Description
Dicyclohexylamine is a combustible, colorlessliquid with a faint amine odor. Molecular weight=181.36;Boiling point=256℃; Flash point $99℃. HazardIdentification (based on NFPA-704 M Rating System): Health3, Flammability 1, Reactivity 0. Slightly soluble in water.
Chemical Properties
Dicyclohexylamine is strongly basic with reactive amine groups which readily
form TV-substituted derivatives. It also forms salts with inorganic and organic
acids. Dicyclohexylamine will also form crystalline hydrates and alcoholates.
Uses
Dicyclohexylamine is manufactured by reacting equimolar
quantities of cyclohexanone and cyclohexylamine or cyclohexanone
and ammonia. It is used as a solvent and in
organic syntheses. It is reportedly used as a chemical
intermediate for the synthesis of corrosion inhibitors, rubber
vulcanization accelerators, textiles, and varnishes.
Uses
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.
Production Methods
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).
Definition
ChEBI: Dicyclohexylamine is a primary aliphatic amine.
Air & Water Reactions
Slightly soluble in water. May be sensitive to air.
Reactivity Profile
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.
Health Hazard
TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Health Hazard
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).
Fire Hazard
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.
Flammability and Explosibility
Non flammable
Industrial uses
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).
Safety Profile
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.
Potential Exposure
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
First aid
Skin Contact: Flood all areas of body thathave contacted the substance with water. Do not wait toremove contaminated clothing; do it under the water stream.Use soap to help assure removal. Isolate contaminatedclothing when removed to prevent contact by others.Eye Contact: Remove any contact lenses at once. Flusheyes well with copious quantities of water or normal salinefor at lest 20-30 min. Seek medical attention.
Metabolism
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.
storage
(1) Color Code—White: Corrosive or ContactHazard; Store separately in a corrosion-resistant location.(2) Color Code—Blue: Health Hazard/Poison: Store in asecure poison location. Prior to working with Di-Cha youshould be trained on its proper handling and storage. Storein tightly closed containers in a refrigerator away from oxidizers. Where possible, automatically pump liquid fromdrums or other storage containers to process containers.Protection from air is recommended for long-term storage.
Shipping
UN2565 Dicyclohexylamine, Hazard class: 8;
Labels: 8-Corrosive material
Incompatibilities
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
Waste Disposal
Incineration; incinerator
equipped with a scrubber or thermal unit to reduce nitrogen
oxides emissions.
