# US 2020/0399291 A1 · Method of making an organoaminosilane

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- Number: US 2020/0399291 A1
- Document ID: US20200399291A1
- Status: Published application
- Kind: A1
- Application number: 16/979,230
- Filed: 2019-02-13
- Published: 2020-12-24
- Earliest claimed: 2018-05-23
- Assignees: Dow Silicones Corporation
- Applicants: Dow Silicones Corporation
- Inventors: Anthony E. Foss; Jesse A. Maddock; Brian D. Rekken; Michael D. Telgenhoff
- Web page: https://patentgrep.com/patent/US20200399291A1

## CPC

- C07F 7/10: containing nitrogen {having a Si-N linkage}
- B01J 4/001: {Feed or outlet devices as such, e.g. feeding tubes}
- B01J 19/0053: {Details of the reactor}
- C07F 7/025: {without C-silicon linkages}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

A method of making an aminosilane, the method comprising: forming a reaction mixture comprising a hydridosilane, an amine and a dehydrogenative coupling catalyst in a reactor; subjecting the reaction mixture to conditions sufficient to cause a dehydrogenative coupling reaction between the hydridosilane and the amine to form the aminosilane and hydrogen gas; and venting the hydrogen gas; wherein the forming of the reaction mixture comprising the hydridosilane, the amine and the dehydrogenative coupling catalyst comprises continuously feeding the hydridosilane to the reactor containing the amine and the dehydrogenative coupling catalyst.

## Claims

### Claim 1

A method of making an aminosilane, the method comprising:
forming a reaction mixture comprising a hydridosilane selected from monosilane and disilane, an amine and a dehydrogenative coupling catalyst in a reactor;
subjecting the reaction mixture to conditions sufficient to cause a dehydrogenative coupling reaction between the hydridosilane and the amine to form the aminosilane and hydrogen gas; and
venting the hydrogen gas from the reactor;
wherein the forming of the reaction mixture comprising the hydridosilane, the amine and the dehydrogenative coupling catalyst comprises continuously feeding the hydridosilane to the reactor by bubbling it through the amine and dehydrogenative coupling catalyst.

### Claim 2 (depends on 1)

A method according to claim 1, wherein the venting of the hydrogen gas is continuous.

### Claim 3 (depends on 1)

A method according to claim 1, wherein the aminosilane is an organoaminosilane or trisilylamine.

### Claim 4 (depends on 1)

A method according to claim 1, wherein the amine is a primary or secondary amine according to formula (I)
RaNH3-a, (I)
where each R independently is hydrocarbyl having from 1 to 18 carbon atoms and subscript a is 1 or 2.

### Claim 5 (depends on 1)

A method according to claim 1, wherein the forming of the reaction mixture comprising the hydridosilane, the amine and the dehydrogenative coupling catalyst, comprises the addition of a dehydrogenative coupling pre-catalyst to the reactor and forming the dehydrogenative coupling catalyst from the dehydrogenative coupling pre-catalyst in the reactor.

### Claim 6 (depends on 5)

A method according to claim 5, wherein the dehydrogenative coupling pre-catalyst is ethylmethylmagnesium, propylmethylmagnesium, propylethylmagnesium, butylmethylmagnesium, butylethylmagnesium, dibutylmagnesium or butylpropylmagnesium.

### Claim 7 (depends on 1)

A method according to claim 1, further comprising a) or b)
a) wherein the reaction mixture further comprises a solvent;
b) wherein the conditions sufficient to cause the dehydrogenative coupling reaction between the hydridosilane and the amine to form the aminosilane and hydrogen gas include a temperature from 70 to 170° C. and a pressure from above 1 atmosphere.

### Claim 8 (depends on 7)

A method according claim 7, wherein the solvent is a hydrocarbon solvent having from 5 to 30 carbon atoms, the temperature is from 90 to 150° C., and the pressure is above 4 atmospheres.

### Claim 9 (depends on 1)

A method according to claim 1, wherein the aminosilane is an organoaminosilane according to formula (II)
(H3Si)3-aNRa, (II)
or formula (III)
(RaNH2-a)bSi2H6-b (III)
where each R independently is hydrocarbyl having from 1 to 18 carbon atoms and subscript a is 1 or 2, and subscript b is 1 or 2.

### Claim 10 (depends on 1)

A method according to claim 1, wherein the reactor is equipped with a gas vent, an inlet for hydridosilane gas, where the inlet is positioned so that the hydridosilane will bubble through the amine in the reactor, and a heater.