Hydrogen Cyanide → Isophorone

HRID 440132Notes

Reaction equation

HRID 440132 reaction equation
[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([CH3:10])=[CH:3]1.C#N.COC(=O)[O-].C[N+:19]([CH3:22])(C)C>>[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([CH3:10])=[CH:3]1.[C:22]([C:4]1([CH3:10])[CH2:5][C:6]([CH3:8])([CH3:7])[CH2:9][C:2](=[O:1])[CH2:3]1)#[N:19]

Participants

5

Reactant 3

HCID 768Hydrogen CyanideHCID 6544Isophorone2×HCID 11804927Tetramethylammonium Methyl Carbonate

Product 2

HCID 6544IsophoroneHCID 990683-Cyano-3,5,5-trimethylcyclohexanone

Procedure

To 622 g (4.5 mol) of isophorone there are added, at 120° C. over a period of 120min, a mixture of 207.3 g (1.5mol) of isophorone and 81 g (3.0 mol) of HCN in the presence of 5.2 g (0.02 mol) of a 50% strength aqueous tetramethylammonium methylcarbonate solution. 10 min after the end of the metering operation the HCN concentration is only 140 ppm. Following neutralization with 4 g of H3PO4 the mixture is distilled. Following a first runoff of 3 g, there are obtained 422.6 g of isophorone and 476.7 g of 3-cyano-3,5,5-trimethylcyclohexanone. This is equivalent to a yield of 96.2% based on HCN used and 98% based on isophorone converted.

Workup

  1. concentration10 min after the end of the metering operation the HCN concentration
  2. distillationis distilled

Sources & evidence

ORD record
ord-6858908435444d079b1d7c84a7fd4b77
Source dataset
uspto-grants-1996_05
Patent number
US05516928

Reaction notes

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