Tartaric Acid Production Research Articles

Toward Sustainable Utilization and Production of Tartaric Acid

AbstractGlobal efforts toward establishing a circular carbon economy have guided research interests towards exploring renewable technologies that can replace environmentally harmful fossil fuel‐based production routes. In this context, sugar‐based bio‐derived substrates have been identified as renewable molecules for future implementation in chemical industries. Tartaric acid, a special C4 bio‐compound with two hydroxyl and carboxylic groups in the structure, displays great potential for the food, polymer, and pharmaceutical industries due to its unique biological reactivity and performance‐enhancing properties. To this point, there has yet to be a comprehensive literature review and perspective on the applications and synthesis of tartaric acid. As such, we have conducted a detailed and thorough outlook and discussion in terms of biological activity, organic synthesis, catalysis, structural characterization and synthetic routes. Lastly, we provide a critical discussion on the applications and synthesis of tartaric acid to give our insights into developing sustainable chemical technologies for the future.

Impact of microorganisms on key processes of organic acid metabolism during the occurrence and disappearance of paocai pellicle.

In vegetable fermentation, pellicle is a common quality deterioration phenomenon. This study investigates the characteristics of glucose, organic acids, amino acids, and biogenic amines during the pellicle occurrence and disappearance of paocai. The results revealed a slight increase in pH of the fermentation system after pellicle occurred, and glucose was the main carbohydrate that microbial activity primary relied on. The microorganisms responsible for pellicle formation consumed organic acids in brine, but the lactic acid in paocai gradually increased and exceeded 25mg/g. The appearance of pellicle caused a decrease in total free amino acids from 200.390mg/100g to 172.079 when pellicle occurred, whereas its impact on biogenic amines was not apparent. Through Kyoto Encyclopedia of Genes and Genomes pathway enrichment of metagenomics sequencing data, screening, and sorting of the key enzymes involved in organic acid metabolism, it was observed that the composition and species of the key microorganisms capable of metabolizing organic acids were more abundant before the appearance of pellicle. When pellicle occurred, lactic acid may be metabolized by Lactobacillus plantarum; in contrast, Lactobacillus and Pichia were associated with citric acid metabolism, and Lactobacillus, Pichia, Saccharomycodes, and Kazachstania were linked to malic acid metabolism. Moreover, Prevotella, Kazachstania, Lactobacillus, Vibrio, and Siphonobacter were implicated in succinic acid metabolism. Additionally, the production of tartaric acid and oxalic acid in paocai and brine resulted from abiotic effects. This knowledge offers a theoretical basis for precise control of paocai fermentation process. PRACTICAL APPLICATION: Our study revealed the specific situation of the metabolites produced by the microorganisms during the pollution and recovery process of pellicle in paocai fermentation, especially the effect of pellicle on the key process of organic acid metabolism. These research results provided theoretical basis for precise control of paocai fermentation.

K+ selectivity modulation in non-aqueous CO2 electroreduction on lead catalysts: from oxalic to tartaric acid production

Modulating potassium ions and the proton concentration in the catholyte regulates the faradaic efficiency and selectivity of a Pb plate electrode in non-aqueous media, forming a C4 product from CO2 reduction.

Changes on physiochemical properties and volatile compounds of Chinese kombucha during fermentation

Kombucha is a traditional fermented beverage in China. In this study, six samples of kombucha from different regions of China were fermented, and the pH, total acidity, organic acid, carbohydrate and volatile flavor compounds at different fermentation time were determined. The results showed that the acidity of the samples increased as fermentation progressed, which was manifested as a decrease in pH and an increase in total acidity. During the fermentation period, the content of all organic acids showed an upward trend, and acetic acid was the most dominant organic acid in kombucha. The content of sucrose showed a downward trend, but remained stable in the middle and late stages. However, the contents of glucose and fructose were increasing throughout the fermentation. Twenty volatile compounds were identified by headspace solid-phase microextraction with gas chromatography-mass spectrometry (HS-SPME-GC-MS), among which the contents of 2-phenylethanol, 2,5-dimethylbenzaldehyde, acetic acid, ethyl acetate, ethyl hexanoate, ethyl 2-phenylacetate, and 2-phenylethyl acetate were greatly increased, and could be used as markers of the flavor quality of kombucha. Principal component analysis and correlation analysis showed that unique quality characteristics of kombucha were formed during the fermentation, and fructose and glucose were related to the production of tartaric acid, malic acid, acetic acid, and other volatile compounds. This study provides a theoretical reference for the quality evaluation of kombucha, and is expected to help in developing kombucha products with high quality.

Catalytic Synthesis of Tartaric Acid from Glucose and Gluconic Acid over AuPt/TiO2 Catalysts: Studies on Catalyst Structure–Performance Dependency

Replacing fossil-derived tartaric acid (TA) with sugar-based TA provides a greener route for synthesizing bioplasticizers. However, the detailed mechanism involving C–H and C–C activation of sugar substrates in this area is still under debate. In this work, the plausible reaction mechanism for activation of −CHO (oxidation) and −COOH (decarboxylation) groups in glucose and gluconic acid molecules in the presence of bimetallic AuPt/TiO2 catalysts has been studied and revealed using the UV–vis technique. It is found that Pt and Au phases in bimetallic catalysts selectively promote C–H and C–C cleavage reactions through σ extraction (n−π*) and a π–π (π–π*) coordination mechanism, respectively. The Au2Pt2/TiO2 (Au/Pt: 1/1 atomic ratio) catalyst displays remarkable activity for primary conversion of glucose to gluconic acid (TOF ∼ 20,260 h–1 at 110 °C). Meanwhile, consecutive conversion of gluconic acid to TA can be selectively accelerated by the Au1Pt2/TiO2 (TOF: 3,159 h–1) catalyst. Thus, a record high TA production rate of 12.3 mol/h/molmetal was achieved in this work. Process design and the purification of product mixtures to obtain high quality TA were also proposed and validated at the laboratory scale. The outcome in this work will provide insights for aqueous phase oxidation for synthesis of various valuable sugar-derived carboxylic acids.

POSSIBILITY AND NECESSITY OF TARTARIC ACID PRODUCTION IN THE REPUBLIC OF MOLDOVA

The wine industry has been and remains a source of natural- tartaric acid. The tartaric acid can be obtained from such wastes as grape marcs, yeast, vinasse and wine stone. But the use of these wastes was limited in the Republic of Moldova by the production of tartaric acid lime (calcium tartrate) and wine stone, which were shipped to Ukraine and Armenia where the finished product is obtained. Currently, tartaric acid is used in considerable quantities in the winemaking and food industry, being a quite expensive imported product. The Department of Oenology and Chemistry has developed a complete technological scheme for the use of wine wastes to obtain the finished product – tartaric acid. The realization of the proposed tartaric acid production in the Republic of Moldova is important for the country’s economy and it does not require large investments. Wineries can also help to organize tartaric acid production by providing calcium tartrate, wine stone, pressed or dried yeast, and other ingredients.

Comparative study on tartaric acid production by two-chamber and three-chamber electro-electrodialysis

Acidification is an essential step in organic acid production. In this work, an environmentally friendly electro-electrodialysis (EED) process was carried out to transform potassium tartrate (K2Tar) to tartaric acid (H2Tar) without additional waste salt generation. The characteristics of ions migration in the two-chamber EED and three-chamber EED processes were investigated, and the conversion ratio of tartaric acid and specific energy consumption of the two configurations were also compared. The competitive migration of K+ ions and H+ ions through cation exchange membrane was the key factor affecting the extent of acidification in the two-chamber EED process, while the selective transport of tartrate ions (Tar2−) and H+ ions through the anion exchange membrane influenced the three-chamber EED process significantly. The three-chamber process generated pure H2Tar solution with higher concentration than the two-chamber process and reached a conversion ratio of 99% after 120 min’s operation running at 7 mA/cm2. Owing to the lower resistance of the two-chamber membrane stack, the specific energy consumption in the two-chamber EED process was lower than that of three-chamber EED process. This work provides important knowledge for assessing the application of EED in the production of tartaric acid (H2Tar) from potassium tartrate (K2Tar) and a better understanding of the transport phenomena in the system with ionic organic compounds.

Sustainable Electrochemical Production of Tartaric Acid

Herein, we describe a study of the electrochemical reduction of oxalic and glyoxylic acids toward a feasible green and sustainable production of tartaric acid in aqueous and/or acetonitrile solvent using silver and lead electrodes. Our results show that on the silver electrode, for both oxalic acid and glyoxylic acid, the reduction reaction is more favorable toward the dimerization step, leading to tartaric acid, due to the increase in the local pH, while on the lead electrode, the step involving the protonation of the intermediate is more favorable, leading to the formation of glycolate. Techno-economic analysis shows that tartaric acid production from glyoxylic acid and from oxalic acid via electrochemical synthesis can be a potential process at the industrial scale. In the present case, the oxygen evolution reaction was chosen as the reaction at the other electrode for practical reasons, but oxygen is a low-value product. Another anodic reaction with a more valuable oxidation product can be selected to increase the profitability of the overall electrochemical process and thereby decrease the total production costs of tartaric acid.

Enantiomeric Tartaric Acid Production Using cis-Epoxysuccinate Hydrolase: History and Perspectives.

Tartaric acid is an important chiral chemical building block with broad industrial and scientific applications. The enantioselective synthesis of l(+)- and d(−)-tartaric acids has been successfully achieved using bacteria presenting cis-epoxysuccinate hydrolase (CESH) activity, while the catalytic mechanisms of CESHs were not elucidated clearly until very recently. As biocatalysts, CESHs are unique epoxide hydrolases because their substrate is a small, mirror-symmetric, highly hydrophilic molecule, and their products show very high enantiomeric purity with nearly 100% enantiomeric excess. In this paper, we review over forty years of the history, process and mechanism studies of CESHs as well as our perspective on the future research and applications of CESH in enantiomeric tartaric acid production.

Isolation of the stable strain Labrys sp. BK-8 for l(+)-tartaric acid production

A novel cis-epoxysuccinate hydrolase (CESH) producing strain of Labrys sp. BK-8 for production of L(+)-tartaric acid was isolated and identified. After optimization, a maximum activity of 3597 ± 151 U/g was achieved in batch culture in a 10 L fermentor. When Labrys sp. BK-8 was immobilized on κ-carrageenan, the immobilized cells showed a high conversion rate (>99%), enantioselectivity (EE > 99.5%) and storage stability (>90 d). A conversion rate of 97% was still achieved after 10 repeat batches. The CESH was stable over a broad range of temperatures (up to 45°C) and pH values (4.0-10.0). The Labrys sp. BK-8 isolate provides a new alternative with good stability for the industrial biosynthesis of L(+)-tartaric acid.

Efficiency and Stability Enhancement of Cis-epoxysuccinic Acid Hydrolase by Fusion with a Carbohydrate Binding Module and Immobilization onto Cellulose

Cis-epoxysuccinic acid hydrolase (CESH) is an enzyme that catalyzes cis-epoxysuccinic acid to produce enantiomeric L(+)-tartaric acid. The production of tartaric acid by using CESH would be valuable in the chemical industry because of its high yield and selectivity, but the low stability of CESH hampers its application. To improve the stability of CESH, we fused five different carbohydrate-binding modules (CBMs) to CESH and immobilized the chimeric enzymes on cellulose. The effects of the fusion and immobilization on the activity, kinetics, and stability of CESH were compared. Activity measurements demonstrated that the fusion with CBMs and the immobilization on cellulose increased the pH and temperature adaptability of CESH. The chimeric enzymes showed significantly different enzyme kinetics parameters, among which the immobilized CBM30-CESH exhibited twofold catalytic efficiency compared with the native CESH. The half-life measurements indicated that the stability of the enzyme in its free form was slightly increased by the fusion with CBMs, whereas the immobilization on cellulose significantly increased the stability of the enzyme. The immobilized CBM30-CESH showed the longest half-life, which is more than five times the free native CESH half-life at 30 °C. Therefore, most CBMs can improve enzymatic properties, and CBM30 is the best fusion partner for CESH to improve both its enzymatic efficiency and its stability.

Ion conductive spacers for the energy-saving production of the tartaric acid in bipolar membrane electrodialysis

One of the common problems for the production of organic acid using electrodialysis technology is the relative high energy consumption due to their weak dissociated ability. Enlightened by our previous work [Journal of Membrane Science 341 (2009) 246–251 and Journal of Membrane Science 366 (2011) 266–271] in which the ion exchange resin were filled in the product compartments, a conducting spacer instead of the traditional non-conducting spacer was adopted for the convenience of the operation to facilitate ion transportation during the production process of the tartaric acid by the bipolar membrane electrodialysis technology. Herein, the cell voltage, the current efficiency and the energy consumption were investigated and compared before and after the use of the conductive spacers, respectively. Furthermore, the process economics were all evaluated and compared with the traditional methods. The experimental results showed that the conductive spacer can effectively facilitate the transport of the hydrogen ions in the product compartment and then effectively decrease the energy consumption of the tartaric acid production by the process. But, on the other hand, the simultaneous effects resulting from the hydrogen ion short circuit, including the reduced producing rate and current efficiency, also took place.

Tartaric acid production by ion exchange resin-filling electrometathesis and its process economics

The technical feasibility of applying the bipolar membrane electrodialysis (BMED) to the production of the organic acid has been confirmed. However, some unsolved problems for BMED at present, such as high cost, instable properties and limited varieties for the bipolar membranes and even the poor permselectivity of the associated mono-polar membranes, make the explorations on other electrodialysis technologies for the production of the organic acid necessary. In this work, a resin-filling electrometathesis technology (EMT) is attempted to produce tartaric acid based on our previous work [Journal of Membrane Science 341 (2009) 246–251]. Similarly, the cell voltage, current efficiency and energy consumption are investigated and compared during the tartaric acid production by EMT before and after the filling of resin, respectively. The relevant experimental phenomena and potential mechanism are analyzed tentatively. Furthermore, the process economics, including the EMT and BMED before and after the filling of the acid resins, are all evaluated and compared. The preliminary results show that the modified EMT used for the tartaric production can be carried out at relatively higher current density with relatively lower energy consumption which effectively reduces the cost of operation and investment on the plant compared with the other technologies.

Immobilization of Escherichia coli cells with cis-epoxysuccinate hydrolase activity for d(−)-tartaric acid production

Immobilization of cis-epoxysuccinate hydrolase-containing E. coli for D(-)-tartaric acid production was screened by various methods. The highest recovery of activity was obtained by entrapment in kappa-carrageenan gel. 23.6 g biomass/l and 43.4 g kappa-carrageenan/l were the best immobilization conditions optimized by response surface methodology with 83% yield (114 U/g). Cell autolysis was observed after immobilization. Immobilized cells showed high pH (5-10) stability, thermal (up to 65 degrees C) stability, conversion rate (>99.5%), enantioselectivity (ee > 99.6%), and were less affected by metal ions and surfactants compared with free cells. Conversion rate for immobilized cells preserved 93% after 10 repeated batches (5% for free cells).

The energy-saving production of tartaric acid using ion exchange resin-filling bipolar membrane electrodialysis

In view of some inherent disadvantages of traditional technique, production of tartaric acid was attempted through the laboratory-scale bipolar membrane electrodialysis (BMED) in this work. Due to the relatively low solubility of bitartrate, the three-compartment configuration but not the two-compartment configuration which is preferred for weak acid production was selected. Thus, one of the aims of this work lies in the exploration of the energy-saving producing method for weak acid by BMED with the three-compartment configuration. Enlightened by electro-deionization technology, strong acid resin was filled in the acid compartment which is partly responsible for high energy consumption in the weak acid production to facilitate the transport of ions. Accordingly, the cell voltage, current efficiency and energy consumption were investigated and compared during the tartaric acid production before and after the addition of resin, respectively. The preliminary results showed that the expectation that the run of BMED with three-compartment configuration at relatively high current density with relatively low energy consumption can be implemented to a certain extent by the aforementioned method.

Optimization of temperature and initial pH and kinetic analysis of tartaric acid production by Gluconobacter suboxydans

Response surface methodology was applied for the simultaneous optimization of initial pH and temperature of fermentation for the production of tartaric acid by Gluconobacter suboxydans. A temperature of 32.8 °C and an initial pH of 6.05 was found to be most suitable. Kinetic analysis for the growth of Gluconobacter suboxydans and product formation was done and a logistic model was used to describe the growth of Gluconobacter suboxydans while the Leudeking–Piret model explained the product formation. Parameters of the model were evaluated and tartaric acid formation was found to be non-growth associated.

Optimization of temperature and initial pH and kinetic analysis of tartaric acid production by

Optimization of temperature and initial pH and kinetic analysis of tartaric acid production by

Optimization of medium composition by response surface methodology for the production of tartaric acid by Gluconobacter suboxydans

The combined effect of sorbitol and yeast extract of the medium on tartaric acid production by Gluconobacter suboxydans, NCIM 2049, was studied in batch fermentation while keeping the temperature (30 °C) and pH (6.2) constant. Response surface methodology was used to obtain quadratic models for the production of tartaric acid. The multiple coefficients of regression between 0.8945 and 0.9820 was obtained during the process. The optimum medium composition comprising 20 kg/m3 sorbitol and 2 kg/m3 yeast extract was verified experimentally by observing the variation of cell mass and tartaric acid production with time.

Production of Tartaric Acid From Pomace of Some Anatolian Grape Cultivars

Production of tartaric acid from pomace of some Anatolian grape cultivators was investigated. Two different extraction methods based on either hot water or dilute acid were used. Based on the chemical analysis the amounts of CaCO₃ and CaCl₂ to be added into the extract were calculated and, the tartaric acid salts were precipitated as calcium tartrate. Calcium tartrate was first converted into tartaric acid by sulfuric acid treatment then, the tartaric acid was decolorized by means of active carbon and finally, crystallized under vacuum at 70°C. It was found that the calcium tartrate contents using dilute acid extraction were 1.3%, 1.7%, and 2.0% whereas in hot water extraction they were 2.1%, 2.5%, and 3.1% from Emir, Okuzgozu, and Bogazkere pomaces respectively. Tartaric acid contents corresponding to these calcium tartrates were 43.9%, 43.8%, and 44.1% from Emir, Okuzgozu, and Bogazkere grape pomaces, respectively. Tartaric acid amounts recovered from Emir, Okuzgozu, and Bogazkere grape pomaces processed with dilute acid extraction were 0.4%, 0.5%, and 0.6% and from hot water extraction were 0.6%, 0.8%, and 1.1%, respectively. Of two extraction methods hot water extraction was more efficient.

Optimization of medium composition by response surface methodology for the production of tartaric acid by

Optimization of medium composition by response surface methodology for the production of tartaric acid by