Hydroformylation process

Patent metadata

Field	Value
Publication number	US-10407372-B2
Application number	US-201716081682-A
Country	US
Kind code	B2
Filing date	Mar 15, 2017
Priority date	Mar 18, 2016
Publication date	Sep 10, 2019
Grant date	Sep 10, 2019

Abstract

Embodiments of the present invention relate to processes for the hydroformylation of olefins to produce aldehydes. In some embodiments, processes of the present invention are capable of maintaining high C 2 -C 4 olefin conversion and/or provide more compact hydroformlyation processes.

First claim

What is claimed is:

1. A process comprising:
(a) contacting CO, H 2 , and at least one C 2 -C 4 olefin in a reaction zone in the presence of a hydroformylation catalyst to form at least one aldehyde product;
(b) removing an aldehyde-containing liquid from the reaction zone and sending it to a product-catalyst separation zone;
(c) transporting a first stream from the product-catalyst separation zone to the reaction zone, wherein the first stream is a liquid comprising at least a portion of the hydroformylation catalyst, at least a portion of the aldehyde product, and unreacted olefin;
(d) removing a second stream from the product-catalyst separation zone, wherein the second stream comprises at least a portion of the aldehyde product, unreacted olefin, and one or more paraffins;
(f) transferring the second stream to a syngas stripper wherein a gas comprising CO and H 2 separates the unreacted olefin from the aldehyde;
(g) providing the gas leaving the syngas stripper to a condenser to provide a second liquid comprising a majority of the aldehyde, at least a portion of the unreacted olefin from the syngas stripper, and at least a portion of the paraffins from the syngas stripper, and to provide a gas stream comprising CO, H 2 , the remainder of the unreacted olefin from the syngas stripper, and the remainder of the paraffins from the syngas stripper;
(h) providing the gas stream leaving the condenser in (g) to the reaction zone;
(i) transferring the second liquid from the condenser in (g) to a first distillation system wherein at least a portion of the unreacted olefin and paraffins are distilled from the aldehyde;
(j) transferring the gas from the first distillation system to a second distillation system wherein the unreacted olefin and paraffins are separated into an olefin-enriched stream and a paraffin-enriched stream, wherein the gas is transferred from the first distillation system to the second distillation system without a compressor; and
(k) transferring the olefin-enriched stream to the reaction zone.

2. The process of claim 1 , wherein the second stream from the product-catalyst separation zone is a liquid.

3. The process of claim 2 , wherein the product-catalyst separation zone comprises a membrane separation process.

4. The process of claim 1 , wherein the second stream from the product-catalyst separation zone is a vapor.

5. The process of claim 4 , wherein the product-catalyst separation zone comprises a vaporizer.

6. The process of claim 4 , wherein the product-catalyst separation zone comprises a vaporizing zone and a vapor/liquid separation zone, wherein the aldehyde-containing liquid from the reaction zone is heated in the vaporizing zone to generate the vapor, and wherein the vapor/liquid separation zone comprises a liquid withdrawal port, a liquid region, a vapor space and a vapor withdrawal port.

7. The process of claim 4 , further comprising condensing the second stream from the product-catalyst separation zone prior to transferring the second stream to the syngas stripper.

8. The process of claim 1 , wherein the rate of paraffin removal in step (j) is sufficient to prevent buildup of paraffin in the reaction zone.

9. The process of claim 1 , wherein the liquid from the condenser in (g) is transferred to the first distillation system with a pump.

10. The process of claim 1 , wherein the aldehyde from the first distillation system is returned to the syngas stripper.

11. A process comprising:
(a) contacting CO, H 2 , and at least one C 2 -C 4 olefin in a reaction zone in the presence of a hydroformylation catalyst to form at least one aldehyde product;
(b) removing an aldehyde-containing liquid from the reaction zone and sending it to a product-catalyst separation zone, wherein the product-catalyst separation zone comprises a liquid withdrawal port and a vapor withdrawal port;
(c) Transporting a liquid comprising at least a portion of the hydroformylation catalyst, at least a portion of the aldehyde product, and unreacted olefin from the liquid withdrawal port to the reaction zone;
(d) removing a vapor from the vapor withdrawal port, wherein the vapor comprises at least a portion of the aldehyde product, unreacted olefin, and one or more paraffins;
(e) condensing the vapor to generate a second liquid;
(f) transferring the second liquid to a syngas stripper wherein a gas comprising CO and H 2 separates the unreacted olefin from the aldehyde;
(g) providing the gas leaving the syngas stripper to a condenser to provide a second liquid comprising a majority of the aldehyde, at least a portion of the unreacted olefin from the syngas stripper, and at least a portion of the paraffins from the syngas stripper, and to provide a gas stream comprising CO, H 2 , the remainder of the unreacted olefin from the syngas stripper, and the remainder of the paraffins from the syngas stripper;
(h) providing the gas stream leaving the condenser in (g) to the reaction zone;
(i) transferring the second liquid from the condenser in (g) to a first distillation system wherein at least a portion of the unreacted olefin and paraffins are distilled from the aldehyde;
(j) transferring the gas from the first distillation system to a second distillation system wherein the unreacted olefin and paraffins are separated into an olefin-enriched stream and a paraffin-enriched stream, wherein the gas is transferred from the first distillation system to the second distillation system without a compressor; and
(k) transferring the olefin-enriched stream to the reaction zone.

12. The process of claim 11 , wherein the rate of paraffin removal in step (j) is sufficient to prevent buildup of paraffin in the reaction zone.

13. The process of claim 11 , wherein the second liquid from the condenser in (g) is transferred to the first distillation system with a pump.

14. The process of claim 1 , wherein the aldehyde from the first distillation system is returned to the syngas stripper.

15. The process of claim 1 , wherein transferring the olefin-enriched stream to the reaction zone comprises condensing the olefin-enriched stream and pumping the condensed olefin-enriched stream to the reaction zone.

16. The process of claim 1 , wherein the olefin-enriched stream in step (k) is transferred to the reaction zone as a gas without a compressor.

Assignees

• Dow Technology Investments Llc

Inventors

• Simpson Kathleen
• Smith Gerald L

Classifications

• C07C45/786

  by membrane separation process, e.g. pervaporation, perstraction, reverse osmosis · CPC title

• C07C45/72

  by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups · CPC title

• C07C45/50

  by oxo-reactions · CPC title

• C07C45/783

  by gas-liquid treatment, e.g. by gas-liquid absorption · CPC title

• C07C47/02

  Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen · CPC title