N,N-Dimethylcyclohexylamine

Chemical properties

CLEAR LIQUID

The Uses of N,N-Dimethylcyclohexylamine

Dimethylcyclohexylamine is used in polyurethane plastics and textiles and as a chemical intermediate.

The Uses of N,N-Dimethylcyclohexylamine

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.

Production Methods

N,N-Dimethylcyclohexylamine is manufactured either by the reaction of methyl chloride or formaldehyde and hydrogen with cyclohexylamine (HSDB 1989).

What are the applications of 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.

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 2897, 1971 DOI: 10.1021/ja00741a013
Organic 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).