Identification and Related Records
- 【Name】
- Maleic anhydride
- 【Registry number】
- 108-31-6 (CAS DataBase Reference)
- 【Synonyms】
-
2,5-Furandione
MA
cis-Butenedioic anhydride
Sodium n-amylxanthate
MaleicAnhydride
- 【EINECS(EC#)】
- 203-571-6
- 【Molecular Formula】
- C4H2O3 (Products with the same molecular formula)
- 【Molecular Weight】
- 98.06
- 【Inchi】
- InChI=1/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H
- 【InChIKey】
- FPYJFEHAWHCUMM-UHFFFAOYSA-N
- 【Canonical SMILES】
- C1=CC(=O)OC1=O
108-31-6.mol
Chemical and Physical Properties
- 【Appearance】
- White crystals
- 【Density】
- 1.48
- 【Melting Point】
- 52-55℃
- 【Boiling Point】
- 200℃
- 【Refractive Index】
- 1.554
- 【Flash Point】
- 102℃
- 【Water】
- 79 g/100 mL (25℃)
- 【Solubilities】
- 79 g/100 mL (25 oC)
- 【Color/Form】
- Orthorhombic needles from chloroform; commercial grades furnished in fused form, as briquettes
Colorless needles or white lumps or pellets
NEEDLES FROM ETHER
- 【Stability】
- Stable. Combustible. Incompatible with water, strong oxidizing agents, alkali metals, strong bases, amines, most common metals, polymerization catalysts and accelerators.
- 【Storage temp】
- Store at RT.
- 【Spectral properties】
- MAX ABSORPTION (ISOOCTANE): 208 NM (LOG E= 3.90); 290 NM (LOG E= 1.11)
SADTLER REF NUMBER: 986 (IR, GRATING); 632 (UV)
IR: 971 (Coblentz Society Spectral Collection)
UV: 163 (Sadtler Research Laboratories Spectral Collection)
NMR: 48 (Varian Associates NMR Spectra Catalogue)
MASS: 61978 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)
- 【Computed Properties】
- Molecular Weight:98.05688 [g/mol]
Molecular Formula:C4H2O3
XLogP3-AA:-0.1
H-Bond Donor:0
H-Bond Acceptor:3
Rotatable Bond Count:0
Exact Mass:98.000394
MonoIsotopic Mass:98.000394
Topological Polar Surface Area:43.4
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
Feature 3D Acceptor Count:2
Feature 3D Ring Count:1
Effective Rotor Count:0.2
Conformer Sampling RMSD:0.4
CID Conformer Count:1
Safety and Handling
- 【Hazard Codes】
- C:Corrosive
- 【Risk Statements】
- R22;R34;R42/43
- 【Safety Statements 】
- S22;S26;S36/37/39;S45
- 【HazardClass】
- 8
- 【Safety】
-
Hazard Codes:?
C
Risk Statements: 22-34-42/43
R22: Harmful if swallowed.?
R34: Causes burns.?
R42/43: May cause sensitization by inhalation and skin contact.
Safety Statements: 22-26-36/37/39-45
S22: Do not breathe dust.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2215 8/PG 3
WGK Germany: 1
RTECS: ON3675000
F: 21
HazardClass: 8
PackingGroup: III
Poison by ingestion and intraperitoneal routes. Moderately toxic by skin contact. A corrosive irritant to eyes, skin, and mucous membranes. Can cause pulmonary edema. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. A pesticide. Combustible when exposed to heat or flame; can react vigorously on contact with oxidizing materials. Explosive in the form of vapor when exposed to heat or flame. Reacts with water or steam to produce heat. Violent reaction with bases (e.g., sodium hydroxide, potassium hydroxide, calcium hydroxide), alkali metals (e.g., sodium, potassium), amines (e.g., dimethylamine, triethylamine), lithium, pyridine. To fight fire, use alcohol foam. Incompatible with cations. When heated to decomposition (above 150°C) it emits acrid smoke and irritating fumes. See also ANHYDRIDES.
- 【PackingGroup 】
- III
- 【Sensitive】
- Moisture Sensitive
- 【Skin, Eye, and Respiratory Irritations】
- Inhalation causes coughing, sneezing, throat irritation. Skin contact causes irritation and redness. Vapors cause severe eye irritation; photophobia and double vision may occur.
- 【Cleanup Methods】
- Ventilate area of spill. For small quantities, sweep onto paper or other suitable material, place in an appropriate container and burn in a safe place (such as fume hood). Large quantities may be reclaimed; however, if this is not practical, dissolve in a flammable solvent (such as alcohol) and atomize in a suitable combustion chamber equipped with an appropriate effluent gas cleaning device. Large quantities should be collected in the most convenient and safe manner for reclamation or disposal in a secured sanitary landfill.
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water.
Environmental considerations: Water spill: If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
- 【Transport】
- UN 2215 8/PG 3
- 【Fire Fighting Procedures】
- Great care must be taken with the molten and vapor as material in this state is flammable. The material is a combustible solid... .
FIRE HAZARD: Volatile solid which gives off flammable vapors when molten
- 【Fire Potential】
- Great care must be taken with the molten and vapor as material in this state is flammable. The material is a combustible solid... .
FIRE HAZARD: Volatile solid which gives off flammable vapors when molten
- 【Formulations/Preparations】
- Minimum assay of 99.5%
Grade: Technical; rods, flakes, lumps, briquettes and molten
- 【DOT Emergency Guidelines】
- /GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Health: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat which will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an 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. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Evacuation: ... 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.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Fire: Note: Most foams will react with the material and release corrosive/toxic gases. Small fires: CO2, dry chemical, dry sand, alcohol-resistant foam. Large fires: Water spray, fog or alcohol-resistant foam. ... Move containers from fire area if you can do it without risk. Use water spray or fog; do not use straight streams. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders 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.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in 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. ... 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 spills: 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.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.
- 【Reactivities and Incompatibilities】
- Incompatible with alkali metals, caustics, and amines at greater than 150 deg F.
The presence of a residue of weak sodium hydroxide solution in a pressure vessel caused maleic anhydride to decompose in a runaway explosive reaction. ... Alkali and other alkaline earth compounds such as potassium, lithium, calcium, barium and magnesium compound, as well as amines and other nitrogen compound will cause explosive decomposition of maleic anhydride.
Strong oxidizers, water, alkalis, metals, caustics and amines above 150 degrees F. [Note: Reacts slowly with water (hydrolyzes) to form maleic acid].
Use of sodium or potassium carbonate or hydroxide or aqueous ammonia is not recommended for washing equipment which may later contain hot or molten maleic anhydride because of possible explosion.
- 【Other Preventative Measures】
- SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Promptly remove non-impervious clothing that becomes contaminated.
Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Avoid breathing vapors or dusts. Do not handle broken packages without protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
If material /is/ not on fire and not involved in /a/ fire keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary.
Avoid breathing vapors or dusts. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away material which may have contacted the body with copious amounts of water or soap and water.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
- 【Protective Equipment and Clothing】
- Approved organic vapor-acid gas canister; chemical goggles and face shield; rubber gloves and boots; coveralls or rubber apron.
Strict precautions should be taken to prevent contact of solution with skin or eyes ... ready access to eye irrigation solution bottles is essential.
Wear appropriate chemical protective gloves, boots and goggles.
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.
Respirator Recommendations: Up to 10 mg/cu m: (Assigned Protection Factor = 25) Any supplied-air respirator operated in a continuous-flow mode. Substance causes eye irritation or damage; eye protection needed./(Assigned Protection Factor = 50) Any self-contained breathing apparatus with a full facepiece/(Assigned Protection Factor = 50) Any supplied-air respirator with a full facepiece.
Respirator Recommendations: Emergency or planned entry into unknown concentrations or IDLH conditions (Assigned Protection Factor = 10,000) Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode/(Assigned Protection Factor = 10,000) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.
Respirator Recommendations: Escape: (Assigned Protection Factor = 50) Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister having a high-efficiency particulate filter/Any appropriate escape-type, self-contained breathing apparatus.
- 【Specification】
-
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Dusts at sufficient concentrations can form explosive mixtures with air.
Extinguishing Media: Use carbon dioxide. Use alcohol foam. Do NOT use dry powder.?
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Take precautionary measures against static discharges.
Storage: Store in a cool, dry place. Store in a tightly closed container. Store protected from moisture.
- 【Octanol/Water Partition Coefficient】
- log Kow = 1.62
- 【Report】
-
Community Right-To-Know List. Reported in EPA TSCA Inventory.
- 【Disposal Methods】
- Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U147, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
Maleic anhydride is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration. Controlled incineration; care must be taken that complete oxidation to nontoxic products occurs.
A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 deg C and residence times of seconds for liquids and gases, and longer for solids.
Use and Manufacturing
- 【Use and Manufacturing】
- Methods of Manufacturing
May be prepared by sublimation of maleic acid and phosphorous pentoxide under reduced pressure. ... Commercial production by catalytic vapor-phase oxidation of benzene or other suitable hydrocarbons.
Maleic anhydride is produced by reaction of butane with oxygen using the vanadium phosphorus oxide heterogeneous catalyst ... .
... By-product in mfr of phthalic anhydride from o-xylene
Under development is a fixed-bed process involving oxidation of butane with an undisclosed catalyst.U.S. Exports
(1975) 9.25 x 10+8 LBS
(1978) 1.31X10+9 G
(1983) 2.26X10+9 G
(1985) 1.23X10+10 gU.S. Imports
(1974) 1.2x10+7 LBS (EST)
(1977) 3.41X10+9 G
(1982) 6.25X10+8 G
(1985) 1.89X10+9 gU.S. Production
This chemical is listed as a High Production Volume (HPV) (65FR81686; http://www.epa.gov/opptintr/chemrtk/hpvchmlt.htm). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438; http://www.epa.gov/oppt/iur/index.htm).
This chemical is listed as a High Production Volume (HPV) (65FR81686; http://www.epa.gov/opptintr/chemrtk/hpvchmlt.htm). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438; http://www.epa.gov/oppt/iur/index.htm).
(1974) 2.90 x 10+8 LBS
(1976) 2.64 x 10+8 LBS (EST)
(1977) 1.33X10+11 G
(1982) 1.18X10+11 G
(1985) 1.78X10+11 g
(1988) 4.48X10+8 LBS
(1989) 192.8x10+3 metric ton
(1990) 176.9x10+3 metric ton
(1991) 172.8x10+3 metric ton
(1992) 189.1x10+3 metric ton
(1986) > 500 million to 1 billion pounds
(1990) > 500 million to 1 billion pounds
(1994) > 500 million to 1 billion pounds
(1998) > 500 million to 1 billion pounds
(2002) > 500 million to 1 billion poundsConsumption Patterns
Comonomer for unsaturated polyester resins, 52%; chem int for lube oil additives, 12%; chem int for fumaric acid, 11%; chem int for agricultural chemicals, 9%; comonomer for other copolymers, 5%; Chem int for malic acid, 4%; all other uses, 7% (1981)
End use pattern: Unsaturated polyester resins, 53%; fumaric & malic acid, 10%; agricultural chem, 8%; lube oil additives, 7%; maleic co-polymers, 7%; miscellaneous, 16% (1985)
Consumption: Maleic Anhydride. Unsaturated polyester resins, 51%; lube oil additives, 12%; food acidulants (fumaric and malic acids), 14%; copolymers, 7%; agricultural chemicals, 6%; exports, 5%; miscellaneous, 5%.
Demand: Maleic anhydride. 1988: 429 million lb; 1989: 446 million lb; 1993 /projected/: 520 million lb. (Includes exports, but not imports, which totaled 2.5 million lb last year).
- 【Sampling Procedures】
- NIOSH Method 302. Analyte: Maleic anhydride. Matrix: Air. Procedure: Bubbler collection. Flow Rate: 1.5 l/min. Sample Size: 360 liters.
EPA Method 3580. Waste Dilution. One gram of sample is weighed into a capped tube and the sample is diluted with an appropriate solvent. This method is designed for wastes that may contain organic chemicals at a level greater than 20,000 mg/kg. It is recommended that an aliquot of the diluted sample be cleaned up with an applicable technique.
Biomedical Effects and Toxicity
- 【Biomedical Effects and Toxicity】
- Dogs were fed 60 mg/kg/day maleic anhydride for 990 days. The plasma levels of maleic anhydride were determined. An uptake rate constant of 3.49X10-3/day and an elimination rate constant of 8.32X10-2/day were calculated assuming a one compartment model. According to the model 99% of steady state was reached by day 55 of the study. The dogs were maintained at steady state for the final 35 days of study.
The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.
Environmental Fate and Exposure Potential
- 【Environmental Fate/Exposure Summary】
- TERRESTRIAL FATE: The half-life for the hydrolysis of maleic anhydride is 0.37 minutes(SRC), based on a rate constant of 0.0314 1/sec at 25 deg C(1). The major fate of maleic anhydride in soil is expected to be hydrolysis(SRC). The potential for volatilization of maleic anhydride from dry soil surfaces may exist(SRC) based upon a vapor pressure of 2.5X10-1 mm Hg(2).
AQUATIC FATE: The half-life for the hydrolysis of maleic anhydride is 0.37 minutes(SRC), based on a rate constant of 0.0314 1/sec at 25 deg C(1). The major fate of maleic anhydride in aquatic environments is expected to be hydrolysis(SRC). Bioconcentration of maleic anhydride in aquatic organisms is unlikely due its rapid hydrolysis(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), maleic anhydride, which has a vapor pressure of 2.5X10-1 mm Hg at 25 deg C(2) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase maleic anhydride is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 57 hrs(SRC), calculated from its rate constant of 1.45X10-12 cu cm/molecule-sec at 25 deg C(3). Although maleic anhydride absorbs UV radiation above 290 nm(4), no information could be found concerning its photolysis(SRC). In-situ formation of small amounts of maleic anhydride may involve the reaction of hydroxyl radicals with aromatic hydrocarbons(5). Rapid removal of maleic anhydride is expected from its reaction with hydroxyl radicals (major), O3 and NO3, leading to the formation of dicarbonyls(5). Vapor-phase maleic anhydride is degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 6.5 days, calculated from its rate constant of 0.1750X10-17 cu cm/molecule-sec(6).
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