Sulfonation

Sulfonation introduces a sulfonic acid group (–SO₃H) into an organic molecule. It is used to alter acidity, water solubility, and chemical reactivity.

Electrophilic aromatic substitution: A reaction class in which an electrophile replaces hydrogen on an aromatic ring. Aromatic sulfonation proceeds by replacing a ring hydrogen with an electrophilic sulfur-containing group.
Alkylbenzene sulfonates: Anionic surfactants consisting of an alkylbenzene group attached to a sulfonate group. Industrial sulfonation converts alkylbenzenes into major detergent ingredients.
Sulfonic acid: An organic acid containing the functional group R–SO₃H. This is the functional group introduced by sulfonation.
Nitration: The introduction of a nitro group into an organic molecule, commonly by aromatic substitution. Like aromatic sulfonation, it substitutes an electrophile onto an aromatic ring, but installs –NO₂.
Water solubility: The extent to which a substance dissolves in water under specified conditions. Ionization of introduced sulfonic acid groups often greatly increases a compound’s aqueous solubility.
Sulfur trioxide: A reactive sulfur oxide used to introduce sulfonic acid groups into organic compounds. It is the principal electrophile in many aromatic sulfonation mixtures.
Linear alkylbenzene sulfonate: A widely used anionic surfactant made by sulfonating linear alkylbenzenes and neutralizing the product. Its production illustrates large-scale aromatic sulfonation for household and industrial cleaners.
Sulfonate: The conjugate base or anionic form of a sulfonic acid, with group R–SO₃⁻. In water, sulfonated products commonly exist as sulfonate ions rather than neutral acids.
Halogenation: The introduction of one or more halogen atoms into a chemical compound. Aromatic halogenation is another electrophilic ring substitution, but installs a halogen instead of –SO₃H.
Directing effect: The influence of an aromatic substituent on the position of a subsequent electrophilic substitution. A sulfonic acid group deactivates the ring and directs further substitution mainly to meta positions.

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