Processes and catalysts for the selective hydrogenation of compounds having carbonyl carbon atoms

Patent metadata

Field	Value
Publication number	US-12065417-B2
Application number	US-202017421492-A
Country	US
Kind code	B2
Filing date	Jan 9, 2020
Priority date	Jan 11, 2019
Publication date	Aug 20, 2024
Grant date	Aug 20, 2024

Abstract

Selective hydrogenation processes are disclosed that can upgrade impure feeds, such as those obtained from biomass and containing a number of small (e.g., 2-6 carbon atom) molecules having aldehyde and/or ketone carbon atoms. For example, whereas glycolaldehyde and its methylated derivative, hydroxyacetone (acetol) are both high value intermediates for certain downstream processing reactions, they are normally recovered in a condensate from pyrolysis of carbohydrates (e.g., aldose-containing sugars) together with glyoxal and its methylated derivative, pyruvaldehyde. The selective hydrogenation of these compounds bearing two carbonyl carbon atoms, without over-hydrogenation to ethylene glycol and propylene glycol, can increase the concentration of the desired intermediates. These beneficial effects of selective hydrogenation may be achieved through the use of a hydrogenation catalyst comprising noble metals such as Ru and Pt.

First claim

What is claimed is:

1. A method for increasing the amount of glycolaldehyde present in an impure feed comprising glyoxal, pyruvaldehyde, glycolaldehyde, and hydroxyacetone (acetol), the method comprising contacting the impure feed with a hydrogenation catalyst under hydrogenation conditions, to selectively hydrogenate at least a portion of the glyoxal to form a product having an increased amount of glycolaldehyde.

2. The method of claim 1 , wherein the contacting under hydrogenation conditions selectively hydrogenates at least a portion of the pyruvaldehyde to form an increased amount of hydroxyacetone in the product, together with the increased amount of glycolaldehyde.

3. A method for producing glycolaldehyde and/or hydroxyacetone (acetol), the method comprising:
pyrolyzing an aqueous solution of an aldose-containing sugar in a pyrolysis reactor under pyrolysis conditions, including elevated temperature, to provide a vapor phase pyrolysis product comprising thermal decomposition products of the aldose-containing sugar;
cooling said vapor phase pyrolysis product to condense a liquid mixture comprising glyoxal, pyruvaldehyde, glycolaldehyde, and hydroxyacetone (acetol);
contacting the liquid mixture with a hydrogenation catalyst under hydrogenation conditions, to selectively hydrogenate (i) at least a portion of the glyoxal, (ii) at least a portion of the pyruvaldehyde, or (iii) both (i) and (ii) to form a product having respectively, (i) an increased amount of glycolaldehyde, (ii) an increased amount of hydroxyacetone (acetol), or (iii) both (i) and (ii); and
distilling the product to recover a fraction that is enriched in, respectively, (i) glycolaldehyde, (ii) hydroxyacetone (acetol), or (iii) both (i) and (ii).

Assignees

• Archer Daniels Midland Co

Inventors

• Brazdil James
• Ma chi-cheng

Classifications

• C07C45/64

  by introduction of functional groups containing oxygen only in singly bound form · CPC title

• B01D3/40

  Extractive distillation · CPC title

• C07B41/02

  of hydroxy or O-metal groups · CPC title

• C07F19/00

  Metal compounds according to more than one of main groups C07F1/00 - C07F17/00 · CPC title

• C07D307/48

  Furfural · CPC title