DE1077216B - Verfahren zur Herstellung von Chlorphenylchlorsilanen - Google Patents
Verfahren zur Herstellung von ChlorphenylchlorsilanenInfo
- Publication number
- DE1077216B DE1077216B DEG25069A DEG0025069A DE1077216B DE 1077216 B DE1077216 B DE 1077216B DE G25069 A DEG25069 A DE G25069A DE G0025069 A DEG0025069 A DE G0025069A DE 1077216 B DE1077216 B DE 1077216B
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- antimony
- chlorination
- ferric chloride
- reaction
- 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.)
- Pending
Links
- VIRVTHOOZABTPR-UHFFFAOYSA-N dichloro(phenyl)silane Chemical class Cl[SiH](Cl)C1=CC=CC=C1 VIRVTHOOZABTPR-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 11
- 239000000460 chlorine Substances 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- 238000005660 chlorination reaction Methods 0.000 claims description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 20
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 19
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- GTPDFCLBTFKHNH-UHFFFAOYSA-N chloro(phenyl)silicon Chemical compound Cl[Si]C1=CC=CC=C1 GTPDFCLBTFKHNH-UHFFFAOYSA-N 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 229910052787 antimony Inorganic materials 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
- 150000001463 antimony compounds Chemical class 0.000 claims description 3
- 229910003902 SiCl 4 Inorganic materials 0.000 claims description 2
- 150000002506 iron compounds Chemical class 0.000 claims description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- NBWIIOQJUKRLKW-UHFFFAOYSA-N chloro(phenyl)silane Chemical class Cl[SiH2]C1=CC=CC=C1 NBWIIOQJUKRLKW-UHFFFAOYSA-N 0.000 description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000005054 phenyltrichlorosilane Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- FFZNQXSOIIVDRB-UHFFFAOYSA-N trichloro-(2,3,4,5-tetrachlorophenyl)silane Chemical compound ClC1=CC([Si](Cl)(Cl)Cl)=C(Cl)C(Cl)=C1Cl FFZNQXSOIIVDRB-UHFFFAOYSA-N 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- -1 cup trichloride Chemical compound 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical class C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 241001486234 Sciota Species 0.000 description 1
- USYLIGCRWXYYPZ-UHFFFAOYSA-N [Cl].[Fe] Chemical compound [Cl].[Fe] USYLIGCRWXYYPZ-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 150000004951 benzene Polymers 0.000 description 1
- 150000001555 benzenes Polymers 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical compound [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- ZGAFXPZULJFSLW-UHFFFAOYSA-N dichloro-(2,3,4,5,6-pentachlorophenyl)-phenylsilane Chemical compound ClC1=C(C(=C(C(=C1[Si](Cl)(Cl)C1=CC=CC=C1)Cl)Cl)Cl)Cl ZGAFXPZULJFSLW-UHFFFAOYSA-N 0.000 description 1
- WFWGRXVWWWTPAA-UHFFFAOYSA-N dichloro-(2,3-dichlorophenyl)-phenylsilane Chemical compound ClC1=CC=CC([Si](Cl)(Cl)C=2C=CC=CC=2)=C1Cl WFWGRXVWWWTPAA-UHFFFAOYSA-N 0.000 description 1
- QCEREOYAKDAJBV-UHFFFAOYSA-N dichloro-phenyl-(2,3,4,5-tetrachlorophenyl)silane Chemical compound ClC=1C(=C(C(=C(C=1)[Si](Cl)(Cl)C1=CC=CC=C1)Cl)Cl)Cl QCEREOYAKDAJBV-UHFFFAOYSA-N 0.000 description 1
- BFARDKHCCZOCAX-UHFFFAOYSA-N dichloro-phenyl-(2,3,4-trichlorophenyl)silane Chemical compound ClC1=C(C(=C(C=C1)[Si](Cl)(Cl)C1=CC=CC=C1)Cl)Cl BFARDKHCCZOCAX-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960004887 ferric hydroxide Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- IEECXTSVVFWGSE-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Fe+3] IEECXTSVVFWGSE-UHFFFAOYSA-M 0.000 description 1
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 description 1
- KNMWLFKLSYMSBR-UHFFFAOYSA-N iron;octanoic acid Chemical compound [Fe].CCCCCCCC(O)=O KNMWLFKLSYMSBR-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- LIYKJALVRPGQTR-UHFFFAOYSA-M oxostibanylium;chloride Chemical compound [Cl-].[Sb+]=O LIYKJALVRPGQTR-UHFFFAOYSA-M 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G4/00—Fixed capacitors; Processes of their manufacture
- H01G4/002—Details
- H01G4/018—Dielectrics
- H01G4/20—Dielectrics using combinations of dielectrics from more than one of groups H01G4/02 - H01G4/06
- H01G4/22—Dielectrics using combinations of dielectrics from more than one of groups H01G4/02 - H01G4/06 impregnated
- H01G4/221—Dielectrics using combinations of dielectrics from more than one of groups H01G4/02 - H01G4/06 impregnated characterised by the composition of the impregnant
- H01G4/222—Dielectrics using combinations of dielectrics from more than one of groups H01G4/02 - H01G4/06 impregnated characterised by the composition of the impregnant halogenated
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
-
- 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
- C07F7/127—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions not affecting the linkages to the silicon atom
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/46—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes silicones
- H01B3/465—Silicone oils
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US679064A US2887503A (en) | 1957-08-19 | 1957-08-19 | Method for preparing chlorophenylchlorosilanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1077216B true DE1077216B (de) | 1960-03-10 |
Family
ID=24725434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG25069A Pending DE1077216B (de) | 1957-08-19 | 1958-08-08 | Verfahren zur Herstellung von Chlorphenylchlorsilanen |
Country Status (5)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL286871A (US06252093-20010626-C00008.png) * | 1961-12-18 | |||
| CN102633827B (zh) * | 2012-04-26 | 2015-01-07 | 江苏大学 | 离子液体催化制备多氯代苯基三氯硅烷的方法 |
| CN104004011A (zh) * | 2014-05-16 | 2014-08-27 | 江苏大学 | 一种二苯基二氯硅烷氯化的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1137470A (fr) * | 1954-08-18 | 1957-05-29 | Thomson Houston Comp Francaise | Procédé de préparation des chlorophenylchlorosiloxanes |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2258219A (en) * | 1939-09-27 | 1941-10-07 | Gen Electric | Halogenated aryl silicones |
| US2887604A (en) * | 1955-06-27 | 1959-05-19 | Bodine | Spark discharge sound generator |
-
0
- BE BE570423D patent/BE570423A/xx unknown
-
1957
- 1957-08-19 US US679064A patent/US2887503A/en not_active Expired - Lifetime
-
1958
- 1958-07-24 GB GB23857/58A patent/GB845815A/en not_active Expired
- 1958-08-08 DE DEG25069A patent/DE1077216B/de active Pending
- 1958-08-19 FR FR1211556D patent/FR1211556A/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1137470A (fr) * | 1954-08-18 | 1957-05-29 | Thomson Houston Comp Francaise | Procédé de préparation des chlorophenylchlorosiloxanes |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1211556A (fr) | 1960-03-17 |
| BE570423A (US06252093-20010626-C00008.png) | |
| GB845815A (en) | 1960-08-24 |
| US2887503A (en) | 1959-05-19 |
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