Alkanolamines from Nitro Alcohols

Abstract

The nitro alcohols obtained by the condensation of nitroparaffins with formaldehyde may be reduced to a unique series of alkanolamines (β‐amino alcohols). The five primary amino alcohols manufactured on a commercially significant scale are 2‐amino‐2‐methyl‐1‐propanol (AMP), 2‐amino‐2‐ethyl‐1,3‐propanediol (AEPD), 2‐amino‐2‐(hydroxymethyl)‐1,3‐propanediol (TRIS AMINO), 2‐amino‐2‐methyl‐1,3‐propanediol (AMPD), and 2‐amino‐1‐butanol (AB). 2‐dimethylamino‐2‐methyl‐1‐propanol (DMAMP) is the only N‐substituted derivative of these compounds available in commercial quantities. These six commercial alkanolamines are highly soluble in water. They are generally very soluble in alcohols, slightly soluble in aromatic hydrocarbons, and nearly insoluble in aliphatic hydrocarbons. According to current U.S. Department of Transportation regulations, AMP, AMP‐95, DMAMP, DMAMP‐80, AEPD, and AB are all classified as combustible liquids. The commercial alkanolamines exhibit the chemical reactivity of both amines and alcohols, as do other alkanolamines. Typically, they will attack copper, brass, and aluminum, but not steel or iron. Alkanolamines are useful as amination agents. The reduction of nitro alcohols to alkanolamines is accomplished by hydrogenation in the presence of Raney nickel catalyst. Alkanolamines are only slightly toxic by ingestion. Undiluted DMAMP, AMP‐95, and AB cause eye burns and permanent damage if not washed out immediately. The 40% aqueous solution of TRIS AMINO is nonirritating to the eyes and skin. Alkanolamines are used in emulsions, pigment dispersion, resin solubilizers, catalysts, applications in oil and gas production, and in biomedical and synthetic applications.