Heterocycle catalyzed carbonylation and hydroformylation with carbon dioxide

• US 8,568,581 B2
• Filed: 11/30/2011
• Issued: 10/29/2013
• Est. Priority Date: 11/30/2010
• Status: Active Grant

• Current Assignee: Avantium Knowledge Centre B.V. (Avantium NV)
• Original Assignee: Liquid Light, Inc. (Avantium NV)
• Inventors: Cole, Emily Barton, Teamey, Kyle, Sivasankar, Narayanappa
• Primary Examiner(s): Van, Luan
• Assistant Examiner(s): Chung, Ho-Sung
• Application Number:
  US13/307,980
• Publication Number:
  US 20120132537A1
• Time in Patent Office: 699 Days
• Field of Search: 205/448, 205/413, 205/440, 205/450
• US Class Current: 205/413
• CPC Class Codes: B01J 2231/321 Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
• CPC Class Codes: C25B 1/55 Photoelectrolysis
• CPC Class Codes: C25B 3/00 Electrolytic production of organic compounds
• CPC Class Codes: C25B 3/23 Oxidation halogenation C25B3/27
• CPC Class Codes: C25B 3/25 Reduction

Abstract

Methods and systems for heterocycle catalyzed carbonylation and hydroformylation with carbon dioxide are disclosed. A method may include, but is not limited to, steps (A) to (D). Step (A) may introduce water to a first compartment of an electrochemical cell. The first compartment may include an anode. Step (B) may introduce carbon dioxide to a second compartment of the electrochemical cell. The second compartment may include a solution of an electrolyte, a heterocyclic catalyst, and a cathode. Step (C) may introduce a second reactant to the second compartment of the electrochemical cell. Step (D) may apply an electrical potential between the anode and the cathode in the electrochemical cell sufficient to induce liquid phase carbonylation or hydroformylation to form a product mixture.

Claims

1. A method for hydroformylation with carbon dioxide, comprising:

(A) introducing water to a first compartment of an electrochemical cell, said first compartment including an anode;

(B) introducing carbon dioxide to a second compartment of said electrochemical cell, said second compartment including a solution of an electrolyte, a heterocyclic catalyst, and a cathode;

(C) introducing an alkene to said second compartment of said electrochemical cell; and

(D) applying an electrical potential between said anode and said cathode in said electrochemical cell sufficient for said cathode to induce liquid phase hydroformylation to form a product mixture.

2. The method of claim 1, wherein said product mixture includes at least one of a carboxylic acid, an aldehyde, or an alcohol.

3. The method of claim 1, wherein said solution of said electrolyte includes at least one of potassium chloride or potassium sulfate.

4. The method of claim 1, where said heterocyclic catalyst includes at least one of imidazole, pyridine, or a substituted variant of imidazole or pyridine, said substituted variant including at least one of a five member heterocyclic ring or a six member heterocyclic ring.

5. The method of claim 1, wherein said second compartment further includes a metal oxide reaction promoter.

6. The method of claim 1, wherein said alkene includes at least one of ethylene, propylene, 1-butylene, 2-butylene, butadiene, an unsaturated alcohol, or an unsaturated organic reactant.

7. The method of claim 1, wherein applying an electrical potential between said anode and said cathode in said electrochemical cell includes:

applying a potential of between approximately −

0.5 and −

2V vs. SCE (saturated calomel electrode) at said cathode.

8. The method of claim 1, wherein applying an electrical potential between said anode and said cathode in said electrochemical cell includes:

applying an electrical potential between said anode and said cathode in said electrochemical cell at ambient temperature and pressure.

9. The method of claim 1, wherein said second compartment further includes at least one percent water of a total amount of liquid in said second compartment.