# US 8,772,547 B2 · Method for producing 1-adamantyl trimethylammonium hydroxide

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- Number: US 8,772,547 B2
- Document ID: US8772547B2
- Status: Granted
- Kind: B2
- Application number: 13/255,805
- Filed: 2010-03-11
- Published: 2012-01-12
- Granted: 2014-07-08
- Earliest claimed: 2009-03-12
- Assignees: BASF SE
- Applicants: Christof Wilhelm Wigbers; Martin Ernst; Laszlo Szarvas; Giovanni D'Andola; Ellen Dahlhoff; Gabriele Iffland; Peter Raatz; Falk Simon; Matthias Frauenkron
- Inventors: Christof Wilhelm Wigbers; Martin Ernst; Laszlo Szarvas; Giovanni D'Andola; Ellen Dahlhoff; Gabriele Iffland; Peter Raatz; Falk Simon; Matthias Frauenkron
- Web page: https://patentgrep.com/patent/US8772547B2

## CPC

- C07C 211/63: having quaternised nitrogen atoms bound to acyclic carbon atoms
- C07C 209/00: Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C 209/26: by reduction with hydrogen
- C07C 2603/74: Adamantanes
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention relates to a process for preparing 1-adamantyltrimethylammonium hydroxide, by A) reacting 1-adamantyldimethylamine with dimethyl sulfate to give 1-adamantyltrimethylammonium sulfate; and B) subjecting the 1-adamantyltrimethylammonium sulfate obtained in A) to anion exchange with an ion exchanger loaded with OH ions.

## Claims

### Claim 1

A process for preparing 1-adamantyltrimethylammonium hydroxide, comprising:
A) reacting 1-adamantyldimethylamine with dimethyl sulfate to give 1-adamantyltrimethylammonium sulfate; and
B) subjecting the 1-adamantyltrimethylammonium sulfate obtained in A) to anion exchange with an ion exchanger loaded with OH ions.

### Claim 2 (depends on 1)

The process of claim 1, wherein the 1-adamantyldimethylamine is obtained by subjecting 1-adamantylamine or a 1-adamantylammonium salt to a dimethylation.

### Claim 3 (depends on 2)

The process of claim 2, wherein the 1-adamantyldimethylamine is obtained from 1-adamantylammonium hydrochloride.

### Claim 4 (depends on 3)

The process of claim 3, wherein the 1-adamantylammonium hydrochloride is reacted with aqueous base to form 1-adamantylamine.

### Claim 5 (depends on 1)

The process of claim 1, wherein the 1-adamantyldimethylamine is obtained by subjecting formaldehyde to a reductive amination with 1-adamantylamine or a 1-adamantylammonium salt and hydrogen in the presence of a hydrogenation catalyst.

### Claim 6 (depends on 5)

The process of claim 5, wherein the reductive amination occurs in a system having two liquid phases.

### Claim 7 (depends on 5)

The process of claim 5, wherein the reductive amination is carried out with a solvent mixture comprising water and at least one aromatic hydrocarbon.

### Claim 8 (depends on 5)

The process of claim 5, wherein the hydrogenation catalyst comprises Raney nickel.

### Claim 9 (depends on 5)

The process of claim 5, wherein a reductive amination product is distilled.

### Claim 10 (depends on 5)

The process of claim 5, wherein 1-adamantylamine is obtained by treating 1-adamantylammonium hydrochloride with an aqueous solution of a base.

### Claim 11 (depends on 1)

The process of claim 1, wherein the 1-adamantyldimethylamine is obtained by subjecting formaldehyde to a reductive amination with 1-adamantylamine or a 1-adamantylammonium salt in the presence of formic acid.

### Claim 12 (depends on 1)

The process of claim 1, wherein the 1-adamantyldimethylamine is obtained by subjecting 1-adamantylamine or a 1-adamantylammonium salt to catalytic methylation with methanol.

### Claim 13 (depends on 1)

The process of claim 1, wherein the reacting A) with dimethyl sulfate occurs at a temperature of at least 40° C.

### Claim 14 (depends on 1)

The process of claim 1, wherein a molar amount ratio of 1-adamantyldimethylamine to dimethyl sulfate is at least 2:1.

### Claim 15 (depends on 1)

The process of claim 1, wherein the reacting A) produces a methylation product comprising at least 95%, by weight, of 1-adamantyltrimethylammonium sulfate, based on the total weight of 1-adamantyltrimethylammonium sulfate and 1-adamantyltrimethylammonium methylsulfate.

### Claim 16 (depends on 1)

The process of claim 1, where the ion exchanger is a strongly basic anion exchanger.

### Claim 17 (depends on 1)

The process of claim 1, further comprising:
C) optionally subjecting an aqueous 1-adamantyltrimethylammonium hydroxide solution obtained from the anion exchange B) to a partial separation from water.

### Claim 18 (depends on 17)

The process of claim 17, wherein the aqueous 1-adamantyltrimethylammonium hydroxide solution is subjected to the partial separation from water, and the resulting solution has a 1-adamantyltrimethylammonium hydroxide content of at least 10%, by weight, based on the total weight of the solution.

### Claim 19 (depends on 5)

The process of claim 5, wherein the reductive amination is carried out with a solvent mixture comprising water and xylene.

### Claim 20 (depends on 1)

The process of claim 1, wherein the reacting A) with dimethyl sulfate occurs at a temperature of at least 80° C.