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| | 2-Methylsuccinic acid Basic information |
| | 2-Methylsuccinic acid Chemical Properties |
| Melting point | 110-115 °C (lit.) | | alpha | [α]D20 -1～+1° (c=5, C2H5OH) | | Boiling point | 164.01°C (rough estimate) | | density | 1.0951 (rough estimate) | | refractive index | 1.4240 (estimate) | | storage temp. | Sealed in dry,Room Temperature | | solubility | Chloroform (Slightly), DMSO (Sparingly), Methanol (Slightly) | | form | Solid | | pka | 4.13(at 25℃) | | color | White to Off-White | | PH | 3.62(1 mM solution);3.08(10 mM solution);2.57(100 mM solution) | | Water Solubility | Soluble in water. | | BRN | 1722946 | | Stability: | Stable. Combustible. Incompatible with bases, oxidizing agents, reducing agents. | | CAS DataBase Reference | 498-21-5(CAS DataBase Reference) | | NIST Chemistry Reference | Butanedioic acid, methyl-(498-21-5) | | EPA Substance Registry System | Butanedioic acid, 2-methyl- (498-21-5) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | TSCA | Yes | | HS Code | 29171900 |
| | 2-Methylsuccinic acid Usage And Synthesis |
| Description | Methylsuccinic acid is a normal metabolite found in human fluids and is an intermediate metabolite in the breakdown of fatty acids. Increased urinary levels of methylsuccinic acid (together with ethylmalonic acid) are the main biochemical measurable features in ethylmalonic encephalopathy. | | Chemical Properties | white to beige crystalline powder | | Uses | Methylsuccinic acid is used as a flux material and an important dyestuff intermediate. It is also used as an intermediate in medicine and pharmaceuticals. | | Preparation | A common method employed for the synthesis of alkanedioic acids involves the oxidation of lactone derivatives. However, in the case of y-butyrolactones, the oxidations have proven particularly challenging due to the stability of the five-membered lactones. A successful approach to this type of oxidative preparation involves the carboxylation of γ-butyrolactone using carbon monoxide and hydrogen fluoride-antimony(V) fluoride superacid containing an excess of antimony(V) fluoride to afford 2-methylsuccinic acid.
Synthesis of 2-Methylsuccinic Acid from y-Butyrolactone | | Definition | ChEBI: 2-methylbutanedioic acid is a dicarboxylic acid that is butanedioic acid substituted at position 2 by a methyl group. It is a conjugate acid of a methylsuccinate. | | General Description | White or yellowish crystals or beige powder. | | Air & Water Reactions | Water soluble. | | Reactivity Profile | Carboxylic acids, such as 2-Methylsuccinic acid, donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in 2-Methylsuccinic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions. | | Health Hazard | ACUTE/CHRONIC HAZARDS: 2-Methylsuccinic acid may be harmful by inhalation, ingestion or skin absorption. When heated to decomposition it emits toxic fumes of carbon monoxide and carbon dioxide. | | Fire Hazard | Flash point data for 2-Methylsuccinic acid are not available; however, 2-Methylsuccinic acid is probably combustible. | | Synthesis | It can be prepared by partial hydrogenation of itaconic acid over Raney nickel. Alternatively, hydrocyanation of ethyl crotonate affords an intermediate, which converts to 2-methylsuccinic acid after hydrolysis of the ester and nitrile substituents. | | Purification Methods | Crystallise the acid from water. [Beilstein 2 IV 1948.] |
| | 2-Methylsuccinic acid Preparation Products And Raw materials |
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