Two-Step Fluorination of Chloropropenes for HFO Synthesis

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Solution Overview

Problem

Current methods for producing hydrofluoropropenes, such as HFO-1234yf, face challenges in efficiently converting chloropropene materials into environmentally friendly products with zero ozone depletion potential and low global warming potential, as they often require multiple catalyzed reactions and produce byproducts that need complex separation.

Innovation Solution

A two-step process involving liquid phase, noncatalytic fluorination of chloropropene to form hydrochlorofluoropropene, followed by gas phase, catalytic fluorination to produce hydrofluoropropene, using hydrogen fluoride and specific catalysts like chromium-based catalysts, with optimized reaction conditions to minimize byproducts and enhance conversion efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If a single catalyzed gas phase fluorination reaction is used to convert chloropropene to hydrofluoropropene, then the process is simpler, but the conversion efficiency is low and byproduct formation is high

Engineering Contradiction:
Improveprocess simplicityVSAvoidconversion efficiency
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

The patent divides the fluorination process into two distinct reaction stages: (1) liquid phase noncatalytic fluorination of chloropropene to form hydrochlorofluoropropene, and (2) gas phase catalytic fluorination of the intermediate to form the final hydrofluoropropene product. This segmentation allows each reaction to be optimized independently, achieving high conversion efficiency while maintaining process simplicity.

Inventive Principle:
Principle #1Segmentation

2Productivity

If multiple catalyzed reactions are used to produce hydrofluoropropene, then conversion efficiency improves, but the process complexity and separation requirements increase

Engineering Contradiction:
Improveconversion efficiencyVSAvoidprocess complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent changes the reaction parameters between the two stages: the first stage uses liquid phase conditions without catalyst at controlled temperature and pressure, while the second stage uses gas phase conditions with catalyst. This parameter change allows the first reaction to selectively form the intermediate with minimal byproducts, simplifying the overall process while maintaining high conversion efficiency.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If conventional fluorination methods are used, then byproduct formation occurs, but separation and recycling become complex and costly

Engineering Contradiction:
Improvebyproduct formationVSAvoidseparation complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent converts the potentially harmful HCl byproduct from the first reaction into a beneficial feature: the liquid phase noncatalytic fluorination selectively produces hydrochlorofluoropropene with high selectivity, and the HCl formed can be easily separated and recycled. The distinct physical properties of the liquid phase intermediate facilitate simple separation, turning a potential waste stream into a recyclable material and simplifying the overall process.

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

This process effectively converts 1,1,2,3-tetrachloropropene into hydrofluoropropene with high purity and low byproduct formation, allowing for efficient separation and recycling of co-products, thus addressing the environmental concerns and production inefficiencies of existing methods.

Implementation Method 1

liquid phase, noncatalytic fluorination of the tetrachloropropene to form a hydrochlorofluoropropene

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

gas phase, catalytic fluorination of the hydrochlorofluoropropene to form a hydrofluoropropene

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP2170785B1Process for the manufacture of hydrofluoroolefins
Publication Date: 2018.09.12 ARKEMA INC

AI summary

In this invention we are disclosing a process for the synthesis of hydrocchlorofluoro olefins (HCFO) and/or hydrofluoroolefins (HFO). The process is based on the following steps of liquid phase, noncatalytic fluorination of hydrochloropropenes to form hydrochlorofluoropropenes and/or hydrofluoropropenes, followed by gas phase, noncatalytic fluorination of the hydrochlorofluoropropenes to form hydrofluoropropenes.