Periodic Reporting for period 1 - SE (Development of a novel method for a simultaneous production of 2-butene and degradable polyesters from biomass)
Período documentado: 2022-03-01 hasta 2024-02-29
What is the problem/issue being addressed?
The project addresses valorization of largely unvalorized part of wood, namely - lignin. Lignin is considered as a side product of pulp and paper industry and find only low-key application as a heat source. Lignin is a macromolecule which has a great potential to generate bio-based analogs for materials and commodities to substitute their petroleum-based counterparts. In this project we developed a methodology to concomitantly produce a bio-based substitute for bisphenol A (BPA) and butene-2 from lignin. BPA is widely used as a plasticizer and a monomer for production of polyesters and polycarbonates. However, a crude oil origin of BPA and its high toxicity raised multiple concerns and are calling for the development of a substitute. Butene-2 is a valuable light olefin, currently almost entirely produced from crude oil. Bio-based routes to butene-2 are very limited and energy intensive. Overall, the process illustrates a high atom efficacy in conversion of bio-derived molecules into final product via valorization of all carbon atoms.
Why is it important for society?
Transition to a fossil fuel-free economy is one of the major goals for the global development and is reflected in several European initiatives e.g. European Green Deal. Development of pathways for a direct upgrading of biomass into final products is of paramount importance for this transition. Competition with crude oil-based products is burdened by a well-established structure of the petroleum industry, which has been optimized for many decades. This results in lower production prices for crude oil-based commodities difficult to compete with. Understanding of fundamental aspects of biomass conversion can help to develop novel optimized efficient methods for the biomass upgrading and as such to bring biorefinery closer to life.
What are the overall objectives?
Overall objectives of the described herein project include:
-Set-up specific optimization of reductive catalytic fractionation (RCF) of birch wood to generate iso-eugenol and propenyl syringol enriched lignin depolymerization oil
-Optimization of olefin metathesis step of IE and PS to generate targeted bisphenols (substitutes for BPA) and butene-2
-Production of materials (polyesters) based on the obtained BPA-substitute
-Application of the developed protocol directly to biomass: from wood to polyesters pathway
The project addresses valorization of largely unvalorized part of wood, namely - lignin. Lignin is considered as a side product of pulp and paper industry and find only low-key application as a heat source. Lignin is a macromolecule which has a great potential to generate bio-based analogs for materials and commodities to substitute their petroleum-based counterparts. In this project we developed a methodology to concomitantly produce a bio-based substitute for bisphenol A (BPA) and butene-2 from lignin. BPA is widely used as a plasticizer and a monomer for production of polyesters and polycarbonates. However, a crude oil origin of BPA and its high toxicity raised multiple concerns and are calling for the development of a substitute. Butene-2 is a valuable light olefin, currently almost entirely produced from crude oil. Bio-based routes to butene-2 are very limited and energy intensive. Overall, the process illustrates a high atom efficacy in conversion of bio-derived molecules into final product via valorization of all carbon atoms.
Why is it important for society?
Transition to a fossil fuel-free economy is one of the major goals for the global development and is reflected in several European initiatives e.g. European Green Deal. Development of pathways for a direct upgrading of biomass into final products is of paramount importance for this transition. Competition with crude oil-based products is burdened by a well-established structure of the petroleum industry, which has been optimized for many decades. This results in lower production prices for crude oil-based commodities difficult to compete with. Understanding of fundamental aspects of biomass conversion can help to develop novel optimized efficient methods for the biomass upgrading and as such to bring biorefinery closer to life.
What are the overall objectives?
Overall objectives of the described herein project include:
-Set-up specific optimization of reductive catalytic fractionation (RCF) of birch wood to generate iso-eugenol and propenyl syringol enriched lignin depolymerization oil
-Optimization of olefin metathesis step of IE and PS to generate targeted bisphenols (substitutes for BPA) and butene-2
-Production of materials (polyesters) based on the obtained BPA-substitute
-Application of the developed protocol directly to biomass: from wood to polyesters pathway
The work performed from the beginning of the project include:
- set-up specific optimization of catalytic fractionation of wood to enable separation (and depolymerization) of lignin from cellulose and hemicellulose
- isolation of low molecular weight products of depolymerized lignin oil
- identification and quantification of the products of depolymerization of lignin
- development of a catalytic conversion of target products from lignin depolymerization into BPA substitutes (reaction on model substrates: iso-eugenol, propenyl syringol)
- identification of the effect of impurities in lignin oil on the catalytic transformation of target molecules (iso-eugenol and propenyl syringol) into BPA-substitutes
- understanding of the mechanism of the catalyst poisoning by the relevant impurities
- development of in situ conversion of relevant impurities (catalyst poisonings) into catalytically inert species
- application of the developed on model compounds method to a realistic substrate - depolymerized lignin oil
- isolation of final bio-based BPA substitutes
- demonstration of synthetic utility of the developed BPA substitutes for the generation of polyesters
- set-up specific optimization of catalytic fractionation of wood to enable separation (and depolymerization) of lignin from cellulose and hemicellulose
- isolation of low molecular weight products of depolymerized lignin oil
- identification and quantification of the products of depolymerization of lignin
- development of a catalytic conversion of target products from lignin depolymerization into BPA substitutes (reaction on model substrates: iso-eugenol, propenyl syringol)
- identification of the effect of impurities in lignin oil on the catalytic transformation of target molecules (iso-eugenol and propenyl syringol) into BPA-substitutes
- understanding of the mechanism of the catalyst poisoning by the relevant impurities
- development of in situ conversion of relevant impurities (catalyst poisonings) into catalytically inert species
- application of the developed on model compounds method to a realistic substrate - depolymerized lignin oil
- isolation of final bio-based BPA substitutes
- demonstration of synthetic utility of the developed BPA substitutes for the generation of polyesters
The impact of the project goes beyond the valorization of lignin. It exemplifies a novel approach for a rational design to overcome a complexity of the biomass feedstock for production of final products. The simplicity of the protocol relying on selective transformations and system tuning rather than on tedious purifications will hopefully have a wide impact on transition towards bio-based economy. Important to mention here that the developed method produces molecules amenable for further transformations and diversifications. Thus, these molecules can be considered as "platform", meaning a possibility for their facile conversion into various derivatives. The developed method goes beyond generation of particular substitutes for BPA, but allows for the generation of libraries of the bisphenol compounds. This in combination with computational, toxicological and material science approaches will hopefully lead to rational design of bio-based materials with low toxicity for each specific application.
The developed methodology will significantly advance the transition towards biobased materials away from petroleum-based products. This will impact social-economic aspects associated with the use of petroleum: greenhouse gasses emissions, crude oil spills, ect.
Moreover, due to a known endocrine disruptor activity of BPA, materials containing BPA face bans around the world. Substituting BPA with a non toxic bio-based analog will bring additional societal benefits such as improvement of general public health, reduced pollution of the environment, etc.
The developed methodology will significantly advance the transition towards biobased materials away from petroleum-based products. This will impact social-economic aspects associated with the use of petroleum: greenhouse gasses emissions, crude oil spills, ect.
Moreover, due to a known endocrine disruptor activity of BPA, materials containing BPA face bans around the world. Substituting BPA with a non toxic bio-based analog will bring additional societal benefits such as improvement of general public health, reduced pollution of the environment, etc.