Skeletal Copper Catalyst for 1,3-Butanediol Hydrogenation
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Solution Overview
Problem
The existing process for producing (R)-3-hydroxybutyl (R)-3-hydroxybutyrate uses sodium borohydride and other hydride transfer reagents, which are environmentally undesirable, and lacks effective catalysts and conditions for hydrogenation in the production of 1,3-butanediol, as described in WO 2014/140308.
Innovation Solution
A skeletal copper-based catalyst is used for hydrogenation to efficiently reduce the ester of poly-(R)-3-hydroxybutyrate to form (R)-1,3-butanediol, followed by transesterification with additional poly-(R)-3-hydroxybutyrate to produce (R)-3-hydroxybutyl (R)-3-hydroxybutyrate, offering a more effective and environmentally friendly method compared to using Raney nickel catalysts.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If sodium borohydride and hydride transfer reagents are used for reduction, then the reduction of poly-(R)-3-hydroxybutyrate ester to 1,3-butanediol can be achieved, but environmental harm increases due to undesirable reagent properties
Solution Approach 1:
The invention changes the chemical nature of the reducing agent from hydride transfer reagents (sodium borohydride) to hydrogen gas, fundamentally altering the reaction parameters and eliminating environmental harm associated with the former while maintaining reduction effectiveness
Solution Approach 2:
The invention converts the harmful environmental aspect of using sodium borohydride into a benefit by replacing it with hydrogen gas, which is environmentally benign and leaves no harmful residues, thus turning a harmful process into a green chemistry solution
2Reliability
If Raney nickel catalyst is used for hydrogenation, then hydrogenation reaction can proceed, but catalytic efficiency and selectivity are insufficient compared to skeletal copper-based catalysts
Solution Approach 1:
The invention changes the catalyst material from Raney nickel to skeletal copper-based catalyst, altering the catalytic properties to achieve higher efficiency and selectivity for the hydrogenation reaction while maintaining the hydrogenation capability
Solution Approach 2:
The skeletal copper-based catalyst represents a composite material structure that combines copper with a skeletal support matrix, providing enhanced catalytic performance compared to traditional Raney nickel catalysts
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
The skeletal copper-based catalyst significantly improves the production of 1,3-butanediol and (R)-3-hydroxybutyl (R)-3-hydroxybutyrate, achieving higher selectivity and efficiency while reducing environmental impact, as demonstrated by comparisons with Raney nickel catalysts in various reaction conditions.
Implementation Method 1
reducing the first portion of the poly-(R)-3-hydroxybutyrate ester through hydrogenation using a skeletal copper-based catalyst to form (R)-1,3-butanediol
Implementation Method 2
The skeletal copper-based catalyst significantly improves the production of 1,3-butanediol and (R)-3-hydroxybutyl (R)-3-hydroxybutyrate
Implementation Method 3
contacting under transesterification conditions the (R)-1,3-butanediol from step ii) with the second portion of the transesterified ester to produce (R)-3-hydroxybutyl (R)-3-hydroxybutyrate
Data Source
AI summary
A process is described for producing 1,3-butanediol, wherein an ester of poly-(R)-3-hydroxybutyrate such as formed by transesterification with an alcohol is reduced by hydrogenation in the presence of a skeletal copper-based catalyst to provide 1,3-butanediol. The 1,3-butanediol may be transesterified by reaction with additional poly-(R)-3-hydroxybutyrate ester to produce (R)-3-hydroxybutyl (R)-3-hydroxybutyrate.