Benzene → Benzenesulfonic Acid

HRID 2059009Notes

Reaction equation

HRID 2059009 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C1C=CC=CC=1.[S:13](=[O:16])(=[O:15])=[O:14]>S(=O)(=O)(O)O>[C:3]1([S:13]([OH:16])(=[O:15])=[O:14])[CH:2]=[CH:1][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 8058HexaneHCID 24682Sulfur trioxide

Product 1

HCID 7371Benzenesulfonic Acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A fifty-fifty (50/50) hexane mixture by volume of polypropyl benzene alkylates was charged to a continuous sulfonation unit. 20% sulfur trioxide (SO3) by weight in sulfuric acid (H2SO4) was charged to the unit. Spent sulfuric acid (H2SO4) was continuously removed in a two phase non-aqueous system leaving a polypropenyl benzene sulfonic acid product containing 7.4% by weight residual sulfuric acid (H2SO4). At this stage, water was added to dilute the residual sulfuric acid (H2SO4) to 85% by weight, including the sulfuric acid (H2SO4) generated from unused sulfur trioxide (SO3). The aqueous phase was separated from the resultant two phase aqueous-organic system, leaving the organic phase containing 0.98% by weight sulfuric acid (H2SO4). Hexane was added to the organic phase followed by addition of Calcium Carbonate (CaCO3). The resulting mixture was treated with SX-5W oil to reduce the viscosity of the sulfonic acid and also make a 30% by weight active product sulfonate. The product mixture was heated at 215° F. to strip the hexane. The hexane-stripped product was filtered to yield a sulfonic acid and oil product mixture containing less than 0.4%* by weight sulfuric acid.

Workup

  1. customSpent sulfuric acid (H2SO4) was continuously removed in a two phase non-aqueous system

Sources & evidence

ORD record
ord-0317588913f247cea9f9377a803c17d1
Source dataset
uspto-grants-1982_03
Patent number
US04321214

Reaction notes

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