Water-Soluble Phosphine Catalyst for Telomerization Recovery
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Solution Overview
Problem
Current methods for producing 2,7-octadien-1-ol in telomerization reactions face challenges such as high costs due to equipment requirements, low selectivity, and inefficient recovery of palladium catalysts and tertiary amines, as well as issues with the use of sulfolane and inorganic salts accumulating in the reaction system.
Innovation Solution
The use of a palladium catalyst comprising a specific ammonium salt of bis(6-methyl-3-sulphophenyl)phenylphosphine, which allows for high selectivity and efficient recovery of the catalyst by extracting products with an organic solvent and recovering palladium from the aqueous phase, thereby reducing costs and improving process efficiency.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If a palladium catalyst comprised of a phosphorous compound and a palladium compound is used for telomerization reaction, then the production of 2,7-octadien-1-ol is achieved, but the recovery of palladium catalyst becomes difficult and costly
Solution Approach 1:
The patent introduces a water-soluble phosphine compound as an intermediary that forms a water-soluble palladium catalyst complex. This intermediary enables the palladium catalyst to be recovered through simple water extraction, eliminating the need for complex recovery processes. The water-soluble phosphine acts as a mediator between the palladium compound and the reaction system, facilitating easy separation and recovery.
Solution Approach 2:
The patent changes the solubility parameter of the phosphine compound from organic-soluble to water-soluble. This parameter change transforms the catalyst system from one requiring complex recovery methods to one that can be easily recovered through water extraction. The water-soluble phosphine compound modifies the catalyst's interaction with the reaction medium, enabling simple separation.
2Productivity
If sulfolane is used as a solvent in telomerization reaction, then the reaction efficiency is improved, but the cost increases and disposal becomes complex
Solution Approach 1:
The patent replaces expensive sulfolane with water, which is inexpensive and easily disposable. The water-soluble phosphine catalyst system allows the reaction to proceed efficiently in water, eliminating the need for costly sulfolane solvent. Water can be simply evaporated or disposed of after the reaction, avoiding the complex disposal requirements of sulfolane.
Solution Approach 2:
The patent changes the solvent parameter from organic solvent (sulfolane) to water. This parameter change reduces cost and simplifies disposal while maintaining reaction efficiency through the water-soluble phosphine catalyst system. The solvent parameter is fundamentally changed to something more economical and environmentally friendly.
3Productivity
If inorganic salts are accumulated in the reaction system, then the telomerization reaction proceeds, but the recovery of palladium catalyst is hindered
Solution Approach 1:
The water-soluble phosphine compound acts as an intermediary that prevents inorganic salt accumulation from interfering with catalyst recovery. By forming a water-soluble complex, the phosphine ensures that the palladium catalyst remains in the aqueous phase even when inorganic salts are present, facilitating clean separation through water extraction without hindrance from salt accumulation.
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 approach enhances the selectivity and recovery of 2,7-octadien-1-ol in telomerization reactions, simplifies the recovery process, and minimizes the use of costly solvents like sulfolane, while maintaining high palladium catalyst efficiency.
Implementation Method 1
a palladium catalyst comprised of a phosphorous compound and a palladium compound
Implementation Method 2
it is useful as a catalyst for production of 2,7-octadien-1-ol by reacting two butadiene molecules with one water molecule
Implementation Method 3
at least part of the reaction mixed liquid is extracted with a saturated aliphatic hydrocarbon or the like to separate out the 2,7-octadien-1-ol
Data Source
AI summary
Provided are a water-soluble triarylphosphine for a palladium catalyst, which has high selectivity in a telomerization reaction and can be recovered with efficiency, an ammonium salt thereof, and a method for efficiently producing the same. Specifically, provided are bis(6-methyl-3-sulphophenyl)phenylphosphine; a bis(6-methyl-3-sulphonatopheyl)phenylphosphine diammonium salt obtained by reacting the phosphine with a tertiary amine having a total of 3 to 27 carbon atoms in groups bonded to one nitrogen atom; and a method for producing the same.