Aromatic sulfonation is an organic reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid functional group in an electrophilic aromatic substitution. Organic reactions are Chemical reactions involving Organic compounds The basic Organic chemistry reaction types are Addition reactions Elimination Sulfonic acid is an unstable Acid with the formula H-S(=O2-OH In Organic chemistry, functional groups are specific groups of Atoms within Molecules that are responsible for the characteristic Chemical reactions Electrophilic aromatic substitution or EAS is an Organic reaction in which an atom usually Hydrogen, appended to an aromatic system is replaced
Sulfur trioxide is the electrophile in this reaction generated from concentrated sulfuric acid (or fuming sulfuric acid) when heated. Sulfur trioxide (also spelled sulphur trioxide) is the chemical compound with the formula SO3 In Chemistry, an electrophile (literally electron-lover) is a Reagent attracted to Electrons that participates in a chemical reaction by accepting Sulfuric (or sulphuric acid, H 2 S[[oxygen O]]4 is a strong Mineral acid.
In contrast to aromatic nitration and other electrophilic aromatic substitutions this reaction is reversible. Nitration is a general Chemical process for the introduction of a nitro group into a Chemical compound. A reversible reaction is a Chemical reaction that results in an equilibrium mixture of Reactants and products. Sulfonation takes place in concentrated acidic conditions and desulfonation is the mode of action in a dilute hot aqueous acid.
It is very useful in protecting a piece of an aromatic compound because of this reversibility. See Aromatic Hydration.
Tyrer sulfonation process
In the Tyrer sulfonation process (1917) [1], at some time of technological importance, benzene vapor is led through a vessel containing 90% sulfuric acid the temperature of which is increased from 100 to 180°C. Water and benzene are continuously removed in a condenser and the benzene layer fed back to the vessel. In this way a 80% yield is obtained.
Application
Aromatic sulfonic acids are intermediates in the preparation of dyes and many pharmaceuticals. A dye can generally be described as a Colored substance that has an affinity to the substrate to which it is being applied Sulfonation of aniline produces p-aminobenzenesulfonic acid or sulfanilic acid which is a zwitterion with an unusual high melting point. Aniline, phenylamine or aminobenzene is an Organic compound with the formula C6H7N Sulfanilic acid ( 4-aminobenzene sulfonic acid) is a colourless crystalline solid produced from sulfonation of Aniline. A zwitterion (first part pronounced "tsvitter" from German " Zwitter " &mdash "hybrid" " Hermaphrodite " is a The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The amide of this compound and related compounds form a large group of sulfa drugs. There are several sulfonamide-based groups of drugs The original antibacterial sulfonamides (sometimes called simply sulfa drugs are synthetic antimicrobial agents that contain the sulfonamide
Sulfonation of polystyrene can be used to prepare sodium polystyrene sulfonate. Polystyrene ˌpɒliˈstaɪriːn ( IUPAC Polyphenylethene is an aromatic Polymer made from the aromatic Monomer Styrene Sodium polystyrene sulfonate (or polystyrene sulfonic acid) is a type of Polymer and Ionomer based on Polystyrene.