Catalytic process for the preparation of thiocarboxylate silane
AssigneeMomentive Performance Materials Inc.
InventorsTiberiu Ladislau Simandan, Ilaria Vecchi, Holger Jurgen Glatzer
Life of this patent
Estimating the term…
Abstract
The invention is directed to a process for the preparation of thiocarboxylate silane comprising reacting an aqueous solution of a salt of a thiocarboxylic acid with a haloalkyl silane in the presence of a solid inorganic oxide-supported phase transfer catalyst. The invention is also directed to a process for the preparation of an aqueous solution of a salt of a thiocarboxylic acid which comprises reacting an aqueous solution of a sulfide and/or hydrosulfide with an acid halide in the presence of a said solid catalyst.
Claims23
A process for the preparation of thiocarboxylate silane comprising reacting an aqueous solution of a salt of a thiocarboxylic acid with a haloalkyl silane in the presence of a solid inorganic oxide-supported phrase transfer catalyst, wherein the solid inorganic support is a metal oxide or a metalloid oxide and wherein the solid inorganic oxide-supported phase transfer catalyst comprises at least one group of the structure of formula (III):
- [YSi(R1)aO(3-a)/2] (III)
- wherein
- each occurrence of Y is independently a quaternary ammonium halide-containing group having the structure of the formula (II):
- [X−][R3R4R5N+R6—] (II)
- wherein each occurrence of R1 is independently selected from the group consisting of an alkyl group of from 1 to 6 carbon atoms and phenyl;
- each R3, R4 and R5 is independently an alkyl containing from 1 to 12 carbon atoms, phenyl or benzyl;
- each R6 is an alkylene group containing from 1 to 6 carbon atoms;
- X− is a halide selected from the group consisting of F−, Cl−, Br− and I−;
- and a is an integer 0, 1 or 2, and wherein the weight percent of the [YSi(R1)aO(3-a)/2] group is from 1 to 50 weight percent, based upon the weight of the total solid support;
- and wherein the solid inorganic oxide-supported phase transfer catalyst formula (III) further optionally comprises an organic group having the structure of formula (IV):
- [QSi(R2)bO(3-b)/2] (IV)
- wherein each occurrence of R2 is independently selected from the group consisting of an alkyl group of from 1 to 6 carbon atoms and phenyl;
- each occurrence of Q is independently an organic group selected from the group consisting of a hydrocarbon group having from 1 to 18 carbon atoms and a heterocarbon group containing from 1 to 18 carbon atoms and at least one heteroatom selected from the group consisting of oxygen, sulfur and nitrogen, with the proviso that the heterocarbon group is bonded to the silicon atom through a C—Si bond;
- and the subscript b is an integer 0, 1 or 2, wherein the weight percent of the [QSi(R2)bO(3-b)/2] is from 0 to 20 weight percent, where the weight percents are based upon the total weight of the solid inorganic oxide-supported quaternary ammonium halide phase transfer catalyst, to provide a thiocarboxylate silane.
A process for the preparation of an aqueous solution of a salt of a thiocarboxylic acid which comprises reacting an aqueous solution of a sulfide and/or hydrosulfide with an acid halide and/or acid anhydride in the presence of a solid inorganic oxide-supported phrase transfer catalyst, wherein the solid inorganic support is a metal oxide or a metalloid oxide, and wherein the and wherein the solid inorganic oxide-supported phase transfer catalyst comprises at least one group of the structure of formula (III):
- [YSi(R1)aO(3-a)/2] (III)
- wherein
- each occurrence of Y is independently a quaternary ammonium halide-containing group having the structure of the formula (II):
- [X−][R3R4R5N+R6—] (II)
- wherein each occurrence of R1 is independently selected from the group consisting of an alkyl group of from 1 to 6 carbon atoms and phenyl;
- each R3, R4 and R5 is independently an alkyl containing from 1 to 12 carbon atoms, phenyl or benzyl;
- each R6 is an alkylene group containing from 1 to 6 carbon atoms;
- X− is a halide selected from the group consisting of F−, Cl−, Br− and I−;
- and a is an integer 0, 1 or 2, and wherein the weight percent of the [YSi(R1)aO(3-a)/2] group is from 1 to 50 weight percent, based upon the weight of the total solid support;
- and wherein the solid inorganic oxide-supported phase transfer catalyst formula (III) further optionally, comprises an organic group having the structure of formula (IV):
- [QSi(R2)bO(3-b)/2] (IV)
- wherein each occurrence of R2 is independently selected from the group consisting of an alkyl group of from 1 to 6 carbon atoms and phenyl;
- each occurrence of Q is independently an organic group selected from the group consisting of a hydrocarbon group having from 1 to 18 carbon atoms and a heterocarbon group containing from 1 to 18 carbon atoms and at least one heteroatom selected from the group consisting of oxygen, sulfur and nitrogen, with the proviso that the heterocarbon group is bonded to the silicon atom through a C—Si bond;
- and the subscript b is an integer 0, 1 or 2, wherein the weight percent of the [QSi(R2)bO(3-b)/2] is from 0 to 20 weight percent, where the weight percents are based upon the total weight of the solid inorganic oxide-supported quaternary ammonium halide phase transfer catalyst, to provide a thiocarboxylate silane.
Dependencies are inferred from the claim text.