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Succinic acid

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Succinic acid Basic information
Succinic acid Chemical Properties
  • Melting point:185 °C
  • Boiling point:235 °C
  • Density 1.19 g/mL at 25 °C(lit.)
  • refractive index n20/D 1.4002(lit.)
  • Flash point:>230 °F
  • storage temp. Store at RT.
  • solubility Soluble in ethanol, ethyl ether, acetone and methanol. Insoluble in toluene, benzene, carbon disulfide, carbon tetrachloride and petroleum ether.
  • form Powder/Solid
  • pka4.16(at 25℃)
  • color White to off-white
  • PH2.7 (10g/l, H2O, 20℃)
  • Water Solubility 80 g/L (20 ºC)
  • Merck 14,8869
  • BRN 1754069
  • Stability:Stable. Substances to be avoided include strong bases, strong oxidizing agents. Combustible.
  • CAS DataBase Reference110-15-6(CAS DataBase Reference)
  • NIST Chemistry ReferenceButanedioic acid(110-15-6)
  • EPA Substance Registry SystemSuccinic acid (110-15-6)
Safety Information
Succinic acid Usage And Synthesis
  • DescriptionSuccinic acid (butanedioic acid) is a dicarboxylic acid. It is a common intermediate in the metabolic pathway of several anaerobic and facultative micro-organisms.
    Succinic acid is used as a dietary supplement for symptoms related to menopause such as hot flashes and irritability. It is used as a flavoring agent for food and beverages. It is used to manufacture polyurethanes, paints and coatings, adhesives, sealants, artificial leathers, cosmetics and personal care products, biodegradable plastics, nylons, industrial lubricants, phthalate-free plasticizers, and dyes & pigments. In the pharmaceutical industry, it is used in the preparation of active calcium succinate, as a starting material for active pharmaceutical ingredients (adipic acid, N-methyl pyrrolidinone, 2-pyrrolidinone, succinate salts, etc.), as an additive in drug formation, for medicines of sedative, antispasmer, antiplegm, antiphogistic, anrhoter, contraception and cancer curing, in the preparation of vitamin A and anti-Inflammatory, and as antidote for toxic substance.
  • References[1]
  • Chemical PropertiesSuccinic acid,C02H(CH2)2C02H, also known as butanedioic acid,butane diacid, and amber acid, is a colorless odorless prisms or white crystalline powder that melts at 185°C (364 of). Soluble in water and alcohol, it is used as a chemical intermediate, Succinic acid is used in lacquers,medicine,dyes,and as a taste modifier.
  • Usessuccinic acid is widely use as organic intermediates for the pharmaceutical, engineering plastics, resins etc.. For the synthesis of sedatives, contraceptives and cancer drugs in the pharmaceutical industry. In the chemical industry for the production of dyes, alkyd resin, glass fiber reinforced plastics, ion exchange resins and pesticides.
  • UsesSuccinic Acid is an acidulant that is commercially prepared by the hydrogenation of maleic or fumaric acid. it is a nonhygroscopic acid but is more soluble in 25°c water than fumaric and adipic acid. it has low acid strength and slow taste build-up; it is not a substitute for normal acidulants. it combines with proteins in modifying the plasticity of bread dough. it functions as an acidulant and flavor enhancer in relishes, beverages, and hot sausages.
  • DefinitionChEBI: An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.
  • DefinitionA crystalline carboxylic acid, HOOC(CH2)2COOH, that occurs in amber and certain plants. It forms during the fermentation of sugar (sucrose).
  • Biotechnological ProductionTraditionally, succinic acid is produced by petrochemical synthesis using the precursor maleic acid. However, there are some microorganisms that are able to produce succinic acid (e.g. Actinobacillus succinogenes, Anaerobiospirillum succiniciproducens and Mannheimia succiniciproducens). Maximum product concentrations of 106 g.L-1 with a yield of 1.25 mol of succinic acid per mole of glucose and a productivity of 1.36 g.L-1.h-1 have been achieved by growing A. succinogenes on glucose . A high productivity of 10.40 g.L-1.h-1 has been reached with A. succinogenes growing on a complex medium with glucose in a continuous process with an integrated membrane bioreactor-electrodialysis process. In this process, the product concentration has been 83 g.L-1 . Moreover, metabolic engineering methods were used to develop strains (e.g. C. glutamicum, E. coli, S. cervisiae and Y. lipolytica) with high productivity and titer as well as low byproduct formation. For example, growing C. glutamicum strain DldhA-pCRA717 on a defined medium with glucose, a high productivity of 11.80 g.L-1.h-1 with a yield of 1.37 mol of succinic acid per mole of glucose and a titer of 83 g.L-1 has been reported after 7 h. An extended cultivation resulted in a product concentration of 146 g.L-1 after 46 h.
  • General DescriptionWhite crystals or shiny white odorless crystalline powder. pH of 0.1 molar solution: 2.7. Very acid taste.
  • Air & Water ReactionsSlightly water soluble.
  • Reactivity ProfileSuccinic acid reacts exothermically to neutralize bases, both organic and inorganic. Can react with active metals to form gaseous hydrogen and a metal salt. Such reactions are slow in the dry, but systems may absorb water from the air to allow corrosion of iron, steel, and aluminum parts and containers. Reacts slowly with cyanide salts to generate gaseous hydrogen cyanide. Reacts with solutions of cyanides to cause the release of gaseous hydrogen cyanide. May generate flammable and/or toxic gases and heat with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. May react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Can be oxidized exothermically by strong oxidizing agents and reduced by strong reducing agents. May initiate polymerization reactions.
  • Fire HazardFlash point data for Succinic acid are not available. Succinic acid is probably combustible.
  • Biotechnological ApplicationsSuccinic acid and its derivatives are used as flavoring agents for food and beverages. This acid could be used as feedstock for dyes, insecticides, perfumes, lacquers, as well as in the manufacture of clothing, paint, links, and fibers (McKinlay et al. 2007). Succinic acid is widely used in medicine as an antistress, antihypoxic, and immunity-improving agent, in animal diets, and as a stimulator of plant growth. It is also a component of bio-based polymers such as nylons or polyesters (Kamzolova et al. 2012b). Succinate esters are precursors for the known petrochemical products such as 1,4-butanediol, tetrahydrofuran, c-butyrolactone, and various pyrrolidinone derivatives (Bechthold et al. 2008).
    Succinic acid production by Y. lipolytica was reported for the first time when it was grown on ethanol under aerobic conditions and nitrogen limitation. Succinic acid amount was 63.4 g/L as the major product of batch fermentation in this process. However, the disadvantage was low yield of succinic acid on ethanol (58 %), and a high cost of production (Kamzolova et al. 2009).
    Kamzolova et al. developed a novel process for the production of succinic acid. It includes the synthesis of a-ketoglutaric acid by a thiamine-auxotrophic strain Y. lipolytica VKMY-2412 from n-alkanes, and subsequent oxidation of the acid by hydrogen peroxide to succinic acid. The concentration of succinic acid and its yield were found to be 38.8 g/L and 82.45 % of n-alkane consumed, respectively (Kamzolova et al. 2012b).
    Succinic acid production was also studied by genetically modified strains using glucose and glycerol as substrates. Yuzbashev et al. constructed temperaturesensitive mutant strains with mutations in the succinate dehydrogenase encoding gene SDH1 by in vitro mutagenesis-based approach. Then, the mutants were used to optimize the composition of the media for selection of transformants with the deletion in the SDH2 gene. The defects of each succinate dehydrogenase subunit prevented the growth on glucose, but the mutant strains grew on glycerol and produced succinate in the presence of the buffering agent CaCO3. Subsequent selection of the strain with deleted SDH2 gene for increased viability was allowed to obtain a strain that is capable to accumulate succinate at the level of more than 450 g/L with buffering and more than 17 g/L without buffering. Therefore, a reduced succinate dehydrogenase activity can lead to an increased succinate production (Yuzbashev et al. 2010). Y. lipolytica is able to produce succinic acid at low pH values. High amounts of succinate can be achieved by genetic engineering (Otto et al. 2013).
  • Safety ProfileModerately toxic by subcutaneous route. A severe eye irritant. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
  • CarcinogenicityMonosodium succinate was given to groups of 50 male and 50 female Fischer 344 rats in drinking water at levels of 0%, 1%, or 2% for 2 years. No toxic lesion specifically caused by long-term administration of monosodium succinate was detected, and no dose-related increase was found in the incidence of tumors in any organ or tissue. The incidence of C-cell tumors of the thyroid gland of females that received 2% solution was apparently, but not significantly, higher than that in controls. Because C-cell tumors are commonly occurring spontaneous tumors in aging female rats of this strain and the incidence of C-cell tumors in the female control group was lower than that of historical controls for the testing laboratory, the authors concluded that this lesion was not treatment related.
  • Purification MethodsWash it with diethyl ether. Crystallise it from acetone, distilled water, or tert-butanol. Dry it under vacuum over P2O5 or conc H2SO4. Also purify it by conversion to the disodium salt which, after crystallisation from boiling water (charcoal), is treated with mineral acid to regenerate the succinic acid. The acid is then recrystallised and dried in a vacuum. [Beilstein 2 H 606, 2 IV 1908.]
Succinic acid Preparation Products And Raw materials
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