Dicyclohexylamine

Structural formula
General
Surname	Dicyclohexylamine
other names	Aminodicyclohexane N , N -dicyclohexylamine ( IUPAC ) DCHA
Molecular formula	C 12 H 23 N
Brief description	colorless liquid with an amine-like odor
External identifiers / databases
CAS number 101-83-7 EC number 202-980-7 ECHA InfoCard 100.002.710 PubChem 7582 Wikidata Q425368
properties
Molar mass	181.32 g mol −1
Physical state	liquid
density	0.91 g cm −3
Melting point	0 ° C
boiling point	256 ° C (decomposition)
Vapor pressure	0.04 hPa (25 ° C)
solubility	heavy in water (1 g l −1 at 20 ° C) miscible with almost all common solvents soluble in ethanol , diethyl ether and acetone
Refractive index	1.484 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 301 + 311-314-410 P: 273-280-301 + 310 + 330-303 + 361 + 353-304 + 340 + 310-305 + 351 + 338
Toxicological data	373 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Dicyclohexylamine is a chemical compound from the group of aliphatic amines .

Extraction and presentation

Dicyclohexylamine can be prepared from cyclohexanone by hydrogenating amination or, in higher yields, from cyclohexanone and cyclohexylamine using palladium-carbon catalysts at a hydrogen pressure of 0.4 MPa. It can also be produced from phenol by means of hydrogenating amination or from phenol and aniline under appropriate conditions and with the use of catalysts. Dicyclohexylamine is also formed as a by-product in the production of cyclohexylamine from aniline and cyclohexanol or cyclohexanone.

properties

Dicyclohexylamine is a colorless liquid with an amine-like odor, which is miscible with almost all common solvents. Its aqueous solution has an alkaline reaction. From a temperature of 256 ° C the compound decomposes, producing carbon monoxide, carbon dioxide and nitrogen oxides.

use

Dicyclohexylamine is used as an intermediate in the manufacture of oil additives , insecticides , emulsifiers , anti-corrosion agents , plasticizers , vulcanization accelerators and dyes .
The carbonate and nitrite are used as volatile corrosion inhibitors .

safety instructions

The vapors of dicyclohexylamine can form an explosive mixture with air ( flash point 99 ° C). Contact with nitrosating agents (e.g. nitrites, nitrous acid , nitrous gases) can lead to the formation of carcinogenic nitrosamines , although dicyclohexylnitrosamine has no carcinogenic effect.

Individual evidence

1. ↑ ^{a b c d e f g h i j k} Entry on dicyclohexylamine in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
2. ↑ ^{a b c d} Toxicological assessment of dicyclohexylamine (PDF) at the professional association for raw materials and chemical industry (BG RCI), accessed on August 22, 2012.
3. ↑ Dicyclohexylamine data sheet from Sigma-Aldrich , accessed on March 24, 2011 ( PDF ).
4. ↑ Entry on dicyclohexylamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
5. ↑ Entry on VPI. In: Römpp Online . Georg Thieme Verlag, accessed on April 6, 2016.
6. ↑ BAUA: Dicyclohexylnitrosamine (PDF; 13 kB)