (mL) is 1:3-4:40-70.
7. the preparation method of post as claimed in claim 2 [5] aromatic hydrocarbons bonded silica gel stationary phase, it is characterized in that, described separation and purification is: reaction is filtered after stopping, and filter cake is used DMF, water, methyl alcohol, washed with dichloromethane successively, vacuum drying 12-24 h at 60-100 ℃.
8. post claimed in claim 1 [5] aromatic hydrocarbons bonded silica gel stationary phase is separated for the liquid chromatogram of organic compound.
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Cited By (7)
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| CN106622185A (en) * | 2016-12-21 | 2017-05-10 | 郑州大学 | Diazadioxocalix [2] arene [2] triazine bonded silica gel stationary phase as well as preparation method and application thereof |
| US9815764B2 (en) | 2014-09-03 | 2017-11-14 | Northwestern University | Homochiral metal-organic framework with enantiopure pillar[5]arene active domains |
| CN111303084A (en) * | 2020-03-12 | 2020-06-19 | 浙江大学 | Method for separating 2-methylfuran and 2, 5-dimethylfuran |
| CN113075346A (en) * | 2021-04-01 | 2021-07-06 | 天津师范大学 | Gas chromatography separation analysis method based on aromatic macrocycle, molecular cage and pillar quinone and application |
| CN113181890A (en) * | 2021-04-28 | 2021-07-30 | 中国科学院兰州化学物理研究所 | Preparation and application of amino functionalized chiral column [5] arene chromatographic stationary phase |
| CN113578380A (en) * | 2021-08-05 | 2021-11-02 | 辽宁东科药业有限公司 | Column [5] arene ionic liquid catalyst based on propylimidazole functionalization and preparation method thereof |
| CN115672295A (en) * | 2022-11-05 | 2023-02-03 | 中国科学院兰州化学物理研究所 | Preparation and application of imine column [5] arene modified silica gel chromatographic packing |
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| CN113181890A (en) * | 2021-04-28 | 2021-07-30 | 中国科学院兰州化学物理研究所 | Preparation and application of amino functionalized chiral column [5] arene chromatographic stationary phase |
| CN113181890B (en) * | 2021-04-28 | 2022-09-16 | 中国科学院兰州化学物理研究所 | Preparation and application of amino functionalized chiral column [5] arene chromatographic stationary phase |
| CN113578380A (en) * | 2021-08-05 | 2021-11-02 | 辽宁东科药业有限公司 | Column [5] arene ionic liquid catalyst based on propylimidazole functionalization and preparation method thereof |
| CN115672295A (en) * | 2022-11-05 | 2023-02-03 | 中国科学院兰州化学物理研究所 | Preparation and application of imine column [5] arene modified silica gel chromatographic packing |
| CN115672295B (en) * | 2022-11-05 | 2023-12-15 | 中国科学院兰州化学物理研究所 | Preparation and application of imine type column [5] arene modified silica gel chromatographic packing |
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