Rhodium-Molybdenum Hydroxyapatite Catalyst for Amide Hydrogenation

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Solution Overview

Problem

Current methods for converting amide compounds to amines are inefficient, requiring high pressure and temperature, generating toxic waste, and involve costly, reusable catalysts with poor substrate compatibility and low durability.

Innovation Solution

A catalyst system comprising rhodium and molybdenum supported on hydroxyapatite, allowing for hydrogenation of amides under moderate conditions with high selectivity and durability, enabling safe and cost-effective industrial-scale production of amines.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If conventional catalysts (copper-chromium, rhenium, nickel) are used for amide hydrogenation, then the reaction can proceed, but high pressure (200 atm) and high temperature (200°C or higher) are required

Engineering Contradiction:
Improvereaction temperatureVSAvoidcatalyst activity
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The patent employs a composite catalyst system consisting of rhodium and molybdenum supported on hydroxyapatite. This composite structure combines the high catalytic activity of noble metals with the unique properties of the hydroxyapatite support, enabling the reaction to proceed at lower temperatures (50-150°C) and pressures (1-30 atm) while maintaining high conversion rates and selectivity.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

Hydroxyapatite serves as a porous support material with a specific surface area that provides numerous active sites for catalyst deposition. The porous structure increases the contact area between the catalyst and reactants, enhancing catalytic efficiency under milder reaction conditions compared to conventional non-porous catalyst supports.

Inventive Principle:
Principle #31Porous materials

2Productivity

If strong reductants (lithium aluminum hydride, sodium borohydride) are used for amide reduction, then the conversion to amine is achieved, but a large amount of metallic waste is generated

Engineering Contradiction:
Improveconversion efficiencyVSAvoidmetallic waste
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent replaces stoichiometric chemical reduction methods with catalytic hydrogenation. Instead of using large amounts of stoichiometric reductants that generate metallic waste, the invention uses a catalytic system with molecular hydrogen as the reductant, where the catalyst facilitates the reaction at low concentrations and can be reused multiple times, dramatically reducing metallic waste generation.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

Solution Approach 2:

The invention changes the reaction parameters from stoichiometric reduction (requiring equivalent amounts of reductant) to catalytic reduction (requiring sub-stoichiometric amounts of catalyst). This parameter change transforms the process from one that generates large amounts of metallic waste to one that produces minimal waste with high atom economy.

Inventive Principle:
Principle #35Parameter changes

3Object-affected harmful factors

If molecular hydrogen is used as reductant with conventional catalysts, then environmental friendliness is improved, but high pressure (200 atm) and high temperature (200°C or higher) are required

Engineering Contradiction:
Improveenvironmental impactVSAvoidhydrogen pressure
Core Design Contradiction:
Object-affected harmful factorsVSStress or pressure

Solution Approach 1:

The composite catalyst system of rhodium-molybdenum on hydroxyapatite creates synergistic effects that lower the activation energy barrier for hydrogenation. This enables the use of molecular hydrogen under environmentally friendly conditions (low pressure 1-30 atm and low temperature 50-150°C) while maintaining high reaction efficiency, eliminating the need for extreme conditions required by conventional catalysts.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The invention dramatically changes the operating parameters from extreme conditions (200 atm, 200°C) to mild conditions (1-30 atm, 50-150°C). This parameter optimization maintains the environmental advantages of using molecular hydrogen while making the process industrially viable with standard equipment and enhanced safety.

Inventive Principle:
Principle #35Parameter changes

4Productivity

If homogeneous catalysts are used for amide hydrogenation, then reaction activity is improved, but catalyst reuse becomes difficult

Engineering Contradiction:
Improvereaction activityVSAvoidcatalyst reusability
Core Design Contradiction:
ProductivityVSEase of repair

Solution Approach 1:

The patent uses hydroxyapatite as an intermediary support material that anchors the rhodium and molybdenum catalyst particles. This intermediary structure provides a solid support that maintains the high activity characteristics of homogeneous catalysts while enabling easy separation and reuse of the catalyst system through simple filtration or decantation, solving the reusability problem of homogeneous catalysts.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The porous hydroxyapatite support provides a high surface area for catalyst dispersion, maintaining high reaction activity similar to homogeneous catalysts. Simultaneously, the solid porous structure enables easy physical separation from the reaction mixture, allowing for catalyst recovery and reuse without the complexity associated with homogeneous catalyst systems.

Inventive Principle:
Principle #31Porous materials

5Stability of the object's composition

If conventional heterogeneous catalysts with silica carriers are used, then catalyst stability is improved, but conversion and yield are inferior

Engineering Contradiction:
Improvecatalyst stabilityVSAvoidconversion and yield
Core Design Contradiction:
Stability of the object's compositionVSProductivity

Solution Approach 1:

The patent creates a superior composite catalyst by combining rhodium and molybdenum metals with hydroxyapatite support. This composite structure provides both the stability of heterogeneous catalysts and enhanced catalytic activity for amide hydrogenation, achieving high conversion rates and yields (exceeding 90% in many cases) that surpass conventional silica-based heterogeneous catalysts while maintaining catalyst stability and reusability.

Inventive Principle:
Principle #40Composite materials

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 enables efficient hydrogenation of amides to amines under mild conditions, facilitating safe and inexpensive industrial synthesis while allowing for the reuse of expensive rhodium components, maintaining high activity and selectivity.

Implementation Method 1

a catalyst for use in a hydrogenation reaction that converts an amide compound into an amine compound

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 2

the catalyst containing rhodium and molybdenum that are supported on hydroxyapatite

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS12187691B2Hydrogenation catalyst used in amide compound hydrogenation and method for producing amine compound using same
Publication Date: 2025.01.07 N E CHEMCAT
  • US12187691B2 patent drawing
  • US12187691B2 patent drawing
  • US12187691B2 patent drawing

AI summary

Provided is a catalyst for amide compound hydrogenation characterized in that rhodium and molybdenum are supported on hydroxyapatite, the catalyst for amide compound hydrogenation providing a catalyst that can promote a reduction reaction that converts an amide compound into an amine compound, can be used under moderate conditions, and has durability that allows repeated use thereof while retaining high activity. Also provided is a method for producing an amine compound, the method being characterized by including bringing an amide compound into contact with the catalyst for amide compound hydrogenation to cause hydrogenation, thereby producing an amine compound.