Thermodynamics of cis,cis-muconic acid solubility in various polar solvents at low temperature range

Scelfo, Simone; Pirone, Raffaele; Russo, Nunzio

doi:10.1016/j.molliq.2016.07.129

Cited by 8 publications

(5 citation statements)

References 36 publications

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“…7 A). To determine the amount of muconic acid in the PPG layer, we separated the layer from the aqueous phase and washed it with 4 mL 50% ethanol [ 54 ], and measured the muconic acid concentration in the ethanol using HPLC analysis. This showed that almost equal amounts of muconic acid could be recovered from the PPG phase compared to the amount present in the fermentation medium (Fig.…”

Section: Resultsmentioning

confidence: 99%

In-situ muconic acid extraction reveals sugar consumption bottleneck in a xylose-utilizing Saccharomyces cerevisiae strain

et al. 2021

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Background The current shift from a fossil-resource based economy to a more sustainable, bio-based economy requires development of alternative production routes based on utilization of biomass for the many chemicals that are currently produced from petroleum. Muconic acid is an attractive platform chemical for the bio-based economy because it can be converted in chemicals with wide industrial applicability, such as adipic and terephthalic acid, and because its two double bonds offer great versatility for chemical modification. Results We have constructed a yeast cell factory converting glucose and xylose into muconic acid without formation of ethanol. We consecutively eliminated feedback inhibition in the shikimate pathway, inserted the heterologous pathway for muconic acid biosynthesis from 3-dehydroshikimate (DHS) by co-expression of DHS dehydratase from P. anserina, protocatechuic acid (PCA) decarboxylase (PCAD) from K. pneumoniae and oxygen-consuming catechol 1,2-dioxygenase (CDO) from C. albicans, eliminated ethanol production by deletion of the three PDC genes and minimized PCA production by enhancing PCAD overexpression and production of its co-factor. The yeast pitching rate was increased to lower high biomass formation caused by the compulsory aerobic conditions. Maximal titers of 4 g/L, 4.5 g/L and 3.8 g/L muconic acid were reached with glucose, xylose, and a mixture, respectively. The use of an elevated initial sugar level, resulting in muconic acid titers above 2.5 g/L, caused stuck fermentations with incomplete utilization of the sugar. Application of polypropylene glycol 4000 (PPG) as solvent for in situ product removal during the fermentation shows that this is not due to toxicity by the muconic acid produced. Conclusions This work has developed an industrial yeast strain able to produce muconic acid from glucose and also with great efficiency from xylose, without any ethanol production, minimal production of PCA and reaching the highest titers in batch fermentation reported up to now. Utilization of higher sugar levels remained conspicuously incomplete. Since this was not due to product inhibition by muconic acid or to loss of viability, an unknown, possibly metabolic bottleneck apparently arises during muconic acid fermentation with high sugar levels and blocks further sugar utilization.

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Section: Resultsmentioning

confidence: 99%

In-situ muconic acid extraction reveals sugar consumption bottleneck in a xylose-utilizing Saccharomyces cerevisiae strain

et al. 2021

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“…The muconic acid is acidified and recovered via low temperature crystallization in the acid form [122]. Existing and predicted solubility curves for muconic acid and adipic acid shown in Figure 15 illustrate the strong temperature dependency of solubility for the fully protonated species [130,131]. At temperatures above the freezing point of water, fully protonated muconic acid (and adipic) will crystallize forming a high purity solid phase that can be easily removed via centrifugation from the residual liquid broth.…”

Section: Figure 14 Aerobic Bubble Column Bioreactor Setupmentioning

confidence: 99%

Process Design and Economics for the Conversion of Lignocellulosic Biomass to Hydrocarbon Fuels and Coproducts: 2018 Biochemical Design Case Update; Biochemical Deconstruction and Conversion of Biomass to Fuels and Products via Integrated Biorefinery Pathways

et al. 2018

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“…Tertiary amines and ionic liquids have strong extractability, but because they are viscous and corrosive, they must always be utilized with a diluent that also influences the organic phase's physical characteristics, including density, viscosity, and surface tension. Over a temperature range of 25 to 75 • C, the solubility data of muconic acid (cis-cis) in polar solvents such as water, ethanol, 2-propanol, and acetic acid have been calculated by Scelfo et al [53]. The results proved an exothermic process, increased solubility with rising temperature for the investigated domain, and the following order for solvent efficiency: water < acetic acid < 2-propanol < ethanol.…”

Section: Solvent Screeningmentioning

confidence: 99%

“…The central nitrogen atom of the amine forms the H-bond with the acid's hydroxyl group (Figure 5). The formation of this bond is facilitated by the central nitrogen atom's higher negative polarization [50][51][52][53][54][55], affected by both the number of bond carbon chains (greatest impact) and the length of the carbon chains. For the di-octylamine, negative polarization and reduced steric hindrance toward the central nitrogen atom enable the formation of complexes involving two MA molecules with high yields at low amine concentrations.…”

Section: Reactive Extraction Mechanismmentioning

confidence: 99%

Recent Advances in Muconic Acid Extraction Process

Blaga,

Gal,

Tucaliuc

2023

Applied Sciences

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Due to its potential use in the production of new functional resins, bio-plastics, food additives, agrochemicals, and pharmaceuticals, muconic acid (MA), a high value-added bio-product with reactive dicarboxylic groups and conjugated double bonds, has attracted growing interest. Adipic acid, terephthalic acid, and trimellitic acid are examples of bulk compounds that can be produced using MA that are of high commercial importance. The development of biotechnological approaches for MA production has advanced greatly recently. The current analysis offers a thorough and organized summary of recent developments and difficulties in the extraction of MA. A variety of extractants are presented, along with any limitations and potential solutions. Finally, the possibilities for this field in light of its state, difficulties, and tendencies are explored.

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Thermodynamics of cis,cis-muconic acid solubility in various polar solvents at low temperature range

Cited by 8 publications

References 36 publications

In-situ muconic acid extraction reveals sugar consumption bottleneck in a xylose-utilizing Saccharomyces cerevisiae strain

In-situ muconic acid extraction reveals sugar consumption bottleneck in a xylose-utilizing Saccharomyces cerevisiae strain

Process Design and Economics for the Conversion of Lignocellulosic Biomass to Hydrocarbon Fuels and Coproducts: 2018 Biochemical Design Case Update; Biochemical Deconstruction and Conversion of Biomass to Fuels and Products via Integrated Biorefinery Pathways

Recent Advances in Muconic Acid Extraction Process

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