JP2013508271A - オルガノハロシランの製造方法 - Google Patents
オルガノハロシランの製造方法 Download PDFInfo
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- JP2013508271A JP2013508271A JP2012534190A JP2012534190A JP2013508271A JP 2013508271 A JP2013508271 A JP 2013508271A JP 2012534190 A JP2012534190 A JP 2012534190A JP 2012534190 A JP2012534190 A JP 2012534190A JP 2013508271 A JP2013508271 A JP 2013508271A
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- 238000004519 manufacturing process Methods 0.000 title abstract description 23
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 182
- 239000010703 silicon Substances 0.000 claims abstract description 178
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 178
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 86
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 85
- 238000000034 method Methods 0.000 claims abstract description 75
- 230000008569 process Effects 0.000 claims abstract description 33
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910052802 copper Inorganic materials 0.000 claims abstract description 24
- 239000010949 copper Substances 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 150000004820 halides Chemical class 0.000 claims description 30
- 239000002245 particle Substances 0.000 claims description 17
- 238000009826 distribution Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- 229910045601 alloy Inorganic materials 0.000 claims description 8
- 239000000956 alloy Substances 0.000 claims description 8
- -1 copper nitride Chemical class 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 6
- 229910052787 antimony Inorganic materials 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 5
- 229910052718 tin Inorganic materials 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 4
- 239000005751 Copper oxide Substances 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052785 arsenic Inorganic materials 0.000 claims description 4
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052792 caesium Inorganic materials 0.000 claims description 4
- 229910000431 copper oxide Inorganic materials 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 2
- 239000005750 Copper hydroxide Substances 0.000 claims description 2
- 229910017518 Cu Zn Inorganic materials 0.000 claims description 2
- 229910017758 Cu-Si Inorganic materials 0.000 claims description 2
- 229910017752 Cu-Zn Inorganic materials 0.000 claims description 2
- 229910017932 Cu—Sb Inorganic materials 0.000 claims description 2
- 229910017931 Cu—Si Inorganic materials 0.000 claims description 2
- 229910017943 Cu—Zn Inorganic materials 0.000 claims description 2
- 229940075103 antimony Drugs 0.000 claims description 2
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 claims description 2
- 150000001463 antimony compounds Chemical class 0.000 claims description 2
- 229940091658 arsenic Drugs 0.000 claims description 2
- 150000001495 arsenic compounds Chemical class 0.000 claims description 2
- 229910001956 copper hydroxide Inorganic materials 0.000 claims description 2
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 claims description 2
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 claims description 2
- 229940093920 gynecological arsenic compound Drugs 0.000 claims description 2
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 2
- 150000003606 tin compounds Chemical class 0.000 claims description 2
- 150000003752 zinc compounds Chemical class 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000004044 response Effects 0.000 abstract description 2
- 229910000789 Aluminium-silicon alloy Inorganic materials 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical group C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000004939 coking Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229940050176 methyl chloride Drugs 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- CSDREXVUYHZDNP-UHFFFAOYSA-N alumanylidynesilicon Chemical compound [Al].[Si] CSDREXVUYHZDNP-UHFFFAOYSA-N 0.000 description 2
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- SLLGVCUQYRMELA-UHFFFAOYSA-N chlorosilicon Chemical compound Cl[Si] SLLGVCUQYRMELA-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- BYLOHCRAPOSXLY-UHFFFAOYSA-N dichloro(diethyl)silane Chemical compound CC[Si](Cl)(Cl)CC BYLOHCRAPOSXLY-UHFFFAOYSA-N 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000005272 metallurgy Methods 0.000 description 2
- 239000005055 methyl trichlorosilane Substances 0.000 description 2
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 229910018182 Al—Cu Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910004706 CaSi2 Inorganic materials 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- 229910015372 FeAl Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910000676 Si alloy Inorganic materials 0.000 description 1
- 229910002796 Si–Al Inorganic materials 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- CAVCGVPGBKGDTG-UHFFFAOYSA-N alumanylidynemethyl(alumanylidynemethylalumanylidenemethylidene)alumane Chemical compound [Al]#C[Al]=C=[Al]C#[Al] CAVCGVPGBKGDTG-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 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
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- MNKYQPOFRKPUAE-UHFFFAOYSA-N chloro(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 MNKYQPOFRKPUAE-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SRIHMZCTDWKFTQ-UHFFFAOYSA-N dibromo(diethyl)silane Chemical compound CC[Si](Br)(Br)CC SRIHMZCTDWKFTQ-UHFFFAOYSA-N 0.000 description 1
- LIQOCGKQCFXKLF-UHFFFAOYSA-N dibromo(dimethyl)silane Chemical compound C[Si](C)(Br)Br LIQOCGKQCFXKLF-UHFFFAOYSA-N 0.000 description 1
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 1
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Chemical group 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000005048 methyldichlorosilane Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- 238000001637 plasma atomic emission spectroscopy Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- FSLGCYNKXXIWGJ-UHFFFAOYSA-N silicon(1+) Chemical compound [Si+] FSLGCYNKXXIWGJ-UHFFFAOYSA-N 0.000 description 1
- 239000011856 silicon-based particle Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- C07F7/12—Organo silicon halides
- C07F7/16—Preparation thereof from silicon and halogenated hydrocarbons direct synthesis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
(i)反応器内において、銅を含む直接法触媒および促進剤の存在下、250〜350℃で、0.08〜0.25%(w/w)のアルミニウムを含む第一の微粉化したケイ素と、有機ハロゲン化物とを接触させる工程と、
(ii)前記反応器内に、未反応のケイ素およびアルミニウムの総重量に基づき、0.08〜0.2%(w/w)のアルミニウム濃度を維持するために十分な量の要求に応じた、0.001〜0.10%未満(w/w)のアルミニウムを含む第二の微粉化したケイ素を投入する工程と、
を具えるオルガノハロシランの製造方法を対象とする。
(i)反応器内において、銅を含む直接法触媒および促進剤の存在下、250〜350℃で、0.08〜0.25%(w/w)のアルミニウムを含む第一の微粉化したケイ素と、有機ハロゲン化物とを接触させる工程と、
(ii)前記反応器内に、未反応のケイ素およびアルミニウムの総重量に基づき、0.08〜0.2%(w/w)のアルミニウム濃度を維持するために十分な量の要求に応じた、0.001〜0.10%未満(w/w)のアルミニウムを含む第二の微粉化したケイ素を投入する工程と、
を具える。
RaHbSiX4−a−b(II)
式中、Rは、炭化水素基、Xは、ハロゲンである。Rで表わされる炭化水素基およびXで表わされるハロゲンは、有機ハロゲン化物において上述し、例示したものと同様である。
振動炭素鋼管反応器(長さ12インチ、内径0.5インチ)において、不活性ガス条件下で、本明細書で上述したように、粉末にしたケイ素38.4gを銅触媒および促進剤と混合した。その反応塊状物と共に反応器を250℃、窒素フロー下において30分間予熱した。その前処理の後、温度を320℃に上げて、塩化メチル(MeCl)を流速10gh−1で投入した。(i)化学等級ケイ素(C−Si)、(ii)高純度ケイ素(E−Si)、および(iii)銅触媒と共にアルミニウムを加えてアルミニウム濃度を0.12重量%(w/w)とした高純度ケイ素(E−Si)、のケイ素の3つの等級を試験した。ケイ素(i)および(iii)は、第一の微粉化したケイ素の例である。
触媒の一部としてアルミニウムを加えた低AlSiを用いて、例1において述べた方法と同様の方法により反応を行った。表3の結果は、低AlSiはケイ素変換が低いが、アルミニウムを加えた低AlSiは、ケイ素変換および選択性において、化学等級ケイ素と同程度または化学等級ケイ素よりも良好であることを示している。この例は、良好な選択性とケイ素変換のためには第一の微粉化したケイ素のそのアルミニウム濃度において直接法反応を開始することが重要であることと、第一の微粉化したケイ素を形成するためにはアルミニウムを加えてもよいこと、を示している。
ホッパー/タンクを通じてケイ素を連続的に供給して、振動床反応器内において例1において述べた方法と同様の方法により、72時間の連続反応を行った。例3および例4共に0.12%のアルミニウムを含むC−Si(第一の微粉化したケイ素)を用いて開始した。例3では、C−Siを反応器に補充した。例4では、低AlSi(第二の微粉化したケイ素)を反応器に補充した。表4における結果は、反応開始時にC−Si(第一の微粉化したケイ素)を用いて、反応器に低AlSi(第二の微粉化したケイ素)を補充した反応では、選択性がより長く維持されていることを示している。表5は、実験終了時の床における未反応のケイ素中のアルミニウム含有量を示している。C−Siのみを用いた反応では、反応床の終了時のアルミニウム濃度が大きくなっており、そしてC−Siで開始し、反応器に低AlSiを補充した反応では、終了時のアルミニウム濃度が、C−Siを開始時に用いた場合の値である0.12%(w/w)に近かった。
ホッパー/タンクからケイ素を連続的に供給して、振動床反応器内において例1において述べたものと同様の触媒および促進剤と共に、72時間の連続反応を行った。自動モードにより、反応したケイ素を補うために反応床にホッパータンクを通じて第二の微粉化したケイ素を加えた。C−Si(第一の微粉化したケイ素)を用いて反応を開始し、C−Siと低AlSiとを重量比1:3で混合し、0.053%のアルミニウム濃度(%)を有する混合物を含む第二の微粉化したケイ素を補充した。
Claims (14)
- (i)反応器内において、銅を含む直接法触媒および促進剤の存在下、250〜350℃で、0.08〜0.25%(w/w)のアルミニウムを含む第一の微粉化したケイ素と、有機ハロゲン化物とを接触させる工程と、
(ii)前記反応器内に、未反応のケイ素およびアルミニウムの総重量に基づき、0.08〜0.2%(w/w)のアルミニウム濃度を維持するために十分な量の要求に応じた、0.001〜0.10%未満(w/w)のアルミニウムを含む第二の微粉化したケイ素を投入する工程と、
を具えるオルガノハロシランの製造方法。 - 前記方法は、式(II)で表わされるオルガノハロシランを製造する、請求項1に記載の方法。
RaHbSiX4−a−b(II)
式中、Rは、炭化水素基、Xは、ハロゲン、aは、1,2,または3であり;bは、0,1,または2であり;a+bは、1,2,または3である。 - 前記有機ハロゲン化物が、式(I)で表わされる、請求項2に記載の方法。
RX(I)
式中、Rは、炭化水素基であり、Xは、ハロゲンである。 - 前記Rが、アルキル基である、請求項3に記載の方法。
- 前記銅を含む触媒が、粒状銅粉、プレスされた銅、Cu−Zn合金、Cu−Si合金、Cu−Sb合金、酸化銅(I)、酸化銅(II)、塩化銅(II)、塩化銅(I)、窒化銅、水酸化銅、およびギ酸銅から選択される、請求項1〜4のいずれか一項に記載の方法。
- 前記触媒が、前記第一の微粉化したケイ素100重量部当たり、銅0.01〜10重量部である、請求項5に記載の方法。
- 前記第一および第二の微粉化したケイ素が、200μm以下の最大粒子直径、ならびに、1〜6μmの10パーセンタイル、5〜25μmの50パーセンタイル、および25〜60μmの90パーセンタイルによって特性化された粒径質量分布を有する、請求項1〜6のいずれか一項に記載の方法。
- 前記促進剤が、リン、リン化合物、亜鉛、亜鉛化合物、スズ、スズ化合物、アンチモン、アンチモン化合物、ヒ素、ヒ素化合物、セシウム、セシウム化合物、アルミニウムおよびアルミニウム化合物から選択される、請求項1〜7のいずれか一項に記載の方法。
- 前記反応器が、流動床反応器である、請求項1〜8のいずれか一項に記載の方法。
- 前記第二の微粉化したケイ素が、前記流動床反応器に連続的に投入される、請求項9に記載の方法。
- 前記流動床反応器の流動床が、前記有機ハロゲン化物、または前記有機ハロゲン化物および不活性ガスの混合物と共に流動化される、請求項9または10に記載の方法。
- 前記反応器内で、280〜340℃で、0.08〜0.25%(w/w)のアルミニウムを含む前記第一の微粉化したケイ素と、前記有機ハロゲン化物とを接触させる、請求項1〜11のいずれか一項に記載の方法。
- 前記第二の微粉化したケイ素は、選択性が0.20超え、またはケイ素変換が65%未満、の状態で前記オルガノハロシランが製造されるまで投入される、請求項2〜12のいずれか一項に記載の方法。
- 工程(ii)の前、間または後に、(iii)追加の第一の微粉化したケイ素を投入する工程、をさらに具える、請求項1〜13のいずれか一項に記載の方法。
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