Amines, Fatty
Authors: Visek K. 
Published: August 2004

AbstractFatty amines are nitrogen derivatives of fatty acids, olefins, or alcohols prepared from natural sources, fats and oils, or petrochemical raw materials. Commercially available fatty amines consists of either a mixture of carbon chains or a specific chain length from C‐8–C‐22. The amines are classified as primary, secondary, or tertiary depending on the number of hydrogen atoms of an ammonia molecule replaced by fatty alkyl or methyl groups. Fatty amines are cationic surface‐active compounds which strongly adhere to surfaces by either physical or chemical bonding. Important commercial products are prepared using fatty amines as reactive intermediates. Commercially available fatty amines are most frequently prepared from naturally occurring materials by hydrogenation of a fatty nitrile intermediate. High purity fatty amines are also commercially available. These amines are prepared by distillation of either the precursor fatty acid or amine product mixture. Fatty alcohols react with ammonia or a primary or secondary amine in the presence of a catalyst to form amines. Data on physical properties of fatty amines have been well documented and summarized in many reference works on fatty acids and nitrogen derivatives. Fatty amines are insoluble in water, but soluble in organic solvents to varying degrees. Water, however, is soluble in the amines, and hydrates are formed. General amine chemistry is applicable to fatty amines. Many chemical reactions using fatty amines as reactive intermediates are run on an industrial scale to produce a wide range of important products. Important industrial reactions are salt formation, methylation of primary and secondary fatty amines, quaternization, ethoxylation and propoxylation, oxidation by hydrogen peroxide, and cyanoethylation. Fatty amine products are normally shipped in 55‐gal (208‐L), lined and unlined steel drums, or in tank cars or tank trucks for bulk shipments. High melting amines can be flaked and shipped in cardboard cartons or paper bags. Fatty alkylamines are generally considered to be irritating to both the skin and eyes. Depending on the chemical class, most fatty amines range from moderately toxic to practically nontoxic by acute oral ingestion. Fatty alkylamines are not considered especially toxic with regard to skin penetration and systemic absorption into the body. Long‐chain amines are not considered an inhalation hazard at ambient conditions because of their relatively low volatility. Fatty amines and chemical products derived from the amines are used in many industries. Uses for the nitrogen derivatives include fabric softeners, oil field chemicals, asphalt emulsifiers, petroleum additives, mining, and others. Amine salts are useful as flotation agents (collectors), corrosion inhibitors, and lubricants. The single largest market use for quaternary fatty amines is in fabric softeners. Another significant use for dialkyldimethyl quaternary ammonium salts and alkylbenzyldimethylammonium salts is in preparing organoclays for use as drilling muds, paint thickeners, and lubricants. Betaines, or specialty quaternaries, are used in the personal care industry in shampoos, conditioners, foaming, and wetting agents. A major use for ethoxylated and propoxylated amines is as an antistatic agent in the textile and plastics industry. Examples of uses for amine oxides include detergent and personal care areas as a foam booster and stabilizer or as a dispersant for glass fibers. Important uses for the diamines include: corrosion inhibitors, gasoline and fuel oil additives, flotation agents, pigment wetting agents, epoxy curing agents, herbicides, and asphalt emulsifiers. Fatty amines and derivatives are widely used in the oil field. In the mining industry, amines and diamines are used in the recovery and purification of minerals. A major use of fatty diamines is as asphalt emulsifiers. Diamines have also been used as epoxy curing agents, corrosion inhibitors, gasoline and fuel oil additives, and pigment wetting agents.