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Terephtaloyldichlorid
TCL · TEREPHTHALOYL DICHLORIDE · Terephtaloyl chloride · bis(forMaldehyde) · P-PHTHALOYL CHLORIDE · TEREPHTHALIC ACID DICHLORIDE · 1,4-Benzenedicarbonyl dichloride · TEREPHTHALYL CHLORIDE
Identifikatoren & physikalische Daten
| CAS No. | 100-20-9 |
|---|---|
| Summenformel | C8H4Cl2O2 |
| Durchschnittliche Molmasse | 203,02 g/mol |
| Monoisotopische Masse | 201,95883473 g/mol |
| SMILES | O=C(Cl)c1ccc(C(=O)Cl)cc1 |
| InChIKey | LXEJRKJRKIFVNY-UHFFFAOYSA-N |
| PubChem CID | 7488 |
| ChEMBL | CHEMBL1893301 |
| EC No. | 202-829-5 |
| DTXSID | DTXSID7026653 |
| Lokaler Name | Terephtaloyldichlorid |
Chemische & physikalische Eigenschaften
| XLogP | 4 |
|---|---|
| Polarare Oberfläche (TPSA) | 34,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 173 |
| Stoffklassen | Toxic Gases & Vapors -> Acid Halides |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | 0.88 (calculated) |
| Dichte | 1.32 g/cm³1,34 g/cm3 |
| Color/Form | COLORLESS NEEDLES |
| Löslichkeit | SOLUBLE IN ETHERSolubility in water: reactionethanol: 5%, clearREACTS |
| Flammpunkt | 356 °F180 °C |
| Siedepunkt | 259 °C264 °C266 °C @760 [mm Hg]266 °C(lit.) |
| Schmelzpunkt | 82-84 °C79.5-84 °C79-81 °C(lit.) |
| Dampfdruck | Vapor pressure, Pa at 20 °C: 3200.02 mm Hg ( 25 °C) |
| Food Contact Substances | FCS -> FDA Cumulative Estimated Daily Intake (CEDI)FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFRFCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications |
| Physical Description | Large CrystalsDry PowderColorless or white solid with pungent odor[ICSC] White flakes[MSDSonline]WHITE POWDER OR COLOURLESS NEEDLES WITH PUNGENT ODOUR. |
| Dampfdichte | 7 (vs air) |
| Brechungsindex | 1.5684 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | flakes |
| Farbe | White to Almost white |
| pH | <0.5 (H2O) |
| Explosionsgrenze | 1.5-8.9%(V) |
| BRN | 607796 |
| InChI | 1S/C8H4Cl2O2/c9-7(11)5-1-2-6(4-3-5)8(10)12/h1-4H |
| InChIKey | LXEJRKJRKIFVNY-UHFFFAOYSA-N |
| SMILES | ClC(=O)c1ccc(cc1)C(Cl)=O |
| CAS Datenbank | 100-20-9(CAS DataBase Reference) |
| NIST chemische Informationen | 1,4-Benzenedicarbonyl dichloride(100-20-9) |
| EPA chemische Informationen | 1,4-Benzenedicarbonyl dichloride (100-20-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 88.7% (2008 of 2263) of all reports.DangerH314 (11.2%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]P260, P261, P264, P271, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2263 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 1,4-Benzenedicarbonyl dichloride1,4-Benzenedicarbonyl dichloride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Benzenedicarbonyl dichloride 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: 29-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13172Terephthaloyl dichloride: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| Gefahrenübersicht | A reproductive effectorCauses asphyxiation by upper airway obstruction after lethal-dose inhalation studies of mice[RTECS] Dust/air mixture may be explosiveReacts with water producing hydrogen chlorideA corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation may cause upper airway edema and pulmonary edema[ICSC] A skin irritant[HSDB] Reacts with waterA lachrymatorInhalation may cause chemical pneumonitisEffects in high-dose animal studies include lacrimation, changes in renal tubules and other changes to the brain[MSDSonline] |
| Chemical Dangers | Decomposes on heating. This produces toxic and corrosive fumes. Reacts with strong oxidants. Reacts with water. This produces hydrogen chloride (see ICSC 0163). Attacks many metals in the presence of water. |
| Physical Dangers | Dust explosion possible if in powder or granular form, mixed with air. |
| Hazard Classes and Categories | Skin Corr. 1A (11.2%)Skin corrosion/irritation - Category 1 |
| Skin, Eye, and Respiratory Irritations | SKIN IRRITANT. |
| Brandbekämpfung | Use dry sand, powder, carbon dioxide. NO hydrous agents. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Half-upright position. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .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. Do NOT induce vomiting. Refer for medical attention . |
| Sichere Lagerung | Separated from strong oxidants. Dry. Well closed. Do NOT store or transport in containers made from metal. |
| Verschüttetes entsorgen | Personal protection: chemical protection suit and particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered plastic containers. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Eye Prevention | Wear safety goggles or eye protection in combination with breathing protection. |
| Fire Prevention | NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust. |
| Inhalation Risk | A harmful concentration of airborne particles can be reached quickly when dispersed. |
| Skin Prevention | Protective clothing. Protective gloves. |
| Exposure Prevention | PREVENT DISPERSION OF DUST! |
| Ingestion Prevention | Do not eat, drink, or smoke during work. |
| Inhalation Prevention | Use local exhaust or breathing protection. |
| Effects of Short Term Exposure | The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Exposure could cause asphyxiation due to swelling in the throat. Inhalation may cause lung oedema. |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| Expositionspfade | Serious by all routes of exposure. |
| Signs and Symptoms | Cough. Sore throat. Burning sensation. Laboured breathing. Shortness of breath. Symptoms may be delayed.Redness. Pain. Skin burns.Redness. Pain. Blurred vision. Severe deep burns.Abdominal pain. Nausea. Vomiting. Diarrhoea. Shock or collapse. |
| Toxicity Data | LC50 (rat) = 700 mg/m3/4h |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2923 8/PG 3 |
| Zollcode | 29173980 |
| RTECS-Nr. | WZ1797000 |
| R-Sätze (R) | 34-23-35 |
| Gefahrensymbole | C,T |
| Sicherheitshinweise (S) | 26-27-36/37/39-45-38-28B |
| Gefahrenklasse | 6.1Acute Tox. 3 InhalationEye Dam. 1Skin Corr. 1ASTOT SE 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Gefahrstoffdaten | 100-20-9(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Terephthaloyl chloride acts as a monomer with p-phenylenediamine used in the preparation of polymer viz. poly paraphenylene terephthalamide. It is an active component in performance polymers and aramid fibers, which gives flame resistance, chemical resistance, temperature stability, light weight, and very high strength. It is also used as an effective water scavenger, utilized to stabilize isocyanates and urethane prepolymers. Further, it is used in the preparation of liquid crystalline thermosets by thermal cyclotrimerization of dicyanate compounds of ring substituted bis(4-hydroxyphenyl) terepthalates. In addition to this, it is involved in the condensation reaction with difunctional alfa, μ-diaminopolystyrene to get chain-extended polystyrene containing amide bonds along the polymer backbone.
Herstellung & Synthese
synthetische
Synthesis of terephthaloyl chloride by thionyl chloride method: terephthalic acid is mixed with thionyl chloride, refluxed at 80℃ for 10-12h, then the thionyl chloride is evaporated, and the resulting crude product is distilled under reduced pressure to obtain the finished product.