Adipic Acid → Diethyl Adipate

HRID 2417762Notes

Reaction equation

HRID 2417762 reaction equation
[C:1]([OH:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[C:11](#N)[CH2:12]CCCC#N.[CH2:19](O)[CH3:20].C(C(CCC)C(OCC)=O)#N>>[C:1]([O:10][CH2:19][CH3:20])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:11][CH3:12])=[O:7]

Participants

5

Reactant 4

HCID 196Adipic AcidHCID 702EthanolHCID 8128AdiponitrileHCID 249721ethyl 2-cyanopentanoate

Product 1

HCID 8844Diethyl AdipateYield 3.1%

Conditions

Temperature
240 °C

Procedure

Then, 29.1 g (0.199 mole) of adipic acid and 21.0 g (0.194 mole) of adiponitrile were added to the liquid distillation residue, and the resulting mixture was introduced into a 1-liter, stainless autoclave. after purging with nitrogen, the content was stirred at 240° C. for 3 hours. After cooling the reaction mixture, 138.0 g (3.000 moles) of ethanol was added and the resulting mixture was stirred at 190° C. for 3 hours. As a result of analysis, it was confirmed that 60.3 g (0.389 mole) of ethyl cyanovalerate and 1.2 g (0.006 mole) of diethyl adipate were formed.

Workup

  1. additionthe resulting mixture was introduced into a 1-liter, stainless autoclave
  2. customafter purging with nitrogen
  3. additionwas added
  4. stirringthe resulting mixture was stirred at 190° C. for 3 hours
  5. customAs a result of analysis, it

Sources & evidence

ORD record
ord-75c27e17952c4e89a60d67204c911a09
Source dataset
uspto-grants-1984_09
Patent number
US04470928

Reaction notes

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