HCFO-1233yd Purification via Basic Aqueous Extraction

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing methods for producing 1-chloro-2,3,3-trifluoropropene (HCFO-1233yd) do not effectively remove 1-chloro-3,3-difluoro-1-propyne and oxide by-products, which can impair the reliability and stability of the compound when used as cleaning agents, solvents, refrigerants, or aerosols.

Innovation Solution

A method involving contact of the composition containing HCFO-1233yd with a basic aqueous solution, preferably an alkali metal hydroxide or ammonia solution, at temperatures between 10°C to 60°C, to dissolve and remove 1-chloro-3,3-difluoro-1-propyne and oxide, thereby purifying HCFO-1233yd.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If HCFO-1233yd is produced by reacting 3-chloro-1,1,2,2-tetrafluoropropane with hydrogen fluoride in a vapor phase, then HCFO-1233yd is obtained as a product, but 1-chloro-3,3-difluoro-1-propyne and oxide are produced as by-products that cannot be effectively removed

Engineering Contradiction:
ImproveHCFO-1233yd productionVSAvoid1-chloro-3,3-difluoro-1-propyne and oxide by-products
Core Design Contradiction:
Quantity of substanceVSObject-generated harmful factors

Solution Approach 1:

The patent applies extraction by contacting the reaction mixture with a basic aqueous solution to selectively remove the harmful by-products (1-chloro-3,3-difluoro-1-propyne and oxide) from the HCFO-1233yd product. The basic solution extracts these impurities through chemical reaction, allowing the pure product to be separated and obtained.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the chemical environment by introducing a basic aqueous solution to alter the state of the by-products. The basic conditions cause the by-products to react and form water-soluble compounds, changing their solubility parameters and enabling their removal from the organic product phase.

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If 1-chloro-3,3-difluoro-1-propyne is contained in the composition at a high concentration, then the composition can be produced more easily, but reliability and performance deteriorate

Engineering Contradiction:
Improvecomposition productionVSAvoidcleaning agent, solvent, refrigerant, blowing agent, aerosol performance
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent removes 1-chloro-3,3-difluoro-1-propyne from the composition by contacting with basic aqueous solution. This extraction process selectively eliminates the harmful component while retaining the desired HCFO-1233yd product, thereby improving reliability without significantly complicating the manufacturing process.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent converts the harmful effect of 1-chloro-3,3-difluoro-1-propyne into a beneficial separation process. By using the chemical reactivity of the impurity with basic solutions, the patent transforms a manufacturing challenge into an efficient purification step that enhances product quality.

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

3Ease of manufacture

If oxide is contained in the composition at a high concentration, then the composition can be produced more easily, but stability deteriorates and acidifying agents form

Engineering Contradiction:
Improvecomposition productionVSAvoidcomposition stability
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The patent removes oxide from the composition through contact with basic aqueous solution. The oxide reacts with the basic solution to form water-soluble products that can be separated from the organic phase, effectively eliminating the stability-deteriorating impurity while maintaining ease of manufacture.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent converts the harmful oxide impurity into a removable substance by exploiting its reactivity with basic solutions. This transformation turns a stability problem into an efficient purification opportunity, where the impurity's chemical properties are used against it to enable easy removal.

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

4Device complexity

If conventional separation methods are used to separate HCFO-1233yd from by-products, then the production process is simple, but the removal efficiency of 1-chloro-3,3-difluoro-1-propyne and oxide is insufficient

Engineering Contradiction:
Improveseparation processVSAvoidby-product removal efficiency
Core Design Contradiction:
Device complexityVSManufacturing precision

Solution Approach 1:

The patent changes the chemical parameters of the system by introducing a basic aqueous solution. This parameter change fundamentally alters the solubility and reactivity characteristics of the by-products, enabling highly efficient removal through simple contact and separation operations without complex equipment.

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 method efficiently removes 1-chloro-3,3-difluoro-1-propyne and oxide from the composition, resulting in a highly pure HCFO-1233yd with improved stability and performance characteristics, suitable for various applications.

Implementation Method 1

contacting a composition comprising 1-chloro-2,3,3-trifluoropropene and at least one member selected from 1-chloro-3,3-difluoro-1-propyne and an oxide, with a basic aqueous solution, to remove said at least one member selected from 1-chloro-3,3-difluoro-1-propyne and an oxide

Methodology Applied
Scientific EffectDissolution: Solvation

Data Source

PatentUS10654778B2Method for producing 1-chloro-2,3,3-trifluoropropene
Publication Date: 2020.05.19 AGC INC
  • US10654778B2 patent drawing

AI summary

To provide a method for producing 1-chloro-2,3,3-trifluoropropene, whereby it is possible to efficiently remove 1-chloro-3,3-difluoro-1-propyne and/or an oxide from a composition comprising 1-chloro-2,3,3-trifluoropropene. A method for producing 1-chloro-2,3,3-trifluoropropene, in which a composition comprising 1-chloro-2,3,3-trifluoropropene and at least one member selected from 1-chloro-3,3-difluoro-1-propyne and an oxide, is brought into contact with a basic aqueous solution to remove said at least one member selected from 1-chloro-3,3-difluoro-1-propyne and an oxide, from the composition.