Nitrile Conversion to Carboxylic Acids via Acid Hydrolysis
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Solution Overview
Problem
Current methods for transforming nitrile compounds, such as those produced in the hydrocyanation of butadiene, into valuable chemical intermediates or solvents are inefficient and often result in environmental issues like CO2 and nitrogen oxides emissions during combustion of by-products.
Innovation Solution
A process involving hydration of nitrile functions to amide functions followed by hydrolysis to carboxylic functions using strong mineral acids, with controlled water and acid ratios, and subsequent esterification to produce diesters, allowing for efficient recovery and separation of carboxylic compounds and diesters.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Use of energy by moving object
If nitrile compounds are combusted to recover energy, then energy recovery is achieved, but gaseous effluents containing CO2 and nitrogen oxides are produced
Solution Approach 1:
The patent converts the harmful nitrile by-products (which would otherwise be combusted and produce NOx emissions) into valuable chemical intermediates through hydrolysis. The harmful substance (nitrile compounds) is transformed into a beneficial product (carboxylic acids and esters), eliminating the need for combustion and the associated harmful emissions while still recovering energy value through chemical transformation.
Solution Approach 2:
The patent changes the chemical parameters of the nitrile compounds by controlling the hydrolysis reaction conditions (temperature, acid concentration, water-to-nitrile ratio) to selectively transform the nitrile functional group into carboxylic acid and ester groups, thereby changing the chemical composition from harmful to useful without combustion.
2Productivity
If nitrile compounds are hydrogenated into primary amines, then valuable monomers are produced, but purification steps are required
Solution Approach 1:
The patent extracts the nitrile by-products from the hydrocyanation process stream and subjects them to hydrolysis reaction, separating the transformation step from the main production process. This allows the nitrile compounds to be converted into carboxylic acids and esters through a controlled chemical reaction rather than requiring complex purification of hydrogenation products.
3Productivity
If distillation is used to separate and recover branched dinitrile compounds, then recovery is achieved, but the process is energy-intensive
Solution Approach 1:
The patent changes the approach from physical separation (distillation) to chemical transformation (hydrolysis). By changing the chemical parameters of the nitrile compounds through controlled hydrolysis reaction, the process avoids the high energy consumption of distillation while still achieving recovery and valorization of the branched dinitrile compounds as valuable chemical intermediates.
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 process enables the conversion of nitrile compounds into recoverable carboxylic acids and diesters, which can be used as chemical intermediates or solvents, reducing environmental impact and improving economic viability by utilizing a simple decantation and phase separation method.
Implementation Method 1
hydrating the nitrile functions into amide function by reaction with the water in the presence of a strong mineral acid
Implementation Method 2
hydrolysing the amide functions into carboxylic functions by reaction with water and a strong mineral acid
Data Source
AI summary
The present invention relates to a method for converting hydrocarbon compounds having at least one nitrile function into compounds having at least one carboxylic function, and to a method for obtaining ester compounds from the carboxylic compounds thus obtained. The invention provides a method for converting compounds having at least one nitrile function into compounds having at least one carboxylic function, which comprises hydrating the nitrile functions with amide function by reaction with water in the presence of a strong inorganic acid, and hydrolysing the amide functions into carboxylic functions y reaction with water and a strong inorganic acid. The carboxylic compounds thus obtained can then be esterified into diesters. The latter can advantageously be used as a solvent.