DE913538C - Process for the production of organosilicon compounds - Google Patents
Process for the production of organosilicon compoundsInfo
- Publication number
- DE913538C DE913538C DED6292A DED0006292A DE913538C DE 913538 C DE913538 C DE 913538C DE D6292 A DED6292 A DE D6292A DE D0006292 A DED0006292 A DE D0006292A DE 913538 C DE913538 C DE 913538C
- Authority
- DE
- Germany
- Prior art keywords
- organosilicon compounds
- production
- compound
- monocyclic aryl
- alkyl
- 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
- 150000003961 organosilicon compounds Chemical class 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 229910018540 Si C Inorganic materials 0.000 claims description 11
- -1 monocyclic aryl radicals Chemical class 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000007818 Grignard reagent Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
Verfahren zur Herstellung von siliciumorganischen Verbindungen Gegenstand der Erfindung ist die Herstellung von siliciumorganischen Verbindungen, in denen die Siliciumatome durch Methylenreste miteinander verbunden sind. Diese neuen Stoffe haben die allgemeine Formel R,Y Si C H2 SiY, R, in der R gleiche oder verschiedene Alkyl- oder monocyclische Arylreste und Y Halogen oder Alkoxyreste bedeuten. R kann beispielsweise ein Alkylrest von Methyl bis Octadecyl oder ein monocyclischer Arylrest, wie Phenyl oder Tolyl, sein.Process for the preparation of organosilicon compounds of the invention is the preparation of organosilicon compounds in which the silicon atoms are linked to one another by methylene radicals. These new fabrics have the general formula R, Y Si C H2 SiY, R, in which R are the same or different Alkyl or monocyclic aryl radicals and Y are halogen or alkoxy radicals. R can for example an alkyl radical from methyl to octadecyl or a monocyclic aryl radical, such as phenyl or tolyl.
Erfindungsgemäß werden diese neuen siliciumorganischen Verbindungen dadurch gewonnen, daß man ein Alkyl- oder monocyclisches Aryl-Grignard-Reagens mit einer Verbindung der allgemeinen Formel RY2 Si C H2 SiY2 R umsetzt, wobei die Bedeutung für R und Y die gleiche wie oben ist. Gegebenenfalls kann die Umsetzung auch in Gegenwart der Verbindung C H3 C12 Si C Ha Si Cl, erfolgen.According to the invention, these new organosilicon compounds are used obtained by using an alkyl or monocyclic aryl Grignard reagent a compound of the general formula RY2 Si C H2 SiY2 R, where the meaning for R and Y is the same as above. If necessary, the implementation can also be in The presence of the compound C H3 C12 Si C Ha Si Cl take place.
Das Grignard-Reagens wird in ausreichender Menge angewandt, um in der Verbindung RY2 Si C H2 S'Y2 R ein Y durch einen Alkyl- oder einen monocyclischen Arylrest zu ersetzen. Vorzugsweise werden in diesem Falle auf z Mol Siliciumverbindung o,5 bis 1,5 Mol Grignard-Reagens verwendet.The Grignard reagent is used in an amount sufficient to replace a Y in the compound RY2 Si C H2 S'Y2 R with an alkyl or a monocyclic aryl radical. In this case, 0.5 to 1.5 moles of Grignard reagent are preferably used per mole of silicon compound.
Die Umsetzung erfolgt in der bei Grignard-Reaktionen bekannten Weise derart, daß man z. B. eine Äthylätherlösung des Grignard-Reagens mit den flüssigen Ausgangsstoffen mischt. Man kann dann durch Filtrieren und Destillation das erhaltene Produkt reinigen.The conversion takes place in the manner known from Grignard reactions such that one z. B. an ethyl ether solution of the Grignard reagent with the liquid Mixes raw materials. The obtained can then be filtered and distilled Clean product.
Die Herstellung von Verbindungen der Konstitution RY2 Si C H2 S'Y2 R ist Gegenstand des Patents 9z2 o23. Die erfindungsgemäß erhaltenen siliciumorganischen Verbindungen können als Zwischenprodukte zur Herstellung von anderen siliciumorganischen Verbindungen verwendet werden. Sie können z. B. mittels Organosiliciumverbindungen zu sogenannten Disilmethylenverbindungen umgesetzt werden, bei denen verschiedene organische Radikale an die Siliciumatome gebunden sind.The preparation of compounds of constitution RY2 Si C H2 S'Y2 R is the subject of patent 9z2 o23. The obtained according to the invention Organosilicon compounds can be used as intermediates in the manufacture of other organosilicon compounds can be used. You can e.g. B. by means of Organosilicon compounds are converted into so-called disilmethylene compounds, in which various organic radicals are bound to the silicon atoms.
Beispiel i Äquimolare Mengen von inÄther gelöstem C H3 Mg Cl und von C H3 C12 Si C H2 S' C12 C H3 werden gemischt, wobei eine Umsetzung zu der Verbindung (CH,), Cl Si C H2 Si C12 C H3 stattfindet, die durch Abfiltrieren und Destillation des Reaktionsgemisches in reinem Zustand erhalten werden kann. Die Verbindung hat bei Normaldruck einen Siedepunkt von i$6° und ein spezifisches Gewicht von i,i6o bei 25°. Beispiel 2 Ein Gemisch von 37,7 Gewichtsteilen C H3 C12 Si C H2 Si C13 und 75,4 Gewichtsteilen C H3 C12 Si C H2 S' C12 C H3 wird zu 622,4q. Gewichtsteilen in Äther gelöstem CBHs MgCI gegeben. Das Reaktionsgemisch wird nach Verdünnung mit Toluol x1(2 Stunden unter Rückfluß erhitzt. Anschließend wird filtriert und der Salzkuchen mit Toluol gewaschen.Example i Equimolar amounts of C H3 Mg Cl dissolved in ether and of C H3 C12 Si C H2 S 'C12 C H3 are mixed, resulting in a reaction to the compound (CH,), Cl Si C H2 Si C12 C H3 takes place by filtration and distillation of the reaction mixture can be obtained in a pure state. The connection has at normal pressure a boiling point of i $ 6 ° and a specific weight of i, i6o at 25 °. Example 2 A mixture of 37.7 parts by weight of C H3 C12 Si C H2 Si C13 and 75.4 parts by weight of C H3 C12 SiC H2 S 'C12 C H3 becomes 622.4q. Parts by weight given CBHs MgCl dissolved in ether. The reaction mixture is after dilution with Toluene x1 (heated under reflux for 2 hours. It is then filtered and the Salt cake washed with toluene.
Nach Entfernung des Lösungsmittels erhält man einen Rückstand, der die Verbindungen C H3 C12 Si C H2 Si ClC,H5CH3,C,H5CH,ClSiCH,SiC12C,>H5 und C H3 C12 Si C H2 Si Cl (C, H5) 2 enthält.After removing the solvent, a residue is obtained which the compounds C H3 C12 Si C H2 Si ClC, H5CH3, C, H5CH, ClSiCH, SiC12C,> H5 and C H3 Contains C12 Si C H2 Si Cl (C, H5) 2.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US913538XA | 1949-03-19 | 1949-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE913538C true DE913538C (en) | 1954-06-14 |
Family
ID=22227336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED6292A Expired DE913538C (en) | 1949-03-19 | 1950-09-29 | Process for the production of organosilicon compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE913538C (en) |
-
1950
- 1950-09-29 DE DED6292A patent/DE913538C/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2240311B2 (en) | Process for the preparation of unsaturated cycloaliphatic esters | |
| DE112011104615B4 (en) | Organoboron compound and method of making same | |
| EP0514737A1 (en) | Method for making organopolysiloxanes with at least one Si-bound cyclopentadienyl-group | |
| DE913538C (en) | Process for the production of organosilicon compounds | |
| DE60127202T2 (en) | organosilicon | |
| DE2462797B1 (en) | 2-hydroximino-1,4-oxathiacyclohexane | |
| DE1125428B (en) | Process for the preparation of 1-substituted 3-oxymethylpyrrolidines | |
| DE1301312B (en) | Process for the preparation of pyrryl (2) acetonitriles | |
| DE1097446B (en) | Process for the preparation of esters and carboxylates of alkyl boric acids | |
| DE1670478A1 (en) | Process for the preparation of derivatives of alpha-piperazino-phenylacetonitrile | |
| DE1237114B (en) | Process for the preparation of cyclopolysiloxanes | |
| DE1200318B (en) | Process for the preparation of N- (omega-aminoalkyl) -aminoalkanesulfonic acids | |
| DE930754C (en) | Process for the production of new silylphenoxy alcohols | |
| DE848825C (en) | Process for the preparation of tertiary and quaternary triamines containing ether groups | |
| DE942149C (en) | Process for the preparation of substituted glycine amides | |
| DE102009001758A1 (en) | Process for the synthesis of 1,3-bis (aminoalkyl) disiloxanes | |
| DE877306C (en) | Process for the production of organosilicon compounds | |
| DE914973C (en) | Process for the preparation of substituted threo-configured ª ‡ -halogen-ª ‰ -oxy-acylamino-ethanes | |
| DE848651C (en) | Process for the production of new, tetrafunctional organosilicon compounds | |
| DE863340C (en) | Process for the preparation of trialkylsilylphenoxysilanes | |
| DE869955C (en) | Process for the preparation of di (trialkylsilylphenoxy) dialkylsilanes | |
| AT242145B (en) | Process for the preparation of new phenthiazine compounds | |
| DE859162C (en) | Process for the production of organosilanes | |
| DE901289C (en) | Process for the production of new ketone disiloxanes | |
| DE1543995C (en) | Process for the production of 5 (3 see AminoalkyhdenH0,11 dihydro 5H dibenzo square brackets on a, square brackets on cycloheptenes |