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Azo dyes from alkaloids of ipecac root and their identification by means of the spectroscope
N O T E S F R O M T H E U. S. B U R E A U OF C H E M I S T R Y . * THE
PREPARATION OF 2-AMINOANTHRAQUINONE PHTHALIC ANHYDRIDE AND CHLOROBENZENE.
FROM I
By Max Phillips.
[.~STRACT.] IH THE preparation of chlorobenzoylbenzoic acid from phthalie anhydride, chlorobenzene, and aluminum chloride, the most favorable yield is obtained when the molal ratio of phthalic anhydride to aluminum chloride is I : I . To carry out this preparation successfully an excess of chlorobenzene should be used, about 4 to 5 mols to I tool of phthalic anhydride. The optimum reaction temperature is IOO° C. The yield of chlorobenzoylbenzoic acid is about 77 per cent. of the theoretical. The conversion of chlorobenzoylbenzoic acid into 2-chloroan,thraquinone may be brought about by heating it at 15 °° C. for four hours with sulphuric acid (specific gravity 1.84). The yield is practically quantitative--97 per cent. of the theoretical. The various experiments on the preparation of 2-aminoanthraquinone from 2-chloroanthraquinone indicate that the optimum experimental conditions are as follows: Temperature, 220 ° C.; reaction period, six hours; concentration of ammonia with respect to 2-chloroanthraquinone, 20: I, although a 15:1 ratio gave nearly as good results. The 2-aminoanthraquinone obtained under these conditions is 95 per cent. pure and the yield is 91 per cent. of the theoretical. The addition of catalysts, such as copper sulphate or copper powder, to the reaction mixture is undesirable. AZO DYES FROM A L K A L O I D S OF IPECAC ROOT AND T H E I R I D E N T I F I C A T I O N BY M E A N S O F T H E S P E C T R O S C O P E . 2 By S. Palkin and H. Wales.
[ASSTI~CT.] A METHOD for the identification of phenols described in a recent paper has been extended to apply to certain alkaloids of ipecac. Azo dyes from these alkaloids of ipecac have been pre* Communicated by the Chief of the Bureau. Published in Ind. Eng. Chem., 17 (July, 1925) : 72I. Published in J. Am. Chem. Soc., 47 (July, 1925) :2o05. 393
394
U.S.
BUREAU OF CHEMISTRY NOTES.
[J.F.I.
pared and measurements made of their absorption spectra in three different solvents. A number of characteristic curves have been thus obtained for cepha~line and emetamine, the absorption spectra of which can be used for their positive identification, even in the presence of a considerable quanti,ty of other drugs, if not unduly complicated by interfering substances. E F F E C T O F T E M P E R A T U R E A N D T I M E O F S T O R A G E ON THE PHYSICAL PROPERTIES OF UNDEVELOPED BROWN PRINT PAPER? By T. D. Jarrell and F. P. Veitch.
[ABS~RACr.] COATERS and users of brown print paper should keep undeveloped sensitized paper at a temperature not higher than 35 ° to 4 °0 F. in order to conserve its durability. The effect of the commonly employed brown print sensitizing materials on the folding endurance, bursting, and wet tensile strength of paper was investigated. At intervals of one to twenty weeks after storing the undeveloped coated rolls of paper at 35 ° to 40 ° F., 55 ° to 60 ° F., 70 ° F., and 86 ° F., samples were taken from the various rolls, and developed, washed, and air dried. The physical tests made on these samples showed that the temperature at which undeveloped coated brown print paper is kept between the period of coating and drying and the time of developing and washing influences the effect of the sensitizing materials upon the physical properties of the paper. Undeveloped brown print paper can be kept at 35 ° to 4 °0 F. for at least five months without any deterioration in strength. As the temperature increases, however, the deterioration becomes marked. When stored for two weeks at 55 ° to 60 ° F. the folding endurance is decreased about 3o per cent., and the bursting strength is decreased about 5 per cent. The folding endurance and bursting strength are decreased about 45 per cent. and 8 per cent., respectively, when stored for two weeks at 7°0 F. When stored for two weeks at 86 ° F. the folding endurance is decreased about 80 per cent., and the bursting strength is decreased about 20 per cent. As the period of storing the undeveloped coated Published in Paper Trade Y., 8o (May I4, t925) : 56.
PREPARATION OF 2-AMINOANTHRAQUINONE PHTHALIC ANHYDRIDE AND CHLOROBENZENE.
FROM I
By Max Phillips.
[.~STRACT.] IH THE preparation of chlorobenzoylbenzoic acid from phthalie anhydride, chlorobenzene, and aluminum chloride, the most favorable yield is obtained when the molal ratio of phthalic anhydride to aluminum chloride is I : I . To carry out this preparation successfully an excess of chlorobenzene should be used, about 4 to 5 mols to I tool of phthalic anhydride. The optimum reaction temperature is IOO° C. The yield of chlorobenzoylbenzoic acid is about 77 per cent. of the theoretical. The conversion of chlorobenzoylbenzoic acid into 2-chloroan,thraquinone may be brought about by heating it at 15 °° C. for four hours with sulphuric acid (specific gravity 1.84). The yield is practically quantitative--97 per cent. of the theoretical. The various experiments on the preparation of 2-aminoanthraquinone from 2-chloroanthraquinone indicate that the optimum experimental conditions are as follows: Temperature, 220 ° C.; reaction period, six hours; concentration of ammonia with respect to 2-chloroanthraquinone, 20: I, although a 15:1 ratio gave nearly as good results. The 2-aminoanthraquinone obtained under these conditions is 95 per cent. pure and the yield is 91 per cent. of the theoretical. The addition of catalysts, such as copper sulphate or copper powder, to the reaction mixture is undesirable. AZO DYES FROM A L K A L O I D S OF IPECAC ROOT AND T H E I R I D E N T I F I C A T I O N BY M E A N S O F T H E S P E C T R O S C O P E . 2 By S. Palkin and H. Wales.
[ASSTI~CT.] A METHOD for the identification of phenols described in a recent paper has been extended to apply to certain alkaloids of ipecac. Azo dyes from these alkaloids of ipecac have been pre* Communicated by the Chief of the Bureau. Published in Ind. Eng. Chem., 17 (July, 1925) : 72I. Published in J. Am. Chem. Soc., 47 (July, 1925) :2o05. 393
394
U.S.
BUREAU OF CHEMISTRY NOTES.
[J.F.I.
pared and measurements made of their absorption spectra in three different solvents. A number of characteristic curves have been thus obtained for cepha~line and emetamine, the absorption spectra of which can be used for their positive identification, even in the presence of a considerable quanti,ty of other drugs, if not unduly complicated by interfering substances. E F F E C T O F T E M P E R A T U R E A N D T I M E O F S T O R A G E ON THE PHYSICAL PROPERTIES OF UNDEVELOPED BROWN PRINT PAPER? By T. D. Jarrell and F. P. Veitch.
[ABS~RACr.] COATERS and users of brown print paper should keep undeveloped sensitized paper at a temperature not higher than 35 ° to 4 °0 F. in order to conserve its durability. The effect of the commonly employed brown print sensitizing materials on the folding endurance, bursting, and wet tensile strength of paper was investigated. At intervals of one to twenty weeks after storing the undeveloped coated rolls of paper at 35 ° to 40 ° F., 55 ° to 60 ° F., 70 ° F., and 86 ° F., samples were taken from the various rolls, and developed, washed, and air dried. The physical tests made on these samples showed that the temperature at which undeveloped coated brown print paper is kept between the period of coating and drying and the time of developing and washing influences the effect of the sensitizing materials upon the physical properties of the paper. Undeveloped brown print paper can be kept at 35 ° to 4 °0 F. for at least five months without any deterioration in strength. As the temperature increases, however, the deterioration becomes marked. When stored for two weeks at 55 ° to 60 ° F. the folding endurance is decreased about 3o per cent., and the bursting strength is decreased about 5 per cent. The folding endurance and bursting strength are decreased about 45 per cent. and 8 per cent., respectively, when stored for two weeks at 7°0 F. When stored for two weeks at 86 ° F. the folding endurance is decreased about 80 per cent., and the bursting strength is decreased about 20 per cent. As the period of storing the undeveloped coated Published in Paper Trade Y., 8o (May I4, t925) : 56.