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Metabolic Engineering for the Production of a Variety of Biofuels and Biochemicals
Published in Kazuyuki Shimizu, Metabolic Regulation and Metabolic Engineering for Biofuel and Biochemical Production, 2017
Adipic acid or hexanedioic acid (C6H10O4) with a molecular weight of 146.14 is the commercial aliphatic dicarboxylic acid (Musser 2005). The primal application of adipic acid is in the chemical production of nylon-6,6 polyamide. Adipic acid is also used to produce polyurethane, as a reactant to form plasticizers, lubricant components and polyester polyols. Others are a food ingredient in gelatins, desserts and other foods that require acidulation (Polen et al. 2013).
Recent Developments in Biorefinery Catalysis
Published in Deniz Uner, Advances in Refining Catalysis, 2017
Elif Ispir Gurbuz, Nazife Işık Semerci
Adipic acid is a versatile building block in the chemical, pharmaceutical, and food industries, and one of the most common commodity chemicals worldwide, with a projected market size of more than 6 million lbs. by 2017 (Weissermel and Arpe 2003). Adipic acid has use in the production of polyester, polyurethane, polyvinyl chloride, cosmetics, adhesives, lubricants, and insecticides, but its primary use lies in the production of the polyamide Nylon-6,6 (Casanova et al. 2009). Currently, adipic acid is produced from the catalytic oxidation of a mixture of cyclohexanol and cyclohexanone obtained from petroleum via an inefficient catalytic process (Castellan et al. 1991; Chaminand et al. 2004; Welch et al. 2005; Hermans et al. 2006; Casanova et al. 2009; Cherubini 2010; Gursel et al. 2012). As a result, adipic acid has attracted a significant amount of attention from the academic and industrial catalysis community as a potential “drop-in” chemical to be produced in a more efficient and sustainable manner from lignocellulose (Van de Vyver and Roman-Leshkov 2013). Many US-based start-up companies, such as Verdezyne, Rennovia, and BioAmber, have declared ongoing initiatives to enter the adipic acid market. Several processes have been developed starting from glucose involving different intermediates, such as glucaric acid, 5-HMF, and GVL. Rennovia, a US start-up company that specializes in the development of sustainable production routes of chemicals from biomass, disclosed a patent for the production of adipic acid from glucose through the intermediate production of glucaric acid (Scheme 10.4a) (Cherubini and Stromman 2011). Oxidation of glucose to glucaric acid in aqueous phase, in this process, is carried out on Pt-based catalysts at 363 K and 5 bar of O2, in absence of any base, reaching high yields (~70%). Following its production, glucaric acid undergoes a HDO reaction on bimetallic Pt–Rh based catalysts in the presence of HBr and acetic acid at 413 K and 49 bar of H2 to form adipic acid with yields up to 90%.
Synthesis Plan Analysis
Published in John Andraos, Synthesis Green Metrics, 2018
Adipic acid is a high commodity industrial volume chemical used to make nylon polymer. One traditional way of making it is by oxidizing cyclohexanol in the presence of nitric acid. A new green chemical route and a biosynthetic route have been developed to address the problem of noxious by-products made in the traditional method.
Synthesis and characterization of naphthaldiimine-based ruthenium(III) complexes; homogenous catalytic hydrogenation and isomerization of internal and terminal alkenes
Published in Journal of Coordination Chemistry, 2022
Ahmed M. Fathy, Mahmoud M. Hessien, Mohamed M. Ibrahim, Abd El-Motaleb M. Ramadan
DMF has been used in many catalytic hydrogenation reactions and has been considered an influential factor in determining the course of catalytic hydrogenation reactions [57] and DMF was used here. Regarding the different solvents used in the ongoing study, the data in S28 indicate that the solubility of H2 depends on the type and quantity of the individual solvent, as well as the type and quantity of the solvent mixture and the ratio of its components. Cyclohexene is the model for simple alkenes because the hydrogenation process gives a single product that is not accompanied by by-products, facilitating study of the mechanism. Catalytic hydrogenation of cyclohexene produces cyclohexane, which is used in the manufacture of adipic acid (Figure 8), a raw material for polyamides used in the industrial production of polymers such as nylon [58].
Green and mild oxidation: from acetate anion to oxalate anion
Published in Journal of Coordination Chemistry, 2018
Lu-Yi Zheng, Yan-Hui Chi, Yuan Liang, Ethan Cottrill, Ning Pan, Jing-Min Shi
The synthesis of valuable oxygen-containing compounds such as alcohols, ketones and carboxylic acids is an important subject in organic chemistry. Classically, the preparations involve oxidizing alkyl groups with inorganic oxidizing agents like chromium oxides [1, 2], manganese oxides [3], halogens [4], and nitric acid [5]. In recent years, the synthetic strategy has focused on more green and mild conditions, environmental benignity, and sustainability [6–9]. In this area, molecular oxygen or air is the ideal oxidant—since either is superior in economy, environmental acceptance, and sustainability—and major advances have been made [10–13]. For example, cyclohexane can be oxidized by molecular oxygen to yield a mixture of cyclohexanone and adipic acid [14], and isobutene can be oxidized by air to yield a mixture of tert-butyl alcohol and acetone [15]. In these reactions, transition metal complexes play key roles as catalysts [16–19]. However, many oxidation reactions involving molecular oxygen or air as the oxidizing agent are constrained to preparing ketones or aldehydes from alcohols [20, 21]. Only a few examples deal with oxidizing alkyl groups to carboxylic groups [10–14]; these typically require high temperature and/or high pressure. The development of green and mild reaction conditions to oxidize alkyl groups to carboxylic groups is an important challenge in organic chemistry, catalytic chemistry and coordination chemistry.
Separation of the Minor Actinides Americium(III) and Curium(III) by Hydrophobic and Hydrophilic BTPhen ligands: Exploiting Differences in their Rates of Extraction and Effective Separations at Equilibrium
Published in Solvent Extraction and Ion Exchange, 2018
Frank W. Lewis, Laurence M. Harwood, Michael J. Hudson, Ashfaq Afsar, Dominic M. Laventine, Kamila Šťastná, Jan John, Petr Distler
Having studied the separation of Am(III) from Cm(III) by CyMe4–BTPhen 3 in 1-octanol and 1-octanol/toluene mixtures, we next elected to study the extraction of Am(III) and Cm(III) by CyMe4–BTPhen 3 using cyclohexanone as the diluent. This diluent has been proposed for processing spent nuclear fuels and has the advantage that extraction equilibrium is achieved more rapidly than with 1-octanol (equilibrium is typically reached within 10 min for CyMe4–BTBP 2 in cyclohexanone, vs. >1 h in 1-octanol).[58–60] On the other hand, the known reaction of cyclohexanone with nitric acid to produce adipic acid[61] raises safety concerns with respect to using this diluent in future spent fuel reprocessing. The extraction of Am(III) and Cm(III) by CyMe4–BTPhen 3 in cyclohexanone as a function of the nitric acid concentration of the aqueous phase is presented in Figure 7.