Irreversible reaction

Sulfonation of toluene by chlorosulfonic acid, para

C7H8+ClHO3SC7H8O3S+HCl

Direction
Irreversible
Processes
1
Stated as
Rate law
Heat of reaction
ΔH = -100,000 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
C7H8Toluene108-88-3reactant-1
ClHO3SChlorosulfonic acid7790-94-5reactant-1
C7H8O3Sp-Toluenesulfonic acid104-15-4product1
HClHydrogen chloride7647-01-0product1

In the processes

  • p-Toluenesulfonyl chloride by semi-batch chlorosulfonation of toluene with a drown-out quench (1000 t/a)Concept · not reviewed

    SULP · Sulfonation of toluene by chlorosulfonic acid, paraC7H8 + HSO3Cl → p-CH3C6H4SO3H + HCl

    Stated as
    Rate law
    Phase
    liquid
    Element balance
    Balances in every element
    Heat of reaction
    ΔH = -100,000 kJ/kmol at 298.15 K, as written (assumed: ASSUMED (D-005): no open calorimetric value; an order of magnitude, HCl formed as a gas: an aromatic sulfonation by SO3 is commonly put at about -170 kJ/mol, and chlorosulfonic acid, the adduct of SO3 and HCl, brings less (D-005))
    Rate law
    basis: volume; driving: concentration; form: power_law; k: {"A":"2.858e5","Ea":50000}; orders: {"CSA":1,"TOL":1}; temperature range: 323.15 – 353.15 (assumed: ASSUMED fast effective rate (D-005): no open kinetics found (2026-11-05); the para share 90 % of the total rate after DE 1 912 956 A1, Example 1 (p-content of the crude 90 %); 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. DE 1 912 956 A1, Example 1: toluene dosed into chlorosulfonic acid with ammonium chloride at about 60-70 C over 2-3 h; crude with 90 % of the para isomer

    For the reaction · cited by p-Toluenesulfonyl chloride by semi-batch chlorosulfonation of toluene with a drown-out quench (1000 t/a)

  2. ASSUMED (D-005): no open calorimetric value; an order of magnitude, HCl formed as a gas: an aromatic sulfonation by SO3 is commonly put at about -170 kJ/mol, and chlorosulfonic acid, the adduct of SO3 and HCl, brings less (D-005)

    For the heat of reaction · cited by p-Toluenesulfonyl chloride by semi-batch chlorosulfonation of toluene with a drown-out quench (1000 t/a)