Preparation of sulfate free glycolic acid ester

• US 4,140,866 A
• Filed: 03/30/1978
• Issued: 02/20/1979
• Est. Priority Date: 03/30/1978
• Status: Expired due to Term

• Current Assignee: PPG Industries Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Incorporated (Nouryon BV)
• Inventors: Nielsen, Donald R.
• Primary Examiner(s): Evans, Joseph E.
• Application Number:
  US05/891,964
• Time in Patent Office: 327 Days
• Field of Search: 560/189, 568/864
• 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 67/60 by treatment giving rise to chemical modification by chemisorption C07C67/56
• CPC Class Codes: C07C 69/675 of saturated hydroxy-carboxylic acids

Abstract

Sulfate is removed from glycolic acid, prepared by the sulfuric acid catalyzed carbonylation of formaldehyde and intended for use as an intermediate in the production of ethylene glycol by catalytic hydrogenation by treating the glycolic acid with alkali metal hydroxide or carbonate, and esterifying the glycolic acid; the alkali metal sulfate being substantially completely precipitated in and separated from the esterification product.

Claims

1. A process for preparing substantially sulfate free glycolic acid ester from sulfuric acid containing glycolic acid comprising treating said glycolic acid with alkali metal hydroxide or carbonate to convert sulfuric acid contained therein to soluble alkali metal sulfate, esterifying the so-treated glycolic acid so as to precipitate alkali metal sulfate from the esterified glycolic acid.

2. The process of claim 1 wherein the alkali metal hydroxide or carbonate is selected from sodium hydroxide, potassium hydroxide, sodium carbonate, or potassium carbonate.

3. The process of claim 1 wherein the acid number of the esterified glycolic acid is less than 1.0 milliequivalent H⁺ per gram.

4. The process of claim 3 wherein the acid number of the esterified glycolic acid is less than 0.2 milliequivalent H⁺ per gram.

5. The process of claim 1 wherein the glycolic acid is esterified in the presence of ethylene glycol.

6. The process of claim 5 wherein the glycolic acid is mixed with ethylene glycol prior to converting the sulfuric acid to alkali metal sulfate.

7. In a process for preparing ethylene glycol by the liquid phase catalytic hydrogenation of glycolic acid ester prepared by esterifying glycolic acid that had been prepared by the sulfuric acid catalyzed liquid phase carbonylation of formaldehyde, the improvement comprising treating the crude glycolic acid obtained from the sulfuric acid catalyzed carbonylation of formaldehyde with alkali metal hydroxide or carbonate to convert the sulfuric acid contained in the glycolic acid to soluble alkali metal sulfate and esterifying the glycolic acid containing the dissolved alkali metal sulfate so as to precipitate alkali metal sulfate and separating the precipitated alkali metal sulfate from the esterification product prior to subjecting the esterification product to catalytic liquid phase hydrogenation.

8. The process of claim 7 wherein the alkali metal hydroxide or carbonate is selected from sodium hydroxide, potassium hydroxide, sodium carbonate, or potassium carbonate.

9. The process of claim 7 wherein the acid number of the esterified glycolic acid is less than 1.0 milliequivalent H⁺ per gram.

10. The process of claim 9 wherein the acid number of the esterified glycolic acid is less than 0.2 milliequivalent H⁺ per gram.

11. The process of claim 7 wherein the glycolic acid is esterified in the presence of ethylene glycol.

12. The process of claim 11 wherein the glycolic acid is mixed with the ethylene glycol prior to converting the sulfuric acid to alkali metal sulfate.