Irreversible reaction

p-Toluenesulfonic acid to p-toluenesulfonyl chloride by excess chlorosulfonic acid

C7H8O3S+ClHO3SC7H7ClO2S+H2SO4

Direction
Irreversible
Processes
1
Stated as
Fixed conversion
Heat of reaction
ΔH = -10,000 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
C7H8O3Sp-Toluenesulfonic acid104-15-4reactant-1
ClHO3SChlorosulfonic acid7790-94-5reactant-1
C7H7ClO2Sp-Toluenesulfonyl chloride98-59-9product1
H2SO4Sulfuric acid7664-93-9product1

In the processes

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

    CHLP · p-Toluenesulfonic acid to p-toluenesulfonyl chloride by excess chlorosulfonic acidp-CH3C6H4SO3H + HSO3Cl → p-CH3C6H4SO2Cl + H2SO4

    Stated as
    Fixed conversion
    Phase
    liquid
    Element balance
    Balances in every element
    Conversion
    90 % of PTSA (assumed: ASSUMED (D-005): 90 % of the sulfonic acid converted with the second 1.5 mol of acid in 1 h at 35 C; the patent's crude after its solvent work-up is 84-85 % of theory (DE 1 912 956 A1, Example 1))
    Heat of reaction
    ΔH = -10,000 kJ/kmol at 298.15 K, as written (assumed: ASSUMED small (D-005): the patent adds the second portion of acid in 5-10 min at 35 C, which a strongly exothermic step would not allow; no calorimetric value)

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: cooled to about 35 C, 1.5 mol chlorosulfonic acid added over 5-10 min, stirred about 1 h

    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): 90 % of the sulfonic acid converted with the second 1.5 mol of acid in 1 h at 35 C; the patent's crude after its solvent work-up is 84-85 % of theory (DE 1 912 956 A1, Example 1)

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

  3. ASSUMED small (D-005): the patent adds the second portion of acid in 5-10 min at 35 C, which a strongly exothermic step would not allow; no calorimetric value

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