Secondary alkanesulfonates

Workup of the complex reaction mixture was difficult and expensive. As a result, these surfactants have been withdrawn from the U.S. market. In Europe, Hoechst AG produces secondary alkanesulfonates by a similar reaction (eq. 12) ... 

The carbon number distribution of technical secondary alkanesulfonates determined by pyrolysis gas chromatography and mass spectrometry (GC-MS) is shown in Fig. 13 together with the corresponding carbon number pattern of the raw material paraffins obtained by GC [16]. Pyrolysis was performed in a crucible-modified SGE pyrojector after covering the mixture with quartz wool. The presence of up to 10 wt % of disulfonates in technical alkanesulfonates is demonstrated by fast atom bombardment and mass spectrometry (FAB-MS) (Fig. 14) [24],... 

To quantify trace amounts of secondary alkanesulfonates in environmental matrices such as sewage treatment plant effluents and sludges, various cleanup procedures and subsequent thin-layer chromatography (TLC) and GC-MS determinations were developed [24]. 

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... 

The procedure for the determination of total secondary alkanesulfonates with TLC and of total monosulfonates specified as homologs and isomers by derivatization GC-MS is shown in Fig. 18. The specific clean-up for sewage sludges prior to total secondary alkanesulfonate determination is outlined in Fig. 19. TLC conditions are given in Table 9. The limits of the quantification of secondary alkanesulfonates are summarized in Table 10. For eight samples and one operator the TLC time schedule is 4 days sample pretreatment and sublation, clean-up, TLC performance, and quantitative evaluation of TLC [24]. 

Examples comparing the secondary alkanesulfonate content of influents and effluents of various sewage treatment plants with the concentrations of linear alkylbenzenesulfonates are shown in Table 12. In sludges the specimen secondary alkanesulfonate (linear alkylbenzenesulfonate) concentration of less than 0.1... 

To put these data in perspective, it is important to point out that they merely imply an exhaustive biodegradation of secondary alkanesulfonates and do not represent monitoring results. 

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-... 

TABLE 12 Secondary Alkanesulfonates (SAS) and Linear Alkylbenzenesulfonates (LAS) in Sewage Treatment Plant Influents and Effluents (pg/L)... 

FIG. 26 ct-c Isotherms at 22°C for secondary alkanesulfonates purified by chemical interfacial procedures, x, Sodium pentadecane 4-sulfonate O, sodium pentadecane 8-sulfonate). The curve is fitted by the Frumkin isotherm with = 3.95 x 10, ° mol/cm2 and aF = 5.20 x 10 5 mol/dm3... 

The performance of secondary alkanesulfonates in applications as emulsifiers in the widespread emulsion polymerization of vinyl monomers can be assessed by their hydrophilic-lipophilic balance (HLB) numbers. The HLB numbers can... 

Advantages of secondary alkanesulfonates which recommend them for a great variety of formulations are the following ... 

Due to the solubility mentioned, the market segment that prefers to use secondary alkanesulfonates is liquid detergents and concentrates. 

APG, alkyl polyglucoside FAA, fatty acid alkanolamide FAEO, fatty alcohol ethoxylate FAES, fatty alcohol ether sulfate FAGA, fatty acid glucamide FAS, fatty alcohol sulfate LAS, linear alkylbenzenesulfonate SAS, secondary alkanesulfonate. 

Secondary alkanesulfonates are also used as potent surfactants in various cleaner formulations. Some examples are listed in Table 29. Consumer products like cleaners for painting devices or car engines are to be formulated as microemulsions as well (Table 30). 

Because secondary alkanesulfonates are used as mixtures of homologs and sulfo group isomers, ecological and toxicological data are presented for these technical products. If not otherwise indicated, the data reported are based on information of two of the major producers [101,102]. 

Secondary alkanesulfonates are easily biodegradable under aerobic conditions but are less so in an anaerobic environment, a feature common to all sulfonates with the stable carbon-sulfur bond. The recent discussions on anaerobic biodegradation [103] should be put into perspective since in the sewage or deposition path a temporary anaerobic step quickly gives way to a stage where natural conditions, which are aerobic, prevail. Thus, anaerobic biodegradation... 

Information is given for the sulfoxidation-derived paraffin sulfonate Marlon PS and the secondary alkanesulfonate Hostapur SAS. 

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). 

When comparing secondary alkanesulfonates (SAS) and linear alkylbenzene-sulfonates (LAS), it is obvious that SAS are more readily degraded than LAS. This is somewhat more pronounced at lower temperatures (Table 34). 

Some years ago, comparative investigations into the biodegradation of secondary alkanesulfonates using 14C-labeled preparations [106] and radiometric studies of the biodegradation of secondary alkanesulfonates in a sewage plant model [107] are published (Fig. 42). 

In five pilot plants that can be used to simulate the route of anionic surfactants from the consumer via the effluent purification plant to the receiving water, possible toxic effects of residual surfactant content and breakdown products of the secondary alkanesulfonates were investigated [102]. As indicators of the effects on living organisms of the effluent in the receiving water, flora and fauna that are frequently encountered in the p-mesosaprobic zone were used as models. The embryo-larval test was also employed as an additional method for the detection of toxic compounds in the water. 

A slight toxic effect ( toxic defined as negative effects on health, growth, and reproduction) of the treated receiving water on the green alga Spiropyra species as a typical representative of the P-mesosaprobic zone was observed, when the test unit was subjected to the impact of 40 ppm secondary alkanesulfonates. 

The secondary alkanesulfonate tested has no significant toxic effect on Planorbis corneus. 

Secondary alkanesulfonate in effluent has no toxic effect on the fish food organism Daphnia magna. 

Secondary alkanesulfonates are manufactured by the action of sulfur dioxide and air directly on C14-C18 //-paraffins (a sulfoxidation reaction), and the sulfonate group can appear in most positions on the chain. 

Secondary alkanesulfonates (SAS). The large-scale production of sodium alkanesulfonates (SAS) began in the late 1960s. 

These sulfonates are still valued as anionic surfactants for consumer products. The secondary alkanesulfonates are known to have high solubility, fast wetting properties, chemical stability to alkali, acids, and strong oxidants such as chlorine. 

LAS Na+ — commercial sodium C12 benzenesulfonate. b SAS — commercial secondary alkanesulfonate. c AOT Na+ — sodium di(2-ethylhexyl)sulfosuccinate. 

---