IP Library Granted Patent US 11,111,209
Granted Patent B2
US 11,111,209 · App. 16/682,167 · Granted Sep 7, 2021

Process for recovering acetonitrile from acrylonitrile waste streams

Inventors: Basil Michael (Houston, TX); Carl Alexander Diaz (Pearland, TX); Billy Nelson (Alvin, TX); Kyle Kissell (Manvel, TX)
Assignee: Ascend Performance Materials Operations LLC
C07C253/34
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Quick Facts
Patent No.
US 11,111,209
App. No.
16/682,167
Granted
Sep 7, 2021
Kind
B2
Abstract

A process for producing a high-purity acetonitrile product from a low-purity acetonitrile feedstock streams. In particular, the present disclosure relates to a process for producing a sales-grade, high purity acetonitrile by (a) distilling the feedstock stream in a to yield a crude acetonitrile stream, (b) treating the crude acetonitrile stream to produce an intermediate acetonitrile stream, (c) purifying the intermediate acetonitrile stream in a pressure swing distillation system to produce a recycle stream and an acetonitrile product stream, (d) recycling the recycle stream to the first distillation column, and (e) distilling the acetonitrile product stream to yield a purified acetonitrile product stream of at least 98 wt. % acetonitrile.

Claims (34)

1. A process for recovering acetonitrile, comprising the steps of:

distilling a feedstock stream comprising methanol and acetonitrile present in an amount equal to or less than 10 wt % in a first distillation column to yield a crude acetonitrile stream comprising methanol,

treating the crude acetonitrile stream to remove hydrogen cyanide and produce an intermediate acetonitrile stream comprising less than 1 wt. % hydrogen cyanide,

purifying the intermediate acetonitrile stream in a pressure swing distillation system to produce an acetonitrile product stream and a recycle stream,

purifying the acetonitrile product stream to form a purified acetonitrile product stream comprising at least 98 wt. % acetonitrile,

wherein the first distillation column operates at a pressure greater than 0 psig.

2. The process of claim 1 , wherein the pressure swing distillation system comprises:

a low pressure distillation column and a high pressure distillation column and wherein the high pressure distillation column yields an overhead stream and a bottoms stream.

3. The process of claim 2 , wherein the recycle stream is the overhead stream of the high pressure distillation column.

4. The process of claim 2 , wherein the acetonitrile product stream is the bottoms stream of the high pressure distillation column.

5. 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 intermediate acetonitrile stream comprises less than 0.01 wt. % hydrogen cyanide, and wherein the purified acetonitrile product stream comprises at least 99.5 wt. % acetonitrile.

6. The process of claim 1 , further comprising the step of:

recycling the recycle stream, which comprises methanol, to the first distillation column.

7. The process of claim 1 , wherein the recycle stream comprises at least 0.01 wt. % methanol.

8. The process of claim 1 , wherein the recycle stream comprises from 0.01 wt. % to 5 wt. % methanol.

9. The process of claim 1 , wherein the purifying of the acetonitrile product stream comprises distilling the acetonitrile product stream to yield the purified acetonitrile product stream.

10. The process of claim 1 , wherein the feedstock stream comprises at least 0.05 wt. % methanol.

11. The process of claim 1 , wherein the feedstock stream comprises less than 5 wt. % acetonitrile.

12. The process of claim 1 , wherein the feedstock stream further comprises propionitrile.

13. The process of claim 1 , wherein the treating comprises reacting the crude acetonitrile stream with a caustic solution to react out hydrogen cyanide.

14. The process of claim 1 , wherein the crude acetonitrile stream comprises from 0.1 wt. % to 5 wt. % hydrogen cyanide.

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

16. The process of claim 1 , wherein the feedstock stream comprises one or more waste streams from acrylonitrile production processes.

17. The process of claim 2 , wherein the low pressure distillation column operates at a pressure less than −5 psig.

18. The process of claim 2 , wherein the high pressure distillation column operates at a pressure greater than 10 psig.

19. The process of claim 1 , wherein the purified acetonitrile product stream comprises at least 99.9 wt. % of acetonitrile.

20. The process of claim 1 , wherein the purified acetonitrile product stream comprises less than 0.1 wt. % of propionitrile.

21. A process for recovering acetonitrile, comprising the steps of:

distilling a feedstock stream comprising methanol and acetonitrile present in an amount equal to or less than 10 wt % in a first distillation column to yield a crude acetonitrile stream,

treating the crude acetonitrile stream to remove hydrogen cyanide and produce an intermediate acetonitrile stream comprising less than 1 wt. % hydrogen cyanide, and

purifying the intermediate acetonitrile stream in a pressure swing distillation system to produce a recycle stream and an acetontrile product stream comprising at least 90 wt. % acetonitrile,

wherein the first distillation column operates at a pressure greater than 0 psig.

22. The process of claim 1 , wherein the feedstock stream comprises from 0.01 wt. % to 1 wt. % methanol.

23. The process of claim 21 , wherein the feedstock stream comprises from 0.01 wt. % to 1 wt. % methanol.

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 Feb 5, 2020
From: MICHAEL, BASIL; DIAZ, CARL ALEXANDER; NELSON, BILLY; KISSELL, KYLE
To: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
Reel/Frame 051729/0626 →
Cited By (2)
US 12,577,198 US 12,643,071