テレフタル酸
テレフタル酸 · 1,4-ベンゼンジカルボン酸 · p-フタル酸 · ベンゼン-1,4-ジカルボン酸 · テレフタル酸標準品 · ECAMSULE RELATED COMPOUND C (テレフタル酸) · テレフタル酸, 98+% · テレフタラート
識別子と物理属性
| CAS No. | 100-21-0 |
|---|---|
| 分子式 | C8H6O4 |
| 平均分子量 | 166.13 g/mol |
| 単同位体質量 | 166.02660867 g/mol |
| SMILES | O=C(O)c1ccc(C(=O)O)cc1 |
| InChIKey | KKEYFWRCBNTPAC-UHFFFAOYSA-N |
| PubChem CID | 7489 |
| ChEMBL | CHEMBL1374420 |
| ChEBI | CHEBI:15702 |
| EC No. | 202-830-0 |
| DTXSID | DTXSID6026080 |
| 現地名 | テレフタル酸 |
化学・物理的性質
| XLogP | 2 |
|---|---|
| 極性表面積 | 74.6 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 2 |
| 重原子数 | 12 |
| 形式電荷 | 0 |
| 複雑度 | 169 |
| 物質分類 | Other Classes -> Organic Acids |
| 農薬 | Environmental transformation -> Pesticide transformation products (metabolite, successor) |
| LogP（分配係数） | log Kow = 2.001.961.68 |
| 密度 | 1.51 (NTP, 1992) - Denser than waterwill sinkSpecific gravity = 1.522 at 25 °CRelative density (water = 1): 1.511.51 @25 °C1.58 g/cm3 at 25 °C |
| Color/Form | NeedlesWhite crystals or powder |
| 溶解度 | Insoluble (NTP, 1992)Insoluble in chloroform, ether, acetic acidslightly soluble in alcoholsoluble in alkaliesSolubilities at 25 °C (g/100 g solvent): water = 0.0017, glacial acetic acid = 0.013, methanol = 0.1, dimethylformamide = 6.7, dimethyl sulfoxide = 19.0In water, 15 mg/L at 20 °C0.015 mg/mL at 20 °CSolubility in water, g/100ml at 20 °C: 0.2815mg/l (実験的)水にわずかに溶ける (25°C で 0.017 g/L) |
| 引火点 | 260 °C500 °F (260 °C) (Open cup)260°C |
| 沸点 | greater than 572 °F at 760 mmHg (sublimes without melting) (NTP, 1992)>572 °F (sublimes)214.32°C (rough estimate) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| 融点 | Sublimes (NTP, 1992)427 °C (sealed tube)> 300 °C>300 °C (lit.) |
| 蒸気圧 | 0.0000092 [mmHg]Vapor pressure: 1.3 kPa at 303 °C13.3 kPa at 353 °C26.7 kPa at 370 °C53.3 kPa at 387 °C101.3 kPa at 404 °CVapor pressure = 0.097 kPa at 250 °C6X10-11 mm Hg at 25 °C /Antoine extrapolation from higher temperatures/Vapor pressure, Pa at 20 °C:<0.01 mm Hg ( 20 °C) |
| Food Contact Substances | FCS -> FDA Cumulative Estimated Daily Intake (CEDI)FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR |
| 屈折率 | 1.5100 (estimate) |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 外観・状態 | 結晶性粉末 |
| pKa（酸解離定数） | 3.51(at 25℃) |
| 色 | 白い |
| pH | 3.36(1 mM solution)2.79(10 mM solution)2.26(100 mM solution) |
| Merck | 14,9162 |
| BRN | 1909333 |
| ヘンリー定数 | 2.5×107 mol/(m3Pa) at 25℃, HSDB (2015) |
| 誘電率 | 1.5(Ambient) |
| 安定性 | 安定。可燃性。強力な酸化剤とは相容れない。 |
| InChI | 1S/C8H6O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H,9,10)(H,11,12) |
| InChIKey | KKEYFWRCBNTPAC-UHFFFAOYSA-N |
| SMILES | OC(=O)c1ccc(cc1)C(O)=O |
| LogP（分配係数） | 2 at 25℃ |
| CAS データベース | 100-21-0(CAS DataBase Reference) |
| EPAの化学物質情報 | Terephthalic acid (100-21-0) |
化学的特性
Terephthalic acid is a white crystalline solid. Soluble in alkaline solution, slightly soluble in hot ethanol, insoluble in water, ether, glacial acetic acid and chloroform, consequently up until around 1970 most crude terephthalic acid was converted to the dimethyl ester for purification. It sublimates when heated.
化学性质
色の针状結晶。酸性を持ち、アミン類と酰胺類と反応する。
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 82.5% (1040 of 1260) of all reports.WarningH315 (17.4%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1260 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Not Classified |
|---|---|
| 規制情報 | Chemical: 1,4-Benzenedicarboxylic acidRegulation (EC) No 1935/2004 (amended)1,4-Benzenedicarboxylic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Benzenedicarboxylic acid 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)TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.Status: Active Update: 15-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15563Terephthalic acid: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | IMAP assessments - 1,4-Benzenedicarboxylic acid: Human health tier I assessment |
| 火災危険 | Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)Combustible. Finely dispersed particles form explosive mixtures in air. |
| 火災の可能性 | Combustible |
| 健康有害性 | SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin and eyes. |
| 有害性の概要 | Practically nontoxic in acute, high-dose animal studiesIn high-dose feeding studies in rats, it causes bladder stones and subsequent bladder cancersThe bladder cancers are thought to be secondary to the presence of bladder stones. [ACGIH] A skin and eye irritant[ICSC] An irritantEffects in high-dose animal studies include abnormal liver function tests[MSDSonline] |
用途
解説
芳香族ジカルボン酸の一つ。テレフタル酸は，1,4-ベンゼンジカルボン酸ともよばれる。フタル酸（1,2-ベンゼンジカルボン酸）およびイソフタル酸（1,3-ベンゼンジカルボン酸）はテレフタル酸の異性体である。実験室的には、p(パラ)-キシレンを過マンガン酸カリウム、三酸化クロムなどにより酸化すると得られる。以前は、フタル酸または安息香酸のカリウム塩を二酸化炭素と加圧・加熱するヘンケル法（ドイツのヘンケル社Henkel & Cieが開発）により工業的に製造されていたが、今日では、コバルトなどの重金属触媒を用いるp-キシレンの空気酸化により製造されている。常圧では300℃付近で昇華する。白色の結晶で、水、エタノール（エチルアルコール）にはほとんど溶けず、ベンゼン、エーテルにも溶けないが、アルカリ水溶液には塩を生成して溶解する。テレフタル酸とグリコールのポリエステル（ポリエチレンテレフタレート、PET）は、日本では「テトロン」の商品名で知られ、合成繊維として多量に生産されているほかに、飲料容器用の合成樹脂（ペットボトル）として広く用いられている。また、1価の脂肪族アルコールとのエステルはプラスチックの可塑剤として用いられている。
用途
合成樹脂原料、塗料原料
用途
ポリエステル系合繊(テトロン)、テトロンフィルム、エンプラ(ポリアリレート)の原料
説明
Terephthalic acid is the organic compound with formula C6H4(COOH)2. This colourless solid is a commodity chemical, used principally as a precursor to the polyester PET, used to make clothing and plastic bottles. Several million tones are produced annually. It is one of three isomeric phthalic acids.
来歴
Terephthalic acid came to prominence through the work of Winfield and Dickson in Britain around 1940. Earlier work by Carothers and coworkers in the United States established the feasibility of producing high molecular weight linear polyesters by reacting diacids with diols, but they used aliphatic diacids and diols. These made polyesters which were unsuitable to be spun into fibers. Winfield and Dickson found that symmetrical aromatic diacids yield high-melting, crystalline, and fiberforming materials; poly(ethylene terephthalate) (PET) has since become the largest volume synthetic fiber.
使用
Terephthalic acid (TPA) is a benzenepolycarboxylic acid with potential anti-hemorrhagic properties. It is a high-tonnage chemical, widely used in the production of synthetic materials, notably polyester fibers (poly-(ethylene terephthalate)).
一般的な説明
White powder.
使用用途
テレフタル酸は、化学繊維の中で最も多く使用されているポリエステル繊維、各種工業製品で基盤フィルムと使用されるPET () 樹脂、および飲料容器として幅広く用いられているPETボトルの原料に利用されています。 化学品中間物、有機化学製品 (合成繊維、合成樹脂) 、ポリエステル系合繊 (テトロン) 、テトロンフィルム (ルミラー、ダイテフォイル) 、ボトルエンプラ (ポリアリレート) の原料にも有用です。その他、医療用のステントや人工心臓弁などの機械部品、染料、顔料、農薬の原料などにも利用されます。
製法・合成法
調製方法
Terephthalic acid is produced by oxidation of p-xylene by oxygen in air: This reaction proceeds through a p-toluic acid intermediate which is then oxidized to terephthalic acid. In p-toluic acid, deactivation of the methyl by the electron withdrawing carboxylic acid group makes the methyl one tenth as reactive as xylene itself, making the second oxidation significantly more difficult . The commercial process utilizes acetic acid as solvent and a catalyst composed of cobalt and manganese salts, with a bromide promoter.
製造方法
The major commercial route to terephthalic acid which is suitable for the direct preparation of poly(ethylene terephthalate) is from p-xylene: p-Xylene is obtained largely from petroleum sources, being a product of the fractionation of reformed naphthas. The oxidation is carried out in the liquid phase. Typically, air is passed into a solution of p-xylene in acetic acid at about 200 and 2 MPa (20 atmospheres) in the presence of a catalyst system containing cobalt and manganese salts and a source of bromide ions. The terephthalic acid produced contains only small amounts of impurities (mainly p-carboxybenzaldehyde), which are readily removed. The acid is dissolved in water at about 2500 e and 5 MPa (50 atmospheres) and treated with hydrogen (which converts the aldehyde to p-toluic acid). The solution is then cooled to 100 and pure terephthalic acid crystallizes.
合成方法
石油系の中間生成物、例えば對二甲苯を酸化する方法で合成される。
純化方法
Purify the acid via the sodium salt which, after crystallisation from water, is re-converted to the acid by acidification with mineral acid. Filter off the solid, wash it with H2O and dry it in a vacuum. The S-benzylisothiuronium salt has m 204o (from aqueous EtOH). [Beilstein 9 IV 3301.]