Butadiene Telomerization Catalyst Induction Period Reduction
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Solution Overview
Problem
Existing processes for producing 1-octene through butadiene telomerization often experience an induction period due to the slow reduction of Pd(II) species to an active Pd(0) complex, which delays the telomerization reaction from reaching its maximum rate.
Innovation Solution
A catalyst composition is prepared by combining a palladium source with 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane ligand and a methoxyoctadiene compound in a primary aliphatic alcohol, along with a promoter and carboxylic acid, to form a complex that reduces the induction period and enhances storage stability and solubility.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Stability of the object's composition
If Pd(II) species are used as catalyst precursor, then the catalyst is stable and soluble, but the reduction to active Pd(0) complex is slow causing induction period
Solution Approach 1:
The patent applies preliminary action by pre-forming the active Pd(0) complex through reduction before the telomerization reaction begins. Sodium methoxide is added to the catalyst precursor solution to reduce Pd(II) to Pd(0) in advance, creating an actively reduced catalyst that eliminates the induction period while maintaining catalyst stability and solubility.
2Duration of action of stationary object
If Pd(II) species are used as catalyst precursor, then the catalyst can be stored, but the reaction rate is delayed due to slow reduction
Solution Approach 1:
The patent resolves this contradiction by performing the reduction action in advance before storage. The catalyst is prepared with sodium methoxide to reduce Pd(II) to Pd(0) beforehand, allowing the pre-reduced catalyst to be stored with maintained activity and then used immediately for high-rate telomerization without induction delay.
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 catalyst composition significantly reduces or eliminates the induction period, leading to improved reaction rates and storage stability, ensuring efficient telomerization of butadiene to produce 1-octene with enhanced solubility and operational reliability.
Implementation Method 1
contacting butadiene and an organic hydroxyl compound represented by the formula ROH, where R is a substituted or unsubstituted C1-C20 hydrocarbyl and the organic hydroxyl compound is not glycerol, in a reaction fluid in the presence of a palladium catalyst and a phosphine ligand
Implementation Method 2
the palladium (Pd)(II)-containing catalyst precursor appears to be reduced by a sodium methoxide promoter in methanol in the presence of 1,3-butadiene to a palladium(Pd(0)) bis-phosphine complex
Data Source
AI summary
Catalyst compositions are prepared by contacting a palladium source and 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane and a methoxyocta-diene compound, in a primary aliphatic alcohol, under suitable conditions including a ratio of equivalents of palladium to equivalents of 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane ranging from greater than 1:1 to 1:1.3. The result is a complex of palladium, a 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaada-mantane ligand, and a ligand selected from a methoxyoctadiene ligand, an octadienyl ligand, or a protonated octadienyl. Such complexes may, in solution, exhibit surprising solubility and storage stability and are useful in the telomerization of butadiene, which is a step in the production of 1-octene.