Ammonia → Iminodisuccinic acid

HRID 1532919Notes

Reaction equation

HRID 1532919 reaction equation
[OH-:1].[Na+].[C:3]([OH:10])(=[O:9])/[CH:4]=[CH:5]\[C:6]([OH:8])=[O:7].[NH3:11]>O>[NH:11]([CH:4]([CH2:5][C:6]([OH:8])=[O:7])[C:3]([OH:9])=[O:1])[CH:5]([CH2:4][C:3]([OH:10])=[O:9])[C:6]([OH:8])=[O:7].[C:3]([OH:10])(=[O:9])/[CH:4]=[CH:5]\[C:6]([OH:8])=[O:7].[C:3]([OH:10])(=[O:9])/[CH:4]=[CH:5]/[C:6]([OH:8])=[O:7].[C:3]([OH:10])(=[O:9])[CH:4]([CH2:5][C:6]([OH:8])=[O:7])[OH:1]

Participants

8

Reactant 3

HCID 222Ammonia4×HCID 14798Sodium Hydroxide4×HCID 444266Maleic Acid

Product 4

HCID 525Malic AcidYield 5%HCID 131409Iminodisuccinic acidYield 73%HCID 444266Maleic AcidYield 3%HCID 444972Fumaric AcidYield 10%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent4×

Procedure

In another particular embodiment, an Ma melt and aqueous sodium hydroxide solution are metered simultaneously and continuously in a molar ratio of MA:NaOH:H2O=2:1.5-3.5:6-20 into a maleic acid salt solution or pumpable suspension, which has been initially introduced and is of like composition, at temperatures of 75-125° C. This solution or suspension is pumped, with residence times of 0.1-5 h, into a second mixer, into which liquid ammonia or a concentrated aqueous ammonia solution is added continuously. the molar ratio of MA:ammonia here is 2:1.5-3.5. This solution is reacted at temperatures of 90-145° C. and residence times of 0.3-25 h in a continuous reactor. Ammonia and water are distilled off from the reaction mixture in a continuous distillation column at temperatures of 70-140° C. and residence times of 0.1-25 h, with continuous addition of water and aqueous sodium hydroxide solution corresponding to 0.5-2.5 mol of NaOH per 2 mol of MA originally employed. After the addition of water, solutions with solids contents of 5-60% by weight are obtained, and are subjected to a clarifying filtration, if appropriate. The product solutions have yields of >73% of iminodisuccinic acid, <3% of maleic acid, <10% of fumaric acid, <5% of malic acid and <15% of the particular theoretical yields of aspartic acid.

Workup

  1. customis of like composition, at temperatures of 75-125° C
  2. customThis solution is reacted at temperatures of 90-145° C. and residence times of 0.3-25 h in a continuous reactor
  3. customare obtained
  4. filtrationare subjected to a clarifying filtration

Sources & evidence

ORD record
ord-847b94418098442c9172c95137057bda
Source dataset
uspto-grants-2001_03
Patent number
US06207010B1

Reaction notes

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