IP Library Granted Patent US 11,332,370
Granted Patent B2
US 11,332,370 · App. 16/902,900 · Granted May 17, 2022

Process for preparation of nitrogen oxides and nitric acid from nitrous oxide

Inventors: Gregory E. Bush (Pensacola, FL); Darrick K. Elmore (Pensacola, FL); Mikhail I. Khramov (Pensacola, FL)
Assignee: Ascend Performance Materials Operations LLC
C01B21/38B01J12/005B01J19/0013C01B21/24C01B21/36C07C51/316
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Quick Facts
Patent No.
US 11,332,370
App. No.
16/902,900
Granted
May 17, 2022
Kind
B2
Abstract

Described herein is an improved conversion of nitrous oxide (N 2 O) present as a by-product in a chemical process to NO x which can be further converted to a useful compound or material, such as nitric acid.

Claims (45)

1. A process for preparing adipic acid, comprising:

reacting at least one of cyclohexanone and cyclohexanol with nitric acid to produce adipic acid and an offgas comprising:

nitrous oxide; and

optionally nitrogen;

converting the nitrous oxide present in the offgas to nitrogen oxide by passing the offgas through a reactor operating at a temperature of 2400° F. or greater and a pressure of 10 psig or less to yield a product composition comprising nitrogen oxide;

compressing the product composition; and

converting nitrogen oxide in the compressed product composition to nitric acid.

2. The process of claim 1 , wherein the compressing comprises: compressing the product composition to a pressure ranging from 15 psig to 150 psig.

3. The process of claim 1 , further comprising further comprising:

quenching the product composition to form a cooled product composition.

4. The process of claim 3 , wherein the cooled product composition has a temperature less than 1600° F.

5. The process of claim 3 , wherein the cooled product composition has a temperature ranging from 900° F. to 1400° F.

6. The process of claim 1 , further comprising:

preheating the offgas prior to the converting.

7. The process of claim 6 , wherein the off gas is preheated to a temperature less than 1800° F.

8. The process of claim 1 , wherein the reactor operates at a temperature greater than 2600° F.

9. The process of claim 1 , wherein the converting step has a yield greater than 15%.

10. A process for preparing adipic acid, comprising:

reacting at least one of cyclohexanone and cyclohexanol with nitric acid to produce adipic acid and an offgas having a temperature less than 800° F. and comprising

nitrous oxide; and

optionally nitrogen;

preheating the offgas in a preheater unit to a temperature less than 1800° F.;

converting the nitrous oxide present in the offgas to nitrogen oxide at a yield of greater than 15% by passing the offgas through a reactor operating at a temperature of 2400° F. or greater and at a pressure of 10 psig or less to yield a product composition comprising nitrogen oxide; and

converting the nitrogen oxide to nitric acid.

11. The process of claim 10 , wherein the preheater unit is separate from the reactor.

12. The process of claim 10 , wherein the off gas leaving the adipic acid production reaction is not treated to remove nitrogen oxide.

13. The process of claim 10 , wherein the preheated offgas is directly fed to the reactor.

14. The process of claim 10 , wherein the preheating comprises:

preheating the offgas in a preheater unit to a temperature ranging from 900° F. to 1500° F.

15. A process for preparing adipic acid, comprising:

reacting at least one of cyclohexanone and cyclohexanol with nitric acid to produce adipic acid and an offgas having a temperature less than 800° F. and comprising

nitrous oxide; and

optionally nitrogen;

preheating the offgas in a preheater unit to a temperature less than 1800° F.;

converting nitrous oxide present in the offgas to nitrogen oxide at a yield of greater than 15% by passing the offgas through a reactor operating at a temperature of 2400° F. or greater and at a pressure of 10 psig or less to yield a product composition comprising nitrogen oxide;

compressing the product composition; and

converting nitrogen oxide present in the compressed product composition to nitric acid;

wherein the reactor has a length to diameter ratio (L/D) of greater than 4; and

wherein no external heat is added to the reactor after start of reaction.

16. The process of claim 15 , wherein the offgas comprises greater than 60 mol % nitrous oxide.

17. The process of claim 15 , wherein the residence time of the feed gas from the preheater to the reactor is less than 30 seconds.

18. The process of claim 15 , further comprising further comprising:

quenching the product composition to form a cooled product composition; and

compressing the cooled product composition.

19. The process of claim 18 , wherein the cooled product composition has a temperature less than 1600° F.

Assignments (6)
RELEASE OF SECURITY INTEREST Recorded Dec 23, 2025
From: WILMINGTON SAVINGS FUND SOCIETY, FSB
To: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
Reel/Frame 074050/0090 →
SECURITY INTEREST Recorded Dec 23, 2025
From: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
To: WILMINGTON SAVINGS FUND SOCIETY, FSB
Reel/Frame 074056/0183 →
SECURITY INTEREST Recorded Dec 19, 2025
From: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
To: WELLS FARGO BANK, NATIONAL ASSOCIATION
Reel/Frame 074007/0183 →
SECURITY INTEREST Recorded Apr 10, 2025
From: BANK OF AMERICA, N.A.
To: WILMINGTON SAVINGS FUND SOCIETY, FSB
Reel/Frame 070811/0705 →
SECURITY INTEREST Recorded Dec 8, 2022
From: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
To: WELLS FARGO CAPITAL FINANCE, LLC
Reel/Frame 062094/0172 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 7, 2020
From: BUSH, GREGORY E.; ELMORE, DARRICK K.; KHRAMOV, MIKHAIL I.
To: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
Reel/Frame 053996/0213 →