Process for the carbonylation of formaldehyde

• US 6,376,723 B2
• Filed: 12/18/2000
• Issued: 04/23/2002
• Est. Priority Date: 12/29/1999
• Status: Expired due to Fees

• Current Assignee: Shell Oil Company (Shell Plc)
• Original Assignee: Shell Oil Company (Shell Plc)
• Inventors: Mul, Wilhelmus Petrus, Drent, Eit, Ruisch, Bart Johan
• Primary Examiner(s): Padmanabhan, Sreeni
• Assistant Examiner(s): Price, Elvis O.
• Application Number:
  US09/739,172
• Publication Number:
  US 20010039364A1
• Time in Patent Office: 491 Days
• Field of Search: 568/864, 568/861, 560/179, 560/129
• US Class Current: 568/864
• CPC Class Codes: C07C 29/149 with hydrogen or hydrogen-containing gases
• CPC Class Codes: C07C 31/202 Ethylene glycol
• CPC Class Codes: C07C 51/12 on an oxygen-containing group in organic compounds, e.g. alcohols
• CPC Class Codes: C07C 59/06 Glycolic acid

Abstract

A carbonylation process, wherein formaldehyde or a derivative thereof is reacted with carbon monoxide in the presence of a catalyst composition including:

a) an acidic compound with pKa value below −1, and

b) a sulfone.

Claims

1. A carbonylation process wherein formaldehyde or a derivative thereof is reacted with carbon monoxide in the presence of a catalyst composition comprising:

a) an acidic compound with pKa value below −

1; and

b) a sulfone.

2. The process of claim 1 wherein the derivative of formaldehyde is paraformaldehyde.

3. The process of claim 1 wherein the sulfone is according to the formula

4. The process of claim 1 wherein the acidic compound is an homogeneous acid.

5. The process of claim 4 wherein the acidic compound is of the R—

SO₃H type, wherein R represents a halogenated alkyl or an halogenated aromatic group.

6. The process of claim 1 wherein the acidic compound is an heterogeneous acid.

7. The process of claim 6 wherein the heterogeneous acid is a strongly acidic ion exchange resin.

8. The process of claim 1 wherein also water is present in a concentration of less than 30% (w/w) based on the total weight of sulfone and water.

9. The process of claim 1 wherein the molar ratio of acidic compound to equivalents of monomer formaldehyde or a derivative thereof is in the range of 1:

100 to 10;

1.

10. A process for producing ethylene glycol comprising:

a) carbonylating formaldehyde or a derivative thereof with carbon monoxide according to the process of claim 1 to produce glycolic acid or polyglycolic acid;

b) esterification of the (poly) glycolic acid with methanol to produce methyl glycolate; and

c) hydrogenation of the methyl glycolate to produce ethylene glycol.

11. The process of claim 10 wherein the derivative of formaldehyde is paraformaldehyde.

12. The process of claim 10 wherein the sulfone is according to the formula

13. The process of claim 12 wherein the acidic compound is an homogeneous acid.

14. The process of claim 12 wherein the acidic compound is an heterogeneous acid.

15. The process of claim 10 wherein the molar ratio of acidic compound to equivalent of monomer formaldehyde or a derivative thereof is in the range of 1:

100 to 10;

1.