Process for the preparation of sulfur- and...

Details Process for the preparation of sulfur- and... Process for the preparation of sulfur- and...

2000-11-13

2001-08-14

Shaver, Paul F. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Silicon containing

Reexamination Certificate

active

06274753

ABSTRACT:

INTRODUCTION AND BACKGROUND
The present invention relates to a process for the preparation of sulfur- and phosphorus-containing organosilicon compounds.
German application DE 2658368 C2 discloses compounds of the formula
[R
1
n
(R
2
O)
3−n
—Si—Alk—S—]
3
P═S,
in which Alk denotes an alkylene group having 2 to 4 carbon atoms, R
1
, R
2
denote an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a phenyl group, a benzyl group or the 2-methoxyethyl group, wherein R
1
or R
2
in each case can have identical or different meanings, and n=0, 1 or 2.
For the preparation of these compounds, thiophosphoryl chloride or bromide is reacted with a mercaptosilane of the formula
R
1
n
(R
2
O)
3−n
—Si—Alk—SH
with the abovementioned meanings.
Mercaptosilanes are expensive starting compounds, since as a rule they are prepared from the corresponding chlorosilanes (EP 471 164 B1, DE-AS 20 35 619, DE-PS 33 46 910, U.S. Pat. No. 3,849,471, GB-PS 1 102 251).
The disadvantage of these known processes is that expensive mercaptosilane is used as an educt for the preparation of the abovementioned phosphorus-containing compounds.
An object of the present invention is to provide an alternative process for the preparation of sulfur- and phosphorus-containing organosilicon compounds.
SUMMARY OF THE INVENTION
The above and other objects of the invention can be achieved by a process for the preparation of sulfur- and phosphorus-containing compounds of the formula
[R
1
n
(R
2
O)
3−n
—Si—Alk—S—]
3
P═S,
in which Alk denotes an alkylene group having 1 to 10 carbon atoms, R
1
, R
2
denote an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a phenyl group, a benzyl group or a 2-methoxyethyl group, wherein R
1
or R
2
in each case can have identical or different meanings, and n=0, 1 or 2, which is characterized in that halogen-containing silanes of the formula
R
1
n
(R
2
O)
3−n
—Si—Alk—Hal,
in which Alk denotes an alkylene group having 1 to 10 carbon atoms, R
1
, R
2
denote an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a phenyl group, a benzyl group or a 2-methoxyethyl group, wherein R
1
or R
2
in each case can have identical or different meanings, Hal denotes a halogen, preferably chlorine or bromine, and n=0, 1 or 2, are reacted with phosphorus pentasulfide (P
4
S
10
) and a metal sulfide.
The reaction can take place according to the equation
The reaction can be carried out in a solvent, preferably hexane, acetonitrile, toluene, heptane or cyclohexane. Since phosphorus pentasulfide dissolves in R
1
n
(R
2
O)
3−n
—Si—Alk—Hal, the reaction can be carried out without a solvent. The reaction can be carried out with exclusion of air and moisture.
The reaction can be carried out under an inert gas, preferably nitrogen, argon or helium. The reaction can be carried out at temperatures of 20° to 300° C., preferably 150° to 250° C. Sodium sulfide (Na
2
S), potassium sulfide (K
2
S) or ammonium sulfide ((NH
4
)
2
S) can be used as the metal sulfide.
The sulfur- and phosphorus-containing compounds prepared according to the invention can be used in rubber mixtures.


REFERENCES:
patent: 4152347 (1979-05-01), Pletka et al.
patent: 4416830 (1983-11-01), Morr et al.
patent: 26 58 368 (1978-07-01), None
Murav'ev I.V.: “Reactions of diphosphorus pentasulfide with alkyl halides”, Journal of General Chemistry USSR., Bd. 45, Nr. 8 -Jan. 20, 1976.
Nizamov I.S., etal., “Influence of nucleophilic reagents on the reactions of phosphorus sulfides and alkyl homologs of Davy's reagent with alkyl halides and dialkyl disulfides” Phosphorus, Sulfur Silicon Relat. Elem. 1998; vol. 132, pp. 85-100.
Russian Academy of Sciences; A.E. Arbuzov Institute of Organic and Physical Chemistry; Kazan; Russia, Dec. 18, 1997.

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