Acetone cyanohydrin

α-HydroxyisobutyronitrileAcetone cyanohydrin (ACH) is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate (PMMA), also known as acrylic. It liberates hydrogen cyanide easily, so it is used as a source of such. For this reason, this cyanohydrin is also highly toxic. Acetone cyanohydrin (ACH) is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate (PMMA), also known as acrylic. It liberates hydrogen cyanide easily, so it is used as a source of such. For this reason, this cyanohydrin is also highly toxic. In the laboratory, this compound may be prepared by treating sodium cyanide with acetone, followed by acidification: Considering the high toxicity of acetone cyanohydrin, a lab scale production has been developed using microreactor technology. to avoid needing to manufacture and store large quantities of the reagent. Alternatively, a simplified procedure involves the action of sodium or potassium cyanide on the sodium bisulfite adduct of acetone prepared in situ. This gives a less pure product, one that is nonetheless suitable for most syntheses. It is used as a surrogate in place of HCN, as illustrated by this synthesis of lithium cyanide: In transhydrocyanation, an equivalent of HCN is transferred from acetone cyanohydrin to another acceptor, with acetone as byproduct. The transfer is an equilibrium process, initiated by base. The reaction can be driven by trapping reactions or by the use of a superior HCN acceptor, such as an aldehyde. In the hydrocyanation reaction of butadiene, the transfer is irreversible. Acetone cyanohydrin is an intermediate en route to methyl methacrylate. Treated with sulfuric acid give the sulfate ester of the methacrylamide, methanolysis of which gives ammonium bisulfate and methyl methacrylate. Cassava tubers contain linamarin, a glucoside of acetohydrin, and the enzyme linamarinase for hydrolysing the glucoside. Crushing the tubers releases these compounds and produces acetone cyanohydrin. Acetone cyanohydrin is classified as an extremely hazardous substance in the US Emergency Planning and Community Right-to-Know Act. The principal hazards of acetone cyanohydrin arise from its ready decomposition on contact with water, which releases highly toxic hydrogen cyanide.