Ferric Carboxylate Catalyst Isomerization 1,4-Dichlorobutene-2
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Solution Overview
Problem
Existing isomerization processes for producing 3,4-dichlorobutene-1 using copper and iron catalysts face inefficiencies, such as low conversions at low temperatures and excessive by-product formation at high temperatures, along with catalyst deactivation and high costs due to basic ligands.
Innovation Solution
A process utilizing a ferric carboxylate catalyst, specifically iron (III) carboxylate salts like iron (III) 2-ethylhexanoate and iron (III) naphthenate, for isomerizing 1,4-dichlorobutene-2 to 3,4-dichlorobutene-1, which operates at controlled temperatures and pressures to minimize by-product formation and maintain catalyst stability.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If copper complex catalysts are used for isomerization at low temperatures, then conversion is improved, but by-product formation increases
Solution Approach 1:
The patent changes the catalyst parameter from copper complexes to ferric carboxylates, which fundamentally alters the reaction behavior. This new catalyst type enables effective operation at lower temperatures without the by-product formation issues associated with copper complexes, resolving the contradiction between conversion and by-product formation.
Solution Approach 2:
The patent employs ferric carboxylate catalysts that can be easily removed from the reaction mixture through simple filtration or extraction, eliminating the need for complex catalyst recovery systems. This approach prioritizes ease of process termination and product purification over catalyst longevity, effectively managing the trade-off between catalytic activity and by-product formation.
2Productivity
If iron compounds with basic ligands are used as catalysts, then catalytic activity is improved, but catalyst stability deteriorates due to protonation and deactivation
Solution Approach 1:
The patent changes the ligand parameter of the iron catalyst from basic ligands (which cause protonation and deactivation) to non-basic carboxylate ligands. This chemical parameter change maintains the catalytic activity of iron compounds while eliminating the instability caused by protonation, thereby resolving the contradiction between activity and stability.
Solution Approach 2:
The carboxylate ligand acts as an intermediary that bridges the iron metal center and the substrate without requiring strong basicity. This intermediary ligand maintains the necessary electronic properties for catalysis while being resistant to protonation, thus protecting the catalyst from deactivation and improving overall stability.
3Productivity
If high temperatures are used for isomerization, then conversion rate is improved, but by-product formation increases
Solution Approach 1:
The patent changes the catalyst parameter to ferric carboxylate, which fundamentally alters the temperature-dependence relationship. This new catalyst enables high conversion rates to be achieved at lower temperatures, thereby resolving the contradiction between conversion rate and by-product formation that typically worsens with temperature increase.
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 yield and low by-product formation, maintaining catalyst longevity and reducing operational costs, with efficient conversion of 1,4-dichlorobutene-2 to 3,4-dichlorobutene-1, suitable for producing chloroprene monomer.
Implementation Method 1
contacting 1,4-dichlorobutene-2 with a ferric carboxylate catalyst of the formula... whereby a portion of the 1,4-dichlorobutene-2 is isomerized to form 3,4-dichlorobutene-1
Data Source
AI summary
3,4-Dichlorobutene-1 is produced by a process comprising the step of contacting 1,4-dichlorobutene-2 with either 1) a ferric carboxylate catalyst of the formulawhere R is an alkyl or alkenyl group of 4-18 carbon atoms, a cycloalkyl or cycloalkenyl group of 6-18 carbon atoms or an aryl group selected from phenyl, benzyl, xylyl, tolyl, and naphthyl groups, whereby a portion of the 1,4-dichlorobutene-2 is isomerized to form 3,4-dichlorobutene-1, or 2) a ferric carboxylate catalyst of the formulawhere R, R′ and R″ are independently alkyl or alkenyl groups of 4-18 carbon atoms, cycloalkyl or cycloalkenyl groups of 6-18 carbon atoms or aryl groups selected from phenyl, benzyl, xylyl, tolyl, and naphthyl groups, the sum of m, n and o is 3 and m, n and o are independently 0, 1 or 2, whereby a portion of the 1,4-dichlorobutene-2 is isomerized to form 3,4-dichlorobutene-1.