Ammonia → Iminodisuccinic acid

HRID 2379379Notes

Reaction equation

HRID 2379379 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].N.[NH2:10][C@H:11]([C:16]([OH:18])=[O:17])[CH2:12][C:13]([OH:15])=[O:14].[OH-].[Na+].Cl>O>[NH:10]([CH:11]([CH2:12][C:13]([OH:15])=[O:14])[C:16]([OH:18])=[O:17])[CH:3]([CH2:2][C:1]([OH:8])=[O:7])[C:4]([OH:6])=[O:5]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 5960L-Aspartic AcidHCID 14798Sodium HydroxideHCID 444266Maleic Acid

Product 1

HCID 131409Iminodisuccinic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 12.77 g (110 mmol) maleic acid, 19.2 g (300 mmol) of 28% aqueous ammonia, and 13.3 g (100 mmol) aspartic acid in 75 ml water was heated to 95° C. with stirring. The solution was adjusted to a pH of 9 with 10% aqueous sodium hydroxide, then stored at 95° C. for 20 hours. The resulting clear solution was cooled to room temperature and 11.95 g (300 mmol) concentrated hydrochloric acid was added. The resulting precipitate of maleic and fumeric acid was removed by filtration, and the supernatant was concentrated under pressure to yield the product as a white solid.

Workup

  1. temperatureThe resulting clear solution was cooled to room temperature
  2. customThe resulting precipitate of maleic and fumeric acid was removed by filtration
  3. concentrationthe supernatant was concentrated under pressure

Sources & evidence

ORD record
ord-136dc36eb9cc4b9492f83f8bbe6beacd
Source dataset
uspto-grants-1994_11
Patent number
US05362412

Reaction notes

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