Adipic Acid → Dimethyladipate

HRID 2417763Notes

Reaction equation

HRID 2417763 reaction equation
C(O)(=O)CCCCC(O)=O.C(#N)[CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[N:17].[C:19]([O:29][CH3:30])(=[O:28])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25].CO>>[C:16]([CH:15]([CH2:14][CH2:13][CH3:12])[C:24]([O:26][CH3:27])=[O:25])#[N:17].[C:24]([O:26][CH3:27])(=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][C:19]([O:29][CH3:30])=[O:28]

Participants

6

Reactant 4

HCID 196Adipic AcidHCID 887MethanolHCID 8128AdiponitrileHCID 12329Dimethyladipate

Product 2

HCID 12329DimethyladipateHCID 12349930HCID 12349930, compound

Conditions

Temperature
220 °C

Procedure

Into a 2-liter, stainless autoclave were introduced 73.0 g (0.500 mole) of adipic acid, 432.0 g (4.000 moles) of adiponitrile and 26.1 g (0.150 mole) of dimethyl adipate. After purging with nitrogen, the content was stirred at 220° C. for 5 hours. After cooling the reaction mixture 320.0 g (10.000 moles) of methanol was added and the resulting mixture was stirred at 220° C. for 1 hour. By distilling the reaction mixture, there were obtained 114.2 g (0.810 mole) of methyl cyanovalerate and 26.8 g (0.154 mole) of dimethyl adipate.

Workup

  1. customAfter purging with nitrogen
  2. additionwas added
  3. stirringthe resulting mixture was stirred at 220° C. for 1 hour
  4. distillationBy distilling the reaction mixture

Sources & evidence

ORD record
ord-fe7add62da244c228dbac3e968aa3d73
Source dataset
uspto-grants-1984_09
Patent number
US04470928

Reaction notes

Loading…