Nitro alcohols are obtained from nitroparaffins by reaction with aldehydes in the presence of an alkaline catalyst. Only 2‐nitro‐1‐butanol, 2‐ethyl‐2‐nitro‐1,3‐propanediol, 2‐methyl‐2‐nitro‐1‐propanol, 2‐methyl‐2‐nitro‐1,3‐propanediol, and 2‐hydroxymethyl‐2‐nitro‐1,3‐propanediol, the five nitro alcohols produced with formaldehyde, are manufactured in commercial quantities. All these nitro alcohols except nitrobutanol are crystalline solids when pure, are highly soluble in water, and are only moderately toxic by ingestion. The principal use of the nitro alcohols is as intermediates for the synthesis of amino alcohols by hydrogenation. The nitro alcohols also are a convenient starting material for the synthesis of diamines by a two‐step process involving the formation of a nitro amine by reaction of the hydroxyl group with a primary amine followed by hydrogenation. 2‐Methyl‐2‐nitro‐1‐propanol finds commercial use to promote adhesion of rubber to tire cord in radial tires. It also can serve as a source of formaldehyde in polymer cross‐linking. 2‐Hydroxymethyl‐2‐nitro‐1,3‐propanediol is a registered biocide useful for control of bacteria in such end uses as metalworking fluids and cooling tower water. This compound also finds acceptance in chemical toilets as an odor control agent.

Four nitroparaffins are commercially available. These four, nitromethane, nitroethane, 1‐nitropropane, and 2‐nitropropane, are medium‐boiling liquids which are excellent solvents for a wide variety organic compounds and polymers. Some physical properties of these nitroparaffins and a few higher mononitroparaffins and polynitro compounds are presented. The nitroparaffins can undergo a number of reactions which give them utility for synthesis of other compounds of commercial importance. These reactions are discussed. Of particular importance is their ability to form nitronate salts with alkalis. This reaction is the first step for the halogenation reaction, eg, for the synthesis of the fumigant chloropicrin, or the condensation with carbonyl compounds for the synthesis of nitro alcohols. Production of the four commercial nitroparaffins is by vapor‐phase nitration of propane with nitric acid. Some 41,000 t of mixed nitroparaffins can be produced annually. All the nitroparaffins are flammable liquids. Their principal hazard is by inhalation. Special attention is required for handling nitromethane because it can be detonated under certain circumstances. The bulk of nitroparaffin production is used for synthesis of other chemical products. Nitromethane is useful as a fuel in drag racing and model airplanes, however, and nitroethane and 1‐nitropropane see use as solvent in coatings.

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.

No 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. The 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 DOT 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 other alkanolamines. Typically, they 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.