DES0031521MA - - Google Patents
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- Publication number
- DES0031521MA DES0031521MA DES0031521MA DE S0031521M A DES0031521M A DE S0031521MA DE S0031521M A DES0031521M A DE S0031521MA
- Authority
- DE
- Germany
- Prior art keywords
- silicon
- acid esters
- silicic acid
- ether
- reacted
- 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.)
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 150000004756 silanes Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 5
- 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 4
- 239000003921 oil Substances 0.000 description 4
- 239000005049 silicon tetrachloride Substances 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- -1 cresyl orthosilicate Chemical compound 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical compound CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052605 nesosilicate Inorganic materials 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
Description
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
Tag der Anmeldung: 16. Dezember 1952 Bekanintgemacht am 24. Mai 1956Registration date: December 16, 1952 Bekanint made May 24, 1956
DEUTSCHES PATENTAMTGERMAN PATENT OFFICE
<!■<! ■
KLASSE 12g GRUPPE S 31521 IVbI 12 q CLASS 12g GROUP S 31521 IVbI 12 q
sind als Erfinder genannt wordenhave been named as inventors
Die Erfindung eröffnet für die Herstellung von Kieselsäureestern alkylierter Phenole einen neuen Weg. Während man bisher alkylierte aromatische Oxyverbindungen mit Siliciumtetrahalogenid umsetzte, werden erfindungsgemäß gemischte aliphatisch-aromatische Äther, deren Alkylrest mindestens 3 Kohlenstoffatome enthält, bei Temperaturen von mehr als 3000, insbesondere 300 bis 3500, mit substituierten Silanen umgesetzt, in denen wenigstens eine Valenz des Siliciums unmittelbar an ein Halpgenatom gebunden ist.The invention opens up a new way for the production of silicic acid esters of alkylated phenols. While alkylated aromatic oxy compounds have previously been reacted with silicon tetrahalide, according to the invention mixed aliphatic-aromatic ethers, the alkyl radical of which contains at least 3 carbon atoms, are reacted with substituted silanes at temperatures of more than 300 0 , in particular 300 to 350 0 , in which at least one valence of the Silicon is bound directly to a Halpgenatom.
Der Alkylrest des Äthers kann linear oder verzweigt sein. Der Arylrest des Äthers kann ein- oder mehrkernig sein. Besonders geeignet sind Kresyl- und Diphenylreste, Als Halogensilan eignet sich für die Umsetzung besonders ein Siliciumtetrahalogenid und hier wieder Siliciumtetrachlorid. Die erhaltenen Kieselsäureester sollen auf dem Kunststoffgebiet verwendet werden.The alkyl radical of the ether can be linear or branched. The aryl residue of the ether can be or be polynuclear. Cresyl and diphenyl radicals are particularly suitable. Suitable as halosilane A silicon tetrahalide and here again silicon tetrachloride are particularly suitable for the implementation. The silicic acid esters obtained are intended to be used in the plastics field.
Beispiel a)Example a)
90 g Phenyl-butyläther (0,6 Mol) werden mit 17,1 ecm Siliciumtetrachlorid (0,15 Mol) 3 Stunden im Autoklav auf 300 bis 3500 erhitzt. Als gasförmige Reaktionsprodukte treten Chlorwasserstoff und a-Butylen auf. Nach Beendigung der Reaktion wird das Reaktionsprodukt fraktioniert im Vakuum destilliert. Bei 290 bis 2930 destilliert90 g of phenyl-butyl ether (0.6 mol) are heated with 17.1 cc of silicon tetrachloride (0.15 mole) of 3 hours in autoclave at 300 to 350 0th Hydrogen chloride and α-butylene occur as gaseous reaction products. After the reaction has ended, the reaction product is fractionally distilled in vacuo. Distilled at 290 to 293 0
609 527/531609 527/531
S 31521 IVb/12qS 31521 IVb / 12q
das reine Tetra-butylphenyl-orthosilikat als hellgelbes Öl.the pure tetra-butylphenyl orthosilicate as a light yellow Oil.
Wird die gleiche Reaktion bei Temperaturen unter 3000 ausgeführt, dann erhält man an Stelle des Tetra-butylphenyl-orthosilikates hauptsächlich Tetraphenylsilikat.If the same reaction at temperatures below 300 0 executed, is obtained mainly Tetraphenylsilikat in place of tetra-butylphenyl-ortho silicate.
60 g Kresyl-isopropyläther (4/10 Mol) werden mit 11,4 ecm Siliciumtetrachlorid (V10MoI) etwa 3 Stunden auf 300 bis 3500 erhitzt. Die anschließende Vakuumdestillation ergibt zwischen 270 und 2900 ein Gemisch verschiedener Kieselsäureester als viskoses, gelbes Öl, aus dem durch nochmalige Vakuumdestillation bei 283 bis 2860 (14 mm) reines Tetra-isopropylkresyl-orthosilikat erhalten wird. Als gasförmige Reaktionsprodukte treten geringe Mengen von Gas und Propylen auf.60 g of cresyl-isopropyl ether (4/10 mol) are heated with 11.4 cc of silicon tetrachloride (V 10 MOI) for about 3 hours at 300 to 350 0th The subsequent vacuum distillation gives between 270 and 290 0 a mixture of different silicic acid esters as a viscous, yellow oil, from which pure tetraisopropyl cresyl orthosilicate is obtained by repeated vacuum distillation at 283 to 286 0 (14 mm). Small amounts of gas and propylene occur as gaseous reaction products.
ao ? " - Beispiel c) ao ? "- example c)
■'·' 90,4 g o-Oxydiphenyl-butyläther (4/10 Mol) und ■11/4 ecm Siliciumtetrachlorid (V10MoI) werden 3V2 Stunden auf 3000 erhitzt. Nach Abdestillieren des nicht umgesetzten Äthers erhält man als Reaktionsprodukt ein hochviskoses gelbbraunes Öl, das sich als ein Gemisch von o-Oxydipheriyl-o-öxybutyldiphenyl-orthosilikaten erweist.■ '·' 90.4 g of o-oxydiphenyl-butyl ether (4/10 mole) and ■ 11/4 cc silicon tetrachloride (V 10 MoI) are heated 3V2 hours at 300 0th After the unreacted ether has been distilled off, the reaction product obtained is a highly viscous yellow-brown oil which turns out to be a mixture of o-oxydipheriyl-o-oxybutyldiphenyl-orthosilicates.
Beispiel d)Example d)
90,4 g o-Diphenyl-Butyläther (4/10 Mol) und 30,6 g Diphenyl-dichlorsilan (2/10 Mol) ergeben während 4stündigem Erhitzen auf etwa 3500 als Reaktionsprodukt ein gelbes viskoses öl,, dessen Zusammensetzung einem Di-butyldiphenoxy-diphenyl-silan entspricht.90.4 g o-diphenyl-butyl ether (4/10 mole) and 30.6 g of diphenyl-dichlorosilane (2/10 mole) arise during 4 hours of heating at approximately 350 0 as a reaction product, a yellow viscous oil ,, the composition of a di- butyldiphenoxy-diphenyl-silane.
Claims (1)
Französische Patentschrift Nr. 970355;
USA.-Patentschriften Nr. 2 335 012, 2 584 334.Referred publications:
French Patent No. 970355;
U.S. Patent Nos. 2,335,012, 2,584,334.
Family
ID=
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