CN1283792A - Alkyl ether type high performance liquid chromatography reverse phase packing and preparation method thereof - Google Patents
Alkyl ether type high performance liquid chromatography reverse phase packing and preparation method thereof Download PDFInfo
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- CN1283792A CN1283792A CN99111256A CN99111256A CN1283792A CN 1283792 A CN1283792 A CN 1283792A CN 99111256 A CN99111256 A CN 99111256A CN 99111256 A CN99111256 A CN 99111256A CN 1283792 A CN1283792 A CN 1283792A
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- 238000004128 high performance liquid chromatography Methods 0.000 title claims abstract description 10
- 238000012856 packing Methods 0.000 title claims abstract description 9
- 150000005215 alkyl ethers Chemical class 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000000741 silica gel Substances 0.000 claims abstract description 26
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 16
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004593 Epoxy Substances 0.000 claims abstract description 7
- 229910015900 BF3 Inorganic materials 0.000 claims abstract description 6
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 4
- 125000005233 alkylalcohol group Chemical group 0.000 claims abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 58
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 12
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 11
- 239000005051 trimethylchlorosilane Substances 0.000 claims description 6
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 239000000945 filler Substances 0.000 abstract description 22
- 238000005259 measurement Methods 0.000 abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000460 chlorine Substances 0.000 abstract description 2
- 229910052801 chlorine Inorganic materials 0.000 abstract description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 abstract 3
- 125000001033 ether group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 14
- 239000012071 phase Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 10
- 238000001291 vacuum drying Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000005046 Chlorosilane Substances 0.000 description 7
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 3
- 206010013786 Dry skin Diseases 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000002270 exclusion chromatography Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- -1 silane compound Chemical class 0.000 description 1
- 238000002444 silanisation Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Abstract
The invention relates to an ether type high performance liquid chromatography reversed-phase filler prepared by two methods by utilizing gamma-epoxypropyloxypropyltrimethoxysilane. One is that silica gel reacts with gamma-epoxypropyloxypropyl trimethoxy silane to prepare epoxy silica gel, which reacts with alkyl alcohol under the catalysis of boron trifluoride ether to obtain ether-type high performance liquid chromatography reverse filler, and the other is that gamma-epoxypropyloxypropyl trimethoxy silane reacts with alkyl alcohol to prepare trimethoxy silane with long chain ether group, which then reacts with silica gel to obtain the ether-type high performance liquid chromatography reverse filler. The column efficiency of the filler obtained by the two methods is above 45000 theoretical plates by column packing measurement. The filler does not contain chlorine, and cannot decompose and release hydrogen chloride to cause the performance reduction and the performance instability of the filler, and the synthetic route is simple and reliable and has low cost.
Description
The invention belongs to the preparation method of the new and effective liquid chromatography stuffing that a kind of high performance liquid chromatography uses, be specifically related to a kind of preparation method of novel ether type efficient liquid-phase chromatographic reverse filler.
Chromatographic column is the heart of high performance liquid chromatograph, and filler then is the core of chromatographic column.Reverse phase filler has obtained in fields such as biology, chemistry, pharmaceutical industries using widely, according to document [J.G.Dorsey and W.T.Cooper, B.A.Siles, J.P.Foley, H.G.Borth, Anal.Chem., 70 (1998) 591R], reverse-phase chromatography remains most important pattern in the chromatographic process.Nowadays, worldwide have to surpass 600 kinds of commercial reversed-phase columns, they are having different alkyl chain length (as butyl, octyl group, cetyl or octadecyl), and different selectivity is its feature.A large amount of new or better reversed-phase columns also constantly put goods on the market [3].Separate for obtaining better RP-HPLC, usually using dissimilar chromatographic columns cooperates the moving phase variation just can be optimized [K.Kimata to the chromatographic condition of target system to be separated, K.Iwaguchi, S.Onishi, K.Jinno, R.Ekstee, K.Hosoya, J.Chromatogr.Sci., 1989,721-728].
At present, preparation is that the method for the reverse phase filler of matrix mainly contains two classes with silica gel, and a kind of is to utilize the Silanization reaction of silica gel to carry out, and another kind is the direct condensation with silane compound, obtains with sol gel reaction.In the first kind, be mostly with dichloro, trichlorine or a chlorosilane to be that reagent synthesizes.Chlorosilane is more expensive reagent, and chlorosilane is easy in malaria and the aqueous vapor reaction, so the safeguard measure of being done in synthesizing can increase its cost undoubtedly; On the other hand, the reappearance of bonding is difficult to control, as deals with the non-specific adsorption of unavoidable generation to some material improperly.Except that chlorosilane, in actual applications, it is to be connected to the silica gel surface by a middle silylating reagent that contains active function group (as amino, epoxy radicals etc.) that many stationary phase are arranged.γ-glycidoxypropyl trimethoxysilane (KH560) is one of widely used important coupled reagent of middle silane.[K.Kimata, K.Iwaguchi, S.Onishi such as Chang, K.Jinno, R.Ekstee, K.Hosoya, J.Chromatogr.Sci., 1989,721-728] once narrated the use of epoxy radicals in bonding prepares mutually, up to now, prepared dissimilar efficient liquid phase chromatographic stuffings with it, as hydrophobic interaction chromatograph filler [V.Smigol, F.Sveec, J.J.M.Frecheet, Anal.Chem., 66 (1994) 2129], exclusion chromatography filler [J.P.Chang, J.G.An, Chromatographia, 25 (4) (1988) 350], high performance liquid chromatogram affinity chromatograph filling [R.Ovalle, Anal.Chem., 229 (1995) 1], ion-exchange packing [K.Kimata, K.Iwaguchi, S.Onishi, K.Jinno, R.Ekstee, K.Hosoya, J.Chromatogr.Sci., 1989,721-728] etc.But do not see the report that has in order to preparation chain alkyl chain reverse-phase chromatography filler.
The present invention just provides a kind of alkylether type reverse filler for efficient liquid-phase chromatography and its preparation method.
Alkylether type reverse filler for efficient liquid-phase chromatography of the present invention has structure as follows:
The present invention adopts non-chlorosilane type new technique for synthesizing, and promptly a kind of new synthetic route based on the γ-glycidoxypropyl trimethoxysilane that has epoxy radicals is in order to synthesis of alkyl ether type efficient liquid-phase chromatographic reverse filler.The synthetic of filler can be adopted single stage method, also can adopt the technology of two-step approach.The preparation of filler follows these steps to carry out:
1, single stage method: (1) makes a silica gel and 0.3～0.6 part of KH560 reaction, generates epoxy radicals silica gel, makes it at 0.1～20% part of boron trifluoride diethyl etherate (BF again
3.Et
2O) catalysis was reacted 2～48 hours down in 60～180 ℃ with (0.5～5.0) part alkylol down, and reaction product is cleaned, vacuum drying; (2) get a above-mentioned desciccate and mix, in 60～150 ℃ of reactions 2～48 hours with the dry organic solvent that contains 0.1-1 part end socket reagent.Used end socket reagent can be any methyl-monosilane, but the most handy trimethyl type, as trimethyl chlorosilane, HMDS etc.Used organic solvent can be not with any organic solvent of chlorosilane and silicon hydroxyl generation chemical reaction, as toluene, dioxane etc.Reaction product is cleaned with organic solvent, get final product after the vacuum drying the efficient reverse phase filler of product alkyl ether type.
2 two step methods: the alkylol of (1) shilling a KH560 and 1 to 5 part is in 60～180 ℃, under (0.1%～20%) part boron trifluoride diethyl etherate catalysis, react to each other, this reaction can be used or not with an organic solvent, except that can with epoxy radicals responsiveness person do not have special restriction.After the reaction, the purpose product should be with the suitable purifying of conventional method.(2) get the product of a purifying, make itself and 0.1～2 part of silica gel, do not have special restriction in organic solvent commonly used, in 60～180 ℃ of reactions 2～48 hours, product was cleaned with organic solvent, vacuum drying.Product carries out end socket with single stage method to be handled.
The preparation of this filler is not used danger, valency height and is easily caused the chlorosilane of residual chlorine, not only synthetic route is simple and reliable, with low cost, and, can not decompose the instability that discharges hydrogen chloride and cause carrier performance decline and performance, and its excellent performance because of not chloride, except that character with common reverse-phase chromatography filler, to make it have bigger polarity and an alkyl chain flexible preferably because of ehter bond, thereby more help the separation of some physiological activators, has the fabulous market competitiveness.
The embodiment I: (1) takes by weighing 5g 18 alcohol and is dissolved in the 50mL dry toluene, adds the 0.5mL boron trifluoride ether solution then, mixes mutually with 5g γ-glycidoxypropyl trimethoxysilane and stirs it with oar shape stirrer, in 90 ℃ of reactions 12 hours down.Reaction finishes, and removes polar material (as boron trifluoride diethyl etherate and glycol-based that produces and unreacted 18 alcohol etc.) with conventional method.(2) take by weighing the spherical porous silica gel (Sinopak-s-110 of 5g, particle diameter 5 μ, aperture 11nm) under vacuum (0.1～-0.95MPa) mix mutually and make silica gel be suspended in the reactant liquor with oar shape stirrer with (1) products therefrom, reacted 8 hours down in 110 ℃, reaction finishes, and product is filtered, fully clean with toluene again, after the air dry, with boulton process ,-0.1～-0.95MPa/60 ℃ following vacuum drying.(3) get (2) product, place three-necked bottle, under vacuum, be heated to 150 ℃, reacted 4 hours, treat that temperature is fallen after, drive down in vacuum, add and contain the toluene solution of 0.5g trimethyl chlorosilane and make bonded silica gel be suspended in the reactant liquor with oar shape stirrer, reacted 8 hours down in 110 ℃, reaction finishes, and product is filtered, fully clean with toluene again, after the air dry, with boulton process ,-0.1～-0.95MPa/60 ℃ following vacuum drying.(4) get (3) product 4.2g, with phenixin: dioxane (2:1) solution is homogenate, loads φ 5 * 250 stainless steel chromatogram posts with the homogenate method respectively, stowing pressure 40Mpa, with the phenanthrene is sample, and 70% methanol aqueous solution is a moving phase, and it is 51000 theoretical cam curves that measurement column is imitated.
The embodiment II: (1) get the spherical porous silica gel of 5g (Sinopak-s-110, particle diameter 5 μ, aperture 11nm) in-0.1～-the 0.95MPa vacuum under, in 150 ℃ of heating 4 hours down; Under vacuum drives, add among the dry toluene 50mL that contains 1.5g γ-glycidoxypropyl trimethoxysilane behind the natural cooling and reacted 8 hours down in 109 ℃.(2) add 0.5mL boron trifluoride diethyl etherate and 5g 18 alcohol again after the cooling, stirring makes molten, and makes them react 28 hours down in 60 ℃.(3) filter with the toluene wash clean ,-0.1～-the 0.95MPa vacuum under,, carry out end socket and handle (with example 1) after 2 hours in 60 ℃ of dryings.(4) get (3) product 4.2 g, with phenixin: dioxane (2:1) solution is homogenate, loads φ 5 * 250 stainless steel chromatogram posts with the homogenate method, stowing pressure 40Mpa, with the phenanthrene is sample, and 70% methanol aqueous solution is a moving phase, and it is 45000 theoretical cam curves that measurement column is imitated.
The embodiment III: (1) takes by weighing 25g 18 alcohol and is dissolved in the 100mL dry toluene, adds the 1mL boron trifluoride ether solution then, mixes mutually with 5g γ-glycidoxypropyl trimethoxysilane and stirs it with oar shape stirrer, in 180 ℃ of reactions 2 hours down.Reaction finishes, and removes polar material (as boron trifluoride diethyl etherate and glycol-based that produces and unreacted 18 alcohol etc.) with conventional method.(2) take by weighing the spherical porous silica gel of 10g (Sinopak-s-110, particle diameter 5 μ, aperture 11nm).Under vacuum (0.1～-0.95MPa) mix mutually and make silica gel be suspended in the reactant liquor with oar shape stirrer with (1) products therefrom, reacted 2 hours down in 180 ℃, reaction finishes, product is filtered, fully clean with toluene again, after the air dry, with boulton process ,-0.1～-0.95MPa/60 ℃ following vacuum drying.(3) get (2) product, place three-necked bottle, under vacuum, be heated to 150 ℃, reacted 4 hours, treat that temperature is fallen after, drive down in vacuum, add and contain the toluene solution of 5g trimethyl chlorosilane and make bonded silica gel be suspended in the reactant liquor with oar shape stirrer, reacted 2 hours down in 150 ℃, reaction finishes, and product is filtered, fully clean with toluene again, after the air dry, with boulton process ,-0.1～-0.95MPa/60 ℃ following vacuum drying.(4) get (3) product 4.2g, with phenixin: dioxane (2:1) solution is homogenate, loads φ 5 * 250 stainless steel chromatogram posts with the homogenate method respectively, stowing pressure 40Mpa, with the phenanthrene is sample, and 70% methanol aqueous solution is a moving phase, and it is 55000 theoretical cam curves that measurement column is imitated.
The embodiment IV: (1) get the spherical porous silica gel of 5g (Sinopak-s-110, particle diameter 5 μ, aperture 11nm) in-0.1～-the 0.95MPa vacuum under, in 150 ℃ of heating 4 hours down; Under vacuum drives, add among the dry toluene 50mL that contains 3g γ-glycidoxypropyl trimethoxysilane behind the natural cooling and reacted 8 hours down in 109 ℃.(2) add 5mL boron trifluoride diethyl etherate and 25g 18 alcohol again after the cooling, stirring makes molten, and makes them react 2 hours down in 180 ℃.(3) filter with the toluene wash clean ,-0.1～-the 0.95MPa vacuum under,, carry out end socket and handle (with example 1) after 2 hours in 60 ℃ of dryings.(4) get (3) product 4.2g, with phenixin: dioxane (2: 1) solution is homogenate, loads φ 5 * 250 stainless steel chromatogram posts with the homogenate method, stowing pressure 40Mpa, with the phenanthrene is sample, and 70% methanol aqueous solution is a moving phase, and it is 47000 theoretical cam curves that measurement column is imitated.
The embodiment V: (1) takes by weighing 25g 18 alcohol and is dissolved in the 100mL dry toluene, adds the 1mL boron trifluoride ether solution then, mixes mutually with 5g γ-glycidoxypropyl trimethoxysilane and stirs it with oar shape stirrer, in 60 ℃ of reactions 48 hours down.Reaction finishes, and removes polar material (as boron trifluoride diethyl etherate and glycol-based that produces and unreacted 18 alcohol etc.) with conventional method.(2) take by weighing the spherical porous silica gel of 10g (Sinopak-s-110, particle diameter 5 μ, aperture 11nm).Under vacuum (0.1～-0.95MPa) mix mutually and make silica gel be suspended in the reactant liquor with oar shape stirrer with (1) products therefrom, reacted 48 hours down in 60 ℃, reaction finishes, product is filtered, fully clean with toluene again, after the air dry, with boulton process ,-0.1～-0.95MPa/60 ℃ following vacuum drying.(3) get (2) product, place three-necked bottle, under vacuum, be heated to 150 ℃, reacted 4 hours, treat that temperature is fallen after, drive down in vacuum, add and contain the toluene solution of 5g trimethyl chlorosilane and make bonded silica gel be suspended in the reactant liquor with oar shape stirrer, reacted 48 hours down in 60 ℃, reaction finishes, and product is filtered, fully clean with toluene again, after the air dry, with boulton process ,-0.1～-0.95MPa/60 ℃ following vacuum drying.(4) get (3) product 4.2g, with phenixin: dioxane (2: 1) solution is homogenate, loads φ 5 * 250 stainless steel chromatogram posts with the homogenate method respectively, stowing pressure 40Mpa, with the phenanthrene is sample, and 70% methanol aqueous solution is a moving phase, and it is 58000 theoretical cam curves that measurement column is imitated.
Claims (3)
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| CN99111256A CN1108525C (en) | 1999-08-04 | 1999-08-04 | Alkyl ether type high performance liquid chromatography reversed phase filler and preparation method thereof |
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| CN99111256A CN1108525C (en) | 1999-08-04 | 1999-08-04 | Alkyl ether type high performance liquid chromatography reversed phase filler and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103990298A (en) * | 2014-05-09 | 2014-08-20 | 河北大学 | Preparation method of macroporous organic-inorganic hybrid monolithic column with outer surface hydrophilicity |
| CN115364829A (en) * | 2022-08-19 | 2022-11-22 | 中谱科技(福州)有限公司 | A kind of acid-resistant silica gel chromatographic column filler and its preparation method and application |
-
1999
- 1999-08-04 CN CN99111256A patent/CN1108525C/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103990298A (en) * | 2014-05-09 | 2014-08-20 | 河北大学 | Preparation method of macroporous organic-inorganic hybrid monolithic column with outer surface hydrophilicity |
| CN103990298B (en) * | 2014-05-09 | 2015-10-28 | 河北大学 | A kind of preparation method of surface and hydrophilic outer macropore organic-inorganic hybridization monolithic column |
| CN115364829A (en) * | 2022-08-19 | 2022-11-22 | 中谱科技(福州)有限公司 | A kind of acid-resistant silica gel chromatographic column filler and its preparation method and application |
| CN115364829B (en) * | 2022-08-19 | 2024-05-28 | 中谱科技(福州)有限公司 | Acid-resistant silica gel chromatographic column packing and preparation method and application thereof |
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| CN1108525C (en) | 2003-05-14 |
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