1233yd Production via Selective Dehydrofluorination

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Solution Overview

Problem

Current methods for producing 1-chloro-2,3,3-trifluoropropene (1233yd) suffer from low selectivity and high by-product formation due to the dehydrofluorination of starting compounds with multiple hydrogen atoms, making it difficult to separate and purify the desired product.

Innovation Solution

Dehydrofluorinating 3-chloro-1,1,2,2-tetrafluoropropane in the presence of an alkali or base compound as an accelerator, either in a liquid or gas phase, with a catalyst, to achieve high selectivity and conversion of 1233yd while suppressing the production of toxic by-products like 3-chloro-1,1,2-trifluoropropene.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If dehydrofluorination is performed on starting compounds with multiple hydrogen atoms, then conversion of the starting compound is improved, but selectivity of 1233yd deteriorates due to multiple by-products

Engineering Contradiction:
Improveconversion of starting compoundVSAvoidselectivity of 1233yd
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent applies local quality by selecting a specific starting compound (3-chloro-1,1,2,2-tetrafluoropropane) with a particular hydrogen atom arrangement that enables selective dehydrofluorination. The molecular structure has hydrogen atoms at specific positions (C1 and C3) that can be selectively eliminated to form the desired double bond at C2-C3, avoiding formation of isomeric by-products. This local structural characteristic ensures high selectivity while maintaining good conversion.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent employs parameter changes by optimizing reaction conditions including temperature range (50-150°C), pressure conditions, and catalyst selection to achieve both high conversion and high selectivity. The dehydrofluorination reaction parameters are carefully controlled to favor the formation of 1233yd over other possible products, resolving the contradiction between conversion and selectivity.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If multiple by-products are produced during dehydrofluorination, then conversion of starting compound is improved, but ease of separation and purification deteriorates

Engineering Contradiction:
Improveconversion of starting compoundVSAvoidseparation and purification
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

By selecting a starting compound with specific local structural characteristics (3-chloro-1,1,2,2-tetrafluoropropane), the patent ensures that dehydrofluorination produces primarily the desired 1233yd with minimal isomeric by-products. The specific arrangement of hydrogen atoms in the starting material allows selective elimination to form only the C2-C3 double bond, avoiding formation of C1-C2 or C3-C4 double bonds that would create separable by-products.

Inventive Principle:
Principle #3Local quality

3Ease of manufacture

If dehydrofluorination is performed without specific starting compound selection, then ease of manufacture is improved, but harmful factors increase due to toxic by-products

Engineering Contradiction:
Improveease of productionVSAvoidtoxic by-products
Core Design Contradiction:
Ease of manufactureVSObject-generated harmful factors

Solution Approach 1:

The patent addresses harmful factors by selecting a starting compound (3-chloro-1,1,2,2-tetrafluoropropane) with specific local structural features that prevent formation of toxic by-products. The molecular structure ensures that dehydrofluorination occurs selectively to form 1233yd without generating highly toxic isomers, thus maintaining ease of manufacture while eliminating harmful by-products.

Inventive Principle:
Principle #3Local quality

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

The method enables high conversion and selectivity of 1233yd, effectively suppressing the production of 3-chloro-1,1,2-trifluoropropene as a by-product, allowing for efficient and cost-effective production of 1233yd suitable for use as a heat transfer medium.

Implementation Method 1

dehydrofluorinating 3-chloro-1,1,2,2-tetrafluoropropane in the presence of an alkali or base compound as an accelerator

Methodology Applied
Scientific EffectDehydrofluorination reaction: Chemical Bonding

Implementation Method 2

with a catalyst, to achieve high selectivity and conversion of 1233yd

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3263544B1Method for producing 1-chloro-2,3,3-trifluoropropene
Publication Date: 2020.04.01 DAIKIN INDUSTRIES LTD

AI summary

The present invention provides a method for producing 1233yd that enables high conversion of the starting compound and high selectivity of 1233yd. The present invention provide a method for producing 1-chloro-2,3,3-trifluoropropene (1233yd), comprising the step of dehydrofluorinating 3-chloro-1,1,2,2-tetrafluoropropane (244ca).