Bio-Based Surfactants via Hydrogenated Diels-Alder Adducts
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Solution Overview
Problem
Current bio-based surfactants, such as oleo-furan surfactants derived from furan and fatty acids, face inefficiencies in atom economy and increased costs due to decarbonylation processes, and require additional processing steps, while petrochemical-based LAS surfactants have a negative environmental impact.
Innovation Solution
Development of hydrogenated Diels-Alder adducts as surfactants, which are synthesized using bio-based furfural, offering improved atom efficiency and reduced processing steps, and can function as chelating agents, reducing the need for additional additives in formulations.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If decarbonylation of furfural is used to produce surfactants, then surfactant properties are achieved, but atom efficiency decreases and carbon monoxide waste is generated
Solution Approach 1:
The invention extracts and eliminates the decarbonylation step from the synthesis pathway. By using direct hydrogenation of furfural instead of decarbonylation followed by furan synthesis, the harmful CO removal step is taken out of the process, improving atom efficiency while maintaining surfactant production
Solution Approach 2:
The conventional approach of decarbonylation then furan formation is inverted. The invention directly hydrogenates furfural to the desired surfactant structure, reversing the traditional sequence and avoiding the intermediate furan formation that necessitates CO elimination
2Reliability
If decarbonylation of furfural is used to produce surfactants, then surfactant properties are achieved, but additional processing steps are required increasing cost and inefficiency
Solution Approach 1:
The invention merges the decarbonylation and furan formation steps into a single direct hydrogenation step. By combining what were previously separate processing stages into one operation, the total number of processing steps is reduced, improving productivity and reducing costs
Solution Approach 2:
The invention performs the hydrogenation action preliminarily and directly on furfural, avoiding the need for intermediate furan formation. This preliminary direct conversion eliminates subsequent processing requirements, streamlining the overall synthesis pathway
3Reliability
If petrochemical-based LAS surfactants are used, then good surfactant performance is achieved, but negative environmental impact occurs
Solution Approach 1:
The invention changes the fundamental parameter of feedstock origin from petrochemical to bio-based. By substituting renewable furfural-derived materials for fossil-based LAS precursors, the environmental impact parameter is improved while maintaining surfactant performance through careful molecular design
Solution Approach 2:
The invention creates composite surfactant molecules combining the hydrophobic tail from bio-based sources with appropriate hydrophilic head groups. This composite approach allows achievement of LAS-like performance using sustainable bio-based materials
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
The hydrogenated Diels-Alder adducts provide stable, efficient, and cost-effective surfactant properties comparable to LAS, with enhanced biodegradability and tolerance to hard water, addressing environmental concerns and production inefficiencies of previous bio-based surfactants.
Implementation Method 1
hydrogenated Diels-Alder adducts
Implementation Method 2
hydrogenated Diels-Alder adducts
Data Source
AI summary
The invention is directed to a hydrogenated Diels-Alder adduct according to formula (I) or a salt thereof wherein X is H or an aliphatic moiety that is optionally substituted with one or more heteroatom-comprising substitutents such as hydroxyl, preferably CH2OH or H, more preferably H; R3 is an aliphatic chain comprising at least 6 consecutive carbon atoms: Q1 and Q2 together or individually comprise one or more carboxylic acid moieties, sulfonic acid moieties, salts thereof and/or combinations thereof. In a further aspect, the invention is directed to intermediate compounds and methods to prepare the hydrogenated Diels-Alder adduct.