WO2005082913A1 - Method for making alkyhalosilanes - Google Patents
Method for making alkyhalosilanes Download PDFInfo
- Publication number
- WO2005082913A1 WO2005082913A1 PCT/US2003/023920 US0323920W WO2005082913A1 WO 2005082913 A1 WO2005082913 A1 WO 2005082913A1 US 0323920 W US0323920 W US 0323920W WO 2005082913 A1 WO2005082913 A1 WO 2005082913A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- copper
- accordance
- catalyst
- reaction
- silicon
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000010949 copper Substances 0.000 claims abstract description 41
- 229910052802 copper Inorganic materials 0.000 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 30
- 239000010703 silicon Substances 0.000 claims abstract description 30
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 30
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 9
- 239000003426 co-catalyst Substances 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 38
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical class C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 claims description 26
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical group ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052718 tin Inorganic materials 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 229940050176 methyl chloride Drugs 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 4
- 229910052787 antimony Inorganic materials 0.000 claims description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 27
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 8
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 7
- 239000005048 methyldichlorosilane Substances 0.000 description 7
- 229910052786 argon Inorganic materials 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000011856 silicon-based particle Substances 0.000 description 4
- 239000004594 Masterbatch (MB) Substances 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000005055 methyl trichlorosilane Substances 0.000 description 2
- 239000011863 silicon-based powder Substances 0.000 description 2
- -1 tin halides Chemical class 0.000 description 2
- 239000011573 trace mineral Substances 0.000 description 2
- 235000013619 trace mineral Nutrition 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910000676 Si alloy Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000006011 Zinc phosphide Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- WCCJDBZJUYKDBF-UHFFFAOYSA-N copper silicon Chemical compound [Si].[Cu] WCCJDBZJUYKDBF-UHFFFAOYSA-N 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- JTBAMRDUGCDKMS-UHFFFAOYSA-N dichloro-[dichloro(methyl)silyl]-methylsilane Chemical compound C[Si](Cl)(Cl)[Si](C)(Cl)Cl JTBAMRDUGCDKMS-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 229910001120 nichrome Inorganic materials 0.000 description 1
- HOKBIQDJCNTWST-UHFFFAOYSA-N phosphanylidenezinc;zinc Chemical compound [Zn].[Zn]=P.[Zn]=P HOKBIQDJCNTWST-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229940048462 zinc phosphide Drugs 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
Definitions
- reaction is conducted in a fluid bed reactor under semi-continuous conditions.
- a semi-continuous reaction for example, the reactants are added and the reactor is run until about 50% of the silicon has been utilized. After about 50% silicon utilization, additional reactants of silicon and catalysts may be added.
- a semi-continuous reaction is in contrast to a batch mode reaction. With a batch mode reaction, all of the reactant components are combined and reacted until most of the reactants are consumed. In order to proceed, the reaction has to be stopped and additional reactants added.
- a fixed bed and stirred bed may both be run under batch conditions.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2003257058A AU2003257058A1 (en) | 2003-07-31 | 2003-07-31 | Method for making alkyhalosilanes |
EP03819319A EP1651654A1 (en) | 2003-07-31 | 2003-07-31 | Method for making alkyhalosilanes |
PCT/US2003/023920 WO2005082913A1 (en) | 2003-07-31 | 2003-07-31 | Method for making alkyhalosilanes |
CN03826862.0A CN1820014A (en) | 2003-07-31 | 2003-07-31 | Preparation of alkyhalosilanes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US2003/023920 WO2005082913A1 (en) | 2003-07-31 | 2003-07-31 | Method for making alkyhalosilanes |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005082913A1 true WO2005082913A1 (en) | 2005-09-09 |
Family
ID=34910287
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2003/023920 WO2005082913A1 (en) | 2003-07-31 | 2003-07-31 | Method for making alkyhalosilanes |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1651654A1 (en) |
CN (1) | CN1820014A (en) |
AU (1) | AU2003257058A1 (en) |
WO (1) | WO2005082913A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2826782A3 (en) * | 2008-12-23 | 2015-04-08 | Dow Corning Corporation | Processes for producing organohalohydrosilanes |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106000429B (en) * | 2016-06-15 | 2019-09-27 | 苏州铜宝锐新材料有限公司 | A kind of catalyst and its application |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4864044A (en) * | 1985-02-15 | 1989-09-05 | Union Carbide Corporation | Tin containing activated silicon for the direct reaction |
EP1055675A2 (en) * | 1999-05-27 | 2000-11-29 | General Electric Company | Method for making alkylhalosilanes |
US6288258B1 (en) * | 1999-10-25 | 2001-09-11 | Shin-Etsu Chemical Co., Ltd. | Preparation of organohalosilanes |
EP1156051A2 (en) * | 2000-05-16 | 2001-11-21 | General Electric Company | Method for promoting dialkyldihalosilane formation during direct method |
EP1184387A2 (en) * | 2000-09-05 | 2002-03-06 | General Electric Company | Method for promoting dialkyldihalosilane formation during direct method alkylhalosilane production |
US6365766B1 (en) * | 1999-04-13 | 2002-04-02 | Shin-Etsu Chemical Co., Ltd. | Metallic copper catalyst and process for the synthesis of organohalosilanes |
US20020156310A1 (en) * | 2001-02-14 | 2002-10-24 | Tetsuya Inukai | Preparation of organohalosilanes |
-
2003
- 2003-07-31 WO PCT/US2003/023920 patent/WO2005082913A1/en not_active Application Discontinuation
- 2003-07-31 CN CN03826862.0A patent/CN1820014A/en active Pending
- 2003-07-31 AU AU2003257058A patent/AU2003257058A1/en not_active Abandoned
- 2003-07-31 EP EP03819319A patent/EP1651654A1/en not_active Withdrawn
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4864044A (en) * | 1985-02-15 | 1989-09-05 | Union Carbide Corporation | Tin containing activated silicon for the direct reaction |
US6365766B1 (en) * | 1999-04-13 | 2002-04-02 | Shin-Etsu Chemical Co., Ltd. | Metallic copper catalyst and process for the synthesis of organohalosilanes |
EP1055675A2 (en) * | 1999-05-27 | 2000-11-29 | General Electric Company | Method for making alkylhalosilanes |
US6288258B1 (en) * | 1999-10-25 | 2001-09-11 | Shin-Etsu Chemical Co., Ltd. | Preparation of organohalosilanes |
EP1156051A2 (en) * | 2000-05-16 | 2001-11-21 | General Electric Company | Method for promoting dialkyldihalosilane formation during direct method |
EP1184387A2 (en) * | 2000-09-05 | 2002-03-06 | General Electric Company | Method for promoting dialkyldihalosilane formation during direct method alkylhalosilane production |
US20020156310A1 (en) * | 2001-02-14 | 2002-10-24 | Tetsuya Inukai | Preparation of organohalosilanes |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2826782A3 (en) * | 2008-12-23 | 2015-04-08 | Dow Corning Corporation | Processes for producing organohalohydrosilanes |
Also Published As
Publication number | Publication date |
---|---|
EP1651654A1 (en) | 2006-05-03 |
CN1820014A (en) | 2006-08-16 |
AU2003257058A1 (en) | 2005-09-14 |
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