Hydrogen Cyanide → Isophorone

HRID 440133Notes

Reaction equation

HRID 440133 reaction equation
[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([CH3:10])=[CH:3]1.COC(=O)[O-].C([N+](CC)(CC)C)C.[CH:24]#[N:25].OP(O)(O)=O>>[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([CH3:10])=[CH:3]1.[C:24]([C:4]1([CH3:10])[CH2:5][C:6]([CH3:8])([CH3:7])[CH2:9][C:2](=[O:1])[CH2:3]1)#[N:25]

Participants

6

Reactant 4

HCID 768Hydrogen Cyanide2×HCID 1004Phosphoric AcidHCID 6544Isophorone2×HCID 11019667Triethylmethylammonium methyl carbonate

Product 2

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

Procedure

To 622 g (4.5 mol) of isophorone in the presence of 4 g (0.021 mol) of triethylmethylammonium methylcarbonate there are added 288.3 g of a mixture of 3 mol of HCN and 1.5 mol of isophorone, over a period of 120 min and at a reaction temperature of 120° C. The HCN conversion at the end of the reaction is 99.9%. Following neutralization with 2.4g of H3PO4 the mixture is distilled. There are obtained 424.1 g of isophorone and 479.2 g of 3-cyano-3,5,5-trimethylcyclohexanone: the distillation residues weigh 12.8 g, this is equivalent to 1.4% based on the crude product used. The 3-cyano-3,5,5-trimethylcyclohexanone yield is thus 96.7% and the isophorone selectivity 99%.

Workup

  1. customat a reaction temperature of 120° C
  2. distillationis distilled

Sources & evidence

ORD record
ord-cc51bc8e6a6048aba97ac7bd7aacc511
Source dataset
uspto-grants-1996_05
Patent number
US05516928

Reaction notes

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