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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.
Cyanohydrin reaction of acetone with potassium cyanide Organic Syntheses Coll. Vol. 2, p. 7; Vol. 15, p. 1 Article; Cyanohydrin reaction of benzoquinone with ...
Thus, acetone cyanohydrin can be used for the preparation of other cyanohydrins, for the transformation of HCN to Michael acceptors, and for the formylation of arenes. Treatment of this cyanohydrin with lithium hydride affords anhydrous lithium cyanide:
In the most common route, methacrylic acid is prepared from acetone cyanohydrin, which is converted to methacrylamide sulfate using sulfuric acid.This derivative in turn is hydrolyzed to methacrylic acid, or esterified to methyl methacrylate in one step.
The principal route begins with the condensation of acetone and hydrogen cyanide: [4] (CH 3) 2 CO + HCN → (CH 3) 2 C(OH)CN. Sulfuric acid then hydrolyzes acetone cyanohydrin (ACH) to a sulfate ester-adduct, which is cracked to the ester: (CH 3) 2 C(OH)CN + 2H 2 SO 4 → ((CH 3) 2 C(OSO 3 H)C(O)NH 2 ·H 2 SO 4 → (CH 3) 2 C(OSO 3 H)C(O)NH 2 ...
In transhydrocyanation, an equivalent of HCN is transferred from a cyanohydrin, e.g. acetone cyanohydrin, to another HCN acceptor. 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. [6]
A key discovery in the preparation of these compounds was the finding by Jim Heather in the WRC Process Development group that acetone cyanohydrin was a good catalyst for the preparation of the o-chloro analogs. [28] Use of this catalyst allowed for the first time production of the o-nitro triketones.
Acetone cyanohydrin has been determined to be the natural substrate of HbHNL, though HbHNL also shows activity with mandelonitrile, the natural substrate of PaHNL.The cleavage of mandelonitrile into benzaldehyde and cyanide is what produces the characteristic amaretto smell of almonds. [18]