Asymmetrical Sulfide Synthesis via Solid Acid Catalysis

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Solution Overview

Problem

Existing methods for producing asymmetrical sulfide compounds often require harsh reaction conditions and result in significant byproducts, limiting yield and efficiency.

Innovation Solution

A process involving the contact of specific ether, sulfide, alcohol, or thiol compounds with a catalyst in a fixed bed reactor to form asymmetrical sulfide and ether compounds, utilizing a CoMo catalyst or γ-alumina to achieve high yield and minimal byproducts.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional synthesis techniques are used to produce asymmetrical sulfide compounds, then the synthesis can be performed with standard methods, but harsh or corrosive reaction conditions are required and significant byproducts are formed

Engineering Contradiction:
Improvesynthesis methodVSAvoidreaction byproducts
Core Design Contradiction:
Ease of manufactureVSObject-generated harmful factors

Solution Approach 1:

The patent employs an alumina-based solid acid catalyst as an intermediary to facilitate the reaction between thiol and ether compounds. This catalyst mediates the transthioetherification process, enabling the reaction to proceed under milder conditions without requiring harsh reagents, thereby reducing harmful byproduct formation while maintaining ease of manufacture

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the reaction parameters by using solid acid catalysis instead of conventional liquid acid catalysts. This parameter change allows the reaction to occur under milder conditions with reduced corrosion and fewer byproducts, while still maintaining practical manufacturability through straightforward catalyst handling and separation

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If conventional synthesis techniques are used to produce asymmetrical sulfide compounds, then the synthesis can be performed with standard methods, but harsh or corrosive reaction conditions are required

Engineering Contradiction:
Improvesynthesis methodVSAvoidreaction conditions
Core Design Contradiction:
Ease of manufactureVSTemperature

Solution Approach 1:

The alumina-based solid acid catalyst acts as an intermediary that enables the reaction to proceed at lower temperatures compared to conventional methods. The catalyst provides active sites that lower the activation energy barrier, allowing the transthioetherification to occur under milder thermal conditions while maintaining ease of manufacture

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent replaces conventional liquid acid catalyst systems with a solid acid catalyst system. This substitution eliminates the need for harsh liquid reagents and enables easier separation, while also allowing the reaction to proceed under milder conditions. The solid catalyst can be simply filtered off, replacing complex liquid handling and neutralization procedures

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

3Productivity

If conventional synthesis techniques are used, then synthesis can be performed, but significant byproducts are formed reducing yield

Engineering Contradiction:
ImproveyieldVSAvoidreaction byproducts
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The solid acid catalyst serves as an intermediary that selectively promotes the desired transthioetherification reaction while minimizing side reactions. This selective catalysis increases the yield of the desired asymmetrical sulfide compound by reducing the formation of unwanted byproducts, thereby improving productivity

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent converts the potential harm of byproduct formation into a benefit by using a selective solid acid catalyst that directs the reaction toward the desired product. The catalyst's specific active sites promote the main reaction pathway while suppressing side reactions, effectively converting what would be waste into useful product and improving overall yield

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

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 process achieves high conversion and yield of asymmetrical sulfide and ether compounds with minimal byproducts, such as mercaptans, and allows for efficient isolation and purification, particularly using γ-alumina as a catalyst.

Implementation Method 1

A process involving the contact of specific ether, sulfide, alcohol, or thiol compounds with a catalyst in a fixed bed reactor to form asymmetrical sulfide and ether compounds, utilizing a CoMo catalyst or γ-alumina to achieve high yield and minimal byproducts

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3878839B1Synthesis of asymmetrical sulfide compounds and asymmetrical ether compounds
Publication Date: 2024.07.24 CHEVRON PHILLIPS CHEMICAL COMPANY LP
  • EP3878839B1 patent drawingFigure 1
  • EP3878839B1 patent drawingFigure 2
  • EP3878839B1 patent drawingFigure 3

AI summary

The present invention discloses methods for synthesizing asymmetrical sulfide compounds and asymmetrical ether compounds from a variety of ether, sulfide, alcohol, and thiol reactants that are contacted in the presence of a suitable catalyst. Conversions of the limiting reactant to the desired asymmetrical sulfide or asymmetrical ether compound generally exceed 50%.