Integrated Dehydrochlorination and Isomerization for Trans-1233zd Yield

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Solution Overview

Problem

The production of trans-1233zd from 243fa is hindered by the generation of a cis-isomer as a by-product, reducing the single pass yield, and existing methods do not integrate cis-1233zd isomerization with dehydrochlorination in a continuous process.

Innovation Solution

A continuous, integrated process involving vapor phase dehydrochlorination of 243fa with a catalyst to produce a mixture of trans and cis-1233zd, followed by optional HCl recovery, isomerization of cis-1233zd into trans-1233zd using suitable catalysts, and final isolation of trans-1233zd.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If dehydrochlorination of 243fa is conducted to produce trans-1233zd, then the desired product is obtained, but a cis-isomer by-product is generated which reduces the single pass yield

Engineering Contradiction:
Improvesingle pass yield of trans-1233zdVSAvoidamount of cis-1233zd by-product
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The patent applies this principle by converting the harmful cis-1233zd by-product into a beneficial feedstock for producing more trans-1233zd. The process integrates a cis-trans isomerization reactor that converts cis-1233zd into trans-1233zd, thereby transforming the waste by-product into valuable product and improving overall yield.

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

Solution Approach 2:

The patent merges two previously separate processes (dehydrochlorination and cis-trans isomerization) into a single integrated continuous process. The dehydrochlorination reactor and cis-trans isomerization reactor are connected in series, allowing the product stream from the first reactor to directly feed into the second reactor, combining multiple functions into one streamlined process.

Inventive Principle:
Principle #5Merging (Combining)

2Productivity

If existing dehydrochlorination methods are used, then trans-1233zd is produced, but the process lacks integration with cis-1233zd isomerization

Engineering Contradiction:
Improveoverall production efficiencyVSAvoidprocess integration complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent combines the dehydrochlorination process and cis-trans isomerization process into one integrated flow. The product stream from the dehydrochlorination reactor is directly fed into the cis-trans isomerization reactor, merging two unit operations into a continuous integrated process that improves efficiency without requiring complex intermediate handling.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent implements a continuous process where the output from the dehydrochlorination reactor continuously feeds into the isomerization reactor, and the purified trans-1233zd is continuously produced. This continuous operation eliminates batch processing interruptions and maintains steady-state operation throughout the integrated system.

Inventive Principle:
Principle #20Continuity of useful 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

This process enhances the yield of trans-1233zd by effectively converting cis-1233zd into trans-1233zd, improving the efficiency of the production process and achieving high selectivity and conversion rates.

Implementation Method 1

dehydrochlorinating 1,1,1-trifluoro-3,3-dichloropropane (243fa) in the vapor phase with a catalyst in a reactor to thereby produce a product stream comprising cis-1-chloro-3,3,3-trifluoropropene, trans-1-chloro-3,3,3-trifluoropropene and hydrogen chloride

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

isomerizing at least a portion of the cis-1-chloro-3,3,3-trifluoropropene into trans-1-chloro-3,3,3-trifluoropropene

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP2699534B1PROCESS FOR PRODUCING TRANS-1233zd
Publication Date: 2018.01.24 HONEYWELL INTERNATIONAL INC

AI summary

Trans-1233zd, the trans-isomer of 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) can be used as blowing agents, solvents, cleaning agents, as well as monomers of macromolecule compounds, and can be prepared through the dehydrochlorination of 1,1,1-trifluoro-3,3-dichloropropane (HCFC-243fa) with the help of a catalyst. The present invention is directed to an integrated process is proposed to produce trans-1233zd from 243fa, which is consisted of the following four major unit operations: (1) Catalytic dehydrochlorination of 243fa into trans/cis-1233zd, (2) HCl recovery, (3) Catalytic isomerization of cis-1233zd into trans-1233zzd, and (4) Isolation of trans-1233zd.