Diethyl 2,4-dicyanopentanedioate → Ethyl cyanoacrylate

HRID 279788

Reaction equation

HRID 279788 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:15]#[N:16])[CH2:6]C(C#N)C(OCC)=O)[CH3:2]>[OH-].[Na+].O>[CH2:1]([O:3][C:4](=[O:17])[C:5]([C:15]#[N:16])=[CH2:6])[CH3:2]

Participants

5

Reactant 2

HCID 15932776Diethyl 2,4-dicyanopentanedioateHCID 178486302HCID 178486302, compound

Product 1

HCID 81530Ethyl cyanoacrylateYield 114.4%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 962WaterSolvent

Procedure

In a 400 liter capacity stirrer-equipped vessel, 130 kg of distillation residue from the production of 2-cyanoacrylate, containing 75.1% by weight of 2,4-dicyanoglutaric acid diethyl ester (410 moles), were mixed with 21.3 kg of water and the resulting mixture reacted with 8.83 kg of 92% polyoxymethylene (271 moles) in the presence of 804.6 g of 32% NaOH solution which was required to adjust the pH into the range of from 4 to 6. The reaction was carried out and the reaction product worked up in the same way as described in EXAMPLE 1. 58.7 kg of pure 2-cyanoacrylic acid ethyl ester were obtained, corresponding to a yield of 60.1% by weight, based on 100% 2,4-dicyanoglutarate.

Workup

  1. customIn a 400 liter capacity stirrer-equipped vessel
  2. distillation130 kg of distillation residue from the production of 2-cyanoacrylate

Sources & evidence

ORD record
ord-0bc98e3b1814473c863977d4dc49ff0a
Source dataset
uspto-grants-1986_05
Patent number
US04587059

Linked notes

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