Tertiary Alkyl Amine Synthesis via Cyanide Recycling

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Solution Overview

Problem

Existing methods for producing tertiary alkyl primary amines generate cyanide waste products, which require expensive treatment for disposal, and lack efficient recycling of hydrogen cyanide.

Innovation Solution

A method involving the steps of contacting hydrogen cyanide, an acid, and a substrate capable of generating a carbonium ion, followed by hydrogen cyanide removal to low ppm levels using a stripper column, and recycling it, with subsequent neutralization using alkali metal hydroxide to produce the amine, minimizing cyanide waste.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If existing methods for producing tertiary alkyl primary amines are used, then the amine production is achieved, but cyanide waste products are generated requiring expensive treatment for disposal

Engineering Contradiction:
Improveamine productionVSAvoidcyanide waste
Core Design Contradiction:
Ease of manufactureVSObject-generated harmful factors

Solution Approach 1:

The patent implements a recycling system where hydrogen cyanide is removed from the reaction mixture via a stripper column and recovered for reuse in the carbonylation reactor. This eliminates the need to discard cyanide as waste and prevents the formation of cyanide-containing waste products, directly resolving the contradiction between ease of manufacture and harmful waste generation

Inventive Principle:
Principle #34Discarding and recovering

Solution Approach 2:

The patent establishes a feedback loop where the stripper column continuously monitors and removes hydrogen cyanide from the reaction mixture, and the recovered cyanide is fed back to the carbonylation reactor. This closed-loop system ensures cyanide is maintained at optimal levels for production while preventing waste accumulation, resolving the contradiction between manufacturing efficiency and waste reduction

Inventive Principle:
Principle #23Feedback

2Device complexity

If hydrogen cyanide is not recycled, then the process is simpler, but cyanide waste accumulates requiring expensive treatment

Engineering Contradiction:
Improveprocess simplicityVSAvoidhydrogen cyanide
Core Design Contradiction:
Device complexityVSLoss of substance

Solution Approach 1:

The patent implements a recycling system where hydrogen cyanide is removed from the reaction mixture via a stripper column and recovered for reuse in the carbonylation reactor. This eliminates the need to discard cyanide as waste and prevents the formation of cyanide-containing waste products, directly resolving the contradiction between ease of manufacture and harmful waste generation

Inventive Principle:
Principle #34Discarding and recovering

Solution Approach 2:

The patent establishes continuous operation where hydrogen cyanide is constantly stripped from the reaction mixture and continuously recycled back to the carbonylation reactor. This continuous recycling prevents substance loss and eliminates waste treatment requirements, resolving the contradiction between process simplicity and substance conservation

Inventive Principle:
Principle #20Continuity of useful action

3Object-affected harmful factors

If cyanide waste is treated for disposal, then environmental compliance is achieved, but production costs increase

Engineering Contradiction:
Improveenvironmental complianceVSAvoidproduction cost
Core Design Contradiction:
Object-affected harmful factorsVSLoss of energy

Solution Approach 1:

The patent converts the potentially harmful cyanide waste product into a beneficial recycled reactant. By stripping hydrogen cyanide from the reaction mixture and recycling it to the carbonylation reactor, the system transforms waste into a valuable resource, eliminating disposal costs and converting an environmental liability into an economic benefit, thus resolving the contradiction between environmental compliance and production cost

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

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

Significantly reduces cyanide waste and allows for its recycling, thereby lowering production costs and environmental impact while maintaining high efficiency in amine production.

Implementation Method 1

hydrogen cyanide is removed from the second reaction intermediate by a stripper column

Methodology Applied
Scientific EffectEvaporation: Evaporation

Implementation Method 2

contacting hydrogen cyanide or a salt thereof, an acid, water and a substrate compound capable of generating a carbonium ion by reaction with the acid

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 3

contacting the second reaction intermediate with an alkali metal hydroxide to form the amine

Methodology Applied
Scientific EffectNeutralization reaction: Chemical Bonding

Data Source

PatentEP2953924B1Process for preparation of tertiary alkyl primary amines
Publication Date: 2017.10.25 DOW GLOBAL TECHNOLOGIES LLC
  • EP2953924B1 patent drawing
  • EP2953924B1 patent drawing

AI summary

A method for producing an amine. The first step is contacting a cyanide, an acid, water and a substrate compound capable of generating a carbonium ion by reaction with the acid to generate a first reaction intermediate. The second step is contacting the first reaction intermediate with water to form a second reaction intermediate. The third step is removing cyanide present in the second reaction intermediate to a concentration less than 10 ppm. The fourth step is contacting the second reaction intermediate with an alkali metal hydroxide to form the amine