Phthalsureanhydrid
Isobenzofuran-1,3-dione · phthalic · PTHALIC ANHYDRIDE · PHATHALIC ANHYDRIDE · 2-Benzofuran-1,3-dione · O-PHTHALIC ANHYDRIDE · 1,3-ISOBENZOFURANDIONE · PHTHALIC ACID ANHYDRIDE
Identifikatoren & physikalische Daten
| CAS No. | 85-44-9 |
|---|---|
| Summenformel | C8H4O3 |
| Durchschnittliche Molmasse | 148,11 g/mol |
| Monoisotopische Masse | 148,01604399 g/mol |
| SMILES | O=C1OC(=O)c2ccccc21 |
| InChIKey | LGRFSURHDFAFJT-UHFFFAOYSA-N |
| PubChem CID | 6811 |
| ChEMBL | CHEMBL1371297 |
| ChEBI | CHEBI:36605 |
| EC No. | 201-607-5 |
| DTXSID | DTXSID2021159 |
| Lokaler Name | Phthalsureanhydrid |
Chemische & physikalische Eigenschaften
| XLogP | 1,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 43,4 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 187 |
| Stoffklassen | Hazardous Air Pollutants (HAPs)CorrosivesPhthalate |
| Polymers | Plastics & Rubber -> Acid Anhydrides, Cyclic |
| SpringerMaterials Properties | Boiling point |
| Pestizide | Pesticide -> EPA IRIS |
| LogP (Verteilungskoeffizient) | log Kow = 1.60 |
| Geruch | MildCharacteristic, acrid odor |
| Dichte | 1.2 at 275 °F 1.53 at 20 °C (solid) (USCG, 1999) - Denser than waterwill sink1.20 (molten)1.53 (flake)1.53 g/cm³1.53 at 68 °F1.527 @ 4°C1.53 (Flake) 1.20 (Molten)1,53 g/cm3 |
| Viscosity | 1.19 mPa.s at 132 °C1.125 mPa.s at 155 °C |
| Color/Form | White, lustrous needlesColorless needlesmonoclinic or rhombic prismsWhite needles from alcohol and benzeneWhite solid (flake) or a clear colorless liquid (molten) |
| Löslichkeit | Decomposes (NTP, 1992)In water, 6,000 mg/L at 25 °CIn water, 6,200 mg/L at 26 °C5,964 mg/L at room temperatureIn water, 6,200 to 6,400 mg/L at 20-25 °CIn water, 16,400 mg/L including rapid hydrolysis to phthalic acidFor more Solubility (Complete) data for PHTHALIC ANHYDRIDE (7 total), please visit the HSDB record page.6g/l (slow decomposition)6 g/L (20 ºC) |
| Flammpunkt | 305 °F (NTP, 1992)305 °F (152 °C) (Closed cup)329 °F (Open cup)305 °F (Closed cup)152 °C c.c. |
| Siedepunkt | 563 °F at 760 mmHg (sublimes) (NTP, 1992)285.3 °CSublimes below the boiling point284 °C (sublimes)295 °C @760 [mm Hg]284 °C(lit.) |
| Schmelzpunkt | 131-134 °C(lit.) |
| Dampfdichte | 5.1 (vs air) |
| Dampfdruck | <0.01 mm Hg ( 20 °C) |
| Brechungsindex | 1.4500 (estimate) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Flaky Crystals |
| pKa (Säurekonstante) | 2.97[at 20 ℃] |
| Farbe | White |
| pH | 2 (6g/l, H2O, 20℃) |
| Geruch | Characteristic choking odor |
| Explosionsgrenze | 1.7-10.5%(V) |
| Spezifische Wärmekapazität | Cp(crystal): 1.08 J/(g·K), at 25℃ |
| Merck | 14,7372 |
| BRN | 118515 |
| Henry-Konstante | 6.29 at 20 °C (approximate - calculated from water solubility and vapor pressure) |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents, strong bases, moisture, strong acids. Dust may form an explosive mixture with air. |
| InChI | 1S/C8H4O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4H |
| InChIKey | LGRFSURHDFAFJT-UHFFFAOYSA-N |
| SMILES | O=C1OC(=O)c2ccccc12 |
| LogP (Verteilungskoeffizient) | 2.07 at 20℃ |
| CAS Datenbank | 85-44-9(CAS DataBase Reference) |
| NIST chemische Informationen | Phthalic anhydride(85-44-9) |
| EPA chemische Informationen | Phthalic anhydride (85-44-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P333+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.4% (14 of 3919) of reports.H302 (99.6%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Chemical: 1,3-IsobenzofurandioneHazard Traits - DermatotoxicityRespiratory Toxicity1,3-Isobenzofurandione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Isobenzofurandione 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: 10-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15845Phthalic anhydride: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - 1,3-Isobenzofurandione: Human health tier II assessment |
| DOT-Kennzeichnung | Corrosive |
| Brandgefahren | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:· Combustible material: may burn but does not ignite readily.Combustible. Finely dispersed particles form explosive mixtures in air. |
| Brandpotenzial | Combustible solidCombustible when exposed to heat or flame. |
| Gesundheitsgefahren | Solid irritates skin and eyes, causing coughing and sneezing. Liquid causes severe thermal burns. (USCG, 1999)· TOXIC and/or CORROSIVEinhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. |
Anwendungen & Verwendung
Beschreibung
Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. This colourless solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. Phthalic anhydride is an important chemical intermediate in the plastics industry from which are derived numerous phthalate esters that function as plasticizers in synthetic resins. Phthalic anhydride itself is used as a monomer for synthetic resins such as glyptal, the alkyd resins, and the polyester resins. Phthalic anhydride is also used as a precursor of anthraquinone, phthalein, rhodamine, phthalocyanine, fluorescein, and xanthene dyes. Phthalic anhydride is used in the synthesis of primary amines, the agricultural fungicide phaltan, and thalidomide. Other reactions with phthalic anhydride yield phenolphthalein, benzoic acid, phthalylsulfathiazole (an intestinal antimicrobial agent), and orthophthalic acid.
Herstellung & Synthese
synthetische
The most important modifying component used in the manufacture of linear unsaturated polyesters is phthalic anhydride. The anhydride is generally obtained by the oxidation of o-xylene: The reaction is carried out in the vapour phase by passing a mixture of o-xylene and air over a catalyst such as vanadium pentoxide supported on silica and promoted with titanium dioxide at about 400C. The exit gases are cooled and the phthalic anhydride is collected and purified by distillation under reduced pressure.