A New Reaction of Sulfanilamide WILLARD T. SOMERVILLE, Elrnhmst, Long Island
ULFANJLAMIDE (4-aminobenzenesnlfonamide) S produces a beautiful bright orange coloration with substances containing lignin. This reaction
Manila hemp and sisal fibers are very similar and i t is quite difficult to distinguish between them. In the above table i t is clearly shown that the sulfanilamide affords a simple means of determining the presence test affords a simple means of differentiation. The reagent used was a two per cent aqueous solution of lignin in paper, wood, and various vegetable fibers. This so-called "hadromal" color reaction has been of sulfanilamide containing one per cent concentrated observed by several other investigators. Benzidine hydrochloric acid. The color develops within thirty ( I ) , tolidine (Z), qninoline (3), 2,6-diaminopyridine seconds to one minute. In a series of mixtures of (B), sulfanilic acid (5), meta nitro phenol (5), ortho ground wood and bleached sulfite pulp graduated and para toluidines (7), aniline (lo), and alpha naph- shades were obtained which were easily dserentiated thylamine have been reported to give colored com- with the exception of the 90, 95, and 100 per cent mixtures. In these the difference was too small to be pounds in the presence of liguin. This reaction is not due to lignin itself, as lignin visible. The colors are much stronger and more which has been subjected to the action of a mild oxidiz- easily differentiated than the pale yellow shades ing agent in dilute solution loses its power to produce obtained with aniline sulfate. With dilute sodium the reaction. It is generally believed that the re- hydroxide the color produced is changed to a pale action is caused by minute traces of a substance in- yellow. The sulfanilamide hydrochloride reagent is quite variably accompanying lignin (5, 6). Klason (8) states that the "lignin" reactions with amines are stable and does not oxidize or discolor when kept for true aldehyde reactions. Spectroscopic examination extended periods of time. In this respect i t is superior indicates that there is one predominating color-produc- to other reagents of this type. ing aldehyde in wood and that this is coniferyl aldehyde. CONCLUSIONS The reaction between vanillin, which is chemically A new color reaction between sulfanilamide and an similar to coniferyl aldehyde, and sulfanilamide leads aldehyde accompanying lipin is described. lts to the formation of an mil (9). The componnd from in distinguishing between fibers and detecting ground sulfanilamide and coniferyl aldehyde, the orange wood in papers is indicated. Manila hemp and sisal compound formed in the reaction, may be formulated are easily identified. The reaction produced with as follows : sulfanilamide is more satisfactory than the aniline sulfate test, because the color is stronger and more easily recognizable.
(ioCH,
LITERATURE CITED
In the following table various substances are classified as to their reaction with the sulfanilamide reagent. Wood
Mechanical wood pdp Unbleached sulfite (very faint reaetion*a1e yellow) Straw Sisd (yellow color) Cornnut fiber Jute
Bleached sulfite pulp Bleached rode pulp Bleached rae
Raffia Hemp Cotton (bleached and unbleached)
Linen
(1) V m ZIIP, Pharm. Weekblad, 58, 153942 (1921). ibid., 70,286-90 (1933). (2) WAGENAAR, Atti eccad. Lincei. 17, 469-73 (1933); (3) CASTAROGLIONI, C. A,, 27, 5031 (1933). (4) SCHICKH, Svensk Pappers-Tan., 39,276 (1936). (5) CROCIKER, Ind.Eng. Chem.. 13,625-7 (1921). Paperi-Fabr., 37, Tech.-wiss. TI.,17-24, 30-1 (6) WIECHART, (1939); C. A., 33, 3146 (1939). (7) CZAPEK, Z. anal. Ckcnz., 38,715 (1899). (8) KLASON, Ber., 63B, 1981-3 (1930). SEVERAC, AND MOETSCH, 94th meet(9) RAIZISS,CLEMENCE, ing of the A. C. S.. Rochester, New York (1937). Z. physiol. Chcm., 27, 141 (1899). (10) CZAPEK,
