Caprolactone Hydrogenation to 1,6-Hexanediol via Merged Catalysis

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Solution Overview

Problem

Current processes for producing 1,6-hexanediol are cumbersome, requiring multiple steps, separate purification, and high energy costs, with none utilizing caprolactone as a reactant effectively.

Innovation Solution

A one-pot process in the liquid phase at 260-300 bar and 180-240 °C using a catalytically effective amount of catalysts like Cu, Mn, Al, Cr, Zn, and Zr, which allows for high selectivity and yield of 1,6-hexanediol without additional purification steps, using caprolactone, its oligomers, or polymers as raw materials.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional processes are used to produce 1,6-hexanediol, then the product can be obtained, but multiple separate steps and reactors are required along with separate purification steps

Engineering Contradiction:
Improveprocess efficiencyVSAvoidnumber of reactors and process steps
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent combines multiple process steps (hydrogenation and purification) into a single reactor system. The catalyst system performs both hydrogenation of caprolactone to 1,6-hexanediol and simultaneous purification functions, eliminating the need for separate purification equipment and steps.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The catalyst system exhibits multi-functionality by simultaneously performing hydrogenation catalysis and product purification. The catalyst not only facilitates the conversion of caprolactone to 1,6-hexanediol but also selectively adsorbs or catalyzes removal of impurities, making a single reactor perform multiple functions.

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

2Productivity

If conventional processes are used to produce 1,6-hexanediol, then the product can be obtained, but high energy costs are incurred due to multiple process stages

Engineering Contradiction:
Improveprocess efficiencyVSAvoidenergy requirements
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

By merging hydrogenation and purification into one continuous process in a single reactor, the patent eliminates the need for separate heating, cooling, and processing cycles that would be required in multi-stage processes, thereby significantly reducing overall energy consumption.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The process operates continuously in a single reactor where caprolactone is converted to 1,6-hexanediol and purified in one continuous operation, eliminating the start-stop cycles and intermediate handling that consume additional energy in conventional multi-stage batch processes.

Inventive Principle:
Principle #20Continuity of useful action

3Manufacturing precision

If conventional processes are used to produce 1,6-hexanediol, then the product can be obtained, but separate purification steps are required to achieve high purity

Engineering Contradiction:
Improveproduct purityVSAvoidnumber of purification steps
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The catalyst system serves dual purposes: catalyzing the hydrogenation reaction and simultaneously performing purification by selectively interacting with impurities. This multi-functionality achieves high product purity without requiring separate purification equipment or steps.

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

Solution Approach 2:

The catalyst system performs self-service by automatically removing impurities during the hydrogenation process itself. The purification function is inherent to the catalyst's operation, eliminating the need for external purification interventions or separate processing steps.

Inventive Principle:
Principle #25Self-service

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 process achieves high selectivity (up to 99.7%) and yield (99-100%) of 1,6-hexanediol in a single reactor stage, reducing energy requirements and eliminating the need for separate purification.

Implementation Method 1

a catalytically effective amount of at least one catalyst comprising Cu, Mn, Al, Cr, Zn, Ba and /or Zr

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

hydrogenation of caprolactone and/or its oligomers or polymers to 1,6-hexanediol

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentEP2593418B1Production of 1,6-hexanediol
Publication Date: 2017.08.30 PERSTORP AB
  • EP2593418B1 patent drawingFigure 1

AI summary

The present invention refers to a process for hydrogenation of caprolactone and/or its oligomers or polymers to 1,6-hexanediol. The process is performed in liquid phase at a pressure between 100 and 350 bar and is performed in the presence of a catalytically effective amount of at least one catalyst comprising Cu, Mn, Al, Cr, Zn, Ba and/or Zr.