Maleic anhydride

Maleic anhydride[1]
Identifiers
CAS number 108-31-6 YesY
PubChem 7923
ChemSpider 7635 YesY
UNII V5877ZJZ25 YesY
EC-number 203-571-6
ChEBI CHEBI:474859 N
ChEMBL CHEMBL374159 YesY
RTECS number UE5950000
Jmol-3D images Image 1
Properties
Molecular formula C4H2O3
Molar mass 98.06 g/mol
Appearance White crystals
Density 1.48 g/cm3
Melting point

52.8 °C, 326 K, 127 °F

Boiling point

202 °C, 475 K, 396 °F

Solubility in water Reacts
Hazards
MSDS MSDS at J. T. Baker
EU classification Corrosive (C)
R-phrases R22, R34, R42/43
S-phrases (S2), S22, S26,
S36/37/39, S45
NFPA 704
NFPA 704.svg
1
3
1
Flash point 102 °C
Related compounds
Related acid anhydrides Succinic anhydride
Related compounds Maleic acid
 N anhydride (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Maleic anhydride (cis-butenedioic anhydride, toxilic anhydride, 2,5-dioxofuran) is an organic compound with the formula C2H2(CO)2O. 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 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:

2 CH3CH2CH2CH3 + 7 O2 → 2 C2H2(CO)2O + 8 H2O

Reactions

The 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 half-ester 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 cyclobutane tetracarboxylic dianhydride (CBTA). This compound is used in the production of polyimides and as an alignment film for liquid crystal displays.[2][3]

Maleic anhydride dimerization

References

  1. ^ Merck Index, 11th Edition, 5586.
  2. ^ Horie, T.; Sumino, M.; Tanaka, T.; Matsushita, Y.; Ichimura, T.; Yoshida, J. I. (2010). "Photodimerization of Maleic Anhydride in a Microreactor Without Clogging". Organic Process Research & Development 14 (2): 100128104701019. doi:10.1021/op900306z.  edit
  3. ^ Reaction conditions Horie et al 2010 reaction conditions: microreactor , mercury lamp, ethyl acetate solvent, 15 °C

External links


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Look at other dictionaries:

  • maleic anhydride — noun : a crystalline cyclic acid anhydride C4H2O3 that gives rise to maleic acid on reaction with water, that reacts readily with dienes in the Diels Alder reaction, and that is used chiefly in the manufacture of alkyd and other resins and in the …   Useful english dictionary

  • maleic anhydride — maleino rūgšties anhidridas statusas T sritis chemija formulė (O=)₂C₄H₂O atitikmenys: angl. maleic anhydride rus. малеиновый ангидрид ryšiai: sinonimas – 2,5 furandionas …   Chemijos terminų aiškinamasis žodynas

  • maleic anhydride — noun Date: 1857 a caustic crystalline cyclic anhydride C4H2O3 used especially in making resins …   New Collegiate Dictionary

  • maleic anhydride — Chem. a colorless crystalline, unsaturated compound, C4H2O3, that is soluble in acetone and hydrolyzes in water: used in the production of polyester resins, pesticides, and fumaric and tartaric acids. [1855 60] * * * …   Universalium

  • Styrene maleic anhydride — Chembox new Name = Styrene maleic anhydride ImageFile = ImageSize = 200px ImageName = Styrene Maleic Anhydride IUPACName = Poly(Styrene co Maleic Anhydride) OtherNames = SMA; Xiran® Section1 = Chembox Identifiers CASNo = 9011 13 6 Section2 =… …   Wikipedia

  • Anhydride maléique — Général Nom IUPAC anhydride cis butènedioïque Synonymes …   Wikipédia en Français

  • Maleic acid — Not to be confused with Malic acid or malonic acid. Maleic acid …   Wikipedia

  • maleic acid — /meuh lee ik/, Chem. a colorless, crystalline, water soluble solid, C4H4O4, isomeric with fumaric acid, having an astringent, repulsive taste and faint acidulous odor: used in the manufacture of synthetic resins, the dyeing and finishing of… …   Universalium

  • maleic acid — noun an unsaturated organic dicarboxylic acid, HOOCCH=CHCOOH, the geometric isomer of fumaric acid; it is found in unripe fruit, and is used industrially in the production of polyester resins See Also …   Wiktionary

  • maleic hydrazide — noun : a crystalline cyclic hydrazide C4H4N2O2 made by reaction of hydrazine with maleic acid or anhydride and used to retard plant growth and the sprouting of potatoes, onions, and root crops (as carrots or beets) in storage * * * /huy dreuh… …   Useful english dictionary

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