US4072701A
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Process for the production of sulfur containing organosilicon compounds
Assignee: Evonik Operations GmbH
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Filing: 1976-09-24
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Granted: 1978-02-07
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Expires: 1996-09-24
Abstract
Abstract There is provided a process for the production of sulfur containing organosilicon compounds of the formula (I) Z--Alk--S x --Alk--Z, where Z is the grouping: ##STR1## in which R 1 is an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group with 5 to 8 carbon atoms, the benzyl group, phenyl or phenyl substituted with at least one methyl, ethyl or chloro group and R 2 is alkoxy of 1 to 8 carbon atoms, methoxyethoxy, cycloalkoxy with 5 to 8 carbon atoms, phenoxy or benzyloxy, Alk is divalent saturated hydrocarbon group having 1 to 10 carbon atoms or such a group interrupted once or twice by --O--, --S-- or --NH-- and x is a number from 2.0 to 6.0 comprising reacting a compound of the formula (II) Y--Alk--Hal, where Y is: ##STR2## WHERE Hal is fluorine, chlorine, bromine or iodine with at least one compound of the formula R 3 OH in which R 3 is alkyl of 1 to 8 carbon atoms, methoxyethyl, cycloalkyl with 5 to 8 carbon atoms, phenyl or benzyl or in the case of forming (d) reacting a tris alkoxysilane with triethanolamine to form the corresponding silatrane and with a hydrosulfide of the formula (III) MeSH, in which Me is ammonium, an alkali metal atom or an equivalent of an alkaline earth metal and with sulfur, preferably in the presence of at least one organic solvent, separating from the halide formed, and removing the organic solvent.
Inventors
- 👤 Hans-Dieter Pletka
- 👤 Rudolf Michel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 03:05
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/54; C08K5/548; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F7/1872; C07F7/1892; C08K5/549
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
263 words
A process for the production of a sulfur containing organosilicon compound of the formula (I) Z-Alk-Sx-Alk-Z, where Z is the grouping: ##STR8## in which R 1 is an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, benzyl, phenyl or phenyl substituted with at least one methyl, ethyl or chloro group and R 2 is alkoxy of 1 to 8 carbon atoms, methoxyethoxy, cycloalkoxy having 5 to 8 carbon atoms, benzyloxy, phenoxy or phenoxy substituted with at least one methyl, ethyl or chloro group, Alk is a divalent hydrocarbon group having 1 to 10 carbon atoms or such a group interrupted once or twice by --O--, --S-- or --NH-- and x is a number from 2 to 6 comprising reacting a compound of the formula (II) Y-Alk-Hal, where Y is: ##STR9## where Hal is fluorine, chlorine, bromine or iodine with, when II is (a), (b) or (c), a compound of the formula R 3 OH in which R 3 is alkyl of 1 to 8 carbon atoms, methoxyethyl, cycloalkyl having 5 to 8 carbon atoms, benzyl, phenyl or phenyl substituted with at least one methyl, ethyl or chloro group and reacting the resulting product or, when II is (d) reacting II, with a hydrosulfide of the formula III MeSH in which Me is ammonium, an alkali metal atom, an equivalent of an alkaline earth metal or zinc and with sulfur, the amount of sulfur together with the sulfur in MeSH being sufficient to satisfy x in formula I, and removing the ammonium or metal halide.
Claim 2
Dependent Claim
263 words
A process for the production of a sulfur containing organosilicon compound of the formula (I) Z-Alk-Sx-Alk-Z, where Z is the grouping: ##STR8## in which R 1 is an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, benzyl, phenyl or phenyl substituted with at least one methyl, ethyl or chloro group and R 2 is alkoxy of 1 to 8 carbon atoms, methoxyethoxy, cycloalkoxy having 5 to 8 carbon atoms, benzyloxy, phenoxy or phenoxy substituted with at least one methyl, ethyl or chloro group, Alk is a divalent hydrocarbon group having 1 to 10 carbon atoms or such a group interrupted once or twice by --O--, --S-- or --NH-- and x is a number from 2 to 6 comprising reacting a compound of the formula (II) Y-Alk-Hal, where Y is: ##STR9## where Hal is fluorine, chlorine, bromine or iodine with, when II is (a), (b) or (c), a compound of the formula R 3 OH in which R 3 is alkyl of 1 to 8 carbon atoms, methoxyethyl, cycloalkyl having 5 to 8 carbon atoms, benzyl, phenyl or phenyl substituted with at least one methyl, ethyl or chloro group and reacting the resulting product or, when II is (d) reacting II, with a hydrosulfide of the formula III MeSH in which Me is ammonium, an alkali metal atom, an equivalent of an alkaline earth metal or zinc and with sulfur, the amount of sulfur together with the sulfur in MeSH being sufficient to satisfy x in formula I, and removing the ammonium or metal halide.
Claim 3
Dependent Claim
23 words
The process of claim 1 wherein the reaction with the MeSH and sulfur is carried out in the presence of an organic solvent.
Claim 4
Dependent Claim
49 words
The process of claim 1 where R 2 is alkoxy of 1 to 8 carbon atoms, methoxyethoxy, cycloalkoxy having 5 to 8 carbon atoms, phenoxy or benzyloxy and R 3 is alkyl of 1 to 8 carbon atoms, methoxyethyl, cycloalkyl having 5 to 8 carbon atoms, phenyl or benzyl.
Claim 5
Dependent Claim
34 words
The process of claim 3 wherein the reaction with the MeSH and sulfur is carried out in the presence of an organic solvent and the process includes the step of removing the organic solvent.
Claim 6
Dependent Claim
21 words
The process of claim 4 wherein the organic solvent is an alkanol, a cycloalkanol, a phenol or an inert organic solvent.
Claim 7
Dependent Claim
17 words
The process of claim 5 wherein the organic solvent is excess of the compound R 3 OH.
Claim 8
Dependent Claim
21 words
The process of claim 3 wherein all of the halogen atoms of Hal having an atomic weight of 9 to 80.
Claim 9
Dependent Claim
15 words
The process of claim 7 wherein all of the halogen atoms of Hal are chlorine.
Claim 10
Dependent Claim
13 words
The process of claim 8 wherein I is (c) and Y is (c).
Claim 11
Dependent Claim
48 words
The process of claim 3 wherein the reaction of II (a), (b) or (c) with R 3 OH is carried out at a temperature from 20° C to the boiling point and the reaction with MeSH and sulfur is carried out at 20° C to the boiling point.
Claim 12
Dependent Claim
12 words
The process of claim 3 wherein II is (a), (b) or (c).
Claim 13
Dependent Claim
24 words
The process of claim 11 wherein the hydrogen halide formed in the first step is removed prior to the reaction with MeSH and sulfur.
Claim 14
Dependent Claim
33 words
The process of claim 3 wherein in the step of sulfide formation there is employed sodium, potassium, cesium or ammonium hydrosulfide in powder form and the sulfur is also employed in powder form.
Claim 15
Dependent Claim
47 words
The process of claim 13 wherein the reaction is carried out in an inert organic solvent or a compound R 3 OH which at least partially dissolves the reactants, the reaction being carried out at a temperature of 20° C to the boiling point of the solvent.
Claim 16
Dependent Claim
36 words
The process of claim 14 wherein II is (a), (b) or (c) and the process comprises removing the hydrogen halide formed in the first step of the reaction prior to the reaction with MeSH and sulfur.
Claim 17
Dependent Claim
9 words
The process of claim 15 wherein Hal is chlorine.
Claim 18
Dependent Claim
9 words
The process of claim 16 wherein II is (c).
Claim 19
Dependent Claim
58 words
A process according to claim 11 wherein the hydrosulfide of formula III and the sulfur are reacted with the product resulting from the reaction of the compound of formula II with the compound R 3 OH before removing any excess compound R 3 OH from the reaction product of the compound of formula II and R 3 OH.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-02-06 | 1981-08-08 | 1982-02-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-02-06 | 1985-08-08 | 1986-02-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-02-06 | 1989-08-08 | 1990-02-07 | $7700.00 | Window Closed / Lapsed |