Adipic acid from D-glucose

Draths, K. M. Frost, J. W. Environmentally Compatible Synthesis of Adipic Acid from D-Glucose, J. Am. Chem. Soc. 1994,116, 399-400. 

Draths KM, Frost JW (1994) Environmentally compatible synthesis of adipic acid from D-glucose. J Am Chem Soc 116 399... 

Four billion pounds of adipic acid are produced each year using petroleum-based feedstocks, carcinogenic benzene as starting material, and extreme reaction conditions. Nitrous oxide, which plays a role in ozone layer depletion, is emitted as a byproduct. As an alternative to the currently employed synthetic methcdology, a two-step synthesis of adipic acid from D-glucose has been developed which eliminates each of these problems. A microbial catalyst was created which possesses a novel biosynthetic pathway that synthesizes cis, cis-muconic acid from D-glucose. This pathway does not occur in nature but has been created in a strain of Escherichia colL Cis, cw-muconic acid is exported to the culture supernatant, where it is hydrogenated under mild conditions to yield adipic acid. 

Figure 1. Comparison of current industrial synthesis of adipic acid from benzene (a-c) to syndiesis of adipic acid from D-glucose (d, e). (a) Ni-Al203, 370-800 psi, 150-250°C (b) Co, O2, 120-140 psi, 150-160°C. (c) Cu, NH4VO3, 60% HNO3, 60-80OQ (d) E. coli AB2834 iro /pKD136/ pKD8.243A/pKD8.292. (e) 10% Pt on carbon, H2, 50 psi. (Adapted and reproduced with permission from ref. 21.)...

Before it will be practical to consider using a microbial catalyst to manufacture adipic acid, significant challenges must be addressed. To improve catalyst stability and increase the percent conversion of D-glucose into product, further development of the microbial catalyst will be needed. The scale of the reaction also requires adjustment from laboratory shake flasks to fermentation tanks, which would then be readily scaled to industrial production. Future efforts will focus on these challenges. 

In the shikimic acid area, the conversion of D-glucose into the industrially important compound adipic acid using mutant enzymes derived from the shikimate pathway has been reported." ... 

Sucrose acrylate was synthesized by enzymatic catalysis using an enzyme proleather (a protease from Bacillus Sp.) (Patil et al, 1991a). The sucrose acrylate was polymerized using potassium persulfate/hydrogen peroxide to obtain poly(sucrose acrylate). Tokiwa et al (2000) reported esterification of glucose with adipic acid enzymatically and later on effected its polymerization by conventional methods to obtain biodegradable polymers. Similarly, a-D-galactose was acryloylated with vinyl acrylate enzymatically and later polymerized chemically. 

Furan-2,5-dicarboxylic add also has tremendous industrial potential, because it could replace oil-derived diadds such as adipic or terephthalic acid as monomers for polyesters and polyamides [98, 99]. This diadd can be synthesized by Pt-catalyzed oxidation with 02 of 5-hydroxymethylfurfural the latter is obtained by acid-catalyzed dehydration of D-frudose or frudosans (inulin) the latter, however, are too expensive as starting materials, and yields from glucose-based waste raw materials are no higher than 40%. Therefore, the potential attractive option of furan-2,5-dicarboxylic acid will develop only after an effident generation of 5-hydroxymethylfurfural from forestry waste materials has been developed. The same compound is also the starting material for the synthesis of other interesting chemicals obtained by oxidative processes, such as 5-hydroxymethylfuroic add, 5-formylfuran-2-carboxylic add and the 1,6-dialdehyde. 

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