Gas-Phase Nitrilation Catalyst for Fatty Acid Conversion

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Solution Overview

Problem

Current processes for nitrilation of fatty acids or esters suffer from long reaction times, isomerization of double bonds, and high energy costs, leading to reduced conversion and yield, especially when using unsaturated reactants or methyl esters, which results in unwanted by-products and limited application potential.

Innovation Solution

A gas-phase or mixed liquid-gas phase nitrilation process using a solid catalyst comprising metal oxides from column 8 of the periodic table, such as iron oxide, in combination with aluminum, zirconium, niobium, or tantalum oxides, operating at 180-400°C with short contact times to minimize isomerization and energy consumption.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If liquid-phase batch process is used for nitrilation of fatty acids, then conversion can be achieved, but reaction time becomes very long (several hours)

Engineering Contradiction:
Improvereaction timeVSAvoidreaction time
Core Design Contradiction:
ProductivityVSLoss of time

Solution Approach 1:

The patent transitions from liquid-phase batch process to gas-phase continuous process. The fatty acid is vaporized and reacted with ammonia in the gas phase, enabling continuous operation and dramatically reducing reaction time from several hours to much shorter contact times while maintaining conversion efficiency.

Inventive Principle:
Principle #36Phase transitions

Solution Approach 2:

The patent implements continuous operation in the gas-phase process where fatty acid vapor and ammonia continuously flow through the catalyst bed. This continuous useful action eliminates the batch processing steps and significantly reduces total reaction time while maintaining high conversion rates.

Inventive Principle:
Principle #20Continuity of useful action

2Productivity

If gas-phase process is used for nitrilation, then reaction time is reduced, but temperature must be increased (250-600°C) which increases energy consumption

Engineering Contradiction:
Improvereaction speedVSAvoidenergy consumption
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

The patent optimizes the temperature parameter to a specific range (250-600°C) and introduces a catalyst to lower the effective activation energy. This allows the reaction to proceed at moderate temperatures with high speed, avoiding excessive energy consumption while maintaining fast reaction rates.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces a catalyst as an intermediary substance that facilitates the nitrilation reaction. The catalyst provides an alternative reaction pathway with lower activation energy, enabling the reaction to proceed at lower temperatures with higher speed, thus reducing energy consumption while maintaining productivity.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Productivity

If conventional catalysts are used in gas-phase process, then conversion can be achieved, but double bond isomerization occurs leading to unwanted by-products

Engineering Contradiction:
Improveconversion rateVSAvoidisomerization by-products
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent uses a specific catalyst composition (metal oxides from column 8 of periodic table combined with aluminum, zirconium, niobium, or tantalum oxides) that has localized catalytic properties suitable for nitrilation without promoting isomerization. The catalyst is designed to be selective for the desired reaction while minimizing harmful side reactions.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent employs a composite catalyst system combining metal oxides from column 8 with other metal oxides (aluminum, zirconium, niobium, or tantalum oxides). This composite material leverages the complementary properties of different oxides to achieve high conversion while suppressing double bond isomerization, reducing unwanted by-products.

Inventive Principle:
Principle #40Composite materials

4Temperature

If methyl ester is used as reactant, then reaction conditions are milder, but N-methylation by-product forms reducing yield

Engineering Contradiction:
Improvereaction conditionsVSAvoidN-methylation by-product
Core Design Contradiction:
TemperatureVSObject-generated harmful factors

Solution Approach 1:

The patent optimizes reaction parameters (temperature, pressure, catalyst composition) to suppress the N-methylation side reaction while maintaining mild reaction conditions. By carefully controlling these parameters, the process achieves high yield of desired nitrile product even when using methyl esters as reactants.

Inventive Principle:
Principle #35Parameter changes

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 achieves high conversion and yield with reduced by-products, specifically limiting double bond migration and N-methylation, while being economically advantageous and energy-efficient, as demonstrated by the Fe2O3/ZrO2 mixture.

Implementation Method 1

The invention relates to a process for the nitrilation of the acid function or else of the ester function... by reacting ammonia in a reactor operating continuously in the gas phase or in the mixed gas-liquid phase... in the presence of a solid catalyst comprising: at least one metal oxide, the metal of which belongs to column 8 of the periodic table, as a mixture with at least one metal oxide chosen from aluminum oxides, zirconium oxides, niobium oxides, tantalum oxides and tin oxides

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS10287238B2Gas-phase and liquid-gas-phase nitrilation process
Publication Date: 2019.05.14 ARKEMA FRANCE SA
  • US10287238B2 patent drawing
  • US10287238B2 patent drawing
  • US10287238B2 patent drawing

AI summary

A process for the nitrilation of a fatty acid or of a fatty acid ester, which is optionally unsaturated, by reacting the fatty acid or fatty acid ester with ammonia in a reactor operating continuously in the gas phase or in the mixed gas-liquid phase in a temperature range of from 180 to 400° C., in the presence of a solid catalyst comprising at least one metal oxide, the metal of which belongs to column 8 of the periodic table, as a mixture with at least one metal oxide chosen from aluminum oxides, zirconium oxides, niobium oxides, tantalum oxides and tin oxides, the metal oxide(s), the metal of which belongs to column 8, being present in a volume ratio of 0.1 to 0.6 relative to the volume of the mixture of all the oxides.