1- -2,5- arenecarboxylic acid

Retarders were originally arenecarboxylic acids. These acidic materials not only delay the onset of cross-linking but also slow the cross-linking reaction itself. The acidic retarders do not function weU in black-fiUed compounds because of the high pH of furnace blacks. Another type of retarder, A/-nitroso diphenylamine [86-30-6] was used for many years in black-fiUed compounds. This product disappeared when it was recognized that it trans-nitrosated volatile amines to give a several-fold increase in airborne nitrosamines. U.S. production peaked in 1974 at about 1.6 million kg. 

Carboxamides and esters of arenecarboxylic acids are obtainable directly by reacting arenediazosulfones (Ar — N2 —S02 —Ar ) with CO and amines or alcohols, respectively, in the presence of Pd catalysts (Kamigata et al., 1989). Aromatic aldehydes are formed if the reaction is carried out in the presence of triethylsilane (Kikukawa et al., 1984). In an analogous way, arenediazonium salts can be transformed into ketones (ArCO —R R = CH3, C2H5, or C6H5) in the presence of stan-nanes, R4Sn (Kikukawa et al., 1982). 

These quinoxalinylalkyl esters of aUcane- or arenecarboxylic acids are sometimes used as intermediates (see, e.g.. Section 3.4.2). The formation of an analogous quinoxalinylmethyl nitrate is included in this section. Examples follow. 

---