CN111135808A - Silicon compound, stationary phase and application thereof - Google Patents
Silicon compound, stationary phase and application thereof Download PDFInfo
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- CN111135808A CN111135808A CN201911399076.5A CN201911399076A CN111135808A CN 111135808 A CN111135808 A CN 111135808A CN 201911399076 A CN201911399076 A CN 201911399076A CN 111135808 A CN111135808 A CN 111135808A
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- 230000005526 G1 to G0 transition Effects 0.000 title claims abstract description 77
- 150000003377 silicon compounds Chemical class 0.000 title claims abstract description 40
- 238000000926 separation method Methods 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 239000011159 matrix material Substances 0.000 claims abstract description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 22
- 239000000741 silica gel Substances 0.000 claims description 14
- 229910002027 silica gel Inorganic materials 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 229940088594 vitamin Drugs 0.000 claims description 12
- 229930003231 vitamin Natural products 0.000 claims description 12
- 235000013343 vitamin Nutrition 0.000 claims description 12
- 239000011782 vitamin Substances 0.000 claims description 12
- 238000001514 detection method Methods 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001589 carboacyl group Chemical group 0.000 claims description 9
- 150000002632 lipids Chemical class 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 235000005473 carotenes Nutrition 0.000 claims description 4
- 150000001746 carotenes Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 229910052710 silicon Inorganic materials 0.000 abstract description 6
- 239000010703 silicon Substances 0.000 abstract description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract description 4
- 125000003368 amide group Chemical group 0.000 abstract description 4
- 125000000565 sulfonamide group Chemical group 0.000 abstract description 4
- 238000013375 chromatographic separation Methods 0.000 abstract description 3
- 230000003438 effect on compound Effects 0.000 abstract description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 238000012360 testing method Methods 0.000 description 27
- 230000000052 comparative effect Effects 0.000 description 19
- 230000014759 maintenance of location Effects 0.000 description 15
- 239000000243 solution Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000002209 hydrophobic effect Effects 0.000 description 10
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- ABSPRNADVQNDOU-UHFFFAOYSA-N Menaquinone 1 Natural products C1=CC=C2C(=O)C(CC=C(C)C)=C(C)C(=O)C2=C1 ABSPRNADVQNDOU-UHFFFAOYSA-N 0.000 description 8
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 235000019175 phylloquinone Nutrition 0.000 description 8
- 239000011772 phylloquinone Substances 0.000 description 8
- MBWXNTAXLNYFJB-NKFFZRIASA-N phylloquinone Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)=C(C)C(=O)C2=C1 MBWXNTAXLNYFJB-NKFFZRIASA-N 0.000 description 8
- 229960001898 phytomenadione Drugs 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000011148 porous material Substances 0.000 description 7
- PFRQBZFETXBLTP-UHFFFAOYSA-N Vitamin K2 Natural products C1=CC=C2C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C(=O)C2=C1 PFRQBZFETXBLTP-UHFFFAOYSA-N 0.000 description 6
- DKHGMERMDICWDU-GHDNBGIDSA-N menaquinone-4 Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)=C(C)C(=O)C2=C1 DKHGMERMDICWDU-GHDNBGIDSA-N 0.000 description 6
- -1 methoxy, ethoxy, propoxy Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 235000019143 vitamin K2 Nutrition 0.000 description 6
- 239000011728 vitamin K2 Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000008157 edible vegetable oil Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- CNNRPFQICPFDPO-UHFFFAOYSA-N octacosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCO CNNRPFQICPFDPO-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 229940035893 uracil Drugs 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009830 intercalation Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CKIXFRABPZURLY-UHFFFAOYSA-N triethoxy(3-isocyanopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC[N+]#[C-] CKIXFRABPZURLY-UHFFFAOYSA-N 0.000 description 3
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 2
- 229960002666 1-octacosanol Drugs 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- 229930003448 Vitamin K Natural products 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 2
- 229960001826 dimethylphthalate Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- 125000005580 triphenylene group Chemical group 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 235000019168 vitamin K Nutrition 0.000 description 2
- 239000011712 vitamin K Substances 0.000 description 2
- 150000003721 vitamin K derivatives Chemical class 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- 229940046010 vitamin k Drugs 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 206010047634 Vitamin K deficiency Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- QAADEYIJKBTPIG-UHFFFAOYSA-N chloro-dimethyl-triacontylsilane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC[Si](C)(C)Cl QAADEYIJKBTPIG-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- QNLZIZAQLLYXTC-UHFFFAOYSA-N dimethylnaphthalene Natural products C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 208000031169 hemorrhagic disease Diseases 0.000 description 1
- 239000010460 hemp oil Substances 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical compound [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- RUFRLNPHRPYBLF-UHFFFAOYSA-N methoxy-dimethyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(C)OC RUFRLNPHRPYBLF-UHFFFAOYSA-N 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229940075566 naphthalene Drugs 0.000 description 1
- DZLRGXSUDHQIOZ-UHFFFAOYSA-N octacosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCN DZLRGXSUDHQIOZ-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 229940025790 vitamin k 1 injection Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/16—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to the conditioning of the fluid carrier
- B01D15/163—Pressure or speed conditioning
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/265—Adsorption chromatography
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/10—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/10—Refining fats or fatty oils by adsorption
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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Abstract
The invention relates to a silicon compound, a stationary phase and application thereof. The structural formula of the silicon compound is shown as the formula (I):
the present invention providesThe silicon compound contains polar groups (amide groups, sulfonamide groups, urea groups or carbamate groups), and is bonded in the matrix to prepare the stationary phase, so that silicon hydroxyl on the surface of the stationary phase can be effectively shielded, the peak shape of the alkaline compound is improved, and the silicon compound can be used in a mobile phase environment with higher water content during chromatographic separation; and the silicon compound is bonded with C20～C29The long-chain alkyl enables the prepared stationary phase to have higher stereoselectivity, and has good separation effect on compounds with long chains and high structural similarity.
Description
Technical Field
The invention relates to the technical field of liquid chromatography packing, in particular to a silicon compound, a stationary phase and application thereof.
Background
HPLC is an important analytical tool, and is suitable for analyzing various compounds with different charges, hydrophobicity, polarity, structures, sizes, and the like. Among these, the most commonly used stationary phase for HPLC is C18A stationary phase. However, in the specific application C18The stationary phase still has some defects, such as peak tailing caused by the interaction of the basic compound and underivatized silicon hydroxyl on the surface of the stationary phase. Based on this, researchers have reduced the residual surface silicon hydroxyl groups by capping with high purity silica. However, the use of the prepared stationary phase in water can cause 'hydrophobic collapse', so that the peak tailing of the alkaline compound still exists in many cases, thereby greatly reducing the retention of the analyte and influencing the reproducibility, and limiting C18The application of stationary phase.
For analytes with long chains and high similarity of molecular structures, such as lipids, fat-soluble vitamins and carotenes, the separation capacity of the C30 stationary phase is superior to that of the C18 stationary phase. However, the commercially available C30 silane is of low purity and typically consists of C20-C32 homologs. In addition, the bonding process is also challenging.
The polar embedded reverse phase separation medium is known in the chromatographic field, and the stationary phase improves the peak shape of a basic compound, improves the stereoselectivity and enables the stationary phase to be used in a mobile phase environment with higher water content. However, most of the existing polar intercalation stationary phases are C18Silanes, which are less effective in separation than long chain and structurally similar compounds. To our knowledge, polar intercalated inversions of alkyl moieties with more than 20 carbon atoms have not been synthesized and studied.
Disclosure of Invention
Therefore, it is necessary to provide a silicon compound, a stationary phase and applications thereof to solve the problem of poor separation effect of the conventional polar intercalation-type immobilization relative to a compound with a long chain and high structural similarity.
A silicon compound having a structural formula as shown in formula (I):
wherein R is1、R2、R3Each independently selected from substituted or unsubstituted C1-C4Alkyl, and R1、R2And R3At least one of them is alkoxy, halogen, alkylamino or alkanoyl;
Y1is selected from C2-C18An alkylene group; y is2Is selected from C20-C29An alkyl group;
l is selected from
The silicon compound provided by the invention contains polar groups (amide groups, sulfonamide groups, carbamido groups or carbamate groups) and is bonded into the matrix to prepare the stationary phase, so that silicon hydroxyl on the surface of the stationary phase can be effectively shielded during chromatographic separation, the peak shape of the alkaline compound is improved, and the silicon compound can be used in a mobile phase environment with higher water content; and the silicon compound is bonded with C20～C29The long-chain alkyl group ensures that the prepared stationary phase has higher stereoselectivity, and has especially prominent separation effect on compounds with long chains and high structural similarity, especially on substances of vitamins and lipids.
In one embodiment, R1、R2、R3Each independently selected from alkoxy;
Y1is selected from C2-C10An alkylene group; y is2Is selected from C25-C28An alkyl group; l is selected from
In one embodiment, the silicon compound is selected from:
the invention provides the use of any of the silicon compounds described herein for the preparation of a stationary phase.
The invention provides a stationary phase, and the preparation raw materials of the stationary phase comprise any one of the silicon compounds and a matrix.
In one embodiment, the stationary phase has a structure represented by formula (II):
wherein,
is a silica gel matrix, R4、R5Each independently selected from a hydroxyl group or an oxygen atom covalently attached to the silica gel matrix.
In one embodiment, the stationary phase is selected from:
the invention provides the use of any of the stationary phases described herein for the detection and/or separation of compounds having a linear length greater than 16 atoms.
In one embodiment, the compounds include lipids, vitamins, and carotenes.
The invention also provides the application of the stationary phase in detecting and/or separating isomers.
Drawings
FIG. 1 is a graph of the results of the hydrophobicity retention test for example 3 and comparative examples 3-4;
FIG. 2 is a graph showing the results of stereoselectivity tests of example 4 and comparative examples 5 to 6;
FIG. 3 is a separation spectrum of vitamin K1 and its isomers of example 5 and comparative example 7;
FIG. 4 is a separation spectrum of vitamin K2 and its isomers of example 6 and comparative example 8;
FIG. 5 is a spectrum of separation of lipids in the edible oil of example 7;
the abscissa of FIGS. 1-4 is time (time) in min, and the ordinate is Absorbance (Absorbance) in mAU; the abscissa of fig. 5 is time (time) in min and the ordinate is current (current) in pA.
Detailed Description
The present invention will be described in detail with reference to the accompanying drawings, which illustrate embodiments of the present invention. In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
The invention provides a silicon compound, the structural formula of which is shown as the formula (I):
wherein R is1、R2、R3Each independently selected from substituted or unsubstituted C1-C4Alkyl, and R1、R2And R3At least one of them is alkoxy, halogen, alkylamino or alkanoyl;
Y1is selected from C2-C18An alkylene group; y is2Is selected from C20-C29An alkyl group;
l is selected from
(amide group),
(sulfonamide group),
(ureido) or
(carbamate group).
Further, the alkoxy group may be selected from methoxy, ethoxy, propoxy, and the like; halogen may be selected from fluorine, chlorine, bromine, iodine, etc.; the alkylamino group can be selected from dimethylamino group, diethylamino group, etc.
In one embodiment, R1(or R)2Or R is3) Selected from alkoxy, halogen, alkylamino or alkanoyl, R2、R3(or R)1、R3Or R is1、R2) Each independently selected from alkoxy, halogen, alkylamino, alkanoyl, or substituted or unsubstituted C1-C4An alkyl group.
In one embodiment, R1、R2(or R)2、R3Or R is1、R3) Each independently selected from alkoxy, halogen, alkylamino or alkanoyl; r3(or R)1Or R is2) Selected from alkoxy, halogen, alkylamino, alkanoyl, or substituted or unsubstituted C1-C4An alkyl group.
In one embodiment, R1、R2、R3Respectively selected from alkoxy, halogen, alkylamino or alkanoyl.
Preferably, R1、R2、R3Each independently selected from alkoxy; y is1Is selected fromC2-C10An alkylene group; y is2Is selected from C25-C28An alkyl group; l is selected from
In one embodiment, the silicon compound is selected from:
the preparation of the silicon compounds (L is selected from urea groups or urethane groups) provided by the present invention can be achieved by: in an anhydrous solvent (e.g., toluene), an isocyanatosilane (e.g., (3-isocyanopropyl) triethoxysilane) is reacted with a long chain alkyl alcohol (e.g., 1-octacosanol) or a long chain alkyl amine. Alternatively, the same objective is achieved by reacting a primary aminosilane, a secondary aminosilane or a silyl alcohol with a long chain alkyl isocyanate.
The preparation method provided by the invention is also suitable for Y2Is selected from C30-C40Preparation of the silicon compound of the alkyl group. The long chain (C) is introduced into the reactor according to the above method20-C29Alkyl) compounds with long chains (C)30-C40Alkyl) compounds.
Further, the process for the preparation of the silicon compound (L is selected from urea groups or urethane groups) comprises the steps of:
the compound
Mixing the compound D-E with a solvent, and reacting at 60-80 ℃ for 20-24 h to obtain the compound D-E;
wherein R is6、R7、R8Each independently selected from substituted or unsubstituted C1-C4Alkyl, and R6、R7And R8At least one of them is alkoxy, halogen, alkylamino or alkanoyl; a is selected from C2-C18An alkylene group;
d is selected from hydroxyl or amine (primary or secondary); e is selected from C20-C29An alkyl group.
In some embodiments, the solvent may be toluene, xylene, or like organic solvent.
The preparation method of the silicon compound provided by the invention has the advantages of easily available raw materials and simple and convenient route.
The invention also provides the use of the silicon compounds described above for the preparation of the stationary phase.
The silicon compound provided by the invention contains polar groups (amide groups, sulfonamide groups, carbamido groups or carbamate groups) and is bonded into the matrix to prepare the stationary phase, so that silicon hydroxyl on the surface of the stationary phase can be effectively shielded during chromatographic separation, the peak shape of the alkaline compound is improved, and the silicon compound can be used in a mobile phase environment with higher water content; and the silicon compound is bonded with C20～C29The long-chain alkyl group ensures that the prepared stationary phase has higher stereoselectivity, and has especially prominent separation effect on compounds with long chains and high structural similarity, especially on substances of vitamins and lipids.
The invention provides a stationary phase, and the preparation raw materials of the stationary phase comprise any one of the compounds and a matrix.
In the present invention, the above silicon compound may be covalently bonded to the substrate. Further, the above silicon compound may be covalently attached to the substrate in the form of a single layer or with multiple layers.
In one embodiment, the substrate is a solid substrate with silicon hydroxyl groups (Si-OH). In the present invention, the solid substrate may also be a non-porous material.
In the present invention, the solid matrix may be in various shapes such as granular shape, block shape, lamellar shape, etc. which are conventionally used in the prior art.
In the present invention, the solid substrate may be spherical, square, or irregular in shape.
Preferably, the solid matrix is selected from silica/organic hybrid microspheres and/or silica microspheres.
In a real worldIn embodiments, the silica gel may be non-porous or of varying pore sizes. Preferably, the pore size is selected to be
Silica or silica/organic hybrid porous particles.
Specifically, the preparation steps of the stationary phase are as follows: the above silicon compound is reacted with silica gel in an inert solvent such as toluene at a high temperature. Depending on the application, water, acid or base catalysts may be employed to enhance surface coverage; and may be appropriately terminated as necessary.
In one embodiment, the stationary phase has a structural formula as shown in formula (II):
wherein,
is a silica gel matrix, R4、R5Each independently selected from a hydroxyl group or an oxygen atom covalently attached to a silica gel matrix.
Preferably, the stationary phase is selected from:
the invention also provides the use of the above stationary phase in the detection and/or separation of compounds having a linear length greater than 16 atoms.
In one embodiment, compounds with linear lengths greater than 16 atoms include lipids, vitamins, and carotenes.
Vitamin K, also called thrombovitamine, belongs to one of the vitamins, has phylloquinone bioactivity, which was first discovered and extracted in 1929 by danish chemists dalm from animal liver and hemp seed oil. Vitamin K comprises several forms of K1, K2, K3, K4, etc., wherein K1 and K2 are naturally occurring and belong to fat-soluble vitamins; and K3 and K4 are artificially synthesized and are water-soluble vitamins. Vitamin K1 belongs to vitamin medicine, and is essential for liver to synthesize factors II, VII, IX and X. The vitamin K1 injection is a 2009 edition national basic drug catalogue variety and is mainly used for treating hemorrhagic diseases caused by various vitamin K deficiencies. Due to the structural similarity, the separation of vitamins K1, K2 from their isomers is challenging and cannot be separated efficiently on C18.
Edible oils are lipids that are purified from plants and are usually liquids at room temperature. The main components are triglyceride, and small amount of free fatty acid and monoglyceride and diglyceride. Due to the diversity of alkyl chain lengths, unsaturation, sources, etc., the composition of edible oils is very complex.
And the vitamin K1, the vitamin K2 and the lipid compound generally have strong hydrophobicity, so that the separation of the vitamin and the lipid compound in the prior art has great challenges. The inventor of the present invention has continuously studied to provide a silicon compound and prepare a stationary phase, the hydrophobic retention characteristic of which facilitates the rapid separation of the above-mentioned substances, and the stationary phase has a high stereoselectivity and a good separation effect for the separation of the above-mentioned substances. Similarly, the stationary phase provided by the invention is also suitable for separating other compounds with long chains and high structural similarity.
The invention also provides the use of any of the above stationary phases for the detection and/or separation of isomers.
The following are specific examples
Example 1
Synthesis of stationary phase P1
12g of (3-isocyanopropyl) triethoxysilane was added to 100mL of a Toluene (Toluene) solution containing 24g of 1-octacosanol under nitrogen, followed by stirring at 80 ℃ for 24 hours, and then the reaction solution was subjected to solvent removal under reduced pressure to obtain a silicon compound M1.
10g of silica gel (particle size 5 μm, pore diameter: 10 g)
Surface area of 200m2And/g), 10g of silicon compound M1 and 50mL of toluene are mixed, ultrasonic treatment is carried out for 10min, then reflux reaction is carried out for 72h at 110 ℃, the mixed solution after reaction is filtered and washed by toluene, 1, 4-dioxane and acetone in sequence, and then vacuum drying is carried out for 3h at 50 ℃, thus obtaining the stationary Phase P1 which is marked as Phase 1. The silica gel surface bonding density was calculated to be 2.0. mu. mol/m based on the elemental analysis data (13.3% C, 0.55% N) of the bonding phase2。
Example 2
Synthesis of stationary phase P2
Under the protection of nitrogen, 1mol of (3-isocyanopropyl) triethoxysilane is added into 100mL of a toluene solution containing 1.1mol of 1-octacosylamine, then the reaction is stirred at 80 ℃ for 24 hours, and then the reaction solution is decompressed and the solvent is removed to obtain a silicon compound M2.
10g of silica gel (particle size 5 μm, pore diameter: 10 g)
Surface area of 200m2And/g), 10g of silicon compound M2 and 50mL of toluene are mixed, ultrasonic treatment is carried out for 10min, reflux reaction is carried out for 72h at 110 ℃, the mixed solution after reaction is filtered and washed by toluene, 1, 4-dioxane and acetone in sequence, and then vacuum drying is carried out for 3h at 50 ℃ to obtain the stationary phase P2. The silica gel surface bonding density was calculated to be 2.1. mu. mol/m based on the elemental analysis data (13.0% C, 1.2% N) of the bonding phase2。
Comparative example 1
Under nitrogen protection, 25g of n-triacontyldimethylchlorosilane and 10g of imidazole were added to 300mL of a solution containing 25g of silica gel (particle size 5 μm, pore diameter: 25 g)
Surface area of 200m2In a toluene dispersion of/g), stirring at 100 ℃ for 24h, thenThe reaction mixture was filtered, washed with toluene, 1, 4-dioxane, water and acetone in that order, and then dried under vacuum at 50 ℃ for 8h to give a C30 stationary phase.
Under the protection of nitrogen, 25g of trimethylchlorosilane and 10g of imidazole are added into 300mL of toluene dispersion liquid containing the intermediate, the mixture is stirred for 24 hours at 100 ℃, the reaction mixture is filtered, washed by toluene, 1, 4-dioxane, water and acetone in sequence, and then dried for 8 hours in vacuum at 50 ℃ to obtain stationary phase P3, wherein the stationary phase P3 has the structure
Denoted as C30. The surface bonding density calculated from the elemental analysis data (13.01% C) of the bonding phase was 2.0. mu. mol/m2。
Comparative example 2
25g of octadecyldimethylmethoxysilane and 1g of imidazole were added to 300mL of a solution containing 50g of silica gel (particle size 5 μm, pore diameter: 50 g) under nitrogen protection
Surface area of 200m2Stirring the mixture for 24 hours at 100 ℃ in toluene dispersion, filtering the reaction mixture, washing the reaction mixture with toluene, 1, 4-dioxane, water and acetone in sequence, and then drying the reaction mixture for 8 hours in vacuum at 50 ℃ to obtain stationary phase P4, wherein the structural formula of the stationary phase is shown in the specification
Denoted Polar C18. The surface bonding density calculated from the elemental analysis data (12.24% C, 0.63% N) of the bonding phase was 2.9. mu. mol/m2。
Performance evaluation
The following tests of examples 3-7 used the stationary Phase prepared in example 1 (Phase 1); testing of the following comparative examples the stationary phases prepared in comparative examples 1, 2 (C30, Polar C18) were used; filling the stationary phase into a stainless steel column with the diameter of 4.6 multiplied by 150mm by adopting the traditional high-pressure slurry technology for testing;
the test samples in the following examples and comparative examples were formulated using the mobile phase used in the test method, except that the test sample of example 7 was formulated using isopropyl alcohol.
Hydrophobic retention test: the retention of the neutral hydrophobic compound by the stationary phase was evaluated, and the retention time of naphthalene, which is a neutral hydrophobic compound, was taken as an index of the hydrophobic retention capacity, and a longer retention time indicates a stronger hydrophobic retention capacity.
Example 3
Test samples: a mixture of uracil (10. mu.g/mL), dimethyl phthalate (0.1. mu.L/mL), and naphthalene (300. mu.g/mL);
and (3) testing conditions are as follows: mobile phase: CH (CH)3CN/H2O (60:40 v/v); flow rate: 1 mL/min; sample introduction amount: 5 mu L of the solution; temperature: 30 ℃; detection wavelength: 254 nm;
comparative example 3
Essentially the same as in example 3, except that the stationary phase is C30。
Comparative example 4
Essentially the same as example 3, except that the stationary phase was Polar C18.
The results of the hydrophobicity retention test of example 3 and comparative examples 3 to 4 are shown in FIG. 1, and 1, 2, and 3 in FIG. 1 represent the peaks of uracil, dimethyl phthalate, and naphthalene, respectively.
As shown in FIG. 1, the naphthalene retention factor for the Phase1 test is 2.4, while the naphthalene retention factors for the C30 and PolarC18 tests are 3.0 and 3.2, respectively, under the same test conditions. It can be seen that under the conditions of comparable bonding density, due to the introduction of polar intercalating groups, Phase1 has a weaker hydrophobic retention than C30 which does not contain polar intercalating groups; due to steric hindrance, Phase1 has a lower bonding density than C18 containing the same polar insertion group, resulting in a decrease in hydrophobic retention.
Since vitamin K1, vitamin K2 and lipid compounds have strong hydrophobicity, the hydrophobic retention properties of Phase1 contribute to the rapid separation of such compounds.
Stereoselectivity test stereoselectivity was expressed as α3/2＝(t3-t0)/(t2-t0)。
Example 4
Test samples: a mixture of uracil (40. mu.g/mL), ortho-terphenyl (140. mu.g/mL) and triphenylene (40. mu.g/mL).
And (3) testing conditions are as follows: mobile phase: MeOH/H2O (90:10 v/v); flow rate: 1 mL/min; sample introduction amount: 5 mu L of the solution; column temperature: 30 ℃; detection wavelength: 254 nm.
Comparative example 5
Essentially the same as example 4, except that the stationary phase is C30。
Comparative example 6
Essentially the same as example 4, except that the stationary phase was Polar C18.
The results of the stereoselectivity tests of example 4 and comparative examples 5 to 6 are shown in FIG. 2, in which 1, 2 and 3 represent the peaks of uracil, ortho-terphenyl and triphenylene, respectively.
α of stationary Phase1 by spectrogram analysis3/2α of fixed phase C30 ═ 3.943/2α of stationary phase Polar C18 ═ 1.733/2＝2.36。
Although the surface bonding density of the stationary Phase1 is equivalent to that of the stationary Phase C30, the stereoselectivity of the stationary Phase1 is better than that of the stationary Phase C30 due to the introduction of polar insertion groups and the length (35 atoms) of the bonded Phase.
In general, stereoselectivity increases with increasing surface bonding density. Although the surface bonding density of the stationary Phase1 is much lower than that of the stationary Phase Polar C18, the stereoselectivity is significantly higher due to the length of the hydrophobic group (28 atoms) of its bonded Phase. Therefore, the stationary phase provided by the invention is more beneficial to separating the substances to be separated with higher structural similarity.
Separation of vitamin K1 and its isomers
Example 5
Test samples: vitamin K1;
and (3) testing conditions are as follows: mobile phase: MeOH/H2O (95:5 v/v); flow rate: 1 mL/min; sample introduction amount: 10 mu L of the solution; column temperature: 25 ℃; detection wavelength: 254 nm.
Comparative example 7
Substantially the same as in example 5, except that,the stationary phase is C30。
The separation spectrum of vitamin K1 and its isomers of example 5 and comparative example 7 is shown in fig. 3, and the data of the spectrum analysis is shown in table 1.
TABLE 1
As can be seen from fig. 3 and table 1, the stationary phase C30 has a long detection time and a poor separation effect, and the separation degree is only 1.46; under the same test conditions, the separation degree of the stationary Phase1 is obviously improved (3.62), and the separation speed is doubled.
Separation of vitamin K2 and its isomers
Example 6
Test samples: vitamin K2;
and (3) testing conditions are as follows: mobile phase, MeOH/H2O (95:5 v/v); flow rate: 1 mL/min; sample introduction amount: 10 mu L of the solution; column temperature: 25 ℃; detection wavelength: 254 nm.
Comparative example 8
Essentially the same as example 6, except that the stationary phase was C30。
The separation spectrum of vitamin K2 and its isomers of example 6 and comparative example 8 is shown in fig. 4, and the data of the spectrum analysis is shown in table 2.
TABLE 2
As can be seen from table 2, the stationary Phase C30 achieved baseline separation (degree of separation of 2.41), while the stationary Phase1 achieved better degree of separation in a shorter time under the same test conditions (3.15).
Separation of lipids from edible oils
Example 7
Test samples: a mixture of olive oil (5mg/mL), sesame oil (5mg/mL), peanut oil (5mg/mL) and soybean oil (5 mg/mL).
And (3) testing conditions are as follows: mobile phase: a: CH (CH)3CN, B: 100mM ammonium acetate (NH)4OAc) buffer, ph5.0, C: and (3) isopropanol.
Gradient elution procedure: balancing with mobile phase 85% A, 5% B and 10% C for 10min, injecting test sample for 0-10min, 85-65% A, 5% B and 10-30% C, 10-60min, 65-20% A, 5% B and 30-75% C, 60-70 min, 20-5% A, 5% B and 75-90% C, and maintaining at 5% A, 5% B and 90% C for 10 min;
flow rate: 1 mL/min; sample introduction amount: 5 mu L of the solution; temperature: 30 ℃; the detection method comprises the following steps: the light is scattered by evaporation.
As can be seen from the analysis spectrum of fig. 5, the stationary Phase1 has high stereoselectivity and good separation degree for the components with similar structures in the edible oil.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (10)
1. A silicon compound having a structural formula according to formula (I):
wherein R is1、R2、R3Each independently selected from substituted or unsubstituted C1-C4Alkyl, and R1、R2And R3At least one of them is alkoxy, halogen, alkylamino or alkanoyl;
Y1is selected from C2-C18An alkylene group; y is2Is selected from C20-C29An alkyl group;
l is selected from
2. The silicon compound according to claim 1, wherein R is1、R2、R3Each independently selected from alkoxy;
Y1is selected from C2-C10An alkylene group; y is2Is selected from C25-C28An alkyl group; l is selected from
3. The silicon compound according to claim 1, wherein the silicon compound is selected from the group consisting of:
4. use of a silicon compound according to any one of claims 1 to 3 for the preparation of a stationary phase.
5. A stationary phase prepared from the silicon compound according to any one of claims 1 to 3 and a matrix.
6. The stationary phase according to claim 5, wherein the structural formula of the stationary phase is as shown in formula (II):
wherein,
is a silica gel matrix, R4、R5Each independently selected from a hydroxyl group or an oxygen atom covalently attached to the silica gel matrix.
7. The stationary phase according to claim 6, wherein the stationary phase is selected from the group consisting of:
8. use of a stationary phase according to any one of claims 5 to 7 for the detection and/or separation of compounds having a linear length greater than 16 atoms.
9. Use according to claim 8, wherein the compounds comprise lipids, vitamins and carotenes.
10. Use of a stationary phase according to any of claims 5 to 7 for the detection and/or separation of isomers.
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