DE873085C - Process for the production of new organosilicon compounds - Google Patents
Process for the production of new organosilicon compoundsInfo
- Publication number
- DE873085C DE873085C DED8637A DED0008637A DE873085C DE 873085 C DE873085 C DE 873085C DE D8637 A DED8637 A DE D8637A DE D0008637 A DED0008637 A DE D0008637A DE 873085 C DE873085 C DE 873085C
- Authority
- DE
- Germany
- Prior art keywords
- production
- formula
- compounds
- aluminum chloride
- organosilicon compounds
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000003961 organosilicon compounds Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 18
- 239000000203 mixture Chemical group 0.000 claims description 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000007717 exclusion Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- -1 Aluminum chloride forms cyclic compounds Chemical class 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 8
- 238000009835 boiling Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000001923 cyclic compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BEFYLUYQGQYWBS-UHFFFAOYSA-N 2-benzyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C([SiH]1O[SiH2]O[SiH2]O[SiH2]O1)c1ccccc1 BEFYLUYQGQYWBS-UHFFFAOYSA-N 0.000 description 1
- 102100038916 Caspase-5 Human genes 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
- 101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000001367 organochlorosilanes Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000013638 trimer 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
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
Verfahren zur Herstellung von neuen siliciumorganischen Verbindungen Gegenstand der Erfindung ist die Herstellung von neuen siliciumorganischen Verbindungen der Formel (R2Si02AIC1)2. In der Formel bedeutet R einen Methyl-, Äthyl- oder Phenylrest bzw. ein Gemisch solcher Reste.Process for the production of new organosilicon compounds The invention relates to the production of new organosilicon compounds the formula (R2Si02AIC1) 2. In the formula, R denotes a methyl, ethyl or phenyl radical or a mixture of such residues.
Erfindungsgemäß werden diese Stoffe dadurch hergestellt, daß man vollständig kondensierte Diorganosiloxane der Formel [R,Si0],t mit Aluminiumchlorid unter weitgehendstem Ausschluß von Wasser und Feuchtigkeit umsetzt. Diese Umsetzung findet bei Temperaturen von a5' ab statt. Das Verhältnis der Reaktionsstoffe ist nicht von entscheidender Bedeutung. Um jedoch eine möglichst hohe Ausbeute zu erzielen, soll das Molarverhältnis von Siloxan zu Aluminiumchlorid innerhalb eines Bereiches von o,5: z bis 5 : i liegen.According to the invention, these substances are produced by completely condensed diorganosiloxanes of the formula [R, Si0], t with aluminum chloride under the most extensive Exclusion of water and moisture converts. This implementation takes place at temperatures from a5 'onwards. The ratio of the reactants is not critical Meaning. However, in order to achieve the highest possible yield, the molar ratio should from siloxane to aluminum chloride are within a range of 0.5: z to 5: i.
Aluminiumchlorid bildet mit vollständig kondensierten Diorganosiloxanen
cyclische Verbindungen der obigen Formel und außerdem Chlorsiloxane entsprechend
der Formel:
Als Siloxane können z. B. verwendet werden: Dimethylsüoxan, Diäthylsiloxan, Diphenylsüoxan, Phenyläthylsiloxan, Phenylmethylsiloxan, Äthylmethylsüoxan.As siloxanes, for. B. are used: Dimethylsüoxan, Diethylsiloxan, Diphenylsüoxan, Phenyläthylsiloxan, Phenylmethylsiloxan, Äthylmethylsüoxan.
Die erfindungsgemäß erhaltenen cyclischen Verbindungen sind in aromatischen Kohlenwasserstoffen lösliche kristalline, feste Stoffe. Die Alkylverbindungen sind flüchtig und können durch-Destillation und durch Umkristallisation aus Benzol gereinigt werden. Die Arylverbindungen sind nicht leicht destillierbar. Sie werden am besten durch Umkristallisieren gereinigt. Alle Verbindungen ergeben bei der Hydrolyse mit Wasser Siloxane und wasserhaltiges Aluminiumchlorid.The cyclic compounds obtained according to the invention are aromatic Crystalline, solid substances soluble in hydrocarbons. The alkyl compounds are volatile and can be purified by distillation and by recrystallization from benzene will. The aryl compounds are not easily distillable. You will be the best purified by recrystallization. All compounds result in the hydrolysis with Water siloxanes and hydrous aluminum chloride.
Die erfindungsgemäß erhaltenen cychschen Siloxan-Aluminium-Verbindungen können als Zwischenprodukte für die Herstellung von wasserabstoßenden Stoffen dienen. Sie können auch als Katalysatoren bei der Erzeugung von Organochlorsilanen Verwendung finden.The siloxane-aluminum compounds obtained according to the invention can serve as intermediate products for the manufacture of water-repellent materials. They can also be used as catalysts in the production of organochlorosilanes Find.
Beispiel i Eine Mischung von 44,85 g cyciischem trimerem Diäthylsüoxan und 19,3 g Aluminiumchlorid wird erwärmt, wobei die Reaktion sofort unter schnellem Temperaturanstieg einsetzt. Die Mischung wird zum Schluß 2 Tage auf iio bis i2o° erhitzt. Während der ganzen -Reaktion fviid atmosphärische Feuchtigkeit ferngehalten.Example i A mixture of 44.85 g of cyclic trimeric diethylsüoxane and 19.3 g of aluminum chloride is heated, causing the reaction to take place immediately with rapid Temperature rise begins. The mixture is finally heated to 10 to 10 ° for 2 days heated. Atmospheric moisture was kept away during the entire reaction.
Das Reaktionsprodukt wird destilliert. Man erhält Verbindungen der Formel Cl(C,Hb)2 S1 [O S1 (C,H5)2]"Cl , in der x i bis 4 ist und der Siedepunkt zwischen 61 und 168° bei 2 mm Druck liegt und eine Verbindung der Formel _ [(C2Hs)2 S102A1C1]2 mit einem -Siedepunkt von 184 bis igi° bei i mm Druck. Die letztere Verbindung kristallisiert beim Abkühlen. Der Aufbau dieser cyclischen Aluminiumverbindung wurde durch Chlor-, Silicium- und Aluminiumbestimmung ermittelt.The reaction product is distilled. Compounds of the formula Cl (C, Hb) 2 S1 [O S1 (C, H5) 2] "Cl, in which xi is up to 4 and the boiling point between 61 and 168 ° at 2 mm pressure, are obtained, and a compound of the formula _ [(C2Hs) 2 S102A1C1] 2 with a - boiling point of 184 to igi ° at i mm pressure. The latter compound crystallizes on cooling. The structure of this cyclic aluminum compound was determined by chlorine, silicon and aluminum determination.
Beispiel 2 38,6g cyclisches tetrameres Dimethylsüoxan und 23 g Aluminiumchlorid werden 12 Stunden auf iio bis i2o° erhitzt.Example 2 38.6 g of cyclic tetrameric dimethylsüoxane and 23 g of aluminum chloride are heated to 10 to 10 ° for 12 hours.
Das Reaktionsprodukt wird destilliert. Nach Entfernung der Chlorsiloxane der Formel (CH3)2C1Si [OSi(CH3)2]zCl , die einen Siedepunkt von 8o bis z53° bei i mm Druck haben, erhält man die Verbindung [(CH3)2 S102A1C1]2 mit einem Siedepunkt von 165 bis 167° bei 4 mm Druck. Diese Verbindung kristallisiert beim Abkühlen. Beispiel 3 Ein Gemisch von 65,1 g Phenylmethylcyclotetrasiloxan und 21,3 g Aluminiumchlorid wird . gelinde erwärmt. Die Reaktion setzt sofort ein, und die Temperatur steigt bis auf 18o°. Dann wird noch 12 Stunden auf 13o bis 14o° erhitzt. Bei der Destillation erhält man 31,7 g eines Gemisches von Verbindungen der Formel C.ICH3 (C,Hb) Si (O SiC H3 C, H5)xCl mit einem Siedepunkt von 68 bis 184° bei i mm Druck. Der Rückstand besteht aus einer viskosen Flüssigkeit der Zusammensetzung [C, HG (C H3) S102 Al C1]2 .The reaction product is distilled. After removing the chlorosiloxanes of the formula (CH3) 2C1Si [OSi (CH3) 2] zCl, which have a boiling point of 80 to z53 ° at 1 mm pressure, the compound [(CH3) 2 S102A1C1] 2 with a boiling point of 165 is obtained up to 167 ° with 4 mm pressure. This compound crystallizes on cooling. Example 3 A mixture of 65.1 g of phenylmethylcyclotetrasiloxane and 21.3 g of aluminum chloride is made. warmed up mildly. The reaction starts immediately and the temperature rises to 180 °. Then it is heated to 13o to 14o ° for a further 12 hours. The distillation gives 31.7 g of a mixture of compounds of the formula C.ICH3 (C, Hb) Si (O SiC H3 C, H5) xCl with a boiling point of 68 to 184 ° at i mm pressure. The residue consists of a viscous liquid with the composition [C, HG (C H3) S102 Al C1] 2.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US873085XA | 1950-04-17 | 1950-04-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE873085C true DE873085C (en) | 1953-04-09 |
Family
ID=22204392
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DED8637A Expired DE873085C (en) | 1950-04-17 | 1951-04-10 | Process for the production of new organosilicon compounds |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE873085C (en) |
-
1951
- 1951-04-10 DE DED8637A patent/DE873085C/en not_active Expired
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE3742069A1 (en) | METHOD FOR PRODUCING DIORGANOPOLYSILOXANS WITH TRIORGANOSILOXY GROUPS AS FINAL UNITS | |
US2658908A (en) | Production of hydrolyzable siloxanes | |
US2979519A (en) | New cyclotrisiloxanes | |
DE1131681B (en) | Process for the production of nitrogen-containing organic silicon compounds | |
DE3725377A1 (en) | METHOD FOR CONDENSING AND / OR AEQUILIBRATING ORGANO (POLY) SILOXANES | |
DE1493601C3 (en) | Process for the preparation of pentacoordinate cyclic organosilicon complex compounds | |
DE1053506B (en) | Process for the preparation of cyclic diorganopolysiloxanes | |
DE1148078B (en) | Process for the condensation of organosilicon compounds | |
DE916471C (en) | Process for the production of siloxanes | |
DE870256C (en) | Process for the production of silicon halides or of halogen-substituted monosilanes | |
DE873085C (en) | Process for the production of new organosilicon compounds | |
DE69309584T2 (en) | Alkoxysilanes with azasilacycloalkyl group and tetrametyldisiloxanes with azasilacycloalkyl group | |
US2418051A (en) | Polycyclic methylpolysiloxanes | |
DE1241827B (en) | Process for the preparation of tertiary halobutoxysilanes | |
DE3742068A1 (en) | METHOD FOR THE PRODUCTION OF DIORGANOPOLYSILOXANES ESTABLISHED IN THE ENDSTANDING UNITS OF AN SI-LINKED HYDROXYL GROUP | |
DE853350C (en) | Process for the production of polymeric organosilicon compounds in which the Si atoms are connected to one another via phenylene bridges | |
DE1047439B (en) | Process for the production of new fluorine-containing organopolysiloxanes | |
US2881197A (en) | Process of preparing alkylalkoxy disilanes | |
DE871302C (en) | Process for the production of aromatic halosilanes | |
DE1495826A1 (en) | Process for the production of terminally carbo-functional organosiloxanes | |
DE954877C (en) | Process for the preparation of organosilicon esters | |
DE954645C (en) | Process for the alkylation of organopolysiloxanes | |
DE859309C (en) | Process for the preparation of alkoxyhydrosilanes | |
DE863655C (en) | Process for the preparation of phenylchlorosilanes | |
US3390163A (en) | Octaphenyltetracyclooctasiloxanediols and methods for preparing the same |