Catalytic Conversion of HCFO-1233zd Mixtures Without Distillation Loss

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Solution Overview

Problem

The separation and utilization of HCFO-1233zd(Z) and HCFC-244fa mixtures are challenging due to similar boiling points and azeotrope-like properties, leading to yield losses and increased manufacturing costs, as they are typically destroyed, which is inefficient and costly.

Innovation Solution

A catalytic process using chromium-based catalysts like chromium trifluoride converts HCFO-1233zd(Z) and HCFC-244fa to HCFO-1233zd(E) through isomerization and dehydrohalogenation in a vapor phase, allowing simultaneous conversion and separation of components.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional distillation techniques are used to separate HCFO-1233zd(Z) and HCFC-244fa, then separation is attempted, but the process fails due to similar boiling points and azeotrope-like properties

Engineering Contradiction:

Improveseparation efficiencyVSAvoidseparation difficulty

Core Design Contradiction:

Manufacturing precisionVSDifficulty of detecting and measuring

Solution Approach 1:

The invention changes the separation approach from physical distillation (based on boiling point differences) to chemical transformation. By converting HCFC-244fa to HCFO-1233zd(E) through catalytic dehydrohalogenation, the process transforms the separation problem into a chemical reaction problem, overcoming the limitation of similar boiling points and azeotrope formation

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention converts the harmful toxic byproduct HCFC-244fa into a valuable product HCFO-1233zd(E). Instead of dealing with the difficulty of separating and disposing of toxic HCFC-244fa, the process transforms it into the desired HCFO-1233zd(E) product, turning a waste disposal problem into a production opportunity

Inventive Principle:

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

2Object-generated harmful factors

If HCFO-1233zd(Z) and HCFC-244fa mixtures are transported to thermal oxidizer for destruction, then waste is eliminated, but manufacturing costs increase

Engineering Contradiction:

Improvetoxic waste eliminationVSAvoidmanufacturing cost

Core Design Contradiction:

Object-generated harmful factorsVSEase of manufacture

Solution Approach 1:

The invention converts the toxic byproduct HCFC-244fa from a waste stream requiring expensive destruction into a valuable chemical feedstock. Through catalytic dehydrohalogenation, HCFC-244fa is transformed into HCFO-1233zd(E), which has commercial value as a refrigerant and blowing agent, thereby eliminating disposal costs and creating additional revenue

Inventive Principle:

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

Solution Approach 2:

Instead of discarding HCFC-244fa through thermal oxidation, the invention recovers it by converting it into HCFO-1233zd(E). The catalytic process selectively transforms HCFC-244fa while preserving HCFO-1233zd(Z), allowing both components to be valorized - HCFO-1233zd(Z) through isomerization and HCFC-244fa through dehydrohalogenation

Inventive Principle:

Principle #34Discarding and recovering

3Productivity

If HCFO-1233zd(Z) is produced as a by-product in fluorination of HCC-240fa, then HCFO-1233zd(E) production is achieved, but yield is reduced due to formation of HCFO-1233zd(Z) and HCFC-244fa

Engineering Contradiction:

ImproveHCFO-1233zd(E) production rateVSAvoidyield loss

Core Design Contradiction:

ProductivityVSLoss of substance

Solution Approach 1:

The invention implements a continuous conversion process where HCFO-1233zd(Z) and HCFC-244fa are continuously transformed into HCFO-1233zd(E). The two-step catalytic process (isomerization followed by dehydrohalogenation) ensures that both by-products are continuously converted, maximizing overall yield and eliminating the need for separate disposal operations

Inventive Principle:

Principle #20Continuity of useful action

Solution Approach 2:

The invention merges two separate chemical transformations (isomerization of HCFO-1233zd(Z) and dehydrohalogenation of HCFC-244fa) into a single integrated process. Both by-products are converted simultaneously in sequence through the same catalytic system, optimizing resource utilization and simplifying the overall process flow

Inventive Principle:

Principle #5Merging (Combining)

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

Achieves high conversion rates of HCFO-1233zd(Z) to HCFO-1233zd(E) (88-96%) and HCFC-244fa to HCFO-1233zd(E) (90-99%), with selectivity up to 97%, reducing waste and manufacturing costs by valorizing the by-products.

Implementation Method 1

reacting a mixture including HCFO-1233zd(Z) and HCFC-244fa in a vapor phase in the presence of a catalyst to simultaneously isomerize HCFO-1233zd(Z) to form HCFO-1233zd(E)

Methodology Applied

Scientific EffectCatalysis: Catalysis

Implementation Method 2

dehydrohalogenate HCFC-244fa to form HCFO-1233zd(E)

Methodology Applied

Scientific EffectCatalysis: Catalysis

Data Source

PatentUS20260078073A1PROCESS FOR CATALYTIC CONVERSION OF MIXTURES OF HCFO-1233zd(Z) AND HCFC-244fa INTO HCFO-1233zd(E)

Publication Date: 2026.03.19 SOLSTICE ADVANCED MATERIALS US INC

AI summary

A method for conversion of a composition containing HCFO-1233zd(Z) and HCFC-244fa to form HCFO-1233zd(E) by reacting a mixture including HCFO-1233zd(Z) and HCFC-244fa in a vapor phase in the presence of a catalyst to simultaneously isomerize HCFO-1233zd(Z) to form HCFO-1233zd(E) and dehydrohalogenate HCFC-244fa to form HCFO-1233zd(E). The catalyst may be a chromium-based catalyst such as chromium trifluoride, chromium oxyfluoride, or chromium oxide, for example.