JP4284327B2 - メチルクロロシランの製造方法 - Google Patents
メチルクロロシランの製造方法 Download PDFInfo
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- JP4284327B2 JP4284327B2 JP2006026168A JP2006026168A JP4284327B2 JP 4284327 B2 JP4284327 B2 JP 4284327B2 JP 2006026168 A JP2006026168 A JP 2006026168A JP 2006026168 A JP2006026168 A JP 2006026168A JP 4284327 B2 JP4284327 B2 JP 4284327B2
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- JP
- Japan
- Prior art keywords
- silicon
- copper
- catalyst material
- catalyst
- ppm
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical compound C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title description 27
- 239000003054 catalyst Substances 0.000 claims description 54
- 239000000463 material Substances 0.000 claims description 36
- 239000010703 silicon Substances 0.000 claims description 36
- 229910052710 silicon Inorganic materials 0.000 claims description 36
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 30
- 239000011734 sodium Substances 0.000 claims description 30
- 229910052700 potassium Inorganic materials 0.000 claims description 25
- 229910052708 sodium Inorganic materials 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 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 claims description 16
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 16
- 239000011591 potassium Substances 0.000 claims description 16
- 239000010949 copper Substances 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 14
- 229910052802 copper Inorganic materials 0.000 claims description 12
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 11
- 239000011701 zinc Substances 0.000 claims description 11
- 229910052792 caesium Inorganic materials 0.000 claims description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052725 zinc Inorganic materials 0.000 claims description 8
- 239000005751 Copper oxide Substances 0.000 claims description 6
- 229910000431 copper oxide Inorganic materials 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
- 229910052788 barium Inorganic materials 0.000 claims description 5
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 5
- 229910052718 tin Inorganic materials 0.000 claims description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 3
- 229910000881 Cu alloy Inorganic materials 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 37
- 230000015572 biosynthetic process Effects 0.000 description 12
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000007789 gas Substances 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 239000000428 dust Substances 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000002411 adverse Effects 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052701 rubidium Inorganic materials 0.000 description 3
- 229910052712 strontium Inorganic materials 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000011856 silicon-based particle Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical class C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 239000011863 silicon-based powder Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000011787 zinc oxide 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
- C07F7/12—Organo silicon halides
- C07F7/16—Preparation thereof from silicon and halogenated hydrocarbons direct synthesis
-
- A—HUMAN NECESSITIES
- A44—HABERDASHERY; JEWELLERY
- A44B—BUTTONS, PINS, BUCKLES, SLIDE FASTENERS, OR THE LIKE
- A44B17/00—Press-button or snap fasteners
- A44B17/0005—Fastening of press-button fasteners
-
- A—HUMAN NECESSITIES
- A44—HABERDASHERY; JEWELLERY
- A44D—INDEXING SCHEME RELATING TO BUTTONS, PINS, BUCKLES OR SLIDE FASTENERS, AND TO JEWELLERY, BRACELETS OR OTHER PERSONAL ADORNMENTS
- A44D2201/00—Fastening by snap action
- A44D2201/50—Button-type snap fasteners
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
a)全ての量は質量に対するものである;
b)全ての圧力は0.10MPa(絶対圧)である;
c)全ての温度は20℃である。
加熱コイル/ガス整流フリット(Gasverteilerfritte)、ブライン循環式冷却を備えた蒸留ブリッジ、及び受容フラスコを有する研究室流動床反応器(内径25mmと高さ500mmを有する鉛直ガラス管)。
銅触媒、助触媒としての0.8gの金属亜鉛、8mgのスズ粉末及び場合によりNaCl及びKClを均質混和し、120gのケイ素と混合し、反応器中に充填し、そして40l/hの窒素流で340℃において加熱する。引き続き40l/hのクロロメタンを反応器に導通させ、そして触媒材料を395℃に加熱する。2〜30分の範囲の誘導時間後にシラン生成が始まり、反応温度を360℃に下げ、そして50mlのメチルクロロシランが回収される(開始段階)。引き続き更に30mlのメチルクロロシランが回収される。この30mlのシラン生成のための時間を製造段階と呼び、その生成率(PR2)は式
同等のCu触媒の場合に、触媒材料中での少なすぎるNa量と高すぎるNa量とは比ジメチルジクロロシラン生成に悪影響を及ぼすことが示される。使用されるケイ素は以下の組成を有した:0.24%のAl、0.039%のCa、0.44%のFe、0.046%のTi、<10ppmの各個々の元素Na、K、Cs、Sr、Ba。
同等のCu触媒の場合に、触媒材料中での少なすぎるK量と高すぎるK量とは比ジメチルジクロロシラン生成に悪影響を及ぼすことが示される。使用されるケイ素は以下の組成を有した:0.21%のAl、0.039%のCa、0.32%のFe、0.032%のTi、<10ppmの各個々の元素Na、K、Cs、Sr、Ba。
同等のCu触媒の場合に、触媒材料中での少なすぎるNa及びKの量と高すぎるNa及びKの量とは比ジメチルジクロロシラン生成に悪影響を及ぼすことが示される。
ミュラー・ロッショーによるメチルクロロシランの製造のための装置であって、連続的な触媒材料供給、サイクロンシステム、ダスト排出システム並びに循環ガス返送を介した触媒材料返送を伴う流動床反応器からなる、例えば“Catalyzed Direct Reactions of Silicon; K.M. Lewis, D.G. Rethwisch; Eisevier 1993”の第8〜21頁に記載されている工業用装置において、同等の条件下に、触媒材料中26ppmのNa濃度と40ppmのK濃度で、触媒系としてCuCl/CuO混合物を使用した。促進剤としてSnを使用した。Zn助触媒を変更するが、その際、触媒材料中のZnの絶対濃度は一定に保持した。
Claims (8)
- クロロメタンを、ケイ素、銅触媒を含有し、かつナトリウムとカリウムの全割合が10〜400ppmを有する触媒材料と反応させることによってメチルクロロシランを直接合成するための方法。
- カリウムの含有率がナトリウムより高い、請求項1記載の方法。
- 銅の形態が、金属銅、銅合金、酸化銅及び塩化銅から選択される、請求項1又は2記載の方法。
- リン、セシウム、バリウム、スズ及びアンチモンから選択される促進剤を使用する、請求項1から3までのいずれか1項記載の方法。
- 亜鉛を助触媒として使用する、請求項1から4までのいずれか1項記載の方法。
- 亜鉛をZnCl2の形で使用する、請求項5記載の方法。
- 触媒材料中の亜鉛の量が、元素に対して、0.01〜0.5質量%である、請求項5又は6記載の方法。
- 付加的な促進剤としてスズが存在する、請求項4から7までのいずれか1項記載の方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102005005052A DE102005005052A1 (de) | 2005-02-03 | 2005-02-03 | Verfahren zur Herstellung von Methylchlorsilanen |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006213714A JP2006213714A (ja) | 2006-08-17 |
JP4284327B2 true JP4284327B2 (ja) | 2009-06-24 |
Family
ID=35950438
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006026168A Expired - Fee Related JP4284327B2 (ja) | 2005-02-03 | 2006-02-02 | メチルクロロシランの製造方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US7153992B2 (ja) |
EP (1) | EP1707569B1 (ja) |
JP (1) | JP4284327B2 (ja) |
KR (1) | KR100731205B1 (ja) |
CN (1) | CN100383146C (ja) |
DE (2) | DE102005005052A1 (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101417923B (zh) * | 2008-12-01 | 2011-08-17 | 山东东岳有机硅材料有限公司 | 一种氯甲烷回收精制的方法 |
CN102728368B (zh) * | 2012-06-18 | 2015-05-20 | 中国科学院过程工程研究所 | 一种有机硅单体合成用黄铜复合粉助催化剂及其制备方法 |
CN106000429B (zh) * | 2016-06-15 | 2019-09-27 | 苏州铜宝锐新材料有限公司 | 一种催化剂及其应用 |
CN109851628B (zh) * | 2018-12-18 | 2021-07-23 | 万华化学集团股份有限公司 | 一种苯基氯硅烷的制备方法 |
CN109821482A (zh) * | 2019-03-28 | 2019-05-31 | 合盛硅业股份有限公司 | 催化剂自动连续添加方法及装置 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2552438B1 (fr) * | 1983-09-28 | 1985-11-08 | Rhone Poulenc Spec Chim | Procede et catalyseur avec un alcalin comme additif pour la synthese directe du dimethyldichlorosilane |
DE3841417A1 (de) | 1988-12-08 | 1990-06-13 | Bayer Ag | Verfahren zur herstellung von organosilanen |
FR2665446B1 (fr) * | 1990-07-31 | 1992-11-27 | Rhone Poulenc Chimie | Procede et catalyseur comprenant un compose de lanthanide comme additif promoteur pour la synthese directe du dimethyldichlorosilane. |
DE4142432A1 (de) * | 1991-12-20 | 1993-06-24 | Wacker Chemie Gmbh | Verfahren zur herstellung von kupferpulver |
AU669255B2 (en) * | 1993-03-24 | 1996-05-30 | Ge Bayer Silicones Gmbh & Co. Kg | Process for the preparation of organochlorosilanes |
DE4342910A1 (de) * | 1993-03-24 | 1994-09-29 | Bayer Ag | Verfahren zur Herstellung von Organochlorsilanen |
EP0893448B1 (en) * | 1997-06-27 | 2003-04-16 | Shin-Etsu Chemical Co., Ltd. | Preparation of alkylhalosilanes |
FR2848124B1 (fr) | 2002-12-09 | 2006-03-10 | Rhodia Chimie Sa | Utilisation d'une composition comprenant cuivre, metal alcalin et phosphore comme systeme catalytique pour conduire la synthese directe d'alkylhalogenosilanes en attenuant la formation de coke |
FR2861728B1 (fr) * | 2003-11-05 | 2005-12-30 | Rhodia Chimie Sa | Procede de synthese directe d'alkylhalogenosilanes |
-
2005
- 2005-02-03 DE DE102005005052A patent/DE102005005052A1/de not_active Withdrawn
-
2006
- 2006-01-19 DE DE502006008973T patent/DE502006008973D1/de active Active
- 2006-01-19 EP EP06001114A patent/EP1707569B1/de not_active Not-in-force
- 2006-01-27 US US11/341,094 patent/US7153992B2/en not_active Expired - Fee Related
- 2006-02-02 KR KR1020060010060A patent/KR100731205B1/ko not_active IP Right Cessation
- 2006-02-02 JP JP2006026168A patent/JP4284327B2/ja not_active Expired - Fee Related
- 2006-02-05 CN CNB2006100067810A patent/CN100383146C/zh not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US20060173203A1 (en) | 2006-08-03 |
CN1814603A (zh) | 2006-08-09 |
KR20060089151A (ko) | 2006-08-08 |
US7153992B2 (en) | 2006-12-26 |
DE502006008973D1 (de) | 2011-04-14 |
EP1707569A1 (de) | 2006-10-04 |
DE102005005052A1 (de) | 2006-08-10 |
KR100731205B1 (ko) | 2007-06-22 |
JP2006213714A (ja) | 2006-08-17 |
EP1707569B1 (de) | 2011-03-02 |
CN100383146C (zh) | 2008-04-23 |
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