Naphthalene, alkylation derivatives, sulfonation

The analogous alkyl derivatives of toluene, xylene, and lower alkyl naphthalenes are included in the vast number of alkyl aromatics which are also described in the literature as sulfonation stocks (16). While several sulfonates derived from such products have enjoyed partial success, they have limitations with respect to yield, sudsing, and handling characteristics which place them at a disadvantage with respect to the alkyl benzenes described above. 

The raw materials used to synthesize organic dyes are commonly referred to as dye intermediates. Largely, they are derivatives of aromatic compounds obtained from coal tar mixtures. The majority of these derivatives are benzene, naphthalene, and anthracene based compounds. This section provides an overview of the chemical reactions used to prepare the key intermediates employed in dye synthesis. In this regard, emphasis is placed on halogenated, aminated, hydroxy-lated, sulfonated, and alkylated derivatives of benzene, naphthalene, and anthraquinone. 

Sulfonic acid Isomer distribution data for the SO3 sulfonation are available for alkylbenzenes and their halogeno derivatives phenol and anisole, and their methyl, halogeno, and hydroxy and methoxy derivatives and naphthalene, and Its methyl, and hydroxy and methoxy derivatives. SO3 sulfonation Isomer distribution data are also available for a number of polycyclic aromatic hydrocarbons and 1,6-methano[10]annulenes, including some alkyl derivatives. ... 

There are three main uses for naphthalene sulfonic acid derivatives (75—79) as naphthalenic tanning material alkyl naphthalene sulfonates for industrial appHcations as nondetergent wetting agents and as dye intermediates. Consumption of naphthalene sulfonates as surfactants accounts for a large portion of usage. Naphthalene sulfonate—formaldehyde condensates are also used as concrete additives to enhance flow properties. Demand for naphthalene sulfonates in surfactants and dispersent appHcations, particularly in concrete, was expected to increase into the twenty-first century. Consumption as of 1995 was 16 x 10 kg/yr. 

The dansyl derivative 9-azidononyl-5-(dimethylamino)naphthalene-l-sulfonate 35 was used by Yi and collaborators [91] as an azido-fluorescent label in a tandem method of sulfonium alkylation and click chemistry for the modification of biomolecules. Fluorescent labeling of a protein was successfully carried out after simple incubation of BSA with sulfonium salt 36 followed by azido-containing fluorophore 35, at room temperature. 

Poly(amino acids)2892 and polypeptides2893 can also be grafted onto starch. Starch was first alkylated in the presence of lithium naphthalene, and then the alkoxy derivatives were reacted with /V-carboxy anhydrides. Poly(amide amines) were produced by reacting amines with dioic acids on starch and then crosslinking with epichlorohydrin or 1,2-dichloroethane 2894 Grafting of starch with a synthetic polymer chain, for instance, polystyryl carboxylate anions prepared by an anionic polymerization, can be carried out on a blend of starch and cellulose functionalized by sulfonation, mesylation, or tosylation. In this manner, cellulose-starch graft copolymers were prepared.2895... 

---