4- hydroxyalkanal alkanal

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]. 

Applications. In 1994 ca. 305 10 " t of liquid sulfur dioxide was consumed just in the USA, of which 40% was utilized in the manufacture of sulfur-containing chemicals such as sulfites, hydrogen sulfites, thiosulfites, dithionites and salts of hydroxyalkane sulfinic acid and alkane sulfonates. It is also utilized in cellulose manufacture, in the chemical dressing of manganese ores, in the removal of sulfur-containing impurities from mineral oils, for disinfection and preservation in the food industry and for the treatment of water. 

Replacing a hydrogen atom in any of the methylene groups by a hydroxide function significantly reduces the retention time. The position of the hydroxide function exerts a noticeable influence on the resulting retention time. Fig. 5-35 shows the separation of two Ci6-hydroxyalkane sulfonates, which are hydroxy-substituted in the 2- and 3-pos-ition of the alkyl chain. In comparison to non-substituted alkane sulfonates, the retention decrease corresponds to the loss of 2 to 3 methylene groups from the solvophobic alkyl groups. 

Fig. 5-35. Separation of two hydroxyalkane sulfonates with different hydroxide group position. — Separator column IonPac NS1 (10 pm) eluent 0.01 mol/L NH4OH / acetonitrile (62 38 v/v) flow rate 1 mL/min detection suppressed conductivity injection volume 50 pL solute concentrations 100 ppm each of C 14-alkane sulfonate (2-hydroxy) (1), C16-alkane sulfonate (3-hydroxy) (2), and C16-alkane sulfonate (2-hydroxy) (3).

Sodium C12-14 olefin sulfonate CAS 85536-12-5 EINECS/ELINCS 287-492-2 Synonyms Sulfonic acids, C12-14-alkane hydroxy and C12-14-alkene, sodium salts Definition Mixt. of long chain sulfonate salts from sulfonation of C12-14 alpha olefins consists of sodium alkene sulfonates and sodium hydroxyalkane sulfonates Uses Surfactant in cosmetics food-pkg. 

Synthesis of S-Hydro alkanals. The lithio derivative of (1) reacts with terminal epoxides to give ring-opened products. Reductive desulfurization followed hy acidic deprotection forms 5-hydroxyalkanal, which cyclizes to give a 5-lactol (eq 4). ... 

Commonly employed base hydrolysis of sultones at 150 C leads to about 60-70% hydroxyalkane sulphonate and 30-40% alkane sulphonate. 

Many monosulphonates can be extracted from 3 M hydrochloric acid with diethyl ether. Disulphonates and hydrotropes which are low-molecular-weight sulphonates are not extracted. In the case of a-olefin sulphonates the hydroxyalkane sulphonates are converted to sultones and extracted with the monosulphonic acid. The method is applicable to alkylbenzene sulphonates, mono- and dialkylsulphosuccinates and a-olefin sulphonates, but apparently not to alkane sulphonates. 

As a check, the sum of the alkene sulphonates and hydroxyalkane sulphonates in mol/1 may be determined on the original sample by titration with benzethonium chloride. The result includes any 2-hydroxy-alkane sulphonate, which is not converted to the sultone by the acid treatment described, and so may differ slightly from the sum of the... 

The major sulfonation process uses sulfur trioxide as the reactant and yields alkene sulfonic acids as preliminary products, together with various sultones (mainly 1,3 and 1,4 sultones corresponding to the more probable positions of the intermediate carbonium ion in the successive molecular rearrangements). Further alkaline hydrolysis of sultones yields hydroxyalkane sulfonates and alkene sulfonates (illustrated belo for 1,3 alkane sultone). An acidic hydrolysis of sultones produces alkene sulfonates as major products. 

---