DE888852C - Process for the preparation of organohalosilanes - Google Patents
Process for the preparation of organohalosilanesInfo
- Publication number
- DE888852C DE888852C DEF1662A DEF0001662A DE888852C DE 888852 C DE888852 C DE 888852C DE F1662 A DEF1662 A DE F1662A DE F0001662 A DEF0001662 A DE F0001662A DE 888852 C DE888852 C DE 888852C
- Authority
- DE
- Germany
- Prior art keywords
- organohalosilanes
- alkyl
- preparation
- mixed
- aryl
- 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
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- -1 aryl aluminum halides Chemical class 0.000 claims description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical class C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- YSTQWZZQKCCBAY-UHFFFAOYSA-L methylaluminum(2+);dichloride Chemical compound C[Al](Cl)Cl YSTQWZZQKCCBAY-UHFFFAOYSA-L 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/122—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving the formation of Si-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Description
Verfahren zur Herstellung von Organohalogensilanen Die vorliegende Erfindung betrifft ein neues Verfahren zur Herstellung von Alkyl- bzw. Arylhalogensilanen. Es besteht darin, daß Siliciumtetrahalogenide im Gemisch mit Alkyl- bzw. Arylaluminiumhalogeniden bei erhöhten Temperaturen umgesetzt werden.Process for the preparation of organohalosilanes The present The invention relates to a new process for the preparation of alkyl- or arylhalosilanes. It consists in the fact that silicon tetrahalides are mixed with alkyl or aryl aluminum halides be implemented at elevated temperatures.
Als Siliciumtetrahalogenidkomponente kann beispielsweise das technisch leicht und billig zugängliche Siliciumtetrachlorid verwendet werden, das z. B. mit Dimethylaluminiuinchlorid gemischt umgesetzt wird.As a silicon tetrahalide component, for example, can be used technically easily and cheaply accessible silicon tetrachloride can be used, the z. B. with Dimethylaluminiuinchlorid is reacted mixed.
Bei der Siedetemperatur des Gemisches verläuft die Umsetzung nicht oder jedenfalls nur sehr träge. Sie wird erheblich beschleunigt, wenn die Mischung, zweckmäßig im geschlossenen Gefäß unter eigenem Dampfdruck, auf Temperaturen von etwa 25o bis etwa q00° erhitzt wird. Dabei spielen sich z. B. folgende Reaktionen ab: Al (CHg)2C1 ' Si Cl, = (CH3)ZSiC12 -1- Al Cl, Al (C H3)"Cl + 2 S'CI4 = 2 (C H3) Si Cl, -f- A1 C13. In formaler Hinsicht ist die Alkyl- bzw. Arylaluminiumhalogenverbindung R,AIX oder RAIX, einer Grignardverbindung RMgX sowohl hinsichtlich Aufbau wie Wirkungsweise ähnlich. Sie unterscheidet sich aber hinsichtlich der Wirkungsweise vorteilhaft von dieser insofern, als sie nicht wie die Magnesiumverbindung die Anwesenheit eines bestimmten Lösungsmittels, insbesondere Äther, erfordert, um ihre Wirksamkeit entfalten zu können, zum anderen dadurch, daß sie als Nebenprodukt eine technisch nutzbare Verbindung, das Aluminiumchlorid, liefert, das durch Sublimation zudem leicht gereinigt werden kann.At the boiling point of the mixture, the reaction does not proceed, or at least only very slowly. It is considerably accelerated if the mixture is heated to temperatures of about 25o to about q00 °, expediently in a closed vessel under its own steam pressure. This z. B. the following reactions: Al (CHg) 2C1 'Si Cl, = (CH3) ZSiC12 -1- Al Cl, Al (C H3) "Cl + 2 S'CI4 = 2 (C H3) Si Cl, -f- A1 C13. Formally, the alkyl or arylaluminum halogen compound R, AIX or RAIX is similar to a Grignard compound RMgX both in terms of structure and mode of action Certain solvents, in particular ether, are required in order to be able to develop their effectiveness, on the other hand because they provide a technically useful compound, aluminum chloride, as a by-product, which can also be easily purified by sublimation.
Die Durchführbarkeit der erfindungsgemäßen Umsetzung war um so überraschender und um so weniger vorauszusehen, als aus der Literatur bekannt ist, daß beim Überleiten der Dämpfe von Siliciumtetrahalogeniden zusammen mit Alkyl- bzw. Arylhalogeniden über auf etwa 3oo bis 5oo° erhitztes Aluminium oder Zink keine oder nur eine ganz geringfügige Bildung von Alkyl- bzw. Arylhalogensilanen stattfindet.The feasibility of the implementation according to the invention was all the more surprising and all the less to foresee as it is known from the literature that when passing over the vapors of silicon tetrahalides together with alkyl or aryl halides about aluminum heated to about 3oo to 5oo ° or Zinc none or only a very slight formation of alkyl or aryl halosilanes takes place.
Beispiel Eine Mischung von Dimethylaluminiumchloriden, bestehend aus 35 Gewichtsprozent CH,AIC12 und 65 .Gewichtsprozent (C H3) 2 A1 Cl, und Si C14 im Gewichtsverhältnis z : 2 wird im Autoklav 6 Stunden auf 300° erhitzt. Nach dem Erkalten wird die Flüssigkeit von der ausgeschiedenen Festsubstanz getrennt und rektifiziert. Es ergibt sich, daß die flüssige Phase aus 34,8 °/o unverändertem Si Cl, 8,3 °/o (C H3)2SiC12, 28,o °% CH3SiC13 und 28,8 °/o Rückstand besteht, der gelöstesAluminiumchlorid und unverbrauchtes Methylaluminiumchlorid darstellt.Example A mixture of dimethylaluminum chlorides, consisting of 35 percent by weight CH, AIC12 and 65 percent by weight (C H3) 2 A1 Cl, and Si C14 in a weight ratio of z: 2 is heated to 300 ° in the autoclave for 6 hours. After cooling, the liquid is separated from the excreted solid matter and rectified. It turns out that the liquid phase consists of 34.8 % unchanged Si Cl, 8.3% (C H3) 2SiC12, 28.0% CH3SiC13 and 28.8% residue, the dissolved aluminum chloride and represents unused methyl aluminum chloride.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF1662A DE888852C (en) | 1950-06-09 | 1950-06-10 | Process for the preparation of organohalosilanes |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE689436X | 1950-06-09 | ||
| DEF1662A DE888852C (en) | 1950-06-09 | 1950-06-10 | Process for the preparation of organohalosilanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE888852C true DE888852C (en) | 1953-09-07 |
Family
ID=25946276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF1662A Expired DE888852C (en) | 1950-06-09 | 1950-06-10 | Process for the preparation of organohalosilanes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE888852C (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1038553B (en) * | 1954-11-12 | 1958-09-11 | Kali Chemie Ag | Process for the production of silicon compounds which contain at least one hydrogen atom on silicon |
| US2853504A (en) * | 1955-05-05 | 1958-09-23 | Kali Chemie Ag | Alkylation of organopolysiloxanes using a hydrocarbon aluminum compound |
| US2857414A (en) * | 1954-09-18 | 1958-10-21 | Kali Chemie Ag | Preparation of partially substittuted silanes and silane |
| DE972855C (en) * | 1953-06-11 | 1959-10-15 | Kali Chemie Ag | Process for the preparation of monomeric organosilicon compounds |
| US2914549A (en) * | 1956-09-28 | 1959-11-24 | Ici Ltd | Production of alkyl halosilanes by reacting silica with alkyl aluminum halides |
| US2945874A (en) * | 1956-08-28 | 1960-07-19 | Kali Chemie Ag | Alkylation of chlorinated silanes |
| DE974338C (en) * | 1953-06-12 | 1960-12-01 | Kali Chemie Ag | Process for the preparation of monomeric organosilicon compounds |
| US3103526A (en) * | 1963-09-10 | Preparation of alkyl compounds of |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2403370A (en) * | 1945-03-15 | 1946-07-02 | Gen Electric | Alkylation of halogenosilanes |
-
1950
- 1950-06-10 DE DEF1662A patent/DE888852C/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2403370A (en) * | 1945-03-15 | 1946-07-02 | Gen Electric | Alkylation of halogenosilanes |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3103526A (en) * | 1963-09-10 | Preparation of alkyl compounds of | ||
| DE972855C (en) * | 1953-06-11 | 1959-10-15 | Kali Chemie Ag | Process for the preparation of monomeric organosilicon compounds |
| DE974338C (en) * | 1953-06-12 | 1960-12-01 | Kali Chemie Ag | Process for the preparation of monomeric organosilicon compounds |
| US2857414A (en) * | 1954-09-18 | 1958-10-21 | Kali Chemie Ag | Preparation of partially substittuted silanes and silane |
| DE1038553B (en) * | 1954-11-12 | 1958-09-11 | Kali Chemie Ag | Process for the production of silicon compounds which contain at least one hydrogen atom on silicon |
| US2853504A (en) * | 1955-05-05 | 1958-09-23 | Kali Chemie Ag | Alkylation of organopolysiloxanes using a hydrocarbon aluminum compound |
| US2945874A (en) * | 1956-08-28 | 1960-07-19 | Kali Chemie Ag | Alkylation of chlorinated silanes |
| US2914549A (en) * | 1956-09-28 | 1959-11-24 | Ici Ltd | Production of alkyl halosilanes by reacting silica with alkyl aluminum halides |
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