テレフタロイルクロリド
テレフタロイルクロリド · 1,4-ベンゼンジカルボン酸ジクロリド · ベンゼン-1,4-ジカルボン酸1,4-ジクロリド · テレフタロイルジクロリド · 1,4-ベンゼンジ(カルボニルクロリド) · 1,4-ビス(クロロホルミル)ベンゼン · p-フタロイルクロリド · p-フタル酸ジクロリド
識別子と物理属性
| CAS No. | 100-20-9 |
|---|---|
| 分子式 | C8H4Cl2O2 |
| 平均分子量 | 203.02 g/mol |
| 単同位体質量 | 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 |
| 現地名 | テレフタロイルクロリド |
化学・物理的性質
| XLogP | 4 |
|---|---|
| 極性表面積 | 34.1 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 2 |
| 重原子数 | 12 |
| 形式電荷 | 0 |
| 複雑度 | 173 |
| 物質分類 | Toxic Gases & Vapors -> Acid Halides |
| SpringerMaterials Properties | Boiling point |
| LogP（分配係数） | 0.88 (calculated) |
| 密度 | 1.32 g/cm³1,34 g/cm3 |
| Color/Form | COLORLESS NEEDLES |
| 溶解度 | SOLUBLE IN ETHERSolubility in water: reactionエタノール: 5%、透明反応する |
| 引火点 | 356 °F180 °C |
| 沸点 | 259 °C264 °C266 °C @760 [mm Hg]266 °C(lit.) |
| 融点 | 82-84 °C79.5-84 °C79-81 °C(lit.) |
| 蒸気圧 | 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. |
| 蒸気密度 | 7 (vs air) |
| 屈折率 | 1.5684 (estimate) |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | フレーク |
| 色 | White to Almost white |
| pH | <0.5 (H2O) |
| 爆発限界 | 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 データベース | 100-20-9(CAS DataBase Reference) |
| NISTの化学物質情報 | 1,4-Benzenedicarbonyl dichloride(100-20-9) |
| EPAの化学物質情報 | 1,4-Benzenedicarbonyl dichloride (100-20-9) |
化学的特性
monoclinic crystals or white crystalline flakes. Soluble in ethanol and organic solvents.
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | 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 |
| 火災危険 | Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| 有害性の概要 | 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. |
| 消火 | Use dry sand, powder, carbon dioxide. NO hydrous agents. |
| 応急処置措置 | 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 . |
| 安全保管 | Separated from strong oxidants. Dry. Well closed. Do NOT store or transport in containers made from metal. |
| 漏出処分 | 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. |
| 有害作用 | Dermatotoxin - Skin burns. |
| 暴露経路 | 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 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | WZ1797000 |
| 輸送番号（UN） | UN 2923 8/PG 3 |
| 税関コード | 29173980 |
| 危険文句（R） | 34-23-35 |
| 化審法 | (3)-1378 |
| 危険表示 | C,T |
| 安全措置（S） | 26-27-36/37/39-45-38-28B |
| 危険等級 | 6.1Acute Tox. 3 InhalationEye Dam. 1Skin Corr. 1ASTOT SE 3 |
| 包装等級 | II |
| 貯蔵分類 | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| 有害物質データ | 100-20-9(Hazardous Substances Data) |
用途
用途
芳香族ポリエステル等の耐熱ポリマ-原料アラミド繊維?合成樹脂?染料?顔料原料、紫外線吸収剤
使用
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.
一般的な説明
Terephthaloyl chloride undergoes condensation reaction with difunctional α,ω-diaminopolystyrene to yield chain-extended polystyrene containing amide bonds along the polymer backbone. It undergoes interfacial reaction with bovine serum albumin to form thin cross-linked films.
製法・合成法
製造方法
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.
純化方法
Crystallise the acid chloride from dry hexane. [Beilstein 9 IV 3318.]