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US 11,440,926 B2Granted
Method for preparing aminopropylsilanes
AssigneeWacker Chemie AG
InventorsElke Fritz-Langhals, Richard Weidner
Life of this patent
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Abstract
Aminopropylalkoxysilanes of the formula H2N—CR2R3—CHR1—CH2—SiR4R5(OR6) I, are synthesized by hydrosilylating silazanes of the formulae and mixtures thereof, in the presence of a catalyst containing rhodium and/or iridium compounds, and then reacted with alcohol to form an aminopropylalkoxysilane.
Claims10
A method for synthesizing a 3-aminopropylalkoxysilane of the formula I
- H2N—CR2R3—CHR1—CH2—SiR4R5(OR6) I,
- comprising:
- a) hydrosilylating a silazane of the formulae IVa or IVb
- or a mixture thereof, in the presence of a catalyst A which comprises a rhodium compound, an iridium compound, or a mixture thereof to form a hydrosilylated product, and
- b) reacting the hydrosilylated product from step a) with an alcohol of the formula V
- R6—OH V,
- and recovering the 3-aminopropylalkoxysilane of the formula (I),
- where
- R1 to R3 independently of one another are hydrogen or a monovalent unsubstituted or substituted C1-C20 hydrocarbon radical optionally bridged by hydrocarbon radicals, and wherein one or more methylene units in the hydrocarbon radical are optionally replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, —S— or NRx groups, provided that when two or more methylene groups are so replaced, they are non-adjacent,
- R4 and R5 independently of one another are a monovalent unsubstituted or substituted C1-C20 hydrocarbon radical optionally bridged by hydrocarbon radicals, and wherein one or more methylene units in the hydrocarbon radical are optionally replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, —S— or NRx groups, provided that when two or more methylene groups are so replaced, they are non-adjacent,
- R6 is a hydrocarbon radical having 1 to 8 carbon atoms, where one or more non-adjacent carbon atoms are optionally replaced by oxygen provided that when two or more carbon atoms are replaced by oxygen, the carbon atoms are non-adjacent, and
- Rx is a monovalent unsubstituted or substituted C1-C20 hydrocarbon radical optionally bridged by hydrocarbon radicals, wherein one or more methylene units in the hydrocarbon radical are optionally replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, —S— groups, provided that when two or more methylene groups are so replaced, they are non-adjacent.
9 more elements
A method for synthesizing a 3-aminopropylalkoxysilane of the formula I
- H2N—CR2R3—CHR1—CH2—SiR4R5(OR6) I,
- comprising:
- a) in a first step, reacting an olefinic amine of the formula II
- H2N—CR2R3—CHR1═CH2 II
- with a chlorosilane of the formula III
- ClSiR4R5H III,
- forming a silazane mixture comprising silazanes of the formulae IVa and IVb
- b) in a second step, hydrosilylating the silazane mixture obtained in step a) in the presence of a catalyst A which comprises a rhodium compound, an iridium compound, or a mixture thereof to form a hydrosilylated product, and
- c) reacting the hydrosilylated product of step b) with an alcohol of the formula V
- R6—OH V,
- where
- R1 to R3 independently of one another are hydrogen or a monovalent unsubstituted or substituted C1-C20 hydrocarbon radical optionally bridged by hydrocarbon radicals, and wherein one or more methylene units in the hydrocarbon radical are optionally replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, —S— or NRx groups, provided that when two or more methylene groups are so replaced, they are non-adjacent,
- R4 and R5 independently of one another are a monovalent unsubstituted or substituted C1-C20 hydrocarbon radical optionally bridged by hydrocarbon radicals, and wherein one or more methylene units in the hydrocarbon radical are optionally replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, —S— or NRx groups, provided that when two or more methylene groups are so replaced, they are non-adjacent,
- R6 is a hydrocarbon radical having 1 to 8 carbon atoms, where one or more non-adjacent carbon atoms are optionally replaced by oxygen, provided that when two or more carbon atoms are replaced by oxygen, the carbon atoms are non-adjacent, and
- Rx is a monovalent unsubstituted or substituted C1-C20 hydrocarbon radical optionally bridged by hydrocarbon radicals, wherein one or more methylene units in the hydrocarbon radical are optionally replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, or —S— groups, provided that when two more methylene groups are so replaced, they are non-adjacent.
12 more elements
Dependencies are inferred from the claim text.