JP5675581B2 - 有機珪素化合物の製造方法 - Google Patents
有機珪素化合物の製造方法 Download PDFInfo
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- JP5675581B2 JP5675581B2 JP2011285141A JP2011285141A JP5675581B2 JP 5675581 B2 JP5675581 B2 JP 5675581B2 JP 2011285141 A JP2011285141 A JP 2011285141A JP 2011285141 A JP2011285141 A JP 2011285141A JP 5675581 B2 JP5675581 B2 JP 5675581B2
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- silane compound
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- 238000004519 manufacturing process Methods 0.000 title claims description 54
- 150000003961 organosilicon compounds Chemical class 0.000 title description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 57
- 238000006243 chemical reaction Methods 0.000 claims description 50
- -1 silane compound Chemical class 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 24
- 229910000077 silane Inorganic materials 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 13
- 239000011777 magnesium Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000002894 organic compounds Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 229910052749 magnesium Inorganic materials 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 230000003287 optical effect Effects 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 239000007818 Grignard reagent Substances 0.000 description 31
- 150000004795 grignard reagents Chemical class 0.000 description 31
- 239000002904 solvent Substances 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- 125000000962 organic group Chemical group 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- 150000001282 organosilanes Chemical class 0.000 description 15
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- 125000001309 chloro group Chemical group Cl* 0.000 description 10
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- 239000000126 substance Substances 0.000 description 10
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- 238000007796 conventional method Methods 0.000 description 8
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- ZSOVVFMGSCDMIF-UHFFFAOYSA-N trimethoxy(naphthalen-1-yl)silane Chemical compound C1=CC=C2C([Si](OC)(OC)OC)=CC=CC2=C1 ZSOVVFMGSCDMIF-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
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- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 6
- 239000004210 ether based solvent Substances 0.000 description 6
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- 125000000524 functional group Chemical group 0.000 description 6
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- 239000002002 slurry Substances 0.000 description 6
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- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 5
- 239000005046 Chlorosilane Substances 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
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- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 4
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- XDBGEHFHMVJRSO-UHFFFAOYSA-N magnesium;methyl hypobromite Chemical compound [Mg].COBr XDBGEHFHMVJRSO-UHFFFAOYSA-N 0.000 description 4
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- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
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- 230000005484 gravity Effects 0.000 description 3
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 239000005054 phenyltrichlorosilane Substances 0.000 description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 3
- 239000010703 silicon Chemical group 0.000 description 3
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 3
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 3
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WZHKVMLLJAPGFH-UHFFFAOYSA-M C1CCOC1.C1=CC=C2C([Mg]Br)=CC=CC2=C1 Chemical compound C1CCOC1.C1=CC=C2C([Mg]Br)=CC=CC2=C1 WZHKVMLLJAPGFH-UHFFFAOYSA-M 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- PZIIGUMPOSVMSD-UHFFFAOYSA-M [Br-].C1=CC=C2C([Mg+])=CC=CC2=C1 Chemical compound [Br-].C1=CC=C2C([Mg+])=CC=CC2=C1 PZIIGUMPOSVMSD-UHFFFAOYSA-M 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 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 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
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- PMEPWDJFSBURIP-UHFFFAOYSA-N penta-1,4-dien-3-yloxy(diphenyl)silane Chemical compound C1(=CC=CC=C1)[SiH](OC(C=C)C=C)C1=CC=CC=C1 PMEPWDJFSBURIP-UHFFFAOYSA-N 0.000 description 1
- UJAPCTHXIXTQCC-UHFFFAOYSA-N penta-1,4-dien-3-yloxy(phenyl)silane Chemical compound C1(=CC=CC=C1)[SiH2]OC(C=C)C=C UJAPCTHXIXTQCC-UHFFFAOYSA-N 0.000 description 1
- NCAIGTHBQTXTLR-UHFFFAOYSA-N phentermine hydrochloride Chemical compound [Cl-].CC(C)([NH3+])CC1=CC=CC=C1 NCAIGTHBQTXTLR-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- RKSOPLXZQNSWAS-UHFFFAOYSA-N tert-butyl bromide Chemical compound CC(C)(C)Br RKSOPLXZQNSWAS-UHFFFAOYSA-N 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- UFHILTCGAOPTOV-UHFFFAOYSA-N tetrakis(ethenyl)silane Chemical compound C=C[Si](C=C)(C=C)C=C UFHILTCGAOPTOV-UHFFFAOYSA-N 0.000 description 1
- AKRQMTFHUVDMIL-UHFFFAOYSA-N tetrakis(prop-2-enyl)silane Chemical compound C=CC[Si](CC=C)(CC=C)CC=C AKRQMTFHUVDMIL-UHFFFAOYSA-N 0.000 description 1
- DIBCUSFJCAZHKK-UHFFFAOYSA-N tetranaphthalen-1-ylsilane Chemical compound C1=CC=C2C([Si](C=3C4=CC=CC=C4C=CC=3)(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 DIBCUSFJCAZHKK-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- FCMZRNUHEXJWGB-UHFFFAOYSA-N trichloro(cyclopentyl)silane Chemical compound Cl[Si](Cl)(Cl)C1CCCC1 FCMZRNUHEXJWGB-UHFFFAOYSA-N 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- LFXJGGDONSCPOF-UHFFFAOYSA-N trichloro(hexyl)silane Chemical compound CCCCCC[Si](Cl)(Cl)Cl LFXJGGDONSCPOF-UHFFFAOYSA-N 0.000 description 1
- NDZLCUGBWLPICI-UHFFFAOYSA-N trichloro(pentan-3-yl)silane Chemical compound CCC(CC)[Si](Cl)(Cl)Cl NDZLCUGBWLPICI-UHFFFAOYSA-N 0.000 description 1
- HKFSBKQQYCMCKO-UHFFFAOYSA-N trichloro(prop-2-enyl)silane Chemical compound Cl[Si](Cl)(Cl)CC=C HKFSBKQQYCMCKO-UHFFFAOYSA-N 0.000 description 1
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 1
- DYQGNYIZMOCOFA-UHFFFAOYSA-N trichloro-(2-trichlorosilylphenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1[Si](Cl)(Cl)Cl DYQGNYIZMOCOFA-UHFFFAOYSA-N 0.000 description 1
- OOTYMVIHQSECNU-UHFFFAOYSA-N trichloro-(3-trichlorosilylphenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC([Si](Cl)(Cl)Cl)=C1 OOTYMVIHQSECNU-UHFFFAOYSA-N 0.000 description 1
- OPFQVUPHZIFJLS-UHFFFAOYSA-N trichloro-(4-trichlorosilylphenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=C([Si](Cl)(Cl)Cl)C=C1 OPFQVUPHZIFJLS-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- ZJEYUFMTCHLQQI-UHFFFAOYSA-N triethoxy(naphthalen-1-yl)silane Chemical compound C1=CC=C2C([Si](OCC)(OCC)OCC)=CC=CC2=C1 ZJEYUFMTCHLQQI-UHFFFAOYSA-N 0.000 description 1
- UYCSMKDCDZVBGS-UHFFFAOYSA-N triethoxy(naphthalen-2-yl)silane Chemical compound C1=CC=CC2=CC([Si](OCC)(OCC)OCC)=CC=C21 UYCSMKDCDZVBGS-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- KNYWDHFOQZZIDQ-UHFFFAOYSA-N trimethoxy-(2-trimethoxysilylphenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1[Si](OC)(OC)OC KNYWDHFOQZZIDQ-UHFFFAOYSA-N 0.000 description 1
- KBFAHPBJNNSTGX-UHFFFAOYSA-N trimethoxy-(3-trimethoxysilylphenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC([Si](OC)(OC)OC)=C1 KBFAHPBJNNSTGX-UHFFFAOYSA-N 0.000 description 1
- YIRZROVNUPFFNZ-UHFFFAOYSA-N trimethoxy-(4-trimethoxysilylphenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=C([Si](OC)(OC)OC)C=C1 YIRZROVNUPFFNZ-UHFFFAOYSA-N 0.000 description 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- PKRKCDBTXBGLKV-UHFFFAOYSA-N tris(ethenyl)-methylsilane Chemical compound C=C[Si](C)(C=C)C=C PKRKCDBTXBGLKV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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 System
- 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
- C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B49/00—Grignard reactions
-
- 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 System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/0827—Syntheses with formation of a Si-C bond
-
- 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 System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/122—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving the formation of Si-C linkages
Description
次いでオルガノシランと反応せしめるという方法が採用されてきた。グリニャール試薬を調製してからオルガノシシランとの反応に使用するまでの間、グリニャール試薬が失活しないように大過剰のエーテル系溶媒に希釈し、グリニャール試薬が水分と爆発的に反応することを防ぐため、グリニャール試薬の保管には不活性雰囲気下において細心の注意を払って保管する必要があった。
マイド、1−ナフチルブロマイド、2−ナフチルブロマイドo-ジブロモベンゼン、m-ジブロモベンゼン、p-ジブロモベンゼン、1,3,5-トリブロモベンゼン、1-メチル-3,5-ジブロモベンゼン。
2重量%テトラヒドロフラン溶液、2モル/リットル)の500mL (フェニルマグネシウムブロミド1.0モル相当量)を投入した。攪拌しながら60℃に加熱した後、フェニルトリメトキシシランの198.3グラム(1.0モル)を60−70℃で滴下した。滴下終了後、さらに70℃で1時間攪拌し、30℃に冷却した。生成したスラリーをアドバンテック社製ガラスろ紙GC90を用いて吸引ろ過し、副生したマグネシウムメトキシブロミドをろ別した。エバポレーターによりテトラヒドロフランを留去して、200.2グラムの生成物を得た。質量分析ガスクロマトグラフィーにより、生成物はジフェニルジメトキシシランであることが確認された(純度66.1 %)。
Claims (4)
- (A)下記一般式(1−1)で表わされる反応性シラン化合物と、
一般式(1−1):R 1 Si(OR 2 ) 3
{式中、R1は非置換のアリール基であり、R2は炭素原子数1〜6の非置換のアルキル基である}
(B)下記一般式(2)で表わされるハロゲン化有機化合物とを、
一般式(2): R3−X
(式中、R3はアリール基であり、Xはハロゲン原子である)
(C)金属マグネシウム(Mg) および (D)少なくとも1種のエーテル系化合物を含む有機溶媒の存在下で反応させる工程を含み、
前記の成分(A)、成分(C)および成分(D)を混合する工程(I)および
上記工程(I)で得た混合溶液に、前記の成分(B)を滴下して反応させる工程(II)を含む、
下記一般式(3−1)で表わされる反応性シラン化合物の製造方法。
一般式(3−1): R 1 R 3 Si(OR 2 ) 2
{式中、R1〜R3は前記同様の基である。} - 上記の工程を、単一の反応容器内で行う、請求項1に記載の反応性シラン化合物の製造方法。
- 上記の成分(D)の使用量が、一般式(3−1)で表わされる反応性シラン化合物の生成量1モルに対して0.75〜10.0モルの範囲である、請求項1または2に記載の反応性シラン化合物の製造方法。
- 光学材料用反応性シラン化合物の製造方法である、請求項1〜3のいずれかに記載の反応性シラン化合物の製造方法。
Priority Applications (6)
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JP2011285141A JP5675581B2 (ja) | 2011-12-27 | 2011-12-27 | 有機珪素化合物の製造方法 |
EP12815863.1A EP2797855B1 (en) | 2011-12-27 | 2012-12-25 | Method of producing an organic silicon compound |
US14/368,899 US9260458B2 (en) | 2011-12-27 | 2012-12-25 | Method of producing an organic silicon compound |
PCT/JP2012/084265 WO2013100166A1 (en) | 2011-12-27 | 2012-12-25 | Method of producing an organic silicon compound |
CN201710325520.3A CN106967107A (zh) | 2011-12-27 | 2012-12-25 | 生产有机硅化合物的方法 |
CN201280056754.8A CN103946185A (zh) | 2011-12-27 | 2012-12-25 | 生产有机硅化合物的方法 |
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JP2011285141A JP5675581B2 (ja) | 2011-12-27 | 2011-12-27 | 有機珪素化合物の製造方法 |
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US (1) | US9260458B2 (ja) |
EP (1) | EP2797855B1 (ja) |
JP (1) | JP5675581B2 (ja) |
CN (2) | CN106967107A (ja) |
WO (1) | WO2013100166A1 (ja) |
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CN104788488B (zh) * | 2015-03-24 | 2017-07-14 | 中国科学院化学研究所 | 一种萘基烷氧基硅烷的制备方法 |
JP6734571B2 (ja) * | 2016-05-30 | 2020-08-05 | 日産化学株式会社 | 重合性シラン化合物 |
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US2426122A (en) * | 1944-10-17 | 1947-08-19 | Montclair Res Corp | Production of organo-silicon compounds |
GB635194A (en) * | 1945-03-23 | 1950-04-05 | Arthur Harold Stevens | Improvements in or relating to organic silicon derivatives |
FR1170718A (fr) * | 1955-11-28 | 1959-01-16 | Metal & Thermit Corp | Procédé de préparation de composés organiques du silicium et produits conformes à ceux obtenus |
US4116993A (en) * | 1977-07-05 | 1978-09-26 | General Electric Company | Process for producing aromatic-containing silicone compounds |
DE3821483C2 (de) | 1988-06-25 | 1996-04-11 | Witco Gmbh | Verfahren zur Herstellung von Diorganodialkoxysilanen |
US5596120A (en) * | 1995-10-23 | 1997-01-21 | Dow Corning Corporation | Process for preparation of organosilanes |
US5629439A (en) * | 1996-03-28 | 1997-05-13 | Dow Corning Corporation | Method for preparation of allylsilanes |
US5606088A (en) * | 1996-03-28 | 1997-02-25 | Dow Corning Corporation | Process for preparation of organodisilanes |
JP2002179687A (ja) | 2000-12-18 | 2002-06-26 | Dow Corning Toray Silicone Co Ltd | オルガノアルコキシシランの製造方法 |
US6924384B2 (en) * | 2002-01-08 | 2005-08-02 | Silecs Oy | Methods and compounds for making coatings, waveguides and other optical devices |
AU2003216067A1 (en) * | 2002-01-17 | 2003-09-02 | Silecs Oy | Poly(organosiloxane) materials and methods for hybrid organic-inorganic dielectrics for integrated circuit applications |
US7084206B2 (en) | 2002-04-04 | 2006-08-01 | Dow Corning Corporation | Process for preparing phenylorganosilicon intermediates |
US6686492B2 (en) * | 2002-06-13 | 2004-02-03 | Dow Corning Corporation | Preparation of organosilicon intermediate and their derivatives in a novel grignard process |
US20100022792A1 (en) * | 2006-09-14 | 2010-01-28 | Qionghua Shen | Synthetic process for cyclic organosilanes |
FR2908412B1 (fr) * | 2006-11-10 | 2010-10-15 | Rhodia Recherches & Tech | Procede de preparation d'organomonoalcoxy (ou monohydroxy) silanes fonctionnalises, en particulier alcenyles |
FI123292B (fi) * | 2011-06-14 | 2013-01-31 | Silecs Oy | Silaanimonomeerit ja niistä saatavat korkean taitekertoimen omaavat polymeerit |
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- 2012-12-25 CN CN201280056754.8A patent/CN103946185A/zh active Pending
- 2012-12-25 WO PCT/JP2012/084265 patent/WO2013100166A1/en active Application Filing
- 2012-12-25 EP EP12815863.1A patent/EP2797855B1/en active Active
- 2012-12-25 US US14/368,899 patent/US9260458B2/en active Active
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Publication number | Publication date |
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CN106967107A (zh) | 2017-07-21 |
WO2013100166A1 (en) | 2013-07-04 |
US9260458B2 (en) | 2016-02-16 |
EP2797855B1 (en) | 2019-01-23 |
CN103946185A (zh) | 2014-07-23 |
EP2797855A1 (en) | 2014-11-05 |
US20150141689A1 (en) | 2015-05-21 |
JP2013133315A (ja) | 2013-07-08 |
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