DE1157226B - Process for the preparation of organosilicon compounds - Google Patents
Process for the preparation of organosilicon compoundsInfo
- Publication number
- DE1157226B DE1157226B DEF35243A DEF0035243A DE1157226B DE 1157226 B DE1157226 B DE 1157226B DE F35243 A DEF35243 A DE F35243A DE F0035243 A DEF0035243 A DE F0035243A DE 1157226 B DE1157226 B DE 1157226B
- Authority
- DE
- Germany
- Prior art keywords
- organosilicon compounds
- preparation
- reaction
- silicon
- anhydride
- 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
- 150000003961 organosilicon compounds Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 238000005516 engineering process Methods 0.000 claims 1
- 229920001296 polysiloxane Polymers 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001816 cooling Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003377 silicon compounds Chemical class 0.000 description 2
- JOOMLFKONHCLCJ-UHFFFAOYSA-N N-(trimethylsilyl)diethylamine Chemical compound CCN(CC)[Si](C)(C)C JOOMLFKONHCLCJ-UHFFFAOYSA-N 0.000 description 1
- ZTHXGSSBOFYPTH-UHFFFAOYSA-N N-ethyl-N-methylsilylethanamine Chemical compound CCN(CC)[SiH2]C ZTHXGSSBOFYPTH-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- XIFOKLGEKUNZTI-UHFFFAOYSA-N n-[diethylamino(dimethyl)silyl]-n-ethylethanamine Chemical compound CCN(CC)[Si](C)(C)N(CC)CC XIFOKLGEKUNZTI-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007858 starting material Substances 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
- C07F7/0898—Compounds with a Si-S linkage
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4434—Amides thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4457—Compounds containing the structure C-P(=X)(X-acyl)-N, C-P(=X)(X-heteroatom)-N or C-P(=X)(X-CN)-N (X, Y = O, S)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
Description
Verfahren zur Herstellung von Organosiliciumverbindungen Es wurde gefunden, daß neue Organosiliciumverbindungen erhalten werden, wenn man Verbindungen, die mindestens eine Silicium-Stickstoff-Bindung enthalten, mit Anhydriden mehrbasiger anorganischer oder organischer Säuren umsetzt. Process for the preparation of organosilicon compounds It has been found that new organosilicon compounds are obtained when compounds which contain at least one silicon-nitrogen bond, with polybasic anhydrides converts inorganic or organic acids.
Als Ausgangsmaterialien geeignete Siliciumverbindungen sind beispielsweise: Von den flir die Umsetzung geeigneten Säureanhydriden seien die folgenden Verbindungen beispielhaft genannt: COs; P2 S5; Die Umsetzung der Komponenten verläuft im allgemeinen stark exotherm, weshalb sich meist die Verwendung inerter Verdünnungsmittel sowie Kühlung der Reaktionsmischung empfehlen.Silicon compounds suitable as starting materials are, for example: The following compounds may be mentioned as examples of the acid anhydrides suitable for the reaction: COs; P2 S5; The reaction of the components is generally highly exothermic, which is why the use of inert diluents and cooling of the reaction mixture are usually recommended.
Die Molverhältnisse, innerhalb deren die Komponenten zur Umsetzung gelangen, richten sich nach der Zahl der in der Siliciumverbindung vorhandenen Silicium-Stickstoff-Bindungen. Bei Vorhandensein mehrerer Silicium-Stickstoff-Bindungen im Molekül läßt sich die Reaktion im allgemeinen so leiten, daß diese nur teilweise oder auch stufenweise zur Umsetzung gelangen. Die Reaktion erfolgt durch Einwirkung eines Moleküls Säureanhydrid auf die Silicium-Stickstoff-Bindung und führt, wie in den folgenden Beispielen erlautert wird, zu gernischten Anhydriden der Kieselsäure bzw. ihrer Derivate und der dem anorganischen oder organischen Säureanhydrid zugrunde liegenden Säure. The molar ratios within which the components are used to implement reach depend on the number of silicon-nitrogen bonds present in the silicon compound. If several silicon-nitrogen bonds are present in the molecule, the In general, conduct the reaction in such a way that it only occurs partially or in stages get implemented. The reaction takes place through the action of a molecule of acid anhydride on the silicon-nitrogen bond and leads, as explained in the following examples becomes, to mixed anhydrides of silica or its derivatives and the dem inorganic or organic acid anhydride underlying acid.
Die Verfahrensprodukte stellen neue und definierte Organosiliciumverbindungen dar, welche in vielen Fällen destillierbar und praktisch unbegrenzt haltbar sind. Sie werden als Pflanzenschutzinittel, bevorzugt in der Landwirtschaft, Verwendung finden. The process products represent new and defined organosilicon compounds which in many cases can be distilled and have a practically unlimited shelf life. They are used as pesticides, preferably in agriculture Find.
Die folgenden Beispiele erläutern das erfindungsgemäße Verfahren: Beispiel 1 In 29 g N{-Trimethylsilyl)-diahylamin werden bei 40 bis 50"C 8,8 g CO2-Oas eingeleitet. Wegen der stark exotherm verlaufenden Reaktion wird während der Absorption des Gases mit Eis-Wasser gekühlt.The following examples explain the process according to the invention: Example 1 8.8 g of CO2-Oas are introduced into 29 g of N {-trimethylsilyl) -diahylamine at 40 to 50 ° C. Because of the strongly exothermic reaction, ice-water is used for cooling during the absorption of the gas.
Man erhält als Reaktionsprodukt 37,8 g einer farblosen Flüssigkeit, welche im Vakuum destilliert wird.The reaction product obtained is 37.8 g of a colorless liquid, which is distilled in vacuo.
Bei einem Siedepunkt von 71 bis 72"C/13 Torr erhält man 35 g (93010 der Theorie) der obigen Verbindung in Form einer farblosen Flüssigkeit mit dem -Brechungsindexn2D 1,4182 Beispiel 2 In 29 g N-(-Trimethylsilyl)-diäthylamin werden bei 30 bis 60"C 29,6 g feingepulvertes Phthalsäurv anhydrid in kleinen Portionen eingetragen. Das Anhydrid geht unter Erwärmen der Mischung in Lösung. Das Reaktionsprodukt wird im Vakuum bis zu einer Badtemperatur von 100°C erhitzt, um etwa vorhandenes, nicht umgesetztes Ngrirnethylsilyl)-diäthylamin abzudestillieren. Im Rückstand verbleiben 58,6 g (1000/o der Theorie} eines schwachrotgefärbten Öles.At a boiling point of 71 to 72 "C / 13 Torr, 35 g (93010 of theory) of the above compound are obtained in the form of a colorless liquid with the refractive index n2D 1.4182. Example 2 29.6 g of finely powdered phthalic anhydride are introduced in small portions into 29 g of N - (- trimethylsilyl) diethylamine at 30 to 60 ° C. The anhydride dissolves while the mixture is heated Heated to 100 ° C. in order to distill off any unreacted Ngr (methylsilyl) diethylamine, leaving 58.6 g (1000 / o of theory) of a pale red oil in the residue.
Beispiel 3 In eine Lösung von 29g N-(-Trimethylsilylwiäthylamin in 25 g Benzol werden bei 50"C unter Kühlung 40,5 g p-Methoxyphenyldithiophosphonsäureanhydrid eingetragen. Nachdem das gesamte Anhydrid in Lösung gegangen ist, wird das Reaktionsprodukt im Vakuum eingedampft. Im Rückstand bleiben 69 g der obigen Verbindung in Form eines klaren braunen Öles.Example 3 40.5 g of p-methoxyphenyldithiophosphonic anhydride are introduced into a solution of 29 g of N - (- trimethylsilylwiethylamine in 25 g of benzene at 50 ° C. with cooling. After all of the anhydride has dissolved, the reaction product is evaporated in vacuo g of the above compound in the form of a clear brown oil.
Beispiel 4 In eine Lösung von 20,3 g Dimethyl-bis4N,N-diäthylamino)-silan in 20 g Benzol trägt man bei 40 bis 50"C unter Außenkühlung der Mischung 14,8 g Phthalsäureanhydrid ein. Nach Beendigung der Umsetzung wird die entstandene klare Lösung noch 10 Minuten bei 80"C gerührt und dann im Vakuum eingedampft. Als Rückstand hinterbleiben 35 g der Verbindung obiger Konstitution in Form eines hellgelben Öles.Example 4 14.8 g of phthalic anhydride are introduced into a solution of 20.3 g of dimethylbis4N, N-diethylamino) silane in 20 g of benzene at 40 to 50 ° C. with external cooling of the mixture. After the reaction has ended, the resulting clear solution becomes Stirred for a further 10 minutes at 80 ° C. and then evaporated in vacuo. The residue left behind is 35 g of the compound of the above constitution in the form of a pale yellow oil.
Beispiel 5 Man leitet in 20,3 g Dimethyl-bis-(N,N-diäthylamino)-silan bei 80°C etwa 3 Stunden lang Kohlendioxyd ein. Während dieser Zeit werden etwa 8 g C aufgenommen. Anschließend destilliert man das Reaktionsgemisch im Hochvakuum und erhält 17g der Verbindung obiger Formel als farblose Flüssigkeit vom Kp.0,2 = 105 bis l070C und dem Brechungsindex n20 = 1,4370.Example 5 20.3 g of dimethyl-bis- (N, N-diethylamino) -silane are introduced into carbon dioxide at 80 ° C. for about 3 hours. During this time, about 8 g of C are absorbed. The reaction mixture is then distilled in a high vacuum and 17 g of the compound of the above formula are obtained as a colorless liquid with a boiling point of 0.2 = 105 to 1070 ° C. and a refractive index of n20 = 1.4370.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF35243A DE1157226B (en) | 1961-10-28 | 1961-10-28 | Process for the preparation of organosilicon compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF35243A DE1157226B (en) | 1961-10-28 | 1961-10-28 | Process for the preparation of organosilicon compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1157226B true DE1157226B (en) | 1963-11-14 |
Family
ID=7095921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF35243A Pending DE1157226B (en) | 1961-10-28 | 1961-10-28 | Process for the preparation of organosilicon compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1157226B (en) |
-
1961
- 1961-10-28 DE DEF35243A patent/DE1157226B/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
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