314 



SCIENCE 



[N. S. Vol. XXIX. No. 738 



are usually described as " catalytic," but it is 

 obviously very difficult in many eases to distin- 

 guish between a " catalytic " influence and one 

 due only to an alteration in tbe thermal properties 

 of the surface of the container. In the hope of 

 throwing some light on the subject we have in- 

 vestigated the production of benzophenone by the 

 distillation of calcium benzoate in a current of 

 carbon dioxide. The calcium salt was mixed 

 intimately with the substances mentioned below, 

 the figures give the percentage yield of benzophe- 

 none. Unglazed porcelain, 30.4; carbon from arc 

 light rods, 40.9; iron filings, 45.0; calcium car- 

 bonate and iron filings, 54.5; calcium carbonate 

 and arc light rods, 50.0. These results are the 

 mean of closely agreeing duplicates and express 

 the yield percentage of the theoretical. The yield 

 of benzophenone from benzene, aluminium chlo- 

 ride and benzoyl chloride is 42.8 per cent., accord- 

 ing to Gattermann. 



Studies in Nitration — TI., Synthesis of Certain 

 Nitranilides : J. Bishop Tingdb and 0. E. 



BUBKE. 



Work is in active progress on the synthesis of 

 a number of nitrophenylamides, nitrophenylimides 

 and nitrophenylamidic acids from o-, m- and p- 

 nitraniline. In this manner it is hoped to identify 

 some of the many compounds prepared by the 

 senior author and Dr. P. C. Blanck by the nitra- 

 tion of the corresponding aniline derivatives. A 

 description of the individual compounds thus far 

 synthesized will appear in due course. 

 Aniline Derivatives of Certain Unsaturated Di- 



hasic Acids of the Aliphatic Series: J. Bishop 



Tingle and S. J. Bates. 



It has been shown by the senior author and his 

 collaborators that succinanilic acid, C5H5KHCOCH2- 

 CH2CO2H, when treated with aniline yields succin- 

 dianilide, C8H„NHCOCHjOH,CONHC„H„ whereas 

 phthalanilic acid, CsH^NHCOCaH^CO^H, under 

 similar conditions is converted into the anil. 



The investigation has now been extended to the 

 aniline derivatives of maleic, fiunaric and malic 

 acids. Several new compounds have been pre- 

 pared. A study is being made of the action of 

 various amines on fumar-, male- and malanilic 

 acids, 



HCCO.H HCCO2H 



C,H.NHCOCH HCCONHCeH, 



and CaHjNHOOCHlOHjCHjCOaH, respectively. 



Rearrangement in the Phthalamidio Acid Series — ' 

 IV.: J. Bishop Tingle and B. F. Pablett 

 Beenton. 



The work of Bishop Tingle and his collaborators 

 on this subject has been extended. Phthaldi- 

 phenylamidic acid, (CoHtJ^NCOCaHjCO^H, when 

 heatea with pyridine at 100° gives dipyridinium 

 phthalate, in 109°. Aniline transforms tue acid 

 into phthalanil, 



whereas by the action of ;3-naphthylamine a mix- 

 ture of phthalanil and phthal-j3-naphthylamidic 

 acid, CioHiNHCOCeHiCOjH, is obtained. The fol- 

 lowing new acids have been prepared by the 

 method described recently by Bishop Tingle and 

 Eolker.^ A study is being made of the action on 

 them of various amines. Phthalphenyl-p-naphthyl- 

 amidio acid, CeHoN(Ci„H,) COCaH^COoH, m. 115°. 

 Phthal-p-ohlorphemylamidio add, ClCoHiNHCOCe- 

 H4CO2H, m. 180°. Phthaldiisohutylamidio add, 

 [(CH3)2CHCH2]2NC0CaH.C02H, m. 153°. The 

 product from diisoamylamine was tarry. Ethyl- 

 aniline and methylaniline yielded the diamides 

 CeH.[CON(CeH5)aH,],andUaH,[CON(CaH5)CH,]„ 

 respectively, m. 144° and 181.5°. Two compounds 

 have been prepared from benzidine and phthalic- 

 anhydride, both melt only at high temperatures^ 

 One appears to be the diamide or imide. 



/CO.NH.CeH, 



CO.l 

 or 



/C0\ 

 C.H.<^^^^NG„H. . CeH.NH,. 



The other has not yet been investigated, p-amino- 

 benzoic acid gives the dibasic acid, HOaCCoH,- 

 CONHC„H,CO;iH, m. 271°. 



The action of carbamide and its substitution 

 products on phthalic anhydride has been made. 

 It is found to take place according to the equation, 



CO 



co' 



;eH.<^o 



+ RHNC0NH3 



-»C,H. 



j\ 



COv 



> 



CO/ 



\co 



NR + NH3 + CO2, 



The compounds produced when 11=: H, CaH„ 

 CoHjCHj, CHs and CjHb have been investigated. 

 Phenythiocarbamide behaves in a similar manner, 

 NH3 and COS being evolved. Ethylidenecarbamide 



^Jour. Am. Ghem. Soc, 30, 1882, 1908. 



