HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Bernsteinsureanhydrid
SAN · succinic · SAA · SUCCINIC ACID ANHYDRIDE · DIHYDRO-2,5-FURANDIONE · BUTANEDIOIC ANHYDRIDE · Tetrahydrofuran-2,5-dione · SAA1
Identifikatoren & physikalische Daten
| CAS No. | 108-30-5 |
|---|---|
| Summenformel | C4H4O3 |
| Durchschnittliche Molmasse | 100,07 g/mol |
| Monoisotopische Masse | 100,01604399 g/mol |
| SMILES | O=C1CCC(=O)O1 |
| InChIKey | RINCXYDBBGOEEQ-UHFFFAOYSA-N |
| PubChem CID | 7922 |
| ChEMBL | CHEMBL1370164 |
| ChEBI | CHEBI:36595 |
| EC No. | 203-570-0 |
| DTXSID | DTXSID7021287 |
| Lokaler Name | Bernsteinsureanhydrid |
Chemische & physikalische Eigenschaften
| XLogP | -0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 43,4 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 102 |
| Geruch | ODORLESS |
| Geschmack | BURNING TART TASTE |
| Dichte | 1.234 at 68 °F (NTP, 1992) - Denser than waterwill sink1.503 (also given as 1.104 and 1.234)Bulk density: 47.2 lb/cu ftRelative density (water = 1): 1.5031.104 @25 °C1,572 g/cm3 |
| Color/Form | NEEDLES FROM ALCRHOMBIC PYRAMIDS FROM CHLOROFORM OR CARBON TETRACHLORIDECOLORLESS OR LIGHT-COLORED NEEDLES OR FLAKESOrthorhombic prisms from abs alc.Succinic anhydride forms rhombic pyramidal or bipyramidal crystals. |
| Löslichkeit | less than 1 mg/mL at 70 °F (NTP, 1992)Insoluble in waterIN ETHANOL AT 25 °C: 2.56 G/100 MLIN ETHER AT 25 °C: 0.64 G/100 MLIN CHLOROFORM AT 25 °C: 0.87 G/100 MLSoluble in chloroform, carbon tetrachloride, alcoholvery slightly soluble in ether and water.Solubility in water: none62.9g/l Hydrolysis<0.1 g/100 mL at 21 ºC (decomposes) |
| Flammpunkt | 157 °C157°C |
| Siedepunkt | 502 °F at 760 mmHg (NTP, 1992)261 °C at 760 mm Hg261 °C @760 [mm Hg]261 °C (lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | 247.3 °F (NTP, 1992)119.6 °C119 °C118-120 °C (lit.) |
| Dampfdichte | 3.7 (NTP, 1992) - Heavier than airwill sink (Relative to Air)Relative vapor density (air = 1): 3.453.5 (vs air) |
| Dampfdruck | 1 mmHg at 197.6 °F5 mmHg at 239.0 °F10 mmHg at 262.8 °F (NTP, 1992)0.0015 [mmHg]Vapor pressure = 1 mm Hg at 92 °C1.5X10-3 mm Hg at 25 °C (estrapolated)Vapor pressure, kPa at 92 °C: 1.31 [mm Hg] @92 °C1 mm Hg ( 92 °C) |
| Heat of Combustion | -1537.9 kJ/mol |
| Brechungsindex | 1.4688 (estimate) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 4.67[at 20 ℃] |
| Farbe | White to Off-White |
| Wichte | 1.2340 (20℃) |
| pH | 2.7 (10g/l, H2O) |
| Geruch | Odorless |
| Merck | 14,8870 |
| BRN | 108441 |
| Stabilität | Stable. Incompatible with oxidising agents, strong acids, strong bases, alcohols, amines. Avoid exposure to water or moisture. |
| InChI | 1S/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H2 |
| InChIKey | RINCXYDBBGOEEQ-UHFFFAOYSA-N |
| SMILES | O=C1CCC(=O)O1 |
| LogP (Verteilungskoeffizient) | 2.44 at 40℃ |
| CAS Datenbank | 108-30-5(CAS DataBase Reference) |
| NIST chemische Informationen | 2,5-Furandione, dihydro-(108-30-5) |
| EPA chemische Informationen | Succinic anhydride (108-30-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302: 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. |
|---|---|
| Regulatorische Informationen | Chemical: 2,5-Furandione, dihydro-Hazard Traits - Respiratory ToxicityAuthoritative List - EC Annex VI Resp. Sens. - Cat. 1Report - if used as a fragrance or flavor ingredient2,5-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/2061Status: Active Update: 05-09-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/30019Succinic anhydride: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | 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. |
| Brandpotenzial | Combustible |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this chemical may include eye, skin, mucous membrane and respiratory tract irritationit 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) |
| Gefahrenübersicht | 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. |
| Reaktive Gruppe | Anhydrides |
| EG-Einstufung | Symbol: XiR: 36/37S: (2)-25 |
| Special Reports | DHHS/NTPToxicology & Carcinogenesis Studies of Succinic Anhydride in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 373 (1990) NIH Publication No. 90-2828 |
| Reactivity Profile | SUCCINIC ANHYDRIDE reacts exothermically with water. Reactions are usually slow, but might become violent if local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases. |
| Chemical Dangers | Decomposes on heating. This produces irritating fumes. |
| Air and Water Reactions | Reacts slowly with water. Insoluble in water. |
| Other Hazardous Reactions | Evaporation at 20 °C is negligiblea harmful concentration of airborne particles can, however, be reached quickly when dispersed. |
| Brandbekämpfung | 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. |
| Erste-Hilfe-Maßnahmen | 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. |
| Erste Hilfe | 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 areatake 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 usedif 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) |
| Reinigungsverfahren | Remove all ignition sources. Sweep spilled substance into covered containersif appropriate, moisten first to prevent dusting. |
| Freisetung ohne Brand | 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) |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Verschüttetes entsorgen | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. |
| Preventive Measures | Prevent dispersion of dust!Inhalation /exposure can be prevented by/ local exhaust or breathing protection. Skin /exposure can be prevented by/ protective gloves. Eye /exposure can be prevented by/ safety goggles, or eye protection in combination with breathing protection if powder. /from table/Do not eat, drink, or smoke during work. /from table/ |
| Eye Prevention | Wear safety goggles or eye protection in combination with breathing protection if powder. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered. |
| Skin Prevention | Protective gloves. |
| Umweltverhalten | 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). |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| Expositionspfade | The substance can be absorbed into the body by inhalation and by ingestion. |
| Signs and Symptoms | Cough. Shortness of breath. Sore throat.Redness. Pain.Diarrhoea. Nausea. Vomiting. |
| Ongoing Test Status | 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/Mobility | Adsorption of succinic anhydride in soil is unlikely due its rapid hydrolysis(1). |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ The substance irritates the eyes, the skin and the respiratory tract./SIGNS AND SYMPTOMS/ Inhalation /may cause/ cough, shortness of breath, sore throat. Skin or eye /exposure may cause/ redness, pain. Ingestion /may cause/ diarrhea, nausea, vomiting. /from table/ |
| Artificial Pollution Sources | Succinic anhydride's production and use as a chemical reactant and intermediate, in the manufacture of pharmaceuticals and esters, as a hardener for resin(1), and as an acidulant in foods(2) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: Approximately 78% of the succinic anhydride added to activated sewage sludge at 50 ug/L was biodegraded within five days at 25 °C (1,2)however, hydrolysis is expected to be the principal fate of succinic anhydride in water and these results are probably for succinic acid, the hydrolysis product(SRC). |
| Carcinogen Classification | Succinic anhydrideGroup 3: Not classifiable as to its carcinogenicity to humansVolume 15: (1977) Some Fumigants, the Herbicides 2,4-D and 2,4,5-T, Chlorinated Dibenzodioxins and Miscellaneous Industrial ChemicalsVolume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987440 pagesISBN 92-832-1411-0 (out of print) |
| Environmental Bioconcentration | Bioconcentration of succinic anhydride in aquatic organisms is unlikely due its rapid hydrolysis(1). Experimental bioconcentration factors (chemical concentration in fish/chemical concentration in water) of succinic anhydride in fish (Golden ide) were less than 10(2,3). |
| Volatilization from Water/Soil | Hydrolysis is expected to be the predominate fate of succinic anhydride in moist soil and water(1). Succinic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.5X10-3 mm Hg(2). |
| F | 21 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3261 8 / PGII |
| Zollcode | 29171990 |
| RTECS-Nr. | WN0875000 |
| R-Sätze (R) | 36/37-22 |
| Toxizität | LD50 orally in Rabbit: 1510 mg/kg |
| Gefahrensymbole | Xi,Xn |
| Sicherheitshinweise (S) | 25-46 |
| Gefahrenklasse | 8Acute Tox. 4 OralEye Dam. 1Resp. Sens. 1Skin Corr. 1BSkin Sens. 1 |
| Lagerklasse | 8A - Combustible corrosive hazardous materials |
| Gefahrstoffdaten | 108-30-5(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 480 °C |
Anwendungen & Verwendung
Beschreibung
Succinic 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.
Verwenden
Succinic 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.
Herstellung & Synthese
synthetische
A 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%).