One-Step Trithiocarbonate Synthesis Without Solvent Washes

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Solution Overview

Problem

Traditional methods for producing trithiocarbonates suffer from low conversion rates, high waste generation, and low practical yields, making them unsuitable for large-scale commercial use due to the need for multi-step processes, solvent washes, and re-crystallization steps.

Innovation Solution

A one-step process involving the reaction of CS2, a haloform, and a ketone or aldehyde in the presence of a metal hydroxide base, without the need for solvent washes or re-crystallization, resulting in higher practical yields and purity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If traditional multi-step processes with solvent washes and re-crystallization are used, then product purity can be achieved, but practical yield is low (4.3% by weight or less) and process complexity is high

Engineering Contradiction:
Improveproduct purityVSAvoidpractical yield
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent combines multiple traditional steps (reaction, solvent wash, and re-crystallization) into a single integrated process. The reaction is performed in a solvent system that allows direct isolation of pure product without separate purification steps, achieving both high purity and high practical yield (more than double the traditional 4.3% maximum)

Inventive Principle:
Principle #5Merging (Combining)

2Manufacturing precision

If traditional multi-step processes are used, then product can be isolated as solid, but process complexity increases and waste generation increases

Engineering Contradiction:
Improveproduct isolation qualityVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent merges the reaction and isolation steps into a single operational sequence. The product is isolated directly from the reaction mixture through filtration or decantation without requiring separate solvent removal, washing, or re-crystallization steps, thereby reducing process complexity while maintaining product quality

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent extracts the product directly from the reaction mixture in a simplified manner. By using a solvent system where the product has specific solubility characteristics, the product can be directly precipitated or filtered out without needing complex purification infrastructure

Inventive Principle:
Principle #2Taking out (Extraction)

3Productivity

If reagents are charged in large excess to drive reaction, then conversion rate improves, but practical yield decreases due to excess material waste

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

Solution Approach 1:

The patent optimizes the stoichiometric ratios of reactants to achieve high conversion without requiring large excesses. By carefully controlling the molar ratios and reaction conditions (temperature, time, catalyst), the process achieves high conversion rates while minimizing unreacted starting materials that would need to be discarded

Inventive Principle:
Principle #35Parameter changes

4Manufacturing precision

If solvent washes and re-crystallization steps are used, then product purity is improved, but time consumption increases and cost increases

Engineering Contradiction:
Improveproduct purityVSAvoidprocess time
Core Design Contradiction:
Manufacturing precisionVSLoss of time

Solution Approach 1:

The patent combines purification objectives into the main reaction step by selecting a solvent system that facilitates direct product isolation. This eliminates the need for sequential purification operations, reducing both time and cost while achieving the required purity level

Inventive Principle:
Principle #5Merging (Combining)

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 significantly higher practical yields and purity of trithiocarbonates, making them suitable for large-scale commercial production while reducing waste generation and process complexity.

Implementation Method 1

The first step combines carbon disulfide and a base to form an intermediate trithio structure

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

the second step combines the intermediate with a haloform, a ketone and additional base

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentEP2178832B1Process for making substituted trithiocarbonate derivatives
Publication Date: 2018.01.17 THE LUBRIZOL CORP
  • EP2178832B1 patent drawing
  • EP2178832B1 patent drawing
  • EP2178832B1 patent drawing

AI summary

The present invention provides a low cost technique for synthesizing substituted trithiocarbonates and derivates thereof, by a one-step process which does not require solvent washes or re-crystallization steps, and results in practical yields more than double that of processes disclosed in the prior art.