セバシン酸
セバシン酸 · オクタン-1,8-ジカルボン酸 · デカン二酸 · 1,8-オクタンジカルボン酸 · 1，8-オクタン-ジ-カルボン酸［別名：セバシン酸］ · セバシン酸, 98+% · DECANEDIOIC ACID · sebacic
識別子と物理属性
| CAS No. | 111-20-6 |
|---|---|
| 分子式 | C10H18O4 |
| 平均分子量 | 202.25 g/mol |
| 単同位体質量 | 202.12050906 g/mol |
| SMILES | O=C(O)CCCCCCCCC(=O)O |
| InChIKey | CXMXRPHRNRROMY-UHFFFAOYSA-N |
| PubChem CID | 5192 |
| ChEMBL | CHEMBL1232164 |
| ChEBI | CHEBI:41865 |
| EC No. | 203-845-5 |
| DTXSID | DTXSID7026867 |
| 現地名 | セバシン酸 |
化学・物理的性質
| XLogP | 2.1 |
|---|---|
| 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 | 9 |
| 重原子数 | 14 |
| 形式電荷 | 0 |
| 複雑度 | 157 |
| 物質分類 | Other Classes -> Organic Acids |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| 脂質 | Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117] |
| 化粧品 | Cosmetic ingredients (Sebacic Acid) -> CIR (Cosmetic Ingredient Review)Buffering |
| SpringerMaterials Properties | Boiling point |
| 農薬 | RepellantsActive substance -> EU Pesticides database: Not approved |
| LogP（分配係数） | 2.2 |
| 密度 | 1.2075 at 68 °F (NTP, 1992) - Denser than waterwill sink1.2 g/cm³1.21 |
| 溶解度 | less than 1 mg/mL at 70 °F (NTP, 1992)1.0 mg/mLSolubility in water, g/100ml: 0.1 (poor)エタノール：100mg/mL1g/L（20℃） |
| 引火点 | 220 °C |
| 沸点 | 563 °F at 100 mmHg (NTP, 1992)364.00 to 365.00 °C. @ 760.00 mm Hgat 13.3kPa: 294 °C294.5 °C/100 mmHg (lit.) |
| 融点 | 274.1 °F (NTP, 1992)130.8 °C131 °C133-137 °C (lit.) |
| 蒸気圧 | 1 mm Hg ( 183 °C) |
| 屈折率 | 1.422 |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 粉末または顆粒 |
| pKa（酸解離定数） | 4.59, 5.59(at 25℃) |
| 色 | ホワイトからオフホワイト |
| 臭い | 単斜晶系角型錠剤、白色粉末、脂肪酸臭 |
| Merck | 14,8415 |
| BRN | 1210591 |
| ヘンリー定数 | 7.6×107 mol/(m3Pa) at 25℃, Compernolle and Müller (2014) |
| 安定性 | 安定。可燃性。強力な酸化剤、塩基、還元剤とは相容れない。 |
| 化粧品成分の機能 | バッファリング |
| InChI | 1S/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14) |
| InChIKey | CXMXRPHRNRROMY-UHFFFAOYSA-N |
| SMILES | OC(=O)CCCCCCCCC(O)=O |
| LogP（分配係数） | 1.5 at 23℃ |
| CAS データベース | 111-20-6(CAS DataBase Reference) |
| NISTの化学物質情報 | Decanedioic acid(111-20-6) |
| EPAの化学物質情報 | Sebacic acid (111-20-6) |
化学的特性
White flaky crystals. Slightly soluble in water, soluble in alcohol and ether.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 99.5% (2752 of 2766) of all reports.Not ClassifiedAggregated GHS information provided per 2766 reports by companies from 9 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | Chemical: Decanedioic acidDecanedioic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Decanedioic 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)2004/129/ECStatus: Active Update: 23-04-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/29447Decanedioic acid: Non hazardous |
| その他の安全情報 | IMAP assessments - Decanedioic acid: Human health tier I assessment |
| 火災危険 | Flash point data for this compound are not available. It is probably combustible. (NTP, 1992)Combustible. Finely dispersed particles form explosive mixtures in air. |
| 健康有害性 | SYMPTOMS: This compound may cause irritation. |
| 有害性の概要 | Causes somnolence, excitement, and effects on food intake in oral lethal-dose studies of ratsCauses impaired liver function tests and effects on CNS in repeated-dose inhalation studies of rats[RTECS] No listed effects of short-term or long-term exposure (health effects not fully investigated)[ICSC] May cause irritation[NTP] May cause irritation[Acros Organics MSDS] |
| 反応性グループ | Acids, Carboxylic |
| Reactivity Profile | SEBACIC ACID reacts exothermically to neutralize bases, both organic and inorganic. May react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Can react with active metals to form gaseous hydrogen and a metal salt. Such reactions are slow in the dry, but systems may absorb enough water from the air to allow corrosion of iron, steel, and aluminum parts and containers. Reacts slowly with cyanide salts to generate gaseous hydrogen cyanide. Reacts with solutions of cyanides to cause the release of gaseous hydrogen cyanide. May generate flammable and/or toxic gases and heat with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. May react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Can be oxidized exothermically by strong oxidizing agents and reduced by strong reducing agents. May initiate polymerization reactions. |
用途
解説
セバシン酸無色の葉状結晶．融点134.5 ℃，沸点294.5 ℃(13.3 kPa)，232 ℃(1.33 kPa)．d420"1.422．エタノール，エーテルに易溶，水に難溶．アルキド樹脂，ポリアミドの製造原料，また，ろうそくや香料の原料にも用いられる．
用途
可塑剤、アルキド樹脂、ポリアミド、潤滑油、ペイント、ロウソク、香料の原料。
説明
Sebacic acid is a dicarboxylic acid with structure (HOOC)(CH2)8(COOH), and is naturally occurring. In its pure state it is a white flake or powdered crystal. The product is described as non-hazardous, though in its powdered form it can be prone to flash ignition (a typical risk in handling fine organic powders). Sebaceus is Latin for tallow candle, sebum (tallow) is Latin for tallow, and refers to its use in the manufacture of candles. Sebacic acid is a derivative of castor oil, with the vast majority of world production occurring in China which annually exports over 20,000 metric tonnes, representing over 90 % of global trade of the product. In the industrial setting, sebacic acid and its homologues such as azelaic acid can be used in plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. Sebacic acid is also used as an intermediate for aromatics, antiseptics, and painting materials.
使用
Decanedioic acid was named by Thenard LJ (1802) from the Latin sebaceus(tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles. Thenard LJ isolated this compound from distillation products of beef tallow. In 1954, it was reported that it was produced in excess of 10,000 tons annually by alkali fission of castor oil. Sebacic acid and its derivatives, as azelaic acid, have a variety of industrial uses as plasticizers, lubricants, diffusion pump oils, cosmetics, candles, etc. It is also used in the synthesis of polyamide, as nylon, and of alkyd resins. An isomer, isosebacic acid, has several applications in the manufacture of vinyl resin plasticizers, extrusion plastics, adhesives, ester lubricants, polyesters, polyurethane resins and synthetic rubber.
一般的な説明
White granular powder. Melting point 153°F. Slightly soluble in water. Sublimes slowly at 750 mm Hg when heated to melting point.
製法・合成法
製造方法
Sebacic acid is normally made from castor oil, which is essentially glycerol triricinoleate. The castor oil is heated with sodium hydroxide at about 250e. This treatment results in saponification of the castor oil to ricinoleic acid which is then cleaved to give 2-octanol and sebacic acid: This process results in low yields of sebacic acid (about 50% based on the castor oil) but, nevertheless, other routes have not proved competitive. Sebacic acid is a colourless crystalline solid, m.p. 134.
純化方法
Purify sebacic acid via the disodium salt which, after crystallisation from boiling water (charcoal), is again converted to the free acid. The free acid is crystallised repeatedly from hot distilled water or from Me2CO/pet ether and dried under vacuum. [Beilstein 2 IV 2078.]