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It is used as a surrogate in place of HCN, as illustrated by its use as a precursor to lithium cyanide: [8] (CH 3) 2 C(OH)CN + LiH → (CH 3) 2 CO + LiCN + H 2. 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 ...
Acetone cyanohydrin, (CH 3) 2 C(OH)CN is the cyanohydrin of acetone.It is generated as an intermediate in the industrial production of methyl methacrylate. [3] In the laboratory, this liquid serves as a source of HCN, which is inconveniently volatile. [4]
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]
Cyanohydrin reaction of acetone with potassium cyanide Organic Syntheses Coll. Vol. 2, p. 7; Vol. 15, p. 1 Article; Cyanohydrin reaction of benzoquinone with ...
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:
To replace the use of toxic hydrocyanide (HCN) gas or surrogates such as acetone cyanohydrin, Bill Morandi and co-workers developed a hydrocyanation strategy using shuttle catalysis. [10] In this example, they use isovaleronitrile as a HCN surrogate under nickel/aluminum co-catalyzed conditions to afford hydrocyanation reactions of various alkenes.
Hydrogen cyanide (formerly known as prussic acid) is a chemical compound with the formula HCN and structural formula H−C≡N.It is a highly toxic and flammable liquid that boils slightly above room temperature, at 25.6 °C (78.1 °F).
Acetone (2-propanone or dimethyl ketone) is an organic compound with the formula (CH 3) 2 CO. [22] It is the simplest and smallest ketone (>C=O).It is a colorless, highly volatile, and flammable liquid with a characteristic pungent odour, very reminiscent of the smell of pear drops.