494 



SCIENCE 



[Vol. LVI, No. 1452 



sesquicolopliene, (CioHii;)3, and the dicolophene, 

 (CiqHi(;)4. The properties of the latter resemble 

 the former in their remarkable stability and in 

 the difficulty with which they form derivatives. 



Some sulfonic acid esters of plienylasophenol 

 and its substitution derivatives: C. E. Boord, 

 M. D. Coulter and Helen L. Wikopp. (Lan- 

 tern). Several esters of benzene sulfonic acid, 

 p-toluene sulfonic acid and alpha naphthalene 

 sulfonic acid with phenylazophenol and its sub- 

 stitution products were prepared by the Bau- 

 mann-Schotten method. The twentj^-one esters 

 thus prepared for the first time, together with 

 the fourteen previously described (Be)-., 28, 800, 

 31, 1782, 2116; J. Fr. Ch., 78, 386), are all sta- 

 ble, easily purified, beautifully crystalline com- 

 pounds melting between .50° and 200°. It is sug- 

 gested that this type of derivative may be of 

 value in characterizing the sulfonic acids. The 

 para derivatives such as p-tolj'lazophenol and 

 p-chlorophenylazophenol seem best adapted to this 

 purpose. 



Practical preparation of oxalic acid from 

 acetylene: Sister Mary Ltjcretia, Leo J. 

 HEtSER and J. A. Nieuwland. Oxalic acid can 

 bo prepared on a practical scale by passing 

 acetylene into a mixture containing three vol- 

 umes of nitric acid to one volume of water and 

 about two per cent, mercuric nitrate. The forma- 

 tion and loss of nitrogen oxides in the reaction 

 prevents the commercial use of the process. The 

 reaction proceeds through the formation of an 

 intermediate compound which yields aldehyde, 

 which is then oxidized to oxalic acid. Oxalic acid 

 can be prepared by the direct action of nitrogen ■ 

 oxides on acetylene, by the action of aeetaldehyde 

 with nitric acid (3 : 1), and by the action of 

 nitrogen oxides on aldehyde vapor. Aeetaldehyde 

 can be prepared by the action of acetylene on dry 

 mercuric nitrate, by the action of acetylene on 

 the compound obtained by treating metallic mer- 

 cury with nitrogen oxides. 



The oxidation of propylene glycol with lithium, 

 sodium, and potassium permanganates: E. C. 

 Hytree and W. L. Evans, (a) Propylene glycol 

 is oxidized by neutral permanganate solutions to 

 carbon dioxide and acetic acid at 25° and 50°. 

 Above certain minimum concentrations of alkali 

 oxalic acid is also obtained. (6) The amount of 

 each oxidation product at low alkalinities is influ- 

 enced not only by the concentration of the alkali, 

 but also by the use of either lithium, sodium and 

 potassium hydroxides in connection mth each of 

 the several permanganates. 



Hexabromodiphenyldisulfide : W. H. Hunter 



and A. H. Kohlhase. This compound is ob- 

 tained bj' treating the silver salt of tribromothio- 

 phenol with iodine in benzene solution. This ac- 

 tion is normal, and by so much is contrary to the 

 action of iodine on the salts of halogenated 

 phenols to form polyphenylene oxides. Further, 

 molecular weight determinations . in various 

 solvents give consistently low results, apparently 

 showing dissociation of the sulbstance and conse- 

 quent existence of the free radical CgHoBrsS, 

 which does not lose halogen spontaneously. 



Formation of goumaric acids and substituted 

 gamma-butyric acids from resordnol, orciTWl and 

 phloroglucinol : W. D. Langlet and Eoger 

 Adams. While attempting to prepare certain 

 complex ketones, it was found that beta^chloro- 

 propionitrile and gamma-ehlorobutyronitrile do 

 not condense with resorcinol, orcinol or phloro- 

 glucinol in the presence of zinc chloride and 

 hydrogen chloride as nitriles ordinarily do to give 

 ketones, but instead condense to give acids, 

 (HO)-2GbH3CH2CH2C02H, etc. Alpha-beta- 



unsaturated nitriles give the same tj-pe of con- 

 densation product, indicating without doubt that 

 with these compounds the first step is the addition 

 of hydrogen chloride to the double bond. 



A new method of preparing unsaturated 1, 4- 

 diketones: J. B. Conant and B. E. LuTZ. Sujb- 

 stanees of the general type ECOCH=CHCOE are 

 of interest because they contain the characteristic 

 linkage of quinone and indigo. Only a relativedy 

 few representatives have been previously pre- 

 pared and the methods of preparation are diffi- 

 cult. We have prepared a number of aryl unfet- 

 urated 1, 4-diketones by the action of fumkryl 

 chloride, aluminum chloride, and an aromatic 

 hydrocarbon. The yields are good. It is inter- 

 esting that these substances are all smoothly re- 

 duced to the corresponding ethane derivatives by 

 sodiuin hydrosulfite or titanous chloride in con- 

 trast to ketones of the tj'pe ROH=OHCOE, or- 

 acids of the type H02CCH=CHC02H, which are 

 not reduced by these reagents. 



The preparation of hydroxy pyruvic acid: W. L. 

 Evans and G. P. Hopf. The following steps 

 were used: (1) pyruvic acid, (2) monobromo- 

 pyruvic acid, (3) its methyl ester, (4) methyl 

 ester of hydroxypyruvic acid, (5) hydroxypyruvic 

 acid. The conversion of (3) to (4) was accom- 

 plished by means of methyl -alcohol and potassium 

 formate, (5) is easily obtained from a slightly 

 acidulated aqueous solution of (4). 



Charles L. Parsons, 



Secretary 



