Crystalline Ligand Forms for Homogeneous Catalysis Handling
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Solution Overview
Problem
Existing methods for producing 6,6′-[[3,3′,5,5′-tetrakis(1,1-dimethylethyl)-[1,1′-biphenyl]-2,2′-diyl]bis(oxy)]bis-dibenzo[d,f][1,3,2]-dioxaphosphepine result in sticky products that cake or form dust, making them unsuitable for industrial-scale use as ligands in homogeneous catalysis due to the presence of solvates like acetonitrile, which interfere with catalytic activity.
Innovation Solution
Development of crystalline non-solvated and solvated forms of the compound, specifically toluene-monosolvate, non-solvated, and acetone-solvates, which are characterized by specific X-ray powder diffraction patterns and prepared through controlled crystallization processes, eliminating tackiness and dust formation issues.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If conventional production methods are used to produce compound I, then the product can be obtained, but it exhibits sticky properties, caking, and dust formation due to solvate presence
Solution Approach 1:
The patent applies parameter changes by modifying the crystallization conditions (temperature, solvent selection, cooling rate) to obtain different crystalline forms of compound I. Specifically, crystallization from toluene at temperatures of 0-25°C yields the toluene-solvate form, while crystallization from non-coordinating solvents at higher temperatures yields the non-solvated form. This changes the physical state and handling properties of the product without altering its chemical composition.
Solution Approach 2:
The patent utilizes phase transitions by controlling the crystallization process to form specific solid-phase structures. The transition from amorphous or solvated sticky material to well-defined crystalline phases (toluene-solvate or non-solvated forms) eliminates tackiness and improves handling. The controlled crystallization from solution phase to solid crystal phase is the key phase transition applied.
2Ease of manufacture
If acetonitrile solvate is present in the product, then crystallization can occur, but catalytic activity is interfered with due to acetonitrile coordination
Solution Approach 1:
The patent applies the extraction principle by removing the harmful acetonitrile solvent from the crystal lattice through controlled crystallization from alternative solvents. By crystallizing from toluene or other non-coordinating solvents, the acetonitrile is excluded from the crystal structure, yielding a pure non-solvated form that maintains catalytic activity. This extracts the interfering solvent component from the final product.
Solution Approach 2:
The patent uses intermediary solvents (toluene, ethyl acetate, dichloromethane) as mediators in the crystallization process. These intermediary substances facilitate crystal formation without being incorporated into the final crystal structure, unlike acetonitrile which forms stable solvates. The intermediary solvent enables crystallization while allowing the removal of harmful coordinating solvents.
3Productivity
If product is obtained with sticky properties, then it can be produced, but it forms dust and cakes making it unsuitable for industrial use
Solution Approach 1:
The patent applies parameter changes by optimizing crystallization parameters (temperature range of 0-25°C, solvent-to-solute ratio, cooling rate) to produce well-defined crystals instead of sticky material. The specific parameter of crystallization temperature is critical: lower temperatures favor the toluene-solvate crystalline form, while higher temperatures favor the non-solvated form, both of which are free-flowing and non-sticky.
Solution Approach 2:
The patent utilizes phase transitions to convert the sticky amorphous or poorly-crystallized material into well-defined crystalline phases. The controlled transition from disordered solid or solvated material to ordered crystal structures eliminates the harmful sticky properties, dust formation, and caking tendencies, yielding an industrial-grade product with excellent handling characteristics.
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 new crystalline forms exhibit improved handling, high purity, and stability, allowing their use as effective ligands in transition metal catalysts for hydroformylation, hydrocyanation, or hydrogenation without interfering with catalytic activity.
Implementation Method 1
Development of crystalline non-solvated and solvated forms of the compound, specifically toluene-monosolvate, non-solvated, and acetone-solvates, which are characterized by specific X-ray powder diffraction patterns and prepared through controlled crystallization processes
Implementation Method 2
characterized by specific X-ray powder diffraction patterns
Data Source
AI summary
The present invention relates to a crystalline non-solvated form of 6,6′-[[3,3′,5,5′-tetrakis(1,1-dimethylethyl)-[1,1′-biphenyl]-2,2′-diyl]bis(oxy)]bis-dibenzo[d,f][1,3,2]-dioxaphosphepine (compound I) and toluene-solvates and acetone-solvates thereof.