ChemicalBook > Product Catalog > Organic Chemistry > Carboxylic acids and derivatives > Acyclic carboxylic acid > Maleic acid
Maleic acid Chemical Properties
- Melting point:137-140 °C(lit.)
- Boiling point:275°C
- Density 1.59 g/mL at 25 °C(lit.)
- refractive index 1.5260 (estimate)
- Flash point:127 °C
- storage temp. Store at RT.
- solubility 478.8g/l
- pka1.83(at 25℃)
- form Powder/Solid
- color White
- Specific Gravity1.59
- PH1.3 (100g/l, H2O, 20℃)
- Water Solubility 790 g/L (25 ºC)
- Merck 14,5703
- BRN 605762
- Stability:Stable. Combustible. Incompatible with strong oxidizing agents, bases.
- CAS DataBase Reference110-16-7(CAS DataBase Reference)
- NIST Chemistry Reference2-Butenedioic acid (Z)-(110-16-7)
- EPA Substance Registry SystemMaleic acid (110-16-7)
Maleic acid Usage And Synthesis
- DescriptionMaleic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. Its chemical formula is HO2CCHCHCO2H. Maleic acid is the cis-isomer of butenedioic acid, where as fumaric acid is the trans-isomer. It is mainly used as a precursor to fumaric acid, and relative to its parent maleic anhydride, maleic acid has few applications.
- Chemical PropertiesMaleic acid, HOOCCH:CHCOOH, also known as maleinic acid and toxilic acid,is a colorless crystalline dibasic acid. It is soluble in water and alcohol. Maleic acid is used in manufacturing synthetic resins, in textile processing, and in preserving oils and fats.
- Chemical PropertiesMaleic acid is a white crystalline solid. Faint, acid like odor.
- Chemical PropertiesMaleic acid occurs as a white crystalline (monoclinic) powder and
possesses a faint acidulous odor and an astringent taste.
Fumaric acid and maleic acid are the simplest unsaturated carboxylic diacids. These acids experience two-step dissociation in aqueous solutions.They have the same structural formula but different spatial configurations. Fumaric acid is the trans and maleic acid the cis isomer. The physical properties of maleic acid and fumaric acid are very different. The cis isomer is less stable. Maleic acid is used in the preparation of fumaric acid by catalytic isomerization.
- Physical propertiesMaleic acid is a less stable molecule than fumaric acid. The difference in heat of combustion is 22.7 kJ·mol?1. The heat of combustion is -1355 kJ / mole. Maleic acid is more soluble in water than fumaric acid. The melting point of maleic acid (135 °C) is also much lower than that of fumaric acid (287 °C). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place in maleic acid at the expense of intermolecular interactions, and that are not possible in fumaric acid for geometric reasons.
- UsesMaleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis.
Maleic acid may be used to form acid addition salts with drugs to make them more stable, such as indacaterol maleate.
- Usesmanufacture of artificial resins; to retard rancidity of fats and oils in 1:10,000 (these are said to keep 3 times longer than those without the acid); dyeing and finishing wool, cotton, and silk; preparing the maleate salts of antihistamines and similar drugs.
- DefinitionChEBI: A butenedioic acid in which the double bond has cis- (Z)-configuration.
- Production MethodsMaleic anhydride is the main source of maleic acid produced by hydration. Maleic anhydride is prepared commercially by the oxidation of benzene or by the reaction of butane with oxygen in the presence of a vanadium catalyst.
- ReactionsAlthough not practised commercially, maleic acid can be converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation (ethanol / palladium on carbon). It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Maleic acid, being electrophilic, participates as a dienophile in many Diels - Alder reactions.
- Synthesis Reference(s)Journal of the American Chemical Society, 86, p. 4603, 1964 DOI: 10.1021/ja01075a017
The Journal of Organic Chemistry, 60, p. 6676, 1995 DOI: 10.1021/jo00126a013
Organic Syntheses, Coll. Vol. 2, p. 302, 1943
- General DescriptionMaleic acid is a colorless crystalline solid having a faint odor. Maleic acid is combustible though Maleic acid may take some effort to ignite. Maleic acid is soluble in water. Maleic acid is used to make other chemicals and for dyeing and finishing naturally occurring fibers.
- Air & Water ReactionsSoluble in water.
- Reactivity ProfileMaleic acid is a colorless to white crystalline solid. Moderately toxic. When heated to decomposition Maleic acid emits irritating fumes and acrid smoke [Lewis, 3rd ed., 1993, p. 790].
- HazardToxic by ingestion.
- Health HazardInhalation causes irritation of nose and throat. Contact with eyes or skin causes irritation.
- Fire HazardSpecial Hazards of Combustion Products: Irritating smoke containing maleic anhydride may form in fire.
- Pharmaceutical ApplicationsMaleic acid is used in the pharmaceutical industry as a pH modifier and a buffering agent.It is also used to prevent rancidity of oils and fats; a ratio of 1 : 10 000 is usually sufficient to retard rancidity. Maleic acid is commonly used as a pharmaceutical intermediate to form the maleate salts of several categories of therapeutic agents, such as salts of antihistamines and other drug substances.
- Safety ProfileModerately toxic by ingestion and skin contact. Passes through intact skin. A skin and severe eye irritant and a corrosive. Believed to be more toxic than its isomer, fumeric acid. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid smoke and irritating fumes.
- SafetyMaleic acid is generally regarded as a nontoxic and nonirritant
material when used at low levels as an excipient. Maleic acid is used
in oral, topical, and parenteral pharmaceutical formulations in
addition to food products.
LD50 (mouse, oral): 2.40g/kg(7)
LD50 (rabbit, skin): 1.56g/kg
LD50 (rat, oral): 0.708g/kg
- Potential ExposureMaleic acid is used to make artificial resins, antihistamines, and to preserve (retard rancidity) of fats and oils
- CarcinogenicityIn chronic feeding studies, 12 Osborne–Mendel rats per group were fed 0.5, 1.0, or 1.5% maleic acid in their diets for 2 years. Concentrations of 1.0 and 1.5% maleic acid retarded the growth rate of rats, and all concentrations of maleic acid increased mortality rate; no tumorigenesis was reported. Toxicological differences from controls were not marked, and the pathology was nonspecific.
- storageMaleic acid converts into the much higher-melting fumaric acid
(mp: 287°C) when heated to a temperature slightly above its melting
Maleic acid is combustible when exposed to heat or flame. The bulk material should be stored in airtight glass containers and protected from light. It is recommended not to store it above 25°C.
- ShippingUN2215 Maleic acid, Hazard class: 8; Labels: 8-Corrosive material.
- Purification MethodsCrystallise the acid from acetone/pet ether (b 60-80o) or hot water. Dry it at 100o. [Beilstein 2 H 748, 2 I 303, 2 II 641, 2 III 1911, 2 IV 2199.]
- IncompatibilitiesDust may form explosive mixture with air, Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, amines, reducing agents; alkali metals
- IncompatibilitiesMaleic acid can react with oxidizing materials. Aqueous solutions are corrosive to carbon steels.
- Waste DisposalDissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed. Liquid: incinerate after mixing with a flammable solvent. Use afterburner for complete combustion. Solid: dissolve in a flammable solvent or package in paper and burn. See above
- Regulatory StatusIncluded in the FDA Inactive Ingredients Database (IM and IV injections; oral tablets and capsules; topical applications). Included in nonparenteral and parenteral medicines licensed in the UK.
Maleic acid Preparation Products And Raw materials
- Preparation ProductsFumaric acidL-Aspartic acid Succinic acidD-Tartaric acidEnalaprilDL-Tartaric acidDimethyl fumarateMalathionIrsogladinecorrosion inhibitor PBTCA-typeDL-Aspartic acidCaptanPolymaleic acid2-Phosphonobutane-1,2,4-tricarboxylic acidMaleic acid-allyl alcohol copolymerAmlodipineFlupirtineDibutyl maleateChlorpheniramine maleate DL-Malic acidFUMARONITRILEsodium 1,1'-diphosphono propionyloxy phosphonate2-(Dimethylamino)-2-phenylbutyl 3,4,5-trimethoxybenzoate maleateMalic acid 5-BROMO-2-METHOXYCINNAMIC ACIDMercaptosuccinic acidDeltibant
- Raw materialsBenzeneMaleic anhydride 1,2-Dimethylbenzene
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