JP2010184928A - 硫黄含有有機シリコン化合物を調製する方法 - Google Patents
硫黄含有有機シリコン化合物を調製する方法 Download PDFInfo
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- JP2010184928A JP2010184928A JP2010100150A JP2010100150A JP2010184928A JP 2010184928 A JP2010184928 A JP 2010184928A JP 2010100150 A JP2010100150 A JP 2010100150A JP 2010100150 A JP2010100150 A JP 2010100150A JP 2010184928 A JP2010184928 A JP 2010184928A
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- Prior art keywords
- compound
- sulfur
- organosilicon compound
- alk
- organic phase
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 229910052717 sulfur Inorganic materials 0.000 title claims abstract description 58
- 239000011593 sulfur Substances 0.000 title claims abstract description 54
- 238000000034 method Methods 0.000 title claims abstract description 43
- 150000003961 organosilicon compounds Chemical class 0.000 title claims abstract description 38
- 239000000203 mixture Substances 0.000 claims abstract description 56
- -1 sulfide compound Chemical class 0.000 claims abstract description 43
- 239000008346 aqueous phase Substances 0.000 claims abstract description 26
- 229910000077 silane Inorganic materials 0.000 claims abstract description 22
- 238000010438 heat treatment Methods 0.000 claims abstract description 15
- 239000000872 buffer Substances 0.000 claims abstract description 13
- 150000002430 hydrocarbons Chemical group 0.000 claims abstract description 11
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 239000012074 organic phase Substances 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 10
- 239000012071 phase Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 8
- 150000003464 sulfur compounds Chemical class 0.000 claims description 8
- 239000002274 desiccant Substances 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 6
- 235000011152 sodium sulphate Nutrition 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 5
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 239000001110 calcium chloride Substances 0.000 claims description 3
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 3
- 235000011148 calcium chloride Nutrition 0.000 claims description 3
- 235000011132 calcium sulphate Nutrition 0.000 claims description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 claims description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 3
- 235000011147 magnesium chloride Nutrition 0.000 claims description 3
- 239000002808 molecular sieve Substances 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 150000003377 silicon compounds Chemical class 0.000 claims description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- 229910021536 Zeolite Inorganic materials 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 32
- 150000007514 bases Chemical class 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 238000002845 discoloration Methods 0.000 abstract 1
- 125000002346 iodo group Chemical group I* 0.000 abstract 1
- 239000011369 resultant mixture Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000000047 product Substances 0.000 description 34
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 24
- 239000011734 sodium Substances 0.000 description 21
- 239000007864 aqueous solution Substances 0.000 description 15
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 230000008569 process Effects 0.000 description 9
- 239000007789 gas Substances 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000004445 quantitative analysis Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000005046 Chlorosilane Substances 0.000 description 4
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- IKBFHCBHLOZDKH-UHFFFAOYSA-N 2-chloroethyl(triethoxy)silane Chemical compound CCO[Si](CCCl)(OCC)OCC IKBFHCBHLOZDKH-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- IIFBEYQLKOBDQH-UHFFFAOYSA-N 3-chloropropyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)CCCCl IIFBEYQLKOBDQH-UHFFFAOYSA-N 0.000 description 1
- VJPGPCCOXUQRLT-UHFFFAOYSA-N 4-chlorobutyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCl VJPGPCCOXUQRLT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 1
- 101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 1
- DJRSJHZEOJHZER-UHFFFAOYSA-N [SiH4].SS Chemical compound [SiH4].SS DJRSJHZEOJHZER-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000006172 buffering agent Substances 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
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- ZMZCDKKVGLGCSJ-UHFFFAOYSA-N chloromethoxy-methoxy-methyl-(2-methylpropyl)silane Chemical compound CC(C)C[Si](C)(OC)OCCl ZMZCDKKVGLGCSJ-UHFFFAOYSA-N 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- MMHCDZUIHWASJS-UHFFFAOYSA-N diethoxy-methyl-(2-methylpropyl)silane Chemical compound CCO[Si](C)(CC(C)C)OCC MMHCDZUIHWASJS-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IUVXCVGGLRYGFE-UHFFFAOYSA-N tetraphenyl-lambda5-arsane hydrochloride Chemical compound C1=CC=C(C=C1)[AsH](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.Cl IUVXCVGGLRYGFE-UHFFFAOYSA-N 0.000 description 1
- NZUQEBQRKNZZDO-UHFFFAOYSA-M tetraphenylarsanium;bromide Chemical compound [Br-].C1=CC=CC=C1[As+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NZUQEBQRKNZZDO-UHFFFAOYSA-M 0.000 description 1
- IKRMQEUTISXXQP-UHFFFAOYSA-N tetrasulfane Chemical compound SSSS IKRMQEUTISXXQP-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- DWAWYEUJUWLESO-UHFFFAOYSA-N trichloromethylsilane Chemical compound [SiH3]C(Cl)(Cl)Cl DWAWYEUJUWLESO-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
【解決手段】式(RO)3−mRmSi−Alk−Sn−Alk−SiRm(OR)3−mを持つ硫黄含有有機シリコン化合物を生産する方法であって(式中、Rは独立に、1〜12炭素原子を持つ1価の炭化水素を表し、Alkは、1〜18炭素原子を持つ2価の炭化水素を表し、mは、0、1、もしくは2を表す整数であり、nは、2〜8の値を有する整数である)、式M2SnもしくはMHS(式中、Hは水素、Mはアンモニウムもしくはアルカリ金属、nは1〜8)を持つスルフィド化合物(A)を、式(RO)3−mRmSi−Alk−X(式中、Xは、Cl、Br、もしくはI、mは、0、1、もしくは2)を持つシラン化合物(B)および硫黄(C)と、相間移動触媒の存在下に加熱し反応させ、水相が緩衝剤もしくは塩基性化合物を含有し、生成混合物を形成するステップ(I)、該生成混合物を80〜100℃へと加熱するステップ(II)、ならびに、該生成混合物から前記有機シリコン化合物を分離するステップ(III)を含む方法とする。
【選択図】なし
Description
Claims (9)
- 式(RO)3−mRmSi−Alk−Sn−Alk−SiRm(OR)3−mを持つ硫黄含有有機シリコン化合物を生産する方法であって(式中、Rは独立に、1〜12炭素原子を持つ1価の炭化水素を表し、Alkは、1〜18炭素原子を持つ2価の炭化水素を表し、mは、0、1、もしくは2を表す整数であり、nは、2〜8の値を有する整数である)、式M2SnもしくはMHS(式中、Hは水素、Mはアンモニウムもしくはアルカリ金属、nは1〜8)を持つスルフィド化合物(A)を、式(RO)3−mRmSi−Alk−X(式中、Xは、Cl、Br、もしくはI、mは、0、1、もしくは2)を持つシラン化合物(B)および硫黄(C)と、相間移動触媒の存在下に加熱し反応させ、水相が緩衝剤もしくは塩基性化合物を含有し、生成混合物を形成するステップ(I)、該生成混合物を80〜100℃へと加熱するステップ(II)、ならびに、該生成混合物から前記有機シリコン化合物を分離するステップ(III)を含む方法。
- 前記生成混合物へと水もしくは稀釈酸溶液を加えること(D)と、該生成混合物を水相中および前記有機シリコン化合物を含有する有機相中へと相分離させること(E)とにより、該有機シリコン化合物が該生成混合物から分離される、請求項1に記載の方法。
- シラン化合物(B)に対する前記水もしくは稀釈酸溶液の重量%が10〜50%である、請求項2に記載の方法。
- 前記有機シリコン化合物を含有する前記有機相が、減圧下に該有機相を加熱することにより乾燥される、請求項2に記載の方法。
- 前記有機シリコン化合物を含有する前記有機相が、該有機相を、硫酸ナトリウム、硫酸マグネシウム、硫酸カルシウム、塩化カルシウム、塩化マグネシウム、塩化リチウム、モレキュラー・シーブズ、ゼオライト、アルミナシリケート、およびシリカゲルからなる群から選択される固体乾燥剤と接触させることにより乾燥される、請求項2に記載の方法。
- 前記有機シリコン化合物を含有する前記有機相を15℃以下の温度へと冷却して未反応硫黄化合物を沈澱させる追加ステップ(F)と、前記有機シリコン化合物を含有する前記有機相をこの沈澱させられた未反応硫黄化合物から分離させる追加ステップ(G)とを含む、請求項2に記載の方法。
- 冷却ステップ(F)が、−20〜10℃の範囲中の温度下である、請求項6に記載の方法。
- ステップ(II)における前記加熱が、85〜95℃の温度下である、請求項1に記載の方法。
- 請求項1に記載の方法により調製される、硫黄含有有機シリコン化合物。
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US10/293,841 US6740767B1 (en) | 2002-11-12 | 2002-11-12 | Method of making sulfur containing organosilicon compounds |
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EP (1) | EP1562962B1 (ja) |
JP (2) | JP4578245B2 (ja) |
KR (1) | KR100990043B1 (ja) |
CN (1) | CN100347178C (ja) |
AU (1) | AU2003301910A1 (ja) |
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CN1305879C (zh) * | 2004-06-09 | 2007-03-21 | 上海人怡精细化工有限公司 | 一种相转移催化剂制造硅-69的工艺 |
KR100636296B1 (ko) * | 2005-03-21 | 2006-10-19 | 한국과학기술연구원 | (유기티오메틸)클로로실란 유도체와 이의 제조방법 |
DE102005037690A1 (de) | 2005-08-10 | 2007-02-15 | Degussa Ag | Verfahren zur Herstellung von Organosiliciumverbindungen |
DE102006041356A1 (de) * | 2006-09-01 | 2008-03-20 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Organosilanen |
DE102007037556A1 (de) | 2007-08-09 | 2009-02-12 | Evonik Degussa Gmbh | Verfahren zur Herstellung von alkylpolyethersubstituierten Mercaptosilanen |
CN101885734B (zh) * | 2010-06-26 | 2012-05-23 | 丁爱梅 | 一种双-[丙基三乙氧基硅烷]-四硫化物的合成方法 |
KR20170011291A (ko) | 2015-07-22 | 2017-02-02 | 주식회사 투넘버 | 컬러코드 기반의 인터랙티브 교육시스템 |
CN108219175A (zh) * | 2017-12-29 | 2018-06-29 | 兴科电子(东莞)有限公司 | 一种带色点的硅胶产品的制备工艺 |
CN109180719A (zh) * | 2018-09-03 | 2019-01-11 | 东营市金凤凰化工股份有限公司 | 一种液碱制备硅69的工艺及生产系统 |
EP3838905A1 (de) | 2019-12-18 | 2021-06-23 | Evonik Operations GmbH | Verfahren zur herstellung von polysulfansilanen mittels phasentransferkatalyse |
DE102020211042A1 (de) | 2020-09-02 | 2022-03-03 | Evonik Operations Gmbh | Verfahren zur Herstellung von Polysulfansilanen mittels Phasentransferkatalyse |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0853473A (ja) * | 1994-07-08 | 1996-02-27 | Goodyear Tire & Rubber Co:The | 硫黄含有有機ケイ素化合物の製造方法 |
JPH101488A (ja) * | 1996-03-06 | 1998-01-06 | Goodyear Tire & Rubber Co:The | 硫黄含有有機珪素化合物の製造方法 |
JP2000103794A (ja) * | 1998-04-10 | 2000-04-11 | Daiso Co Ltd | 含硫黄有機珪素化合物の製造方法およびその合成中間体の製造方法 |
JP2001039985A (ja) * | 1999-07-01 | 2001-02-13 | Degussa Huels Ag | 多硫化シラン化合物の製造法 |
JP2002121196A (ja) * | 2000-09-13 | 2002-04-23 | Degussa Ag | 黄色のビス(3−[トリエトキシシリル]プロピル)ポリスルファンの製造方法 |
US6384256B1 (en) * | 2001-06-29 | 2002-05-07 | Dow Corning Corporation | Process for the preparation of sulfur-containing organosilicon compounds |
JP2004521946A (ja) * | 2001-06-29 | 2004-07-22 | ダウ・コーニング・コーポレイション | 硫黄含有有機シロキサン化合物の調製方法 |
JP2005505512A (ja) * | 2001-06-29 | 2005-02-24 | ダウ・コーニング・コーポレイション | 緩衝相間移動触媒法を用いるイオウ含有有機ケイ素化合物の製造方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4125552A (en) * | 1975-12-29 | 1978-11-14 | Dow Corning Corporation | Preparation of alkyl polysulfides |
US5405985A (en) * | 1994-07-08 | 1995-04-11 | The Goodyear Tire & Rubber Company | Preparation of sulfur-containing organosilicon compounds |
US5663396A (en) * | 1996-10-31 | 1997-09-02 | The Goodyear Tire & Rubber Company | Preparation of sulfur-containing organosilicon compounds |
US6172251B1 (en) * | 1998-07-24 | 2001-01-09 | The Goodyear Tire & Rubber Company | Solid/liquid phase transfer system |
US6294683B1 (en) * | 1999-01-19 | 2001-09-25 | The Goodyear Tire & Rubber Company | Solid/liquid phase transfer system |
US6384255B1 (en) * | 2001-06-29 | 2002-05-07 | Dow Corning Corporation | Process for the preparation of sulfur-containing organosilicon compounds |
-
2002
- 2002-11-12 US US10/293,841 patent/US6740767B1/en not_active Expired - Lifetime
-
2003
- 2003-10-17 KR KR1020057008405A patent/KR100990043B1/ko active IP Right Grant
- 2003-10-17 AU AU2003301910A patent/AU2003301910A1/en not_active Abandoned
- 2003-10-17 JP JP2004551544A patent/JP4578245B2/ja not_active Expired - Lifetime
- 2003-10-17 CN CNB2003801031115A patent/CN100347178C/zh not_active Expired - Lifetime
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- 2003-10-17 EP EP03811236.3A patent/EP1562962B1/en not_active Expired - Lifetime
- 2003-10-22 TW TW092129263A patent/TW200415147A/zh unknown
-
2010
- 2010-04-23 JP JP2010100150A patent/JP2010184928A/ja active Pending
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0853473A (ja) * | 1994-07-08 | 1996-02-27 | Goodyear Tire & Rubber Co:The | 硫黄含有有機ケイ素化合物の製造方法 |
JPH101488A (ja) * | 1996-03-06 | 1998-01-06 | Goodyear Tire & Rubber Co:The | 硫黄含有有機珪素化合物の製造方法 |
JP2000103794A (ja) * | 1998-04-10 | 2000-04-11 | Daiso Co Ltd | 含硫黄有機珪素化合物の製造方法およびその合成中間体の製造方法 |
JP2001039985A (ja) * | 1999-07-01 | 2001-02-13 | Degussa Huels Ag | 多硫化シラン化合物の製造法 |
JP2002121196A (ja) * | 2000-09-13 | 2002-04-23 | Degussa Ag | 黄色のビス(3−[トリエトキシシリル]プロピル)ポリスルファンの製造方法 |
US6384256B1 (en) * | 2001-06-29 | 2002-05-07 | Dow Corning Corporation | Process for the preparation of sulfur-containing organosilicon compounds |
JP2004521946A (ja) * | 2001-06-29 | 2004-07-22 | ダウ・コーニング・コーポレイション | 硫黄含有有機シロキサン化合物の調製方法 |
JP2005505512A (ja) * | 2001-06-29 | 2005-02-24 | ダウ・コーニング・コーポレイション | 緩衝相間移動触媒法を用いるイオウ含有有機ケイ素化合物の製造方法 |
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TW200415147A (en) | 2004-08-16 |
EP1562962B1 (en) | 2013-05-22 |
KR100990043B1 (ko) | 2010-10-26 |
EP1562962A1 (en) | 2005-08-17 |
KR20050074595A (ko) | 2005-07-18 |
US20040092758A1 (en) | 2004-05-13 |
US6740767B1 (en) | 2004-05-25 |
WO2004043969A1 (en) | 2004-05-27 |
CN100347178C (zh) | 2007-11-07 |
JP4578245B2 (ja) | 2010-11-10 |
JP2006506421A (ja) | 2006-02-23 |
CN1711274A (zh) | 2005-12-21 |
AU2003301910A1 (en) | 2004-06-03 |
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