ジシクロヘキシルアミン 化学特性,用途語,生産方法
外観
無色～わずかにうすい黄色, 澄明の液体
種類
ジシクロヘキシルアミンは、研究開発用試薬製品、及び工業用化学薬品として販売されています。研究開発用試薬製品としては、5g、100g、500g、2kg、25mL、500mLなどの容量の種類があります。通常室温で取り扱い可能な試薬製品です。有機合成原料などに用いられます。
工業用化学製品としては、16kg缶や180kgドラムなどで提供されている薬品です。ゴム薬、エマルジョン系加工油等の原料や防錆剤などの用途を想定されており、工場などで扱いやすい大容量で提供されます。
性質
ジシクロヘキシルアミンは、第二級アミンに分類されている有機化合物です。酸解離定数pKaは10.4であり、水溶液は強塩基性を示します。
通常の保管条件では安定と考えられる物質ですが、光により分解する可能性があります。高温、直射日光、熱、 炎、静電気などを避けることが必要です。また、強酸化剤とは反応するため、保管の際は混触を避けるべきです。
溶解性
水に難溶, アルコール, アセトンに可溶。エタノール及びアセトンに極めて溶けやすく、水にほとんど溶けない。
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
防錆剤?ゴム薬品?界面活性剤?染料原料
用途
ゴム薬品、染料
用途
有機合成原料。
合成
図1. ジシクロヘキシルアミンの合成例
ジシクロヘキシルアミンの主な製造法の1つは、ルテニウムやパラジウムを触媒としてを水素化する方法です。この方法では主生成物はシクロヘキシルアミンですが、副生成物として少量のジシクロヘキシルアミンを得ることが可能です。
なお、改良法では、ニオブ酸やタンタル酸を用いた報告があります。また、別法としては、アンモニアもしくはシクロヘキシルアミンを用いたシクロヘキサノンの還元的アミノ化反応が挙げられます。
その他の方法は、ルテニウム触媒存在下でのジフェニルアミンの加圧水素添加や、水素雰囲気下4mmHgの条件における、Pd/C触媒を用いたシクロヘキサノンとシクロヘキシルアミンの反応などです。
化学的特性
Dicyclohexylamine is a combustible, colorless
liquid with a faint amine odor.
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.
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).
一般的な説明
A colorless liquid with a faint fishlike odor. Less dense than water. May be toxic by ingestion. Severely irritates skin, eyes and mucous membranes. Used to make paints, varnishes and detergents.
空気と水の反応
Slightly soluble in water. May be sensitive to air.
反応プロフィール
DCHA reacts with oxidizing agents. Forms crystalline salts with many N-protected amino acids . Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
健康ハザード
Dicyclohexylamine is a strong irritant to skin and mucous membranes. Direct skin
contact with the liquid or vapor should be avoided. Its systemic effects in man
include nausea and vomiting, anxiety, restlessness and drowsiness. Individuals
repeatedly exposed to this chemical may develop sensitivity to it (HSDB 1988).
火災危険
Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
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。
法規制情報
ジシクロヘキシルアミンは、引火点100℃の引火性の物質です。消防法では「第4類危険物」「第三石油類水溶性液体」に指定されています。港則法では、「危険物・腐食性物質」に分類されています。法令を遵守し、正しく取り扱うことが必要です。
工業用途
Dicyclohexylamine is a widely used chemical intermediate. It can be used to
absorb acidic gases, to preserve rubber latex, to plasticize casein, and to neutralize
plant and insect poisons. Metal complexes of dicyclohexylamine are catalysts used
in the paint, varnish, and ink industries. Dicyclohexylamine salts of fatty acids and
sulfuric acid have soap and detergent properties used in the printing and textile
industries. One of the most important uses of dicyclohexylamine is as a vapor
phase corrosion inhibitor. It is used to protect packaged or stored ferrous metals
from atmospheric corrosion (Schweizer et al 1978).
安全性プロファイル
Poison by ingestion and
subcutaneous routes. Corrosive. A severe
skin and eye irritant. Questionable
carcinogen with experimental tumorigenic
data. Human mutation data reported.
Combustible when exposed to heat or
flame; can react with oxidizing materials. To
fight fue, use alcohol foam, CO2, dry
chemical. When heated to decomposition it
emits toxic fumes of NOx. See also
CYCLOHEXYLAMINE.
職業ばく露
Dicyclohexylamine salts of fatty acids
and sulfuric acid have soap and detergent properties useful
to the printing and textile industries. Metal complexes of
DI-CHA are used as catalysts in the paint, varnish, the ink
industries. Several vapor-phase corrosion inhibitors are
solid DI-CHA derivatives. These compounds are slightly
volatile at normal temperatures and are used to protect
packaged or stored ferrous metals from atmospheric corrosion. Dicyclohexylamine is also used for a number of other
purposes: plasticizers, insecticidal formulations; antioxidant
in lubricating oils, fuels, and rubber; and as an extractant.
Incompatibilities: Contact with strong oxidizers can cause
fire and explosion hazard
代謝
The extensive use of cyclamates as artificial sweeteners a number of years ago led
to extensive study on the metabolism and carcinogenicity of cyclohexylamine, a
metabolic product of cyclamate. However, there is little such information available
concerning dicyclohexylamine. Filov (1968) investigated the metabolism of
cyclohexylamine and dicyclohexylamine. Both amines were readily absorbed
from the gastro-intestinal tract. In addition, they rapidly entered the bloodstream
following inhalation and penetrated intact skin. In rats, it was determined that
26-44% of dicyclohexylamine present in the stomach was eliminated unchanged,
mostly in the urine. The clearance rate of the amines was also quite high,
particularly for dicyclohexylamine.
輸送方法
UN2565 Dicyclohexylamine, Hazard class: 8;
Labels: 8-Corrosive material
不和合性
Dicyclohexylamine salts of fatty acids
and sulfuric acid have soap and detergent properties useful
to the printing and textile industries. Metal complexes of
DI-CHA are used as catalysts in the paint, varnish, the ink
industries. Several vapor-phase corrosion inhibitors are
solid DI-CHA derivatives. These compounds are slightly
volatile at normal temperatures and are used to protect
packaged or stored ferrous metals from atmospheric corrosion. Dicyclohexylamine is also used for a number of other
purposes: plasticizers, insecticidal formulations; antioxidant
in lubricating oils, fuels, and rubber; and as an extractant.
Incompatibilities: Contact with strong oxidizers can cause
fire and explosion hazard
廃棄物の処理
Incineration; incinerator
equipped with a scrubber or thermal unit to reduce nitrogen
oxides emissions.
ジシクロヘキシルアミン 上流と下流の製品情報
原材料
準備製品