# US 8,772,548 B2 · Reaction of glycolaldehyde with an aminating agent

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- Number: US 8,772,548 B2
- Document ID: US8772548B2
- Status: Granted
- Kind: B2
- Application number: 13/516,479
- Filed: 2010-12-14
- Published: 2012-10-25
- Granted: 2014-07-08
- Earliest claimed: 2009-12-17
- Assignees: BASF SE
- Applicants: Wolfgang Mägerlein; Johann-Peter Melder; Jörg Pastre; Jan Eberhardt; Thomas Krug; Mirko Kreitschmann
- Inventors: Wolfgang Mägerlein; Johann-Peter Melder; Jörg Pastre; Jan Eberhardt; Thomas Krug; Mirko Kreitschmann
- Web page: https://patentgrep.com/patent/US8772548B2

## CPC

- C07C 209/26: by reduction with hydrogen
- C07C 213/00: Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C 215/08: with only one hydroxy group and one amino group bound to the carbon skeleton
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention relates to a process for reacting glycolaldehyde with an aminating agent in the presence of hydrogen and of a catalyst, the catalyst being activated by reducing a catalyst precursor or by reducing a passivated catalyst, which comprises effecting the reaction in the presence of a solvent and contacting the glycolaldehyde with the activated catalyst.

## Claims

### Claim 1

A process for reacting glycolaldehyde with an aminating agent in the presence of hydrogen and of a catalyst, the catalyst being activated by reducing a catalyst precursor or by reducing a passivated catalyst, which comprises effecting the reaction in the presence of a solvent and contacting the glycolaldehyde with the activated catalyst, wherein the catalyst precursor comprises, as catalytically active components, one or more oxygen compound of Ni, Co and/or Cu.

### Claim 2 (depends on 1)

The process according to claim 1, wherein the catalyst used comprises less than 0.4 mole percent of noble metal atoms selected from the group consisting of ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, gold and mercury.

### Claim 3 (depends on 1)

The process according to claim 1, wherein the reaction is performed at a temperature of 15 to 350° C.

### Claim 4 (depends on 1)

The process according to claim 1, wherein the reaction is performed at a pressure of 10 to 350 bar.

### Claim 5 (depends on 1)

The process according to claim 1, wherein the solvent is THF or water.

### Claim 6 (depends on 1)

The process according to claim 1, wherein the activated catalyst has a degree of reduction of 30% or more.

### Claim 7 (depends on 1)

The process according to claim 1, wherein the activated catalyst which has been prepared by reducing a passivated catalyst has, after the activation, a degree of reduction which is at least 2% greater than the degree of reduction of the passivated catalyst.

### Claim 8 (depends on 1)

The process according to claim 1, wherein the activated catalyst is handled under inert conditions during and after the reduction until the contacting with glycolaldehyde.

### Claim 9

A process for reacting glycolaldehyde with an aminating agent in the presence of hydrogen and of a catalyst, the catalyst being activated by reducing a catalyst precursor or by reducing a passivated catalyst, which comprises effecting the reaction in the presence of a solvent and contacting the glycolaldehyde with the activated catalyst, wherein the catalyst precursor comprises, as catalytically active components, one or more oxygen compounds of the metals of groups 8 and/or 9 and/or 10 and/or 11 of the periodic table of the elements, and wherein the catalyst used comprises less than 0.4 mole percent of noble metal atoms selected from the group consisting of ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, gold and mercury.