Sulfonating agents

Unsaturated Hydrocarbons. The reaction of long-chain, ie, CC-olefins with strong sulfonating agents leads to surface-active... 

Chlorosulfuric acid is used as a sulfonating agent in the preparation of resin-based ion exchange (qv) materials. Sulfonation of glycol phthalate or... 

Oleum. Fuming sulfuric acid a soln of sulfur trioxide in sulfuric acid used as a sulfating and sulfonating agent. See under Acidity in Acids in Vol 1, A88-R to A90-R Acids Used in Manufacture and Analysis of Explosives in Vol 1, A93-L to A93-R and under Nitration in this Vol For analytical procedures, see under Glass Bulbs for Weighing Acids in Vol 6, G78-R to G79-R... 

Further auxiliary agents for the production of anionic surfactants are the sulfation and sulfonation agents oleum, chlorosulfonic acid, C1-S02-0H, air-S03 mixtures, air-S02 mixtures, sultones (especially 1,3-propanesultone (CH2—CH2—CH2—SO2), and isethionic acid (2-hydroxyethanesulfonic O-------------------1... 

The direct reaction of 1-alkenes with strong sulfonating agents leads to surface-active anionic mixtures containing both alkenesulfonates and hydroxyalkane sulfonates as major products, together with small amounts of disulfonate components, unreacted material, and miscellaneous minor products (alkanes, branched or internal alkenes, secondary alcohols, sulfonate esters, and sultones). Collectively this final process mixture is called a-olefinsulfonate (AOS). The relative proportions of these components are known to be an important determinant of the physical and chemical properties of the surfactant [2]. 

The nature of the sulfonating agent (S03, free or as its dioxane—or tributyl phosphate—adduct) as well as temperature variations were shown to result in significant changes in AOS composition. 

In the first step an S03 molecule is inserted into the ester binding and a mixed anhydride of the sulfuric acid (I) is formed. The anhydride is in a very fast equilibrium with its cyclic enol form (II), whose double bonding is attacked by a second molecule of sulfur trioxide in a fast electrophilic addition (III and IV). In the second slower step, the a-sulfonated anhydride is rearranged into the ester sulfonate and releases one molecule of S03, which in turn sulfonates a new molecule of the fatty acid ester. The real sulfonation agent of the acid ester is not the sulfur trioxide but the initially formed sulfonated anhydride. In their detailed analysis of the different steps and intermediates of the sulfonation reaction, Schmid et al. showed that the mechanism presented by Smith and Stirton [31] is the correct one. 

The mole ration sulfonating agent-organic feedstock Sulfonation temperature (mild temperatures are key)... 

There are four reasons why S03/air raised from sulfur is becoming the predominant sulfonation agent for the manufacture of high-quality anionic surfactants ... 

There are four main sulfonation reactor configurations applied worldwide to produce all kinds of top quality anionic surfactants from sulfur-based S03/air as the sulfonating agent. All these systems have proven and documented experience ... 

The well-known and continuously improved technology of S03/gas production starting from elementary sulfur is the source of the sulfonating agent of choice. In Figs. 6 and 7 simplified process scheme for air drying and S02/S03 production are illustrated. 

Sulfonating the asphalt with a liquid sulfonating agent, such as liquid sulfur trioxide... 

This is a batch-type process in which the rates of flow of the solvent, the asphaltic material, the sulfonating agent, and the neutralizing agent and the... 

Fluorosulfonic acid can be used in fluorination reactions, and it functions as a catalyst in reactions such as alkylation and polymerization. One of the most important uses of FS03H and C1S03H is as sulfonating agents to introduce the -S03H group into various organic materials. 

In all the cases described above, the sulfonating agent, SO3 gas, is usually prepared on site by burning sulphur to S02, followed by subsequent conversion to S03 using a standard V205 catalytic converter. 

A special sulfonation technique is also used for the production of sulfosuccinates (Fig. 1.16). These are derived from maleate esters or half esters using a suitable sulfonation agent, most commonly sodium metabisulfite. 

Allcock s research led to the development of poly-phosphazene-based PEMs by his small molecule studies of the sulfonation of cyclic trimeric phosphazenes and the surface chemistry of polyphosphazene macromolecules. In a 1993 report, he described the sulfonation of aminophosphazenes with 1,3—propanesultone. While these specific materials are not necessarily ideal as PEMs, this study demonstrated a novel technique for creating sulfonated polyphosphazene materials that may provide more control over the sulfonated polymer product than wholesale sulfonation of a base polymer by a strong sulfonating agent. 

Earle and Katdare reported a process for the sulfonation of an aromatic compound in the presence of an IL. The method for the sulfonation of aromatic compounds in water-stable ILs offered advantages over conventional sulfonation reactions (1) no by-products were formed (2) the IL was not consumed, and (3) the sulfonating agent (e.g., SO3) was relatively inexpensive. 

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