Tertiary Alkoxide Base Reduces Viscosity in Triazine Carbamate Synthesis

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Solution Overview

Problem

The existing processes for preparing triazine carbamates often result in excessively high viscosity during reactions, leading to increased energy consumption and the need for specialized equipment or diluted reaction mixtures, which reduces space-time yield and complicates handling and neutralization.

Innovation Solution

The use of a base with a tertiary alkoxide of alkali or earth alkali metals in combination with specific monohydric alcohol solvents, such as tert-butyl or tert-pentyl alcohols, significantly reduces viscosity, allowing for higher reactant concentrations and efficient mixing, thereby improving space-time yield and handling of the reaction mixture.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of operation

If conventional bases (alkali metal hydrides, alkoxides, hydroxides) are used in the reaction, then the reaction can proceed, but the viscosity of the reaction mixture becomes excessively high

Engineering Contradiction:
Improveviscosity of reaction mixtureVSAvoidspace-time yield
Core Design Contradiction:
Ease of operationVSProductivity

Solution Approach 1:

The patent changes the chemical composition parameter by introducing a specific base mixture comprising an alkali metal or earth alkali metal alkoxide combined with a quaternary ammonium or phosphonium alkoxide in a weight ratio of 1:4 to 1:10. This parameter change fundamentally alters the reaction mixture's viscosity characteristics, enabling high concentration reactions without excessive viscosity buildup.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs a composite base system combining two types of alkoxides with different chemical properties - a metal alkoxide (alkali or earth alkali) and a quaternary ammonium or phosphonium alkoxide. This composite base mixture synergistically reduces viscosity while maintaining reaction effectiveness, allowing higher reactant concentrations and improved space-time yield.

Inventive Principle:
Principle #40Composite materials

2Ease of operation

If the reaction mixture is diluted to reduce viscosity, then handling becomes easier, but the space-time yield decreases

Engineering Contradiction:
Improvehandling of reaction mixtureVSAvoidspace-time yield
Core Design Contradiction:
Ease of operationVSProductivity

Solution Approach 1:

The patent changes the concentration parameter by enabling reactions at high reactant concentrations (without dilution) while maintaining acceptable viscosity through the specialized base mixture. This parameter change simultaneously improves productivity (higher space-time yield) and maintains ease of operation (acceptable handling).

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent converts the typically harmful effect of high concentration (which would increase viscosity) into a benefit by using the specialized base mixture that prevents viscosity buildup. This allows the process to operate at high concentrations for improved productivity while maintaining ease of handling.

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

3Ease of operation

If special equipment such as thin film reactors or kneaders is used to handle high viscosity, then the reaction can proceed, but device complexity increases

Engineering Contradiction:
Improvehandling of reaction mixtureVSAvoidreactor equipment
Core Design Contradiction:
Ease of operationVSDevice complexity

Solution Approach 1:

The patent changes the viscosity parameter of the reaction mixture through the specialized base mixture, enabling the use of conventional reactor equipment. This parameter change eliminates the need for complex specialized equipment while maintaining ease of operation.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces expensive, complex specialized equipment (thin film reactors, kneaders) with conventional, simpler reactor designs. This substitution reduces device complexity and capital investment while achieving the same handling effectiveness through the improved chemical composition.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

4Productivity

If higher reactant concentrations are used to increase productivity, then space-time yield improves, but viscosity increases making handling difficult

Engineering Contradiction:
Improvespace-time yieldVSAvoidviscosity of reaction mixture
Core Design Contradiction:
ProductivityVSEase of operation

Solution Approach 1:

The patent changes the chemical composition parameter by introducing the specialized base mixture, which decouples the relationship between concentration and viscosity. This enables higher reactant concentrations for improved productivity without the usual penalty of excessive viscosity.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses a composite base mixture that synergistically manages viscosity at high concentrations. The combination of metal alkoxide and quaternary ammonium/phosphonium alkoxide creates a system that maintains flowability even at high reactant concentrations, enabling improved productivity without handling difficulties.

Inventive Principle:
Principle #40Composite materials

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 allows for higher reaction product concentrations, efficient neutralization, and the use of conventional reactor designs, enhancing the process's efficiency and productivity while maintaining low viscosity, thus overcoming the limitations of previous methods.

Implementation Method 1

a base B which is an alkoxide M(OR1) which is selected from the group consisting of alkali metals (a = 1) and earth alkali metals (a = 2), or mixtures thereof with a further alkoxide M(OR0)

Methodology Applied
Scientific EffectSolvation: Solvation

Data Source

PatentEP3191460B1Process for the preparation of triazine carbamates
Publication Date: 2020.01.29 ALLNEX NETHERLANDS BV
  • EP3191460B1 patent drawing

AI summary

This invention relates to a process for the preparation of triazine carbamates by reacting a mixture of an aminotriazine A having at least two amino groups per molecule, an organic carbonate C, and a base B selected from the group consisting of alkoxides, and arylalkoxides of metals M, which may be alkali or earth alkali metals, and a solvent S which is a monohydric alcohol solvent R2OH or a mixture of solvents that comprises a monohydric alcohol R2OH, and a monohydric alcohol R3OH, or a mixture of solvents that comprises a monohydric alcohol R2OH with a further solvent selected from the group consisting of ether, alcohol, and hydrocarbon solvents, and adding to the products of the said reaction, an acid or a solution of an acid in a solvent.