IP Library Granted Patent US 7,518,009
Granted Patent B2
US 7,518,009 · App. 11/415,183 · Granted Apr 14, 2009

Process for preparing mercaptoorganyl (alkoxysilanes)

Assignee: Evonik Degussa GmbH
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Quick Facts
Patent No.
US 7,518,009
App. No.
11/415,183
Granted
Apr 14, 2009
Kind
B2
Abstract

The present invention relates to a process for preparing mercaptoorganyl(alkoxysilanes), by hydrogenating bis(alkoxy-silylorganyl) polysulphides with hydrogen in the presence of at least one alcohol and a doped metal catalyst. The doped metal catalyst comprises at least one substance from the group consisting of iron, iron compound, nickel, nickel compound, palladium, palladium compound, osmium, osmium compound, ruthenium, ruthenium compound, rhodium, rhodium compound, iridium and iridium compound plus at least one doping component.

Claims (30)

1. A process for preparing mercaptoorganyl(alkoxysilanes) comprising: hydrogenating bis(alkoxysilylorganyl) polysulphides with hydrogen in the presence of at least one alcohol and a doped metal catalyst, wherein the doped metal catalyst comprises at least one substance selected from the group consisting of: iron, iron compound, osmium, osmium compound, ruthenium, ruthenium compound, and at least one doping component, wherein said doping component comprises 0.001% to 15% by weight of said doped metal catalyst.

2. The process for preparing mercaptoorganyl(alkoxysilanes) of claim 1 , wherein the weight conversion is 0.00 1 to 10 g of mercaptoorganyl(alkoxysilane) per mmol of substance of the doped metal catalyst per minute.

3. The process for preparing mercaptoorganyl(alkoxysilanes) of claim 1 , wherein the molar conversion is 0.001 to 50 mmol of mercaptoorganyl(alkoxysilane) per mmol of substance of the doped metal catalyst per minute.

4. The process for preparing mercaptoorganyl(alkoxysilanes) of claim 1 , wherein the hydrogenation is carried out at a temperature of between 100 and 175° C. and under a hydrogen pressure of 5 to 55 bar, and wherein said doping component comprises 0.01%-7.5% by weight of said doped metal catalyst.

5. The process of claim 1 , wherein said doping component is sulphur, tin molybdenum or zirconium.

6. The process of claim 1 , wherein said doped metal catalyst is formed by the absorption, adsorption or deposition of said doping component.

7. The process for preparing mercaptoorganyl(alkoxysilanes) of claim 1 , wherein said mercaptoorganyl(alkoxysilanes) are compounds of the general formula (II):

W-A-SH  (II)

wherein:

W is SiY 1 Y 2 Y 3 or Si(OCH 2 —CH 2 —) 3 N and Y 1 , Y 2 , Y 3 each independently of one another may be hydroxyl (—OH), a linear, branched or cyclic hydrocarbon chain having 1-18 carbon atoms (C1-C18), a linear or branched alkyl acid group (C a H 2a+1 )—C(═O)O—with a=1-25, a linear or branched alkenyl acid group (C b H 2b−1 )—C(═O)O— with b=2-25, a linear or branched substituted alkyl or alkenyl acid group, an unsubstituted, halogen-substituted or alkyl-substituted cycloalkane radical having 5-12 carbon atoms, benzyl radical, a halogen-substituted or alkyl-substituted phenyl radical, a linear or branched alkoxy group, a cycloallcoxy group having 5-12 carbon atoms, a halogen-substituted or alkyl-substituted phenoxy or benzyloxy group, an alkyl ether group O—(CR I 2 —CR I 2 )—O-Alk or alkyl polyether group O—(CR I 2 —CR I 2 O) y -Alk, with y=2-25 and wherein R I independently at each occurrence is H or an alkyl group, Alk being a linear or branched, saturated or unsaturated alkyl chain having 1-30 carbon atoms (C1-C30), and

A is a linear or branched, saturated or unsaturated aliphatic, aromatic or mixedly aliphatic/aromatic divalent C1-C30 hydrocarbon chain.

8. The process for preparing a mercaptoorganyl(alkoxysilane) of claim 7 , wherein said mercaptoorganyl(alkoxysilane) of formula (II) is selected from the group consisting of:

3-mercaptopropyl(trimethoxysilane), 3-mercaptopropyl(dimethoxyhydroxysilane), 3-mercaptopropyl(triethoxysilane), 3-mercaptopropyl(diethoxyhydroxysilane), 3-mercaptopropyl(diethoxymethoxysilane), 3-mercaptopropyl(tripropoxysilane), 3-mercaptopropyl(dipropoxymethoxysilane), 3-mercaptopropyl(dipropoxyhydroxysilane), 3-mercaptopropyl(tridodecanoxysilane), 3-mercaptopropyl(didodecanoxyhydroxysilane), 3-mercaptopropyl(tritetradecanoxysilane), 3-mercaptopropyl(trihexadecanoxysilane), 3-mercaptopropyl(trioctadecanoxysilane), 3-mercaptopropyl(didodecanoxy)tetradecanoxysilane, 3-mercaptopropyl(dodecanoxy)tetradecanoxy(hexadecanoxy)silane, 3-mercaptopropyl(dimethoxymethylsilane), 3-mercaptopropyl(methoxymethylhydroxysilane), 3-mercaptopropyl(methoxydimethylsilane), 3-mercaptopropyl(hydroxydimethylsilane), 3-mercaptopropyl(diethoxymethylsilane), 3-mercaptopropyl(ethoxyhydroxymethylsilane), 3-mercaptopropyl(ethoxydimethylsilane), 3-mercaptopropyl(dipropoxymethylsilane), 3-mercaptopropyl(propoxymethylhydroxysilane), 3-mercaptopropyl(propoxydimethylsilane), 3-mercaptopropyl(diisopropoxymethylsilane), 3-mercaptopropyl(isopropoxydimethylsilane), 3-mercaptopropyl(dibutoxymethylsilane), 3-mercaptopropyl(butoxydimethylsilane), 3-mercaptopropyl(disiobutoxymethylsilane), 3-mercaptopropyl(siobutoxymethylhydroxysilane), 3-mercaptopropyl(isobutoxydimethylsilane), 3-mercaptopropyl(didodecanoxymethylsilane), 3-mercaptopropyl(dodecanoxydimethylsilane), 3-mercaptopropyl(ditetradecanoxymethylsilane), 3-mercaptopropyl(tetradecanoxymethylhydroxysilane), 3-mercaptopropyl(tetradecanoxydimethylsilane), 2-mercaptoethyl(trimethoxysilane), 2-mercaptoethyl(triethoxysilane), 2-mercaptoethyl(diethoxymethoxysilane), 2-mercaptoethyl(tripropoxysilane), 2-mercaptoethyl(dipropoxymethoxysilane), 2-mercaptoethyl(tridodecanoxysilane), 2-mercaptoethyl(tritetradecanoxysilane), 2-mercaptoethyl(trihexadecanoxysilane), 2-mercaptoethyl(trioctadecanoxysilane), 2-mercaptoethyl(didodecanoxy)tetradecanoxysilan, 2-mercaptoethyl(dodecanoxy)tetradecanoxy(hexadecanoxy)silane, 2-mercaptoethyl(dimethoxymethylsilane), 2-mercaptoethyl(methoxymethylhydroxysilane), 2-mercaptoethyl(methoxydimethylsilane), 2-mercaptoethyl(diethoxymethylsilane), 2-mercaptoethyl(ethoxydimethylsilane), 2-mercaptoethyl(hydroxydimethylsilane), 1-mercaptomethyl(trimethoxysilane), 1-mercaptomethyl(triethoxysilane), 1-mercaptomethyl(diethoxymethoxysilane), 1-mercaptomethyl(diethoxyhydroxysilane), 1-mercaptomethyl(dipropoxymethoxysilane), 1-mercaptomethyl(tripropoxysilane), 1-mercaptomethyl(trimethoxysilane), 1-mercaptomethyl(dimethoxymethylsilane), 1-mercaptomethyl(methoxydimethylsilane), 1-mercaptomethyl(diethoxymethylsilane), 1-mercaptomethyl(ethoxymethylhydroxysilane), 1-mercaptomethyl(ethoxydimethylsilane), 3-mercaptobutyl(trimethoxysilane), 3-mercaptobutyl(triethoxysilane), 3-mercaptobutyl(diethoxymethoxysilane), 3-mercaptobutyl(tripropoxysilane), 3-mercaptobutyl(dipropoxymethoxysilane), 3-mercaptobutyl(dimethoxymethylsilane), 3-mercaptobutyl(diethoxymethylsilane), 3-mercaptobutyl(dimethylmethoxysilane), 3-mercaptobutyl(dimethylethoxysilane), 3-mercaptobutyl(dimethylhydroxysilane), 3-mercaptobutyl(tridodecanoxysilane), 3-mercaptobutyl(tritetradecanoxysilane), 3-mercaptobutyl(trihexadecanoxysilane), 3-mercaptobutyl(didodecanoxy)tetradecanoxysilan, 3-mercaptobutyl(dodecanoxy)tetradecanoxy(hexadecanoxy)silane, 3-mercapto-2-methyl-propyl(trimethoxysilane), 3-mercapto-2-methyl-propyl(triethoxysilane), 3-mercapto-2-methyl-propyl(diethoxymethoxysilane), 3-mercapto-2-methyl-propyl(tripropoxysilane), 3-mercapto-2-methyl-propyl(dipropoxymethoxysilane), 3-mercapto-2-methyl-propyl(tridodecanoxysilane), 3-mercapto-2-methyl-propyl(tritetradecanoxysilane), 3-mercapto-2-methyl-propyl(trihexadecanoxysilane), 3-mercapto-2-methyl-propyl(trioctadecanoxysilane), 3-mercapto-2-methyl-propyl(didodecanoxy)tetradecanoxysilane, 3-mercapto-2-methyl-propyl(dodecanoxy)tetradecanoxy(hexadecanoxy)silane, 3-mercapto-2-methyl-propyl(dimethoxymethylsilane), 3-mercapto-2-methyl-propyl(methoxydimethylsilane), 3-mercapto-2-methyl-propyl(diethoxymethylsilane), 3-mercapto-2-methyl-propyl(ethoxydimethylsilane), 3-mercapto-2-methyl-propyl(hydroxydimethylsilane), 3-mercapto-2-methyl-propyl(dipropoxymethylsilane), 3-mercapto-2-methyl-propyl(propoxydimethylsilane), 3-mercapto-2-methyl-propyl(diisopropoxymethylsilane), 3-mercapto-2-methyl-propyl(isopropoxydimethylsilane), 3-mercapto-2-methyl-propyl(dibutoxymethylsilane), 3-mercapto-2-methyl-propyl(butoxydimethylsilane), 3-mercapto-2-methyl-propyl(diisobutoxymethylsilane), 3-mercapto-2-methyl-propyl(isobutoxydimethylsilane), 3-mercapto-2-methyl-propyl(didodecanoxymethylsilane), 3-mercapto-2-methyl-propyl(dodecanoxydimethylsilane), 3-mercapto-2-methyl-propyl(ditetradecanoxymethylsilane), 3-mercapto-2-methyl-propyl(tetradecanoxydimethylsilane), [(C 9 H 19 O—(CH 2 —CH 2 O) 2 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 3 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 4 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 5 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 6 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 2 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 3 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 4 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 5 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 6 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 2 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 3 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 4 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 5 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 6 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 2 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 3 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 4 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 5 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 6 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 2 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 3 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 4 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 5 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 6 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 2 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 3 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 4 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 5 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 6 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 2 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 3 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 4 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 5 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 6 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 2 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 3 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 4 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 5 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 6 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 2 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 3 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 4 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 5 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 6 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 2 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 3 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 4 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 5 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 6 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 2 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 3 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 4 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 5 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 6 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 2 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 3 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 4 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 5 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 6 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 2 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 3 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 4 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 5 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 6 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 2 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 3 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 4 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 5 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 6 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 2 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 3 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 4 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 5 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 6 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 2 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 3 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 4 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 5 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 6 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 2 ] 3 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 3 ] 3 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 4 ] 3 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 5 ] 3 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 6 ] 3 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 2 ] 3 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 3 ] 3 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 4 ] 3 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 5 ] 3 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 6 ] 3 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 2 ] 3 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 3 ] 3 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 4 ] 3 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 5 ] 3 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 6 ] 3 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 2 ] 3 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 3 ] 3 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 4 ] 3 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 5 ] 3 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 6 ] 3 Si(CH 2 ) 3 SH, and HS—CH 2 —CH 2 —CH 2 —Si(OCH 2 —CH 2 —) 3 N.

9. The process for preparing mercaptoorganyl(alkoxysilanes) of claim 8 , wherein the hydrogenation is carried out at a temperature of between 100 and 175° C. and under a hydrogen pressure of 5 to 55 bar.

10. The process for preparing mercaptoorganyl(alkoxysilanes) of claim 9 , wherein said process is carried out in a reaction mixture comprising an additive selected from the group consisting of: a titanium alkoxylate; an amine; water; and an organic or inorganic acid or base.

11. A process for preparing mercaptoorganyl(alkoxysilanes) comprising: hydrogenating bis(alkoxysilylorganyl) polysulphides with hydrogen in the presence of at least one alcohol and a doped metal catalyst, wherein the doped metal catalyst comprises at least one substance selected from the group consisting of: nickel, nickel compound, palladium, palladium compound, rhodium, rhodium compound, iridium and iridium compound, and at least one doping component.

12. The process of claim 11 , wherein said doping component is sulphur, tin molybdenum or zirconium.

13. The process of claim 12 , wherein said doped metal catalyst comprises palladium or a palladium compound and one or more doping components selected from the group consisting of: sulphur, tin and molybdenum.

14. The process of claim 12 , wherein said doped metal catalyst comprises nickel or a nickel compound and zirconium.

15. The process of claim 11 , wherein said doping component comprises 0.01%-7.5% by weight of said doped metal catalyst.

16. The process of claim 11 , wherein said doped metal catalyst is formed by the absorption, adsorption or deposition of said doping component.

17. The process for preparing mercaptoorganyl(alkoxysilanes) of claim 11 , wherein said mercaptoorganyl(alkoxysilanes) are compounds of the general formula (II):

W-A-SH   (II)

wherein:

W is SiY 1 Y 2 Y 3 or Si(OCH 2 —CH 2 —) 3 N and Y 1 , Y 2 , Y 3 each independently of one another may be hydroxyl (—OH), a linear, branched or cyclic hydrocarbon chain having 1-18 carbon atoms (C1-C18), a linear or branched alkyl acid group (C a H 2a+1 )—C(═O )O— with a=1-25, a linear or branched alkenyl acid group (C b H 2b−1 )—C(═O)O— with b=2-25, a linear or branched substituted alkyl or alkenyl acid group, an unsubstituted, halogen-substituted or alkyl-substituted cycloalkane radical having 5-12 carbon atoms, benzyl radical, a halogen-substituted or alkyl-substituted phenyl radical, a linear or branched alkoxy group, a cycloalkoxy group having 5-12 carbon atoms, a halogen-substituted or alkyl-substituted phenoxy or benzyloxy group, an alkyl ether group O—(CR I 2 —CR I 2 )—O-Alk or alkyl polyether group O—(CR I 2 —CR I 2 O) y -Alk, with y=2-25 and wherein R I independently at each occurrence is H or an alkyl group, Alk being a linear or branched, saturated or unsaturated ailcyl chain having 1-30 carbon atoms (C1-C30), and

A is a linear or branched, saturated or unsaturated aliphatic, aromatic or mixedly aliphatic/aromatic divalent C1-C30 hydrocarbon chain.

18. The process for preparing a mercaptoorganyl(alkoxy-silane) of claim 17 , wherein said mercaptoorganyl(alkoxy-silane) of formula (II) is selected from the group consisting of:

3-mercaptopropyl(trimethoxysilane), 3-mercaptopropyl(dimethoxyhydroxysilane), 3-mercaptopropyl(triethoxysilane), 3-mercaptopropyl(diethoxyhydroxysilane), 3-mercaptopropyl(diethoxymethoxysilane), 3-mercaptopropyl(tripropoxysilane), 3-mercaptopropyl(dipropoxymethoxysilane), 3-mercaptopropyl(dipropoxyhydroxysilane), 3-mercaptopropyl(tridodecanoxysilane), 3-mercaptopropyl(didodecanoxyhydroxysilane), 3-mercaptopropyl(tritetradecanoxysilane), 3-mercaptopropyl(trihexadecanoxysilane), 3-mercaptopropyl(trioctadecanoxysilane), 3-mercaptopropyl(didodecanoxy)tetradecanoxysilane, 3-mercaptopropyl(dodecanoxy)tetradecanoxy(hexadecanoxy)silane, 3-mercaptopropyl(dimethoxymethylsilane), 3-mercaptopropyl(methoxymethylhydroxysilane), 3-mercaptopropyl(methoxydimethylsilane), 3-mercaptopropyl(hydroxydimethylsilane), 3-mercaptopropyl(diethoxymethylsilane), 3-mercaptopropyl(ethoxyhydroxymethylsilane), 3-mercaptopropyl(ethoxydimethylsilane), 3-mercaptopropyl(dipropoxymethylsilane), 3-mercaptopropyl(propoxymethylhydroxysilane), 3-mercaptopropyl(propoxydimethylsilane), 3-mercaptopropyl(diisopropoxymethylsilane), 3-mercaptopropyl(isopropoxydimethylsilane), 3-mercaptopropyl(dibutoxymethylsilane), 3-mercaptopropyl(butoxydimethylsilane), 3-mercaptopropyl(disiobutoxymethylsilane), 3-mercaptopropyl(siobutoxymethylhydroxysilane), 3-mercaptopropyl(isobutoxydimethylsilane), 3-mercaptopropyl(didodecanoxymethylsilane), 3-mercaptopropyl(dodecanoxydimethylsilane), 3-mercaptopropyl(ditetradecanoxymethylsilane), 3-mercaptopropyl(tetradecanoxymethylhydroxysilane), 3-mercaptopropyl(tetradecanoxydimethylsilane), 2-mercaptoethyl(trimethoxysilane), 2-mercaptoethyl(triethoxysilane), 2-mercaptoethyl(diethoxymethoxysilane), 2-mercaptoethyl(tripropoxysilane), 2-mercaptoethyl(dipropoxymethoxysilane), 2-mercaptoethyl(tridodecanoxysilane), 2-mercaptoethyl(tritetradecanoxysilane), 2-mercaptoethyl(trihexadecanoxysilane), 2-mercaptoethyl(trioctadecanoxysilane), 2-mercaptoethyl(didodecanoxy)tetradecanoxysilan, 2-mercaptoethyl(dodecanoxy)tetradecanoxy(hexadecanoxy)silane, 2-mercaptoethyl(dimethoxymethylsilane), 2-mercaptoethyl(methoxymethylhydroxysilane), 2-mercaptoethyl(methoxydimethylsilane), 2-mercaptoethyl(diethoxymethylsilane), 2-mercaptoethyl(ethoxydimethylsilane), 2-mercaptoethyl(hydroxydimethylsilane), 1-mercaptomethyl(trimethoxysilane), 1-mercaptomethyl(triethoxysilane), 1-mercaptomethyl(diethoxymethoxysilane), 1-mercaptomethyl(diethoxyhydroxysilane), 1-mercaptomethyl(dipropoxymethoxysilane), 1-mercaptomethyl(tripropoxysilane), 1-mercaptomethyl(trimethoxysilane), 1-mercaptomethyl(dimethoxymethylsilane), 1-mercaptomethyl(methoxydimethylsilane), 1-mercaptomethyl(diethoxymethylsilane), 1-mercaptomethyl(ethoxymethylhydroxysilane), 1-mercaptomethyl(ethoxydimethylsilane), 3-mercaptobutyl(trimethoxysilane), 3-mercaptobutyl(triethoxysilane), 3-mercaptobutyl(diethoxymethoxysilane), 3-mercaptobutyl(tripropoxysilane), 3-mercaptobutyl(dipropoxymethoxysilane), 3-mercaptobutyl(dimethoxymethylsilane), 3-mercaptobutyl(diethoxymethylsilane), 3-mercaptobutyl(dimethylmethoxysilane), 3-mercaptobutyl(dimethylethoxysilane), 3-mercaptobutyl(dimethylhydroxysilane), 3-mercaptobutyl(tridodecanoxysilane), 3-mercaptobutyl(tritetradecanoxysilane), 3-mercaptobutyl(trihexadecanoxysilane), 3-mercaptobutyl(didodecanoxy)tetradecanoxysilan, 3-mercaptobutyl(dodecanoxy)tetradecanoxy(hexadecanoxy)silane, 3-mercapto-2-methyl-propyl(trimethoxysilane), 3-mercapto-2-methyl-propyl(triethoxysilane), 3-mercapto-2-methyl-propyl(diethoxymethoxysilane), 3-mercapto-2-methyl-propyl(tripropoxysilane), 3-mercapto-2-methyl-propyl(dipropoxymethoxysilane), 3-mercapto-2-methyl-propyl(tridodecanoxysilane), 3-mercapto-2-methyl-propyl(tritetradecanoxysilane), 3-mercapto-2-methyl-propyl(trihexadecanoxysilane), 3-mercapto-2-methyl-propyl(trioctadecanoxysilane), 3-mercapto-2-methyl-propyl(didodecanoxy)tetradecanoxysilane, 3-mercapto-2-methyl-propyl(dodecanoxy)tetradecanoxy(hexadecanoxy)silane, 3-mercapto-2-methyl-propyl(dimethoxymethylsilane), 3-mercapto-2-methyl-propyl(methoxydimethylsilane), 3-mercapto-2-methyl-propyl(diethoxymethylsilane), 3-mercapto-2-methyl-propyl(ethoxydimethylsilane), 3-mercapto-2-methyl-propyl(hydroxydimethylsilane), 3-mercapto-2-methyl-propyl(dipropoxymethylsilane), 3-mercapto-2-methyl-propyl(propoxydimethylsilane), 3-mercapto-2-methyl-propyl(diisopropoxymethylsilane), 3-mercapto-2-methyl-propyl(isopropoxydimethylsilane), 3-mercapto-2-methyl-propyl(dibutoxymethylsilane), 3-mercapto-2-methyl-propyl(butoxydimethylsilane), 3-mercapto-2-methyl-propyl(diisobutoxymethylsilane), 3-mercapto-2-methyl-propyl(isobutoxydimethylsilane), 3-mercapto-2-methyl-propyl(didodecanoxymethylsilane), 3-mercapto-2-methyl-propyl(dodecanoxydimethylsilane), 3-mercapto-2-methyl-propyl(ditetradecanoxymethylsilane), 3-mercapto-2-methyl-propyl(tetradecanoxydimethylsilane), [(C 9 H 19 O—(CH 2 —CH 2 O) 2 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 3 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 4 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 5 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 6 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 2 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 3 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 4 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 5 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 6 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 2 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 3 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 4 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 5 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 6 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 2 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 3 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 4 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 5 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 6 ](MeO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 2 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 3 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 4 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 5 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 6 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 2 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 3 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 4 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 5 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 6 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 2 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 3 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 4 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 5 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 6 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 2 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 3 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 4 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 14H 29 O—(CH 2 —CH 2 O) 5 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 6 ] 2 (MeO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 2 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 3 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 4 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 5 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 6 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 2 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 3 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 4 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 5 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 6 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 2 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 3 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 4 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 5 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 6 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 2 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 3 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 4 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 5 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 6 ](EtO) 2 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 2 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 3 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 4 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 5 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 6 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 2 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 3 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 4 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 5 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 6 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 2 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 3 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 4 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 5 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 6 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 2 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 3 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 4 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 5 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 6 ] 2 (EtO)Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 2 ] 3 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 3 ] 3 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 4 ] 3 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 5 ] 3 Si(CH 2 ) 3 SH, [(C 9 H 19 O—(CH 2 —CH 2 O) 6 ] 3 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 2 ] 3 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 3 ] 3 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 4 ] 3 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 5 ] 3 Si(CH 2 ) 3 SH, [(C 12 H 25 O—(CH 2 —CH 2 O) 6 ] 3 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 2 ] 3 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 3 ] 3 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 4 ] 3 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 5 ] 3 Si(CH 2 ) 3 SH, [(C 13 H 27 O—(CH 2 —CH 2 O) 6 ] 3 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 2 ] 3 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 3 ] 3 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 4 ] 3 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 5 ] 3 Si(CH 2 ) 3 SH, [(C 14 H 29 O—(CH 2 —CH 2 O) 6 ] 3 Si(CH 2 ) 3 SH, and HS—CH 2 —CH 2 —CH 2 —Si(OCH 2 —CH 2 —) 3 N.

19. The process for preparing mercaptoorganyl(alkoxysilanes) of claim 18 , wherein said hydrogenation is carried out at a temperature of between 100 and 175° C.; under a hydrogen pressure of 5 to 55 bar and wherein the amount of doping component, based on the weight of the doped metal catalyst, is 0.01%-7.5% by weight.

20. The process for preparing mercaptoorganyl(alkoxysilanes) of claim 19 , wherein said process is carried out in a reaction mixture containing an additive selected from the group consisting of: a titanium alkoxylate; an amine; water; and an organic or inorganic acid or base.

Assignments (5)
CHANGE OF NAME Recorded Feb 1, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051776/0773 →
CHANGE OF NAME Recorded Feb 23, 2010
From: DEGUSSA GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 024006/0127 →
CHANGE ADDRESS Recorded Feb 22, 2010
From: EVONIK DEGUSSA GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 023985/0296 →
CHANGE OF ENTITY Recorded Feb 22, 2010
From: DEGUSSA AG
To: DEGUSSA GMBH
Reel/Frame 023998/0937 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2006
From: KORTH, KARSTEN; WOLF, DORIT; SEEBALD, STEFFEN; ALBERT, PHILIP; PIETER, REIMUND; ALIG, ALFRED
To: DEGUSSA AG
Reel/Frame 017810/0064 →
Priority Claims (1)
DE 10 2005 020 535 · May 3, 2005 · national
Continuity (1)
Related Publication 20060252952A1 · Nov 9, 2006