Selective Hydrogenation of Trans,Trans-Muconic Acid to Adipic Acid over a Titania-Supported Rhenium Catalyst

ChemSusChem ◽  
2011 ◽  
Vol 4 (8) ◽  
pp. 1071-1073 ◽  
Author(s):  
Xiaoyan She ◽  
Heather M. Brown ◽  
Xiao Zhang ◽  
Birgitte K. Ahring ◽  
Yong Wang
Keyword(s):  
Adipic Acid ◽  
Selective Hydrogenation ◽  
Muconic Acid

scholarly journals Alkene hydrogenation activity of enoate reductases for an environmentally benign biosynthesis of adipic acid

2017 ◽  
Vol 8 (2) ◽  
pp. 1406-1413 ◽  
Author(s):  
Jeong Chan Joo ◽  
Anna N. Khusnutdinova ◽  
Robert Flick ◽  
Taeho Kim ◽  
Uwe T. Bornscheuer ◽  
...  
Keyword(s):  
Adipic Acid ◽  
Environmentally Benign ◽  
Muconic Acid ◽  
Hydrogenation Activity ◽  
Alkene Hydrogenation

We demonstrate the first enzymatic hydrogenation of 2-hexenedioic acid and muconic acid to adipic acid using enoate reductases (ERs).

scholarly journals Bio Adipic Acid Production from Sodium Muconate and Muconic Acid: A Comparison of two Systems

ChemCatChem ◽  
2019 ◽  
Vol 11 (13) ◽  
pp. 3075-3084 ◽  
Author(s):  
Sofia Capelli ◽  
Davide Motta ◽  
Claudio Evangelisti ◽  
Nikolaos Dimitratos ◽  
Laura Prati ◽  
...  
Keyword(s):  
Adipic Acid ◽  
Acid Production ◽  
Muconic Acid ◽  
Two Systems

scholarly journals Effect of Carbon Support, Capping Agent Amount, and Pd NPs Size for Bio-Adipic Acid Production from Muconic Acid and Sodium Muconate

Nanomaterials ◽  
2020 ◽  
Vol 10 (3) ◽  
pp. 505
Author(s):  
Sofia Capelli ◽  
Davide Motta ◽  
Claudio Evangelisti ◽  
Nikolaos Dimitratos ◽  
Laura Prati ◽  
...  
Keyword(s):  
Adipic Acid ◽  
Activated Carbons ◽  
Carbon Support ◽  
Pd Nanoparticles ◽  
Protective Agent ◽  
Capping Agent ◽  
Muconic Acid ◽  
Acid Yield ◽  
Substrate Conversion ◽  
Effect Of Support

The effect of support, stabilizing agent, and Pd nanoparticles (NPs) size was studied for sodium muconate and t,t-muconic acid hydrogenation to bio-adipic acid. Three different activated carbons (AC) were used (Norit, KB, and G60) and carbon morphology did not affect the substrate conversion, but it greatly influenced the adipic acid yield. 1% Pd/KB Darco catalyst, which has the highest surface area and Pd surface exposure, and the smallest NPs size displayed the highest activity. Furthermore, the effect of the amount of the protective agent was studied varying metal/protective agent weight ratios in the range of 1/0.00–1/1.20, using KB as the chosen support. For sodium muconate reduction 1% Pd/KB_1.2 catalyst gave the best results in terms of activity (0.73 s−1), conversion, and adipic acid yield (94.8%), while for t,t-muconic acid hydrogenation the best activity result (0.85 s−1) was obtained with 1% Pd/KB_0.0 catalyst. Correlating the results obtained from XPS and TEM analyses with catalytic results, we found that the amount of PVA (polyvinyl alcohol) influences mean Pd NPs size, Pd(0)/Pd(II) ratio, and Pd surface exposure. Pd(0)/Pd(II) ratio and Pd NPs size affected adipic acid yield and activity during sodium muconate hydrogenation, respectively, while adipic acid yield was related by exposed Pd amount during t,t-muconic acid hydrogenation. The synthesized catalysts showed higher activity than commercial 5% Pd/AC.

Phyllosilicate-Derived CuNi/SiO2 Catalysts in the Selective Hydrogenation of Adipic Acid to 1,6-Hexanediol

2019 ◽  
Vol 7 (21) ◽  
pp. 17872-17881 ◽  
Author(s):  
Cheng-Chieh Tu ◽  
Ya-Ju Tsou ◽  
Thien Dien To ◽  
Chao-Huang Chen ◽  
Jyh-Fu Lee ◽  
...  
Keyword(s):  
Adipic Acid ◽  
Selective Hydrogenation

scholarly journals Pd–Au Bimetallic Catalysts for the Hydrogenation of Muconic Acid to Bio-Adipic Acid

Catalysts ◽  
2021 ◽  
Vol 11 (11) ◽  
pp. 1313
Author(s):  
Sofia Capelli ◽  
Ilaria Barlocco ◽  
Federico Maria Scesa ◽  
Xiaohui Huang ◽  
Di Wang ◽  
...  
Keyword(s):  
Adipic Acid ◽  
Bimetallic Catalysts ◽  
Batch Reactor ◽  
Hydrogenation Reaction ◽  
Molar Ratio ◽  
Muconic Acid ◽  
Bimetallic Nanoparticle ◽  
Heat Treated ◽  
Temperature Heat ◽  
Treated Carbon

The hydrogenation reaction of muconic acid, produced from biomass using fermentative processes, to bio-adipic acid is one of the most appealing green emerging chemical process. This reaction can be promoted by catalysts based on a metal belonging to the platinum group, and the use of a second metal can preserve and increase their activity. Pd–Au bimetallic nanoparticle samples supported on high-temperature, heat-treated carbon nanofibers were prepared using the sol immobilization method, changing the Pd–Au molar ratio. These catalysts were characterized by TEM, STEM, and XPS analysis and tested in a batch reactor pressurized with hydrogen, where muconic acid dissolved in water was converted to adipic acid. The synthesized Pd–Au bimetallic catalysts showed higher activity than monometallic Au and Pd material and better stability during the recycling tests. Moreover, the selectivity toward the mono-unsaturated changed by decreasing the Pd/Au molar ratio: the higher the amount of gold, the higher the selectivity toward the intermediates.

scholarly journals Biosynthesis ofcis,cis-Muconic Acid and Its Aromatic Precursors, Catechol and Protocatechuic Acid, from Renewable Feedstocks by Saccharomyces cerevisiae

2012 ◽  
Vol 78 (23) ◽  
pp. 8421-8430 ◽  
Author(s):  
Christian Weber ◽  
Christine Brückner ◽  
Sheila Weinreb ◽  
Claudia Lehr ◽  
Christine Essl ◽  
...  
Keyword(s):  
Saccharomyces Cerevisiae ◽  
Amino Acid ◽  
Adipic Acid ◽  
Aromatic Amino Acid ◽  
Protocatechuic Acid ◽  
Amino Acid Biosynthesis ◽  
Biosynthesis Pathway ◽  
Acid Biosynthesis ◽  
Muconic Acid ◽  
Production Processes

ABSTRACTAdipic acid is a high-value compound used primarily as a precursor for the synthesis of nylon, coatings, and plastics. Today it is produced mainly in chemical processes from petrochemicals like benzene. Because of the strong environmental impact of the production processes and the dependence on fossil resources, biotechnological production processes would provide an interesting alternative. Here we describe the first engineeredSaccharomyces cerevisiaestrain expressing a heterologous biosynthetic pathway converting the intermediate 3-dehydroshikimate of the aromatic amino acid biosynthesis pathway via protocatechuic acid and catechol intocis,cis-muconic acid, which can be chemically dehydrogenated to adipic acid. The pathway consists of three heterologous microbial enzymes, 3-dehydroshikimate dehydratase, protocatechuic acid decarboxylase composed of three different subunits, and catechol 1,2-dioxygenase. For each heterologous reaction step, we analyzed several potential candidates for their expression and activity in yeast to compose a functionalcis,cis-muconic acid synthesis pathway. Carbon flow into the heterologous pathway was optimized by increasing the flux through selected steps of the common aromatic amino acid biosynthesis pathway and by blocking the conversion of 3-dehydroshikimate into shikimate. The recombinant yeast cells finally produced about 1.56 mg/litercis,cis-muconic acid.

Bimetallic Nanocatalysts for the Conversion of Muconic Acid to Adipic Acid.

ChemInform ◽  
2003 ◽  
Vol 34 (34) ◽  
Author(s):  
John Meurig Thomas ◽  
Robert Raja ◽  
Brian F. G. Johnson ◽  
Timothy J. O'Connell ◽  
Gopinathan Sankar ◽  
...  
Keyword(s):  
Adipic Acid ◽  
Muconic Acid ◽  
Bimetallic Nanocatalysts

Bio-adipic acid production by catalysed hydrogenation of muconic acid in mild operating conditions

2017 ◽  
Vol 218 ◽  
pp. 220-229 ◽  
Author(s):  
S. Capelli ◽  
A. Rosengart ◽  
A. Villa ◽  
A. Citterio ◽  
A. Di Michele ◽  
...  
Keyword(s):  
Adipic Acid ◽  
Acid Production ◽  
Operating Conditions ◽  
Muconic Acid

scholarly journals A Novel Muconic Acid Biosynthesis Approach by Shunting Tryptophan Biosynthesis via Anthranilate

2013 ◽  
Vol 79 (13) ◽  
pp. 4024-4030 ◽  
Author(s):  
Xinxiao Sun ◽  
Yuheng Lin ◽  
Qin Huang ◽  
Qipeng Yuan ◽  
Yajun Yan
Keyword(s):  
Adipic Acid ◽  
Scale Up ◽  
Carbon Sources ◽  
Shikimate Pathway ◽  
Tryptophan Biosynthesis ◽  
Regeneration System ◽  
Muconic Acid ◽  
Promising Alternative ◽  
Content Type ◽  
Catechol 1,2 Dioxygenase

ABSTRACTMuconic acid is the synthetic precursor of adipic acid, and the latter is an important platform chemical that can be used for the production of nylon-6,6 and polyurethane. Currently, the production of adipic acid relies mainly on chemical processes utilizing petrochemicals, such as benzene, which are generally considered environmentally unfriendly and nonrenewable, as starting materials. Microbial synthesis from renewable carbon sources provides a promising alternative under the circumstance of petroleum depletion and environment deterioration. Here we devised a novel artificial pathway inEscherichia colifor the biosynthesis of muconic acid, in which anthranilate, the first intermediate in the tryptophan biosynthetic branch, was converted to catechol and muconic acid by anthranilate 1,2-dioxygenase (ADO) and catechol 1,2-dioxygenase (CDO), sequentially and respectively. First, screening for efficient ADO and CDO from different microbial species enabled the production of gram-per-liter level muconic acid from supplemented anthranilate in 5 h. To further achieve the biosynthesis of muconic acid from simple carbon sources, anthranilate overproducers were constructed by overexpressing the key enzymes in the shikimate pathway and blocking tryptophan biosynthesis. In addition, we found that introduction of a strengthened glutamine regeneration system by overexpressing glutamine synthase significantly improved anthranilate production. Finally, the engineeredE. colistrain carrying the full pathway produced 389.96 ± 12.46 mg/liter muconic acid from simple carbon sources in shake flask experiments, a result which demonstrates scale-up potential for microbial production of muconic acid.

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