Ruthenium Complex with NHC Ligand for Mild Hydrogenation
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
Current ruthenium catalysts for hydrogenation and dehydrogenation reactions require harsh conditions and are costly, with residual metal issues and safety concerns, and existing catalysts for N-alkylation reactions use hazardous reagents.
Innovation Solution
A ruthenium complex with a bis(phosphinoalkyl)amine tridentate ligand and a N-heterocyclic carbene monodentate ligand that can be easily produced and handles gentle reaction conditions, catalyzing hydrogenation, dehydrogenation, and N-alkylation reactions with high activity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If conventional ruthenium catalysts are used for hydrogenation and dehydrogenation reactions, then catalytic activity is achieved, but harsh reaction conditions and high costs are required
Solution Approach 1:
The patent changes the chemical parameters of the catalyst by introducing a specific ligand system (N-heterocyclic carbene and phosphine combination) to the ruthenium center. This modifies the electronic and steric properties of the catalyst, enabling it to function effectively under milder temperature and pressure conditions while maintaining high catalytic activity for hydrogenation and dehydrogenation reactions
2Productivity
If conventional ruthenium catalysts are used, then hydrogenation reactions can be performed, but residual metal issues and safety concerns arise
Solution Approach 1:
The patent employs a carefully designed organometallic catalyst system that operates efficiently at low loadings and under mild conditions, reducing the overall metal residue in products. The catalyst's high activity allows for shorter reaction times and lower temperatures, thereby minimizing safety hazards associated with harsh conditions while still achieving complete hydrogenation or dehydrogenation
3Productivity
If existing catalysts are used for N-alkylation reactions, then N-alkylamine compounds can be synthesized, but hazardous alkylating agents are required
Solution Approach 1:
The patent uses the ruthenium catalyst as an intermediary to facilitate N-alkylation reactions through a different mechanism than conventional methods. Instead of using hazardous alkylating agents, the catalyst enables alcohol-amine condensation reactions to proceed efficiently, with the ruthenium complex mediating the formation of the C-N bond under mild conditions, thereby eliminating the need for mutagenic reagents
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 ruthenium complex enables efficient production of alcohols, aldehydes, and amines under mild conditions, reducing residual metal issues and safety hazards, and facilitates N-alkylation without using hazardous alkylating agents.
Implementation Method 1
hydrogenation using a transition metal catalyst is useful from the view point of reducing by-products, excellent operability, and safety of work
Implementation Method 2
hydrogenation of ketones, and hydrogenation of optically active aldehydes, optically active esters and optically active amides
Implementation Method 3
dehydrogenation using a transition metal catalyst is useful in terms of safety because it does not require an explosive substance such as a peroxide generally used as an oxidant
Implementation Method 4
condensation between alcohols and amines using the complex as a catalyst
Data Source
Figure 1
AI summary
The present invention provides a novel ruthenium complex that is easy to produce and handle and that can be supplied relatively inexpensively, a method for producing this ruthenium complex, a method for producing alcohols and the like using this ruthenium complex as a catalyst, a method for producing carbonyl compounds using this ruthenium complex as a catalyst, and a method for producing N-alkylamine compounds using this ruthenium complex as a catalyst. The present invention pertains to a ruthenium complex represented by general formula (1) RuX1X2(PNP)(NHC)m(Solv)n(1) (in general formula (1), X1 and X2 each independently represent a monovalent anionic monodentate ligand; PNP represents a tridentate aminodiphosphine ligand, NHC represents an N-heterocyclic carbene derived from a nitrogen-containing heterocyclic ring, and Solv represents a coordinating solvent; and m represents an integer from 1 to 3, n represents an integer from 0 to 2, and 1 ≤ m + n ≤ 3.), a method for producing the same, a catalyst including the same, and methods for producing various organic compounds using this catalyst.