Chemical Properties
CLEAR LIQUID
Uses
Dimethylcyclohexylamine is used
in polyurethane plastics and textiles and as a chemical
intermediate.
Uses
N,
N-Dimethylcyclohexylamine has been used:
- as switchable hydrophilicity solvent (SHS) for the extraction of lipids from freeze-dried samples of Botryococcus braunii microalgae for biofuel production
- as catalyst in three-component organocatalyzed Strecker reaction on water
Definition
ChEBI: A tertiary amine consisting of cyclohexane having a dimethylamino substituent.
Application
The curing temperature of baking finishes comprising polyurethane-forming substances can be reduced by 50 – 80 ℃ by adding weakly acidic derivatives of N,N-Dimethylcyclohexylamine. Like pyridine, dimethylcyclohexylamine catalyzes certain reactions and is slightly more efficient than pyridine in the preparation of acid chlorides with thionyl chloride. It can be used as corrosion inhibitor and as an antioxidant in fuel oils.
Production Methods
N,N-Dimethylcyclohexylamine is manufactured either by the reaction of methyl
chloride or formaldehyde and hydrogen with cyclohexylamine (HSDB 1989).
Synthesis Reference(s)
Journal of the American Chemical Society, 93, p. 2897, 1971
DOI: 10.1021/ja00741a013Organic Syntheses, Coll. Vol. 6, p. 499, 1988
General Description
Colorless liquid with a musky ammonia odor. Less dense than water.
Air & Water Reactions
Highly flammable. Water soluble.
Reactivity Profile
N,N-Dimethylcyclohexylamine 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
Inhalation of high concentration of vapor will will produce irritation of the respiratory tract and lungs. Inhalation of large quantities of vapor may be fatal.
Health Hazard
Industrial hygiene studies in polyurethane manufacturing plants have identified
levels of 0.007-0.81 p.p.m. N-N-dimethylcyclohexylamine in air; however, these
levels were not regarded as hazardous (Reisdorf and Haggerty 1982). There are no
current exposure standards for N-N-dimethylcyclohexylamine and no documentation
of human toxicological effects.
Fire Hazard
Behavior in Fire: Dangerous when exposed to heat or flame. Can react vigorously with oxidizing materials.
Industrial uses
This amine is used as a catalyst in the production of polyurethane foams. It is also
used as an intermediate for rubber accelerators and dyes and in the treatment of
textiles.
Safety Profile
Poison by ingestion.
Moderately toxic by inhalation. Whenheated to decomposition it emits toxic
fumes of NOx
Metabolism
There is no record of any metabolic studies with MTV-dime thy ley clohexylamine.
However, one can predict that it would be oxidized to the N-oxide by either a
cytochrome P-450 system (Damani 1982) or the flavin-containing monooxygenase
(Ziegler 1988). Mixed function oxidase enzymes would be expected to produce
demethylation (Lindeke and Cho 1982). Many studies describe the metabolism of
the parent compound cyclohexylamine (Henderson 1990).
