# US 11,440,926 B2 · Method for preparing aminopropylsilanes

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- Number: US 11,440,926 B2
- Document ID: US11440926B2
- Status: Granted
- Kind: B2
- Application number: 16/603,329
- Filed: 2018-02-06
- Published: 2021-09-16
- Granted: 2022-09-13
- Earliest claimed: 2018-02-06
- Assignees: Wacker Chemie AG
- Applicants: Wacker Chemie AG
- Inventors: Elke Fritz-Langhals; Richard Weidner
- Web page: https://patentgrep.com/patent/US11440926B2

## CPC

- C07F 7/10: containing nitrogen {having a Si-N linkage}
- C07F 7/1888: {by reactions involving the formation of other Si-linkages, e.g. Si-N}
- C07F 7/188: {by reactions involving the formation of Si-O linkages}
- C07F 7/20: Purification, separation
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## 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.

## Claims

### Claim 1

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.

### Claim 2 (depends on 1)

The method of claim 1, wherein R1 is hydrogen.

### Claim 3 (depends on 1)

The method of claim 1, wherein R2 and R3 independently of one another are hydrogen or a methyl group.

### Claim 4 (depends on 2)

The method of claim 2, wherein R2 and R3 independently of one another are hydrogen or a methyl group.

### Claim 5 (depends on 1)

The method of claim 1, wherein R4 and R5 independently of one another are monovalent unsubstituted C1-C6 hydrocarbon radicals.

### Claim 6 (depends on 1)

The method of claim 1, wherein R6 is a hydrocarbon radical having 1 to 4 carbon atoms.

### Claim 7 (depends on 1)

The method of claim 1, wherein the catalyst A comprises at least one Rh or iridium complex that is 4-coordinate or 6-coordinate.

### Claim 8 (depends on 7)

The method of claim 7, in which the Rh and iridium complexes have ligands selected from the group consisting of halide, hydrogen, BF4−, mono- or bidentate N, P, As or Sb, N-heterocyclic carbene or alkenyl ligands, carbon monoxide, and mixtures thereof.

### Claim 9

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.

### Claim 10 (depends on 9)

The method of claim 9, in which, in the step a), at least 2 mole equivalents of olefinic amine of the formula II, based on chlorosilane of the formula III, are used, and where a biphasic liquid mixture formed during the reaction comprises a lower phase which contains the hydrochloride of the amine of the formula II and an upper phase which contains a silazane mixture comprising silanes of the formulae IVa and IVb, are separated from each other by phase separation prior to step b).