# US 9,518,005 B2 · Process for production of hexamethylenediamine from carbohydrate-containing materials and intermediates therefor

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- Number: US 9,518,005 B2
- Document ID: US9518005B2
- Status: Granted
- Kind: B2
- Application number: 14/687,892
- Filed: 2015-04-15
- Published: 2016-03-10
- Granted: 2016-12-13
- Earliest claimed: 2012-01-18
- Assignees: Rennovia Inc.
- Applicants: Rennovia, Inc.
- Inventors: Eric L. Dias; James A. W. Shoemaker; Thomas R. Boussie; Vincent J. Murphy
- Web page: https://patentgrep.com/patent/US9518005B2

## CPC

- C07C 29/157: containing platinum group metals or compounds thereof
- C07C 29/132: by reduction of an oxygen containing functional group
- C07C 29/141: with hydrogen or hydrogen-containing gases
- C07C 29/175: {with simultaneous reduction of an oxo group}
- C07C 209/16: with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07D 307/46: Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D 307/48: Furfural
- C07D 307/50: Preparation from natural products
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Processes are disclosed for the conversion of a carbohydrate source to hexamethylenediamine (HMDA) and to intermediates useful for the production of hexamethylenediamine and other industrial chemicals. HMDA is produced by direct reduction of a furfural substrate to 1,6-hexanediol in the presence of hydrogen and a heterogeneous reduction catalyst comprising Pt or by indirect reduction of a furfural substrate to 1,6-hexanediol wherein 1,2,6-hexanetriol is produced by reduction of the furfural substrate in the presence of hydrogen and a catalyst comprising Pt and 1,2,6-hexanediol is then converted by hydrogenation in the presence of a catalyst comprising Pt to 1,6 hexanediol, each process then proceding to the production of HMDA by known routes, such as amination of the 1,6 hexanediol. Catalysts useful for the direct and indirect production of 1,6-hexanediol are also disclosed.

## Claims

### Claim 1

A process for producing a product comprising 1,6-hexanediol, the process comprising:
providing a reaction product mixture, wherein the reaction product mixture comprises 1,6-hexanediol, 1,2,6-hexanetriol, and one or more other products selected from the group consisting of 1,5-hexanediol, 1,2,5-hexanetriol, 1,2,5,6-hexanequatrol, 1-hexanol, and 2-hexanol; and
subjecting the product mixture to fractional distillation under subatmospheric pressure,
wherein the fractional distillation separates the 1,6-hexanediol from one or more products in the product mixture to produce a product comprising 1,6-hexanediol.

### Claim 2 (depends on 1)

The process of claim 1, wherein the reaction product mixture further comprises a solvent selected from the group consisting of water, an alcohol, an ester, an ether, a ketone, or a mixture thereof.

### Claim 3 (depends on 1)

The process of claim 1, further comprising recycling the 1,2,6-hexanetriol to a reduction reaction to produce 1,6-hexanediol, wherein the reduction reaction comprises reacting the 1,2,6-hexanetriol with hydrogen in the presence of a heterogeneous reduction catalyst comprising Pt.

### Claim 4 (depends on 2)

The process of claim 2, further comprising recycling the 1,2,6-hexanetriol to a reduction reaction to produce 1,6-hexanediol, wherein the reduction reaction comprises reacting the 1,2,6-hexanetriol with hydrogen in the presence of a heterogeneous reduction catalyst comprising Pt.

### Claim 5 (depends on 1)

The process of claim 1, wherein the reaction product mixture further comprises 1,2-hexanediol.

### Claim 6 (depends on 1)

The process of claim 1, further comprising reacting a furfural substrate with hydrogen in the presence of a heterogeneous reduction catalyst comprising Pt to provide the reaction product mixture.

### Claim 7 (depends on 1)

The process of claim 1, further comprising converting the 1,6-hexanediol to hexamethylenediamine.

### Claim 8 (depends on 3)

The process of claim 3, further comprising converting the 1,6-hexanediol to hexamethylenediamine.

### Claim 9 (depends on 4)

The process of claim 4, further comprising reacting a furfural substrate with hydrogen in the presence of a heterogeneous reduction catalyst comprising Pt to provide the reaction product mixture.

### Claim 10 (depends on 9)

The process of claim 9, wherein the reaction product mixture further comprises 1,2-hexanediol.

### Claim 11 (depends on 10)

The process of claim 10, further comprising converting the 1,6-hexanediol to hexamethylenediamine.