Adipic Acid

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Lisbeth Olsson - One of the best experts on this subject based on the ideXlab platform.

  • Biobased Adipic Acid – The challenge of developing the production host
    Biotechnology Advances, 2018
    Co-Authors: Emma Skoog, Veronica Saez-jimenez, Valeria Mapelli, Jae Ho Shin, Lisbeth Olsson
    Abstract:

    Adipic Acid is a platform chemical, and is the most important commercial dicarboxylic Acid. It has been targeted for biochemical conversion as an alternative to present chemical production routes. From the perspective of bioeconomy, several kinds of raw material are of interest including the sugar platform (derived from starch, cellulose or hemicellulose), the lignin platform (aromatics) and the fatty Acid platform (lipid derived). Two main biochemical-based production schemes may be employed: (i) direct fermentation to Adipic Acid, or (ii) fermentation to muconic or glucaric Acid, followed by chemical hydrogenation (indirect fermentation). This review presents a comprehensive description of the metabolic pathways that could be constructed and analyzes their respective theoretical yields and metabolic constraints. The experimental yields and titers obtained so far are low, with the exception of processes based on palm oil and glycerol, which have been reported to yield up to 50 g and 68 g Adipic Acid/L, respectively. The challenges that remain to be addressed in order to achieve industrially relevant production levels include solving redox constraints, and identifying and/or engineering enzymes for parts of the metabolic pathways that have yet to be metabolically demonstrated. This review provides new insights into ways in which metabolic pathways can be constructed to achieve efficient Adipic Acid production. The production host provides the chassis to be engineered via an appropriate metabolic pathway, and should also have properties suitable for the industrial production of Adipic Acid. An Acidic process pH is attractive to reduce the cost of downstream processing. The production host should exhibit high tolerance to complex raw material streams and high Adipic Acid concentrations at Acidic pH.

  • Adipic Acid tolerance screening for potential Adipic Acid production hosts
    Microbial cell factories, 2017
    Co-Authors: Emma Karlsson, Valeria Mapelli, Lisbeth Olsson
    Abstract:

    Biobased processes for the production of Adipic Acid are of great interest to replace the current environmentally detrimental petrochemical production route. No efficient natural producer of Adipic Acid has yet been identified, but several approaches for pathway engineering have been established. Research has demonstrated that the microbial production of Adipic Acid is possible, but the yields and titres achieved so far are inadequate for commercialisation. A plausible explanation may be intolerance to Adipic Acid. Therefore, in this study, selected microorganisms, including yeasts, filamentous fungi and bacteria, typically used in microbial cell factories were considered to evaluate their tolerance to Adipic Acid. Results: Screening of yeasts and bacteria for tolerance to Adipic Acid was performed in microtitre plates, and in agar plates for A. niger in the presence of Adipic Acid over a broad range of concentration (0-684 mM). As the different dissociation state(s) of Adipic Acid may influence cells differently, cultivations were performed with at least two pH values. Yeasts and A. niger were found to tolerate substantially higher concentrations of Adipic Acid than bacteria, and were less affected by the undissociated form of Adipic Acid than bacteria. The yeast exhibiting the highest tolerance to Adipic Acid was Candida viswanathii, showing a reduction in maximum specific growth rate of no more than 10-15% at the highest concentration of Adipic Acid tested and the tolerance was not dependent on the dissociation state of the Adipic Acid. Conclusions: Tolerance to Adipic Acid was found to be substantially higher among yeasts and A. niger than bacteria. The explanation of the differences in Adipic Acid tolerance between the microorganisms investigated are likely related to fundamental differences in their physiology and metabolism. Among the yeasts investigated, C. viswanathii showed the highest tolerance and could be a potential host for a future microbial cell factory for Adipic Acid.

  • METABOLIC ENGINEERING OF Saccharomyces cerevisiae FOR PRODUCTION OF Adipic Acid FROM RENEWABLE SOURCES
    2014
    Co-Authors: Emma Karlsson, Valeria Mapelli, Luigi D’avino, Lisbeth Olsson
    Abstract:

    Adipic Acid is a six carbon long dicarboxylic Acid, considered to be the most important synthetic dicarboxylic Acid annually produced, according to the International Energy Agency (IEA). The global production of Adipic Acid had in 2010 a volume of 2.8 million tonnes, for a total market price of 4.9 billion USD. The current production of Adipic Acid relies on non-renewable fossil raw materials, leading to emission of the greenhouse gases carbon dioxide and N2O. In addition, the production starts from benzene, whose use has several health related negative implications. This project aims to create a greener process for production of Adipic Acid developing a fermentation-based process using Swedish domestic renewable raw materials, such as forest residues and/or algae. These materials will be used to establish a biorefinery, wherein the fermentation process for the biosynthesis of Adipic Acid will represent the core process. Our current strategy is based on the generation of genetically modified strains of the yeast Saccharomyces cerevisiae, harbouring heterologous enzymatic activities allowing the conversion of lysine into Adipic Acid. This system is our first choice and will also work as proof-of-concept for bio-based production of Adipic Acid. Here we present the metabolic engineering strategy we are pursuing, based on two possible metabolic pathways for conversion of lysine into Adipic Acid. Preliminary results on the effect of Adipic Acid on S. cerevisiae physiology, lysine uptake, the expression of the heterologous genes of choice, and the conversion of lysine into Adipic Acid precursors are presented.

Robert P. Anex - One of the best experts on this subject based on the ideXlab platform.

  • techno economic analysis of multiple bio based routes to Adipic Acid
    Biofuels Bioproducts and Biorefining, 2017
    Co-Authors: Sampath Gunukula, Robert P. Anex
    Abstract:

    Techno-economic studies of four processes for production of Adipic Acid from glucose were used to compare the minimum cost of production by each route. We analyzed the purely biological production via reverse β-oxidation in E. coli; a purely chemical process using oxidation of glucose via chemical catalysis to glucaric Acid that undergoes catalytic hydrodeoxygenation to Adipic Acid; and two hybrid routes that biologically convert glucose to either 6-hydroxyhexanoic Acid or 1, 6-hexanediol, that are subsequently converted chemically to Adipic Acid using a metal catalyst. All analyses were based on Adipic Acid production capacity of 80 000 metric ton/year. Estimated total capital investments were US$157 million, $81 million, $166 million, and $177 million for the purely ­biological, chemical, and two integrated hybrid routes, respectively. Catalyst costs were estimated as $72 million, $36 million, and $37 million for the purely chemical and two integrated routes, respectively. The estimated Adipic Acid minimum selling prices were $1.36, $1.56, $1.48, and $1.70 per kg for the purely biological, purely chemical, and two integrated routes, respectively. Co-product revenue and the use of unpurified sugars improved the economics of Adipic Acid production in the purely biological and two integrated routes. Comparison of the economics of the chemical catalytic steps shows that catalyst yields, turnover frequency, and catalyst life must be greater than 40% of theoretical, 0.01 s-1, and 100 days to achieve economic viability of purely chemical and integrated routes to Adipic Acid. © 2017 Society of Chemical Industry and John Wiley & Sons, Ltd.

  • Techno‐economic analysis of multiple bio‐based routes to Adipic Acid
    Biofuels Bioproducts and Biorefining, 2017
    Co-Authors: Sampath Gunukula, Robert P. Anex
    Abstract:

    Techno-economic studies of four processes for production of Adipic Acid from glucose were used to compare the minimum cost of production by each route. We analyzed the purely biological production via reverse β-oxidation in E. coli; a purely chemical process using oxidation of glucose via chemical catalysis to glucaric Acid that undergoes catalytic hydrodeoxygenation to Adipic Acid; and two hybrid routes that biologically convert glucose to either 6-hydroxyhexanoic Acid or 1, 6-hexanediol, that are subsequently converted chemically to Adipic Acid using a metal catalyst. All analyses were based on Adipic Acid production capacity of 80 000 metric ton/year. Estimated total capital investments were US$157 million, $81 million, $166 million, and $177 million for the purely ­biological, chemical, and two integrated hybrid routes, respectively. Catalyst costs were estimated as $72 million, $36 million, and $37 million for the purely chemical and two integrated routes, respectively. The estimated Adipic Acid minimum selling prices were $1.36, $1.56, $1.48, and $1.70 per kg for the purely biological, purely chemical, and two integrated routes, respectively. Co-product revenue and the use of unpurified sugars improved the economics of Adipic Acid production in the purely biological and two integrated routes. Comparison of the economics of the chemical catalytic steps shows that catalyst yields, turnover frequency, and catalyst life must be greater than 40% of theoretical, 0.01 s-1, and 100 days to achieve economic viability of purely chemical and integrated routes to Adipic Acid. © 2017 Society of Chemical Industry and John Wiley & Sons, Ltd.

Andrea Corona - One of the best experts on this subject based on the ideXlab platform.

  • life cycle assessment of Adipic Acid production from lignin
    Green Chemistry, 2018
    Co-Authors: Andrea Corona, Mary J Biddy, Derek R Vardon, Morten Birkved, Michael Zwicky Hauschild, Gregg T Beckham
    Abstract:

    Lignin is a heterogeneous, aromatic polymer and one of the main components of plant biomass. Current lignocellulosic biorefineries primarily focus on polysaccharide conversion from biomass, and separate and combust the residual lignin for heat and power. By using lignin only as a fuel, this polysaccharide-centric approach potentially limits the valorization potential of biomass feedstocks. In this study, we performed a life cycle assessment (LCA) on an emerging lignin upgrading process, namely the production of bio-based Adipic Acid from lignin sourced from bioethanol production, relative to the conventional petrochemical production pathway. The LCA predicts an overall lower environmental impact for the bio-based route, primarily due to the utilization of a biorefinery side-stream as feedstock material and in the avoidance of nitrous oxide emissions. Bio-based Adipic Acid is predicted to lead to 4.87 kg CO2 eq. per kgAA for greenhouse gas emissions, which is a reduction of −62% to −78% compared to conventional Adipic Acid. Furthermore, results from the sensitivity analysis identify sodium hydroxide utilization and heating needs as the inputs that contribute the largest environmental burden in the bio-based process. Alternative lignin depolymerization processes and development of microbial strains that can tolerate low pH are possible optimization strategies to further improve the environmental profile of bio-based Adipic Acid. The effects of the LCA modeling assumptions on the environmental profile of bio-based Adipic Acid are also examined, demonstrating that the electricity footprint and the assumptions made to estimate the effects of diverting lignin from energy to material production play an important role in the model predictions. More broadly, this study highlights that partial lignin conversion to select chemicals in biorefineries may be more environmentally beneficial than solely producing bio-power through combustion, which is the current biorefinery paradigm for lignin utilization.

Radhakrishnan Mahadevan - One of the best experts on this subject based on the ideXlab platform.

  • Biocatalytic production of Adipic Acid from glucose using engineered Saccharomyces cerevisiae.
    Metabolic engineering communications, 2018
    Co-Authors: Kaushik Raj, Siavash Partow, Kevin Correia, Anna N. Khusnutdinova, Alexander F. Yakunin, Radhakrishnan Mahadevan
    Abstract:

    Adipic Acid is an important industrial chemical used in the synthesis of nylon-6,6. The commercial synthesis of Adipic Acid uses petroleum-derived benzene and releases significant quantities of greenhouse gases. Biocatalytic production of Adipic Acid from renewable feedstocks could potentially reduce the environmental damage and eliminate the need for fossil fuel precursors. Recently, we have demonstrated the first enzymatic hydrogenation of muconic Acid to Adipic Acid using microbial enoate reductases (ERs) - complex iron-sulfur and flavin containing enzymes. In this work, we successfully expressed the Bacillus coagulans ER in a Saccharomyces cerevisiae strain producing muconic Acid and developed a three-stage fermentation process enabling the synthesis of Adipic Acid from glucose. The ability to express active ERs and significant Acid tolerance of S. cerevisiae highlight the applicability of the developed yeast strain for the biocatalytic production of Adipic Acid from renewable feedstocks.

  • Biocatalytic production of Adipic Acid from glucose using engineered Saccharomyces cerevisiae
    Elsevier, 2018
    Co-Authors: Kaushik Raj, Siavash Partow, Kevin Correia, Anna N. Khusnutdinova, Alexander F. Yakunin, Radhakrishnan Mahadevan
    Abstract:

    Adipic Acid is an important industrial chemical used in the synthesis of nylon-6,6. The commercial synthesis of Adipic Acid uses petroleum-derived benzene and releases significant quantities of greenhouse gases. Biocatalytic production of Adipic Acid from renewable feedstocks could potentially reduce the environmental damage and eliminate the need for fossil fuel precursors. Recently, we have demonstrated the first enzymatic hydrogenation of muconic Acid to Adipic Acid using microbial enoate reductases (ERs) - complex iron-sulfur and flavin containing enzymes. In this work, we successfully expressed the Bacillus coagulans ER in a Saccharomyces cerevisiae strain producing muconic Acid and developed a three-stage fermentation process enabling the synthesis of Adipic Acid from glucose. The ability to express active ERs and significant Acid tolerance of S. cerevisiae highlight the applicability of the developed yeast strain for the biocatalytic production of Adipic Acid from renewable feedstocks. Keywords: Biosynthesis, Renewable resources, Yeast, Adipic Acid, Synthetic biolog

  • Alkene hydrogenation activity of enoate reductases for an environmentally benign biosynthesis of Adipic Acid.
    Chemical science, 2016
    Co-Authors: Jeong Chan Joo, Anna N. Khusnutdinova, Alexander F. Yakunin, Robert Flick, Taeho Kim, Uwe T. Bornscheuer, Radhakrishnan Mahadevan
    Abstract:

    Adipic Acid, a precursor for Nylon-6,6 polymer, is one of the most important commodity chemicals, which is currently produced from petroleum. The biosynthesis of Adipic Acid from glucose still remains challenging due to the absence of biocatalysts required for the hydrogenation of unsaturated six-carbon dicarboxylic Acids to Adipic Acid. Here, we demonstrate the first enzymatic hydrogenation of 2-hexenedioic Acid and muconic Acid to Adipic Acid using enoate reductases (ERs). ERs can hydrogenate 2-hexenedioic Acid and muconic Acid producing Adipic Acid with a high conversion rate and yield in vivo and in vitro. Purified ERs exhibit a broad substrate spectrum including aromatic and aliphatic 2-enoates and a significant oxygen tolerance. The discovery of the hydrogenation activity of ERs contributes to an understanding of the catalytic mechanism of these poorly characterized enzymes and enables the environmentally benign biosynthesis of Adipic Acid and other chemicals from renewable resources.

Gregg T Beckham - One of the best experts on this subject based on the ideXlab platform.

  • life cycle assessment of Adipic Acid production from lignin
    Green Chemistry, 2018
    Co-Authors: Andrea Corona, Mary J Biddy, Derek R Vardon, Morten Birkved, Michael Zwicky Hauschild, Gregg T Beckham
    Abstract:

    Lignin is a heterogeneous, aromatic polymer and one of the main components of plant biomass. Current lignocellulosic biorefineries primarily focus on polysaccharide conversion from biomass, and separate and combust the residual lignin for heat and power. By using lignin only as a fuel, this polysaccharide-centric approach potentially limits the valorization potential of biomass feedstocks. In this study, we performed a life cycle assessment (LCA) on an emerging lignin upgrading process, namely the production of bio-based Adipic Acid from lignin sourced from bioethanol production, relative to the conventional petrochemical production pathway. The LCA predicts an overall lower environmental impact for the bio-based route, primarily due to the utilization of a biorefinery side-stream as feedstock material and in the avoidance of nitrous oxide emissions. Bio-based Adipic Acid is predicted to lead to 4.87 kg CO2 eq. per kgAA for greenhouse gas emissions, which is a reduction of −62% to −78% compared to conventional Adipic Acid. Furthermore, results from the sensitivity analysis identify sodium hydroxide utilization and heating needs as the inputs that contribute the largest environmental burden in the bio-based process. Alternative lignin depolymerization processes and development of microbial strains that can tolerate low pH are possible optimization strategies to further improve the environmental profile of bio-based Adipic Acid. The effects of the LCA modeling assumptions on the environmental profile of bio-based Adipic Acid are also examined, demonstrating that the electricity footprint and the assumptions made to estimate the effects of diverting lignin from energy to material production play an important role in the model predictions. More broadly, this study highlights that partial lignin conversion to select chemicals in biorefineries may be more environmentally beneficial than solely producing bio-power through combustion, which is the current biorefinery paradigm for lignin utilization.