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US4031119A Expired / Lapsed US ⏱️ 0.0 years remaining

[Perfluoroalkyl(alkoxy)phenyl]methyldichlorosilanes and method of preparing same

Assignee: Individual
•
Filing: 1976-04-29
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Granted: 1977-06-21
•
Expires: 1996-04-29
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Abstract

Abstract The invention relates to [perfluoroalkyl(alkoxy)phenyl]methyldichlorosilanes characterized by the general formula ##STR1## where: R F = OCF 3 OC 2 F 5 , OC 2 F 4 OCF 3 , C 2 F 4 OCF 3 , C 3 F 7 and also to a method of preparing them. The method according to the invention consists in that fluorobromo[alkyl(alkoxy)]benzenes having the general formula ##STR2## where: R F = OCF 3 OC 2 F 5 , OC 2 F 4 OCF 3 , C 2 F 4 OCF 3 , C 3 F 7 are treated with magnesium taken in a 5 - 20 per cent excess with respect to the stoichiometric quantity in a solution of absolute diethyl ether or absolute tetrahydrofurane at a temperature of 8° - 60° C. The resulting fluorine-containing magnesiumbromo[alkyl(alkoxy)]benzenes are treated with three-functional silanes -- methyltrichlorosilane -- taken in a 100 - 500 per cent excess with respect to the stoichiometric quantity, or with methylchlorodiethoxysilane, taken in the stoichiometric quantity or in a 50 per cent excess with respect to the stoichiometric quantity, at a temperature of 18° - 60° C. In the case of methylchlorodiethoxysilane, the resultant product is fluorine-containing [alkyl(alkoxy)phenyl]methyldiethoxysilanes which are treated with acetyl chloride taken in a 25 - 50 per cent excess with respect to the stoichiometric quantity, at a temperature of 40° - 70° C, in the presence of ferric chloride as a catalyst. The proposed [perfluoroalkyl(alkoxy)phenyl]methyldichlorosilanes can be used for preparing organofluosilicon lubricants, greases, sealing counds, rubber mixtures having high resistance to heat, frost, petrol and oils, that can be used in various fields of technology. The described method can be used to obtain the proposed end products in yields as high as 96 per cent of theory.

Inventors

  • 👤 Alexei Ivanovich Ponomarev
  • 👤 Sergei Vasilievich Sokolov
  • 👤 Julia Alexeevna Larionova
  • 👤 Alexandr Leibovich Klebansky
  • 👤 Vsevolod Volfovich Berenblit
  • 👤 Jury Pavlovich Dolnakov
  • 👤 Lev Moiseevich Yagupolsky
  • 👤 Vladlen Vasilievich Malovik
  • 👤 Miron Onufrievich Lozinsky
  • 👤 Viktor Mikhailovich Belous
  • 👤 Boris Efimovich Gruz
  • 👤 Ljubov Antonovna Alexeeva
  • 👤 Anatoly Kirillovich Ankudinov
  • 👤 Rufina Mikhailovna Ryazanova

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 14:44
CPC Classifications
C; C07; C07C; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/17; C07C43/174; C07C43/1742; C07F; C07F3/00; C07F3/02; C07F7/00; C07F7/02; C07F7/08; C07F7/12; C08; C08G; C08G77/00; C08G77/04; C08G77/22; C08G77/24; C10; C10M; C10M171/00; C10M171/004; C10M2227/00; C10M2227/04; C10N; C10N2040/00; C10N2040/30; C10N2040/32; C10N2040/34; C10N2040/36; C10N2040/38; C10N2040/40; C10N2040/42; C10N2040/44; C10N2040/50

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 37 words
[Perfluoroalkyl(alkoxy)phenyl]methyldichlorosilanes having the general formula ##STR8## where: R F = OCF 3 , OC 2 F 5 , OC 2 F 4 OCF 3 , C 2 F 4 OCF 3 , C 3 F 7 .
Claim 2
Dependent Claim 37 words
[Perfluoroalkyl(alkoxy)phenyl]methyldichlorosilanes having the general formula ##STR8## where: R F = OCF 3 , OC 2 F 5 , OC 2 F 4 OCF 3 , C 2 F 4 OCF 3 , C 3 F 7 .
Claim 3
Independent Claim 235 words
A method of preparing [perfluoroalkyl(alkoxy)phenyl]methyldichlorosilanes having the general formula ##STR9## where: R F = OCF 3 , OC 2 F 5 , OC 2 F 4 OCF 3 , C 2 F 4 OCF 3 , C 3 F 7 consisting in that fluorine-containing bromo[alkyl(alkoxy)]benzenes having the general formula ##STR10## where: R F = OCF 3 , OC 2 F 5 , OC 2 F 4 OCF 3 , C 2 F 4 OCF 3 , C 3 F 7 are treated with magnesium taken in a 5 - 20 percent excess with respect to the stoichiometric quantity, in a solution of a polar solvent, selected from the group consisting of absolute diethyl ether and absolute tetrahydrofurane, at a temperature of 8° - 60° C; the resulting fluorine-containing magnesium-bromo[alkyl(alkoxy)]benzenes are treated with a three-functional silane selected from the group consisting of methyltrichlorosilane and methylchlorodiethoxysilane, at a temperature of 18° - 60° C, said methyltrichlorosilane being taken in a 100 - 500 percent excess of the stoichiometric quantity, and said methylchlorodiethoxysilane being taken in a quantity ranging from the stoichiometric one to a 50 percent excess of the stoichiometric quantity; in case of methylchlorodiethoxysilanes, the resultant products being fluorine-containing [alkyl(alkoxy)phenyl]methyldiethoxysilanes are treated with acetyl chloride taken in a 25 - 50 percent excess with respect to the stoichiometric quantity, at a temperature of 40° - 70° C, in the presence of ferric chloride as a catalyst.
Claim 4
Independent Claim 235 words
A method of preparing [perfluoroalkyl(alkoxy)phenyl]methyldichlorosilanes having the general formula ##STR9## where: R F = OCF 3 , OC 2 F 5 , OC 2 F 4 OCF 3 , C 2 F 4 OCF 3 , C 3 F 7 consisting in that fluorine-containing bromo[alkyl(alkoxy)]benzenes having the general formula ##STR10## where: R F = OCF 3 , OC 2 F 5 , OC 2 F 4 OCF 3 , C 2 F 4 OCF 3 , C 3 F 7 are treated with magnesium taken in a 5 - 20 percent excess with respect to the stoichiometric quantity, in a solution of a polar solvent, selected from the group consisting of absolute diethyl ether and absolute tetrahydrofurane, at a temperature of 8° - 60° C; the resulting fluorine-containing magnesium-bromo[alkyl(alkoxy)]benzenes are treated with a three-functional silane selected from the group consisting of methyltrichlorosilane and methylchlorodiethoxysilane, at a temperature of 18° - 60° C, said methyltrichlorosilane being taken in a 100 - 500 percent excess of the stoichiometric quantity, and said methylchlorodiethoxysilane being taken in a quantity ranging from the stoichiometric one to a 50 percent excess of the stoichiometric quantity; in case of methylchlorodiethoxysilanes, the resultant products being fluorine-containing [alkyl(alkoxy)phenyl]methyldiethoxysilanes are treated with acetyl chloride taken in a 25 - 50 percent excess with respect to the stoichiometric quantity, at a temperature of 40° - 70° C, in the presence of ferric chloride as a catalyst.
Claim 5
Dependent Claim 20 words
A method according to claim 2, in which fluorine-containing bromo[alkyl(alkoxy)]benzenes are treated with magnesium in the presence of methyl iodide.
Claim 6
Dependent Claim 37 words
A method according to claim 2, in which fluorine-containing magnesiumbromo[alkyl(alkoxy)]benzenes are treated with three-functional silanes in the presence of absolute hexane taken in the quantity of 30 - 400 percent of the weight of the three-functional silane.

References Cited (Backward Citations)

US3450738A Cited
US3422131A Cited
US3484470A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-06-20 1980-12-20 1981-06-21 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-06-20 1984-12-20 1985-06-21 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-06-20 1988-12-20 1989-06-21 $7700.00 Window Closed / Lapsed

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