Dicyclohexylamine

Base Information

• Chemical Name: Dicyclohexylamine
• CAS No.: 101-83-7
• Deprecated CAS: 111487-88-8,111487-93-5,111522-94-2,157973-63-2,856793-27-6,878781-89-6,111487-93-5,111522-94-2,856793-27-6
• Molecular Formula: C12H23N
• Molecular Weight: 181.321
• Hs Code.: 29213000
• European Community (EC) Number: 202-980-7,464-070-8
• ICSC Number: 1339
• NSC Number: 3399
• UN Number: 2565
• UNII: 1A93RJW924
• DSSTox Substance ID: DTXSID6025018
• Nikkaji Number: J4.018E
• Wikipedia: Dicyclohexylamine
• Wikidata: Q425368
• Metabolomics Workbench ID: 78516
• ChEMBL ID: CHEMBL1451838
• Mol file: 101-83-7.mol

Synonyms:cyclohexanamine, N-cyclohexyl-, sulfate (1:1);dicyclohexylamine;dicyclohexylamine hydrochloride;dicyclohexylamine nitrate;dicyclohexylamine nitrite;dicyclohexylamine phosphate (3:1);dicyclohexylamine sulfate;dicyclohexylamine sulfate (1:1);dicyclohexylammonium

Chemical Property of Dicyclohexylamine

Chemical Property:

• Appearance/Colour: Colorless liquid
• Vapor Pressure: 12 mm Hg ( 37.7 °C)
• Melting Point: -2 °C
• Refractive Index: 1.4842
• Boiling Point: 256.1 °C at 760 mmHg
• PKA: 10.4(at 25℃)
• Flash Point: 96.1 °C
• PSA: 12.03000
• Density: 0.912 g/cm³
• LogP: 3.63230
• Storage Temp.: Store at RT.
• Sensitive.: Air Sensitive
• Solubility.: organic solvents: soluble
• Water Solubility.: 1 g/L (20 ºC)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 181.183049738
• Heavy Atom Count: 13
• Complexity: 116
• Transport DOT Label: Corrosive

Purity/Quality:

99% ^*data from raw suppliers

Dicyclohexylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,N
• Hazard Codes: C,N
• Statements: 22-34-50/53-24/25
• Safety Statements: 26-36/37/39-45-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Cyclic
• Canonical SMILES: C1CCC(CC1)NC2CCCCC2
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Inhalation of the vapour may cause lung oedema. The effects may be delayed. Medical observation is indicated.
• 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. 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. Industrial solvent; corrosion inhibitor.

Technology Process of Dicyclohexylamine

There total 238 articles about Dicyclohexylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.4%

aniline (62-53-3) → N-phenyl-2-cyclohexylamine (1821-36-9) + cyclohexylamine (108-91-8,157973-60-9) + N-cyclohexyl-cyclohexanamine (101-83-7)

Guidance literature:

aluminum oxide; ruthenium; at 170 ℃; for 2.5h; Product distribution; Mechanism; investigation of the hydrogenation of aniline with various hydrogenation catalysts in the presence and abscence of the fused salts;

Reference yield: 24.0%

nitrobenzene (98-95-3,26969-40-4) → N-phenyl-2-cyclohexylamine (1821-36-9) + N-cyclohexyl-cyclohexanamine (101-83-7)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In hexane; at 30 ℃; for 18h; under 7500.75 Torr; Catalytic behavior;

DOI:10.1039/c3cc47693f

Reference yield: 12.0%

diphenylamine (122-39-4) → N-phenyl-2-cyclohexylamine (1821-36-9) + N-cyclohexyl-cyclohexanamine (101-83-7)

Guidance literature:

With octylated silica; hydrogen; sodium 4-dodecylbenzenesulfonate; {[(CH₃)(C₈H₁₇)3N](+)[RhCl₄](-)}; at 80 ℃; for 17h; under 10343 Torr;

DOI:10.1002/chem.200305591

upstream raw materials:

cyclohexanone-oxime

N,N-diphenylaminobenzene

cyclohexanone N-cyclohexylimine

ammonium formate

Downstream raw materials:

2-dicyclohexylamino-ethanol

quinoline-2-carboxylic acid dicyclohexylamide

ethyl dicyclohexylcarbamate

N,N-dicyclohexyl-salicylamide

Refernces

• 1、 Wang, Lyu-Ming,Kobayashi, Kensuke,Arisawa, Mitsuhiro,Saito, Susumu,Naka, Hiroshi. "Pd/TiO2-Photocatalyzed Self-Condensation of Primary Amines to Afford Secondary Amines at Ambient Temperature". . p. 341 - 344. Retrieved 2019.
• 2、 Rathod, Vikas Damu,Paganelli, Stefano,Piccolo, Oreste. "Selective reduction of halo-nitro aromatic compounds using [Rh]/DHTANa as catalyst in an aqueous bi-phase system". . p. 52 - 55. Retrieved 2016.
• 3、 Nishimura,Taguchi. "-". . p. 1625. Retrieved 1962.
• 4、 Brown et al.. "". . p. 2114. Retrieved 1972.
• 5、 Tomkins, Patrick,Gebauer-Henke, Ewa,Leitner, Walter,Müller, Thomas E.. "Concurrent Hydrogenation of Aromatic and Nitro Groups over Carbon-Supported Ruthenium Catalysts". . p. 203 - 209. Retrieved 2015.
• 6、 Cuypers, Thomas,Morias, Thomas,Windels, Simon,Marquez, Carlos,Van Goethem, Cédric,Vankelecom, Ivo,De Vos, Dirk E.. "Ni-Catalyzed reductive amination of phenols with ammonia or amines into cyclohexylamines". . p. 1884 - 1893. Retrieved 2020.
• 7、 Greenfield. "-". . p. 3082. Retrieved 1964.
• 8、 Moglie, Yanina,Alonso, Francisco,Vitale, Cristian,Yus, Miguel,Radivoy, Gabriel. "New active-iron based reducing system for carbonyl compounds and imines. Stereoselective reduction of cyclic ketones". . p. 2812 - 2819. Retrieved 2006.
• 9、 Bui-The-Khai,Concilio, Carlo,Porzi, Gianni. "Cyclization of α,ω Aliphatic Diamines and Conversion of Primary Amines to Symmetrical Tertiary Amines by a Homogeneous Ruthenium Catalyst". . p. 1759 - 1760. Retrieved 1981.
• 10、 Arcelli, Antonio,Khai, Bui-The,Porzi, Gianni. "SELECTIVE CONVERSION OF PRIMARY AMINES INRO N,N-DIMETHYLALKYL- OR N,N-DIALKYLMETHYL-AMINES WITH METHANOL AND RuCl2(Ph3P)3". . p. 93 - 96. Retrieved 1982.