Ethylene oxide ethanolamines from

Ethylene oxide [75-21-8] was first prepared in 1859 by Wurt2 from 2-chloroethanol (ethylene chlorohydrin) and aqueous potassium hydroxide (1). He later attempted to produce ethylene oxide by direct oxidation but did not succeed (2). Many other researchers were also unsuccesshil (3—6). In 1931, Lefort achieved direct oxidation of ethylene to ethylene oxide using a silver catalyst (7,8). Although early manufacture of ethylene oxide was accompHshed by the chlorohydrin process, the direct oxidation process has been used almost exclusively since 1940. Today about 9.6 x 10 t of ethylene oxide are produced each year worldwide. The primary use for ethylene oxide is in the manufacture of derivatives such as ethylene glycol, surfactants, and ethanolamines. 

Many accidents occur because process materials flow in the wrong direction. Eor example, ethylene oxide and ammonia were reacted to make ethanolamine. Some ammonia flowed from the reactor in the opposite direction, along the ethylene oxide transfer line into the ethylene oxide tank, past several non-return valves and a positive displacement pump. It got past the pump through the relief valve, which discharged into the pump suction line. The ammonia reacted with 30m of ethylene oxide in the tank, which ruptured violently. The released ethylene oxide vapor exploded causing damage and destruction over a wide area [5]. A hazard and operability study might have disclosed the fact that reverse flow could occur. 

Production of the ethanolamines mentioned above, from ethylene oxide and ammonia ... 

Pentryl (152) is obtained from the action of fuming nitric acid or mixed acid on Ai-(2,4-dinitrophenyl)ethanolamine, itself obtained from the reaction of 2,4-dinitrochlorobenzene with ethanolamine. Another route to pentryl (152) involves the nitration of A-phenylethanol-amine, which is obtained from the reaction of aniline with ethylene oxide. ... 

Pentryl has been prepared by two methods (a) from aniline and ethylene oxide (according to Herz [80]) and (b) from chlorodinitrobenzene and ethanolamine (according to Moran) with the subsequent nitration of N-hydroxyethylaniline or its dinitro derivative ... 

Ethylene oxide, propylene oxide, or butylene oxide react with ammonia to produce alkanolamines. The more popular ethanolamines [NH3 h(C2H4OH)h, where n = 1,2,3 monoethanolamine, diethanolamine, and triethanolamine], are derived from the reaction of ammonia with ethylene oxide. 

Vegetable oils and natural fats are traditional raw materials for the production of soaps and other surfactants. Coconut oil, palm and palm kernel oil, rape oil, cotton oil, tall oil, as well as the fats of animal origin (tallow oil, wool wax), present renewable raw sources. Linear paraffins and olefins (with terminal or internal double bond), higher synthetic alcohols, and benzene are fossil sources for surfactant production which are obtained from oil, natural gas and coal. Other auxiliary materials are required to construct amphiphilic surfactant structure, such as ethylene oxide, sulphur trioxide, phosphorous pentaoxide, chloroacetic acid, maleic anhydride, ethanolamine, and others. 

An investigation of the influence of metal phosphate catalysts on the products from the interaction of ethylene oxide and ammonia reveals a surprising range of products including pyridine, a- and y-picolines, acetic acid, ethanolamine, piperazine, aziridine, diethylamine, ethylenediamine, and dioxan. The synthesis and identification of the four possible geometric... 

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