July 7, 1922] 



SCIENCE 



57 



with malonic ester with either one or both groups. 

 The amino group is first substituted. The 

 methylene hydrogen atoms of the malonic residue 

 in this compound are easily replaced by chlorine. 

 Sodium ethylate and alcohol react with this to 

 form "diehloracetyl of ortho-amino-cyolohex- 

 anol. ' ' The reaction product between amino- 

 cyclohexanol and malonic ester in which both 

 groups react with the ester at a high temperature 

 reacts in such a manner that two molecules 

 combine with an aeetal linkage. 



The alJcylation of aniline: A. B. Bkown and 

 E. Emmet Keid. Mixtures of aniline vapor with 

 methyl, ethyl, propyl and butyl alcohols have been 

 passed over special silica gel at from 300 to 450°. 

 This substance is an efficient catalyst for this 

 reaction, though its activity falls off with time. 

 In all cases the product is chiefly the monoalkyl 

 derivative. The optimum temperature is from 36.5 

 to 395°. At the start 43 to 51 per cent, of alkyl 

 anilines are produced with one equivalent of the 

 alcohol and 68 to 70 per cent, with two equiva- 

 lents, except in the case of butyl alcohol, where an 

 excess is of little advantage. 



The amination of alcohols: A. B. Brown and 

 E. Emmet Reid. An extensive study has been 

 made of the conversion of methyl, ethyl, propyl 

 and butyl alcohols into the corresponding amines 

 by passing their vapors mixed with ammonia over 

 various catalysts at different temperatures up to 

 500°. The optimum temperatures and percentages 

 of the primary, secondary and tertiary amines 

 formed have been determined for the different 

 catalysts. The best catalyst so far found is a 

 specially prepared silica gel. 



The alkylation of ie-nzene: T. M. Berry and 

 E. Emmet Reid. Continuing the work of Milligan 

 and Reid, a more thorough study has been made of 

 the alkylation of benzene by ethylene and pro- 

 pylene in the presence of aluminum chloride. The 

 proportion of the alkylated benzenes in the two 

 layers has been specifically investigated. It has 

 been found that the higher alkylated benzenes, ex- 

 cept the hexa-, are concentrated in the lower layer, 

 which also contains almost all of the aluminum 

 chloride. The absorption of propylene is relatively 

 slow but continues till the tetra- product, at least, 

 is formed. 



Ditolyl ketene: Henry Gilman and Chester 

 E. Adams. Several unsuccessful attempts have 

 been made by others to synthesize this ketene. 

 Azitolil, prepared by the oxidation of mono- 

 hydrazi tolil, loses nitrogen when heated in ben- 

 zene at 75 to 80° C, rearranging to the desired 

 ketene. In addition to its general interest as a 



new type it is being used in connection with an- 

 other study. 



The effect of an "iso" grouping on the melting 

 and foiling points of organic compounds belong- 

 ing to various classes: F B. Flick, H. M. Craw- 

 rORD, E. Hoyle and H. Oilman. In connection 

 with some work on the structure of tetra-tolyl 

 ethylene, a substance with an apparently "ab- 

 normal ' ' melting point, a regularity in the boiling 

 points of ethylenic hydrocarbons having an "iso" 

 group was observed. The study extended to other 

 classes of compounds having an "iso" grouping 

 revealed certain regularities, some of which might 

 have been forecasted. 



Physiolo^cal action and chemical constitution: 

 the replacement of the benzoyl ly related aoyl 

 groups: Henry Oilman and Russell M. Pick- 

 ens. A number of organic acids, aromatic and 

 aliphatic, are related in different ways to benzoic 

 acid. The physiological behavior (the present 

 study concerns local anesthetics) of derivatives of 

 these acids is being compared. The diethylamino- 

 ethyl and the benzyl esters of pyromueic, furyl 

 acrylic and alpha-thienoie acids are described. 



Arsenated henzanilide and its derivatives: 

 W. Lee Lewis and C. S. Hamilton. Diehloro- 

 p-arsinobenzoyl chloride was prepared according 

 to the method of Lewis and Cheetham and con- 

 densed with various amines. With aniline there 

 resulted p-arsonobenzanilide which, on reduction, 

 gave p-arseuo-benzanilide. Similarly there were 

 made p-arsono-benzanthraniUde and -anisidide and 

 the arseno derivative of the latter. Further deriv- 

 atives prepared are the following: p-arsono- 

 benzoyl-p-phenetidide, its arseno derivative, di- 

 iodo-p-arsino-benzoyl-p-phenetidide, p-arseno-ben- 

 zoyl-p-xylidide, p-arseno-benzoyl-alpha-naphthyl- 

 amide, and p-arsouoso-benzoyl-arsanilide. 



Arsenated tenzophenone and its derivatives: 

 W. Lee Lewis and H. C. Cheetham. A previous 

 paper by the authors dealt with the condensation 

 of di-chloro-p-arsinobenzoyl chloride with aro- 

 matic hydrocarbons and phenyl ethers in the pres- 

 ence of anhydrous aluminum chloride. In the 

 present paper the work has been extended to 

 include the preparation of the following: aeeto- 

 phenone-p-arsonic acid, o-earboxyphenyl arsonic 

 acid, dichloro-o-arsinobenzoyl chloride, 4-methyl- 

 benzophenone-2'-arsonic acid, 4-ethoxy-benzo- 

 phenone-2'-arsonic acid, 4, 4'-dibenzoyl-arseno- 

 benzene, 4-methoxy-benzophenone-2'-arsonic acid, 

 4-methoxy-benzophenone-2'-arsenous acid, 4-ethoxy- 

 benzophenone-2'-dibromo-arsine, 4-methoxy-benzo- 

 phenone-2'-dichloro-arsine, 4-methoxy-benzophen- 

 one-2'-diiodo-aTsine, 4-ethoxy-benzophenone-2'-di- 



