ChemicalBook > Product Catalog > Organic Chemistry > Carboxylic acids and derivatives > Carboxylic Acid Anhydrides > Maleic anhydride
Maleic anhydride Chemical Properties
- Melting point:51-56 °C(lit.)
- Boiling point:200 °C(lit.)
- Density 1.48
- vapor density 3.4 (vs air)
- vapor pressure 0.16 mm Hg ( 20 °C)
- refractive index 1.4688 (estimate)
- Flash point:218 °F
- storage temp. Store at RT.
- form powder
- color White
- PH0.8 (550g/l, H2O, 20℃)Hydrolysis
- explosive limit1.4-7.1%(V)
- Water Solubility 79 g/100 mL (25 ºC)
- Sensitive Moisture Sensitive
- Merck 14,5704
- BRN 106909
- Henry's Law Constant(atm?m3/mol): Not applicable - reacts with water
- Exposure limitsNIOSH REL: TWA 1 ppm (0.25 mg/m3), IDLH 10 ppm; OSHA PEL: TWA 0.25 ppm; ACGIH TLV: TWA 0.25 ppm with an intended change of 0.1 ppm.
- Stability:Stable. Combustible. Incompatible with water, strong oxidizing agents, alkali metals, strong bases, amines, most common metals, polymerization catalysts and accelerators.
- CAS DataBase Reference108-31-6(CAS DataBase Reference)
- NIST Chemistry Reference2,5-Furandione(108-31-6)
- EPA Substance Registry SystemMaleic anhydride (108-31-6)
- Hazard Codes C
- Risk Statements 22-34-42/43
- Safety Statements 22-26-36/37/39-45
- RIDADR UN 2215 8/PG 3
- WGK Germany 1
- RTECS ON3675000
- F 21
- Autoignition Temperature870 °F
- TSCA Yes
- HS Code 2917 14 00
- HazardClass 8
- PackingGroup III
- Hazardous Substances Data108-31-6(Hazardous Substances Data)
- ToxicityLD50 orally in Rabbit: 1090 mg/kg LD50 dermal Rabbit 2620 mg/kg
Maleic anhydride Usage And Synthesis
- DescriptionMaleic Anhydride (MAN) is an organic compound with the chemical formula C4H203. It is the acid anhydride of maleic acid and in its pure state it is a colourless or white solid with an acrid odour. Maleic anhydride is truly a remarkable molecule in that it possesses two types of chemical functionality making it uniquely useful in chemical synthesis and applications.
Maleic Anhydride is a multifunctional chemical intermediate with applications in several fields of chemical industry. Its major end use is as feedstock in the production of unsaturated polyester resins (UPR).
These resins are used both in glass-reinforced and in unreinforced applications. The UPR end uses includes a wide range of applications in construction, marine and automobile industries.
In addition, Maleic Anhydride can also be used as raw material in the production of 1,4-butanediol (BDO), gamma- butyrolactone and tetrahydrofuran (THF). It is important to highlight that BDO is one of the world's fastest growing chemicals in the last years.
- Chemical PropertiesMaleic anhydride is colorless needles, white lumps, or pellets. Irritating, choking odor.
- Physical propertiesWhite, hydroscopic crystals (usually shipped as briquettes). Odor threshold concentration is 0.32 ppm (quoted, Amoore and Hautala, 1983).
- UsesIn the manufacture of polyester resins, fumaric acid, agricultural pesticides, and alkyl resins
- UsesMaleic Anhydride is heterocyclic compound used in the manufacture of unsaturated polyester resins. Maleic Anhydride has a wide range of other applications; it is used in synthetic tensides, insecticides, herbicides and fungicides.
- UsesIn Diels-Alder syntheses (as a dienophile), manufacture of alkyd-type of resins, dye intermediates, pharmaceuticals, agricultural chemicals (maleic hydrazide, malathion), in copolymerization reactions.
- DefinitionChEBI: A cyclic dicarboxylic anhydride that is the cyclic anhydride of maleic acid.
- Definitionmaleic anhydride: A colourlesssolid, C4H2O3, m.p. 53°C, the anhydrideof cis-butenedioic acid (maleicacid). It is a cyclic compound with aring containing four carbon atomsand one oxygen atom, made by thecatalytic oxidation of benzene or itsderivatives at high temperatures. It isused mainly in the manufacture ofalkyd and polyester resins andcopolymers.
- Production MethodsMaleic anhydride was traditionally manufactured by the oxidation of benzene or other aromatic compounds. As of 2006, only a few smaller plants continue to use benzene; due to rising benzene prices, most maleic anhydride plants now use n-butane as a feedstock.
In both cases, benzene and butane are fed into a stream of hot air, and the mixture is passed through a catalyst bed at high temperature. The ratio of air to hydrocarbon is controlled to prevent the mixture from catching on fire. Vanadium pentoxide and molybdenum trioxide are the catalysts used for the benzene route, whereas vanadium and phosphorus oxides are used for the butane route.
2 CH3CH2CH2CH3 + 7 O2 → 2 C2H2(CO)2O + 8 H2O.
- PreparationTo a flask equipped with a Dean-Stark trap, condenser, and mechanical stirrer is added 116 gm (1.0 mole) of maleic acid and 120 ml of tetrachloroethane. The contents are heated, the water (18 ml, 1.0 mole) distilled off as the azeotrope, and the residue distilled under reduced pressure to afford 87.7 gm (89.5%) of the anhydride, b.p. 82-84°C (15 mm), m.p. 53°C. The residue remaining in the flask consists of about 10 gm of fumaric acid, m.p. 287°C.
Fumaric and maleic acids both give maleic anhydride on heating. Fumaric acid must first be heated to a higher temperature to effect its conversion to maleic acid prior to its dehydration.
- ReactionsThe chemistry of maleic anhydride is very rich, reflecting its ready availability and bifunctional reactivity. It hydrolyzes, producing maleic acid, cis-HOOC–CH=CH–COOH. With alcohols, the halfester is generated, e.g., cis-HOOC–CH=CH–COOCH3.
Maleic anhydride is a potent dienophile in Diels-Alder reactions. It is also a ligand for low-valent metal complexes, examples being Pt(PPh3)2(MA) and Fe(CO)4(MA).
Maleic anhydride dimerizes in a photochemical reaction to form cyclo butane tetra carboxylic dianhydride (CBTA). This compound is used in the production of polyimides and as an alignment film for liquid crystal displays.
- Synthesis Reference(s)The Journal of Organic Chemistry, 60, p. 6676, 1995 DOI: 10.1021/jo00126a013
- General DescriptionColorless crystalline needles, flakes, pellets, rods, briquettes, lumps or a fused mass. Melts at 113°F. Shipped both as a solid and in the molten state. Vapors, fumes and dusts strong irritate the eyes, skin and mucous membranes. Flash point 218°F. Autoignition temperature 890°F. Used to make paints and plastics and other chemicals.
- Air & Water ReactionsSoluble in water. Reacts slowly with water to form maleic acid and heat.
- Reactivity ProfileMaleic anhydride react vigorously on contact with oxidizing materials. Reacts exothermically with water or steam. Undergoes violent exothermic decomposition reactions, producing carbon dioxide, in the presence of strong bases (sodium hydroxide, potassium hydroxide, calcium hydroxide), alkali metals (lithium, sodium, potassium), aliphatic amines (dimethylamine, trimethylamine), aromatic amines (pyridine, quinoline) at temperatures above 150° C [Vogler, C. A. et al., J. Chem. Eng. Data, 1963, 8, p. 620]. A 0.1% solution of pyridine (or other tertiary amine) in Maleic anhydride at 185°C gives an exothermic decomposition with rapid evolution of gas [Chem Eng. News 42(8); 41 1964]. Maleic anhydride is known as an excellent dienophile in the Diels-Alder reaction to produce phthalate ester derivatives. These reactions can be extremely violent, as in the case of 1-methylsilacyclopentadiene [J. Organomet., Chem., 1979, 179, c19]. Maleic anhydride undergoes a potentially explosive exothermic Diels-Alder reaction with 1-methylsilacyclopenta-2,4-diene at 150C [Barton, T. J., J. Organomet. Chem., 1979, 179, C19], and is considered an excellent dieneophile for Diels-alder reactions [Felthouse, Timothy R. et al. "Maleic anhydride , Maleic Acid, and Fumaric Acid." Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. 2005].
- HazardIrritant to tissue. Dermal and respiratory sensitization. Questionable carcinogen.
- Health HazardInhalation causes coughing, sneezing, throat irritation. Skin contact causes irritation and redness. Vapors cause severe eye irritation; photophobia and double vision may occur.
- Fire HazardBehavior in Fire: When heated above 300°F in the presence of various materials may generate heat and carbon dioxide. Will explode if confined.
- Safety ProfilePoison by ingestion and intraperitoneal routes. Moderately toxic by skin contact. A corrosive irritant to eyes, skin, and mucous membranes. Can cause pulmonary edema. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. A pesticide. Combustible when exposed to heat or flame; can react vigorously on contact with oxidizing materials. Explosive in the form of vapor when exposed to heat or flame. Reacts with water or steam to produce heat. Violent reaction with bases (e.g., sodmm hydroxide, potassium hydroxide, calcium hydroxide), dkah metals (e.g., sodium, potassium), amines (e.g., dimethylamine, triethylamine), lithium, pyridine. To fight fire, use alcohol foam. Incompatible with cations. When heated to decomposition (above 150℃) it emits acrid smoke and irritating fumes. See also ANHYDRIDES.
- Potential ExposureMaleic anhydride is used in unsaturated polyester resins; Agricultural chemical, and lubricating additives; in the manufacture of unsaturated polyester resins; in the manufacture of fumaric acid; in alkyd resin manufacture; in the manufacture of pesticides e.g., malathion, maleic hydrazide, and captan).
- Environmental FateChemical/Physical. Reacts with water forming maleic acid (Bunton et al., 1963). Anticipated products from the reaction of maleic anhydride with ozone or OH radicals in the atmosphere are carbon monoxide, carbon dioxide, aldehydes, and esters (Cupitt, 1980).
- Solubility in organics(wt % at 25 °C):
Acetone (227), benzene (50), carbon tetrachloride (0.60), chloroform (52.5), ethyl acetate (112), ligroin (0.25), toluene (23.4), o-xylene (19.4) (Windholz et al., 1983). Soluble in alcohol and 1,4- dioxane (Hawley, 1981).
- ShippingUN2215 Maleic anhydride, Hazard class: 8; Labels: 8-Corrosive material.
Maleic Anhydride is commercialized and transported in the solid and molten forms. The molten Maleic Anhydride is transported at temperatures ranging from 60 to 80°C in well-insulated tank containers or road tankers provided with heating devices. In the solid form, it can be transported as pastilles, which are usually packed in polyethylene bags of 25 kg and transported either by rail tanker or by truck.
- Purification MethodsCrystallise it from *benzene, CHCl3, CH2Cl2 or CCl4. Sublime it under reduced pressure. [Skell et al. J Am Chem Soc 108 6300 1986, Beilstein 17 III/IV 5897, 17/11 V 55.]
- IncompatibilitiesReacts slowly with water (hydrolyzes) to form maleic acid, a medium-strong acid. Dust may form explosive mixture with air. Reacts with strong oxidizers, oil, water, alkali metals; strong acids; strong bases. Violent reaction with alkali metals and amines above 66C. Dangerous reaction with oxidizers, amines, alkali metals, and hydroxides. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic, and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur)
- Waste DisposalConsult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal. Controlled incineration: care must be taken that complete oxidation to nontoxic products occurs.
Maleic anhydride Preparation Products And Raw materials
- Raw materialsBenzeneXylene1-PentanolN-BUTANELiquefied petroleum ges
- Preparation ProductsDibutyl maleateemulsion waterproof agentDL-Malic acidDIALLYL MALEATEWater soluble epoxy resin4-MALEIMIDOBUTYRIC ACIDDispersing rosin latexFUMARONITRILEDi-(2-Ethylhexyl)4,5-EpoxytetrahydrophthalateSULFACHLOROPYRIDAZINEChryseneAcipimoxPR-I retanning agentmaleic acid-vinyl acetate copolymer3-HYDROXY-1-PHENYL-6-PYRIDAZONEPyridaphenthiontou-ming oilantistatic finish agent for synthetic fiberneutral size-ASADioctyl maleate maleic anhydride-benzylethylene sulfonated acid copolyerWater-soluble resinN-EthylmaleimideDioctyl(maleate)tin DL-Asparagine monohydrateDODECENYLSUCCINIC ANHYDRIDEPYRIDAZINE-3,6-DIOLdisodium 4-[2-[(1-oxoundec-10-enyl)amino]ethyl] 2-sulphonatosuccinateDibutyltin maleateSizing agent for paper makingDisodium succinate hexahydratesynthetic tanning agent DLT-14Carbic anhydrideEXO-3,6-EPOXY-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDEsynthetic tanning agent KS-1maleic anhydride-arcylic acid copolymerMethyl tetrahydrophthalic anhydrideTetrahydro-4,7-epoxyisobenzofuran-1,3-dione3-BENZOYLACRYLIC ACIDBismaleimide
- Maleic acid Maleic anhydride Phenylmaleic anhydride 2,3-DIPHENYLMALEIC ANHYDRIDE BROMOMALEIC ANHYDRIDE RUBRATOXIN B Citraconic anhydride CIS-ACONITIC ANHYDRIDE 2,3-Dimethylmaleic anhydride 3,4,5,6-Tetrahydrophthalic anhydride Dichloromaleic anhydride Succinic anhydride 3-SULFOLENE Diglycolic anhydride Chromium(VI) oxide Glutaric anhydride Fumaric acid MALICANHYDRIDE
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