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CAS: 108-31-6
European Community (EC) Number: 203-571-6
IUPAC Name: furan-2,5-dione
Molecular Formula: C4H2O3
DESCRIPTION:
Maleic anhydride appears as colorless crystalline needles, flakes, pellets, rods, briquettes, lumps or a fused mass.
Maleic anhydride Melts at 113°F.
Maleic anhydride is Shipped both as a solid and in the molten state.
Maleic anhydride Vapors, fumes and dusts strong irritate the eyes, skin and mucous membranes.
Flash point of Maleic anhydride is 218°F.
Autoignition temperature of Maleic anhydride is 890°F.
Maleic anhydride is Used to make paints and plastics and other chemicals.
MALEIC ACID ANHYDRIDE is an organic compound with the formula C2H2(CO)2O.
MALEIC ACID ANHYDRIDE is the acid anhydride of maleic acid.
MALEIC ACID ANHYDRIDE is a colorless or white solid with an acrid odor.
MALEIC ACID ANHYDRIDE is produced industrially on a large scale for applications in coatings and polymers.
Maleic anhydride is a cyclic dicarboxylic anhydride that is the cyclic anhydride of maleic acid.
Maleic anhydride has a role as an allergen.
Maleic anhydride is a cyclic dicarboxylic anhydride and a member of furans.
Maleic anhydride is used in the formulation of resins.
Exposure to maleic anhydride may occur from accidental releases to the environment or in workplaces where it is produced or used.
Acute (short-term) inhalation exposure of humans to maleic anhydride has been observed to cause irritation of the respiratory tract and eye irritation.
Chronic (long-term) exposure to maleic anhydride has been observed to cause chronic bronchitis, asthma-like attacks, and upper respiratory tract and eye irritation in workers.
In some people, allergies have developed so that lower concentrations can no longer be tolerated. Kidney effects were observed in rats chronically exposed to maleic anhydride via gavage (experimentally placing the chemical in the stomach).
EPA has not classified maleic anhydride for carcinogenicity.
The structure of maleic acid consists of four carbon molecules along with carboxylate groups on either ends, with a double bond between the central carbon atoms.
The anhydride of maleic acid has five atoms in its cyclic molecule, the unsaturated bond undergoes free radical polymerization in the presence of an initiator.
Maleic Anhydride is a highly reactive chemical intermediate with present and potential uses in practically every field of industrial chemistry.
Maleic anhydride is used in the production of unsaturated polyester resin as well as in the manufacture of coatings, pharmaceutics, agricultural products, surfactants, and as an additive of plastics.
CAS: 108-31-6
European Community (EC) Number: 203-571-6
IUPAC Name: furan-2,5-dione
Molecular Formula: C4H2O3
Chemical and Physical Properties of MALEIC ACID ANHYDRIDE:
Molecular Weight: 98.06 g/mol
XLogP3-AA: -0.1
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 0
Exact Mass: 98.000393922 g/mol
Monoisotopic Mass: 98.000393922 g/mol
Topological Polar Surface Area: 43.4 Ų
Heavy Atom Count: 7
Formal Charge: 0
Complexity: 129
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Color/Form: Orthorhombic needles from chloroform; commercial grades furnished in fused form, as briquettes
Odor: Pungent odor
Boiling Point: 387 to 390 °F at 760 mm Hg
Melting Point: 52.8 °C
Flash Point: 102 °C
Solubility: Soluble; decomposes in hot solvent
Density: 1.43 at 59 °F
Vapor Density: 3.38
Vapor Pressure : 0.2 mm Hg
Henry's Law constant : 3.9X10-6 atm-cu m/mol at 25 °C
Stability/Shelf Life: Stable under normal laboratory storage conditions.
Autoignition Temperature: 878 °F
Decomposition :
Maleic anhydride decomposes exothermically, evolving carbon dioxide in the presence of dimethylamine, triethylamine, pyridine, or quinoline at temperatures above 150 °C.
Viscosity:
Viscosity in mPa.s (cP): 0.61 at 60 °C; 1.07 at 90 °C; 0.6 at 150 °C
Heat of Combustion: -1389.5 kJ/mol
Heat of Vaporization: 54.8 kJ/mol
pH:
pH of water solutions: 2.42 at 1X10-2 M; 2.62 at 5X10-3 M; 3.10 at 1X10-4 M
Production of MALEIC ACID ANHYDRIDE:
Maleic anhydride is produced by vapor-phase oxidation of n-butane.
The overall process converts the methyl groups to carboxylate and dehydrogenates the backbone. The selectivity of the process reflects the robustness of maleic anhydride, with its conjugated double-bond system.
Traditionally maleic anhydride was produced by the oxidation of benzene or other aromatic compounds. As of 2006, only a few smaller plants continue to use benzene.
In both cases, benzene and butane are fed into a stream of hot air, and the mixture is passed through a catalyst bed at high temperature.
The ratio of air to hydrocarbon is controlled to prevent the mixture from igniting.
Vanadium pentoxide and molybdenum trioxide are the catalysts used for the benzene route, whereas vanadium phosphate is used for the butane route:
C4H10 + 3.5 O2 → C4H2O3 + 4 H2O ∆H = −1236 kJ/mol
The main competing process entails full combustion of the butane, a conversion that is twice as exothermic as the partial oxidation.
The traditional method using benzene became uneconomical due to the high and still rising benzene prices and by complying with the regulations of benzene emissions.
In addition, in the production of maleic anhydride (4 C-atoms) a third of the original carbon atoms is lost as carbon dioxide when using benzene (6 carbon atoms).
The modern catalytic processes start from a 4-carbon molecule and only attaches oxygen and removes water; the 4-C-base body of the molecule remains intact.
Overall, the newer method is therefore more material efficient.
Parallels exist with the production of phthalic anhydride: While older methods use naphthalene, modern methods use o-xylene as feedstock.
CAS: 108-31-6
European Community (EC) Number: 203-571-6
IUPAC Name: furan-2,5-dione
Molecular Formula: C4H2O3
Reactions:
The chemistry of maleic anhydride is very rich, reflecting its ready availability and bifunctional reactivity.
Maleic anhydride 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 classic substrate for Diels-Alder reactions.
Maleic anhydride was used for work in 1928, on the reaction between maleic anhydride and 1,3-butadiene, for which Otto Paul Hermann Diels and Kurt Alder were awarded the Nobel Prize in 1950.
Maleic anhydride is through this reaction that maleic anhydride converted to many pesticides and pharmaceuticals.
Michael reaction of maleic anhydride with active methylene or methine compounds such as malonate or acetoacetate esters in the presence of sodium acetate catalyst.
These intermediates were subsequently used for the generation of the Krebs cycle intermediates aconitic and isocitric acids.
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.
Maleic anhydride is also a ligand for low-valent metal complexes, examples being Pt(PPh3)2(MA) and Fe(CO)4(MA).
On account of its cycle of 4 π electrons in an array of 5 atoms with p orbitals, maleic anhydride was long thought to exhibit antiaromaticity.
However, a thermochemical study concluded that only 8 kJ/mol of destabilization energy can be ascribed to this effect, making it weakly antiaromatic at best.
Maleic Anhydride (MAN, 2.5-furan-dion) is the anhydride of the simplest unsaturated dihydric carboxylic acid.
Maleic Anhydride is a white, aromatic, crystalline, highly hygroscopic substance that is soluble in water while forming maleic acid.
Maleic Anhydride also sublimates upon heating.
Maleic Anhydride is suitable for polyester and polyalkide resins’ manufacturers, producers of varnishes, plasticizers, copolymers and lubricants.
Uses of Maleic anhydride:
Maleic anhydride is used in many applications.
Plastics & resins:
Around 50% of world maleic anhydride output is used in the manufacture of unsaturated polyester resins (UPR).
Chopped glass fibers are added to UPR to produce fiberglass reinforced plastics that are used in a wide range of applications such as pleasure boats, bathroom fixtures, automobiles, tanks and pipes.
Maleic anhydride is hydrogenated to 1,4-butanediol (BDO), used in the production of thermoplastic polyurethanes, elastane/Spandex fibers, polybutylene terephthalate (PBT) resins and many other products.
Curing agents:
Diels-Alder reaction of maleic anhydride and butadiene and isoprene gives the respective tetrahydrophthalic anhydrides which can be hydrogenated to the corresponding hexahydrophthalic anhydrides.
These species are used as curing agents in epoxy resins.
Another market for maleic anhydride is lubricating oil additives, which are used in gasoline and diesel engine crankcase oils as dispersants and corrosion inhibitors.
Changes in lubricant specifications and more efficient engines have had a negative effect on the demand for lubricating oil additives, giving flat growth prospects for maleic anhydride in this application.
Others:
A number of smaller applications for maleic anhydride.
The food industry uses malic acid which is derivative of maleic anhydride in artificial sweeteners and flavour enhancements.
Personal care products consuming maleic anhydride include hair sprays, adhesives and floor polishes. Maleic anhydride is also a precursor to compounds used for water treatment detergents, insecticides and fungicides, pharmaceuticals, and other copolymers.
Applications of Maleic Acid Anhydride:
Maleic anhydride has a very broad range of uses from food additives to industrial applications.
• Synthetic resin raw material (unsaturated polyesters)
• Paints and coatings
• Resin modifiers
• Vinyl chloride stabilizers
• Food additives (fumaric acid, succinic acid, malic acid)
• Agricultural chemicals
• Paper sizing agents
• Imides
• Surfactants
• Plasticizers
TCC’s maleic anhydride is a highly reactive chemical intermediate with present and potential uses in practically every field of industrial chemistry.
Maleic anhydride is essential to the production of a multitude of resins and plastics, agricultural and industrial chemicals, petroleum additives, paper sizing, water treatment chemicals, epoxy curing agents, artificial sweeteners, flavor enhancers, hair sprays, pharmaceuticals and copolymers.
Its biggest single use is in the manufacture of unsaturated polyester resins.
CAS: 108-31-6
European Community (EC) Number: 203-571-6
IUPAC Name: furan-2,5-dione
Molecular Formula: C4H2O3
Packing and transport of Maleic anhydride:
Liquid maleic anhydride is available in road tankers and/or tank-containers which are made of stainless steel, which are insulated and provided with heating systems to maintain the temperature of 65-75 °C.
Tank cars must be approved for the transport of molten maleic anhydride.
Liquid/molten maleic anhydride is a dangerous material in accordance with RID/ADR.
Solid maleic anhydride pellets are transported by trucks.
Packaging is generally in 25 kg polyethylene bags.
Effects on human health and the environment:
This compound poses relatively low-risk environmental hazards, an important feature for some applications.
In humans, exposure to maleic anhydride may cause irritation to the respiratory tract, eyes, exposed mucosa, and skin.
Maleic anhydride is also a skin and respiratory sensitizer.
Maleic anhydride is a low hazard profile chemical.
Maleic anhydride rapidly hydrolyzes to form maleic acid in the presence of water and hence environmental exposures to maleic anhydride itself are unlikely.
Maleic acid is biodegradable under aerobic conditions in sewage sludge as well as in soil and water.
Food starch for use in night markets sold from a supplier in Tainan city, Taiwan, were found to contain maleic anhydride in December 2013.
The supplier was investigated regarding the 300 tons of tainted starch; an earlier inspection in November had found 32 tons.
SAFETY INFORMATION ABOUT MALEIC ACID ANHYDRIDE:
Air & Water Reactions:
Soluble in water.
Reacts slowly with water to form maleic acid and heat.
Fire Hazard:
Behavior in Fire: When heated above 300°F in the presence of various materials may generate heat and carbon dioxide. Will explode if confined.
Health Hazard:
Inhalation causes coughing, sneezing, throat irritation.
Skin contact causes irritation and redness.
Vapors cause severe eye irritation; photophobia and double vision may occur.
Reactivity Profile:
MALEIC ANHYDRIDE react vigorously on contact with oxidizing materials.
Reacts exothermically with water or steam.
Undergoes violent exothermic decomposition reactions, producing carbon dioxide, in the presence of strong bases (sodium hydroxide, potassium hydroxide, calcium hydroxide), alkali metals (lithium, sodium, potassium), aliphatic amines (dimethylamine, trimethylamine), aromatic amines (pyridine, quinoline) at temperatures above 150°C.
A 0.1% solution of pyridine (or other tertiary amine) in maleic anhydride at 185°C gives an exothermic decomposition with rapid evolution of gas.
Maleic anhydride is known as an excellent dienophile in the Diels-Alder reaction to produce phthalate ester derivatives.
These reactions can be extremely violent, as in the case of 1-methylsilacyclopentadiene.
Maleic anhydride undergoes a potentially explosive exothermic Diels-Alder reaction with 1-methylsilacyclopenta-2,4-diene at 150C, and is considered an excellent dieneophile for Diels-Alder reactions .
Isolation and Evacuation:
IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.
SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.
FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.
Firefighting:
Note: Most foams will react with the material and release corrosive/toxic gases.
SMALL FIRE: CO2, dry chemical, dry sand, alcohol-resistant foam.
LARGE FIRE: Water spray, fog or alcohol-resistant foam.
FOR CHLOROSILANES, DO NOT USE WATER; use AFFF alcohol-resistant medium-expansion foam.
If it can be done safely, move undamaged containers away from the area around the fire.
Avoid aiming straight or solid streams directly onto the product.
FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles.
Do not get water inside containers.
Cool containers with flooding quantities of water until well after fire is out.
Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank.
ALWAYS stay away from tanks engulfed in fire.
Non-Fire Response:
ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
All equipment used when handling the product must be grounded.
Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.
Stop leak if you can do it without risk.
A vapor-suppressing foam may be used to reduce vapors.
FOR CHLOROSILANES, use AFFF alcohol-resistant medium-expansion foam to reduce vapors.
DO NOT GET WATER on spilled substance or inside containers.
Use water spray to reduce vapors or divert vapor cloud drift.
Avoid allowing water runoff to contact spilled material.
Prevent entry into waterways, sewers, basements or confined areas.
SMALL SPILL: Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain.
Use clean, non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal.
Protective Clothing:
Skin: PREVENT SKIN CONTACT - Wear appropriate personal protective clothing to prevent skin contact.
Eyes: PREVENT EYE CONTACT - Wear appropriate eye protection to prevent eye contact.
Wash skin: WHEN CONTAMINATED - The worker should immediately wash the skin when it becomes contaminated.
Remove: WHEN WET OR CONTAMINATED - Work clothing that becomes wet or significantly contaminated should be removed and replaced.
Change: No recommendation is made specifying the need for the worker to change clothing after the workshift.
Provide: EYEWASH - Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substances; this is irrespective of the recommendation involving the wearing of eye protection.
First Aid:
EYES: First check the victim for contact lenses and remove if present.
Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center.
Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician.
IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing.
Gently wash all affected skin areas thoroughly with soap and water.
IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop.
IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.
INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air.
If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital.
Provide proper respiratory protection to rescuers entering an unknown atmosphere.
Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.
INGESTION: DO NOT INDUCE VOMITING.
Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems.
If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center.
IMMEDIATELY transport the victim to a hospital.
If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body.
DO NOT INDUCE VOMITING.
Transport the victim IMMEDIATELY to a hospital.
CAS: 108-31-6
European Community (EC) Number: 203-571-6
IUPAC Name: furan-2,5-dione
Molecular Formula: C4H2O3
Synonyms
MeSH Entry Terms
2,5 Furandiones
2,5-Furandiones
Anhydride, Maleic
Anhydrides, Maleic
Maleic Anhydride
Maleic Anhydrides
Depositor-Supplied Synonyms:
MALEIC ANHYDRIDE
2,5-Furandione
108-31-6
furan-2,5-dione
Maleic acid anhydride
Toxilic anhydride
Dihydro-2,5-dioxofuran
cis-Butenedioic anhydride
Maleinanhydrid
2,5-dihydrofuran-2,5-dione
RCRA waste number U147
NSC 137651
Anhydrid kyseliny maleinove
UNII-V5877ZJZ25
MALEICANHYDRIDE
CHEBI:474859
V5877ZJZ25
MFCD00005518
184288-31-1
Poly(maleic anhydride)
Maleic Anhydrides
Polymaleic anhydride
Maleinanhydrid [Czech]
2,5-Furanedione
CCRIS 2941
HSDB 183
Anhydrid kyseliny maleinove [Czech]
EINECS 203-571-6
UN2215
RCRA waste no. U147
BRN 0106909
AI3-24283
fumaric anhydride
furan-2,5-quinone
24937-72-2
68261-15-4
Maleic anhydride, 99%
Maleic Anhydride (MAN)
DSSTox_CID_4166
Epitope ID:122673
EC 203-571-6
Lytron 810 (Salt/Mix)
Lytron 820 (Salt/Mix)
Maleic anhydride, briquettes
DSSTox_RID_77313
DSSTox_GSID_24166
Maleic anhydride (briquette)
Maleic anhydride treated BSA
Maleic anhydride-1-[13C]
5-17-11-00055 (Beilstein Handbook Reference)
(Z)-butanedioic acid anhydride
Maleimide-Related Compound 11
BDBM7812
CHEMBL374159
DTXSID7024166
Maleic anhydride, powder, 95%
NSC9568
CS-Z0016
NSC-9568
ZINC8100874
Tox21_200406
NSC137651
NSC137652
NSC137653
STL197476
AKOS000121041
MCULE-5322674641
NSC-137651
NSC-137652
NSC-137653
UN 2215
NCGC00248595-01
NCGC00257960-01
BP-20394
CAS-108-31-6
Maleic anhydride, for synthesis, 99.0%
Maleic anhydride [UN2215] [Corrosive]
FT-0628122
FT-0670909
FT-0693473
M 188
M0005
Maleic anhydride treated bovine serum albumin
Maleic anhydride, puriss., >=99.0% (NT)
Maleic anhydride, SAJ first grade, >=98.0%
Maleic anhydride treated non-fat dry milk powder
A801842
Q412377
J-002092
J-521668
F0001-0164
Maleic anhydride, 95% (may contain up to 5% maleic acid)
