2,5-푸란디온,동종중합체,나트륨염

Maleic Anhydride

HCID 178805087CAS 70247-90-4

기본 정보

표준 SMILES
O=C1C=CC(=O)O1
InChIKey
FPYJFEHAWHCUMM-UHFFFAOYSA-N
분자식
C4H2O3
평균 분자량
98.06 g/mol

개요

Maleic anhydride appears as 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.

이름 및 식별자

우선 이름
Maleic Anhydride
IUPAC
furan-2,5-dione
현지명
2,5-푸란디온,동종중합체,나트륨염
영어명
2,5-Furandione, homopolymer, sodium salt
분자식
C4H2O3
분자량
98.06

이름 및 동의어

MALEIC ANHYDRIDEfuran-2,5-dione2,5-Furandione108-31-6Toxilic anhydrideMaleic acid anhydridecis-Butenedioic anhydrideDihydro-2,5-dioxofuranMaleinanhydridRCRA waste number U1472,5-FuranedioneAnhydrid kyseliny maleinove
이름 더 보기
2,5-푸란디온,동종중합체,나트륨염2,5-Furandione, homopolymer, sodium saltPolymaleic anhydride,hydrolyzed,sodium saltMaleic anhydride homopolymer,diphenyl terminated,sodium saltPolymaleic anhydride, hydrolyzed, sodium salt 2,5-Furandione,homopolymer,sodium salt2,5-Furandione, homopolymer, sodium salt Maleic anhydride homopolymer, diphenyl terminated, sodium salt
DTXSID7024166CHEBI:474859V5877ZJZ25NSC-137651DTXCID804166Anhydride, MaleicRefChem:5978203-571-6

데이터베이스 식별자

CAS
70247-90-4
ChEMBL
CHEMBL374159
ChEBI
CHEBI:474859
UNII
V5877ZJZ25
EC Number
203-571-6、606-024-3
Nikkaji
J2.419H

물성

구조 계산 물성

XLogP
-0.1
극성 표면적
43.4 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
3
회전 가능 결합 수
0
무거운 원자 수
7

실험 및 물리화학적 성질

Chemical Classes · 2건

Hazardous Air Pollutants (HAPs)

Corrosives

PolymersPlastics & Rubber -> Acid Anhydrides, Cyclic
pHpH of water solutions: 2.42 at 1X10-2 M; 2.62 at 5X10-3 M; 3.10 at 1X10-4 M
SpringerMaterials PropertiesCoriolis coupling
PesticidesPesticide -> EPA IRIS
LogP · 2건

log Kow = 1.62

1.62 (calculated)

물리화학적 성질

EPA
2 · 2,5-Furandione, homopolymer, sodium salt (70247-90-4)

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P333+P317, P342+P316, P362+P364, P363, P403, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (2 of 4575) of reports.

Danger

H302 (> 99.9%): Harmful if swallowed [Warning Acute toxicity, oral]

유해성 정보

Regulatory Information · 6건

Chemical: 2,5-Furandione

Hazard Traits - Respiratory Toxicity

Regulation (EC) No 258/1997

2,5-Furandione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,5-Furandione are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 02-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15798

Maleic anhydride: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 2,5-Furandione: Human health tier II assessment
DOT LabelCorrosive
Fire Hazards · 3건

Behavior in Fire: When heated above 300 °F in the presence of various materials may generate heat and carbon dioxide. Will explode if confined. (USCG, 1999)

· Combustible material: may burn but does not ignite readily.

Combustible. Many reactions may cause fire or explosion. See Chemical dangers Finely dispersed particles form explosive mixtures in air.

Fire Potential · 3건

Great care must be taken with the molten and vapor as material in this state is flammable. The material is a combustible solid... .

Combustible solid, but may be difficult to ignite.

FIRE AND EXPLOSION HAZARDS: Combustible solid. Dust cloud may be exploded by flame or spark.

Health Hazards · 2건

Inhalation causes coughing, sneezing, throat irritation. Skin contact causes irritation and redness. Vapors cause severe eye irritation; photophobia and double vision may occur. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

안전 및 보호

Fire Fighting · 2건

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

Use water spray, alcohol-resistant foam, carbon dioxide. NO powder.

First Aid Measures · 4건

Fresh air, rest. Half-upright position. Refer immediately for medical attention.

First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Wear protective gloves when administering first aid. Refer immediately for medical attention.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Give nothing to drink. Do NOT induce vomiting. Refer immediately for medical attention.

Accidental Release Measures · 2건

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3건

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.

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Store only in original container. Separated from strong oxidants, strong reducing agents and incompatible materials. Dry. Store in an area without drain or sewer access.
Firefighting Hazards · 2건

Water stream or foam may cause frothing. Use dry chemical, carbon dioxide, or water spray.

Reacts violently with fire extinguishing agents such as powder.

독성 정보

Interactions · 2건

Maleic anhydride retarded the carcinogenic activity of benzo(a)pyrene and dibenzo(a,h)anthazene when applied together with these carcinogens to mice dermally.

The effects of a mixture of biphenyl plus diphenyl-ether and maleic-anhydride on mortality and cholinesterase activity were studied in mice and rats. To determine median lethal dose (LD50), the compounds were introduced into the stomachs of white-mice or white-rats in a 3% starch solution. The data was treated by probit analysis. The LD50 for the mixture was 3210 mg/kg for white-mice and 5480 mg/kg for white-rats. The LD50 of maleic-anhydride for these species was 465 mg/kg and 850 mg/kg, respectively. The combined actions of the mixture and maleic-anhydride were studied at their LD50s in 90 white-mice. The biological effect of the combined administration equaled the sum expected from the addition of the toxic effect of each substance. To explain any cumulative properties of the mixture and maleic-anhydride, white-rats were treated orally for 20 days with 3% starch solutions of 0.1 LD50 of the mixture in the first group, 0.1 LD50 maleic-anhydride in the second group, 0.05 LD50 of each in the third group, and only starch solution in the fourth, control group. No animals died, but toward the end of the experiment, all test animals were less active than controls. Cholinesterase activity was not altered in any group. The threshold doses for depression of blood cholinesterase was determined to be 0.152 mg/L for maleic-anhydride and 0.126 mg/L for the mixture. When these doses were combined and administered to white-rats, an additive depression of cholinesterase activity was seen. .../It was concluded/ that the toxic effects of the mixture and maleic-anhydride are additive.

Target Organs · 2건

Urinary

Eyes, skin, respiratory system

Ecotoxicity Values · 5건

LC50; Species: Lepomis macrochirus (Bluegill); Conditions: static, aeration by "oxygenation interface method" (contact between pure oxygen and test sample); test organisms acclimated to test temperature for 10-14 days; 20 °C, pH 6.9-7.5, dechlorinated water, total hardness 84.0-163.0 mg/L (as CaCO3), 5 mg O2/L or higher; Concentration: 150 mg/L for 24 hr

LC50; Species: Lepomis macrochirus (Bluegill); Conditions: static, aeration by "oxygenation interface method" (contact between pure oxygen and test sample); test organisms acclimated to test temperature for 10-14 days; 20 °C, pH 6.9-7.5, dechlorinated water, total hardness 84.0-163.0 mg/L (as CaCO3), 5 mg O2/L or higher; Concentration: 138 mg/L for 48 hr

LC50; Species: Leuciscus idus melanotus (Golden orfe); Conditions: static; test organisms acclimated in drinking water; 10 °C, pH 3.1-5.5; Concentration: 275 mg/L for 48 hr

EC50; Species: Daphnia magna (Water flea); Conditions: static, 20 °C, pH 8.0; test solution neutralized; Concentration: 5600 mg/L for 24 hr; Effect: immobilization

For more Ecotoxicity Values (Complete) data for MALEIC ANHYDRIDE (11 total), please visit the HSDB record page.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that maleic anhydride is expected to have very high mobility in soil(SRC). However, maleic anhydride hydrolyzes rapidly in water forming maleic acid with hydrolysis half-lives of 3.32 and 0.37 minutes at 0 and 25.1 °C respectively(3). Therefore, potential leaching in soil is expected to be dominated by degradation to maleic acid(SRC). Volatilization of maleic anhydride from moist soil surfaces is not expected to be an important fate process due to hydrolysis(SRC). Maleic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.25 mm Hg at 25 °C(4). Various biodegradation screening tests have found maleic anhydride to be readily biodegradable(5,6). However, available biodegradation rates for maleic anhydride are expected to reflect the hydrolysis product maleic acid(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that maleic anhydride is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.9X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). However, maleic anhydride hydrolyzes rapidly in water forming maleic acid with hydrolysis half-lives of 3.32 and 0.37 minutes at 0 and 25.1 °C, respectively(3). Therefore, volatilization is not expected to be an important fate process in water due to hydrolysis(SRC). Bioconcentration of maleic anhydride in aquatic organisms is unlikely due its rapid hydrolysis(SRC). Various biodegradation screening tests have found maleic anhydride to be readily biodegradable(5,6). However, available biodegradation rates for maleic anhydride are expected to reflect the hydrolysis product maleic acid(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 0.25 mm Hg at 25 °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 11 days(SRC), calculated from its rate constant of 1.45X10-12 cu cm/molecule-sec at 23 °C(3). Vapor-phase maleic anhydride is also 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 estimated rate constant of 0.18X10-17 cu cm/molecule-sec at 25 °C that was derived using a structure estimation method(4). The nitrate radical (NO3) is the dominant atmospheric oxidant during the night-time in most atmospheric environments(5). Vapor-phase maleic anhydride is degraded in the atmosphere by reaction with nitrate radicals(SRC); the half-life for this reaction in air is estimated to be 8 hours(SRC), calculated from its rate constant of 1.0X10-13 cu cm/molecule-sec at 25 °C(6). Removal of maleic anhydride via reaction with hydroxyl radicals, ozone and nitrate radicals leads to the formation of dicarbonyls(7). Maleic anhydride absorb at wavelengths >290 nm(6) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). In the vapor phase, hydrolysis of maleic anhydride is completed in 21 hr at 96% relative humidity while no hydrolysis occurs at 50% relative humidity(8).

Food Survey ValuesMaleic anhydride is reported to be a constituent of coffee aroma(1).
Adverse EffectsDermatotoxin - Skin burns.

규제 정보

FDA RequirementsMaleic anhydride is an indirect food additive for use only as a component of adhesives.
RCRA Requirements · 1건

U147; As stipulated in 40 CFR 261.33, when 2,5-furandione, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

TSCA Requirements · 1건

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Maleic anhydride is included on this list. Effective date: 9/10/84; Sunset date: 9/10/94.

FIFRA Requirements · 1건

Residues of maleic acid and maleic anhydride are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: Stabilizer. Limit: For pesticide formulations applied to apples with a minimum preharvest interval of 21 days.

Atmospheric Standards · 2건

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Maleic anhydride is produced, as an intermediate or a final product, by process units covered under this subpart.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Maleic anhydride is included on this list.

CERCLA Reportable Quantities · 1건

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).

안전 데이터

tsca
TSCA listed
기존화학 물질
KE-22840

화학 및 산업

약리 정보

Metabolism/MetabolitesMaleic anhydride is probably hydrolyzed to maleic acid and then hydroxylated to malic acid, which participates in the Krebs cycle or may be excreted unchanged or in conjugated form. Maleic acid is an antimetabolite of fumaric acid.
Absorption, Distribution and Excretion · 5건

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.

Signs of central nervous system depression were observed in rats in a single-dose inhalation study, indicating that absorption occurs via this route.

A study of plasma levels in dogs following long-term (90 days) dietary administration of maleic anhydride at a concentration of 60 mg/kg b.w indicates that the substance is absorbed via this route. Plasma concentrations were measured on day 1, 3, 12, 29 and 90. It was calculated that a steady plasma level was reached after 55 days. In male dogs the plasma concentration was 1.8-3.5 ug/L

Maleic anhydride has a rather low order of toxicity via the dermal route indicating limited absorption via this route.

용도 및 제조

Uses · 6건

Maleic anhydride is used primarily in the formation of unsaturated polyester resins for use in boats, autos, trucks, buildings, piping, and electrical goods. Lube oil adhesives synthesized from maleic anhydride are used to prolong oil-change intervals and improve engine efficiency. Maleic anhydride is also used to make copolymers, pesticides, and other organic compounds, and in Diels-Alder syntheses.

Used in Diel-Alder syntheses; copolymerization reactions; and manufacturing of alkyd-type resins, dye intermediates, pharmaceuticals, and pesticides (Malathion). [Merck Index] Other uses are coatings, epoxies, and paper sizing resins; [ACGIH]

Pulp and Paper Processing [Category: Industry]

In Diels-Alder syntheses (as a dienophile), manufacture of alkyd-type of resins, dye intermediates, pharmaceuticals, agricultural chemicals (maleic hydrazide, malathion), in copolymerization reactions.

... Fumaric and tartaric acid manufacture; pesticides; preservative for oils and fats; permanent-press resins (textiles), Diels-Alder reactions.

Because of its properties as a dicarboxylic anhydride with a double bond, MA /maleic anhydride/ can be used for both polycondensation and polyaddition. Polyester and alkyd resins, lacquers, plasticizers, copolymers, and lubricants are the most important technical end products. Examples of industrially important copolymers are: MA-styrene (for engineering plastics) and MA-acrylic acid (used in the detergent industry). Polyester and alkyd resins, in particular, are used in the production of fiberglass reinforced plastics, in the construction and electrical industries, and in pipeline and marine construction. ... Smaller amounts of MA are used in the production of pesticides (captan, malathion) and growth inhibitors (maleic acid hydrazide). ... When added to drying oils, MA reduces the drying time and improves the coating quality of lacquers.

U.S. Exports · 4건

(1975) 9.25 x 10+8 LBS

(1978) 1.31X10+9 G

(1983) 2.26X10+9 G

(1985) 1.23X10+10 g

U.S. Imports · 3건

(1977) 3.41X10+9 G

(1982) 6.25X10+8 G

(1985) 1.89X10+9 g

U.S. Production · 6건

2023: 250,000,000 - <400,000,000 lb

(1974) 2.90 x 10+8 LBS

(1977) 1.33X10+11 G

(1982) 1.18X10+11 G

(1985) 1.78X10+11 g

For more U.S. Production (Complete) data for MALEIC ANHYDRIDE (18 total), please visit the HSDB record page.

Consumption Patterns · 4건

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).

Consumer UsesIntermediate

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