5-(Halomethyl)furfural Conversion to Cyclohexanone and Nylon

Resolve Bottlenecks,
Find Innovative SolutionsGenerate Solutions

Solution Overview

Problem

Current methods lack efficient processes for producing a variety of compounds such as cyclohexanone, hexanediamine, hexanediol, hexamethylenediamine, caprolactam, and nylon from 5-(halomethyl)furfural, which are essential for producing bio-based fuels and chemicals, limiting the platform of compounds that can be derived from this renewable source.

Innovation Solution

A method involving the conversion of 5-(halomethyl)furfural through specific chemical reactions, including oxidation and cyclization, to produce these compounds, utilizing catalysts and salts to achieve the desired products, such as cyclohexanone, hexane-1,6-diol, hexamethylenediamine, and caprolactam, which can then be polymerized to form nylon.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If current methods are used for producing compounds from 5-(halomethyl)furfural, then the existing production processes are maintained, but the platform of compounds that can be produced is limited

Engineering Contradiction:

Improveplatform of compounds that can be producedVSAvoidefficiency of production processes

Core Design Contradiction:

Adaptability or versatilityVSEase of manufacture

Solution Approach 1:

The patent segments the production process into distinct reaction pathways from 5-(halomethyl)furfural, dividing the synthesis of different compounds (cyclohexanone, hexanediamine, hexanediol, hexamethylenediamine, caprolactam, and nylon) into separate manageable routes. Each pathway uses specific catalysts and reaction conditions optimized for that particular product, allowing independent optimization and selection based on desired output.

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

The patent establishes 5-(halomethyl)furfural as a universal platform chemical that can serve multiple functions and lead to various valuable products. By demonstrating that a single starting material can be converted into six different important compounds through different reaction pathways, the invention multiplies the utility and versatility of this renewable feedstock.

Inventive Principle:

Principle #6Universality (Multi-functionality)

2Productivity

If existing production methods are used, then current process complexity is maintained, but productivity and output efficiency are limited

Engineering Contradiction:

Improveoutput efficiency of compound productionVSAvoidprocess complexity

Core Design Contradiction:

ProductivityVSDevice complexity

Solution Approach 1:

The patent performs preliminary conversion of 5-(halomethyl)furfural into key intermediate compounds that can then be further transformed into multiple final products. By establishing these intermediate stages with appropriate catalysts and conditions, the process prepares the material in advance for various downstream applications, improving overall productivity through staged production.

Inventive Principle:

Principle #10Preliminary action

Solution Approach 2:

The patent utilizes parameter changes including different catalysts (metal catalysts, organic catalysts, enzyme catalysts), varying reaction conditions (temperature, pressure, solvent systems), and different stoichiometric ratios to optimize each production pathway. These parameter adjustments enable high productivity for each specific compound while managing process complexity through systematic optimization.

Inventive Principle:

Principle #35Parameter changes

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 method enables the production of a range of valuable chemicals and polymers from 5-(halomethyl)furfural, expanding its utility in bio-based industries by providing efficient routes to cyclohexanone, hexanediamine, hexanediol, hexamethylenediamine, caprolactam, and nylon, thereby enhancing the use of renewable biomass sources.

Implementation Method 1

converting 5-(halomethyl)furfural to hexane-1,5-diol

Methodology Applied

Scientific EffectHydrogenation: Hydrogenation

Implementation Method 2

oxidizing the hexane-1,5-diol to produce 6-hydroxyhexan-2-one

Methodology Applied

Scientific EffectOxidation: Oxidation

Implementation Method 3

cyclizing the 6-hydroxyhexan-2-one to produce cyclohexanone

Methodology Applied

Scientific EffectCyclization:

Implementation Method 4

reducing the 5-(alkoxymethyl)furan-2-carbaldehyde to produce hexane-1,6-diol

Methodology Applied

Scientific EffectReduction: Reduction

Implementation Method 5

polymerizing the 5-(aminomethyl)furan-2-carboxylic acid to form a polymer

Methodology Applied

Scientific EffectPolymerization:

Data Source

PatentUS10407547B2Methods of producing compounds from 5-(halomethyl)furfural

Publication Date: 2019.09.10 ORIGIN MATERIALS OPERATING INC

AI summary

Provided herein are methods of producing compounds, such as cyclohexanone, hexanediamine, hexanediol, hexamethylenediamine, caprolactam and nylon, from 5-(halomethyl)furfural.