Kromera,b,n a centre for microbial electrosynthesis cemes. Biocatalytic synthesis of adipic acid from glucose eliminates two environmental concerns characteristic of industrial adipic. Adipic acid is a chemical precursor used for the production of nylon, lubricants, coatings, plastics, and plasticizers. Muconic acid ma is a dicarboxylic acid that can be upgraded to produce highvalue commodity chemicals, including terepthalic acid, which in turn serves as a precursor for the production of polyester pet. Strains of escherichia coli were constructed and evaluated that synthesized cis,cis. Bioprocess development for muconic acid production from. Muconic acid ma is an unsaturated dicarboxylic acid precursor of terephthalic and adipic acid, which are monomers of the plastics polyethylene terephthalate pet and nylon 66 lu et al. Muconic acid ma is a promising bulk chemical due to its extensive industrial applications in the production of adipic acid and other valuable, biodegradable intermediates. Adipic acid is an industrially important dicarboxylic acid that is a precursor to nylon 6,6, among other polymers.
Innovative chemicals and materials from bacterial aromatic. Us4535059a muconic acid productivity by a stabilized mutant. Adipic acid is an important industrial chemical used in the synthesis of. All used chemicals ta, ammonium metavanadate, muconic acid, oxalic acid as well as zno and tio 2 were purchased from sigmaaldrich and applied without further treatment. To diversify the hydrogenation products derived from cis,transmuconic acid. Electrochemical conversion of muconic acid to biobased.
Muconic acid ma is a valuable compound for adipic acid production, which is a precursor for the synthesis of various polymers such as plastics, coatings, and nylons. The product is majorly used for producing adipic acid, which is widely used in synthesizing nylon. Tailoring strain construction strategies for muconic acid production in s. Synthesis of gallic acid and pyrogallol from glucose. After this process, the catechol is oxidatively ring opened to produce cis,cis muconate as the terminal metabolite draths and frost, 1994. Pdf production of diethyl terephthalate from biomass. The cis, cismuconic acid is thereafter hydrogenated to produc adipic acid as indicated by the label k in fig.
Ma is heretofore mainly produced from petrochemicals by organic reactions which are not environmentally friendly or renewable. The global muconic acid market report serves as a detailed market research guide for clients requiring latest industry figures and insights. Muconic acid market size was more than usd 37 million in 2016 and will witness 6. Enhancing muconic acid production from glucose and lignin. In this case, ccma was synthesized by converting the shikimate pathway intermediate dhs via. Today it is produced mainly in chemical processes from petrochemicals like benzene. It is likely to attain a cagr of more than 5% during the forecast period. Monoperphthalic acid 51jcs3398, 69jcsc2080, 89cc1629 and mchloroperbenzoic acid 80joc1153, 90jcsp12979 both give good yields of the anhydrides. Biocatalytic production of adipic acid from glucose using engineered. These components were mixed with enough water to allow room for addition of other. The determination of its concentration in urine is therefore used as a. Environmentally compatible synthesis of adipic acid from d. Nylon 66 accounts for about 85% of the total adipic acid demand. Txxhdpdfnkhhgwzpuqhviosan trans,transmuconic acid chemical.
Pdf cis,cismuconic acid is a polyunsaturated dicarboxylic acid that can be produced renewably. Benzenefree synthesis of adipic acid request pdf researchgate. A novel muconic acid biosynthesis approach by shunting. Muconic acid market will be primarily driven by textile. Bacterial cell tranformants for production of cis, cis. Here, we demonstrate the electrocatalytic conversion of cis,cismuconic acid, a fermentation product, to trans,transmuconic acid, trans3hexenedioic acid, and adipic acid used for the production of biobased polyamides and polyesters such as. It is produced during the degradation of chlorobenzene by bacteria like bacillus. An expanded enzyme toolbox for production of cis, cismuconic acid and other shikimate pathway derivatives in saccharomyces cerevisiae. Owing to the absence of cis,cis muconic acid solubility. Draths and frost first reported the constitution of an artificial pathway in escherichia coli leading to the production of muconic. A novel muconic acid biosynthesis approach by shunting tryptophan biosynthesis via anthranilate article pdf available in applied and environmental microbiology 79 april 20 with 193 reads. Overview of optimization strategies for the synthesis of aromatic compounds cis, cis muconic acid ccm and gallic acid ga in s. Muconic acid production from methane using rationally. Aug 26, 2015 regulating and ameliorating enzyme expression and activity greatly affects the performance of a given synthetic pathway.
In this study, a new synthetic pathway for cis, cis muconic acid ccma. Muconic acid productivity by a stabilized mutant microorganism population. Here, we demonstrate the electrocatalytic conversion of cis,cis muconic acid, a fermentation product, to trans,trans muconic acid, trans3hexenedioic acid, and adipic acid used for the production of biobased polyamides and polyesters such as. The process involves operating the bioconversion system under phosphatelimiting conditions so as to achieve an increase in specific muconic acid productivity with a stabilized population of microorganism such as an atcc no. In this study, we aim to explore the potential of the e. The v x o y tio 2 and v x o y zno catalysts synthesized by the impregnation method, which consisted of the adsorption of the ammonium metavanadate nh 4 vo 3, as precursor, from an aqueous solution on the supports tio.
Muconic acid cis,cis muconic acid ma is an unsaturated dicarboxylic acid with a molecular mass of 142. Cis, cismuconic acid ma is a dicarboxylic acid of recognized industrial value. United states pollution prevention and epa744r98001. Adipic acid is a highvalue compound used primarily as a precursor for the synthesis of nylon, coatings, and plastics. The analytical market research report muconic acid market global industry analysis, size, share, growth, trends and forecast, 2014 2020 is now available on transparency market researchs official site.
Us8426639b2 preparation of trans, trans muconic acid and trans. Muconic acid market driven by spiraling demand for adipic acid. Metabolic engineering of corynebacterium glutamicum for the. Request pdf bioprocess development for muconic acid production from aromatic compounds and lignin muconic acid ma is a biobased platform chemical that can be converted into the commodity. Currently, it is produced mainly by a twostage process which starts with the oxidation of benzenederived cyclohexane resulting in a cyclohexanolcyclohexanone mixture. Muconic acid cis,cismuconic acid ma is an unsaturated dicarboxylic acid with a molecular mass of 142. The present work concerns with an investigation on the solubility of cis,cismuconic acid dissolution in different polar solvents by characterizing and modeling the dissolution as a function of temperature.
Biosynthesis of cis,cismuconic acid and its aromatic. Electrochemical conversion of muconic acid to biobased diacid. Alternatively, cis,cismuconic acid microbially synthesized from glucose is isomerized and the resulting trans,transmuconic acid reacted in a cycloaddition with. Expanding the scope of biomassderived chemicals through. Composition of muconic acid production medium for the fermentation process.
Achieved highest titer of an aromaticbased molecule in yeast for a shakeflask condition. Nov 08, 2017 muconic acid market share is forecast to surpass usd 60 million by 2024. Jia wang, xiaolin shen, justin rey, qipeng yuan, yajun yan. Most studies reported to date have targeted conversion of pcaderived muconic acid to adipic and terephthalic acid lu et al. This invention further provides a procedure for constructing novel strains of microorganisms e. Muconic acid market share is forecast to surpass usd 60 million by 2024. However, the chemical conversion of ccma to adipic acid is expensive, environmentally damaging, and results in low yield 0. Isoprene and acrylic acid microbially synthesized from glucose undergo a cycloaddition to form 4methylcyclohex3ene1carboxylic acid. The synthetic pathway for muconic acid is depicted in the context of the shikimate pathway in yeast. Because of the strong environmental impact of the production processes and the dependence on fossil resources, biotechnological production processes would provide an interesting alternative. It provides direct access to adipic acid and terephthalic acid, prominent monomers of commercial plastics. A useful synthetic procedure is the peracid oxidation of 1,2benzoquinones 1 to the anhydrides 157 equation 20, which can be hydrolysed to muconic acid derivatives 48hca1210. Therefore, there is a need to discover alternative methods for the direct. Synthesis of adipic acid from biomassderived carbon sources download pdf.
This invention provides a process for bioconversion of an organic substrate e. Owing to the absence of cis,cismuconic acid solubility. The following gradient was used at a flow rate of 1 mlmin. Biological production processes provide a promising alternative for ma production. A nearly 24fold increase in muconic acid titer was achieved from the initial strain to nearly 141 mgl. Us4535059a muconic acid productivity by a stabilized. Pdf solubility of cis, cismuconic acid in various polar. Adipic acid is a chemical precursor used for the production. The cis,cismuconic acid which accumulates extracellularly is hydrogenated to afford adipic acid. Approximately 21 million kg of catechol are produced globally each year. Metabolic engineering of corynebacterium glutamicum for. Alternatively, cis,cis muconic acid microbially synthesized from glucose is isomerized and the resulting trans,trans muconic acid reacted in a cycloaddition with. 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. The recombinant yeast cells finally produced about 1.
Biobased adipic acid december 2012 global adipic acid ada demand is estimated at 2. In this study, several metabolic engineering strategies were used in an attempt to. Biological production processes provide a promising alternative for ma. Apr 01, 1997 the cis, cis muconic acid is thereafter hydrogenated to produc adipic acid as indicated by the label k in fig. The primary key driver behind the growth of the global muconic acid market is the massive demand for adipic acid. In this study, several metabolic engineering strategies were used in an. The present work concerns with an investigation on the solubility of cis,cis muconic acid dissolution in different polar solvents by characterizing and modeling the dissolution as a function of temperature. Quantification of anthranilate, catechol, and muconic acid was based on the peak areas at absorbance of specific wavelengths 329 nm for anthranilate, 274 nm for catechol, and 260 nm. Dec 21, 2018 muconic acid ma is a valuable compound for adipic acid production, which is a precursor for the synthesis of various polymers such as plastics, coatings, and nylons. Biosynthesis of cis, cismuconic acid and its aromatic precursors. Yet another example of the draths frost strategy for synthesizing industrial chemicals using biocatalysis and renewable feedstocks is their synthesis of catechol. Muconic acid production from glucose using enterobactin. An expanded enzyme toolbox for production of cis, cis muconic acid and other shikimate pathway derivatives in saccharomyces cerevisiae.
In the present work, we engineered the soil bacterium corynebacterium glutamicum into a stable genomebased cell factory for highlevel production of biobased ma from aromatics and lignin hydrolysates. Draths and frost first reported the constitution of an artificial pathway in. Muconic acid ma is an unsaturated, c6dicarboxylic acid that can be readily converted into the commercial commodity chemicals adipic acid and terephthalic acid. Tailoring strain construction strategies for muconic acid.
Us5487987a synthesis of adipic acid from biomassderived. Muconic acid is the synthetic precursor of adipic acid, and the latter is an important platform chemical that can be used for the production of nylon6,6 and polyurethane. Overview of optimization strategies for the synthesis of aromatic compounds cis, cismuconic acid ccm and gallic acid ga in s. Previously, draths and frost engineered a recombinant escherichia coli to produce muconic acid from glucose via a heterologous synthetic pathway drawing from a naturally occurring intermediate in the shikimate pathway, 3dehydroshikimate dhs draths and frost, 1994, niu et al. There is substantial interest in producing muconic acid from biomass, typically motivated by the ability to ef. Mar 24, 2015 the global muconic acid market will expand at a 7.
Towards bacterial strains overproducing ltryptophan and other aromatics by metabolic engineering. There are three isomeric forms designated trans,trans muconic acid, cis,trans muconic acid, and cis,cis muconic acid which differ by the geometry around the double bonds. Electrochemical hydrogenation of muconic acid iowa state. Amino acid derepression and systematic knockouts improved precursor availability. Recently, it has been shown that engineering microbial cocultures is an emerging and promising approach for biochemical production. Us4588688a process for the production of muconic acid. Thus, the recombinantly transformed host cells for use in accordance with the present invention are preferably characterized by the constitutive expression of structural genes encoding 3dehydroshikimate dehydratase.
Media in category muconic acid the following 12 files are in this category, out of 12 total. Metabolic engineering of escherichia coli for producing. Muconic acid market size industry share analysis report. Metabolic engineering of muconic acid production in. Regulating and ameliorating enzyme expression and activity greatly affects the performance of a given synthetic pathway. Extreme high moderate low section 1 chemical product and company identification product name trans,transmuconic acid statement of hazardous nature considered a hazardous substance according to osha 29 cfr 1910. Water, ethanol, 2propanol and acetic acid have been investigated as solvents in the range temperatures from a 298. Renewable unsaturated polyesters from muconic acid. Electrocatalysis is evolving as a competitive alternative to conventional heterogeneous catalysis for the conversion of platform chemicals from biomass. Metabolic engineering of a novel muconic acid biosynthesis. Free synthesis of adipic acid niu 2002 biotechnology. Jul 20, 2018 cis, cis muconic acid ma is a dicarboxylic acid of recognized industrial value. Highlights muconic acid was produced in saccharomyces cerevisiae for the first time.
329 668 342 158 17 212 1595 334 377 1043 871 1055 555 1567 1136 771 721 507 1317 1422 1584 1506 1035 684 485 1215 104 86 948 1033 208 1063 359 337