Alkanolamines from Olefin Oxides and Ammonia

Abstract

Ethylene oxide, propylene oxide, or butylene oxide react with ammonia to produce alkanolamines. Ethanolamines, NH 3- n (C 2 H 4 OH) n (C 2 H OH ) n ( n = 1,2,3, mono‐, di‐, and tri‐), are derived from the reaction of ammonia with ethylene oxide. Isopropanolamines, NH 3- n (CH 2 CHOHCH 3 ) n (mono‐, di‐, and tri‐), result from the reaction of ammonia with propylene oxide. Secondary butanolamines, NH 3- n (CH 2 CHOHCH 2 CH 3 ) n (mono‐, di‐, and tri‐), are the result of the reaction of ammonia with butylene oxide. Mixed alkanolamines can be produced from a mixture of oxides reacting with ammonia. Ethanolamines have been commercially available for over 50 years and isopropanolamines, for over 40 years. sec ‐Butanolamines have been prepared in research quantities, but are not available commercially. A variety of substituted alkanolamines are also available commercially, but have not reached the volume popularity of the ethanolamines and isopropanolamines. The freezing points of alkanolamines are moderately high. The ethanolamines are colorless liquids at or near room temperature. Alkanolamines are bifunctional molecules because of the alcohol and the amine functional groups in the same compound. This allows them to react in a wide variety of ways. Consumption of ethanolamines in the United States in chemical processing intermediates (captive use for ethyleneamine and surfactant applications) has increased significantly since the 1960s. Alkanolamines generally have low acute oral toxicity, but swallowing substantial quantities could have serious toxic effects. Exposure of the eye to undiluted alkanolamines can cause serious injury. Monoethanolamine and monoisopropanolamine are skin irritants, capable of producing serious injury in concentrations of 10% or higher. Alkanolamines and their derivatives are used in a wide variety of household and industrial applications. The amides are useful as foam stabilizers and aid cleaning in laundry detergents, dishwashing liquids, etc. Reaction of alkanolamines with a fatty acid at room temperature produces neutral alkanolamine soaps, found in cosmetics, polishes, household cleaners, and pharmaceuticals. Alkanolamine salts add to the surfactants line used in detergents, cosmetics, textiles, polishes, agricultural sprays, household cleaners, and metalworking compounds. Salts of alkanolamines and inorganic acids are useful chemical intermediates, and are used in corrosion inhibitors and antistatic agents, among other products.

Lysinol: a renewably resourced alternative to petrochemical polyamines and aminoalcohols

“…World production of these two classes of polyfunctional amines exceeds 1.5 × 10 9 kg per year (ethyleneamines: 3.9 × 10 8 kg per year in 2001; 14,15 ethanolamines: 1.1 × 10 9 kg per year in 1999 16,17 ). The processes used to manufacture these amines are shown in Scheme 2.…”