DE3312775A1 - Verfahren zum herstellen von methylchlorsilanen - Google Patents
Verfahren zum herstellen von methylchlorsilanenInfo
- Publication number
- DE3312775A1 DE3312775A1 DE19833312775 DE3312775A DE3312775A1 DE 3312775 A1 DE3312775 A1 DE 3312775A1 DE 19833312775 DE19833312775 DE 19833312775 DE 3312775 A DE3312775 A DE 3312775A DE 3312775 A1 DE3312775 A1 DE 3312775A1
- Authority
- DE
- Germany
- Prior art keywords
- copper
- silicon
- partially oxidized
- methylchlorosilane
- formate
- 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.)
- Granted
Links
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical class C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 title claims description 45
- 238000000034 method Methods 0.000 title claims description 25
- 230000008569 process Effects 0.000 title claims description 12
- 239000010949 copper Substances 0.000 claims description 84
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 80
- 229910052802 copper Inorganic materials 0.000 claims description 79
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 47
- 229910052710 silicon Inorganic materials 0.000 claims description 44
- 239000010703 silicon Substances 0.000 claims description 43
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 40
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 26
- 229940050176 methyl chloride Drugs 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims description 13
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 230000009467 reduction Effects 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- PZPGRFITIJYNEJ-UHFFFAOYSA-N disilane Chemical compound [SiH3][SiH3] PZPGRFITIJYNEJ-UHFFFAOYSA-N 0.000 claims description 4
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002245 particle Substances 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 14
- 238000003776 cleavage reaction Methods 0.000 description 10
- 230000007017 scission Effects 0.000 description 10
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000005046 Chlorosilane Substances 0.000 description 6
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 6
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011863 silicon-based powder Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- -1 Trisilanes Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- SLLGVCUQYRMELA-UHFFFAOYSA-N chlorosilicon Chemical compound Cl[Si] SLLGVCUQYRMELA-UHFFFAOYSA-N 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000005055 methyl trichlorosilane Substances 0.000 description 3
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001348 alkyl chlorides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- TZNFGOYNQQEGJT-UHFFFAOYSA-L copper;diformate;dihydrate Chemical compound O.O.[Cu+2].[O-]C=O.[O-]C=O TZNFGOYNQQEGJT-UHFFFAOYSA-L 0.000 description 2
- KTPJDYNQZVAFBU-UHFFFAOYSA-N dichloro-[chloro(dimethyl)silyl]-methylsilane Chemical compound C[Si](C)(Cl)[Si](C)(Cl)Cl KTPJDYNQZVAFBU-UHFFFAOYSA-N 0.000 description 2
- JTBAMRDUGCDKMS-UHFFFAOYSA-N dichloro-[dichloro(methyl)silyl]-methylsilane Chemical compound C[Si](Cl)(Cl)[Si](C)(Cl)Cl JTBAMRDUGCDKMS-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000011856 silicon-based particle Substances 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 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
- 239000005749 Copper compound Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910003902 SiCl 4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- LEZFXRXSCUCNPF-UHFFFAOYSA-N chloro(methyl)silane copper Chemical compound [Cu].C[SiH2]Cl LEZFXRXSCUCNPF-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- LSIWWRSSSOYIMS-UHFFFAOYSA-L copper;diformate;tetrahydrate Chemical compound O.O.O.O.[Cu+2].[O-]C=O.[O-]C=O LSIWWRSSSOYIMS-UHFFFAOYSA-L 0.000 description 1
- 229960004643 cupric oxide Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- CIWXFRVOSDNDJZ-UHFFFAOYSA-L ferroin Chemical compound [Fe+2].[O-]S([O-])(=O)=O.C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 CIWXFRVOSDNDJZ-UHFFFAOYSA-L 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910000358 iron sulfate Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000005048 methyldichlorosilane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000009853 pyrometallurgy Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 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
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-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
- 238000004448 titration Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TXEDGTTUEVJNPE-UHFFFAOYSA-N trichloro(trimethylsilyl)silane Chemical compound C[Si](C)(C)[Si](Cl)(Cl)Cl TXEDGTTUEVJNPE-UHFFFAOYSA-N 0.000 description 1
- PVGYYKBIUKOMTG-UHFFFAOYSA-N trichloro-[chloro(dimethyl)silyl]silane Chemical compound C[Si](C)(Cl)[Si](Cl)(Cl)Cl PVGYYKBIUKOMTG-UHFFFAOYSA-N 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
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36879982A | 1982-04-16 | 1982-04-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3312775A1 true DE3312775A1 (de) | 1983-10-27 |
| DE3312775C2 DE3312775C2 (ko) | 1991-12-12 |
Family
ID=23452789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833312775 Granted DE3312775A1 (de) | 1982-04-16 | 1983-04-09 | Verfahren zum herstellen von methylchlorsilanen |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS58219187A (ko) |
| KR (1) | KR840004440A (ko) |
| AU (1) | AU1359683A (ko) |
| DE (1) | DE3312775A1 (ko) |
| FR (1) | FR2525222B1 (ko) |
| NL (1) | NL8301315A (ko) |
| NO (1) | NO831302L (ko) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3425424A1 (de) * | 1983-07-28 | 1985-02-07 | General Electric Co., Schenectady, N.Y. | Verfahren zur herstellung von alkylhalogensilanen |
| EP0620226A1 (de) * | 1993-04-16 | 1994-10-19 | Hüls Silicone Gesellschaft mit beschränkter Haftung | Verfahren zur Herstellung von Methylchlorsilanen |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2534586A1 (fr) * | 1982-10-13 | 1984-04-20 | Gen Electric | Procede de preparation selective de diorganodihalogenosilanes par rapport au monoorganotrihalogenosilanes |
| FR2552437B1 (fr) * | 1983-09-28 | 1986-09-12 | Rhone Poulenc Spec Chim | Procede et catalyseur avec le cesium comme additif pour la synthese directe du dimethyldichlorosilane |
| 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 |
| US4504597A (en) * | 1983-11-04 | 1985-03-12 | Scm Corporation | Cupreous catalyst and process making same |
| JPH01114926U (ko) * | 1988-01-28 | 1989-08-02 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1131477A (en) * | 1966-10-12 | 1968-10-23 | Midland Silicones Ltd | Preparation of alkyl halosilanes |
| DE2214611B2 (de) * | 1972-03-25 | 1979-07-05 | Bayer Ag, 5090 Leverkusen | Kupfer-Katalysator |
-
1983
- 1983-04-09 DE DE19833312775 patent/DE3312775A1/de active Granted
- 1983-04-13 JP JP58063829A patent/JPS58219187A/ja active Granted
- 1983-04-13 NO NO831302A patent/NO831302L/no unknown
- 1983-04-15 FR FR8306200A patent/FR2525222B1/fr not_active Expired
- 1983-04-15 NL NL8301315A patent/NL8301315A/nl not_active Application Discontinuation
- 1983-04-16 KR KR1019830001609A patent/KR840004440A/ko not_active Application Discontinuation
- 1983-04-18 AU AU13596/83A patent/AU1359683A/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1131477A (en) * | 1966-10-12 | 1968-10-23 | Midland Silicones Ltd | Preparation of alkyl halosilanes |
| DE2214611B2 (de) * | 1972-03-25 | 1979-07-05 | Bayer Ag, 5090 Leverkusen | Kupfer-Katalysator |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3425424A1 (de) * | 1983-07-28 | 1985-02-07 | General Electric Co., Schenectady, N.Y. | Verfahren zur herstellung von alkylhalogensilanen |
| EP0620226A1 (de) * | 1993-04-16 | 1994-10-19 | Hüls Silicone Gesellschaft mit beschränkter Haftung | Verfahren zur Herstellung von Methylchlorsilanen |
Also Published As
| Publication number | Publication date |
|---|---|
| KR840004440A (ko) | 1984-10-15 |
| AU1359683A (en) | 1983-10-20 |
| DE3312775C2 (ko) | 1991-12-12 |
| NO831302L (no) | 1983-10-17 |
| FR2525222A1 (fr) | 1983-10-21 |
| FR2525222B1 (fr) | 1986-12-05 |
| JPS6360026B2 (ko) | 1988-11-22 |
| NL8301315A (nl) | 1983-11-16 |
| JPS58219187A (ja) | 1983-12-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: SIEB, R., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 6947 LAUDENBACH |