Basic information
- Standard SMILES
O=C1C=CC(=O)O1- InChIKey
FPYJFEHAWHCUMM-UHFFFAOYSA-N- Molecular formula
- C4H2O3
- Average molar mass
- 98.06 g/mol
- Monoisotopic mass
- 98.00039392
Names & identifiers
- Preferred name
- Maleic Anhydride
- IUPAC
- furan-2,5-dione
- English name
- Maleic anhydride
- Molecular formula
- C4H2O3
- Molecular weight
- 98.06
Names & synonyms
Show more names
Database identifiers
- CAS
108-31-6、184288-31-1- PubChem CID
- 7923
- DTXSID
DTXSID7024166- ChEMBL
CHEMBL374159- ChEBI
CHEBI:474859- UNII
- V5877ZJZ25
- EC Number
- 203-571-6、606-024-3
- Nikkaji
- J2.419H
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 129
Physicochemical properties
- Melting point
- 51 · 51-56 °C (lit.)
- Boiling point
- 200 °C · 200 °C (lit.)
- Density
- 1.48 · 1.48
- bulk density
- 700 · 700-800kg/m3
- vapor density
- 3.4 · 3.4 (vs air)
- vapor pressure
- 0.16 mm · 0.16 mm Hg ( 20 °C)
- refractive index
- 1.4688 · 1.4688 (estimate)
- Flash point
- 218 °F · 218 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- pka
- 0 · 0[at 20 ℃]
- form
- powder
- color
- White
- PH
- 0.8 · 0.8 (550g/l, H2O, 20℃)Hydrolysis
- Odor
- Mild acrid odor.
- explosive limit
- 1.4 · 1.4-7.1%(V)
- Water Solubility
- 79 g/100 · 79 g/100 mL (25 ºC)
- Sensitive
- Moisture Sensitive
- Merck
- 14 · 14,5704
- BRN
- 106909 · 106909
- Henry's Law Constant
- (atmm3/mol): Not applicable - reacts with water
- Exposure limits
- 0.01 mg/m3 · ACGIH:TLV-TWA 0.01 mg/m3 (0.0025 ppm),Inhalable fraction and vapor Dermal Sensitizer (DSEN) and Respiratory Sensitizer (RSEN) A4 — Not Classifiable as a Human CarcinogenOSHA:PEL-TWA 0.25 ppm (1 mg/m3)NIOSH:REL-TWA 1 mg/m3
- Dielectric constant
- 51 · 51.0(60℃)
- Stability
- Stable. Combustible. Incompatible with water, strong oxidizing agents, alkali metals, strong bases, amines, most common metals, polymerization catalysts and accelerators.
- Cosmetics Ingredients Functions
- FILM FORMING
- InChI
- 1S/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H
- InChIKey
- FPYJFEHAWHCUMM-UHFFFAOYSA-N
- SMILES
- O=C1OC(=O)C=C1
- LogP
- -2.61 at · -2.61 at 20℃
- Indirect Additives used in Food Contact Substances
- MALEIC ANHYDRIDE
- FDA 21 CFR
- 175.105 · 175.105; 175.300; 176.170;176.180; 177.1520; 177.1630;177.1680; 177.1820; 178.3870
- CAS DataBase Reference
- 108 · 108-31-6(CAS DataBase Reference)
- EWG's Food Scores
- 4 · 4-5
- FDA UNII
- 5877 ZJZ25 · V5877ZJZ25
- NIST Chemistry Reference
- 2 · 2,5-Furandione(108-31-6)
- EPA Substance Registry System
- Maleic anhydride (108-31-6)
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 23 · NA.23
- Symbol(GHS)
- 5 · GHS05,GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 302 · H302-H313-H314-H370-H372-H373-H317-H334-H402
- Precautionary statements
- 501 · P501-P273-P272-P260-P270-P264-P280-P284-P342+P311-P308+P311-P362+P364-P303+P361+P353-P333+P313-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405
- target organs
- Respiratory system
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- C
- Risk Statements
- 22 · 22-34-42/43
- Safety Statements
- 22 · 22-26-36/37/39-45
- OEB
- C
- OEL
- 1 mg/m3 · TWA: 1 mg/m3 (0.25 ppm)
- RIDADR
- 2215 · UN 2215 8/PG III (MALEIC ANHYDRIDE)
- WGK Germany
- 1 · 1
- RTECS
- 3675000 · ON3675000
- F
- 21 · 21
- Autoignition Temperature
- 870 °F · 870 °F
- TSCA
- TSCA listed
- HS Code
- 2917 · 2917 14 00
- HazardClass
- 8 · 8
- PackingGroup
- III
- Storage Class
- 6.1 D · 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Dam. 1Resp. Sens. 1Skin Corr. 1BSkin Sens. 1ASTOT RE 1 Inhalation
- Hazardous Substances Data
- 108 · 108-31-6(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in Rabbit: 1090 mg/kg LD50 dermal Rabbit 2620 mg/kg
- IDLA
- 10 mg/m3 · 10 mg/m3
- REACH Registrations
- Active
- Limited Quantities
- 5 kg · 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
Safety data
- F
- 21
- OEB
- C
- OEL
- TWA: 1 mg/m3 (0.25 ppm)
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 1
- IDLA
- 10 mg/m3
- tsca
- TSCA listed
- rtecs
- ON3675000
- ridadr
- UN 2215 8/PG III (MALEIC ANHYDRIDE, MOLTEN)
- hs_code
- 2917 14 00
- Toxicity
- LD50 orally in Rabbit: 1090 mg/kg LD50 dermal Rabbit 2620 mg/kg
- risk_code
- 22-34-42/43
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07,GHS08
- hazard_code
- C
- safety_code
- 22-26-36/37/39-45
- hazard_class
- 8
- Storage Class
- 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H302-H313-H314-H370-H372-H373-H317-H334-H402
- Limited Quantities
- 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Resp. Sens. 1Skin Corr. 1BSkin Sens. 1ASTOT RE 1 Inhalation
- Autoignition Temperature
- 870 °F
- Precautionary statements
- P501-P273-P272-P260-P270-P264-P280-P284-P342+P311-P308+P311-P362+P364-P303+P361+P353-P333+P313-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405
- Hazardous Substances Data
- 108-31-6(Hazardous Substances Data)
Chemistry & industry
Applications
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.
UsesMaleic Anhydride is heterocyclic compound used in the manufacture of unsaturated polyester resins. It has a wide range of other applications; it is used in synthetic tensides, insecticides, herbicides and fungicides.
UsesMaleic anhydride is used in Diels-Alder syntheses (as a dienophile), manufacture of alkyd-type of resins, dye intermediates, pharmaceuticals, agricultural chemicals (maleic hydrazide, malathion), in copolymerization reactions.
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.
Preparation methods
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers2 total
Additional notes
DefinitionChEBI: Maleic anhydride is a cyclic dicarboxylic anhydride that is the cyclic anhydride of maleic acid. It has a role as an allergen. It is a cyclic dicarboxylic anhydride and a member of furans.
Related reactions
Linked notes
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