# US 11,028,037 B2 · Method of removing nitrate compounds from adipic acid

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- Number: US 11,028,037 B2
- Document ID: US11028037B2
- Status: Granted
- Kind: B2
- Application number: 16/956,252
- Filed: 2018-12-13
- Published: 2020-10-08
- Granted: 2021-06-08
- Earliest claimed: 2017-12-22
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Romain Feniou; Mathieu Oullion
- Web page: https://patentgrep.com/patent/US11028037B2

## CPC

- C07C 51/27: with oxides of nitrogen or nitrogen-containing mineral acids
- B01J 8/24: according to "fluidised-bed" technique (B01J8/20 takes precedence)
- B01J 19/0013: {Controlling the temperature of the process}
- C07C 51/64: Separation; Purification; Stabilisation; Use of additives
- B01J 2208/00371: gaseous
- C07C 55/14: Adipic acid
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

The present invention relates to a method of removing nitrate compounds from solid adipic acid.

## Claims

### Claim 1

A method of removing a nitrate compound from solid adipic acid, said method comprising:
i) contacting solid adipic acid comprising a nitrate compound with a gas, wherein the contacting takes place at a temperature in a range of above 85° C. to 95° C.,
wherein i) is either:
a) not followed by any further contacting of the solid adipic acid with a gas wherein the further contacting takes place at a temperature higher than the temperature of i), or
b) followed by further contacting the solid adipic acid with a gas wherein the further contacting takes place at a temperature that is above the temperature of i) above 95° C., but below 100° C.

### Claim 2 (depends on 1)

The method of claim 1, wherein i) comprises one step or two or more consecutive steps of contacting the solid adipic acid with the gas and wherein in each of the two or more consecutive steps the contacting takes place at a temperature in the range of above 80° C. to 95° C.

### Claim 3 (depends on 1)

The method of claim 1, wherein the further contacting of b) comprises one step or two or more consecutive steps of further contacting the solid adipic acid with the gas and wherein in each of the two or more consecutive steps the further contacting takes place at a temperature which is above the temperature of i) but below 100° C.

### Claim 4 (depends on 1)

The method of claim 1, wherein, in i), the contacting takes place at a temperature in a range of 85° C. to 95° C.

### Claim 5 (depends on 1)

The method of claim 1, wherein a gas fed to i) and/or the further contacting of b) has a temperature in a range of above 110° C. to 150° C.

### Claim 6 (depends on 1)

The method of claim 1, wherein a gas fed to i) and a gas fed to the further contacting of b) have the same temperature.

### Claim 7 (depends on 1)

The method of claim 1, wherein the gas does not react with adipic acid at the temperature at which it is contacted with the adipic acid.

### Claim 8 (depends on 1)

The method of claim 1, further comprising:
ii) cooling hot adipic acid from which the nitrate compound has been removed to a temperature of below 50° C.

### Claim 9 (depends on 8)

The method of claim 8, wherein the cooling is conducted using a gas.

### Claim 10 (depends on 1)

The method of claim 1, wherein, in each of i) and the further contacting of b), one or more heat exchangers are employed for adjusting the temperature.

### Claim 11 (depends on 1)

The method of claim 1, herein the contacting of the solid adipic acid with the gas is conducted in one or more fluidized beds.

### Claim 12 (depends on 11)

The method of claim 11, wherein the gas is fed to the one or more fluidized beds at a gas flow of 0.1 m/s to 1.0 m/s.

### Claim 13 (depends on 1)

The method of claim 1, wherein solid adipic acid comprising the nitrate compound fed to i) is moist.

### Claim 14 (depends on 1)

The method of claim 1, wherein the solid adipic acid comprising the nitrate compound is obtained by:
oxidizing a mixture comprising cyclohexanol and cyclohexanone with nitric acid, to obtain crude adipic acid,
crystallizing the crude adipic acid from an aqueous solution followed by solid-liquid separation, to obtain adipic acid, and
recrystallizing one or two time(s) the adipic acid from an aqueous solution followed by solid-liquid separation.

### Claim 15 (depends on 1)

The method of claim 1, wherein the i) contacting takes place at a temperature in a range of 89° C. to 95° C., and is followed by further contacting the solid adipic acid with the gas at a temperature of 98° C. to below 100° C.

### Claim 16 (depends on 15)

The method of claim 15, wherein, after contacting the solid adipic acid with the gas at a temperature of 98° C. to below 100° C., the amount of the nitrate compound present in the solid adipic acid is from 20% to 50% of the amount of the nitrate compound present in the solid adipic acid before the i) contacting.

### Claim 17 (depends on 1)

The method of claim 1, wherein after (a) or (b) the amount of the nitrate compound present in the solid adipic acid is from 20% to 50% of the amount of the nitrate compound present in the solid adipic acid before the i) contacting.

### Claim 18 (depends on 15)

The method of claim 15, wherein a time for the i) contacting and a time for the further contacting are the same.

### Claim 19 (depends on 1)

The method of claim 1, wherein the i) contacting takes place at a temperature in a range of 85° C. to 89° C., and is followed by further contacting the solid adipic acid with the gas at a temperature of 95 to 98° C.