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US 12,595,339 B2Granted
Preparation of organosilicon compounds with aldehyde functionality
AssigneesDow Silicones Corporation, Dow Global Technologies LLC
InventorsJason Fisk, Robert Larsen, Haoquan Li, Michael Tulchinsky, Gary Wieber, David Devore, John Gohndrone, Michael Ferritto
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Abstract
A catalyzed hydroformylation process of an alkenyl-functional organosilicon compound with carbon monoxide and hydrogen produces an aldehyde-functional organosilicon compound.
Claims18
A reaction product prepared by a process comprising:
- 1) combining, under conditions to catalyze hydroformylation reaction, starting materials comprising
- (A) a gas comprising hydrogen and carbon monoxide,
- (B) an alkenyl-functional organosilicon compound, and
- (C) a rhodium/bisphosphite ligand complex catalyst, where the bisphosphite ligand has formula
- where
- R6 and R6′ are each independently selected from the group consisting of hydrogen, an alkyl group of 1 to 20 carbon atoms, a cyano group, a halogen group, and an alkoxy group of 1 to 20 carbon atoms;
- R7 and R7′ are each independently selected from the group consisting of an alkyl group of 3 to 20 carbon atoms, and a group of formula —SiR173, where each R17 is an independently selected monovalent hydrocarbon group of 1 to 20 carbon atoms;
- R8, R8′, R9, and R9′ are each independently selected from the group consisting of hydrogen, an alkyl group, a cyano group, a halogen group, and an alkoxy group, and
- R10 R10′, R11, and R11′ are each independently selected from the group consisting of hydrogen or and alkyl group;
- wherein the reaction product comprises
- the aldehyde-functional organosilicon compound, wherein
- the aldehyde-functional organosilicon compound has, per molecule, at least one aldehyde-functional group covalently bonded to silicon, wherein
- the aldehyde-functional group has formula
- where
- G is a divalent hydrocarbon group free of aliphatic unsaturation that has 2 to 8 carbon atoms;
- and
- the rhodium/bisphosphite ligand complex catalyst;
- and wherein the aldehyde-functional organosilicon compound comprises
- a) a first organosilicon compound comprising a linear aldehyde-functional moiety, and
- b) a second organosilicon compound comprising a branched aldehyde-functional moiety;
- wherein
- a molar ratio of the linear aldehyde-functional moiety/the branched aldehyde-functional moiety (N/I ratio)>6.
19 more elements
A process for preparing an aldehyde-functional organosilicon compound, said process comprising:
- 1) combining, under conditions to catalyze hydroformylation reaction, starting materials comprising
- (A) a gas comprising hydrogen and carbon monoxide,
- (B) an alkenyl-functional organosilicon compound, where the alkenyl-functional organosilicon compound comprises an alkenyl-functional silazane, and
- (C) a rhodium/bisphosphite ligand complex catalyst, where the bisphosphite ligand has formula
- where
- R6 and R6′ are each independently selected from the group consisting of hydrogen, an alkyl group of 1 to 20 carbon atoms, a cyano group, a halogen group, and an alkoxy group of 1 to 20 carbon atoms;
- R7 and R7′ are each independently selected from the group consisting of an alkyl group of 3 to 20 carbon atoms, and a group of formula —SiR173, where each R17 is an independently selected monovalent hydrocarbon group of 1 to 20 carbon atoms;
- R8, R8′, R9, and R9′ are each independently selected from the group consisting of hydrogen, an alkyl group, a cyano group, a halogen group, and an alkoxy group, and
- R10 R10′, R11, and R11′ are each independently selected from the group consisting of hydrogen or and alkyl group.
6 more elements
Dependencies are inferred from the claim text.