IP Library Granted Patent US 11,814,337
Granted Patent B2
US 11,814,337 · App. 17/466,882 · Granted Nov 14, 2023

Process for recovering acetonitrile

Inventors: Kyle Kissell (Houston, TX); Basil Michaels (Houston, TX)
Assignee: Ascend Performance Materials Operations LLC
C07C253/34B01D3/143
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Quick Facts
Patent No.
US 11,814,337
App. No.
17/466,882
Granted
Nov 14, 2023
Kind
B2
Abstract

A process for producing acetonitrile, the process comprising: treating a feedstock stream comprising methanol, allyl alcohol, oxazole, acetonitrile, water, and hydrogen cyanide to remove hydrogen cyanide and produce an acetonitrile stream comprising less than 1 wt. % hydrogen cyanide. The process further comprises the step of distilling the acetonitrile stream in a first distillation column to produce a first distillate comprising oxazole and methanol; a first intermediate acetonitrile stream comprising acetonitrile and oxazole and less than 1 wt % allyl alcohol; a first bottoms stream comprising allyl alcohol and water. The process further comprises the step of purifying the first intermediate acetonitrile stream to produce an acetonitrile product stream and a recycle stream comprising allyl alcohol.

Claims (44)

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

treating a feedstock stream comprising methanol, allyl alcohol, oxazole, acetonitrile, water, and hydrogen cyanide with a caustic solution to remove hydrogen cyanide and produce an acetonitrile stream comprising less than 1 wt. % hydrogen cyanide,

distilling the acetonitrile stream in a first distillation column operated at a pressure ranging from 100 kPa to 175 kPa to produce:

a first distillate comprising oxazole and methanol;

a first intermediate acetonitrile stream comprising acetonitrile and oxazole and less than 1 wt % allyl alcohol;

a first bottoms stream comprising allyl alcohol, and water; and

purifying the first intermediate acetonitrile stream to produce an acetonitrile product stream and a recycle stream comprising allyl alcohol.

2. The process of claim 1 , wherein the first intermediate acetonitrile stream is a sidedraw, optionally taken in the upper 70% of the first distillation column.

3. The process of claim 1 , wherein:

the first distillate comprises greater than 1 wt % oxazole and greater than 5 wt % methanol;

the first intermediate acetonitrile stream comprises greater than 25 wt % acetonitrile, less than 5 wt % oxazole, and less than 50 wt % water;

the first bottoms stream comprises greater than 0.01 wt % allyl alcohol and greater than 75 wt % water.

4. The process of claim 1 , wherein the recycle stream comprise a smaller amount of allyl alcohol than the first bottoms stream.

5. The process of claim 1 , wherein the acetonitrile product stream comprising greater than 98 wt % acetonitrile.

6. The process of claim 1 , wherein the first column comprises at least 30 trays.

7. The process of claim 1 , wherein the first column comprises a condenser and wherein the condenser uses chilled water.

8. The process of claim 1 , wherein the acetonitrile product stream comprises less than 1 wt. % methanol, wherein the feedstock stream further comprises oxazole and propionitrile, wherein the acetonitrile stream comprises less than 0.01 wt. % hydrogen cyanide, and wherein the acetonitrile product stream comprises greater than 99.5 wt. % acetonitrile.

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

treating the first intermediate acetonitrile stream comprising acetonitrile, oxazole, and hydrogen cyanide to produce a second intermediate acetonitrile stream comprising less than 1 wt % acrylonitrile and less than 1 wt % hydrogen cyanide.

10. The process of claim 9 , wherein the purifying comprises:

distilling the second intermediate acetonitrile stream to produce a third distillate comprising acetonitrile, less than 50 wt % water and greater than 0.1 wt % oxazole; and

a third bottoms comprising greater than 90 wt % acetonitrile and allyl alcohol.

11. The process of claim 10 , wherein the purifying comprises:

distilling the third bottoms to produce:

a fourth distillate comprising greater than 95 wt % acetonitrile; and

a fourth bottoms comprising greater than 1 wt % allyl alcohol and greater than 5 wt % propionitrile.

12. The process of claim 11 , wherein the purifying comprises:

treating the fourth distillate in a resin bed to remove oxazole.

13. The process of claim 1 , wherein the feedstock stream comprises greater than 0.05 wt. % methanol, less than 25 wt. % acetonitrile, and propionitrile.

14. The process of claim 1 , wherein the acetonitrile stream comprises less than 0.05 wt. % hydrogen cyanide.

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

treating a feedstock stream comprising methanol, allyl alcohol, oxazole, acetonitrile, water, and hydrogen cyanide with a caustic solution to remove hydrogen cyanide and produce an acetonitrile stream comprising less than 1 wt. % hydrogen cyanide,

distilling the acetonitrile stream in a first distillation column operated at a pressure ranging from 100 kPa to 175 kPa to produce to yield at least a first intermediate acetonitrile stream comprising acetonitrile and oxazole and less than 1 wt % allyl alcohol;

treating the first intermediate acetonitrile stream to produce a second intermediate acetonitrile stream comprising less than 1 wt % acrylonitrile and less than 1 wt % hydrogen cyanide; and

distilling the second intermediate acetonitrile stream to produce:

a third distillate comprising acetonitrile, less than 50 wt % water and greater than 0.1 wt % oxazole; and

a third bottoms comprising greater than 90 wt % acetonitrile and allyl alcohol.

16. The process of claim 15 , wherein the first intermediate acetonitrile stream is a sidedraw, optionally taken in the upper 70% of the first distillation column.

17. The process of claim 15 , wherein the third bottoms comprises greater than 98 wt % acetonitrile.

18. The process of claim 15 , further comprising distilling the third bottoms to produce:

a fourth distillate comprising greater than 95 wt % acetonitrile; and

a fourth bottoms comprising greater than 1 wt % allyl alcohol and greater than 5 wt % propionitrile.

19. The process of claim 18 , wherein the fourth distillate comprises greater than 98 wt % acetonitrile.

20. The process of claim 1 , wherein the caustic solution comprises sodium hydroxide, potassium hydroxide, magnesium hydroxide; calcium hydroxide, or combinations thereof.

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 Dec 14, 2021
From: KISSELL, KYLE; MICHAELS, BASIL
To: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
Reel/Frame 058384/0669 →