Etheramine Synthesis via Catalyst-Controlled Amine Specificity

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Solution Overview

Problem

Current etheramine compounds used in various applications such as corrosion inhibition and metalworking additives lack specificity and efficiency in forming desired amine structures, leading to suboptimal performance in certain applications.

Innovation Solution

Development of a novel etheramine compound with specific structures formed by reacting 4-methylcyclohexane methanol or 4-methoxymethylcyclohexane methanol with an alkene having a nitrile group, followed by hydrogenation, using different catalysts to control the formation of primary, secondary, or tertiary amines, which are then used in corrosion inhibition, metalworking, and other applications.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional etheramine compounds are used, then they can be applied in various applications such as corrosion inhibition and metalworking additives, but they lack specificity and efficiency in forming desired amine structures

Engineering Contradiction:
Improvespecificity in forming desired amine structuresVSAvoidefficiency in forming desired amine structures
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent applies parameter changes by systematically varying reaction conditions including temperature ranges (20-100°C), pressure conditions (1-100 atm), and catalyst types (metal catalysts, organic catalysts, enzymatic catalysts) to control the formation of specific amine structures. This enables precise control over primary, secondary, and tertiary amine content while maintaining high reaction efficiency

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent implements local quality by creating etheramine compounds with specific structural characteristics at different positions in the molecule. By controlling the degree of ethoxylation and the specific arrangement of amine groups, the patent achieves localized functional properties that enhance both specificity and efficiency in target applications

Inventive Principle:
Principle #3Local quality

2Reliability

If specific amine structures are formed to improve functional properties, then performance in corrosion inhibition and metalworking applications is enhanced, but the manufacturing process becomes more complex

Engineering Contradiction:
Improveperformance in corrosion inhibition and metalworking applicationsVSAvoidcomplexity of manufacturing process
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies preliminary action by pre-selecting and pre-mixing catalyst systems before the main reaction. The catalysts are prepared and characterized in advance, and reaction conditions are pre-optimized to enable direct formation of desired amine structures without requiring complex post-processing or additional purification steps

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent implements universality by developing a versatile catalytic system that can produce primary, secondary, and tertiary amines using the same general reaction framework. The method can accommodate different catalyst types and reaction conditions to achieve various amine structures, simplifying the manufacturing process while maintaining high reliability across different product specifications

Inventive Principle:
Principle #6Universality (Multi-functionality)

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 novel etheramine compounds demonstrate enhanced performance as corrosion inhibitors, metalworking additives, and in other applications by achieving specific amine structures that improve their functional properties, such as increased primary, secondary, or tertiary amine content, depending on the catalyst used, leading to improved efficacy in these uses.

Implementation Method 1

hydrogenating the intermediate compound to form the etheramine compound

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 2

using different catalysts to control the formation of primary, secondary, or tertiary amines

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS10472318B2Etheramine compounds
Publication Date: 2019.11.12 HUNTSMAN PETROCHEMICAL LLC
  • US10472318B2 patent drawing
  • US10472318B2 patent drawing
  • US10472318B2 patent drawing

AI summary

Embodiments described herein provide a compound that may be used in a variety of applications such as corrosion inhibition, additives for metalworking, mining reagents, epoxy curatives, emulsifiers, fuel or lubricant additives, surfactant manufacture, acid scavengers and asphalt additives. The compound has the following structure:where R1 is a methoxy group,R2, R3, R4 and R5 are independently a hydrogen atom or an alkyl group, andR6 is an aminomethyl group.