Polyvalent Bismuth Catalyzed Chlorination of Alkanes

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Solution Overview

Problem

Current methods for preparing chlorinated alkane products, such as pentachloropropanes, are inefficient due to requiring multiple steps and extended reaction times, leading to increased economic costs and the need for refrigeration equipment.

Innovation Solution

A method involving the reaction of a chlorinated alkane substrate with a source of chlorine in the presence of a polyvalent bismuth compound, which results in a chlorinated alkane product with additional chlorine atoms, using a liquid phase reaction that can be either homogeneous or heterogeneous, and is performed as a batch or continuous process.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional methods are used to prepare chlorinated hydrocarbons, then the products can be obtained, but the process requires multiple steps and extended reaction times leading to increased economic costs

Engineering Contradiction:
Improvereaction timeVSAvoidnumber of steps
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent combines multiple reaction steps into a single chlorination reaction by using a polyvalent bismuth compound catalyst that enables direct conversion of chlorinated alkane substrates to highly chlorinated products in one operation, eliminating the need for sequential reaction steps required by conventional methods

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The invention changes the reaction parameters by introducing a polyvalent bismuth compound catalyst and conducting the reaction in the liquid phase at elevated temperatures (above the boiling point of the substrate), which fundamentally alters the reaction kinetics and enables single-step conversion with high productivity

Inventive Principle:
Principle #35Parameter changes

2Productivity

If conventional methods are used to prepare chlorinated hydrocarbons, then the products can be obtained, but refrigeration equipment is required which increases economic costs

Engineering Contradiction:
Improvereaction efficiencyVSAvoidreaction temperature
Core Design Contradiction:
ProductivityVSTemperature

Solution Approach 1:

The patent fundamentally changes the temperature parameter by conducting the chlorination reaction in the liquid phase at elevated temperatures above the boiling point of the chlorinated alkane substrate, eliminating the need for refrigeration equipment while maintaining high reaction efficiency and productivity

Inventive Principle:
Principle #35Parameter changes

3Manufacturing precision

If existing chlorination methods are used, then chlorinated products can be formed, but the reaction requires extended periods of time to complete

Engineering Contradiction:
ImproveselectivityVSAvoidreaction duration
Core Design Contradiction:
Manufacturing precisionVSDuration of action of moving object

Solution Approach 1:

The polyvalent bismuth compound acts as an intermediary catalyst that facilitates the chlorination reaction by providing an alternative reaction pathway with lower activation energy, enabling the reaction to proceed rapidly at elevated temperatures while maintaining high selectivity for the desired highly chlorinated products

Inventive Principle:
Principle #24Intermediary (Mediator)

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 reduces the number of steps and reaction time, improving efficiency and reducing costs by selectively forming chlorinated alkane products like 1,1,1,2,3-pentachloropropane with minimal byproduct formation, while maintaining the carbon backbone structure of the substrate.

Implementation Method 1

reaction of the chlorinated alkane substrate with a source of chlorine in the presence of one or more polyvalent bismuth compounds

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3060536B1Process for producing chlorinated hydrocarbons in the presence of a polyvalent bismuth compound
Publication Date: 2018.07.18 EAGLE US 2 LLC

AI summary

The preparation of chlorinated hydrocarbons by reacting a chlorinated alkane substrate, such as 1,1,1,3 tetrachloropropane, with a source of chlorine, such as chlorine (Cl2), in the presence of a polyvalent bismuth compound, such as triphenyl bismuth and/or triphenyl bismuth dichloride, is described. With the method of the present invention, the chlorinated alkane product has covalently bonded thereto at least one more chlorine group than the chlorinated alkane substrate, and the chlorinated alkane substrate and the chlorinated alkane product each have a carbon backbone structure that is in each case the same.