Two-Step Hydrogenation of Dicarboxylic Acids to Diols
Solution Overview
Problem
Current methods for converting biomass-derived carboxylic acids into valuable monomers, such as diols, are inefficient and lack environmentally benign processes, hindering the transition from petrochemical to bio-derived polymers.
Innovation Solution
A two-step process involving the hydrogenation of C4 to C7 dicarboxylic acids using heterogeneous catalysts at specific temperatures and pressures to form lactones, which are then converted into diols, optimizing conditions for high selectivity and yield.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If conventional fermentation methods are used to produce carboxylic acids from biomass, then production capacity is achieved, but efficient transformation into valuable monomers like diols is lacking
Solution Approach 1:
The transformation process is divided into two distinct catalytic hydrogenation steps: first converting carboxylic acids to lactones, then converting lactones to diols. This segmentation allows each step to be optimized independently with specific catalysts and conditions, improving overall transformation efficiency from biomass-derived acids to valuable diol monomers.
Solution Approach 2:
Lactones are introduced as intermediate compounds in the transformation pathway from carboxylic acids to diols. This intermediary approach enables controlled conversion through stable intermediates, facilitating efficient monomer synthesis while maintaining process control and selectivity.
2Speed
If high temperature and pressure conditions are applied for hydrogenation, then reaction rate increases, but selectivity and yield may decrease
Solution Approach 1:
The patent employs dynamic adjustment of temperature and pressure conditions for each hydrogenation step. The first step (acid to lactone) uses specific T1/P1 conditions optimized for that transformation, while the second step (lactone to diol) uses different T2/P2 conditions. This dynamic optimization maintains high reaction rates while preserving selectivity for the desired diol products.
Solution Approach 2:
The patent systematically changes physical parameters (temperature and pressure) between reaction steps and within each step to optimize both rate and selectivity. By adjusting T1, P1 for the first hydrogenation and T2, P2 for the second hydrogenation, the process achieves high reaction rates while maintaining manufacturing precision for diol production.
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 method efficiently produces diols and lactones from biomass-derived carboxylic acids, enabling the synthesis of bio-derived branched polymers with improved properties and reduced environmental impact.
Implementation Method 1
reacting a C4 to C7 dicarboxylic acid with hydrogen (H2) gas on a first heterogeneous catalyst at a first temperature and a first pressure to form a C4 to C7 lactone
Implementation Method 2
reacting the C4 to C7 dicarboxylic acid with hydrogen (H2) gas on a first heterogeneous catalyst at a first temperature and a first pressure to form a C4 to C7 lactone
Implementation Method 3
reacting the lactone with hydrogen (H2) gas on a second heterogeneous catalyst at a second temperature and a second pressure
Implementation Method 4
reacting the lactone with hydrogen (H2) gas on a second heterogeneous catalyst at a second temperature and a second pressure to form a diol
Data Source
AI summary
Methods of forming a C4 to C7 diol compound, the methods including a first step of reacting a C4 to C7 dicarboxylic acid with hydrogen (H2) gas on a first heterogeneous catalyst at a first temperature and a first pressure to form a C4 to C7 lactone; and a subsequent step of reacting the lactone with hydrogen (H2) gas on a second heterogeneous catalyst at a second temperature and a second pressure, wherein the second temperature is lower than the first temperature. Also disclosed are methods of forming a solvent, the methods including reacting a C4 to C7 dicarboxylic acid with hydrogen (H2) gas on a first heterogeneous catalyst at a first temperature and a first pressure to form a solvent. Further disclosed herein are methods that include reacting mevalonolactone with hydrogen (H2) gas on a second heterogeneous catalyst at a second temperature and a second pressure to form a diol compound.