Maleic Anhydride
MA · Maleic · MAN · MALIEC ANHYDRIDE · MALEIC ACID ANHYDRIDE · 2,5-FURANDIONE · CIS-BUTENEDIOIC ANHYDRIDE · ANHYDRIDE MALEIC
Identifiers & Physical Properties
| CAS No. | 108-31-6 |
|---|---|
| Molecular formula | C4H2O3 |
| Average molar mass | 98.06 g/mol |
| Monoisotopic mass | 98.00039392 g/mol |
| SMILES | O=C1C=CC(=O)O1 |
| InChIKey | FPYJFEHAWHCUMM-UHFFFAOYSA-N |
| PubChem CID | 7923 |
| ChEMBL | CHEMBL374159 |
| ChEBI | CHEBI:474859 |
| EC No. | 203-571-6 |
| DTXSID | DTXSID7024166 |
Chemical & Physical Properties
| XLogP | -0.1 |
|---|---|
| Topological polar surface area | 43.4 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 0 |
| Heavy atoms | 7 |
| Formal charge | 0 |
| Complexity | 129 |
| Melting point | 51-56 °C (lit.) |
| Boiling point | 200 °C (lit.) |
| Density | 1.48 |
| Bulk density | 700-800kg/m3 |
| Vapor density | 3.4 (vs air) |
| Vapor pressure | 0.16 mm Hg ( 20 °C) |
| Refractive index | 1.4688 (estimate) |
| Flash point | 218 °F |
| Storage conditions | Store below +30°C. |
| Solubility | Chloroform (Slightly), Ethyl Acetate (Slightly)79 g/100 mL (25 ºC) |
| pKa (acidity coefficient) | 0[at 20 ℃] |
| Physical state | powder |
| Color | White |
| pH | 0.8 (550g/l, H2O, 20℃)Hydrolysis |
| Odor | Mild acrid odor. |
| Explosive limits | 1.4-7.1%(V) |
| Sensitivity | Moisture Sensitive |
| Merck | 14,5704 |
| BRN | 106909 |
| Henry's law constant | (atmm3/mol): Not applicable - reacts with water |
| Exposure limits | 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 | 51.0(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 (partition coefficient) | -2.61 at 20℃ |
| Indirect Additives used in Food Contact Substances | MALEIC ANHYDRIDE |
| FDA 21 CFR | 175.105175.300176.170176.180177.1520177.1630177.1680177.1820178.3870 |
| CAS DataBase Reference | 108-31-6(CAS DataBase Reference) |
| EWG's Food Scores | 4-5 |
| FDA UNII | V5877ZJZ25 |
| NIST Chemistry Reference | 2,5-Furandione(108-31-6) |
| EPA Substance Registry System | Maleic anhydride (108-31-6) |
| UNSPSC Code | 12352106 |
| NACRES | NA.23 |
| GHS pictogram | GHS05,GHS07,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H302-H313-H314-H370-H372-H373-H317-H334-H402 |
| GHS 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 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Hazard symbols | C |
| Risk statements (R) | 22-34-42/43 |
| Safety statements (S) | 22-26-36/37/39-45 |
| Occupational exposure band (OEB) | C |
| Occupational exposure limit (OEL) | TWA: 1 mg/m3 (0.25 ppm) |
| UN transport number | UN 2215 8/PG III (MALEIC ANHYDRIDE) |
| Water hazard class (WGK) | 1 |
| RTECS number | ON3675000 |
| F | 21 |
| Autoignition temperature | 870 °F |
| TSCA inventory status | TSCA listed |
| Customs code | 2917 14 00 |
| Hazard class | 8Acute Tox. 4 OralEye Dam. 1Resp. Sens. 1Skin Corr. 1BSkin Sens. 1ASTOT RE 1 Inhalation |
| Packing group | III |
| Storage class | 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects |
| Hazardous substances data | 108-31-6(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 1090 mg/kg LD50 dermal Rabbit 2620 mg/kg |
| Immediately dangerous to life or health concentration | 10 mg/m3 |
| REACH registrations | Active |
| Limited quantities | 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
Safety & Regulations
| F | 21 |
|---|---|
| Occupational exposure band (OEB) | C |
| Occupational exposure limit (OEL) | TWA: 1 mg/m3 (0.25 ppm) |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Water hazard class (WGK) | 1 |
| Immediately dangerous to life or health concentration | 10 mg/m3 |
| TSCA inventory status | TSCA listed |
| RTECS number | ON3675000 |
| UN transport number | UN 2215 8/PG III (MALEIC ANHYDRIDE, MOLTEN) |
| Customs code | 2917 14 00 |
| Toxicity | LD50 orally in Rabbit: 1090 mg/kg LD50 dermal Rabbit 2620 mg/kg |
| Risk statements (R) | 22-34-42/43 |
| Signal word | Danger |
| GHS pictogram | GHS05,GHS07,GHS08 |
| Hazard symbols | C |
| Safety statements (S) | 22-26-36/37/39-45 |
| Hazard class | 8Acute Tox. 4 OralEye Dam. 1Resp. Sens. 1Skin Corr. 1BSkin Sens. 1ASTOT RE 1 Inhalation |
| 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 |
| GHS 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 |
| Autoignition temperature | 870 °F |
| GHS 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) |
Applications & Uses
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.
Uses
Maleic 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.
Uses
Maleic 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 Description
Colorless 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 & Synthesis
Preparation
To 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.