Integrated Beta-Lactone Process for Nitrile Production

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Solution Overview

Problem

There is a need for integrated methods and systems in the industrial production of nitriles and nitrile precursors that utilize inexpensive and renewable feedstocks, consolidate multiple synthetic operations, and avoid costly purification of intermediates, while operating under mild reaction conditions.

Innovation Solution

The method involves combining a hydroxypropanamide stream with a dehydration agent in the presence of a solvent and ammonia to produce unsaturated amide and/or nitrile products. This process includes carbonylating an epoxide with carbon monoxide to produce a beta lactone, which is then reacted with ammonia to form hydroxypropanamide, and subsequently dehydrated to yield the desired nitrile or amide products.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If catalytic ammoxidation of propylene is used to produce acrylonitrile, then nitrile products can be obtained, but harsh reaction conditions and costly reagents are required

Engineering Contradiction:
Improvenitrile production efficiencyVSAvoidreaction condition severity
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent changes the reaction parameters by using beta-lactone as a milder alternative feedstock compared to propylene ammoxidation, enabling nitrile production under less severe conditions while maintaining productivity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs inexpensive renewable feedstocks such as beta-lactone derived from biological sources, replacing costly conventional reagents and achieving cost-effective nitrile production

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

2Manufacturing precision

If multiple synthetic operations are performed separately, then each reaction can be optimized, but costly purification of intermediates is required

Engineering Contradiction:
Improvereaction optimizationVSAvoidpurification process complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent merges multiple synthetic operations into an integrated one-pot process where beta-lactone ring-opening, amide formation, and nitrile dehydration occur sequentially in a single reactor, eliminating intermediate purification steps while maintaining reaction optimization

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent implements continuous sequential reactions where the product of one step serves as the substrate for the next step without interruption or isolation, maintaining continuous useful action throughout the synthesis pathway

Inventive Principle:
Principle #20Continuity of useful action

3Productivity

If conventional feedstocks are used, then industrial production can proceed, but expensive and non-renewable resources are consumed

Engineering Contradiction:
Improveindustrial production capacityVSAvoidrenewability of feedstocks
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent uses inexpensive renewable feedstocks including beta-lactone from biological sources and carbon monoxide, replacing expensive non-renewable petroleum-based feedstocks while maintaining industrial production capacity

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

Solution Approach 2:

The patent employs universal renewable feedstocks that can serve multiple purposes - beta-lactone serves as both a chemical intermediate and a renewable resource, enabling sustainable industrial production

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

This approach enables the efficient production of nitriles and nitrile precursors from renewable sources under mild conditions, reducing costs and environmental impact while improving process integration and product yield.

Implementation Method 1

The beta lactone may be prepared by contacting carbon monoxid with an epoxide in the presence of a carbonylation catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

combining a hydroxyprop amide stream comprising a hydroxypropanamide with a dehydration agent to produce a product stream comprising an unsaturated amide and/or an unsaturated nitrile

Methodology Applied
Scientific EffectDehydration:

Data Source

PatentEP3935041B1Integrated methods and systems for producing amide and nitrile compounds
Publication Date: 2025.04.09 NOVOMER INC
  • EP3935041B1 patent drawingFigure 1
  • EP3935041B1 patent drawingFigure 2
  • EP3935041B1 patent drawingFigure 3~4

AI summary

Provided herein are integrated methods and systems for the production of acrylamide and acrylonitrile compounds and other compounds from at least beta-lactones and/or beta-hydroxy amides.