Carbon Dioxide → Acetic acid, 2,2'-hydrazinylidenebis-

HRID 570116Notes

Reaction equation

HRID 570116 reaction equation
Cl[CH2:2][C:3]([OH:5])=[O:4].[C:6](=[O:9])([O-])[O-].[K+].[K+].[OH2:12].[NH2:13][NH2:14].[C:15](=O)=O>O>[N:13]([CH2:2][C:3]([OH:5])=[O:4])([CH2:15][C:6]([OH:9])=[O:12])[NH2:14]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 300Chloroacetic AcidHCID 11430Potassium Carbonate2×HCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 87983Acetic acid, 2,2'-hydrazinylidenebis-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Monochloroacetic acid (2 eq.) in water was neutralized with potassium carbonate (1 eq.) followed by the addition of hydrazine hydrate (1 eq.). Potassium carbonate (1 eq.) was added to the solution gradually, whereupon, with a steady evolution of CO2, the temperature rose to 70° C. The solution was then heated until the gas evolution stopped. At the end of the reaction, the 2,2′-(hydrazine-1,1-diyl)diacetic acid was precipitated by making the solution acidic with concentrated HCl. The product (mp 171° C.) was crystallized from water, and was confirmed by NMR spectroscopy and elemental analysis.

Workup

  1. customrose to 70° C
  2. temperatureThe solution was then heated until the gas evolution
  3. customAt the end of the reaction
  4. customthe 2,2′-(hydrazine-1,1-diyl)diacetic acid was precipitated
  5. customThe product (mp 171° C.) was crystallized from water

Sources & evidence

ORD record
ord-79a1adf6b66d43e1883b3118f90eaa55
Source dataset
uspto-grants-2015_05
Patent number
US09023837B2

Reaction notes

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