Process for removing formaldehyde from a composition comprising glycolaldehyde

Patent metadata

Field	Value
Publication number	US-9796649-B2
Application number	US-201414769161-A
Country	US
Kind code	B2
Filing date	Feb 25, 2014
Priority date	Feb 27, 2013
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

A process for reducing the percentage by weight of formaldehyde present in a composition comprising glycolaldehyde, wherein formaldehyde is transformed into one or more formaldehyde acetal(s) and removed from the reactive distillation reaction solution by reactive distillation in the presence of at least one alcohol and a catalyst.

First claim

The invention claimed is:

1. A process for reducing the percentage by weight of formaldehyde present in a composition, comprising:
a) mixing an aqueous feed composition comprising glycoaldehyde at a first concentration and formaldehyde with an alcohol in a volume ratio of 1:9 to 9:1 to obtain a reactive distillation reaction solution;
b) contacting the reactive distillation reaction solution with an acid catalyst while distilling formaldehyde acetal produced in the reactive distillation to obtain a reactive distillation product solution; and
c) contacting the reactive distillation product solution with an acid catalyst while distilling excess alcohol from the reactive distillation product solution to obtain a final product solution comprising aqueous glycolaldehyde having a concentration greater than said first concentration.

2. A process according to claim 1 , wherein the alcohol is selected from one or more of the group consisting of methanol, ethanol, ethylene glycol and propylene glycol.

3. A process according to claim 1 , wherein the acid catalyst is selected from one or more of the group consisting of a solid catalyst, mineral acid catalyst and organic acid.

4. A process according to claim 1 , wherein the acid catalyst is selected from one or more of the group consisting of an acidic resin, molecular sieves and a mineral acid.

5. A process according to claim 1 , wherein the acid catalyst is selected from one or more of the group consisting of Brønsted acidic resins and concentrated sulphuric acid.

6. A process according to claim 1 , wherein the distillation is carried out at a temperature less than 120° C.

7. A process according to claim 1 , wherein the distillation is carried out under reduced pressure.

8. A process according to claim 1 , further comprising adding water to the reaction solution after reactive distillation, heating and reducing the volume of the solution.

9. A process according to claim 1 , wherein the feed composition comprising glycolaldehyde is obtained by pyrolysis of organic matter selected from the group consisting of biomass, wood and sugars.

10. A process according to claim 1 , wherein the feed composition comprising glycolaldehyde is obtained by pyrolysis of one or more sugars selected from the group consisting of glucose, sucrose, xylose, fructose and galactose.

11. A process according to claim 1 , wherein the feed composition comprising glycolaldehyde is obtained by hydroformylation.

12. A process for the preparation of ethylene glycol, comprising subjecting the final product solution prepared according to claim 1 to hydrogenation.

13. A process for the preparation of amines wherein the product solution composition comprising glycolaldehyde according to claim 1 is reductively aminated.

14. A process for preparing straight and branched chain oxygenated C4-alkyl and C4-alkenyl compounds, comprising: providing the final product solution according to claim 1 , and converting the glycolaldehyde to straight and branched chain oxygenated C4-alkyl and C4-alkenyl compounds.

15. A process for reducing the formaldehyde content of a glycolaldehyde composition, comprising:
a) mixing an aqueous feed composition comprising at least 8.5 wt. % glycolaldehyde with an alcohol in a volume ratio of 1:9 to 9:1 to obtain a reactive distillation reaction solution;
b) contacting the reactive distillation reaction solution with an acid catalyst while distilling formaldehyde acetal produced in the reactive distillation to obtain a reactive distillation product solution; and
c) contacting the reactive distillation product solution with an acid catalyst while distilling excess alcohol from the reactive distillation product solution to obtain a final product solution comprising glycolaldehyde having a concentration greater than that of said aqueous feed.

Assignees

• Haldor Topsoe As
• Haldor Topsoe As

Inventors

• Taarning Esben
• Holm Martin Spangsberg

Classifications

• C07C45/85 Primary

  by treatment giving rise to a chemical modification (by chemisorption C07C45/79) · CPC title

• C07C29/143

  of ketones · CPC title

• Y02P20/127

  Cross-Sectional Technologies · mapped topic

• A23V2002/00

  Food compositions, function of food ingredients or processes for food or foodstuffs · CPC title

• C07H3/02

  Monosaccharides · CPC title