GB981815A - A process for the exchange of silicon bound halogens - Google Patents
A process for the exchange of silicon bound halogensInfo
- Publication number
- GB981815A GB981815A GB2255961A GB2255961A GB981815A GB 981815 A GB981815 A GB 981815A GB 2255961 A GB2255961 A GB 2255961A GB 2255961 A GB2255961 A GB 2255961A GB 981815 A GB981815 A GB 981815A
- Authority
- GB
- United Kingdom
- Prior art keywords
- silicon
- halogen
- reacting
- prepared
- phenylmethyldifluorosilane
- 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
- 229910052736 halogen Inorganic materials 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 5
- 150000002367 halogens Chemical class 0.000 title abstract 3
- 229910052710 silicon Inorganic materials 0.000 title abstract 2
- 239000010703 silicon Substances 0.000 title abstract 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title 1
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 abstract 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 abstract 4
- LVTCZSBUROAWTE-UHFFFAOYSA-N diethyl(phenyl)phosphane Chemical compound CCP(CC)C1=CC=CC=C1 LVTCZSBUROAWTE-UHFFFAOYSA-N 0.000 abstract 4
- YXBGGXXOSAYEJC-UHFFFAOYSA-N difluoro-methyl-phenylsilane Chemical compound C[Si](F)(F)C1=CC=CC=C1 YXBGGXXOSAYEJC-UHFFFAOYSA-N 0.000 abstract 4
- CLZGJKHEVKJLLS-UHFFFAOYSA-N n,n-diheptylheptan-1-amine Chemical compound CCCCCCCN(CCCCCCC)CCCCCCC CLZGJKHEVKJLLS-UHFFFAOYSA-N 0.000 abstract 4
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 abstract 4
- KGWNTHHPMKEAIK-UHFFFAOYSA-N trifluoro(phenyl)silane Chemical compound F[Si](F)(F)C1=CC=CC=C1 KGWNTHHPMKEAIK-UHFFFAOYSA-N 0.000 abstract 4
- 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 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 abstract 3
- HBDHEULZOVVYQR-UHFFFAOYSA-N difluoro(methyl)silicon Chemical compound C[Si](F)F HBDHEULZOVVYQR-UHFFFAOYSA-N 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- 239000005048 methyldichlorosilane Substances 0.000 abstract 3
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 abstract 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 abstract 3
- 239000005049 silicon tetrachloride Substances 0.000 abstract 3
- VGIDEMDGGSGULM-UHFFFAOYSA-N trifluoro-(2-nitrophenyl)silane Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)[Si](F)(F)F VGIDEMDGGSGULM-UHFFFAOYSA-N 0.000 abstract 3
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- JOOMLFKONHCLCJ-UHFFFAOYSA-N N-(trimethylsilyl)diethylamine Chemical compound CCN(CC)[Si](C)(C)C JOOMLFKONHCLCJ-UHFFFAOYSA-N 0.000 abstract 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- RFXTXKQFZXCFOB-UHFFFAOYSA-N benzyl-dichloro-nitrosilane Chemical compound [N+](=O)([O-])[Si](Cl)(Cl)CC1=CC=CC=C1 RFXTXKQFZXCFOB-UHFFFAOYSA-N 0.000 abstract 2
- JWGFTXQRYGKDBB-UHFFFAOYSA-N benzyl-difluoro-nitrosilane Chemical compound [N+](=O)([O-])[Si](F)(F)CC1=CC=CC=C1 JWGFTXQRYGKDBB-UHFFFAOYSA-N 0.000 abstract 2
- GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 abstract 2
- BOMPXIHODLVNMC-UHFFFAOYSA-N difluoro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](F)(F)C1=CC=CC=C1 BOMPXIHODLVNMC-UHFFFAOYSA-N 0.000 abstract 2
- ZTBFCNHGWVPLPG-UHFFFAOYSA-N difluoro-bis(2-nitrophenyl)silane Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)[Si](F)(F)C1=C(C=CC=C1)[N+](=O)[O-] ZTBFCNHGWVPLPG-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000005054 phenyltrichlorosilane Substances 0.000 abstract 2
- 238000000746 purification Methods 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 abstract 2
- 150000004756 silanes Chemical class 0.000 abstract 2
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 abstract 2
- 239000005051 trimethylchlorosilane Substances 0.000 abstract 2
- 239000005046 Chlorosilane Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910004883 Na2SiF6 Inorganic materials 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- UWMGVIKSCFGFDR-UHFFFAOYSA-N benzyl(dibromo)silane Chemical compound Br[SiH](Br)CC1=CC=CC=C1 UWMGVIKSCFGFDR-UHFFFAOYSA-N 0.000 abstract 1
- CPNQTHWLXCQKCD-UHFFFAOYSA-N benzyl(diiodo)silane Chemical compound C1(=CC=CC=C1)C[SiH](I)I CPNQTHWLXCQKCD-UHFFFAOYSA-N 0.000 abstract 1
- LOPLNEFPHYLVIK-UHFFFAOYSA-N benzyl-difluoro-nitrosilane tetrachlorosilane Chemical compound [Si](Cl)(Cl)(Cl)Cl.[N+](=O)([O-])[Si](F)(F)CC1=CC=CC=C1 LOPLNEFPHYLVIK-UHFFFAOYSA-N 0.000 abstract 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 abstract 1
- YDJJMYQZBURFTD-UHFFFAOYSA-N chloro-fluoro-methylsilane Chemical compound C[SiH](F)Cl YDJJMYQZBURFTD-UHFFFAOYSA-N 0.000 abstract 1
- -1 chloroisobutyl compound Chemical class 0.000 abstract 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- LIQOCGKQCFXKLF-UHFFFAOYSA-N dibromo(dimethyl)silane Chemical compound C[Si](C)(Br)Br LIQOCGKQCFXKLF-UHFFFAOYSA-N 0.000 abstract 1
- DBUGVTOEUNNUHR-UHFFFAOYSA-N dibromo(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Br)(Br)C1=CC=CC=C1 DBUGVTOEUNNUHR-UHFFFAOYSA-N 0.000 abstract 1
- WUTNHXPNOOFTRW-UHFFFAOYSA-N dibromo-bis(2-nitrophenyl)silane Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)[Si](Br)(Br)C1=C(C=CC=C1)[N+](=O)[O-] WUTNHXPNOOFTRW-UHFFFAOYSA-N 0.000 abstract 1
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 abstract 1
- XNSJGJSYCNHGJU-UHFFFAOYSA-N dichloro-bis(2-nitrophenyl)silane Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)[Si](Cl)(Cl)C1=C(C=CC=C1)[N+](=O)[O-] XNSJGJSYCNHGJU-UHFFFAOYSA-N 0.000 abstract 1
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 abstract 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 abstract 1
- CTIKAHQFRQTTAY-UHFFFAOYSA-N fluoro(trimethyl)silane Chemical compound C[Si](C)(C)F CTIKAHQFRQTTAY-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000003961 organosilicon compounds Chemical class 0.000 abstract 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical class [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 abstract 1
- 150000003003 phosphines Chemical class 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229910000077 silane Inorganic materials 0.000 abstract 1
- JHGCXUUFRJCMON-UHFFFAOYSA-J silicon(4+);tetraiodide Chemical compound [Si+4].[I-].[I-].[I-].[I-] JHGCXUUFRJCMON-UHFFFAOYSA-J 0.000 abstract 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 abstract 1
- BQBMWUHVTZNUCI-UHFFFAOYSA-N trichloro-(2-nitrophenyl)silane Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)[Si](Cl)(Cl)Cl BQBMWUHVTZNUCI-UHFFFAOYSA-N 0.000 abstract 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Chemical group 0.000 abstract 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
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/125—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving both Si-C and Si-halogen linkages, the Si-C and Si-halogen linkages can be to the same or to different Si atoms, e.g. redistribution reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
A process for the redistribution of silicon-halogen bonds in organo-silicon compounds comprises forming a reaction mixture comprising at least one monomeric silane represented by the formula <FORM:0981815/C3/1> wherein R is a divalent hydrocarbon radical; Y is a hydrogen or halogen atom, or a -CN, <FORM:0981815/C3/2> or - NO2 radical; G is a monovalent hydrocarbon radical; R1 is a hydrogen atom, or a vinyl or a Y-R-radical; X is a halogen atom, e is 0, 1, 2 or 3; f is O or 1 and the sum of e and f is not greater than 3, or bistrichlorosily benzene; and a tertiary amine, a trihydrocarbyl phosphine, or a silylamine represented by the formula GmSi(NG2)4-m wherein G is a monovalent hydrocarbon radical and m is 0, 1, 2 or 3, there being present in the reaction mixture at least one silicon-fluorine bond and at least one other different silicon-halogen bond; and reacting the mixture to cause redistribution of the halogen atoms attached to silicon. Many halogen-containing silanes, tertiary amines, phosphines and silylamines are specified. The process may be performed in a batchwise or continuous manner and may be used in the preparation and/or purification of halogen-containing silanes. In examples the following compounds are prepared by the process of the invention: (1) trimethylfluorosilane from trimethylchlorosilane, phenylmethyldifluorosilane and trihexylamine; (2) nitrophenylmethyldichlorosilane from nitrophenylmethyldifluorosilane silicon tetrachloride and triheptylamine; phenyl-trichlorosilane from phenyltrifluorosilane, silicon tetrachloride and trihexylamine; (3) phenyldiethylphosphine (4) or trimethyl-N,N-diethylaminosilane (5); (6) methyldifluorosilane and methylchlorofluorosilane from phenyltrifluorosilane, methyldichlorosilane and triheptylamine; (7) bis(nitrophenyl) dichlorsilane from bis(nitrophenyl)difluorosilane, silicon tetrachloride and triheptylamine; (8) g -cyanopropylmethyldichlorosilane from g -cyanopropylmethyldifluorosilane, silicon tetrachloride, triheptylamine and trilaurylamine; (9) phenylmethyldibromosilane from phenylmethyldifluorosilane, silicon tetrabromide and phenyldiethylphosphine; (10) phenylmethyldi-iodosilane from phenylmethyldifluorosilane, silicon tetraiodide and phenyldiethylphosphine; (11) g -cyanopropylmethyldibromosilane from g - cyanopropylmethyldifluorosilane, silicon tetrabromide and 4-picoline; (12) nitrophenylmethyldichlorosilane from nitrophenylmethyldifluorosilane, phenylmethyldichlorosilane and tributylamine; (13) nitrophenyltrichlorosilane and phenyltrifluorosilane (which may be nitrated to nitrophenyltrifluorosilane and recycled) from nitrophenyltrifluorosilane, phenyltrichlorosilane and tributylamine; (14) bis(nitrophenyl)dibromosilane and diphenyldifluorosilane (which may be nitrated and recycled) from bis(nitrophenyl)difluorosilane and diphenyldibromosilane and trihexylamine; (15) g -cyanoisobutylmethyldichlorosilane and g -chloroisobutylmethyldifluorosilane (which may be reacted with NaCN and then recycled) from g -cyanoisobutylmethyldifluorosilane, g - chloroisobutylmethyldichlorosilane and tributylamine; (16) g -cyanopropylmethyldichlorosilane and methyldifluorosilane (which can be reacted with allyl cyanide and recycled) from g - cyanopropylmethyldifluorosilane, methyldichlorosilane and tributylamine. In other examples the process is used for the purification of diphenyldichlorosilane (17), trimethylchlorosilane (18), phenylmethyldichlorosilane (19), g -cyanopropylmethyldichlorosilane (20), methyldichlorosilane (21), methylvinyldichlorosilane (22), dimethyldichlorosilane (23), and dimethyldibromosilane (24). Phenylmethyldifluorosilane, phenyltrifluorosilane, diphenyldifluorosilane, and g -chloroisobutylmethyldifluorosilane are prepared in examples by reacting the appropriate chlorosilanes with Na2SiF6 in tetrahydronaphthalene. Nitrophenylmethyldifluorosilane and nitrophenyltrifluorosilane are prepared in examples by reacting the corresponding phenylsilanes in chloroform with a mixture of fuming nitric acid and concentrated sulphuric acid. g - cyanoisobutylmethyldifluorosilane is prepared in an example by reacting the chloroisobutyl compound with sodium cyanide in dimethylformamide containing potassium iodide. g - Cyanopropylmethyldifluorosilane is prepared in an example by reacting methyldifluorosilane and allyl cyanide in the presence of ethanolic chloroplatinic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2255961A GB981815A (en) | 1961-06-22 | 1961-06-22 | A process for the exchange of silicon bound halogens |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2255961A GB981815A (en) | 1961-06-22 | 1961-06-22 | A process for the exchange of silicon bound halogens |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB981815A true GB981815A (en) | 1965-01-27 |
Family
ID=10181386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2255961A Expired GB981815A (en) | 1961-06-22 | 1961-06-22 | A process for the exchange of silicon bound halogens |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB981815A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016032792A1 (en) * | 2014-08-27 | 2016-03-03 | Arkema Inc. | Fluorosilicon nitrile compounds |
-
1961
- 1961-06-22 GB GB2255961A patent/GB981815A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016032792A1 (en) * | 2014-08-27 | 2016-03-03 | Arkema Inc. | Fluorosilicon nitrile compounds |
| US10155778B2 (en) | 2014-08-27 | 2018-12-18 | Arkema Inc. | Fluorosilicon nitrile compounds |
| US20180370995A1 (en) * | 2014-08-27 | 2018-12-27 | Arkema Inc. | Fluorosilicon nitrile compounds |
| TWI665207B (en) * | 2014-08-27 | 2019-07-11 | 美商愛克瑪公司 | Fluorosilicon nitrile compounds |
| US10590149B2 (en) | 2014-08-27 | 2020-03-17 | Arkema Inc. | Fluorosilicon nitrile compounds |
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