Azeotropic distillation of hydroxyacetic acid

• US 4,431,486 A
• Filed: 04/12/1982
• Issued: 02/14/1984
• Est. Priority Date: 04/12/1982
• Status: Expired due to Term

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Balmat, Jean L.
• Primary Examiner(s): Sever, Frank
• Application Number:
  US06/367,753
• Time in Patent Office: 673 Days
• Field of Search: 562/518, 562/577, 562/579, 562/580, 203/28, 203/34, 203/35, 203/69, 203/DIG. 6
• US Class Current: 203/69
• 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
• CPC Class Codes: Y02P 20/584 Recycling of catalysts

Abstract

The yield of hydroxyacetic acid produced from formaldehyde, water and carbon monoxide in the presence of a sulfuric acid catalyst and using crude recycled hydroxyacetic acid as the reaction medium is improved by azeotropic distillation of crude, recycle hydroxyacetic acid with toluene. The distillation step reduces the water content of feed thereby increases conversion of formaldehyde to hydroxyacetic acid and reduces formic acid content in the product.

Claims

1. In a process for the production of hydroxyacetic acid from formaldehyde, water and carbon monoxide in the presence of a sulfuric acid catalyst using crude, recycled hydroxyacetic acid as a reaction medium the improvement comprising an azeotropic distillation with essentially a single aromatic hydrocarbon of the crude hydroxyacetic acid to be recycled as reaction medium in amounts sufficient to cause an azeotrope with said hydroxyacetic acid.

2. A process of claim 1 wherein the aromatic hydrocarbon is toluene.

3. In a process for the production of hydroxyacetic acid from formaldehyde, water and carbon monoxide in the presence of a sulfuric acid catalyst using crude hydroxyacetic acid as a reaction medium the improvement comprising an azeotropic distillation with an aromatic hydrocarbon consisting essentially of toluene of the crude hydroxyacetic acid to be recycled as reaction medium in amounts sufficient to cause an azeotrope with said hydroxyacetic acid and a molar ratio of water to formaldehyde feed mix is 1.3 to 1 to 1.5 to 1.