IP Library Granted Patent US 9,340,480
Granted Patent B2
US 9,340,480 · App. 14/782,694 · Granted May 17, 2016

Aldehyde production process with multi-stage condensation

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Quick Facts
Patent No.
US 9,340,480
App. No.
14/782,694
Granted
May 17, 2016
Kind
B2
Abstract

A hydroformylation system for making aldehyde by reacting olefin with synthesis gas by way of hydroformylation is improved by multi-stage condensation of gaseous reactor effluent for providing liquid feed to a gas-liquid contact zone. The process provides for condensing and separating the gaseous reactor output stream in a plurality of successive condenser stages into gaseous condenser output streams and liquid condenser output streams having differing temperatures and feeding the recovered liquid to the gas-liquid contact zone to improve olefin recovery by stripping.

Claims (27)

1. A method of recovering a crude aldehyde product stream from a gaseous stream containing aldehyde and unreacted olefin from a hydroformylation system comprising:

(a) condensing and separating the gaseous stream in a first condenser stage into (i) a first condenser stage liquid product stream at a first temperature and (ii) a first condenser stage gaseous output stream;

(b) condensing and separating at least a portion of the first condenser stage gaseous output stream in a second condenser stage into (i) a second condenser stage liquid product stream at a second temperature lower than said first temperature of said first condenser stage liquid stream and (ii) a second condenser stage gaseous output stream;

(c) feeding at least both of the first condenser stage liquid stream and the second condenser stage liquid stream as liquid feed to a gas-liquid contact zone in order to adjust a liquid feed temperature to the gas-liquid contact zone;

(d) stripping unreacted olefin from the liquid feed with synthesis gas in said gas-liquid contact zone; and

(e) recovering a crude liquid aldehyde product stream from said gas-liquid contact zone having a lower olefin content than the liquid feed to said gas-liquid contact zone.

2. The method according to claim 1 , wherein the liquid feed temperature to the gas-liquid contact zone is at a temperature intermediate the first temperature of the first condenser stage product stream and the second temperature of the second condenser stage product stream.

3. The method according to claim 1 , wherein said first condenser stage liquid stream and said second condenser stage liquid stream are combined prior to providing them to the gas-liquid contact zone.

4. The method according to claim 1 , wherein the liquid feed temperature is between 68° C. and 85° C.

5. The method according to claim 1 , wherein the first condenser stage liquid stream is at a temperature of from 70° C. to 105° C.

6. The method according to claim 1 , wherein the second condenser stage liquid stream is at a temperature of from 50° C. to 70° C.

7. The method according to claim 1 , wherein the first condenser stage liquid stream and the second condenser stage liquid stream are supplied to the gas-liquid contact zone without external heating.

8. The method according to claim 1 , wherein the ratio of unreacted olefin to aldehyde in the crude liquid aldehyde product stream is less than 1 g olefin/kg aldehyde.

9. Apparatus for recovering a crude aldehyde product stream from a gaseous stream containing aldehyde and unreacted olefin withdrawn from a hydroformylation reactor comprising:

(a) a plurality of successive condenser stages including a first and last condenser stage, each of which condenser stages is adapted for condensing and separating the gaseous stream into a liquid product stream and a gaseous output stream thereby generating a (i) a plurality of staged liquid product streams at successively lower temperatures and (ii) a plurality of staged gaseous output streams at successively lower temperatures;

(b) a gas-liquid contact zone ducted directly to said plurality of staged liquid product streams in order to receive said plurality of staged liquid product streams in order to adjust a liquid feed temperature to said gas-liquid contact zone, said gas-liquid contact zone being configured and adapted to strip unreacted olefin from the liquid feed with synthesis gas in said gas-liquid contact zone as well as provide a crude liquid aldehyde product stream from said gas liquid contact zone having a lower olefin content than the liquid feed.

10. The apparatus according to claim 9 , wherein the liquid feed temperature to said gas-liquid contact zone is at a temperature below a temperature of the first condenser stage liquid product stream and above a temperature of the last condenser stage liquid product stream.

11. The apparatus according to claim 9 , wherein said plurality of successive condenser stages consists of two successive condenser stages.

12. The apparatus according to claim 9 , wherein said plurality of successive condenser stages consists of three successive condenser stages.

13. The apparatus according to claim 9 , wherein said plurality of successive condenser stages consists of four successive condenser stages.

14. The method according to claim 1 , wherein the olefin is propylene and the aldehyde product is butyraldehyde.

15. The method according to claim 2 , wherein the olefin is propylene and the aldehyde product is butyraldehyde.

16. The method according to claim 3 , wherein the olefin is propylene and the aldehyde product is butyraldehyde.

17. The method according to claim 4 , wherein the olefin is propylene and the aldehyde product is butyraldehyde.

18. The method according to claim 1 , wherein the olefin is ethylene and the aldehyde product is propionaldehyde.

19. The method according to claim 2 , wherein the olefin is ethylene and the aldehyde product is propionaldehyde.

20. The method according to claim 3 , wherein the olefin is ethylene and the aldehyde product is propionaldehyde.

Assignments (5)
TERMINATION AND RELEASE OF PATENT SECURITY AGREEMENT [RECORDED ON JUNE 21, 2024 AT REEL 067806, FRAME 0536] Recorded Apr 8, 2025
From: CANTOR FITZGERALD SECURITIES [AS THE COLLATERAL AGENT]
To: OQ CHEMICALS CORPORATION; OQ CHEMICALS BISHOP, LLC
Reel/Frame 070773/0022 →
PATENT SECURITY AGREEMENT Recorded Jun 21, 2024
From: OQ CHEMICALS CORPORATION; OQ CHEMICALS BISHOP, LLC
To: CANTOR FITZGERALD SECURITIES, AS COLLATERAL AGENT
Reel/Frame 067806/0536 →
CORRECTIVE ASSIGNMENT TO CORRECT THE 15375 MEMORIAL DRIVESUITE 300HOUSTON, TEXAS 77079USA PREVIOUSLY RECORDED ON REEL 057091 FRAME 0179. ASSIGNOR(S) HEREBY CONFIRMS THE OQ CHEMICALS CORPORATION. Recorded Aug 26, 2021
From: OXEA CORPORATION
To: OQ CHEMICALS CORPORATION
Reel/Frame 057438/0686 →
CHANGE OF NAME Recorded Jul 29, 2021
From: OXEA CORPORATION
To: OQ CHEMICALS CORPORATION
Reel/Frame 057091/0179 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 7, 2015
From: HEUWES, MARKUS; SHAH, BAKULESH N.
To: OXEA CORPORATION
Reel/Frame 036815/0394 →