Chlorination of 3,3,3-Trifluoropropene Under Pressure

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Solution Overview

Problem

Current processes for producing 2,3,3-tetrafluoro-1-propene (HFO 1234yf) lack detailed descriptions of the chlorination step to form 2,3-dichloro-1,1,1-trifluoropropane (243db), a crucial precursor, and do not achieve high selectivity and yield effectively.

Innovation Solution

A process involving the chlorination of 3,3,3-trifluoropropene to 2,3-dichloro-1,1,1-trifluoropropane under pressures greater than 2 bars, preferably between 4 and 50 bars, in the liquid phase, without added catalysts, followed by dehydrochlorination and fluorination steps to produce 2,3,3-tetrafluoro-1-propene.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional chlorination processes are used to prepare 2,3-dichloro-1,1,1-trifluoropropane, then the process can be carried out under standard conditions, but the selectivity and yield are insufficient

Engineering Contradiction:
ImproveselectivityVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent applies parameter changes by conducting the chlorination reaction under elevated pressure conditions (greater than 2 bars, preferably 4-50 bars) and in the liquid phase, which fundamentally alters the reaction parameters from conventional atmospheric conditions. This pressure-induced parameter change achieves high selectivity (>90%) and conversion (>80%) for 2,3-dichloro-1,1,1-trifluoropropane without requiring complex catalyst systems or multi-step procedures

Inventive Principle:
Principle #35Parameter changes

2Manufacturing precision

If detailed chlorination procedures are implemented to improve selectivity, then manufacturing precision increases, but the process becomes more complex

Engineering Contradiction:
ImproveconversionVSAvoidprocess steps
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent achieves high conversion (>80%) through parameter changes specifically in pressure conditions and phase state, rather than through complex procedural steps. The simplified process requires only pressurizing the reaction system and maintaining liquid phase conditions, avoiding the need for multiple reaction steps, catalyst additions, or complex process controls that would increase device complexity

Inventive Principle:
Principle #35Parameter changes

3Productivity

If pressure is increased to improve reaction efficiency, then productivity increases, but equipment requirements and operational complexity increase

Engineering Contradiction:
Improvereaction efficiencyVSAvoidequipment requirements
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent optimizes productivity by implementing moderate pressure conditions (greater than 2 bars, preferably 4-50 bars) that are sufficient to achieve high reaction efficiency without requiring extreme pressure equipment. This parameter change enables the use of simpler pressure-resistant reactors rather than complex high-pressure apparatus, maintaining operational simplicity while achieving selectivity >90% and conversion >80%

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 process achieves high selectivity and yield for 243db and subsequently 1234yf, with selectivity greater than 90% and conversion greater than 80%, simplifying the chlorination step and improving the overall efficiency of the production process.

Implementation Method 1

The invention provides a process for the preparation of 2,3-dichloro-1,1,1-trifluoropropane by chlorination of 3,3,3-trifluoropropene at a pressure greater than 2 bars

Methodology Applied
Scientific EffectElectrophilic addition: Chemical Bonding

Implementation Method 2

followed by dehydrochlorination and fluorination steps to produce 2,3,3-tetrafluoro-1-propene

Methodology Applied
Scientific EffectDehydrochlorination: Chemical Bonding

Data Source

PatentUS8680346B2Process for the preparation of trifluorinated and tetrafluorinated compounds
Publication Date: 2014.03.25 ARKEMA FRANCE SA

AI summary

The subject of the invention is a process for the preparation of 2,3-dichloro-1,1,1-trifluoropropane by chlorination of 3,3,3-trifluoropropene at a pressure greater than 2 bar. Application in the synthesis of 1234yf.