# US 10,370,319 B2 · Process for the manufacture of an adipic acid product

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- Number: US 10,370,319 B2
- Document ID: US10370319B2
- Status: Granted
- Kind: B2
- Application number: 15/764,195
- Filed: 2016-10-03
- Published: 2018-10-04
- Granted: 2019-08-06
- Earliest claimed: 2015-10-05
- Assignees: Avantium Knowledge Centre B.V.
- Applicants: Avantium Knowledge Centre B.V.
- Inventors: Gerardus Johannes Maria Gruter; Jan Cornelis Van Der Waal; Lisette Magnee
- Web page: https://patentgrep.com/patent/US10370319B2

## CPC

- C07C 51/377: by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups {(C07C51/36 - C07C51/373 take precedence)}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Process for the manufacture of an adipic acid product by a reduction of a tetrahydrofuran dicarboxylic acid compound, wherein the tetrahydrofuran dicarboxylic acid compound is contacted with hydrogen iodide at a temperature of at least 100° C. in an inert atmosphere to yield the adipic acid product.

## Claims

### Claim 1

A method for the manufacture of an adipic acid product by a reduction of a tetrahydrofuran dicarboxylic acid compound, wherein the tetrahydrofuran dicarboxylic acid compound is tetrahydrofuran dicarboxylic acid, a hydrocarbyl ester of such acid, a metal salt of such acid or a combination thereof, wherein the tetrahydrofuran dicarboxylic acid compound is contacted with hydrogen iodide at a temperature of at least 100° C. in an inert atmosphere to yield the adipic acid product.

### Claim 2 (depends on 1)

A method according to claim 1, which is carried out in the presence of a solvent.

### Claim 3 (depends on 2)

A method according to claim 2, wherein the solvent is acetic acid, acetic anhydride or a mixture thereof.

### Claim 4 (depends on 2)

A method according to claim 2, wherein the solvent comprises water.

### Claim 5 (depends on 4)

A method according to claim 4, wherein an amount of water is in a range of 0.2 to 30 vol %, based on a volume of the solvent.

### Claim 6 (depends on 2)

A method according to claim 2, wherein a concentration of the tetrahydrofuran dicarboxylic acid compound in the solvent is in a range of 10 to 500 g/l.

### Claim 7 (depends on 1)

A method according to claim 1, which is carried out in the absence of a hydrodeoxygenation catalyst.

### Claim 8 (depends on 1)

A method according to claim 1, wherein the inert atmosphere comprises a gas selected from the group consisting of nitrogen, noble gases, carbon dioxide, steam and combinations thereof.

### Claim 9 (depends on 1)

A method according to claim 1, which is carried out in a continuous mode.

### Claim 10 (depends on 1)

A method according to claim 1, wherein a molar ratio of hydrogen iodide to tetrahydrofuran dicarboxylic acid compound is in a range of 4:1 to 25:1.

### Claim 11 (depends on 1)

A method according to claim 1, wherein the tetrahydrofuran dicarboxylic acid compound is contacted with hydrogen iodide at a temperature in the range of 130 to 300° C.

### Claim 12 (depends on 1)

A method according to claim 1, wherein the tetrahydrofuran dicarboxylic acid compound is contacted with the hydrogen iodide at a pressure of 2 to 100 bar.

### Claim 13 (depends on 1)

A method according to claim 1, wherein the tetrahydrofuran dicarboxylic acid compound is contacted with the hydrogen iodide for a period in a range of 0.5 to 10 hours.

### Claim 14 (depends on 1)

A method according to claim 1, wherein the tetrahydrofuran dicarboxylic acid compound has been obtained from the hydrogenation of furan dicarboxylic acid.

### Claim 15 (depends on 14)

A method according to claim 14, wherein the hydrogenation of furan dicarboxylic acid has been carried out with a hydrogen-containing gas in the presence of a hydrogenation catalyst.

### Claim 16

A method for the preparation of an adipic acid product, wherein a carbohydrate-containing biomass starting material is converted in the presence of an acid catalyst to a 5-hydroxymethyl furfural compound, wherein the 5-hydroxymethyl furfural compound is oxidized to a furandicarboxylic acid compound,
wherein the furandicarboxylic acid compound is hydrogenated to obtain a tetrahydrofuran dicarboxylic acid compound, wherein the tetrahydrofuran dicarboxylic acid compound is tetrahydrofuran dicarboxylic acid, a hydrocarbyl ester of such acid, a metal salt of such acid or a combination thereof; and
wherein the tetrahydrofuran dicarboxylic acid compound is contacted with a hydrogen iodide in an inert atmosphere, at a temperature of at least 100° C., to obtain the adipic acid product.