Alcohol Hydroxyl Conversion Using Metal Complex and Solid Base Catalysts
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Solution Overview
Problem
Conventional methods for converting a hydroxyl group of an alcohol suffer from substrate-specificity and inadequate catalytic activity, necessitating the development of a more efficient method and catalyst for this conversion.
Innovation Solution
A combination of a metal complex of Groups 7 to 11 in the periodic table, such as manganese, technetium, rhenium, iron, ruthenium, osmium, cobalt, rhodium, iridium, nickel, palladium, platinum, copper, silver, or gold, with a layered double hydroxide or composite oxide, particularly aluminum, magnesium, or calcium-based solid bases, is used to catalyze the conversion of hydroxyl groups in alcohols.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If conventional catalysts are used for hydroxyl group conversion, then the reaction can proceed, but the catalytic activity is inadequate for practical use
Solution Approach 1:
The patent employs a composite catalyst system combining a metal complex (containing Groups 7-11 metals such as Ru, Rh, Ir, Pd, Pt) with a solid base (such as magnesium oxide, calcium oxide, or hydrotalcite). This composite approach synergistically enhances catalytic activity by combining the metal complex's ability to activate the hydroxyl group with the solid base's ability to facilitate the alkylation reaction, thereby achieving high productivity and practical usability simultaneously.
2Adaptability or versatility
If conventional techniques are used, then substrate-specific reactions occur, but the method lacks versatility for different substrates
Solution Approach 1:
The patent develops a universal catalyst system comprising a metal complex and solid base that can effectively catalyze hydroxyl group conversion across diverse substrate types including primary alcohols, secondary alcohols, phenols, and carboxylic acids. The metal complex component provides broad substrate compatibility while the solid base enables versatile reaction conditions, allowing a single catalytic system to handle multiple substrate classes without requiring method redesign.
3Productivity
If alkyl halides are used as alkylating agents, then alkylation can occur, but excessive reaction and salt by-products are produced
Solution Approach 1:
The patent replaces traditional alkyl halide alkylating agents with alcohol molecules that undergo in-situ activation and conversion. The alcohol serves as both the substrate and the alkylating agent source, undergoing transformation to deliver the alkyl group while avoiding the formation of stoichiometric salt by-products. This approach uses a renewable, inexpensive alcohol feedstock instead of persistent halide 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
This approach achieves high catalytic activity, enabling effective conversion of hydroxyl groups in alcohols to produce valuable compounds like ketones and amines, overcoming the limitations of previous techniques.
Implementation Method 1
reacting: a compound having an active proton with a formula (2), and an alcohol with a formula (1) in the presence of a metal complex of Groups 7 to 11 in the periodic table and at least one solid base
Data Source
AI summary
The present invention relates to: a method for converting a hydroxyl group of an alcohol; and a catalyst which makes the method possible. A method for converting a hydroxyl group of an alcohol according to the present invention is characterized by producing a compound represented by CH(R1)(R2)Nu (wherein R1, R2 and Nu are as defined below) by reacting an alcohol represented by CH(R1)(R2)OH (wherein each of R1 and R2 represents a hydrogen atom, an optionally substituted alkyl group, or the like) and a compound having an active proton, which is represented by H-Nu (wherein Nu represents a group represented by -CHX1-EWG1 or -NR3R4; X1 represents a hydrogen atom or the like; EWG1 represents an electron-withdrawing group; and each of R3 and R4 represents a hydrogen atom, an optionally substituted alkyl group, or the like), with each other in the presence of a complex of a group 7-11 metal of the periodic table and at least one solid base that is selected from the group consisting of layered double hydroxides, composite oxides and calcium hydroxide.