Isomerization of 1233zd Without Reagents

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Solution Overview

Problem

There is a need for processes that selectively provide one or both of the commercially desirable isomers of 1-chloro-3,3,3-trifluoropropene (1233zd), as the two isomers have different physical properties making them suitable for specific applications, and existing isomerization reactions often require reagents.

Innovation Solution

A process involving a feed stream of 1233zd(E) or a mixture of 1233zd(E) and 1233zd(Z) being contacted with a heated surface, maintained between 150°C and 400°C, to convert at least a portion of 1233zd(E) to 1233zd(Z) or vice versa, using a packing material such as stainless steel or a catalyst like metal oxide, without the need for reagents, followed by separation to isolate the isomers.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If existing isomerization reactions are used to convert between 1233zd isomers, then isomer conversion can be achieved, but reagents are required which complicates the process and increases cost

Engineering Contradiction:
Improveprocess simplicityVSAvoidreagent requirement
Core Design Contradiction:
Ease of manufactureVSQuantity of substance

Solution Approach 1:

The invention extracts and removes the reagent component from the isomerization process. By using a heated surface (150-400°C) as the sole means to drive isomerization, the process eliminates the need for chemical reagents that would otherwise be required to facilitate the conversion between 1233zd(E) and 1233zd(Z) isomers.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The process enables the feed stream to isomerize itself through contact with the heated surface. The thermal energy from the heated surface provides sufficient activation energy for the isomerization reaction to proceed without external chemical assistance, allowing the system to serve itself rather than requiring reagent input.

Inventive Principle:
Principle #25Self-service

2Manufacturing precision

If isomerization is performed to produce pure isomers, then product purity is improved, but separation operations are required which increase process complexity

Engineering Contradiction:
Improveisomer purityVSAvoidseparation operation complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention changes the temperature parameter of the heated surface (maintained at 150-400°C) to control the isomerization equilibrium and kinetics. By optimizing this temperature parameter, the process achieves favorable isomer ratios that simplify downstream separation requirements while maintaining high product purity.

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 allows for the efficient conversion and separation of 1233zd(E) and 1233zd(Z) isomers, producing high purity streams suitable for various industrial applications, such as refrigerants, propellants, and solvents, without the use of reagents, thereby addressing the need for selective isomer production.

Implementation Method 1

contacting the feed stream with a heated surface that is maintained between 150°C and 400° C. The feed stream is contacted with the heated surface for a period of time sufficient to convert at least a portion of the 1233zd(E) to 1233zd(Z)

Methodology Applied
Scientific EffectThermal energy transfer: Heating

Implementation Method 2

The packing material is stainless steel, or is a catalyst material comprising a metal oxide, a halogenated metal oxide, a Lewis acid metal halide, or a zero-valent metal

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP2379474B1Isomerization of 1-chloro-3,3,3-trifluoropropene
Publication Date: 2015.01.14 HONEYWELL INTERNATIONAL INC

AI summary

Disclosed are processes for an isomerization reaction between (E)1-chloro-3,3,3-trifluoropropene and (Z)1-chloro-3,3,3-trifluoropropene. Some of the disclosed processes include the step of contacting a feed stream with a heated surface, where the feed stream includes (E)1-chloro-3,3,3-trifluoropropene, (Z)1-chloro-3,3,3-trifluoropropene or mixtures thereof. The resulting product stream includes (E)1-chloro-3,3,3-trifluoropropene and (Z)1-chloro-3,3,3-trifluoropropene, where the ratio of (E) isomer to (Z) isomer in the product stream is different than the ratio feed stream. The (E) and (Z) isomers in the product stream may be separated from one another.