KR20170010479A - Preparing method of filler endcapped highly with a good acid resisting and filler and packing column using same - Google Patents
Preparing method of filler endcapped highly with a good acid resisting and filler and packing column using same Download PDFInfo
- Publication number
- KR20170010479A KR20170010479A KR1020150102170A KR20150102170A KR20170010479A KR 20170010479 A KR20170010479 A KR 20170010479A KR 1020150102170 A KR1020150102170 A KR 1020150102170A KR 20150102170 A KR20150102170 A KR 20150102170A KR 20170010479 A KR20170010479 A KR 20170010479A
- Authority
- KR
- South Korea
- Prior art keywords
- organic
- filler
- group
- silica gel
- silanol
- Prior art date
Links
- 239000000945 filler Substances 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 26
- 239000002253 acid Substances 0.000 title description 6
- 238000012856 packing Methods 0.000 title description 3
- 125000005372 silanol group Chemical group 0.000 claims abstract description 37
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000741 silica gel Substances 0.000 claims abstract description 24
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 24
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 19
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 14
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 14
- 239000005046 Chlorosilane Substances 0.000 claims abstract description 13
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000010168 coupling process Methods 0.000 claims abstract description 12
- 230000008878 coupling Effects 0.000 claims abstract description 10
- 238000005859 coupling reaction Methods 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 29
- -1 chlorosiloxane Chemical class 0.000 claims description 16
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 13
- 229910000077 silane Inorganic materials 0.000 claims description 13
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 11
- 125000000524 functional group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 239000010703 silicon Substances 0.000 claims description 8
- 238000004132 cross linking Methods 0.000 claims description 7
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 abstract description 6
- 230000002378 acidificating effect Effects 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical group C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 2
- HMFFOEBLYHLRQN-UHFFFAOYSA-N 4-trichlorosilylbutanenitrile Chemical compound Cl[Si](Cl)(Cl)CCCC#N HMFFOEBLYHLRQN-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DMEXFOUCEOWRGD-UHFFFAOYSA-N chloro-[chloro(dimethyl)silyl]oxy-dimethylsilane Chemical compound C[Si](C)(Cl)O[Si](C)(C)Cl DMEXFOUCEOWRGD-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- BYLOHCRAPOSXLY-UHFFFAOYSA-N dichloro(diethyl)silane Chemical compound CC[Si](Cl)(Cl)CC BYLOHCRAPOSXLY-UHFFFAOYSA-N 0.000 description 2
- UWGIJJRGSGDBFJ-UHFFFAOYSA-N dichloromethylsilane Chemical compound [SiH3]C(Cl)Cl UWGIJJRGSGDBFJ-UHFFFAOYSA-N 0.000 description 2
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 description 2
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 2
- XYYQWMDBQFSCPB-UHFFFAOYSA-N dimethoxymethylsilane Chemical compound COC([SiH3])OC XYYQWMDBQFSCPB-UHFFFAOYSA-N 0.000 description 2
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- SLYCYWCVSGPDFR-UHFFFAOYSA-N octadecyltrimethoxysilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SLYCYWCVSGPDFR-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical group Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 2
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 2
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 2
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- 239000005052 trichlorosilane Substances 0.000 description 2
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- CCPYCNSBZPTUMJ-UHFFFAOYSA-N 1,3,5,7,9,2,4,6,8,10-pentaoxapentasilecane Chemical class O1[SiH2]O[SiH2]O[SiH2]O[SiH2]O[SiH2]1 CCPYCNSBZPTUMJ-UHFFFAOYSA-N 0.000 description 1
- QZKKBTHDXXCSKJ-UHFFFAOYSA-N 2,2-diethoxyethylsilane Chemical compound CCOC(C[SiH3])OCC QZKKBTHDXXCSKJ-UHFFFAOYSA-N 0.000 description 1
- GPIARXZSVWTOMD-UHFFFAOYSA-N 4-[chloro(dimethyl)silyl]butanenitrile Chemical compound C[Si](C)(Cl)CCCC#N GPIARXZSVWTOMD-UHFFFAOYSA-N 0.000 description 1
- BFGOGLKYJXQPJZ-UHFFFAOYSA-N 4-methylhept-1-ene Chemical compound CCCC(C)CC=C BFGOGLKYJXQPJZ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UYQKTMMDHKHNSU-UHFFFAOYSA-N COC(C[SiH3])OC Chemical compound COC(C[SiH3])OC UYQKTMMDHKHNSU-UHFFFAOYSA-N 0.000 description 1
- GDPVIUNJBFIRCD-UHFFFAOYSA-N C[SiH](Cl)CCCC#N Chemical compound C[SiH](Cl)CCCC#N GDPVIUNJBFIRCD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- AQBOUNVXZQRXNP-UHFFFAOYSA-L azane;dichloropalladium Chemical compound N.N.N.N.Cl[Pd]Cl AQBOUNVXZQRXNP-UHFFFAOYSA-L 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- CSWKBQVZBQTHBO-UHFFFAOYSA-N bis[[chloro(dimethyl)silyl]-dimethylsilyl]-dimethylsilane Chemical compound C[Si](C)(Cl)[Si](C)(C)[Si](C)(C)[Si](C)(C)[Si](C)(C)Cl CSWKBQVZBQTHBO-UHFFFAOYSA-N 0.000 description 1
- GJIYNWRLGOMDEX-UHFFFAOYSA-N bis[[chloro(dimethyl)silyl]oxy]-dimethylsilane Chemical compound C[Si](C)(Cl)O[Si](C)(C)O[Si](C)(C)Cl GJIYNWRLGOMDEX-UHFFFAOYSA-N 0.000 description 1
- VXZHPKCBWCBOAU-UHFFFAOYSA-N bis[chloro(dimethyl)silyl]-dimethylsilane Chemical compound C[Si](C)(Cl)[Si](C)(C)[Si](C)(C)Cl VXZHPKCBWCBOAU-UHFFFAOYSA-N 0.000 description 1
- FQEKAFQSVPLXON-UHFFFAOYSA-N butyl(trichloro)silane Chemical compound CCCC[Si](Cl)(Cl)Cl FQEKAFQSVPLXON-UHFFFAOYSA-N 0.000 description 1
- YHEJRJLLZCSZBG-UHFFFAOYSA-N butyl-dimethoxy-pentoxysilane Chemical compound CCCCCO[Si](CCCC)(OC)OC YHEJRJLLZCSZBG-UHFFFAOYSA-N 0.000 description 1
- WYPYJRBVFDQINZ-UHFFFAOYSA-N chloro-[[[chloro(dimethyl)silyl]-dimethylsilyl]-dimethylsilyl]-dimethylsilane Chemical compound C[Si](C)(Cl)[Si](C)(C)[Si](C)(C)[Si](C)(C)Cl WYPYJRBVFDQINZ-UHFFFAOYSA-N 0.000 description 1
- SFAZXBAPWCPIER-UHFFFAOYSA-N chloro-[chloro(dimethyl)silyl]-dimethylsilane Chemical compound C[Si](C)(Cl)[Si](C)(C)Cl SFAZXBAPWCPIER-UHFFFAOYSA-N 0.000 description 1
- GZGREZWGCWVAEE-UHFFFAOYSA-N chloro-dimethyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(C)Cl GZGREZWGCWVAEE-UHFFFAOYSA-N 0.000 description 1
- DBKNGKYVNBJWHL-UHFFFAOYSA-N chloro-dimethyl-octylsilane Chemical compound CCCCCCCC[Si](C)(C)Cl DBKNGKYVNBJWHL-UHFFFAOYSA-N 0.000 description 1
- JJRDHFIVAPVZJN-UHFFFAOYSA-N cyclotrisiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]1 JJRDHFIVAPVZJN-UHFFFAOYSA-N 0.000 description 1
- PFMKUUJQLUQKHT-UHFFFAOYSA-N dichloro(ethyl)silicon Chemical compound CC[Si](Cl)Cl PFMKUUJQLUQKHT-UHFFFAOYSA-N 0.000 description 1
- GYWBHBXGYTYXRG-UHFFFAOYSA-N dichloro-methyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(Cl)Cl GYWBHBXGYTYXRG-UHFFFAOYSA-N 0.000 description 1
- QHBMMABVNRSRHW-UHFFFAOYSA-N dichloro-methyl-octylsilane Chemical compound CCCCCCCC[Si](C)(Cl)Cl QHBMMABVNRSRHW-UHFFFAOYSA-N 0.000 description 1
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 1
- NBBQQQJUOYRZCA-UHFFFAOYSA-N diethoxymethylsilane Chemical compound CCOC([SiH3])OCC NBBQQQJUOYRZCA-UHFFFAOYSA-N 0.000 description 1
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 description 1
- 229960003493 octyltriethoxysilane Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- NFOHLBHARAZXFQ-UHFFFAOYSA-L platinum(2+);dihydroxide Chemical compound O[Pt]O NFOHLBHARAZXFQ-UHFFFAOYSA-L 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QFJIELFEXWAVLU-UHFFFAOYSA-H tetrachloroplatinum(2+) dichloride Chemical compound Cl[Pt](Cl)(Cl)(Cl)(Cl)Cl QFJIELFEXWAVLU-UHFFFAOYSA-H 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
- NKLYMYLJOXIVFB-UHFFFAOYSA-N triethoxymethylsilane Chemical compound CCOC([SiH3])(OCC)OCC NKLYMYLJOXIVFB-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- TUQLLQQWSNWKCF-UHFFFAOYSA-N trimethoxymethylsilane Chemical compound COC([SiH3])(OC)OC TUQLLQQWSNWKCF-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- G01N30/48—
-
- 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
- B01J20/282—Porous sorbents
- B01J20/283—Porous sorbents based on silica
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
Description
The present invention relates to a method for producing end capping filler, a filler and a fill column manufactured using the same, and more particularly to a method for manufacturing an end capping filler excellent in acid resistance and a filler and a fill column manufactured using the method.
Reversed phase chromatography fillers, in which functional groups are hydrocarbon based, are mostly used as silica gel fillers for HPLC. However, these fillers irreversibly interact with ionic compounds, especially basic compounds, and when used under strong acidic conditions, the durability of the column is rapidly deteriorated There is a problem such as. In particular, the effects are more pronounced when they are used for analyzing or sorting compounds such as peptides, proteins and nucleic acid bases.
It is known that the irreversible interaction is caused by silanol groups remaining after the reaction and trace amounts of metal ions remaining in the silica gel matrix (see Non-Patent Documents 1 and 2). In recent years, the purity of the silica gel for chromatography has been considerably improved, so that the effect on the coordination compound produced by the metal ion of the silica gel is considerably reduced.
One of the most well-known general methods is to add an organic base such as pyridine and reflux in a toluene solvent to remove the residual silanol groups. Trimethylchlorosilane (hereinafter referred to as 'TMS') (see Non-Patent Documents 3 and 4).
In addition, a method of reacting in a gas phase (see Patent Document 1) and a method of reacting in a supercritical fluid (see Patent Document 2 ) Are known. It is also known that two different kinds of organic bases are used for the reaction and the endcapping is divided into two or more times (see Patent Document 3).
As described above, many end capping methods have been disclosed, but a lot of reaction reagents, especially silylation reagents (see Non-Patent Document 6), have been much more.
Further, after C18 is bonded to the silica gel, TMS and hexamethyldisilazane (hereinafter referred to as "HMDS") are added at the same time to perform secondary end capping, and then TMS is used for the tertiary end capping (see Patent Document 4 ), Or a method in which end-capping is carried out in a gas phase using cyclosiloxane or HMDS at a temperature of 250 ° C or higher (see Patent Document 5).
Although there are many HPLC fillers prepared with the endcapping process disclosed in this prior art, it is difficult to say that any of the methods completely endcapped the remaining silanol groups. End capping is performed by dimethylsilylation of the silanol groups on the silica gel surface using TMS, HMDS, and cyclosiloxanes crosslinked at high temperatures, which are used as endcapping reagents. However, in practice, end capping of all silanol groups takes into consideration the three- It is difficult to see.
[Non-Patent Document]
- Non-Patent Document 1: M. Vezel and C. Dewaele, Chromatographia, 18 (1984) 314.
- Non-Patent Document 2: K. Kimata, N.Tanaka and T. Arai, J. Chromatogr., 594 (1992) 87.
Non-Patent Document 3: C.H. Lochmueller, and D. B. Marshall, Analitica Chimica Acta, 142 (1982) 63.
Non-Patent Document 4: N. Nagae, Y. Hatano and D. Ishi, Chromatography, 14 (1993) 45R.
Non-Patent Document 5: Y.Sakai, D.Hamakawa and S.Ohta, the 2 nd Technoplaza Proceedings, BP2 (1995) 51.
- Non-Patent Document 6: K.Sakaki, Separation Sciences, '94 Proceedings, 21P (1994).
[Patent Literature]
- Patent Document 1: Japanese Patent Publication No. 2611545 (Feb. 27, 1997)
- Patent Document 2: Japanese Patent Publication No. 2818857 (Aug. 28, 1998)
- Patent Document 3: JP-A-2003-172733 (Jun. 2003)
- Patent Document 4: JP-A-2008-232802 (2008.10.02)
- Patent Document 5: JP-A-1992-212058 (1992.08.03)
SUMMARY OF THE INVENTION Accordingly, the present invention has been made to solve the above problems, and it is an object of the present invention to provide a hydrocarbon-based filler for HPLC which is capable of highly endcapping a silanol group on the surface of a silica gel to prevent a polar compound from being adsorbed, A method for producing an improved filler, and a filler and a packed column manufactured using the same.
According to an aspect of the present invention, there is provided a method for producing a hydrocarbon-based silica gel filler, comprising the steps of: (1) mixing silica gel with chlorosilane or alkoxysilane containing an alkyl group or aryl group having 2 to 30 carbon atoms; and a first step of reacting an unreacted chloro group or an alkoxy group with a silanol group after the coupling step of reacting the compound with an alkoxysilane, do.
Also, in the coupling step, the unreacted silanol groups and the silanol groups remaining on the surface of the silica gel may be replaced with an organic hydrogenation silane, an organic hydrogenation siloxane, an organic chlorosilane, , A second step of reacting with an organic alkoxysiloxane, an organic chlorosiloxane, an organic alkoxysilane or an organic alkoxysiloxane to form a multi-stage silanol layer.
Also included is a third step of crosslinking the formed multistage silanol groups with organic chlorosiloxane, organic hydrogenation cyclosiloxane or organic cyclosiloxane having two crosslinking points to cover the silicon with silicon The method comprising the steps of:
Also, when the above reaction is carried out with an organic hydrogenation silane, an organic hydrogenation siloxane or an organic hydrogenation cyclosiloxane, an alkene having 1 to 30 carbon atoms is added to form a hydrocarbon functional group And a fourth step of introducing a further step.
And a fifth step of end capping the unreacted silanol group by adding an end capping reagent to the filler into which the hydrocarbon functional group is introduced.
In order to solve the above-mentioned other problems, the present invention provides a filler produced by the above method.
In order to solve the above-mentioned problem, the present invention provides a packing column filled with the filler.
According to the present invention, in the preparation of fillers for HPLC, a silane coupling reagent having a hydrocarbon-based functional group usable for an HPLC filler is reacted with a silica gel to bind a functional group, and then a silanol group And residual silanol groups on the surface of the silica gel are further treated with an organic hydrogenation silane, an organic hydrogenation siloxane, an organic chlorosilane, an organic chlorosiloxane, an organic alkoxysilane ) Or organic alkoxysiloxane to form a new multistage silanol layer followed by an organic chlorosiloxane with two crosslinking points, an organic hydrogenation cyclosiloxane or an organic cyclosiloxane ), Followed by coating with silicone An organic hydrogenation silane, an organic hydrogenation siloxane or an organic hydrogenation cyclosiloxane to further introduce hydrocarbon functional groups, followed by end-capping the remaining silanol groups, that is, The present invention can provide a method for producing a filler that is highly end-capped and does not adsorb a polar compound and is excellent in acid resistance, and a filler and a packed column manufactured using the method.
Hereinafter, preferred embodiments of the present invention will be described in detail with reference to the accompanying drawings. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described in detail with reference to the accompanying drawings.
The present invention relates to a method for producing a hydrocarbon-based silica gel filler, which comprises the steps of: coupling silica gel with chlorosilane or alkoxysilane containing an alkyl group having 2 to 30 carbon atoms or an aryl group; And a first step of replacing the unreacted chloro group or alkoxy group with a silanol group after the coupling step.
In the first step, preferably, the unreacted chloro group or alkoxy group is converted into a silanol group, and the subsequent steps are surely proceeded, whereby the hydrocarbon-based silica gel filler can be efficiently produced.
The organic silane coupling reagent which can be used in the first step is not particularly limited. For example, in the case of commonly used C18, octadecyldimethylchlorosilane, octadecylmethyldichlorosilane, But are not limited to, octadecyltrichlorosilane, octadecyltrimethoxysilane, octadecyltriethoxysilane, 1,3,5,7-tetraoctadecyl-1,3,5,7-tetra 1,3,5,7-tetramethylcyclotetrasiloxane and the like can be preferably used, and more preferably, Octadecyltrimethoxysilane may be used.
Similarly, in the case of C8, octyldimethylchlorosilane, octylmethyldichlorosilane, octyltrichlorosilane, octyltrimethoxysilane, octyltriethoxysilane, and the like may be used. And more preferably, octyltrichlorosilane or octyltrimethoxysilane can be used.
Similarly, in the case of C4, various silane agents in which the alkyl group is n-butyl can be preferably used, and more preferably n-butyltrichlorosilane or butyl Butyltrimethoxysilane may be used.
In addition, group wherein the alkyl group is an aryl, such as phenyl ethyl (phenylethyl) group (C 6 H 5 - (CH 2) 2 - group; 2-Phenyl) or phenyl-hexyl (phenylhexyl) group (C 6 H 5 - (CH 2) 6 6-phenyl) chlorosilane or alkoxysilane may be preferably used, and trichlorosilane or trimethoxysilane may be more preferably used.
Also, 3-cyanopropyldimethylchlorosilane, 3-cyanopropylmethylchlorosilane, 3-cyanopropyltrichlorosilane, and the like, each having a cyanopropyl group, Can be used, and preferably 3-cyanopropyltrichlorosilane can be used.
The organosilane coupling reagent may be a hydrocarbon compound having a double bond or a triple bond in addition to the above, and is not necessarily limited to the above compounds.
In the present invention, the unreacted silanol groups and the silanol groups remaining on the surface of the silica gel in the coupling process may be replaced with organic hydrogenation silanes, organic hydrogenation siloxanes, organic chlorosilanes (organic and a second step of forming a multistage silanol layer by reacting with chlorosilane, organic chlorosiloxane, organic alkoxysilane or organic alkoxysiloxane.
By forming a new multistage silanol layer according to the second process, the hydrocarbon-based silica gel filler can be efficiently produced by making silicon bridging and end capping more convenient.
The organic hydrogenation silane or organic hydrogenation siloxane having 8 or less carbon atoms is not particularly limited and preferably trichlorosilane, dichlorosilane, dichloromethylsilane, For example, dichloroethylsilane, trimethoxysilane, dimethoxysilane, dimethoxymethylsilane, dimethoxyethylsilane, triethoxysilane, diethoxysilane, diethoxysilane, diethoxymethylsilane, diethoxyethylsilane, or 1,1-dichloro-3,3-dimethylpropanedisiloxane may be used as the organic solvent. And more preferably dichloromethylsilane or dialkoxymethylsilane is used. There.
Also, it is not particularly limited as to the organic chlorosilane, organic chlorosiloxane, organic alkoxysilane or organic alkoxysiloxane having a carbon number of 8 or less, but it is preferably tetrachlorosilane (such as tetrachlorosilane, ethyltrichlorosilane, dimethyldichlorosilane, ethyltrichlorosilane, diethyldichlorosilane, 1,2-dichlorotetramethyldisilane, ), 1,3-dichloro-1,1,3,3-tetramethyldisiloxane, 1,5-dichloro-1,1,3, 1,5-dichloro-1,1,3,3,5,5-hexamethyltrisiloxane, tetramethoxysilane, trimethoxymethylsilane, dimethoxymethylsilane, Dimethoxydimethylsilane, tetra Tetraethoxysilane, triethoxymethylsilane or diethoxydimethylsilane can be used. More preferably, dimethyldichlorosilane or dimethoxydimethylsilane can be used.
Here, a compound having two or more chloro groups or alkoxy groups capable of reacting with a silanol group by a functional group and capable of converting unreacted functional groups into silanol groups after the reaction can be used more effectively.
The reaction of the silanol group remaining in the second step with the organic hydrogenated silane or the organic hydrogenated siloxane having a carbon number of 8 or less can be carried out in a liquid phase process involving a chloro group in the presence of a volatile benzene, dichloromethane, 10% by weight or less of a silicon compound solution dissolved in chloroform or the like is added in an amount of 0.001 to 0.2 part by weight per 1 part by weight of the carrier prepared in the first step and the mixture is heated in an inert gas atmosphere at a temperature of 50 to 200 占 폚 Stirring for 2 hours or more, and adding 0.001 to 0.1 part by weight of a base such as pyridine to react.
In the liquid phase method involving an alkoxy group, the reaction is carried out in the same manner as above, or without removing a base such as pyridine, while refluxing in an inert gas atmosphere while removing the alcohol. If the reaction does not proceed well, add a small amount of weak acid (such as acetic acid) or weak base (such as ammonium hydroxide). Each is filtered, washed with chloroform and tetrahydrofuran (THF), and an alcohol aqueous solution is added after the alcohol is replaced to convert the unreacted group to a silanol group. The organic chlorosilane, organic chlorosiloxane, organic alkoxysilane or organic alkoxysiloxane having 8 or less carbon atoms can also be reacted in the same manner as described above to convert an unreacted group into a silanol group.
The present invention relates to a third step of crosslinking the formed multistage silanol groups with an organic chlorosiloxane, an organic hydrogenation cyclosiloxane or an organic cyclosiloxane having two crosslinking points, . ≪ / RTI >
The silanol groups formed in multiple steps according to the third step may be crosslinked, that is, coated with silicon, to efficiently produce a highly end-capped hydrocarbon-based silica gel filler.
Examples of the organic hydrogenation cyclosiloxane or organic cyclosiloxane used in the silicon coating in the third step include 1,3,5-trimethyl trihydrogenation (1,3,5-trimethyl trihydrogenation) cyclotrisiloxane, 1,3,5,7-tetramethyl tetrahydrogenation cyclotetrasiloxane, 1,3,5,7,9-pentamethylpenta-hydrogenated cyclopentasiloxane ( Cyclosiloxane such as 1,3,5,7,9-pentamethyl pentahydrogenation cyclopentasiloxane, hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane and decamethylcyclopentanesiloxane, and the like. Can be preferably used, and tetramethyl tetrahydrogenation cyclotetrasiloxane (1,3,5,7-tetramethylcyclot etrasiloxane and hexamethylcyclotrisiloxane are particularly preferably used.
Examples of the organic chlorosiloxane include 1,3-dichloro-1,1,3,3-tetramethyldisiloxane, 1,5-dichloro-1,1,3,3-tetramethyldisiloxane, - 1,5-dichloro-1,1,3,3,5,5-hexamethyltrisiloxane or 1,1-dichloro-3,3-dichloro-1,1,3,3,5,5-hexamethyltrisiloxane. (1,1-dichloro-3,3-dimethylpropanedisiloxane) can be preferably used.
Also, organic chlorosilane can be used, and 1,2-dichlorotetramethylsilane, 1,3-dichlorohexamethyltrisilane, 1,4-dichlorohexamethyltrisilane, 1,4-dichlorooctamethyltetrasilane or 1,5-dichlorodecamethylpentasilane can be preferably used.
In the present invention, when an organic hydrogenation silane, an organic hydrogenation siloxane or an organic hydrogenation cyclosiloxane is reacted with an alkene having 1 to 30 carbon atoms, And a fourth step of further introducing a functional group.
According to the fourth step, an alkyl group is further introduced using an alkene having 1 to 30 carbon atoms, whereby a filler having a large number of functional groups can be efficiently produced.
In the second step and the third step, a method of bonding a functional group to a SiH group of a carrier reacted with an organic hydrogenation silane or an organic hydrogenation siloxane can be carried out by using a known method such as 1-butene (1 butene, 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-octadecene, 1-isoalkenes such as 1-alkene and 4-methyl-1-heptene, such as 1-decene, Platinum or the like is added as a catalyst with 1-aromatic alkene such as 1-alkenylbenzene and reacted in dry toluene at 50 to 300 ° C for 2 hours or more in an inert gas atmosphere The hydrocarbon-based functional group can be newly introduced by the fourth step.
The palladium compound used as the catalyst is not particularly limited, but palladium (II) chloride, tetraammine palladium (II) chloride, palladium hydroxide (II) chloride, (II) (platinum chloride (II)), platinum tetrachloride (II), and platinum tetrachloride (II) are preferably used. ), Platinum hexachloride (IV), platinum hydroxide (II), and the like can be suitably used.
The carrier prepared in the fourth step is sufficiently washed with chloroform or THF after the filtration, and after the alcohol substitution, an alcohol aqueous solution is added to convert the whole into a silanol group, and vacuum drying can be performed at 105 ° C for 2 hours or more.
The present invention may include a fifth step of end-capping unreacted silanol groups by adding an end-capping reagent to the filler into which the hydrocarbon-based functional group is introduced.
According to the fifth step, a highly end-capped filler having excellent acid resistance can be efficiently produced. Specifically, a filler prepared according to the first to third steps, that is, a silicon-coated filler obtained by reacting an organic silane or an organic siloxane, or a filler prepared according to the first to fourth steps , That is, after the silicon coating, the filler having a hydrocarbon functional group introduced thereinto is end-capped with an end capping agent containing trimethylsilyl group to reduce the unreacted silanol group.
Since a small amount of silanol groups remaining in the carrier prepared according to the first step to the third step or the first step to the fourth step is formed in a multistage manner and the steric hindrance is small, End capping is possible. On the other hand, if the silanol groups are ideally formed in multiple stages in the second step, the process may proceed directly to the next step.
The carrier prepared in the fifth step is sufficiently washed with chloroform or THF after filtration, and can be vacuum-dried at 105 ° C for 2 hours or more in an inert gas atmosphere.
The preferred embodiments of the present invention have been described in detail with reference to the drawings. It will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the appended claims.
Accordingly, the scope of the present invention is defined by the appended claims rather than the detailed description, and all changes or modifications derived from the meaning, range, and equivalence of the claims are included in the scope of the present invention Should be interpreted.
Claims (7)
A coupling process in which silica gel is reacted with chlorosilane or alkoxysilane containing an alkyl group or an aryl group having 2 to 30 carbon atoms and an unreacted chloro ) Group or an alkoxy group with a silanol group.
In the coupling step, unreacted silanol groups and silanol groups remaining on the surface of the silica gel are reacted with an organic hydrogenation silane, an organic hydrogenation siloxane, an organic chlorosilane, And a second step of forming a multi-stage silanol layer by reacting with an organic chlorosiloxane, an organic alkoxysilane or an organic alkoxysiloxane.
And a third step of crosslinking the formed multistage silanol groups with an organic chlorosiloxane, an organic hydrogenation cyclosiloxane or an organic cyclosiloxane having two crosslinking points to cover the silicon ≪ / RTI >
When an organic hydrogenation silane, an organic hydrogenation siloxane or an organic hydrogenation cyclosiloxane is reacted, an alkene having 1 to 30 carbon atoms is added to form a hydrocarbon functional group And a fourth step of introducing the compound.
And a fifth step of end-capping the unreacted silanol group by adding an end capping reagent to the filler into which the hydrocarbon-based functional group is introduced.
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