Fumaric acid production by fermentation

Authors: Carol A Roa Engel Adrie J J Straathof Tiemen W Zijlmans Walter M van Gulik Luuk A M van der Wielen

Publish Date: 2008/01/24

Volume: 78, Issue: 3, Pages: 379-389

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Abstract

The potential of fumaric acid as a raw material in the polymer industry and the increment of cost of petroleumbased fumaric acid raises interest in fermentation processes for production of this compound from renewable resources Although the chemical process yields 112 w/w fumaric acid from maleic anhydride and the fermentation process yields only 85 w/w from glucose the latter raw material is three times cheaper Besides the fermentation fixes CO2 Production of fumaric acid by Rhizopus species and the involved metabolic pathways are reviewed Submerged fermentation systems coupled with product recovery techniques seem to have achieved economically attractive yields and productivities Future prospects for improvement of fumaric acid production include metabolic engineering approaches to achieve low pH fermentationsCurrently fumaric acid is produced chemically from maleic anhydride which in turn is produced from butane However as petroleum prices are rising rather quickly maleic anhydride as a petroleum derivative has increased in price as well Anonymous 2007 This situation has caused a renewed interest in the fumaric acid production by fermentation that was operational during the 1940s Goldberg et al 2006 but was discontinued and replaced by petrochemical processes The fermentation process is also interesting because it involves carbon dioxide fixation as will be discussed later Fungi are known for their organic acidproducing capability and have been used in fermentation processes for fumaric acid productionProduction by filamentous fungi of organic acids including fumaric acid has recently been reviewed Magnuson and Lasure 2004 Goldberg et al 2006 These reviews focused on the microorganisms with their associated metabolic pathways In contrast the current review focuses on development of fumaric acid production processes After summarizing fumaric acid properties applications and production metabolic pathways for fumaric acid production will be discussed only briefly before turning to fermentation performance of the most prominent fumaric acidproducing strains Furthermore different methods that have been studied to optimize fermentation processes will be mentioned and future prospects for process development will be discussedBecause of its structure a carbon–carbon double bond and two carboxylic acid groups fumaric acid has many potential industrial applications Fig 1 It can act as starting material for polymerization and esterification reactions wwwtheinnovationgroupcom/ChemProfiles/Fumaric20Acidhtm 10/06/07As raw material for polymerization especially in the production of unsaturated polyester resins maleic anhydride is currently preferred to fumaric acid because maleic anhydride 146–163 /kg Anonymous 2007 is cheaper than fumaric acid the latter historically being around 10 more expensive than maleic anhydride http//wwwchemweekcom/inc/articles/t/2007/04/04/04/022html However fumaric acid could be a better option for the polymer industry among other carboxylic acids or their derivatives because of its nontoxic nature In addition special properties like greater hardness in the polymer structure can be achieved when fumaric acid is used wwwtheinnovationgroupcom/ChemProfiles/Fumaric20Acidhtm 10/06/07 In addition to polymerization there are two potentially new applications for fumaric acid and both require a different grade of purity of it The first is as a medicine to treat psoriasis a skin condition Altmeyer et al 1994 Mrowietz et al 1998 Psoriatic individuals are unable to produce fumaric acid in their body which is not the case in normal individuals due to a certain biochemical defect that interferes with adequate fumaric acid production in the skin Therefore psoriatic individuals need to take orally fumaric acid in the form of fumaric acid monoethyl or dimethyl ester to treat their disease The second potential application of fumaric acid is as supplement in cattle feed Recent studies indicate that a large reduction in the methane emissions of cattle can be achieved up to 70 if this cattle receives fumaric acidbased additive as a supplement in their diet Mcginn et al 2004 This could greatly reduce the total emission of methane as farm animals are responsible for 14 of the methane emission caused by human activityFumaric acid together with the related succinic and malic acids has been identified as one of the top ten building block chemicals that can be produced from sugars via biological or chemical conversion Werpy and Petersen 2004 Compared to these other dicarboxylic acids fumaric acid has a low aqueous solubility 7 g/kg at 25°C 89 g/kg at 100°C Stephen 1965 and low pK a values 303 and 444 Lohbeck et al 1990 which are properties that can be exploited for product recoveryFumaric acid is currently produced by isomerization of maleic acid which is produced from maleic anhydride Maleic anhydride in turn is industrially produced by catalytic oxidation of suitable hydrocarbons in the gas phase Benzene used to be the predominant starting material but oxidation of nbutane or nbutane–nbutene mixtures has become more important in recent years Lohbeck et al 1990 The butane oxidation reaction equation to maleic anhydride is C4H10 + 35O2 → C4H2O3 + 4H2O

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