IP Library Granted Patent US 11,976,025
Granted Patent B2
US 11,976,025 · App. 17/466,880 · Granted May 7, 2024

Acetonitrile separation process

Inventors: Kyle Kissell (Houston, TX); Basil Michaels (Houston, TX)
Assignee: Ascend Performance Materials Operations LLC
C07C253/34
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Quick Facts
Patent No.
US 11,976,025
App. No.
17/466,880
Granted
May 7, 2024
Kind
B2
Abstract

Provided herein are processes for the separation of acetonitrile from low-purity feedstock streams. The provided processes are particularly useful for isolating acetonitrile at high purity from chemical manufacturing waste streams that include methanol, water, and allyl alcohol.

Claims (26)

1. A process for producing acetonitrile, the process comprising:

digesting a feedstock stream comprising acetonitrile, methanol, hydrogen cyanide, and water to remove hydrogen cyanide in a digester to produce an intermediate acetonitrile stream comprising less than 1 wt % hydrogen cyanide;

distilling the intermediate acetonitrile stream in a first distillation column to yield a first bottoms stream comprising water, and a first distillate stream comprising acetonitrile, wherein the first distillation column is operated at a pressure less than 150 kPa; and

purifying the first distillate stream to yield a product acetonitrile stream and a recycle stream.

2. The process of claim 1 , wherein the feedstock stream comprises more than 50 wt % water and wherein the first distillate stream comprises less than 45 wt % water.

3. The process of claim 1 , wherein the feedstock stream and the first bottoms stream each further comprises from 0 to 1.0 wt. % allyl alcohol.

4. The process of claim 3 , wherein the feedstock stream comprises more than 0.05 wt % allyl alcohol and wherein the first distillate stream comprises less than 0.05 wt % allyl alcohol.

5. The process of claim 3 , wherein the mass ratio of the acetonitrile in the first distillate stream to the allyl alcohol in the first distillate stream is greater than 1000:1.

6. The process of claim 1 , wherein the mass ratio of the acetonitrile in the first distillate stream to the water in the first distillate stream is greater than 3:1.

7. The process of claim 1 , wherein sodium hydroxide and the feedstock stream are fed to the digester.

8. The process of claim 1 , wherein the feedstock stream and the first distillate stream each further comprises oxazole.

9. The process of claim 8 , wherein the feedstock stream comprises more than 0.09 wt % oxazole and wherein the first bottoms comprises less than 0.1 wt % oxazole.

10. The process of claim 1 , wherein the feedstock stream further comprises acrylonitrile.

11. The process of claim 1 , wherein the first distillation column is operated at a pressure less than 80 kPa.

12. The process of claim 1 , wherein the product acetonitrile stream comprises more than 98 wt % acetonitrile.

13. The process of claim 1 , wherein the purifying comprises:

distilling the first distillate stream in a second distillation column to yield a second distillate stream comprising methanol, and a second bottoms stream comprising acetonitrile.

14. The process of claim 13 , wherein the second distillation column is operated at a pressure less than 200 kPa.

15. The process of claim 13 , wherein the second distillate stream comprises more than 25 wt % methanol.

16. The process of claim 13 , wherein the purifying comprises:

distilling the second bottoms stream in a third distillation column to yield the recycle stream comprising acetonitrile, and a third bottoms stream comprising acetonitrile.

17. The process of claim 16 wherein the third distillation column is operated at a pressure less than 550 kPa.

18. The process of claim 16 , wherein the purifying comprises:

distilling the third bottoms stream in a fourth distillation column to yield the product acetonitrile stream, wherein the fourth distillation column is operated at a pressure less than 80 kPa.

19. The process of claim 1 , wherein the feedstock stream comprises more than 0.7 wt % methanol.

20. The process of claim 1 , wherein the feedstock comprises propionitrile.

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 Jan 18, 2022
From: KISSELL, KYLE; MICHAELS, BASIL
To: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
Reel/Frame 058678/0347 →