Maleic Anhydride

Base Information

• Chemical Name: Maleic Anhydride
• CAS No.: 108-31-6
• Deprecated CAS: 184288-31-1,1190407-73-8,1229972-04-6,1380217-40-2,2254521-46-3,1229972-04-6,1380217-40-2
• Molecular Formula: C2H2(CO)2O
• Molecular Weight: 98.0581
• Hs Code.: 2917 14 00
• European Community (EC) Number: 203-571-6
• ICSC Number: 0799
• NSC Number: 137653,137652,137651,9568
• UN Number: 2215
• UNII: V5877ZJZ25
• DSSTox Substance ID: DTXSID7024166
• Nikkaji Number: J2.419H
• Wikipedia: Maleic_anhydride
• Wikidata: Q412377
• RXCUI: 1362876
• Metabolomics Workbench ID: 66989
• ChEMBL ID: CHEMBL374159
• Mol file: 108-31-6.mol

Synonyms:2,5 Furandiones;2,5-Furandiones;Anhydride, Maleic;Anhydrides, Maleic;Maleic Anhydride;Maleic Anhydrides

Chemical Property of Maleic Anhydride

Chemical Property:

• Appearance/Colour: white crystals
• Vapor Pressure: 0.16 mm Hg ( 20 °C)
• Melting Point: 52.8 °C, 326 K, 127 °F
• Refractive Index: 1.554
• Boiling Point: 202 °C, 475 K, 396 °F
• PKA: 0[at 20 ℃]
• Flash Point: 218°F
• PSA: 43.37000
• Density: 1.484 g/cm³
• LogP: -0.37400
• Storage Temp.: Store at RT.
• Sensitive.: Moisture Sensitive
• Water Solubility.: 79 g/100 mL (25 ºC)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 98.000393922
• Heavy Atom Count: 7
• Complexity: 129
• Transport DOT Label: Corrosive

Purity/Quality:

98% ^*data from raw suppliers

Maleic Anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 22-34-42/43
• Safety Statements: 22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Acid Anhydrides, Cyclic
• Canonical SMILES: C1=CC(=O)OC1=O
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes, skin and respiratory tract. Inhalation may cause asthma-like reactions.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. Repeated or prolonged inhalation may cause asthma.
• Description: Maleic 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.
• Physical properties: White, hydroscopic crystals (usually shipped as briquettes). Odor threshold concentration is 0.32 ppm (quoted, Amoore and Hautala, 1983).
• Uses: In the manufacture of polyester resins, fumaric acid, agricultural pesticides, and alkyl resins Maleic 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. In Diels-Alder syntheses (as a dienophile), manufacture of alkyd-type of resins, dye intermediates, pharmaceuticals, agricultural chemicals (maleic hydrazide, malathion), in copolymerization reactions.

Technology Process of Maleic Anhydride

There total 346 articles about Maleic Anhydride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 48.5%

isopropenylbenzene (98-83-9,6144-04-3,25014-31-7,42612-14-6) → maleic anhydride (108-31-6) + 2-phenylacrolein (4432-63-7) + benzaldehyde (100-52-7) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With air; Mo-Te oxide; at 440 ℃; Product distribution; different catalysts and reaction temperatures;

DOI:10.1246/cl.1999.657

Reference yield: 38.9%

toluene (108-88-3,15644-74-3,16713-13-6) → maleic anhydride (108-31-6) + benzaldehyde (100-52-7) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With vanadia; at 400 ℃; Air;

DOI:10.1134/S003602440813013X

Reference yield:

3-bromodihydro-2,5-furandione (5470-44-0) → maleic anhydride (108-31-6) + hydrogen bromide (10035-10-6,12258-64-9)

Guidance literature:

Destillation;

upstream raw materials:

tetrahydrofuran

2,5-dihydrofuran

furan

4-methyleneoxetan-2-one

Downstream raw materials:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

(1r,2R,3S,4r,5R,6S)-bicyclo<2.2.2>oct-2-ene-2,3,5,6-tetracarboxylic bisanhydride

maleic acid 2-pyridylmonoamide

2-(3,5-dimethyl-1H-pyrazol-1-yl)butanedioic acid

Refernces

• 1、 Cavani, Fabrizio,Centi, Gabriele,Trifiro, Ferruccio. "Structure Sensitivity of the Catalytic Oxidation of n-Butane to Maleic Anhydride". . p. 492 - 494. Retrieved 1985.
• 2、 Wenig, Robert W.,Schrader, Glenn L.. "In Situ FTIR Spectroscopy of 1-Butene and 1,3-Butadiene Selective Oxidation to Maleic Anhydride on V-P-O Catalysts". . p. 1911 - 1918. Retrieved 1987.
• 3、 Mori, Kenji,Miyamoto, Akira,Murakami, Yuichi. "Activity and Selectivity in Catalytic Reactions of Buta-1,3-diene and But-1-ene on Supported Vanadium Oxides". . p. 13 - 34. Retrieved 1986.
• 4、 Cherbuliez,E. et al.. "-". . p. 458 - 464. Retrieved 1960.
• 5、 Ai. "-". . p. 761,762-765. Retrieved 1971.
• 6、 Matsuura, Ikuya,Ishimura, Tomohiro,Kimura, Naomasa. "Preparation and characterization of vanadyl hydrogen phosphate hydrates; VO(HPO4)*1.5 H2O and VO(HPO4)*0.5 H2O". . p. 769 - 770. Retrieved 1995.
• 7、 Bergeret, G.,Broyer, J. P.,David, M.,Gallezot, P.,Volta, J. C.,Hecquet, G.. "X-Ray Study of a Vanadium-Phosphorus Mixed Oxide Catalyst for Selective Butane Oxidation to Maleic Anhydride". . p. 825 - 826. Retrieved 1986.
• 8、 Igarashi, Hiroshi,Tsuji, Katsuyuki,Okuhara, Toshio,Misono, Makoto. "Effects of Consecutive Oxidation on the Production of Maleic Anhydride in Butane Oxidation over Four Kinds of Well-Characterized Vanadyl Pyrophosphates". . p. 7065 - 7071. Retrieved 1993.
• 9、 Wachs, Israel E.,Jehng, Jih-Mirn,Deo, Goutam,Weckhuysen, Bert M.,Guliants,Benziger,Sundaresan. "Fundamental studies of butane oxidation over model-supported vanadium oxide catalysts: Molecular structure-reactivity relationships". . p. 75 - 88. Retrieved 1997.
• 10、 Li, Xiukai,Ho, Ben,Zhang, Yugen. "Selective aerobic oxidation of furfural to maleic anhydride with heterogeneous Mo-V-O catalysts". . p. 2976 - 2980. Retrieved 2016.