Terminally Iodized Polyfluoroalkane Production via Low-Temperature Telomerization

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Solution Overview

Problem

Existing methods for telomerizing fluorine-containing olefins under high temperature and pressure conditions are energy-intensive and lead to corrosion, while compounds with perfluoroalkyl groups of 8 carbon atoms or more have high bioaccumulation potential, posing environmental concerns.

Innovation Solution

A method for producing terminally iodized polyfluoroalkanes with perfluoroalkyl groups of 6 or less carbon atoms by reacting perfluoroalkyl iodides with tetrafluoroethylene in the presence of a peroxide initiator, allowing for the formation of compounds with low bioaccumulation potential and easy decomposition, and reducing energy consumption and corrosion by performing the reaction at lower temperatures and pressures.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If telomerization is performed under high temperature and high pressure conditions, then the reaction rate and productivity are improved, but energy consumption increases and facility corrosion becomes serious

Engineering Contradiction:
Improvereaction rateVSAvoidenergy consumption
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

The patent changes the temperature and pressure parameters from high conditions to mild conditions (room temperature or slightly elevated temperature, atmospheric or slightly elevated pressure) by using a peroxide initiator that decomposes at low temperatures to generate radicals, thereby initiating telomerization without requiring high energy input while maintaining acceptable reaction rates

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces the mechanical/thermal activation method (high temperature and pressure) with a chemical activation method using peroxide initiators that decompose to generate radicals at low temperatures, substituting thermal energy input with chemical energy from peroxide decomposition

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

2Productivity

If telomerization is performed under high temperature and high pressure conditions, then the reaction rate is improved, but facility corrosion becomes serious and renewal frequency increases

Engineering Contradiction:
Improvereaction rateVSAvoidfacility corrosion
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the operating parameters from high temperature and pressure to mild conditions, which prevents the formation of hydrofluoric acid and other corrosive byproducts that occur under extreme conditions, thereby protecting facilities from corrosion

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent converts the potential harm of peroxide decomposition (which could lead to uncontrolled reactions) into a benefit by carefully selecting peroxide initiators that decompose at controlled low temperatures, generating radicals that drive telomerization under mild conditions without causing facility corrosion

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

3Quantity of substance

If compounds with perfluoroalkyl groups having 8 or more carbon atoms are produced, then the desired telomerization product is obtained, but bioaccumulation potential increases and environmental problems occur

Engineering Contradiction:
Improvetelomerization productVSAvoidbioaccumulation potential
Core Design Contradiction:
Quantity of substanceVSObject-generated harmful factors

Solution Approach 1:

The patent changes the product specification parameter from perfluoroalkyl groups with 8 or more carbon atoms to perfluoroalkyl groups with 7 or less carbon atoms by controlling the telomerization reaction conditions and monomer-to-initiator ratio, thereby producing compounds with lower bioaccumulation potential while still achieving the desired telomerization products

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses an excess of fluorine-containing olefin monomer relative to the peroxide initiator to ensure that the chain growth is limited to producing perfluoroalkyl groups with 7 or less carbon atoms, preventing over-polymerization that would lead to longer chains with higher bioaccumulation potential

Inventive Principle:
Principle #16Partial or excessive 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

The method effectively produces terminally iodized polyfluoroalkanes with low bioaccumulation potential, enabling easy decomposition and reducing environmental disturbance, while also lowering energy consumption and facility maintenance costs by using less expensive materials and reducing corrosion.

Implementation Method 1

reacting a perfluoroalkyl iodide with a fluorine-containing olefin in the presence of a peroxide initiator

Methodology Applied
Scientific EffectRadical generation through peroxide decomposition: Decomposition (biological)

Implementation Method 2

telomerizing a fluorine-containing olefin represented by general formula (1) to a perfluoroalkyl iodide represented by general formula (3) in the presence of a peroxide initiator

Methodology Applied
Scientific EffectTelomerization reaction: Chemical Bonding

Data Source

PatentEP2192100B1Terminally iodized polyfluoroalkane and method for producing the same
Publication Date: 2016.02.24 UNIMATEC CO LTD

AI summary

Provided is a terminally iodized polyfluoroalkane represented by the general formula: (in the formula, X and Y are each a hydrogen atom or a fluorine atom, wherein when Y is a fluorine atom, X is also a fluorine atom; n is an integer of 1 to 6; s+p is an integer of 1 to 5 and denotes the number of CHXCFY group; and t+r is 0 or an integer of 1 to 6 and denotes the number of tetrafluoroethylene skeleton). The terminally iodized polyfluoroalkane is produced by telomerizing a fluorine-containing olefin CHX=CFY and tetrafluoroethylene, successively, to CnF2n+1I in the presence of a peroxide initiator.