Oxyborane Synthesis via Organic Catalysts

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Solution Overview

Problem

Current methods for converting CO2 into oxyborane compounds using hydroboration reactions face challenges due to the high thermodynamic stability of CO2, requiring effective catalysts that are often expensive and toxic, and lack efficient, selective, and cost-effective options for producing methane derivatives like formic acid, formaldehyde, and methanol.

Innovation Solution

A process involving the reaction of hydroborane with CO2 in the presence of catalysts such as organic bases, boron compounds, or aluminum compounds, which overcome the limitations of traditional metal catalysts by providing a selective and efficient conversion of CO2 to oxyborane compounds, allowing for the production of methane derivatives with good yield and selectivity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If traditional metal catalysts are used for hydroboration of CO2, then the conversion efficiency is improved, but the cost and toxicity increase

Engineering Contradiction:
Improveconversion efficiencyVSAvoidtoxicity and cost
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent replaces expensive and toxic metal catalysts with organic catalysts that are cheaper, less toxic, and can be easily disposed of or regenerated. The organic catalysts include compounds with nitrogen, phosphorus, sulfur, or oxygen atoms that form transient complexes with CO2 during the hydroboration reaction, enabling efficient conversion without the harmful effects of metal catalysts.

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

Solution Approach 2:

The patent introduces organic compounds as intermediary catalysts that mediate between CO2 and hydroborane reagents. These organic catalysts form intermediate complexes that facilitate the hydroboration reaction, providing an alternative pathway that avoids direct use of toxic metal catalysts while maintaining high conversion efficiency.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Quantity of substance

If CO2 is converted to oxyborane compounds, then the value as carbon source is improved, but the thermodynamic stability of CO2 makes the reaction difficult

Engineering Contradiction:
Improvevalue as carbon sourceVSAvoidreaction feasibility
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The patent employs organic catalysts that change the reaction parameters by providing alternative reaction pathways with lower activation energies. The catalysts modify the electronic and steric parameters of the reaction system, enabling the thermodynamically stable CO2 to undergo hydroboration at practical rates and conditions, thus converting valuable CO2 into useful oxyborane compounds.

Inventive Principle:
Principle #35Parameter changes

3Manufacturing precision

If selective catalysts are developed for CO2 functionalization, then the production of specific methane derivatives is improved, but the catalyst development complexity increases

Engineering Contradiction:
Improveselectivity for methane derivativesVSAvoidcatalyst development complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent uses organic catalysts with specific local functional groups (nitrogen, phosphorus, sulfur, or oxygen atoms) that provide selective interaction with CO2 and hydroborane reagents. These localized functional groups enable high selectivity for producing specific methane derivatives (formic acid, formaldehyde, methanol) without requiring complex catalyst systems, as the selective interaction occurs at specific molecular sites.

Inventive Principle:
Principle #3Local quality

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 process achieves a high yield (50-100%) and selectivity in producing oxyborane compounds, which can be further converted into methane derivatives like formic acid, formaldehyde, and methanol, using non-toxic and cost-effective catalysts, and also enables the preparation of labelled compounds for various applications.

Implementation Method 1

The reaction between CO2 and a hydroborane, which takes place in two stages, results in advantageous synthetic intermediates of formoxysilane, bis(silyl)acetals and methoxysilanes

Methodology Applied
Scientific EffectHydroboration: Chemical Bonding

Implementation Method 2

The catalytic reduction of CO2 to give formic acid HCOOH, formaldehyde H2CO, methanol CH3OH and methane CH4 is arousing increasing interest

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS9890180B2Method for preparing oxyborane compounds
Publication Date: 2018.02.13 COMMISSARIAT A LENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES
  • US9890180B2 patent drawing
  • US9890180B2 patent drawing
  • US9890180B2 patent drawing

AI summary

A method for preparing oxyborane compounds of formula (I): using carbon dioxide, and the use of the oxyborane compounds obtained in this way for preparing methane derivatives, in particular oxygenated, halogenated or amino derivatives of methane. The methane derivatives obtained in this way can then be used in the production of vitamins, pharmaceutical products, glues, acrylic fibers and synthetic leathers, pesticides, and fertilizers, for example. Also provided is a method for producing vitamins, pharmaceutical products, glues, acrylic fibers, synthetic leathers, pesticides, and fertilizers, for example, including a step of preparing methane derivatives, in particular oxygenated, halogenated or amino derivatives of methane, from oxyborane compounds obtained by the method according to the invention. Further provided is a method of preparing labelled oxyborane compounds and the use of same.