Bio-renewable Polythiol Synthesis via Trans-β-farnesene Intermediates
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
The chemical industry relies on non-sustainable petroleum-based carbon feedstocks, and there is a need for efficient production of 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 bio-renewable resources, specifically through the reaction of a compound with a primary allyl compound and a thiol acid or thiolate ester, followed by deprotection, to create a polythiol compound suitable for use in curable compositions.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If thiol-containing compounds are derived from petrochemical sources, then the production process is well-established and efficient, but the feedstock is non-sustainable as it consumes resources that required millions of years to form
Solution Approach 1:
The patent changes the source parameter of the feedstock from petrochemical to bio-renewable resources, specifically using polymeric derivatives of trans-β-farnesene obtained from natural sources. This parameter change maintains the chemical functionality required for thiol-ene and thiol-epoxy reactions while achieving sustainability goals.
Solution Approach 2:
The patent uses polymeric intermediates derived from bio-renewable trans-β-farnesene as mediators to bridge between sustainable feedstock and the required thiol functional groups. These intermediates serve as the connecting link that enables sustainable production of click reaction compounds.
2Stability of the object's composition
If biomass is used as feedstock to achieve sustainability, then the feedstock formation timescale matches utilization timescale, but significant cost disruption may occur without efficient processing methods
Solution Approach 1:
The patent performs preliminary processing of biomass-derived trans-β-farnesene to create polymeric intermediates with specific functional groups before the final thiol conversion. This preliminary action prepares the biomass in a form that facilitates efficient and cost-effective production of thiol-containing compounds.
Solution Approach 2:
The patent segments the complex biomass processing into distinct stages: first obtaining trans-β-farnesene from natural sources, then converting it to polymeric intermediates, and finally producing thiol-containing compounds. This segmentation makes the overall process more manageable and efficient.
3Ease of manufacture
If traditional petrochemical sources are used for thiol-containing, ene-containing and epoxide compounds, then the production is cost-effective, but the chemical industry becomes reliant on non-renewable resources
Solution Approach 1:
The patent creates polymeric intermediates that can serve multiple functions: they contain both ene and epoxide functional groups that can react with thiols, and they are derived from renewable resources. This multi-functionality allows a single sustainable feedstock to replace multiple petrochemical sources.
4Loss of substance
If click reactions are used for synthesizing thiol-ene and thiol-epoxy polymers, then waste is minimized and energy consumption is reduced, but the reactants must be free from solvent and air sensitivity limitations
Solution Approach 1:
The patent employs disposable protective groups that can be easily added and removed during the synthesis process. These temporary protective elements allow the reactants to be handled more easily during synthesis, then are discarded after serving their protective function, enabling the use of click reactions with minimal waste.
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 resulting polythiol compounds have a high biocarbon content and can be used in one or two-component curable compositions, offering a sustainable alternative for coatings, adhesives, and sealants with reduced waste and energy consumption.
Implementation Method 1
reacting, in the presence of at least one base, said compound of general Formula I with a primary allyl compound (II) to form a compound of Formula III
Implementation Method 2
reacting said compound of Formula III with a thiol acid (IV) to form a thioester compound of Formula V
Implementation Method 3
deprotecting said thioester compound of Formula V to form said polythiol compound of Formula VI
Data Source
AI summary
The present application is directed to a polythiol compound having the general Formula VI, wherein: m is an integer of from 4 to 600; n is an integer of from 4 to 400; 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.