1,6-Hexanediol Production from Carbohydrate-Derived Furfural
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Solution Overview
Problem
Current methods for producing hexamethylenediamine (HMDA) from crude oil are inefficient and costly due to the shift towards lighter feeds, which reduce butadiene production, and there is a lack of commercially viable processes using biorenewable resources, particularly from carbohydrate-containing materials like glucose.
Innovation Solution
A process converting 1,2,6-hexanetriol to 1,6-hexanediol using a hydrogenation catalyst comprising Pt, with optional support materials like zirconias, silicas, and zeolites, and further converting 1,6-hexanediol to hexamethylenediamine, utilizing a furfural substrate derived from carbohydrates, achieving yields of at least 40%, 50%, or 60%.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If conventional oil-based processes are used to produce HMDA, then current production capability is maintained, but production costs increase and efficiency decreases due to the shift towards lighter feeds reducing butadiene availability
Solution Approach 1:
The invention changes the fundamental parameter of feedstock source from petroleum-derived butadiene to biorenewable carbohydrate materials. This parameter change bypasses the butadiene supply constraint caused by lighter feedstock cracking and establishes a new production pathway that is not subject to the same supply chain vulnerabilities and cost volatility
Solution Approach 2:
The invention introduces furfural as an intermediary compound in the production pathway. Carbohydrate materials are converted to furfural, which then serves as the substrate for hydrogenation to produce 1,6-hexanediol and subsequently HMDA. This intermediary enables the transition from renewable feedstock to the target chemical while avoiding direct dependence on butadiene
2Adaptability or versatility
If biorenewable carbohydrate materials are used as feedstock, then sustainability is improved and petroleum dependence is reduced, but no commercially viable process currently exists
Solution Approach 1:
The invention segments the conversion process into distinct catalytic stages: (1) carbohydrate to furfural conversion, (2) furfural hydrogenation to 1,6-hexanediol using Pt-based catalysts, and (3) 1,6-hexanediol conversion to HMDA. This segmentation allows each stage to be optimized independently with appropriate catalysts and conditions, enabling commercial viability while maintaining sustainability
Solution Approach 2:
The invention employs composite catalytic systems, particularly Pt-based catalysts supported on appropriate materials, to achieve the hydrogenation of furfural. The composite nature of these catalysts provides both the activity needed for efficient conversion and the stability required for commercial operation, bridging the gap between laboratory feasibility and industrial viability
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 provides a more efficient and commercially viable method for producing 1,6-hexanediol and hexamethylenediamine from biorenewable sources, improving yield and reducing dependence on petroleum-derived feedstocks, thus enhancing industrial scalability and competitiveness.
Implementation Method 1
converting at least 1,2,6-hexanetriol to 1,6-hexanediol in the presence of hydrogen and a hydrogenation catalyst comprising Pt
Implementation Method 2
converting at least a portion of the 1,6-hexanediol to hexamethylenediamine
Data Source
AI summary
Processes are disclosed for the conversion of a carbohydrate source to hexamethylenediamine (HMDA) and to intermediates useful for the production of hexamethylenediamine and other industrial chemicals. HMDA is produced by direct reduction of a furfural substrate to 1,6-hexanediol in the presence of hydrogen and a heterogeneous reduction catalyst comprising Pt or by indirect reduction of a furfural substrate to 1,6-hexanediol wherein 1,2,6-hexanetriol is produced by reduction of the furfural substrate in the presence of hydrogen and a catalyst comprising Pt and 1,2,6-hexanediol is then converted by hydro genation in the presence of a catalyst comprising Pt to 1,6 hexanediol, each process then proceding to the production of HMDA by known routes, such as amination of the 1,6 hexanediol. Catalysts useful for the direct and indirect production of 1,6- hexanediol are also disclosed.