Cyclohexylamine is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...

, belonging to the

aliphatic In organic chemistry, hydrocarbons ( compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (; G. ''aleiphar'', fat, oil). Aliphatic compounds can be saturated, like hexane, ...

amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen Hydrogen is the chemical element wi ...

class. It is a colorless liquid, although, like many amines, samples are often colored due to contaminants. It has a fishy odor and is miscible with water. Like other amines, it is a

weak base A weak base is a base that, upon dissolution in water, does not dissociate completely, so that the resulting aqueous solution contains only a small proportion of hydroxide ions and the concerned basic radical, and a large proportion of undissociat ...

, compared to strong bases such as

NaOH Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...

, but it is a stronger base than its

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

analog,

aniline Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starti ...

. It is a useful intermediate in the production of many other organic compounds (e.g.

cyclamate Cyclamate is an artificial sweetener. It is 30–50 times sweeter than sucrose (table sugar), making it the least potent of the commercially used artificial sweeteners. It is often used with other artificial sweeteners, especially saccharin; ...

)

Preparation

Cyclohexylamine is produced by two routes, the main one being the complete hydrogenation of

using some cobalt- or nickel-based catalysts: :C₆H₅NH₂ + 3 H₂ → C₆H₁₁NH₂ It is also prepared by

alkylation Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecti ...

of ammonia using

cyclohexanol Cyclohexanol is the organic compound with the formula HOCH(CH2)5. The molecule is related to cyclohexane by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid with a camphor-like odor, w ...

Applications

left, Cyclamate, a derivative of cyclohexylamine, is a popular artificial sweetener. Cyclohexylamine is used as an intermediate in synthesis of other organic compounds. It is the precursor to sulfenamide-based reagents used as accelerator (chemistry), accelerators for vulcanization. It is a building block for pharmaceuticals (e.g.,

mucolytic Mucoactive agents are a class of chemical agents that aid in the clearance of mucus or sputum from the upper and lower airways, including the lungs, bronchi, and trachea. Mucoactive drugs include expectorants, mucolytics, mucoregulators, and muco ...

s, analgesics, and

bronchodilator A bronchodilator or broncholytic (although the latter occasionally includes secretory inhibition as well) is a substance that dilates the bronchi and bronchioles, decreasing resistance in the respiratory airway and increasing airflow to the lung ...

s). The amine itself is an effective

corrosion inhibitor In chemistry, a corrosion inhibitor or anti-corrosive is a chemical compound that, when added to a liquid or gas, decreases the corrosion rate of a material, typically a metal or an alloy, that comes into contact with the fluid. The effectiveness ...

. The herbicide

hexazinone Hexazinone is an organic compound that is used as a broad spectrum herbicide. It is a colorless solid. It exhibits some solubility in water but is highly soluble in most organic solvents except alkanes. A member of the triazine class herbicides ...

and the anesthetic

hexylcaine Hexylcaine hydrochloride, also called cyclaine ( Merck) or osmocaine, is a short-acting local anesthetic. It acts by inhibiting sodium channel conduction. Overdose can lead to headache, tinnitus, numbness and tingling around the mouth and tongu ...

are derived from cyclohexylamine. It has been used as a flushing aid in the

printing ink Ink is a gel, sol, or solution that contains at least one colorant, such as a dye or pigment, and is used to color a surface to produce an image, text, or design. Ink is used for drawing or writing with a pen, brush, reed pen, or quill. Thicker ...

industry. {{Cite book , last = Apps , first = E. A. , title = Printing Ink Technology , publisher = Leonard Hill ooks/nowiki> Limited , year = 1958 , location = London , pages = ix , url =https://archive.org/details/printinginktechn00apps , url-access = registration

Toxicity

Cyclohexylamine has a low acute toxicity with LD₅₀ (rat; p.o.) = 0.71 ml/kg''The Merck Index, 10th Ed.'' (1983) p.392, Rahway: Merck & Co. Like other amines, it is corrosive. Cyclohexylamine is listed as an extremely hazardous substance as defined by Section 302 of the U.S.

Emergency Planning and Community Right-to-Know Act The Emergency Planning and Community Right-to-Know Act of 1986 is a United States federal law passed by the 99th United States Congress located at Title 42, Chapter 116 of the U.S. Code, concerned with emergency response preparedness. On October ...

. The

National Institute for Occupational Safety and Health The National Institute for Occupational Safety and Health (NIOSH, ) is the United States federal agency responsible for conducting research and making recommendations for the prevention of work-related injury and illness. NIOSH is part of the C ...

has suggested workers not be exposed to a

recommended exposure limit A recommended exposure limit (REL) is an occupational exposure limit that has been recommended by the United States National Institute for Occupational Safety and Health. The REL is a level that NIOSH believes would be protective of worker safet ...

of over 10 ppm (40 mg/m³) over an eight-hour workshift.

References

Amines Cyclohexyl compounds