JP2021528358A - 部分水素化クロロシランおよび選択的水素化によるその製造方法 - Google Patents
部分水素化クロロシランおよび選択的水素化によるその製造方法 Download PDFInfo
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- chlorosilane
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- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 title claims abstract description 79
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 239000005046 Chlorosilane Substances 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000007858 starting material Substances 0.000 claims description 24
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- -1 2,6-dimethylphenyl Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 150000004678 hydrides Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 claims description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical group CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000004821 distillation Methods 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229910008045 Si-Si Inorganic materials 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 229910006411 Si—Si Inorganic materials 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000005133 29Si NMR spectroscopy Methods 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229910010082 LiAlH Inorganic materials 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 229910003902 SiCl 4 Inorganic materials 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical class [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- FXMNVBZEWMANSQ-UHFFFAOYSA-N chloro(silyl)silane Chemical class [SiH3][SiH2]Cl FXMNVBZEWMANSQ-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- LMGZGXSXHCMSAA-UHFFFAOYSA-N cyclodecane Chemical compound C1CCCCCCCCC1 LMGZGXSXHCMSAA-UHFFFAOYSA-N 0.000 description 2
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 2
- 239000004914 cyclooctane Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 1
- CAQYAZNFWDDMIT-UHFFFAOYSA-N 1-ethoxy-2-methoxyethane Chemical compound CCOCCOC CAQYAZNFWDDMIT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- 238000004639 Schlenk technique Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- HCYGUWHMTNLDIH-UHFFFAOYSA-N bis(trichlorosilyl)silyl-trichlorosilane Chemical compound Cl[Si](Cl)(Cl)[SiH]([Si](Cl)(Cl)Cl)[Si](Cl)(Cl)Cl HCYGUWHMTNLDIH-UHFFFAOYSA-N 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- INZKMXQQBGWAOC-UHFFFAOYSA-N chloro(disilanyl)silane Chemical class [SiH3][SiH2][SiH2]Cl INZKMXQQBGWAOC-UHFFFAOYSA-N 0.000 description 1
- KQHIGRPLCKIXNJ-UHFFFAOYSA-N chloro-methyl-silylsilane Chemical compound C[SiH]([SiH3])Cl KQHIGRPLCKIXNJ-UHFFFAOYSA-N 0.000 description 1
- SLLGVCUQYRMELA-UHFFFAOYSA-N chlorosilicon Chemical compound Cl[Si] SLLGVCUQYRMELA-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229940030980 inova Drugs 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003462 sulfoxides Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- LXEXBJXDGVGRAR-UHFFFAOYSA-N trichloro(trichlorosilyl)silane Chemical compound Cl[Si](Cl)(Cl)[Si](Cl)(Cl)Cl LXEXBJXDGVGRAR-UHFFFAOYSA-N 0.000 description 1
- PZKOFHKJGUNVTM-UHFFFAOYSA-N trichloro-[dichloro(trichlorosilyl)silyl]silane Chemical compound Cl[Si](Cl)(Cl)[Si](Cl)(Cl)[Si](Cl)(Cl)Cl PZKOFHKJGUNVTM-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/08—Compounds containing halogen
- C01B33/107—Halogenated silanes
- C01B33/1071—Tetrachloride, trichlorosilane or silicochloroform, dichlorosilane, monochlorosilane or mixtures thereof
- C01B33/10715—Tetrachloride, trichlorosilane or silicochloroform, dichlorosilane, monochlorosilane or mixtures thereof prepared by reacting chlorine with silicon or a silicon-containing material
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/08—Compounds containing halogen
- C01B33/107—Halogenated silanes
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/08—Compounds containing halogen
- C01B33/107—Halogenated silanes
- C01B33/10778—Purification
-
- 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
- C07F7/0803—Compounds with Si-C or Si-Si linkages
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Silicon Compounds (AREA)
Abstract
Description
いずれの実験も、グローブボックス(M. Braun Inert Gas Systemes GmbH製)において、または標準的なシュレンク技法(D. F. Shriver, M. A. Drezdzon, The manipulation of air sensitive compounds, 1986, Wiley VCH, New York, USAの方法による)を用いて乾燥窒素の不活性雰囲気(N2、純度5.0;O2含有率<0.1ppm;H2O含有率<10ppm)下で行った。MB-SPS-800-Auto型溶媒乾燥システム(M. Braun Inert Gas Systemes GmbH製)を使用して、無水・無酸素溶媒(ジエチルエーテル、ペンタン)を準備した。Sigma-Aldrich Coorp.より重水素化ベンゼン(C6D6)を入手し、これをモレキュラーシーブに保存して、使用前に少なくとも2日間乾燥させた。
Claims (14)
- 選択的水素化による部分水素化クロロシランの製造方法であって、前記方法は、
(i)出発物質である式SinX2n+2[式中、nは、少なくとも2の整数であり、Xは、H、Cl、アルキルおよびアリールから独立して選択されるが、ただし、少なくとも2つのクロロ置換基が存在するものとする]のクロロシランを水素化剤と反応させて、部分水素化クロロシランを含む反応生成物を形成するステップであって、ここで、前記出発物質であるクロロシランと比較して、少なくとも1つのクロロ置換基がヒドリド置換基に移行するが、すべてのクロロ置換基がヒドリド置換基に移行するわけではないものとするステップと、
(ii)前記部分水素化クロロシランを前記反応生成物から分離するステップと
を含み、
前記水素化剤は、式R2AlH[式中、Rは、分岐状炭化水素または環状炭化水素である]の化合物であり、前記水素化剤は、前記出発物質であるクロロシラン中に存在する前記クロロ置換基に対して化学量論量を下回る量で存在する、方法。 - nは2〜10であり、好ましくは、nは2〜6である、請求項1記載の方法。
- Xは、HまたはClから独立して選択され、好ましくは、XはClである、請求項1または2記載の方法。
- 前記出発物質であるクロロシランが、少なくとも2つのSiCl3基を含む、請求項1から3までのいずれか1項記載の方法。
- 前記部分水素化クロロシランが、少なくとも1つのSiCl3基と少なくとも1つのSiH3基とを含む、請求項4記載の方法。
- 前記出発物質であるクロロシランが、Si(SiCl3)4、HSi(SiCl3)3、Cl3SiSiCl2SiCl3およびCl3SiSiCl3を含む群から選択される、請求項1から5までのいずれか1項記載の方法。
- Rが、イソプロピル、イソブチル、sec−ブチル、tert−ブチル、イソペンチル、2,6−ジメチルフェニル、メシチル(Mes)、2,6−ビスイソプロピルフェニル、2,4,6−トリスイソプロピルフェニル、2,4,6−トリス−tert−ブチルフェニル(Mes*)、2,4,6−トリフェニルフェニル(Trip)、2,6−Mes(C6H3)または2,6−Trip(C6H3)である、請求項1から6までのいずれか1項記載の方法。
- 前記水素化剤が、水素化ジイソブチルアルミニウムである、請求項1から7までのいずれか1項記載の方法。
- 前記反応(i)を、−70℃〜100℃の範囲、好ましくは−50℃〜80℃の範囲、最も好ましくは−30℃〜60℃の範囲の温度で、特に0℃の温度で行う、請求項1から8までのいずれか1項記載の方法。
- 前記水素化剤を、前記出発物質であるクロロシラン1モル当たり約m−kモルの量で使用し、ここで、mは、前記出発物質であるクロロシラン中のクロロ置換基の数であり、kは、前記部分水素化クロロシラン中のクロロ置換基の数である、請求項1から9までのいずれか1項記載の方法。
- 前記分離(ii)を、蒸留により、好ましくは−30℃〜100℃の範囲の温度、および0.01ミリバール〜1100ミリバールの範囲の圧力で行う、請求項1から10までのいずれか1項記載の方法。
- 前記反応(i)が、無溶媒である、請求項1から11までのいずれか1項記載の方法。
- (i)の反応時間が、0.1〜12時間、さらに好ましくは1〜8時間、特に好ましくは2〜6時間である、請求項1から12までのいずれか1項記載の方法。
- 式Cl3SiSi(SiH3)3、(Cl3Si)2Si(SiH3)2またはHSi(SiH3)2SiCl3によって表される、クロロシラン。
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EP18180840.3 | 2018-06-29 | ||
EP18180840.3A EP3587348B1 (en) | 2018-06-29 | 2018-06-29 | Partially hydrogenated chlorosilanes and methods for preparing same by selective hydrogenation |
PCT/EP2019/064918 WO2020001955A1 (en) | 2018-06-29 | 2019-06-07 | Partially hydrogenated chlorosilanes and methods for preparing same by selective hydrogenation |
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JP2021528358A true JP2021528358A (ja) | 2021-10-21 |
JP7326357B2 JP7326357B2 (ja) | 2023-08-15 |
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US (1) | US11827522B2 (ja) |
EP (1) | EP3587348B1 (ja) |
JP (1) | JP7326357B2 (ja) |
KR (1) | KR20210024605A (ja) |
CN (1) | CN112424122B (ja) |
WO (1) | WO2020001955A1 (ja) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2004036631A2 (en) * | 2002-10-18 | 2004-04-29 | Applied Materials, Inc. | Silicon-containing layer deposition with silicon compounds |
JP2020525433A (ja) * | 2017-06-29 | 2020-08-27 | ダウ シリコーンズ コーポレーション | 1,1,1−トリクロロジシランの合成 |
JP2020529957A (ja) * | 2017-07-31 | 2020-10-15 | ディーディーピー スペシャリティ エレクトロニック マテリアルズ ユーエス ナイン,エルエルシー | ペンタクロロジシランの調製方法及びそれを含む精製された反応生成物 |
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US5856548A (en) * | 1997-05-17 | 1999-01-05 | Th. Goldschmidt Ag | Process for preparing dimethylmonochlorosilane |
DE102006034061A1 (de) * | 2006-07-20 | 2008-01-24 | REV Renewable Energy Ventures, Inc., Aloha | Polysilanverarbeitung und Verwendung |
EP2076558B8 (en) * | 2006-10-24 | 2018-08-01 | Dow Silicones Corporation | Composition comprising neopentasilane and method of preparing same |
DE102009053804B3 (de) | 2009-11-18 | 2011-03-17 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Hydridosilanen |
US8575381B2 (en) | 2010-09-17 | 2013-11-05 | Gelest Technologies, Inc. | Trihydridosilyl-terminated polysilanes and methods of preparation |
DE102010063823A1 (de) * | 2010-12-22 | 2012-06-28 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Hydridosilanen |
US20190371452A1 (en) | 2016-12-02 | 2019-12-05 | Nestec S.A. | System and methods for calculating, displaying, modifying, and using improved personalized nutritional health score to assess and plan optimal diets |
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WO2004036631A2 (en) * | 2002-10-18 | 2004-04-29 | Applied Materials, Inc. | Silicon-containing layer deposition with silicon compounds |
JP2020525433A (ja) * | 2017-06-29 | 2020-08-27 | ダウ シリコーンズ コーポレーション | 1,1,1−トリクロロジシランの合成 |
JP2020529957A (ja) * | 2017-07-31 | 2020-10-15 | ディーディーピー スペシャリティ エレクトロニック マテリアルズ ユーエス ナイン,エルエルシー | ペンタクロロジシランの調製方法及びそれを含む精製された反応生成物 |
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WO2020001955A1 (en) | 2020-01-02 |
EP3587348B1 (en) | 2021-08-11 |
JP7326357B2 (ja) | 2023-08-15 |
US20210261419A1 (en) | 2021-08-26 |
EP3587348A1 (en) | 2020-01-01 |
KR20210024605A (ko) | 2021-03-05 |
CN112424122A (zh) | 2021-02-26 |
CN112424122B (zh) | 2024-02-02 |
US11827522B2 (en) | 2023-11-28 |
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