N-Bromosuccinimide by semi-batch bromination of succinimide in aqueous NaOH (500 t/a)

A batch plant: bromine (bromine-1) is dosed over 2 h into succinimide in cold caustic soda, the N-bromosuccinimide precipitates, is filtered, washed with ice water and vacuum-dried; half of the bromine leaves as NaBr in the mother liquor. Concept stage, assumed basis, 334 kg per batch every 5.3 h on a dedicated train, preliminary gate-to-gate LCI. The library's first batch entry.

Calculation maturity: not assessedDesign maturity: Concept (research)Not independently reviewedNitrogen organicsReport a problem with this process
Research outputNot engineering advice and not an approved design: do not use it for construction, operation or safety decisions. What this means

Overview

Succinimide and caustic soda (1.02 mol each per mol of bromine) are dissolved in water (30 mol per mol of bromine) and cooled to 278 K. Liquid bromine is dosed into the stirred charge over 2 h and reacts with the succinimide anion to N-bromosuccinimide and sodium bromide, the caustic route US 2 971 960 describes; the NBS precipitates from the cold liquor, which keeps 14.7 g per kg of water in solution. The slurry is filtered, the cake is reslurried with 1.5 kg of ice water per kg and filtered again, and dried at 333 K under vacuum in an agitated filter-dryer (two units, taking the batches in turn). The product is 99.0 wt% NBS with 0.75 wt% NaBr and 0.2 wt% water; the yield is 93.2 % on bromine. The mother liquor (15 wt% NaBr), the wash filtrate and the dryer condensate go to wastewater treatment: the bromide is not recovered.

The batch is modelled with cheme-as-code's semi-batch reactor (reactor: semibatch, core ADR 0050) and batch recipe (process/recipe.yaml, core ADR 0051): the dosing and post-reaction times come from the model, the brominator is the bottleneck (cycle 5.3 h, 1495 batches a year on a dedicated train), the recipe sizes the brominator (2 m3), and the flowsheet's flows are the recipe's year averages. The bromination's kinetics and heat of reaction are ASSUMED (no open data): a fast second-order reaction, so the bromine accumulates little (3.75 % at most, at the end of the dosing, as the imide's excess runs low) and the cooling-failure temperature stays within 1 K of the process temperature; this must be confirmed by reaction calorimetry. See DESIGN.md for every assumption.

Capacity
500 t/a dried NBS: 1495 batches/a of 334.41 kg in 7920 h on a dedicated train (63.13 kg/h year average), ASSUMED (DESIGN.md D-002, D-003, D-013)
Operation
7,920 h/a
Location
generic fine-chemicals site with a bromine supply (not chosen)
Engineering gates
Concept and feasibility (no results yet)
Maintainers
Artur Schweidtmann
Design basis and assumptions (7)
  • ASSUMED route: bromine into an alkaline succinimide solution at 278 K, NBS precipitating (D-001), the caustic route US 2 971 960 describes; half of the bromine leaves as NaBr.
  • ASSUMED succinimide and NaOH 1.02 per Br2, 30 kmol water per kmol Br2 in the charge (D-004).
  • ASSUMED fast effective rate law, first order in bromine and in the imide, and a heat of reaction of -80 kJ/mol overall (-30 in the dissolver, -50 in the brominator; D-005, D-009): no open kinetics or calorimetry; the low accumulation follows from them.
  • Solubility of NBS 14.7 g per kg water, the 25 C value (PubChem CID 67184, HSDB: 1.47 g/100 g water), taken at 278 K as well: the liquors leave saturated (D-005).
  • ASSUMED filters: 99.8 % solid recovery, 0.3 kg liquor per kg cake solid; reslurry wash with 1.5 kg ice water per kg solid (D-007).
  • ASSUMED vacuum drying at 333 K to 0.2 wt% moisture, 70 % thermal efficiency (D-008, D-009).
  • All flows are year averages of the recipe (D-003); duties and power concept estimates (scripts/balance.py, D-006, D-009); accuracy +/-30 % not demonstrated.

From process/design-basis.yaml.

Engineering model

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Drawing of the process (preview)Open the engineering model

The interactive model (drawings, streams, 3D) is made for larger screens.

Snapshot of c3ab348, cheme-as-code 1.6.0.

What goes in and out

In

  • SuccinimideFeedstockfeed:SUCC: technical succinimide (merchant), 0.603 kg/kg NBS
  • BromineFeedstockfeed:BR2: dry liquid bromine (bromine-1), 0.954 kg/kg NBS; half of it leaves as NaBr
  • Sodium hydroxideFeedstockfeed:NAOH: caustic soda 50 wt% (chlor-alkali-1), 0.487 kg/kg NBS, counted by mass of the solution
  • WaterFeedstockDissolution water, 2.98 kg/kg NBS
  • WaterFeedstockIce-cold wash water, 1.52 kg/kg NBS

Out

  • N-BromosuccinimideMain productDried NBS crystals, 99.0 wt% NBS, to packing
  • WastewaterWasteMother liquor, wash filtrate and dryer condensate, 5.54 kg/kg NBS: 10.9 wt% NaBr, 1.3 wt% dissolved NBS, succinimide and NaOH traces, to treatment

Utilities: Electricity (0.095 kWh/kg NBS: agitators of the dissolver, brominator and filter-dryers, vacuum pump (ASSUMED)), Steam (0.309 kWh (1.11 MJ)/kg NBS of LP steam to the filter-dryer's hot-water circuit), Chilled water (0.255 kWh/kg NBS removed by brine at 263 K: the caustic's dilution and the imide's deprotonation, cooling the charge, and the heat of bromination (the registry has chilled water, not brine: closest entry))

Show in the process graph

Reactions

IdAs writtenReactionOther processes
BROMC4H5NO2 + NaOH + Br2 → C4H4BrNO2 + NaBr + H2O · Bromination of succinimide in aqueous NaOHC4H5NO2+NaOH+Br2givesC4H4BrNO2+NaBr+H2O
DISSC4H4BrNO2(s) → C4H4BrNO2(aq) · Dissolution of NBS in the wash waterC4H4BrNO2givesC4H4BrNO2
PPTC4H4BrNO2(aq) → C4H4BrNO2(s) · Precipitation of NBS from the cold liquorC4H4BrNO2givesC4H4BrNO2

Each reaction's page has the conversion, heat of reaction, catalyst and sources this process states, next to those of other processes with the same reaction. All reactions

Life cycle assessment

–kg CO2-eqPreliminarypartial, 11 data gaps

Climate change per 1 kg N-Bromosuccinimide crystals, cradle-to-gate

No factors. No contribution is characterised, so no factor stands behind any number.

Main contributors
    Method and data
    Goal
    Preliminary gate-to-gate life cycle inventory of N-bromosuccinimide made by the semi-batch bromination of succinimide in aqueous sodium hydroxide at the concept stage: which raw materials, utilities and wastes the batch plant exchanges per kg of dried NBS, as the foreground for a later cradle-to-gate study. No impact results: most backgrounds are not mapped yet (D-012).
    Functional unit
    1 kg N-Bromosuccinimide crystals (1 kg N-Bromosuccinimide)
    Boundary
    cradle-to-gate
    Characterisation
    Factors kept with the process · GWP100
    Data quality
    No factors
    Result
    partial screening carbon footprint · 11 data gaps
    ScenarioClimate change (kg CO2-eq)
    baselineno total (data gaps)

    Inventory per 1 kg N-Bromosuccinimide crystals (12 flows)

    FlowPhaseDirectionQuantityUnitProvenance
    Process water (dissolution)operationinput2.983kgassumed
    Caustic soda 50 wt% (chlor-alkali-1)operationinput0.4871kgassumed
    Succinimide (merchant)operationinput0.6034kgassumed
    Liquid bromine (bromine-1)operationinput0.954kgassumed
    Ice-cold process water (cake wash)operationinput1.516kgassumed
    Electric poweroperationinput0.09504kWhassumed
    LP steam 350 kPa(a) (to the dryer's hot-water circuit)operationinput0.3086kWhassumed
    N-Bromosuccinimide crystals to packingoperationoutput1kgassumed
    Mother liquor, wash filtrate and dryer condensate to wastewater treatmentoperationoutput5.543kgcalculated
    Chilled brine return (263 K)operationoutput0.2553kWhassumed
    Rinse water of R-101 and F-101 between batchesoperationinput2.99kgassumed
    Disposal: Rinse water of R-101 and F-101 between batches (site wastewater treatment of the rinse water, with the saline bromide liquor (D-010))operationoutput2.99kgassumed

    Computed by ChemE-as-Code from lca/README.md, lca/dataset.yaml, lca/factors.yaml, lca/gaps.csv, lca/inventory.csv, lca/lca.yaml, lca/mappings.yaml, lca/results.csv, lca/results.md.

    In the open LCI database (cheme-as-code-atlas-preview-c3ab348) as N-Bromosuccinimide crystals to packing Preliminary.

    Download it for Brightway, openLCA and other tools.

    In the LCI database: system model, datasets and KPIs against the benchmarks

    In the LCI database

    Status
    Preliminary 4 unmapped exchanges. Some exchanges have no background mapping yet: they are exported unlinked and count no burden, so the inventory is incomplete.
    System model
    attributional, cut-off (methodology 1.1.0)
    Allocation
    mass (single-output, from default) · product:NBS 100 %
    Allocation findings
    none
    Change report
    Not available: this build has no change report against an earlier release.
    Dataset pages
    N-Bromosuccinimide crystals to packing Preliminary

    KPI benchmark positions

    KPIValueReference rangePosition
    Bromine consumption per kg of N-bromosuccinimide
    No open source with a plant's or a pilot's bromine use per kg NBS found (searched 2026-11-05: Google Patents for the preparation of N-bromosuccinimide from succinimide, bromine and NaOH, US 2 971 960 read; PubChem CID 67184; web search for NBS production yields). Only the stoichiometric floor, 0.898 kg/kg, is known.
    – kg/kgnot availablenot evaluated
    Wastewater (mother liquor, wash and condensate) per kg of N-bromosuccinimide
    No open source with the liquor volume of NBS manufacture found (searched 2026-11-05 as for nbs-specific-bromine); US 2 971 960 says only that the caustic route needs much water to wash the bromide out of the product, no amount.
    – kg/kgnot availablenot evaluated

    Maturity and review

    Design maturity Concept (claimed): An idea or first flowsheet; numbers are rough. Concept batch PFD with closed mass, component and element balances (cheme validate, cheme process streams: 3 blocks and 8 steps within tolerance). Every stream up to the dryer is calculated by cheme process propagate: the semi-batch R101 from its ASSUMED rate law, the precipitation and wash dissolution as conversion steps from the solubility of NBS, the filters as specified splits; scripts/balance.py repeats them and gives the dryer's outlets and the duties (no property package of core covers the alkaline bromide liquor, and core has no dryer). The recipe's year-average rate of the product agrees with the flowsheet (cheme process recipe, no cheme.recipe-basis finding). Thermal screening (cheme process reactor-hazards): dT_ad 19.7 K, accumulation 3.75 %, MTSR 278.9 K against an MTT of 331.9 K (the bromine's boiling point); no criticality class without a TD24 from calorimetry. The kinetics are assumed: the low accumulation rests on that assumption. Preliminary gate-to-gate LCI, the rinses between batches included (per-batch consumable); bromine and caustic soda linked to bromine-1 and chlor-alkali-1, the other backgrounds gaps. cheme maturity reaches no level (assumed feeds, kinetics and separations); the claim `maturity: concept` is the lowest value of the schema, not an evidenced level. Not reviewed. Needs cheme-as-code 1.7.0 (reactor: semibatch, process/recipe.yaml; core#158).

    Calculation maturity, from the checked evidenceNot assessed

    The process has no maturity report (cheme maturity, checks/maturity.json), so no calculation maturity is established.

    No level shownThe design maturity (Concept) is the manifest's claim, not evidence. A level appears here once the process's repository holds a current report from cheme maturity --write.

    Artifact completeness

    Which deliverables exist. They never raise a calculation maturity level: a drawing from unchecked numbers is still unchecked.

    Not reported without a maturity report.

    Independent review

    Not independently reviewed

    No independent engineering review yet. Automated checks passing is not a review.

    Set by people only. Reaching a calculation maturity level or passing automated checks is not an independent review or an approval.

    Where the evidence comes from
    Report
    processes/n-bromosuccinimide-1/checks/maturity.json (not in the library)
    Design basis
    process/design-basis.yaml
    Method
    How ChemE-as-Code checks the levels (requirement by requirement)

    Open items

    Sources

    Engineering project
    N-Bromosuccinimide · cheme-as-code>=1.7
    Library version
    c3ab348 (process last changed in c3ab348)
    Drawings rendered by
    cheme 1.6.0 (pyDEXPI 2.1.0)
    Data
    Catalog record (JSON) · CC-BY-4.0
    Files
    View the files on GitHub · change history and authors

    References

    How to cite

    For the data, cite the Process Atlas paper; for the platform that builds and checks it, the ChemE-as-Code paper.

    Schweidtmann, A. M. & Weber, J. M. (2026, in preparation). Process Atlas: an open, git-native, reproducible library and life cycle inventory of chemical processes (working title).

    For this process: "N-Bromosuccinimide by semi-batch bromination of succinimide in aqueous NaOH (500 t/a)", ChemE-as-Code process library, version c3ab348.

    BibTeX
    @unpublished{schweidtmann_process_atlas,
      author = {Schweidtmann, Artur M. and Weber, Jana M.},
      title = {{Process Atlas: an open, git-native, reproducible library and life cycle inventory of chemical processes (working title)}},
      year = {2026},
      url = {https://atlas.cheme-as-code.org},
      note = {in preparation}
    }

    Schweidtmann, A. M. (2026, in preparation). ChemE-as-Code: An Open-Source Platform for AI-Accelerated Chemical Process Engineering (working title).

    BibTeX
    @unpublished{schweidtmann_cheme_as_code,
      author = {Schweidtmann, Artur M.},
      title = {{ChemE-as-Code: An Open-Source Platform for AI-Accelerated Chemical Process Engineering (working title)}},
      year = {2026},
      url = {https://cheme-as-code.org},
      note = {in preparation}
    }