Hydrogen Cyanide → 3-Cyano-3,5,5-trimethylcyclohexanone

HRID 377048

Reaction equation

HRID 377048 reaction equation
[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5]C(C)=[CH:3]1.C[N+:12]1[CH:16]=[C:15]([C:17]([O-])=O)N(C)C=1.C#N>>[CH3:5][C:6]1([CH3:8])[CH2:7][C:15]([C:16]#[N:12])([CH3:17])[CH2:3][C:2](=[O:1])[CH2:9]1

Participants

4

Reactant 3

HCID 768Hydrogen CyanideHCID 6544Isophorone2×HCID 4799511,3-Dimethylimidazolium-4-carboxylate

Product 1

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

Conditions

Temperature
120 °C

Procedure

622 g (4.5 mol) of isophorone and 3.61 g (25.8 mmol) of 1,3-dimethylimidazolium-4-carboxylate were placed in a reaction vessel and a mixture of 207.3 g (1.5 mol) of isophorone and 81.0 g (3 mol) of hydrogen cyanide was added at 120° C. over a period of about 120 minutes. The mixture was subsequently stirred further for about 120 minutes at 120° C. After cooling, the HCN concentration was determined by titration. Free hydrocyanic acid could no longer be detected (HCN conversion>99.9%). After addition of 2.0 g of 85% strength H3PO4, the reaction product was distilled at 0.1 hPa. This gave 473 g of 3-cyano-3,5,5-trimethylcyclohexanone (95.4% based on HCN used).

Workup

  1. additionwas added at 120° C. over a period of about 120 minutes
  2. temperatureAfter cooling
  3. concentrationthe HCN concentration
  4. additionAfter addition of 2.0 g of 85% strength H3PO4
  5. distillationthe reaction product was distilled at 0.1 hPa

Sources & evidence

ORD record
ord-32c9bf0864c444d58e30b255fb565f88
Source dataset
uspto-grants-2000_02
Patent number
US06022988

Linked notes

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