Irreversible reaction

Bromination of succinimide in aqueous NaOH

C4H5NO2+NaOH+Br2C4H4BrNO2+NaBr+H2O

Direction
Irreversible
Processes
1
Stated as
Rate law
Heat of reaction
ΔH = -50,000 kJ/kmol (one process)
Element balance
Checked: balances
As the processes state itStoichiometry, conversions, heats of reaction and catalyst windows are taken from each process's files with their provenance. The build checks only that each process's equation balances in every element, from the process's own component formulas; it does not check the numbers. A process's design maturity applies to them.

Species

SpeciesNameCASRoleCoefficient
C4H5NO2Succinimide123-56-8reactant-1
NaOHSodium hydroxide1310-73-2reactant-1
Br2Bromine7726-95-6reactant-1
C4H4BrNO2N-Bromosuccinimide128-08-5product1
NaBrSodium bromide7647-15-6product1
H2OWater7732-18-5product1

In the processes

  • N-Bromosuccinimide by semi-batch bromination of succinimide in aqueous NaOH (500 t/a)Concept · not reviewed

    BROM · Bromination of succinimide in aqueous NaOHC4H5NO2 + NaOH + Br2 → C4H4BrNO2 + NaBr + H2O

    Stated as
    Rate law
    Phase
    liquid
    Element balance
    Balances in every element
    Heat of reaction
    ΔH = -50,000 kJ/kmol at 298.15 K, as written (assumed: ASSUMED (D-005): -80 kJ/mol overall, less the imide's deprotonation by NaOH (-30 kJ/mol) released in M101; no open calorimetric value found)
    Rate law
    basis: volume; driving: concentration; form: power_law; k: {"A":"1.003e6","Ea":40000}; orders: {"BR2":1,"SUCC":1}; temperature range: 273.15 – 303.15 (assumed: ASSUMED fast effective rate (D-005): no open kinetics found (2026-11-05); to be replaced by reaction calorimetry)

Sources

What the processes cite for this reaction, each source once: for the reaction itself, its conversion, its heat of reaction or its catalyst. As the processes write them; DOIs, US patent numbers and web addresses are linked.

  1. US 2 971 960 (Waugh and Waugh, 1961), column 1: the caustic route and its NaBr by-product

    For the reaction · cited by N-Bromosuccinimide by semi-batch bromination of succinimide in aqueous NaOH (500 t/a)

  2. ASSUMED (D-005): -80 kJ/mol overall, less the imide's deprotonation by NaOH (-30 kJ/mol) released in M101; no open calorimetric value found

    For the heat of reaction · cited by N-Bromosuccinimide by semi-batch bromination of succinimide in aqueous NaOH (500 t/a)