Ethyl cyanohydroxyiminoacetate Ethyl cyanohydroxyiminoacetate Ethyl cyanohydroxyiminoacetate (oxyma) is the oxime of ethyl cyanoacetate and finds use as an additive for carbodiimides, such as dicyclohexylcarbodiimide (DCC) in peptide synthesis. It acts as a neutralizing reagent for the basicity or nucleophilicity of the DCC due to its pronounced acidity (pKa 4.60) and suppresses base catalyzed side reactions, in particular racemization. Ethyl cyanohydroxyiminoacetate is obtained in the reaction of ethyl cyanoacetate and nitrous acid (from sodium nitrite and acetic acid) in 87% yield. Because of the rapid hydrolysis of the ester, the reaction should be carried out at pH 4.5, in buffered phosphoric acid the
Ethyl Gasoline Corp. v. United States laws, and accordingly was illegal when its effect was to "regiment" an entire industry. Ethyl owned several patents on tetra-ethyl lead, an anti-knock fuel additive, and on its utilization: two patents on the chemical itself, a patent on a motor fuel—gasoline containing tetra-ethyl lead, and a patent on a method of using the fuel in an automobile engine. Ethyl established an elaborate licensing program under its several patents: Ethyl sold the fuel additive, and licensed purchasers to use it to practice the other patents. The licensing program fixed prices for the motor fuel and strictly limited the types of customer