Dicyclohexylamine

Last updated
Dicyclohexylamine
Dicyclohexylamine 200.svg
Names
Preferred IUPAC name
N-Cyclohexylcyclohexanamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.710 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-980-7
PubChem CID
UNII
  • InChI=1S/C12H23N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h11-13H,1-10H2
    Key: XBPCUCUWBYBCDP-UHFFFAOYSA-N
  • C1CCC(CC1)NC2CCCCC2
Properties
C12H23N
Molar mass 181.323 g·mol−1
AppearancePale yellow liquid
Density 0.912 g/cm3
Melting point −0.1 °C (31.8 °F; 273.0 K)
Boiling point 255.8 °C (492.4 °F; 529.0 K)
0.8 g/L
Hazards
Lethal dose or concentration (LD, LC):
373 mg/kg (oral)[ clarification needed ]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dicyclohexylamine is a secondary amine with the chemical formula HN(C6H11)2. It is a colorless liquid, although commercial samples can appear yellow. It has a fishy odor, typical for amines. It is sparingly soluble in water. As an amine, it is an organic base and useful precursor to other chemicals. [1]

Contents

Synthesis

Dicyclohexylamine, as a mixture with cyclohexylamine, is prepared by the catalytic hydrogenation of aniline (phenylamine), with a catalyst of ruthenium and/or palladium. This method produces mainly cyclohexylamine with little dicyclohexylamine. Better results have been reported when the catalyst is applied to a support of niobic acid and/or tantalic acid. [2] It is also obtained by reductive amination of cyclohexanone with ammonia or cyclohexylamine. [1]

Dicyclohexylamine may also be prepared by pressure hydrogenation of diphenylamine using a ruthenium catalyst, or by the reaction of cyclohexanone with cyclohexylamine in the presence of a palladium/carbon catalyst under a hydrogen pressure of about 4 mm Hg. [2]

Applications

Dicyclohexylamine has applications that are similar to those of cyclohexylamine, namely the production of:

Related Research Articles

<span class="mw-page-title-main">Catalysis</span> Process of increasing the rate of a chemical reaction

Catalysis is the increase in rate of a chemical reaction due to an added substance known as a catalyst. Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quickly, very small amounts of catalyst often suffice; mixing, surface area, and temperature are important factors in reaction rate. Catalysts generally react with one or more reactants to form intermediates that subsequently give the final reaction product, in the process of regenerating the catalyst.

<span class="mw-page-title-main">Haber process</span> Industrial process for ammonia production

The Haber process, also called the Haber–Bosch process, is the main industrial procedure for the production of ammonia. The German chemists Fritz Haber and Carl Bosch developed it in the first decade of the 20th century. The process converts atmospheric nitrogen (N2) to ammonia (NH3) by a reaction with hydrogen (H2) using an iron metal catalyst under high temperatures and pressures. This reaction is slightly exothermic (i.e. it releases energy), meaning that the reaction is favoured at lower temperatures and higher pressures. It decreases entropy, complicating the process. Hydrogen is produced via steam reforming, followed by an iterative closed cycle to react hydrogen with nitrogen to produce ammonia.

<span class="mw-page-title-main">Ruthenium</span> Chemical element, symbol Ru and atomic number 44

Ruthenium is a chemical element; it has symbol Ru and atomic number 44. It is a rare transition metal belonging to the platinum group of the periodic table. Like the other metals of the platinum group, ruthenium is unreactive to most other chemicals. Karl Ernst Claus, a Russian-born scientist of Baltic-German ancestry, discovered the element in 1844 at Kazan State University and named ruthenium in honor of Russia. Ruthenium is usually found as a minor component of platinum ores; the annual production has risen from about 19 tonnes in 2009 to some 35.5 tonnes in 2017. Most ruthenium produced is used in wear-resistant electrical contacts and thick-film resistors. A minor application for ruthenium is in platinum alloys and as a chemistry catalyst. A new application of ruthenium is as the capping layer for extreme ultraviolet photomasks. Ruthenium is generally found in ores with the other platinum group metals in the Ural Mountains and in North and South America. Small but commercially important quantities are also found in pentlandite extracted from Sudbury, Ontario, and in pyroxenite deposits in South Africa.

<span class="mw-page-title-main">Hydrogenation</span> Chemical reaction between molecular hydrogen and another compound or element

Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically constitutes the addition of pairs of hydrogen atoms to a molecule, often an alkene. Catalysts are required for the reaction to be usable; non-catalytic hydrogenation takes place only at very high temperatures. Hydrogenation reduces double and triple bonds in hydrocarbons.

In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group. The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH3CH2C≡N is called "propionitrile". The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.

<span class="mw-page-title-main">Cyclohexanol</span> Chemical compound

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, which, when very pure, melts near room temperature. Millions of tonnes are produced annually, mainly as a precursor to nylon.

<span class="mw-page-title-main">Cyclohexanone</span> Chemical compound

Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has a sweet odor reminiscent of benzaldehyde. Over time, samples of cyclohexanone assume a pale yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Millions of tonnes are produced annually, mainly as a precursor to nylon.

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Adams' catalyst, also known as platinum dioxide, is usually represented as platinum(IV) oxide hydrate, PtO2•H2O. It is a catalyst for hydrogenation and hydrogenolysis in organic synthesis. This dark brown powder is commercially available. The oxide itself is not an active catalyst, but it becomes active after exposure to hydrogen whereupon it converts to platinum black, which is responsible for reactions.

<span class="mw-page-title-main">Palladium(II) acetate</span> Chemical compound

Palladium(II) acetate is a chemical compound of palladium described by the formula [Pd(O2CCH3)2]n, abbreviated [Pd(OAc)2]n. It is more reactive than the analogous platinum compound. Depending on the value of n, the compound is soluble in many organic solvents and is commonly used as a catalyst for organic reactions.

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<span class="mw-page-title-main">Hydrodesulfurization</span> Chemical process used to remove sulfur in natural gas and oil refining

Hydrodesulfurization (HDS), also called hydrotreatment or hydrotreating, is a catalytic chemical process widely used to remove sulfur (S) from natural gas and from refined petroleum products, such as gasoline or petrol, jet fuel, kerosene, diesel fuel, and fuel oils. The purpose of removing the sulfur, and creating products such as ultra-low-sulfur diesel, is to reduce the sulfur dioxide emissions that result from using those fuels in automotive vehicles, aircraft, railroad locomotives, ships, gas or oil burning power plants, residential and industrial furnaces, and other forms of fuel combustion.

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<span class="mw-page-title-main">Cyclohexylamine</span> Chemical compound

Cyclohexylamine is an organic compound, belonging to the aliphatic amine 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, compared to strong bases such as NaOH, but it is a stronger base than its aromatic analog, aniline.

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References

  1. 1 2 Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic". In Ullmann's Encyclopedia of Industrial Chemistry, 2000, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a02_001
  2. 1 2 U.S. Patent 5322965, "Process for the preparation of a mixture of cyclohexylamine and dicyclohexylamine using a supported noble metal catalyst", Bayer AG, 21 June 1994