Propionic acid, production from

Zhang A, Yang S. Propionic acid production from glycerol by metabohcaUy engineered Propionibacte-rium acidipropionici. Process Biochem 2009 44 1346-51. 

Zhuge X, Liu L, Shin HD, Li J, Du G, Chen J. Improved propionic acid production from glycerol with metabolicaUy engineered Propionibacterium jensenii by integrating fed-batch culture with a pH-shift control strategy. BioresourTechnol 2014 152 519-25. 

Jin Z.Yang ST. Extractive fermentation for enhanced propionic acid production from lactose by Propionibacterium acidipropionici Biotechnol Prog 1998 14 457-65. 

An alternative method of propionic acid production from sugars by propionibacteria has been suggested (Tyree et al., 1991). In this process two cultures, Lactobacillus xylosus and P. shermanii, are used in a system of two consecutive reactor vessels. Lactate, formed by L. xylosus in a batch process with constant stirring, enters the second vessel with immobilized cells of P. shermanii, where propionate is synthesized. The system is characterized by a high total productivity for propionate. 

Lewis VP and Yang S-T (1992) A novel extractive fermentation process for propionic acid production from whey lactose. Biotechnol Progr 8 104-110 Lichstein HC (1955) The presence of bound biotin in purified preparation of oxaloacetic carboxylase. J Biol Chem 212 217-222... 

Liang Z-X, Li L, Li S, Cai Y-H, Yang S-T, Wang J-F (2012) Enhanced propionic acid production from Jerusalem artichoke hydrolysate by immobilized Propionibacterium acidipropionici in a fibrous-bed bioreactor. Bioprocess Biosyst Eng 35(6) 915-921. doi 10.1007/s00449-011-... 

Dishisha, T., Ibrahim, M.H.A., Cavero, V.H., Alvarez, M.T., Hatti-Kaul, R., 2015. Improved propionic acid production from glycerol combining cycHc batch- and sequential batch fermentations with optimal nutrient composition. Bioresource Technology 176,80-87. 

Dishisha, T, Stahl, A., Lundmark, S., Hatti-Kaul, R., 2013. An economical biorefinery process for propionic acid production from glycerol and potato juice using high cell density fermentation. Bioresource Technology 135,504—512. 

Subsequent insertion of CO into the newly formed alkyl-ruthenium moiety, C, to form Ru-acyl, D, is in agreement with our 13C tracer studies (e.g., Table III, eq. 3), while reductive elimination of propionyl iodide from D, accompanied by immediate hydrolysis of the acyl iodide (3,14) to propionic acid product, would complete the catalytic cycle and regenerate the original ruthenium carbonyl complex. 

The water-gas shift reaction is normally an unwanted side reaction of homogeneous catalysis when carbon monoxide is engaged as a substrate and if water is present as the medium or as a product. Both a pH-basic medium (formation of the nucleophilic [OH] ) and metals or metal complexes that deprotonate the water favor the shift reaction. For example, in the hydrocarboxylation process to make propionic acid directly from C2H4, CO, and H2O (eq. (14)), the formation of hydrogen via the water-gas shift reaction leads to (minor) hydrogenation and hydroformylation products (cf. Section 2.1.2.2). 

A membrane cell recycle reactor with continuous ethanol extraction by dibutyl phthalate increased the productivity fourfold with increased conversion of glucose from 45 to 91%.249 The ethanol was then removed from the dibutyl phthalate with water. It would be better to do this second step with a membrane. In another process, microencapsulated yeast converted glucose to ethanol, which was removed by an oleic acid phase containing a lipase that formed ethyl oleate.250 This could be used as biodiesel fuel. Continuous ultrafiltration has been used to separate the propionic acid produced from glycerol by a Propionibacterium.251 Whey proteins have been hydrolyzed enzymatically and continuously in an ultrafiltration reactor, with improved yields, productivity, and elimination of peptide coproducts.252 Continuous hydrolysis of a starch slurry has been carried out with a-amylase immobilized in a hollow fiber reactor.253 Oils have been hydrolyzed by a lipase immobilized on an aromatic polyamide ultrafiltration membrane with continuous separation of one product through the membrane to shift the equilibrium toward the desired products.254 Such a process could supplant the current energy-intensive industrial one that takes 3-24 h at 150-260X. Lipases have also been used to prepare esters. A lipase-surfactant complex in hexane was used to prepare a wax ester found in whale oil, by the esterification of 1 hexadecanol with palmitic acid in a membrane reactor.255 After 1 h, the yield was 96%. The current industrial process runs at 250°C for up to 20 h. 

The hydroxylation of aromatics serves as an example for a sussessfiiU industrial production of intermediates in a technical scale. BASF Ludwigshafen produces iso-merically pure (iJ)-2-(4-hydroxyphenoxy)-propionic acid (HPOPS) from (iJ)-2-phe-noxypropionic acid (POPS) in a 100 m fermenter for use as a herbicide intermediate (Eq. 4-19). 

Structurally uniform polymeric porphyrins are expected if terephthalaldehyde is reacted with pyrrole in boiling propionic acid. Polymers from this reaction have been described [53], The authors cleaned the product from polypyrrole and low molecular weight porphyrins by washing with methanol and chloroform, and introduced different metal ions by treatment with metal salts in an ethanol/water mixture. But the polymers which exhibited specific conductivities of 10 S cm (up to 10 S cm by doping with I2) were analyzed only by IR-spectra. 

The Laboratory of Dairy Technology Research of the Institut National de la Recherche (INRA) in Rennes, France, is investigating the application of these techniques for improved propionic acid production (Boyaval and Corre 1995). Colomban et al. (1993) demonstrated the production of propionic acid from whey permeate by P. acidipropionici at high cell density combined with sequential cell recycling and ultrafiltration. O Figure 3.3 is a diagram of the process employing a 5-m industrial pilot plant bioreactor. 

Woskow SA, Glatz BA (1991) Propionic acid production by a propionic acid tolerant strain of Propionibacterium acidipropionid in bateh and semicontinuous fermentetion. Appl Environ Microbiol 57 2821—2828 Wyman CE (1994) Ethanol from EgnoceUulosic biomass technology, economics, and opportunities. Bioresource Technol 50 3—16 Wyman CE (ed) (1996) Handbook on bioethanol production and utilization. Taylor and Francis, Washington, DC... 

Austin B, Goodfellow M (1979) Pseudomonas mesophilica, a new species of pink bacteria isolated from leaf surfaces, hit J Syst Bacteriol 29 373-378 Balamurugan K, Venkata Dasu V, Panda T (1999) Propionic acid production by whole cells of Propionibacteriumfreudenreichii. Bioprocess Eng 20(2) 109-116. doi 10.1007/PL00009039 Balandreau J, Viallard V, Coumoyer B, Coenye T, Laevens S, Vandamme P (2001) Burkholderia cepacia genomovar 111 is a common plant-associated bacterium. Appl Environ Microbiol 67 982-985... 

Only with propanal are very high conversions (99%) and selectivity (> 98 0) to MMA and MAA possible at this time. Although nearly 95% selective, the highest reported conversions with propionic acid or methyl propionate are only 30—40%. This results in large recycle streams and added production costs. The propanal route suffers from the added expense of the additional step required to oxidize methacrolein to methacrylic acid. 

The advent of a large international trade in methanol as a chemical feedstock has prompted additional purchase specifications, depending on the end user. Chlorides, which would be potential contaminants from seawater during ocean transport, are common downstream catalyst poisons likely to be excluded. Limitations on iron and sulfur can similarly be expected. Some users are sensitive to specific by-products for a variety of reasons. Eor example, alkaline compounds neutralize MTBE catalysts, and ethanol causes objectionable propionic acid formation in the carbonylation of methanol to acetic acid. Very high purity methanol is available from reagent vendors for small-scale electronic and pharmaceutical appHcations. 

The nitroparaffins have been utilized for many appHcations (114). Some of these uses have been discontinued because of economic and environmental considerations. For instance, significant quantities of 1-nitropropane once were used for the production of hydroxylammonium sulfate and propionic acid by hydrolysis. The need to dispose of an acid waste stream from this process made it uneconomical, so it was discontinued. 

---