Hydrogen Cyanide → Isophorone

HRID 440134Notes

Reaction equation

HRID 440134 reaction equation
[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([CH3:10])=[CH:3]1.[CH:11]#[N:12].OP(O)(O)=O>[C-]#N.C([N+](CC)(CC)CC)C>[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([CH3:10])=[CH:3]1.[C:11]([C:4]1([CH3:10])[CH2:5][C:6]([CH3:8])([CH3:7])[CH2:9][C:2](=[O:1])[CH2:3]1)#[N:12]

Participants

6

Reactant 3

HCID 768Hydrogen Cyanide2×HCID 1004Phosphoric AcidHCID 6544Isophorone

Product 2

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

Reagents, catalysts & solvents 1

HCID 3014735Tetraethylammonium cyanideCatalyst

Procedure

To 415 g (3 mol) of isophorone containing 12 g (0.077 mol) of tetraethylammonium cyanide there are added dropwise, over a period of 1 hour, 81 g (3 mol) of hydrogen cyanide at a reaction temperature of 108° C. Following a post-reacting period of 3 min the HCN concentration is 0.16%. The effluent is neutralized with 9 g of H3PO4 and distilled. There are obtained 15 g of isophorone and 443.6 g of 3-cyano-3,5,5-trimethylcyclohexanone. This is equivalent to a yield of 89.6% based on HCN used and 93% based on converted isophorone. The distillation residues weigh 28.2 g, which is equivalent to 5.5% based on crude product used.

Workup

  1. customat a reaction temperature of 108° C
  2. customa post-reacting period of 3 min
  3. distillationdistilled

Sources & evidence

ORD record
ord-9996fdca10a940d5821a5ccacf1d4d91
Source dataset
uspto-grants-1996_05
Patent number
US05516928

Reaction notes

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