ジシクロヘキシルアミン
1,1'-イミノビス(シクロヘキサン) · ビスシクロヘキシルアミン · N-シクロヘキシルシクロヘキシルアミン · イミノビス(シクロヘキサン) · N,N-ジシクロヘキシルアミン · ジシクロヘキシルアミン · N-シクロヘキシルシクロヘキサンアミン · N-シクロヘキシルシクロヘキサミン
識別子と物理属性
| CAS No. | 101-83-7 |
|---|---|
| 分子式 | C12H23N |
| 平均分子量 | 181.32 g/mol |
| 単同位体質量 | 181.18304974 g/mol |
| SMILES | C1CCC(NC2CCCCC2)CC1 |
| InChIKey | XBPCUCUWBYBCDP-UHFFFAOYSA-N |
| PubChem CID | 7582 |
| ChEMBL | CHEMBL1451838 |
| ChEBI | CHEBI:34694 |
| EC No. | 202-980-7 |
| DTXSID | DTXSID6025018 |
| 現地名 | ジシクロヘキシルアミン |
化学・物理的性質
| XLogP | 3.4 |
|---|---|
| 極性表面積 | 12 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 2 |
| 重原子数 | 13 |
| 形式電荷 | 0 |
| 複雑度 | 116 |
| 物質分類 | Nitrogen Compounds -> Amines, CyclicCorrosives |
| Polymers | Rubber |
| pH | STRONG BASE11 (1g/l, H2O, 20℃) |
| SpringerMaterials Properties | Boiling point |
| LogP（分配係数） | 3.5 |
| 臭い | FAINT FISHY ODORAmine odor.アミン臭 |
| 密度 | 0.913 to 0.919 at 59 °F (NTP, 1992)0.9104 at 25 °C/25 °CRelative density (water = 1): 0.90.912 g/mL at 20 °C(lit.) |
| Color/Form | COLORLESS LIQUID |
| 溶解度 | Slightly soluble (NTP, 1992)SPARINGLY SOL IN WATERSOL IN USUAL ORGANIC SOLVENTSMISCIBLE WITH CYCLOHEXYLAMINESoluble in ethanol, ether, benzene.Soluble in oxygenated solvents.Solubility in water, g/100ml at 25 °C: 0.08有機溶剤：可溶0.08 g/100mL (25 ºC) |
| 引火点 | greater than 210 °F (NTP, 1992)105 °C105 °C o.c.205 °F |
| 沸点 | 492.4 °F at 760 mmHg (NTP, 1992)255.8 °C @ 760 MM HG256 °C |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitrogen oxide/. |
| 融点 | -2 °C |
| 蒸気密度 | 6 (vs air) |
| 蒸気圧 | 12 mm Hg ( 37.7 °C) |
| 屈折率 | n20/D 1.4842(lit.) |
| 貯蔵条件 | Store below +30°C. |
| pKa（酸解離定数） | 10.4(at 25℃) |
| 外観・状態 | 無色の液体 |
| 色 | 無色 |
| 爆発限界 | 0.8-4.6%(V) |
| 凝固点 | -2℃ |
| Merck | 14,3095 |
| BRN | 605923 |
| ヘンリー定数 | 1.8×10-1 mol/(m3Pa) at 25℃, HSDB (2015) |
| 安定性 | 安定。強酸、強酸化剤とは相容れない。 |
| InChI | 1S/C12H23N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h11-13H,1-10H2 |
| InChIKey | XBPCUCUWBYBCDP-UHFFFAOYSA-N |
| SMILES | C1CCC(CC1)NC2CCCCC2 |
| LogP（分配係数） | 2.724 at 25℃ |
| CAS データベース | 101-83-7(CAS DataBase Reference) |
| NISTの化学物質情報 | Cyclohexanamine, N-cyclohexyl-(101-83-7) |
| EPAの化学物質情報 | Dicyclohexylamine (101-83-7) |
安全性と法規制
| GHS 分類 | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P260, P264, P270, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P391, P405, and P501 (click each P-code to see the statement)H302 (91.3%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P264, P264+P265, P270, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P391, P405, and P501 (click each P-code to see the statement) |
|---|---|
| 規制情報 | Chemical: Cyclohexanamine, N-cyclohexyl-Cyclohexanamine, N-cyclohexyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexanamine, N-cyclohexyl- 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: 06-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13263Dicyclohexylamine: 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.) |
| 輸送ラベル（DOT） | Corrosive |
| 火災危険 | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:· Combustible material: may burn but does not ignite readily.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| 火災の可能性 | COMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAMECAN REACT WITH OXIDIZING MATERIALS. |
| 健康有害性 | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:· TOXIC and/or CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death. |
| 有害性の概要 | A corrosive substance that can cause injury to the skin, eyes, and respiratory tractMay cause pulmonary edema[ICSC] Possible skin sensitizer[Merck Index] Toxic by ingestion, inhalation, and skin contact |
用途
解説
弱い魚臭をもつ液体。融点約 20℃，沸点 256℃ (一部分解) 。ジシクロヘキシルアミンは，水に溶けて強い塩基性を示す。エチルアルコール，ベンゼン，エーテルにも溶ける。アニリンの高圧還元によってシクロヘキシルアミンとともに生じる。ブリタニカ国際大百科事典 小項目事典 ブリタニカ
用途
有機合成原料。
用途
ゴム薬品、染料
用途
防錆剤?ゴム薬品?界面活性剤?染料原料
使用
Dicyclohexylamine (DCHA) is an aliphatic amine. As an intermediate, it can be used in a broad range of applications in different industries. Dicyclohexylamine is used as a vulcanization accelerator. In lubricants and cutting fluids it does function as a corrosion inhibitor. Here it should be mentioned that Dicyclohexylamine does not form Nitrosamines when being used. Reagent for preparation of crystalline amino acid derivative salts. Dicyclohexylamine was used to constitute ionic liquid matrices for bacterial analysis in matrix assisted laser desorption/ionisation mass spectrometry. It was used to develop a new palladium catalyst for Suzuki coupling reaction of aryl bromides with boronic acids. It was used as extractant in determination of gold(III) by dispersive liquid-liquid microextraction and electrothermal atomic absorption spectrometry.
使用用途
ジシクロヘキシルアミンの主な用途は、、ゴム薬品、エマルジョン系加工油等の原料、界面活性剤、染料原料、農薬などです。各種産業において幅広く用いられています。軟質ウレタンフォーム合成の際の触媒にも利用されます。 また、ジシクロヘキシルアミンは各種有機合成化学の中間原料としても有用な化合物です。具体的には、スルフェンアミド系加硫促進剤や、粘液溶解薬、鎮痛剤、気管支拡張薬などの医薬品などに使用されています。
製法・合成法
調製方法
Several methods are employed for the manufacture of dicyclohexylamine. It can be manufactured by hydrogenation of equimolar amounts of cyclohexanone and cyclohexylamine. Alternatively, dicyclohexylamine can be prepared by vapor phase catalytic hydrogenation of aniline at elevated temperature and pressure. Fractionation of the crude reaction product yields cyclohexylamine, unreacted aniline, and a high boiling residue comprised of N-phenylcyclohexylamine and dicyclohexylamine (Windholz et al 1983).