# US 9,751,891 B2 · Method for the synthesis of primary isohexide amines

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- Number: US 9,751,891 B2
- Document ID: US9751891B2
- Status: Granted
- Kind: B2
- Application number: 15/327,262
- Filed: 2014-07-18
- Published: 2017-06-22
- Granted: 2017-09-05
- Earliest claimed: 2014-07-18
- Assignees: Rheinisch-WestfäLische Technische Hochschlule (Rwth) Aachen
- Applicants: Rheinisch-Westfaelische Technische Hochschlule (Rwth) Aachen
- Inventors: Marcus Rose; Regina Palkovits; Rebecca Engel; Alireza Haji Begli; Christine Kroener
- Web page: https://patentgrep.com/patent/US9751891B2

## CPC

- C07D 493/04: Ortho-condensed systems
- B01J 21/18: Carbon
- B01J 23/462: {Ruthenium}
- B01J 35/19: {Catalysts containing parts with different compositions}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

A method for synthesizing a primary amine, having the steps of: a) providing at least one dianhydrohexitol, and b) aminating the dianhydrohexitol by reacting same with ammonia, the amination being performed by heterogeneous catalysis using a hydrogenation catalyst in the presence of hydrogen.

## Claims

### Claim 1

A method for preparing a primary amine comprising the steps of:
a) providing at least one dianhydrohexitol, and
b) amination of the dianhydrohexitol by reaction with ammonia,
wherein the amination is carried out by heterogeneous catalysis using a hydrogenation catalyst in the presence of hydrogen.

### Claim 2 (depends on 1)

The method as claimed in claim 1, wherein the hydrogenation catalyst used is a supported or unsupported metal catalyst of one or more hydrogenation-active transition metals or noble metals selected from the group comprising platinum, palladium, ruthenium, iridium, rhodium, chromium, molybdenum, tungsten, vanadium, nickel, cobalt, copper and iron.

### Claim 3 (depends on 1)

The method as claimed in claim 1, wherein the hydrogen is pressurized in a reactor to a hydrogen pressure in the range from ≧1 bar to ≦25 bar.

### Claim 4 (depends on 1)

The method as claimed in claim 1, wherein the amination is carried out at a temperature in the range from ≧100° C. to ≦250° C.

### Claim 5 (depends on 1)

The method as claimed in claim 1, wherein the amination is carried out in aqueous solution or solvent-free.

### Claim 6 (depends on 1)

The method as claimed in claim 1, wherein the dianhydrohexitol in step a) is initially charged in solid form or in aqueous solution.

### Claim 7 (depends on 1)

The method as claimed in claim 1, wherein ammonia is added in the form of a gas or liquid or as an aqueous ammonium solution.

### Claim 8 (depends on 1)

The method as claimed in claim 1, wherein the ammonia in step b) is present in the range from ≧5 eq. to ≦20 eq., based on the dianhydrohexitol.

### Claim 9 (depends on 1)

The method as claimed in claim 1, wherein the dianhydrohexitol provided in step a) is selected from the group comprising isosorbide, isomannide, isoidide and/or mixtures thereof.

### Claim 10 (depends on 1)

The method as claimed in claim 1, wherein the hydrogenation catalyst used is a supported or unsupported metal catalyst of one or more hydrogenation-active transition metals or noble metals selected from the group comprising ruthenium, platinum, palladium and nickel.

### Claim 11 (depends on 1)

The method as claimed in claim 1, wherein the hydrogenation catalyst is ruthenium supported on carbon.

### Claim 12 (depends on 1)

The method as claimed in claim 1, wherein the hydrogen is pressurized in a reactor to a hydrogen pressure in the range from ≧5 bar to ≦25 bar.

### Claim 13 (depends on 1)

The method as claimed in claim 1, wherein the hydrogen is pressurized in a reactor to a hydrogen pressure in the range from ≧10 bar to ≦25 bar.

### Claim 14 (depends on 1)

The method as claimed in claim 1, wherein the amination is carried out at a temperature in the range from ≧120° C. to ≦230° C.

### Claim 15 (depends on 1)

The method as claimed in claim 1, wherein the amination is carried out at a temperature in the range from ≧150° C. to ≦200° C.

### Claim 16 (depends on 1)

The method as claimed in claim 1, wherein the ammonia in step b) is present in the range from ≧10 eq. to ≦16 eq., based on the dianhydrohexitol.

### Claim 17 (depends on 1)

The method as claimed in claim 1, wherein the ammonia in step b) is present in the range ≧11 eq. to ≦13 eq., based on the dianhydrohexitol.