Hydrolyzed Acyl Halide Solubility in Hydrocarbon Solvents
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Solution Overview
Problem
Hydrolyzed and partially hydrolyzed acyl halide compounds have low solubility in hydrocarbon or halogenated hydrocarbon solvents, making it difficult to prepare in-situ solutions for applications such as polyamide preparation.
Innovation Solution
A method involving a hydrocarbon or halogenated hydrocarbon solvent, water at a concentration above its solubility limit, and a tri-hydrocarbyl phosphate compound is used to produce a reaction product with a solubility limit of less than 1 weight percent, maintaining solubility by adjusting molar ratios and concentrations.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If hydrolyzed acyl halide compounds are prepared in hydrocarbon or halogenated hydrocarbon solvents, then the reaction can proceed in a non-aqueous environment suitable for polyamide preparation, but the solubility of hydrolyzed products is limited to less than 0.02 wt. %
Solution Approach 1:
The patent introduces a carboxylic acid byproduct as an intermediary substance that forms a soluble complex with hydrolyzed acyl halide compounds in hydrocarbon solvents. This intermediary complex allows the hydrolyzed products to remain in solution at concentrations far exceeding their normal solubility limits, enabling the reaction to proceed effectively in non-aqueous environments suitable for polyamide preparation.
2Productivity
If the concentration of hydrolyzed acyl halide compounds is increased above their solubility limit, then the reaction productivity improves, but the compounds precipitate out of solution
Solution Approach 1:
The patent creates a composite solution system consisting of hydrocarbon solvent, carboxylic acid byproduct, and hydrolyzed acyl halide compounds. The carboxylic acid component acts as a solubilizing agent that forms a composite molecular structure with the hydrolyzed products, maintaining solution homogeneity at concentrations well above the normal solubility limit of less than 0.02 wt. %.
3Speed
If water is added to promote hydrolysis of acyl halide compounds, then the reaction rate increases, but water solubility in hydrocarbon solvents is exceeded
Solution Approach 1:
The carboxylic acid byproduct serves as an intermediary that enables the system to tolerate water concentrations above the normal solubility limit in hydrocarbon solvents. By forming soluble complexes with hydrolyzed products, the carboxylic acid prevents phase separation and emulsion formation, allowing water to remain in the system at higher concentrations to promote hydrolysis reaction rates.
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 method allows for the production of hydrolyzed acyl halide compounds at concentrations above their solubility limits, enhancing their solubility and selectivity towards the mono-hydrolyzed form, facilitating their use in applications like polyamide preparation.
Implementation Method 1
a tri-hydrocarbyl phosphate compound... enhancing their solubility
Implementation Method 2
hydrolyzed and partially hydrolyzed analogs... prepared a reaction product comprising at least one acyl halide functional group and a carboxylic acid functional group
Data Source
AI summary
An in-situ method for preparing a hydrolyzed, acyl halide-containing compound by combining a reactant including a plurality of acyl halide functional groups containing reactant, a tri-hydrocarbyl phosphate compound and water within a hydrocarbon or halogenated hydrocarbon solvent.