Adipic Acid → Dimethyladipate

HRID 2417764Notes

Reaction equation

HRID 2417764 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]>>[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

5

Reactant 3

HCID 196Adipic AcidHCID 8128AdiponitrileHCID 12329Dimethyladipate

Product 2

HCID 12329DimethyladipateHCID 12349930HCID 12349930, compound

Procedure

Then, 59.1 g (0.405 mole) of adipic acid, 43.7 g (0.405 mole) of adiponitrile and 26.8 g (0.154 mole) of dimethyl adipate were added to the liquid distillation residue and the resulting mixture was introduced into the autoclave mentioned above. Thereafter, reaction was carried out in the same manner as above. As a result of distillation, there were obtained 120.0 g (0.851 mole) of methyl cyanovalerate and 25.6 g (0.147 mole) of dimethyl adipate (Repeated Experiment 1). Subsequently, by the same procedure as above, the same amount of adipic acid as used in Repeated Experiment 1 and adiponitrile in an amount as shown in Table 3 were added to the liquid distillation residue obtained by distilling off methyl cyanovalerate and dimethyl adipate, and the reaction and distillation were repeated (Repeated Experiments 2-5). The results are shown in Table 3.

Workup

  1. additionthe resulting mixture was introduced into the autoclave
  2. customThereafter, reaction
  3. customAs a result of distillation

Sources & evidence

ORD record
ord-9e90b7be9b9f4a92a8e6ec08c8f89933
Source dataset
uspto-grants-1984_09
Patent number
US04470928

Reaction notes

Loading…