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Maleic anhydride information


Maleic anhydride[1]
Maleic anhydride
Maleic anhydride
Names
Preferred IUPAC name
Furan-2,5-dione[2]
Other names
Maleic anhydride[2]
cis-Butenedioic anhydride
2,5-Furanedione
Maleic acid anhydride
Toxilic anhydride
Identifiers
CAS Number
  • 108-31-6 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
106909
ChEBI
  • CHEBI:474859 checkY
ChEMBL
  • ChEMBL374159 checkY
ChemSpider
  • 7635 checkY
ECHA InfoCard 100.003.247 Edit this at Wikidata
EC Number
  • 203-571-6
Gmelin Reference
2728
PubChem CID
  • 7923
RTECS number
  • ON3675000
UNII
  • V5877ZJZ25 checkY
UN number 2215
CompTox Dashboard (EPA)
  • DTXSID7024166 Edit this at Wikidata
InChI
  • InChI=1S/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H checkY
    Key: FPYJFEHAWHCUMM-UHFFFAOYSA-N checkY
  • InChI=1/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H
    Key: FPYJFEHAWHCUMM-UHFFFAOYAP
SMILES
  • C1=CC(=O)OC1=O
Properties
Chemical formula
C4H2O3
Molar mass 98.057 g·mol−1
Appearance White crystals or needles[3]
Odor irritating, choking[3]
Density 1.48 g/cm3
Melting point 52.8 °C (127.0 °F; 325.9 K)
Boiling point 202 °C (396 °F; 475 K)
Solubility in water
Reacts
Vapor pressure 0.2 mmHg (20°C)[3]
Magnetic susceptibility (χ)
-35.8·10−6 cm3/mol
Hazards
GHS labelling:
Pictograms
GHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Signal word
Danger
Hazard statements
H302, H314, H317, H334, H372
Precautionary statements
P260, P261, P264, P270, P272, P280, P285, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P304+P341, P305+P351+P338, P310, P314, P321, P330, P333+P313, P342+P311, P363, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
1
1
Flash point 102 °C (216 °F; 375 K)
Explosive limits 1.4%-7.1%[3]
Lethal dose or concentration (LD, LC):
LD50 (median dose)
465 mg/kg (oral, mouse)
850 mg/kg (oral, rat)
875 mg/kg (oral, rabbit)
390 mg/kg (oral, guinea pig)
400 mg/kg (oral, rat)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 1 mg/m3 (0.25 ppm)[3]
REL (Recommended)
TWA 1 mg/m3 (0.25 ppm)[3]
IDLH (Immediate danger)
10 mg/m3[3]
Safety data sheet (SDS) MSDS at J. T. Baker
Related compounds
Related acid anhydrides
Succinic anhydride
Related compounds
Maleic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Maleic anhydride is an organic compound with the formula C2H2(CO)2O. It is the acid anhydride of maleic acid. It is a colorless or white solid with an acrid odor. It is produced industrially on a large scale for applications in coatings and polymers.[5]

  1. ^ Merck Index, 11th Edition, 5586.
  2. ^ a b "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 835. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  3. ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0376". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ "Maleic anhydride". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^ Kurt Lohbeck; Herbert Haferkorn; Werner Fuhrmann; Norbert Fedtke. "Maleic and Fumaric Acids". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_053. ISBN 978-3527306732.

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Maleic anhydride

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Maleic anhydride is an organic compound with the formula C2H2(CO)2O. It is the acid anhydride of maleic acid. It is a colorless or white solid with an...

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Styrene maleic anhydride

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Styrene maleic anhydride (SMA or SMAnh) is a synthetic polymer that is built-up of styrene and maleic anhydride monomers. The monomers can be almost perfectly...

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Maleic acid

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In industry, maleic acid is derived by hydrolysis of maleic anhydride, the latter being produced by oxidation of benzene or butane. Maleic acid is an industrial...

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Organic acid anhydride

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dianhydride. Maleic anhydride is a cyclic anhydride, widely used to make industrial coatings. ATP in its protonated form is an anhydride derived from...

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Phthalic anhydride

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About 10% of maleic anhydride is also produced: C6H4(CH3)2 + 7+1/2 O2 → C4H2O3 + 4 H2O + 4 CO2 Phthalic anhydride and maleic anhydride are recovered...

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Succinic anhydride

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thermally. Industrially, succinic anhydride is prepared by catalytic hydrogenation of maleic anhydride. Succinic anhydride hydrolyzes readily to give succinic...

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Citraconic acid

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displays the unusual property of spontaneously forming the anhydride, which, unlike maleic anhydride, is a liquid at room temperature. In the laboratory, citraconic...

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Alkenylsuccinic anhydrides

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alkenylsuccinic anhydrides are the preferred paper sizing agents, whereas in Europe, alkyl ketene dimers (AKDs) predominate. The reaction of maleic anhydride (MA)...

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Polyester resin

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by the reaction of dibasic organic acids and polyhydric alcohols. Maleic anhydride is a commonly used raw material with diacid functionality in unsaturated...

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SMA

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of magnitude Stone mastic asphalt, a type of road surface Styrene maleic anhydride, a synthetic polymer Submillimeter Array, radio telescopes in Mauna...

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Nadic anhydride

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Diels-Alder reaction, nadic anhydride was given as an example of the reaction, made by the condensation of maleic anhydride and cyclopentadiene, which...

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Malic acid

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296). Malic acid contains 10 kJ (2.39 kilocalories) of energy per gram. Racemic malic acid is produced industrially by the double hydration of maleic anhydride...

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Limonene

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the formation of Diels–Alder adducts between α-terpinene adducts and maleic anhydride. It is possible to effect reaction at one of the double bonds selectively...

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Reversible inhibition of sperm under guidance

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referred to as the synthetic polymer styrene maleic anhydride (SMA), is the development name of a male contraceptive injection developed at IIT Kharagpur...

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Copolymer

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copolymerization of styrene maleic anhydride copolymer, r1 = 0.097 and r2 = 0.001, so that most chains ending in styrene add a maleic anhydride unit, and almost...

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Fumaric acid

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catalytic isomerisation of maleic acid in aqueous solutions at low pH. It precipitates from the reaction solution. Maleic acid is accessible in large...

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Dibutyl maleate

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acid maleic acid. It is a colorless oily liquid, although impure samples can appear yellow. Dibutyl maleate can be prepared by the reaction of maleic acid...

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Frontier molecular orbital theory

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between maleic anhydride and cyclopentadiene, the endo-product is favored, a result best explained through FMO theory. The maleic anhydride is an electron-withdrawing...

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Tetrahydrophthalic anhydride

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solvents. Tetrahydrophthalic anhydride, the cis isomer, is prepared by the Diels-Alder reaction of butadiene and maleic anhydride. Arthur C. Cope; Elbert C...

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Superabsorbent polymer

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Cellulose‐ or starch‐acrylonitrile graft copolymers 3.   Cross‐linked maleic anhydride copolymers The largest use of SAPs is found in personal disposable...

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Surface chemistry of paper

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particles less than 1 µm in diameterr. Common binders are styrene maleic anhydride copolymer or styrene-acrylate copolymer. The surface chemical composition...

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Alkyl ketene dimer

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ASA is prepared by the ene reaction of unsaturated hydrocarbons with maleic anhydride. In 1901, Edgar Wedekind published the synthesis of alkyl ketene dimers...

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Succinic acid

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hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol. Succinate is also produced from butane via maleic anhydride. Global...

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Neighbouring group participation

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chemistry (e.g. the reaction of a diene such as 1,3-cyclohexadiene with maleic anhydride normally gives the endo isomer because of a secondary effect {overlap...

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Alkyd

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typically produced from dicarboxylic acids or anhydrides, such as phthalic anhydride or maleic anhydride, and polyols, such as trimethylolpropane, glycerine...

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