Bernsteinsureanhydrid

Succinic anhydride

HCID 7922CAS 108-30-5

Grundinformationen

Standard-SMILES
O=C1CCC(=O)O1
InChIKey
RINCXYDBBGOEEQ-UHFFFAOYSA-N
Summenformel
C4H4O3
Durchschnittliche Molmasse
100,07 g/mol
Monoisotopische Masse
100,01604399

Namen und Bezeichner

Bevorzugter Name
Succinic anhydride
IUPAC
oxolane-2,5-dione
Lokaler Name
Bernsteinsureanhydrid
Englischer Name
Succinic anhydride
Summenformel
C4H4O3
Molmasse
100.07

Namen und Synonyme

SUCCINIC ANHYDRIDE108-30-5oxolane-2,5-dioneSuccinic acid anhydrideSuccinyl oxideDihydro-2,5-furandione2,5-DiketotetrahydrofuranButanedioic anhydrideSuccinyl anhydride2,5-Furandione, dihydro-Rikacid SATetrahydro-2,5-dioxofuran
Weitere Namen anzeigen
SANsuccinicSAATetrahydrofuran-2,5-dioneSAA15-Furandione,dihydro-2Dihydro-furan-2,5-dione
2,5-DioxotetrahydrofuranTetrahydro-2,5-furandioneNCI-C55696DTXSID70212876RF4O17Z8JNSC-8518DTXCID701287CHEBI:36595

Datenbank-Bezeichner

CAS
108-30-5、68412-02-2
PubChem CID
7922
DTXSID
DTXSID7021287
ChEMBL
CHEMBL1370164
ChEBI
CHEBI:36595
UNII
6RF4O17Z8J
EC Number
203-570-0
Nikkaji
J3.248D

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,5
Polarare Oberfläche (TPSA)
43,4 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
0
Schwere Atome
7

Experimentelle und physikochemische Eigenschaften

OdorODORLESS
TasteBURNING TART TASTE
Density · 5 Einträge

1.234 at 68 °F (NTP, 1992) - Denser than water; will sink

1.503 (also given as 1.104 and 1.234)

Bulk density: 47.2 lb/cu ft

Relative density (water = 1): 1.503

1.104 @25 °C

Color/Form · 4 Einträge

NEEDLES FROM ALC; RHOMBIC PYRAMIDS FROM CHLOROFORM OR CARBON TETRACHLORIDE

COLORLESS OR LIGHT-COLORED NEEDLES OR FLAKES

Orthorhombic prisms from abs alc.

Succinic anhydride forms rhombic pyramidal or bipyramidal crystals.

Solubility · 5 Einträge

less than 1 mg/mL at 70 °F (NTP, 1992)

Insoluble in water

IN ETHANOL AT 25 °C: 2.56 G/100 ML; IN ETHER AT 25 °C: 0.64 G/100 ML; IN CHLOROFORM AT 25 °C: 0.87 G/100 ML

Soluble in chloroform, carbon tetrachloride, alcohol; very slightly soluble in ether and water.

Solubility in water: none

Flash Point · 2 Einträge

157 °C

157 °C

Physikochemische Eigenschaften

Schmelzpunkt
118 · 118-120 °C (lit.)
Siedepunkt
261 °C · 261 °C (lit.)
Dichte
1 · 1,572 g/cm3
Dampfdichte
3.5 · 3.5 (vs air)
Dampfdruck
1 mm · 1 mm Hg ( 92 °C)
Brechungsindex
1.4688 · 1.4688 (estimate)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral];H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation];H317: May cause an allergic skin reaction [Warning Sensitization, Skin];H318: Causes serious eye damage [Danger Serious eye damage/eye irritation];H334: May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

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, 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 0.2% (2 of 1275) of reports.

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: 2,5-Furandione, dihydro-

Hazard Traits - Respiratory Toxicity;Authoritative List - EC Annex VI Resp. Sens. - Cat. 1;Report - if used as a fragrance or flavor ingredient

2,5-Furandione, dihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,5-Furandione, dihydro- 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: 18-05-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/2061;Status: Active Update: 05-09-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/30019

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

Fire Hazards · 2 Einträge

Flash point data for this compound are not available, however, it is probably combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

Fire PotentialCombustible
Health Hazards · 1 Eintrag

SYMPTOMS: Symptoms of exposure to this chemical may include eye, skin, mucous membrane and respiratory tract irritation; it may blister and burn the skin on contact.;ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits acrid smoke and fumes of carbon monoxide and carbon dioxide. It may cause eye, respiratory tract, mucous membrane and skin irritation. It is a suspected carcinogen. (NTP, 1992)

Hazards Summary · 1 Eintrag

A skin, eye, and respiratory tract irritant; [HSDB] May cause blisters and burns to skin; [CAMEO] The substance is severely irritating to the eyes and is irritating to the respiratory tract. [ICSC] An irritant (severe to eyes); [MSDSonline] See ACID ANHYDRIDES.

Reactive GroupAnhydrides

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fires involving this compound should be controlled using a Halon, carbon dioxide, or dry chemical extinguisher. A water spray may also be used. (NTP, 1992)

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4 Einträge

Fresh air, rest.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink.

First Aid · 1 Eintrag

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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;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. 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. Be prepared to transport the victim to a hospital if advised by a physician. 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. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Cleanup MethodsRemove all ignition sources. Sweep spilled substance into covered containers; if appropriate, moisten first to prevent dusting.
Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.;STORAGE PRECAUTIONS: You should store this material at ambient temperatures, and protect it from moisture. (NTP, 1992)

Disposal Methods · 1 Eintrag

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: The half-life for the hydrolysis of succinic anhydride is 4.3 minutes(SRC), based on a rate constant of 0.0027 1/sec at 25 °C(1). The major fate of succinic anhydride in soil is expected to be hydrolysis (SRC). Succinic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.5X10-3 mm Hg(2).

AQUATIC FATE: The half-life for the hydrolysis of succinic anhydride is 4.3 minutes(SRC), based on a rate constant of 0.0027 1/sec at 25 °C(1). The major fate of succinic anhydride in aquatic environments is expected to be hydrolysis(SRC). Bioconcentration of succinic anhydride in aquatic organisms is unlikely due its rapid hydrolysis(SRC). Approximately 78% of the succinic anhydride added to activated sewage sludge was biodegraded within five days(2,3); however, hydrolysis is expected to be the principal fate of succinic anhydride in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), succinic anhydride, which has a vapor pressure of 1.5X10-3 mm Hg at 25 °C(2) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase succinic 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 70 days (SRC), calculated from its rate constant of 4.56X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation and by ingestion.
Signs and Symptoms · 3 Einträge

Cough. Shortness of breath. Sore throat.

Redness. Pain.

Diarrhoea. Nausea. Vomiting.

Ongoing Test Status · 1 Eintrag

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=108-30-5]

Soil Adsorption/MobilityAdsorption of succinic anhydride in soil is unlikely due its rapid hydrolysis(1).

Regulatorische Informationen

Regulatory Information · 5 Einträge

Chemical: 2,5-Furandione, dihydro-

Hazard Traits - Respiratory Toxicity;Authoritative List - EC Annex VI Resp. Sens. - Cat. 1;Report - if used as a fragrance or flavor ingredient

2,5-Furandione, dihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,5-Furandione, dihydro- 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: 18-05-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/2061;Status: Active Update: 05-09-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/30019

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

Sicherheitsdaten

F
21
wgk
1
tsca
TSCA listed
ridadr
UN 3261 8 / PGII
hs_code
29171990
RTECS-Nr.
WN0875000

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsCytoplasm;Extracellular

Verwendung und Herstellung

Uses · 6 Einträge

Used as an acidulant and dehydrating agent (food processing), cross-linking agent (epoxy resins and ion exchange membranes), and in gas and water treatment; Also used to make adhesives, paint drying oils, dyes, pharmaceuticals, esters, elastomers (cable coverings and extruded articles), hardeners for resins, starch modifiers in foods, succinylated monoglyceride food emulsifiers, silver haloid photographic emulsions, detergents, cosmetics, plant growth regulators, textiles, surface-active agents, lubricant additives, fire-retardants for paper, insect repellants, and herbicides; [HSDB]

Textiles (Fiber & Fabric Manufacturing) [Category: Industry];Sewer and Wastewater Treatment [Category: Industry];Plastic Composites Manufacturing [Category: Industry]

Acidulant in processed foods

Dehydrating agent in dry food mixtures

Chemical intermediate for adhesives, dyes; elastomers for special tubings, cable coverings, and extruded articles.

Manufacture of chemicals, pharmaceuticals, esters; hardener for resins, starch modifier in foods.

U.S. Exports · 3 Einträge

(1972) No Data

(1975) No Data

(1984) 2.07X10+8 g /Anhydrides, Acyl Halides, and their derivatives/

U.S. Imports · 3 Einträge

(1972) 4.5X10+6 G (PRINCPL CUSTOMS DISTS)

(1974) 2.7X10+6 G (PRINCPL CUSTOMS DISTS)

(1984) 1.99X10+9 g /Organic acid anhydrides/

U.S. Production · 6 Einträge

2023: 50,000 - <250,000 lb;2022: 1,000,000 - <2,500,000 lb;2021: 400,000 - <550,000 lb;2020: 550,000 - <700,000 lb

2,5-Furandione, dihydro- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1972) PROBABLY GREATER THAN 4.54X10+5 G

(1975) PROBABLY GREATER THAN 9.08X10+5 G

(1986) No Data

For more U.S. Production (Complete) data for SUCCINIC ANHYDRIDE (9 total), please visit the HSDB record page.

Industry UsesCorrosion inhibitor;Not Known or Reasonably Ascertainable;pH regulating agent;Other
Methods of Manufacturing · 4 Einträge

Hydrogenation of maleic anhydride or fumaric acid; heating of succinic acid at elevated temperature and pressure.

...By treating succinic acid with diketene, succinyl chloride or acetic anhydride, or by reacting diethyl ester with boron chloride.

... Warming succinic acid with acetic anhydride, acetyl chloride, or phosphorus oxychloride.

Succinic anhydride is manufactured by catalytic hydrogenation of maleic anhydride. In the most widely used commercial process this reaction is performed in the liquid phase, at temperatures of 120-180 °C and at moderate pressures, in the range of 500-4000 kPa (72-580 psi). Catalysts mentioned in the patent literature include nickel, Raney nickel, palladium on different carriers, and palladium complexes.

Anwendungen · 2 Einträge

BeschreibungSuccinic anhydride, also called di hydro - 2,5- furandione , is an organic compound with the molecular formula C4H4O3.This colorless solid is the acid anhydride of succinic acid.

VerwendenSuccinic Anhydride is an acidulant that hydrolyzes very slowly to succinic acid in water. it has thermal stability and a low melting point of 118°c which permits it to be used in products at compara- tively low temperatures. it is used as a leavening acidulant for bak- ing powder.

Darstellung · 1 Eintrag

synthetischeA solution of succinic acid (500 mg, 42 mmol) and triethylamine (1.23 mL, 42 mmol) in anhydrous THF (120 mL) was allowed to react with triphosgene (42 mg, 7.0 mmol) at ice-water temperature for 10 min. The reaction mixture was subsequently stirred for a further 15 min at room temperature. The solution was then filtered, and the filtrate was concentrated to dryness. The residue was crystallized from ethyl acetate to afford the desired product as white crystals (370 mg, 85%).

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