Cyanogen Halide Production via Excess Cyanide

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Solution Overview

Problem

Current methods for producing cyanate ester compounds face challenges in achieving high-purity and high-yield production due to issues with unreacted halogen and cyanide residues, leading to side reactions and insufficient thermal and flame retardant properties in the final products.

Innovation Solution

A method involving the controlled reaction of hydrogen cyanide or metal cyanide with a halogen molecule, where the molar ratio is optimized to suppress side reactions, and the reaction is terminated within a specific pH and temperature range to produce a cyanogen halide, which is then used to react with a hydroxy-substituted aromatic compound in the presence of a basic compound to form a cyanate ester compound.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If the reaction is terminated to prevent unreacted hydrogen cyanide or chlorine from remaining, then safety is improved, but it is extremely difficult to control the reaction such that neither unreacted hydrogen cyanide nor unreacted chlorine remains

Engineering Contradiction:
ImprovesafetyVSAvoidreaction control precision
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The invention changes the reaction parameters by using an aqueous solution system with controlled pH and temperature, and by using a specific molar ratio of metal cyanide to halogen (1:1.05 to 1:1.2), thereby achieving both safety and reaction control precision simultaneously

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces water as an intermediary solvent and uses the aqueous solution environment to mediate the reaction between metal cyanide and halogen, which helps control the reaction progress and prevent excessive accumulation of unreacted hazardous substances

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If metal cyanide is used in equimolar ratio or less than halogen to produce cyanogen halide, then the composition of cyanogen halide-containing solution can be controlled, but unreacted halogen remains in the reaction system leading to side reactions

Engineering Contradiction:
Improvecomposition controlVSAvoidside reactions from unreacted halogen
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The invention uses a slight excess of metal cyanide (molar ratio 1:1.05 to 1:1.2 relative to halogen) to ensure complete consumption of halogen and prevent unreacted halogen from causing side reactions, while maintaining good composition control

Inventive Principle:
Principle #16Partial or excessive action

3Object-generated harmful factors

If hydrogen cyanide or metal cyanide is used in excessive amount to ensure complete reaction of halogen, then unreacted halogen is minimized, but a large amount of unreacted hydrogen cyanide or metal cyanide remains in the reaction system

Engineering Contradiction:
Improveunreacted halogen minimizationVSAvoidunreacted metal cyanide
Core Design Contradiction:
Object-generated harmful factorsVSLoss of substance

Solution Approach 1:

The invention optimizes the molar ratio parameter to a specific range (1:1.05 to 1:1.2) and controls reaction conditions (aqueous solution, pH, temperature) to achieve the minimum excess of metal cyanide needed for complete halogen consumption, thereby minimizing waste

Inventive Principle:
Principle #35Parameter changes

4Productivity

If conventional methods are used to produce cyanate ester compound, then production can proceed, but high-purity and high-yield production is difficult to achieve due to unreacted halogen and cyanide residues

Engineering Contradiction:
Improveproduction efficiencyVSAvoidproduct purity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The invention performs preliminary action by completely consuming halogen through optimized molar ratio and reaction conditions before the cyanate ester compound formation step, thereby preventing side reactions and ensuring high purity and high yield in the final product

Inventive Principle:
Principle #10Preliminary 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 approach enables the efficient production of high-purity cyanate ester compounds with improved thermal expansion, flame retardance, and moisture resistance, suitable for advanced polymer materials.

Implementation Method 1

contacting a halogen molecule with an aqueous solution containing hydrogen cyanide and/or a metal cyanide, so that the hydrogen cyanide and/or the metal cyanide is allowed to react with the halogen molecule in a reaction solution to obtain the cyanogen halide

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

reacting the cyanogen halide with a hydroxy-substituted aromatic compound in the presence of a basic compound to form a cyanate ester compound

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentEP2913302B1Cyanogen-halide production method, cyanate ester compound and production method therefor, and resin composition
Publication Date: 2019.04.10 MITSUBISHI GAS CHEM CO INC
  • EP2913302B1 patent drawingFigure 1
  • EP2913302B1 patent drawingFigure 2
  • EP2913302B1 patent drawingFigure 3

AI summary

Upon production of a cyanate ester compound, it is an object of the present invention to provide a method for efficiently producing a cyanogen halide with suppressed side effects, and a method for producing a high-purity cyanate ester compound at a high yield. A method for producing the cyanogen halide, which includes a cyanogen halide-producing step of contacting a halogen molecule with an aqueous solution containing hydrogen cyanide and/or a metal cyanide, so that the hydrogen cyanide and/or the metal cyanide is allowed to react with the halogen molecule in the reaction solution to obtain the cyanogen halide, wherein, in the cyanogen halide-producing step, more than 1 mole of the hydrogen cyanide or the metal cyanide is used based on 1 mole of the halogen molecule, and when an amount of substance of an unreacted hydrogen cyanide or an unreacted metal cyanide is defined as mole (A) and an amount of substance of the generated cyanogen halide is defined as mole (B), the reaction is terminated in a state in which (A) : (A) + (B) is between 0.00009 : 1 and 0.2 : 1.