Bio-renewable Polythiol Compounds from Amino Acids
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Solution Overview
Problem
The chemical industry's reliance on petroleum-based carbon feedstocks is unsustainable, and there is a need for bio-renewable thiol functional compounds for use in click reactions, which are currently derived from petrochemical sources.
Innovation Solution
Development of polythiol compounds derived from amino acids like serine and tyrosine, synthesized through processes involving allylation, thiol-ene reactions, and deprotection steps, which can be used as reactive components in curable compositions.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If thiol-containing compounds are derived from petrochemical sources, then the production cost is low and the supply is stable, but the sustainability is poor and environmental impact is high
Solution Approach 1:
The invention changes the source parameter of thiol-containing compounds from petrochemical to biomass-derived, transforming the sustainability characteristic while maintaining the functional properties required for click reactions. This parameter change enables the use of renewable resources without compromising the chemical reactivity needed for thiol-ene and thiol-epoxy polymerizations.
Solution Approach 2:
The patent utilizes biomass as a renewable, short-lived feedstock that can be continuously replenished, replacing depleting petrochemical resources. By deriving thiol-containing compounds from biomass through chemical modification of natural products, the invention creates a sustainable alternative that maintains economic viability while reducing environmental harm.
2Object-affected harmful factors
If biomass is used as feedstock for chemical products, then the sustainability is improved and environmental impact is reduced, but the processing efficiency may decrease and production cost may increase
Solution Approach 1:
The invention performs preliminary chemical modification of biomass-derived natural products to introduce thiol-containing functional groups and reactive moieties. By pre-functionalizing biomass components through steps such as allylation, thiol-ene reactions, and deprotection, the patent creates intermediates that can be efficiently converted to final thiol-containing compounds, thereby improving overall processing efficiency.
Solution Approach 2:
The patent employs intermediary compounds derived from biomass that serve as bridging structures between renewable feedstock and target thiol-containing products. These intermediates, obtained through controlled chemical transformations of natural products, facilitate efficient conversion pathways while maintaining sustainability benefits throughout the synthesis route.
3Reliability
If traditional petrochemical-based thiol compounds are used, then the material performance is reliable and consistent, but the long-term availability is compromised due to finite resources
Solution Approach 1:
The invention demonstrates that biomass-derived thiol-containing compounds can fulfill multiple functions: they serve as sustainable feedstock alternatives, maintain the chemical reactivity required for click chemistry applications, and provide a renewable basis for thiol-ene and thiol-epoxy polymerizations. This multi-functionality ensures both material performance reliability and long-term availability through renewable sourcing.
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 use of bio-renewable polythiol compounds enables the creation of sustainable chemical products with high biocarbon content, reducing environmental impact and providing efficient processing methods for biomass-based materials.
Implementation Method 1
reacting, in the presence of at least one base, said compound of general Formula IA, IB or IC with a primary allyl compound (II) having the general formula: X—(R1)—C(R2)═CH2 (II) to form, respectively, a compound of Formula IIIA, IIIB or IIIC
Implementation Method 2
reacting said compound of Formula IIIA, IIIB or IIIC with a thiol acid (IV) having the general formula R3—C(═O)—SH (IV) to form, respectively, a thioester compound of Formula VA, VB or VC
Implementation Method 3
deprotecting said thioester compound of Formula VA, VB or VC to form, respectively, said polythiol compound of Formula VIA, VIB or VIC
Data Source
AI summary
The present application is directed to a polythiol compound obtainable from at least one of serine (Ser) and tyrosine (Tyr) and having the general Formula VIA, VIB or VIC, wherein: R1 is a C1-C18 alkylene group, C2-C18 oxyalkylene group, C2-C18 thioalkylene group, C6-C18 arylene or C7-C18 aralkylene group; and, R2 is H or methyl.