Thioamide Reaction for Mercapto Synthesis Without Nitrogen Impurities

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Solution Overview

Problem

Existing methods for producing organic mercapto compounds using thiourea often result in nitrogen-containing impurities, complicating the process and requiring specialized equipment for waste treatment.

Innovation Solution

A method involving a reaction between an alcohol compound and a thioamide compound under acidic conditions to produce an organic mercapto compound, suppressing the formation of by-products and eliminating nitrogen-containing impurities.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If thiourea is used as a thiating agent to produce organic mercapto compound, then the production method is well-established and widely used, but nitrogen-containing impurities are generated requiring special waste treatment equipment

Engineering Contradiction:
Improveproduction methodVSAvoidwaste treatment equipment
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The invention extracts and eliminates the nitrogen-containing impurity source by replacing thiourea with a sulfur compound that does not contain nitrogen in the molecular structure, thereby removing the need for specialized waste treatment equipment while maintaining the thiating function

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention changes the chemical composition parameter of the thiating agent from nitrogen-containing (thiourea) to nitrogen-free (sulfur compound), fundamentally altering the waste stream characteristics and eliminating the need for complex waste treatment systems

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If thiourea is used as a thiating agent, then the reaction pathway is well-known, but the process becomes complicated due to nitrogen-containing impurities

Engineering Contradiction:
Improvereaction pathwayVSAvoidprocess complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The invention removes the problematic nitrogen-containing byproducts from the reaction system by substituting the thiating agent, thereby simplifying the overall process while retaining the effectiveness of the thiating reaction

Inventive Principle:
Principle #2Taking out (Extraction)

3Productivity

If conventional thiating methods are used, then organic mercapto compound can be produced, but by-products are generated reducing production efficiency

Engineering Contradiction:
Improveproduction efficiencyVSAvoidby-products
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The invention converts the harmful by-product generation into a benefit by selecting a thiating agent that produces no nitrogen-containing impurities, thereby improving production efficiency and eliminating substance loss to waste treatment

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

Solution Approach 2:

By changing the chemical nature of the thiating agent from nitrogen-containing to nitrogen-free, the invention fundamentally alters the reaction outcomes to eliminate by-product formation and improve overall productivity

Inventive Principle:
Principle #35Parameter changes

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 simplifies the production process, reduces the need for specialized equipment, and effectively minimizes the generation of unwanted by-products, resulting in a more efficient and cost-effective method for producing organic mercapto compounds.

Implementation Method 1

reacting an alcohol compound including a sulfur atom with a thioamide compound having a structure in which an organic group is bonded to at least one bonding hand of a thioamide group, under acidic conditions

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentUS11897835B2Method for producing organic mercapto compound or intermediate thereof, (poly)thiol component, polymerizable composition for optical material, molded product, optical material, and lens
Publication Date: 2024.02.13 MITSUI CHEMICALS INC
  • US11897835B2 patent drawing
  • US11897835B2 patent drawing
  • US11897835B2 patent drawing

AI summary

A method for producing an organic mercapto compound or an intermediate thereof according to the present invention has a reaction step of reacting an alcohol compound including a sulfur atom with a thioamide compound having a structure in which an organic group is bonded to at least one bonding hand of a thioamide group, under acidic conditions.