Heterogeneous Catalyst for Cyclic Carbonate Synthesis

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Solution Overview

Problem

Current methods for synthesizing cyclic carbonates using homogeneous catalysts are complex, prone to catalyst degradation, and result in byproduct formation, with heterogeneous catalysts requiring high temperatures and excess silane compounds, leading to reduced catalytic activity and increased production costs.

Innovation Solution

A heterogeneous catalyst is produced by reacting a silane compound with a silica gel having low adsorbed water content, followed by treatment with a tertiary phosphine, achieving a molar ratio of halogen to phosphorus between 0.8 and 1.6, which simplifies the production process and enhances catalytic activity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a homogeneous catalyst is used for cyclic carbonate synthesis, then the catalytic activity is high, but the separation process becomes complicated and catalyst degradation occurs

Engineering Contradiction:
Improvecatalytic activityVSAvoidseparation process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The catalyst is extracted from the homogeneous phase and immobilized onto a solid support material, creating a heterogeneous catalyst system. This allows the catalyst to be easily separated from the reaction mixture by simple filtration, eliminating the complex distillation process required for homogeneous catalysts while maintaining catalytic activity.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The catalyst is localized on the surface of solid support particles, creating regions of high catalytic activity at the solid-liquid interface. The support material provides a large surface area with dispersed active sites, concentrating the catalytic function in specific locations while maintaining overall system stability and ease of separation.

Inventive Principle:
Principle #3Local quality

2Device complexity

If a heterogeneous catalyst with quaternary phosphonium group is used, then the separation process is simplified, but high temperature and long reaction time are required for catalyst production

Engineering Contradiction:
Improveseparation process complexityVSAvoidcatalyst production time
Core Design Contradiction:
Device complexityVSLoss of time

Solution Approach 1:

The reaction conditions for catalyst production are optimized by adjusting parameters such as temperature, reaction time, and reactant ratios. The patent identifies specific parameter ranges that achieve complete quaternary phosphonium formation while minimizing production time and energy consumption, resolving the contradiction between simplified separation and production efficiency.

Inventive Principle:
Principle #35Parameter changes

3Manufacturing precision

If a large excess amount of silane compound is used to introduce sufficient haloalkyl chain, then the surface modification is complete, but condensate formation increases and catalytic activity decreases

Engineering Contradiction:
Improvesurface modification completenessVSAvoidcatalytic activity
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

Instead of using a large excess of silane compound, the patent employs a controlled, stoichiometric amount of silane reactant. This partial action approach prevents excessive condensate formation that would block active sites, while still achieving sufficient surface modification to create an effective heterogeneous catalyst with maintained catalytic activity.

Inventive Principle:
Principle #16Partial or excessive action

4Productivity

If repeated distillation operations are performed to raise silane compound concentration, then the reaction efficiency improves, but the number of steps and system complexity increase

Engineering Contradiction:
Improvereaction efficiencyVSAvoidreaction system complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent performs preliminary optimization of the silane compound concentration and reaction conditions before initiating the main reaction. By pre-establishing the optimal reactant ratio and reaction parameters, the need for repeated distillation operations is eliminated, maintaining high reaction efficiency while simplifying the overall reaction system and reducing operational complexity.

Inventive Principle:
Principle #10Preliminary action

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 method allows for the efficient and cost-effective synthesis of cyclic carbonates with high conversion rates and yields, minimizing byproduct formation and improving catalytic performance.

Implementation Method 1

a silica gel in which a haloalkyl chain or a haloaryl chain is immobilized by a covalent bond

Methodology Applied
Scientific EffectCovalent bonding: Chemical Bonding

Implementation Method 2

reacting a trialkyl phosphine and a commercially available carrier in which a haloalkyl chain is immobilized to a silica gel via a covalent bond to form a quaternary phosphonium product

Methodology Applied
Scientific EffectQuaternization reaction: Chemical Bonding

Implementation Method 3

A heterogeneous catalyst is produced by reacting a silane compound with a silica gel having low adsorbed water content, followed by treatment with a tertiary phosphine, achieving a molar ratio of halogen to phosphorus between 0.8 and 1.6, which simplifies the production process and enhances catalytic activity

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP2990113B1Method for producing catalyst for cyclic carbonate synthesis
Publication Date: 2020.03.25 MARUZEN PETROCHEMICAL CO LTD
  • EP2990113B1 patent drawingFigure 1A~1
  • EP2990113B1 patent drawing
  • EP2990113B1 patent drawing

AI summary

Provided are : a method for easily producing a heterogeneous catalyst having excellent catalytic activity at a low cost, said heterogeneous catalyst being used for the purpose of synthesizing a cyclic carbonate by subjecting to a reaction an epoxide and carbon dioxide; a catalyst which is obtained by this production method; and a method for synthesizing a cyclic carbonate with use of this catalyst. A method for producing a catalyst that is used for the purpose of synthesizing a cyclic carbonate by subjecting to a reaction an epoxide with carbon dioxide, said method comprising the following steps (a) and (b): (a) a step of obtaining a catalyst precursor having a haloalkyl group or a haloaryl group, by subjecting to a reaction a silane compound having a haloalkyl group or a haloaryl group and a silica gel having an amount of adsorbed water of 1% by mass or less and (b) a step of obtaining a catalyst for cyclic carbonate synthesis, by subjecting to a reaction the catalyst precursor obtained in step (a) and a tertiary phosphine, in which the molar ratio of the halogen content to the phosphorus content, namely [halogen]/[phosphorus] is from 0.8 to 1.6.