Resin-Supported Transition Metal Complex for Hydrophosphorylation

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Solution Overview

Problem

The existing catalysts for hydrophosphorylation reactions, such as those with transition metals immobilized on polystyrene resins with triphenylphosphine, suffer from low phosphorus content, requiring large resin amounts, low reaction efficiency, and frequent metal leaching, leading to side reactions.

Innovation Solution

A complex compound is formed by reacting a resin with a phosphine substituent on its surface with a transition metal, creating a resin-supported transition metal complex that acts as an efficient catalyst for hydrophosphorylation reactions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If a transition metal is immobilized on a polystyrene resin with triphenylphosphine, then the catalyst can be used for hydrophosphorylation reaction, but the phosphorus content on the resin surface is insufficient, requiring a very large amount of resin

Engineering Contradiction:
Improvephosphorus contentVSAvoidreaction efficiency
Core Design Contradiction:
Quantity of substanceVSProductivity

Solution Approach 1:

The patent applies local quality by concentrating phosphorus-containing groups specifically on the surface of the resin fine particles rather than distributing them throughout the bulk resin. This surface-localized phosphorus configuration ensures sufficient phosphorus content at the reaction interface while minimizing the total resin quantity needed, directly resolving the contradiction between phosphorus content and resin amount.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent creates a composite material structure combining resin fine particles with surface-grafted phosphorus-containing groups and immobilized transition metals. This composite approach integrates multiple functional components (resin support, phosphorus ligands, metal catalyst) into a single heterogeneous catalyst system that achieves high phosphorus content and catalytic efficiency simultaneously.

Inventive Principle:
Principle #40Composite materials

2Quantity of substance

If a large amount of resin is used to compensate for low phosphorus content, then sufficient phosphorus can be added, but the reaction efficiency remains low

Engineering Contradiction:
Improvephosphorus amountVSAvoidreaction efficiency
Core Design Contradiction:
Quantity of substanceVSProductivity

Solution Approach 1:

By localizing phosphorus-containing groups on the resin surface where catalysis occurs, the patent ensures that the phosphorus is positioned exactly where it is needed for maximum effectiveness. This eliminates the waste of using large amounts of bulk resin that does not contribute to the reaction, thereby achieving both sufficient phosphorus amount and high reaction efficiency.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent changes the structural parameters of the resin from conventional bulk resin to fine particles with controlled surface properties. This parameter change increases the surface area to volume ratio, allowing sufficient phosphorus content to be achieved with smaller total resin amounts and improving mass transfer, which enhances reaction efficiency.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If transition metal is immobilized on the resin surface, then it can catalyze the reaction, but leaching of metal components occurs frequently, leading to side reactions

Engineering Contradiction:
Improvecatalytic activityVSAvoidmetal stability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent creates a stable composite structure where the transition metal is firmly immobilized on the resin surface through coordination with phosphorus-containing groups. The resin matrix provides structural support while the surface-bound phosphorus ligands provide stable coordination sites for the metal, preventing leaching while maintaining catalytic activity. This composite design ensures both productivity and reliability.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent uses resin fine particles as a disposable support matrix that can be easily separated from the reaction mixture and discarded after use. The immobilized metal catalyst on this disposable support prevents metal leaching into the product, as the entire catalyst system can be removed as a single unit, ensuring product purity and eliminating the need for complex metal recovery processes.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

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 complex compound effectively promotes hydrophosphorylation reactions at temperatures equal to or higher than room temperature, using inexpensive and commercially available raw materials, thereby reducing manufacturing costs and improving reaction efficiency.

Implementation Method 1

a complex compound of a resin fine particle represented by general formula (1) and a transition metal

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Implementation Method 2

useful as a catalyst for a hydrophosphorylation reaction

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS12280364B2Complex compound and method for manufacturing the same
Publication Date: 2025.04.22 MARUZEN PETROCHEMICAL CO LTD
  • US12280364B2 patent drawing
  • US12280364B2 patent drawing
  • US12280364B2 patent drawing

AI summary

[Problem] To provide a complex compound useful as a catalyst for a hydrophosphorylation reaction and a process for producing the same.[Means to Solve the Problem] A complex compound of the present invention is a complex compound of a resin fine particle represented by the following general formula (1):wherein, R1 represents a substituted or unsubstituted hydrocarbon group, R2 represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, R3 and R4 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and based on the total of 100% of the values of n and m, the value of n is within the range of 20 to 100%, the value of m is within the range of 0 to 80%, and * represents bonding with the surface of the resin fine particle and a transition metal.