Tri-hydrocarbyl Phosphate Solubilizing Carboxylic Acids in Hydrocarbon Solvents
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Solution Overview
Problem
Compounds with carboxylic acid functional groups have poor solubility in hydrocarbon solvents, limiting their application in processes such as polyamide preparation.
Innovation Solution
A solution comprising at least 80 v/v% hydrocarbon solvent, a hydrocarbon compound with an aliphatic or arene moiety substituted with an acyl halide and carboxylic acid, and 0.01 to 10 weight percent of a tri-hydrocarbyl phosphate compound, which increases the solubility of the hydrocarbon compound beyond its solubility limit.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Quantity of substance
If carboxylic acid-containing compounds are used in hydrocarbon solvents, then the solubility is improved, but the concentration remains limited below 0.02 weight percent
Solution Approach 1:
A tri-hydrocarbyl phosphate compound is introduced as an intermediary substance to facilitate the interaction between the carboxylic acid-containing compound and the hydrocarbon solvent. The phosphate compound acts as a solubility-enhancing mediator that allows higher concentrations of the carboxylic acid compound to dissolve in the hydrocarbon solvent, overcoming the natural solubility limitation.
Solution Approach 2:
The invention changes the chemical composition parameters of the solvent system by adding tri-hydrocarbyl phosphate compound at specific concentrations (0.01 to 10 weight percent). This parameter change transforms the solvent properties, enabling it to accommodate much higher concentrations of carboxylic acid-containing compounds (greater than 0.02 weight percent) while maintaining solution stability.
2Productivity
If the concentration of hydrocarbon compound is increased beyond its solubility limit, then the productivity is improved, but the solution becomes unstable or precipitates
Solution Approach 1:
The tri-hydrocarbyl phosphate compound serves as a stabilizing intermediary that prevents precipitation and maintains solution stability even at concentrations exceeding the natural solubility limit of the carboxylic acid-containing compound in the hydrocarbon solvent.
Solution Approach 2:
The invention creates a composite solvent system combining hydrocarbon solvent, tri-hydrocarbyl phosphate compound, and carboxylic acid-containing compound. This composite formulation achieves synergistic effects where the phosphate compound and carboxylic acid compound work together to enhance mutual solubility and maintain stability at higher concentrations.
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 tri-hydrocarbyl phosphate significantly enhances the solubility of the hydrocarbon compound, allowing for higher concentration solutions useful in applications like polyamide preparation, with solubility increases of at least 10%.
Implementation Method 1
a method for increasing the solubility of a hydrocarbon compound... within a hydrocarbon solvent... comprising the step of preparing a solution comprising... tri-hydrocarbyl phosphate compound
Data Source
AI summary
A method for increasing the solubility of a hydrocarbon compound comprising an aliphatic or arene moiety substituted with at least one acyl halide and at least one carboxylic acid functional group within a hydrocarbon solvent, wherein the method includes the step of preparing a solution comprising: at least 80 v/v% of the hydrocarbon solvent, the hydrocarbon compound, and a tri-hydrocarbyl phosphate compound, wherein the concentration of the hydrocarbon compound is greater than its solubility limit within the solvent but less than its solubility limit in the solution and the hydrocarbon.