Solid-Phase Hydrogenation for High Cis-Trans Cyclobutanediol
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Solution Overview
Problem
Current methods for producing cyclobutanediol compounds, such as TMCBD, face challenges in achieving a high cis:trans ratio while being environmentally friendly, as they often require solvents and have low efficiency, which is not harmonious with green chemistry principles.
Innovation Solution
A catalytic hydrogenation reaction and isomerization process in a solid phase state using a metal catalyst without a solvent, specifically employing a cyclobutanedione compound and a metal catalyst like Ru, Pt, Pd, Rh, Ni, or Cu, to achieve a high cis:trans ratio of 1.5:1 to 5000:1 in cyclobutanediol compounds.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If catalytic hydrogenation is performed in a liquid phase with solvent, then the reaction proceeds smoothly, but the cis:trans ratio can be increased only to about 1.5:1 at the most
Solution Approach 1:
The patent applies phase transition by changing the reaction phase from liquid to solid state. The cyclobutanedione compound and catalyst are maintained in a solid phase during hydrogenation, which fundamentally alters the reaction mechanism and enables high cis:trans ratio control while maintaining efficiency.
Solution Approach 2:
The patent changes critical reaction parameters including temperature (maintaining below the melting point of the cyclobutanedione compound), pressure (0.1-10 MPa hydrogen pressure), and phase state (solid phase) to achieve both high cis:trans ratio and reaction efficiency simultaneously.
2Speed
If hydrogenation is performed at high temperature in gas phase, then reaction speed increases, but the cis:trans ratio remains about 1:1 to 1.6:1 and hydrogen consumption increases to 100-500 mol
Solution Approach 1:
The patent transitions from gas-phase to solid-phase hydrogenation, maintaining the reactants in solid state while introducing hydrogen gas. This phase transition enables controlled reaction kinetics that achieve both high reaction speed and high cis:trans ratio without excessive hydrogen consumption.
Solution Approach 2:
The patent optimizes temperature to be above 0°C but below the melting point of the cyclobutanedione compound, maintains hydrogen pressure at 0.1-10 MPa, and controls the solid-phase reaction conditions to achieve rapid reaction with high selectivity and low hydrogen consumption.
3Manufacturing precision
If reaction crystallization is used to precipitate cis isomer, then high cis:trans ratio is achieved, but large amount of solvent is required for filtration and washing
Solution Approach 1:
The patent extracts the need for large amounts of washing solvent by performing hydrogenation directly in solid phase. The product is obtained as solid crystals that can be filtered and dried without requiring extensive washing steps, thereby eliminating solvent consumption associated with washing.
Solution Approach 2:
The patent utilizes solid-phase reaction and solid crystalline product formation to eliminate the need for solvent-intensive filtration and washing operations. The solid-state reaction produces crystalline product that can be directly separated by simple filtration and drying.
4Productivity
If conventional hydrogenation methods are used, then TMCBD is produced, but the process is not environmentally friendly due to solvent usage
Solution Approach 1:
The patent extracts and eliminates the solvent component from the reaction system by performing hydrogenation in solid phase. This removes the source of environmental pollution associated with solvent disposal while maintaining high production efficiency.
Solution Approach 2:
The patent transitions from liquid-phase to solid-phase hydrogenation, eliminating the need for organic solvents that create environmental pollution. The solid-state reaction is inherently greener as it avoids solvent usage entirely.
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 stably produces cyclobutanediol compounds with a high cis:trans ratio under mild conditions, reducing environmental impact by eliminating the need for solvents and enhancing the quality and stability of resulting polyester materials.
Implementation Method 1
performing a catalytic hydrogenation reaction and an isomerization reaction in the cyclobutanediol compound in a solid phase state in the presence of a metal catalyst
Implementation Method 2
catalytic hydrogenation reaction from TMCBK to TMCBD
Implementation Method 3
isomerization reaction in the cyclobutanediol compound
Data Source
AI summary
Provided is a process in which a cyclobutanediol compound having a high cis:trans ratio can be stably obtained. The cyclobutanediol compound having a cis:trans ratio of 1.5:1 to 5000:1 is produced by using at least one compound selected from a group consisting of a cyclobutanedione compound, a cyclobutane ketol compound, and a cyclobutanediol compound as a raw material, and performing a catalytic hydrogenation reaction and an isomerization reaction in the cyclobutanediol compound in a solid phase state in the presence of a metal catalyst without adding a solvent.