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

A hydrogenation catalyst and selective technology, applied in the preparation of organic compounds, the preparation of carbon-based compounds, chemical instruments and methods, etc., can solve the problems of reduction of manufacturing cost, degree of commercial feasibility, etc., and achieve overall economic improvement and increase The effect of effective utilization

Active Publication Date: 2021-11-09
ARCHER DANIELS MIDLAND CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Progress in ongoing efforts to replace fossil-sourced chemicals with their renewable carbon counterparts will therefore be highly dependent on improvements in upstream processing efficiencies, in particular through increased reaction selectivity, intermediate and final product quality, and / or composition. improved separability, all of which have the potential to reduce manufacturing costs to commercially viable levels

Method used

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

Examples

Experimental program
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Effect test

example 1

[0065] Hydrogenation of furfural

[0066] A liquid mixture of 24 grams of furfural and 62 grams of methanol solvent was charged to a 300-cc high pressure reactor (Parr Instrument Company). To this mixture was added 2.05 g of a granular solid catalyst on a carbon support with a metal content of 2% by weight Ru / 2% by weight Sn / 0.5% by weight Pt. The reactor was purged with hydrogen while stirring the reaction mixture continuously at 800 rpm. Thereafter, the reactor was pressurized to 8.3 MPa (1200 psi) with hydrogen, and the reaction mixture was heated to 65° C. and held at this temperature for 1 hour. The reaction mixture was then cooled to room temperature and the reactor was opened. The solid and liquid contents were removed from the reactor and filtered by vacuum filtration to isolate the catalyst. The filtrate was rotavaped to remove the methanol solvent. The composition of the remaining liquid was analyzed using nuclear magnetic resonance (NMR) spectroscopy, and foun...

example 2

[0069] Selective Hydrogenation of Methylglyoxal

[0070] A liquid composition of 15.1 g of methylglyoxal concentrated to 40% by weight in water was added to 86 ml of water, and the resulting mixture was charged to a 300-cc high pressure reactor (Parr Instruments). To this mixture was added 1.96 g of a granular solid catalyst on a carbon support with a metal content of 2% by weight Ru / 2% by weight Sn / 0.5% by weight Pt. The reactor was purged with hydrogen while stirring the reaction mixture continuously at 800 rpm. Thereafter, the reactor was pressurized to 8.3 MPa (1200 psi) with hydrogen, and the reaction mixture was heated to 65° C. and held at this temperature for 1 hour. The reaction mixture was then cooled to room temperature and the reactor was opened. The solid and liquid contents were removed from the reactor and filtered by vacuum filtration to isolate the catalyst. The composition of the filtrate was analyzed using NMR spectroscopy and found to contain a major p...

example 3

[0073] Selective hydrogenation of glyoxal

[0074] A liquid composition of 15.1 g of glyoxal concentrated to 40% by weight in water was added to 85 ml of water, and the resulting mixture was charged to a 300-cc high pressure reactor (Parr Instruments). To this mixture was added 2.17 g of a granular solid catalyst on a carbon support with a metal content of 2% by weight Ru / 2% by weight Sn / 0.5% by weight Pt. The reactor was purged with hydrogen while stirring the reaction mixture continuously at 800 rpm. Thereafter, the reactor was pressurized to 8.3 MPa (1200 psi) with hydrogen, and the reaction mixture was heated to 60° C. and held at this temperature for 1 hour. The reaction mixture was then cooled to room temperature and the reactor was opened. The solid and liquid contents were removed from the reactor and filtered by vacuum filtration to isolate the catalyst. The composition of the filtrate was analyzed using NMR spectroscopy and found to contain glycolaldehyde (14% b...

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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.

Description

technical field [0001] One aspect of the present invention relates to methods and catalysts for the selective hydrogenation of compounds having at least two carbonyl carbon atoms, which may be aldehyde and / or ketone carbon atoms. In another aspect, the present invention relates to methods and catalysts for increasing the amount of selectively hydrogenated analogs, such as selectively hydrogenated glycolaldehyde from glyoxal, both initially Both may be present in impure feed. Background technique [0002] The long-term trend of increasing costs for many hydrocarbon feedstocks has created a major drive to find alternative sources of petroleum-based carbon for the production of many important and valuable chemical products. Biomass (material derived from living or recently living organisms) is viewed as a readily available, inexpensive, renewable, non-petroleum-based supply of carbon from which many of these known, high-value chemicals are derived . The ability to convert bi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K3/00B01D3/00
CPCB01D3/346B01D3/40C07D307/48C07C45/64C07F19/00C07B41/02C07C49/17C07C47/19C07D307/42
Inventor 詹姆斯·布拉兹迪尔马志成
Owner ARCHER DANIELS MIDLAND CO