CA1200963A - Separation of chlorosilanes - Google Patents
Separation of chlorosilanesInfo
- Publication number
- CA1200963A CA1200963A CA000431845A CA431845A CA1200963A CA 1200963 A CA1200963 A CA 1200963A CA 000431845 A CA000431845 A CA 000431845A CA 431845 A CA431845 A CA 431845A CA 1200963 A CA1200963 A CA 1200963A
- Authority
- CA
- Canada
- Prior art keywords
- mixture
- chlorosilanes
- sulfolane
- close
- boiling
- 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
Links
- 239000005046 Chlorosilane Substances 0.000 title claims abstract description 90
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 title claims abstract description 89
- 238000000926 separation method Methods 0.000 title claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 74
- 239000002904 solvent Substances 0.000 claims abstract description 72
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims abstract description 72
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 64
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 60
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 60
- 238000000034 method Methods 0.000 claims abstract description 43
- 238000009835 boiling Methods 0.000 claims abstract description 39
- 238000000605 extraction Methods 0.000 claims abstract description 27
- 239000012071 phase Substances 0.000 claims abstract description 26
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000007788 liquid Substances 0.000 claims abstract description 15
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 claims abstract description 13
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000005051 trimethylchlorosilane Substances 0.000 claims abstract description 11
- 239000005055 methyl trichlorosilane Substances 0.000 claims abstract description 10
- GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007791 liquid phase Substances 0.000 claims abstract description 8
- 239000005054 phenyltrichlorosilane Substances 0.000 claims abstract description 8
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 claims abstract description 8
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 16
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 8
- -1 aro-matic radical Chemical group 0.000 claims description 7
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 7
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000005192 partition Methods 0.000 abstract description 8
- 238000000638 solvent extraction Methods 0.000 description 8
- 238000000622 liquid--liquid extraction Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 5
- 238000004508 fractional distillation Methods 0.000 description 5
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- WBRFDUJXCLCKPX-UHFFFAOYSA-N 2,3-dimethylheptane Chemical compound CCCCC(C)C(C)C WBRFDUJXCLCKPX-UHFFFAOYSA-N 0.000 description 2
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 2
- CHBAWFGIXDBEBT-UHFFFAOYSA-N 4-methylheptane Chemical compound CCCC(C)CCC CHBAWFGIXDBEBT-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- IKMGZPRUMVFYBK-UHFFFAOYSA-N 2,2,4-trimethyloctane Chemical compound CCCCC(C)CC(C)(C)C IKMGZPRUMVFYBK-UHFFFAOYSA-N 0.000 description 1
- AUKVIBNBLXQNIZ-UHFFFAOYSA-N 2,4-dimethylheptane Chemical compound CCCC(C)CC(C)C AUKVIBNBLXQNIZ-UHFFFAOYSA-N 0.000 description 1
- OTTZHAVKAVGASB-HYXAFXHYSA-N 2-Heptene Chemical compound CCCC\C=C/C OTTZHAVKAVGASB-HYXAFXHYSA-N 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- QPILHXCDZYWYLQ-UHFFFAOYSA-N 2-nonyl-1,3-dioxolane Chemical compound CCCCCCCCCC1OCCO1 QPILHXCDZYWYLQ-UHFFFAOYSA-N 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- 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
- XMROPFQWHHUFFS-UHFFFAOYSA-N 4-ethylheptane Chemical compound CCCC(CC)CCC XMROPFQWHHUFFS-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 101000851593 Homo sapiens Separin Proteins 0.000 description 1
- 102100036750 Separin Human genes 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- KLJPJQLKSTTYTK-UHFFFAOYSA-N butyl(chloro)silane Chemical class CCCC[SiH2]Cl KLJPJQLKSTTYTK-UHFFFAOYSA-N 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- VNJCDDZVNHPVNM-UHFFFAOYSA-N chloro(ethyl)silane Chemical class CC[SiH2]Cl VNJCDDZVNHPVNM-UHFFFAOYSA-N 0.000 description 1
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical class C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 description 1
- NBWIIOQJUKRLKW-UHFFFAOYSA-N chloro(phenyl)silane Chemical class Cl[SiH2]C1=CC=CC=C1 NBWIIOQJUKRLKW-UHFFFAOYSA-N 0.000 description 1
- BGPCFXZWLWDDDU-UHFFFAOYSA-N chloro(propyl)silane Chemical class CCC[SiH2]Cl BGPCFXZWLWDDDU-UHFFFAOYSA-N 0.000 description 1
- AVDUEHWPPXIAEB-UHFFFAOYSA-N chloro-ethyl-dimethylsilane Chemical compound CC[Si](C)(C)Cl AVDUEHWPPXIAEB-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- ZXWZABFFQYQNHY-UHFFFAOYSA-N cyclohexane hexane octane Chemical compound C1CCCCC1.CCCCCCCC.CCCCCC ZXWZABFFQYQNHY-UHFFFAOYSA-N 0.000 description 1
- CRRYCJOJLZQAFR-UHFFFAOYSA-N cyclohexane;pentane Chemical compound CCCCC.C1CCCCC1 CRRYCJOJLZQAFR-UHFFFAOYSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- PNECSTWRDNQOLT-UHFFFAOYSA-N dichloro-ethyl-methylsilane Chemical compound CC[Si](C)(Cl)Cl PNECSTWRDNQOLT-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- XJRPTMORGOIMMI-UHFFFAOYSA-N ethyl 2-amino-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N)=NC=1C(F)(F)F XJRPTMORGOIMMI-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical group C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000010977 unit operation Methods 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
- C07F7/20—Purification, separation
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Silicon Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/419,855 US4402796A (en) | 1982-09-20 | 1982-09-20 | Separation of chlorosilanes by liquid extraction |
| US419,855 | 1982-09-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1200963A true CA1200963A (en) | 1986-02-25 |
Family
ID=23664037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000431845A Expired CA1200963A (en) | 1982-09-20 | 1983-07-05 | Separation of chlorosilanes |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4402796A (en]) |
| EP (1) | EP0103824B1 (en]) |
| JP (1) | JPS5976092A (en]) |
| BR (1) | BR8304993A (en]) |
| CA (1) | CA1200963A (en]) |
| DE (1) | DE3379046D1 (en]) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0335073U (en]) * | 1989-08-11 | 1991-04-05 | ||
| US5567836A (en) * | 1995-11-29 | 1996-10-22 | Dow Corning Corporation | Process for separation of methyltrichlorosilane from dimethyldichlorosilane |
| US5569775A (en) * | 1995-11-29 | 1996-10-29 | Dow Corning Corporation | Process for separation of dimethyldichlorosilane from methyltrichlorosilane |
| DE19842154C2 (de) * | 1998-09-15 | 2000-11-09 | Aventis Res & Tech Gmbh & Co | Verfahren zur Verbesserung der rektifikativen Trennung von Methyltrichlorsilan und Dimethyldichlorsilan |
| RU2166977C1 (ru) * | 1999-11-11 | 2001-05-20 | Иркутский институт химии СО РАН Некоммерческая организация научно-исследовательское учреждение | Способ разделения азеотропной смеси четыреххлористый кремний-триметилхлорсилан |
| CN100413872C (zh) * | 2005-10-31 | 2008-08-27 | 杭州师范学院 | 一种化学提纯甲基苯基二氯硅烷的方法 |
| CN101326190B (zh) * | 2005-12-06 | 2012-09-05 | 陶氏康宁公司 | 分离氯代硅烷 |
| CN100402536C (zh) * | 2006-04-24 | 2008-07-16 | 杭州师范学院 | 一种分离提纯甲基苯基二氯硅烷的化学方法 |
| CN116199708B (zh) * | 2023-03-16 | 2025-01-10 | 浙江锦华新材料股份有限公司 | 一种萃取甲基三丁酮肟基硅烷的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1054534A (en]) * | ||||
| US2388575A (en) * | 1943-06-23 | 1945-11-06 | Gen Electric | Resolution of mixtures of chlorosilanes |
| US2738359A (en) * | 1955-02-23 | 1956-03-13 | Dow Corning | Method of separating chlorosilanes |
| US3007956A (en) * | 1960-07-01 | 1961-11-07 | Gen Electric | Process for separating organosilanes |
| FR1386861A (fr) * | 1964-03-26 | 1965-01-22 | Shell Int Research | Procédé pour la séparation de mélanges de composés organiques à l'aide de sulfolane |
| US3352765A (en) * | 1964-12-21 | 1967-11-14 | Phillips Petroleum Co | Extractive distillation of sulfolane with an isoparaffing hydrocarbon entrainer |
| NL130316C (en]) * | 1965-12-09 | |||
| US4012289A (en) * | 1975-10-14 | 1977-03-15 | Phillips Petroleum Company | N-Butane/acetone separation using sulfolane |
-
1982
- 1982-09-20 US US06/419,855 patent/US4402796A/en not_active Expired - Fee Related
-
1983
- 1983-07-05 CA CA000431845A patent/CA1200963A/en not_active Expired
- 1983-09-09 DE DE8383108913T patent/DE3379046D1/de not_active Expired
- 1983-09-09 EP EP83108913A patent/EP0103824B1/en not_active Expired
- 1983-09-15 BR BR8304993A patent/BR8304993A/pt not_active IP Right Cessation
- 1983-09-19 JP JP58171401A patent/JPS5976092A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0103824A2 (en) | 1984-03-28 |
| BR8304993A (pt) | 1984-09-04 |
| EP0103824A3 (en) | 1985-11-21 |
| JPS5976092A (ja) | 1984-04-28 |
| EP0103824B1 (en) | 1989-01-25 |
| US4402796A (en) | 1983-09-06 |
| DE3379046D1 (en) | 1989-03-02 |
| JPS6225672B2 (en]) | 1987-06-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20030705 |