Noble Metal Catalyst on Alkaline Support for BDO Oxidation

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Solution Overview

Problem

Current methods for catalytic oxidation of but-3-ene-1,2-diol (BDO) are inefficient in terms of reaction time and selectivity, and often require pH adjustment and subsequent salt neutralization, leading to unwanted saline effluents.

Innovation Solution

A two-step process using a catalyst with a noble metal active phase, such as palladium, supported on an alkaline material like hydrotalcite, which eliminates the need for pH adjustment and reduces salt formation, achieving high conversion efficiency and selectivity for vinyl keto acids, alcohols, and aldehydes, followed by addition of methyl mercaptan to produce bioavailable methionine compounds.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional oxidation methods are used, then the reaction can proceed, but the reaction time is long and selectivity is poor

Engineering Contradiction:
Improvereaction efficiencyVSAvoidreaction time
Core Design Contradiction:
ProductivityVSLoss of time

Solution Approach 1:

The patent changes the chemical parameters of the reaction system by introducing a specific catalyst system (noble metal on basic support) and controlling pH conditions, which transforms the reaction kinetics and selectivity, achieving high conversion efficiency and product selectivity within reduced timeframes

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces a catalyst as an intermediary substance (noble metal particles supported on basic materials) that mediates the oxidation reaction, providing an alternative reaction pathway with lower activation energy and improved selectivity toward desired products

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If pH adjustment is performed, then reaction conditions can be optimized, but salt formation occurs requiring neutralization and generating saline effluents

Engineering Contradiction:
Improvereaction controlVSAvoidsaline effluents
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The patent employs a basic support material that provides inherent pH control capabilities, allowing the reaction system to self-regulate pH conditions without requiring external base addition, thereby preventing salt formation and eliminating the need for neutralization steps

Inventive Principle:
Principle #25Self-service

Solution Approach 2:

The patent extracts the pH adjustment function from the conventional process by incorporating basic sites directly into the support structure, removing the need for separate pH adjustment and neutralization operations that generate harmful saline waste

Inventive Principle:
Principle #2Taking out (Extraction)

3Productivity

If conversion efficiency is increased, then more product is obtained, but selectivity may decrease leading to more byproducts

Engineering Contradiction:
Improveconversion efficiencyVSAvoidselectivity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent creates local active sites with specific electronic and geometric properties on the catalyst surface, where noble metal particles interact with the basic support to generate unique local environments that favor selective oxidation pathways while maintaining high conversion rates

Inventive Principle:
Principle #3Local quality

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

This process significantly improves reaction efficiency and selectivity, reduces reaction time, and eliminates the need for pH adjustment and salt formation, resulting in high yields of bioavailable methionine compounds like 2-oxo-4-methylthiobutanoic acid, 4-methylthio-2-oxo-butanol, and 2-oxo-4-methylthiobutanal, with recyclable catalysts maintaining performance.

Implementation Method 1

the catalytic oxidation of but-3-ene-1,2-diol (BDO)... oxidation of BDO carried out in the presence of a catalyst, said catalyst comprising an active phase based on at least one noble metal selected from palladium, gold, silver, platinum, rhodium, osmium, ruthenium and iridium

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

a support containing alkaline sites... the process of the invention allows eliminating any adjustment of the pH of the reaction medium and thus avoiding adding a base to the reaction medium

Methodology Applied
Scientific EffectBase catalysis: Catalysis

Data Source

PatentUS10442760B2Catalytic oxidation of but-3-ene-1,2-diol
Publication Date: 2019.10.15 ADISSEO FRANCE SAS
  • US10442760B2 patent drawing
  • US10442760B2 patent drawing
  • US10442760B2 patent drawing

AI summary

The invention concerns a synthesis process of a compound of the following formula (I) or one of the salts thereof,wherein R represents a COOH, CH2OH or CHO group,comprising the step according to which the but-3-ene-1,2-diol (BDO) is subjected to an oxidation in the presence of a catalyst, said catalyst comprising an active phase based on at least one noble metal selected from palladium, gold, silver, platinum, rhodium, osmium, ruthenium and iridium, and a support containing alkaline sites.The invention also concerns the application of this reaction to the preparation of bioavailable compounds of methionine used, in particular, in animal nutrition.