Primary alkanesulfonates

Although, historically, not made from fossil fuel material, contrary to Gunther s naphthalenesulfo-nates [6], the C g primary alkanesulfonate (PAS) can be considered as the hrst synthetic surfactant, obtained by Reychler in 1914 through the oxidation of hexadecanethiol [7], Later, Reed and Tartar [8,9] employed the Strecker reaction to prepare PAS in 70% yield. 

Tyutyunnikov, B.N., Kovalev, V.M. and Bukhshtab, Z.I., Factors affecting the preparation of primary alkanesulfonates from a-olefins and sodium bisulfite, Nefterabotka i neftekhimiya, 12,48-50, 1973. 

The simultaneous reaction of sulfur dioxide and chlorine with paraffins, named sulfochlorination, was discovered by Reed and Horn in the 1930s [9]. The primary products of this reaction are the alkanesulfochlorides [10], which can be saponified to alkanesulfonates by sodium hydroxide solution or treated with substituted phenolates to give plasticisers. In a short time the process was industrially realized to secure detergent production during World War II in Germany [11]. 

To determine secondary alkanesulfonates in sewage wastewaters, solid phase extraction (SPE) and a single-step procedure which combines elution and injection port derivatization for analysis with GC-MS were developed [36]. Again a tetrabutylammonium ion pair reagent was employed both to elute the secondary alkanesulfonates as their ion pairs from CI8-bonded silica disks and to derivatize sulfonate ion pairs under GC injection port conditions. Secondary alkanesulfonates were effectively recovered from samples of raw sewage (>92%) and from primary (>98%) and secondary (>85%) effluents. No... 

One field study on the mass flow of secondary alkanesulfonates was conducted in the Zurich-Glatt municipal wastewater treatment plant [37]. The concentration of alkanesulfonates in samples of raw sewage and primary and secondary effluents was analyzed using the above-described SPE with C18 Empore disks and injection port derivatization with GC-MS detection. The con-... 

The primary biodegradation grades of secondary alkanesulfonates measured by different tests are distinctly above 90%. In the OECD Confirmatory Test (sewage treatment plant simulation test), the biodegradability is 99% (decrease in MBAS, the methylene blue active substance). 

C (r-C]x linear primary and secondary alkanesulfonates alkyl chain distribution... 

Cii-Cis alkanesulfonates separation by chain length and primary sulfonate content Merck LiChrosorb RP-8 4.6 x 250 mm MeOH/H20,0.01 M tetrabutylammonium sulfate Refractive index 42 X (a b A... 

Ullner, H., I. Konig, C. Sander, U. Schwenk, LC separation of paraffin sulfonates, with special emphasis on primary paraffin sulfonates (in German), Tenside, 1980,17,169-170. Hauthal, H. G., Alkanesulfonates, in H. W. Stache, ed.. Anionic Surfactants Organic Chemistry, Marcel Dekker, New York, 1996. 

Primary C12 and Cig alkanesulfonates are commercially available, absent from ordinary detergents, and therefore suitable as internal standards in alkanesulfonate analysis (43,68). 

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