Am.  Jour.  Pharm. 
June,  19 18. 
Dichloramin-T  Solvents. 
425 
rigidly  carried  out  the  spent  solution  really  became  a  veritable  incu- 
bator for  bacteria. 
A  little  later  Dakin  introduced1  chlorazene,  or  sodium  para- 
toluenesulphochloramine  (C6H4CH3S02NaNCl  +  3H0O),  a  com- 
pound first  made  by  Chattaway. 2  This  compound  is  soluble  in  water 
and  was  extensively  used  until  Dichloramin-T  was  introduced  by 
Dakin  in  Europe  and  by  Lee,  Sweet  and  Lewis  in  the  United  States. 
Dichloramin-T,  or  paratoluenesulphodichloramide  (C6H4CH3- 
S02NC12),  is  a  white  to  pale  yellow  powder  or  granule  having  a 
rather  pleasant  hypochlorous  odor,  soluble  in  chloroform,  benzene, 
eucalyptol  and  paraffine  oil,  and  insoluble  in  water.  It  is  incom- 
patible with  alkalies  and  strong  acids.  It  rapidly  decomposes  in  the 
presence  of  the  slightest  moisture  and  of  excessive  heat  and  light. 
It  is  prepared  from  toluene  passing  through  the  successive  com- 
pounds, paratoluenesulphonic  acid,  sodium  paratoluenesulphonate, 
paratoluenesulphonchloride,  paratoluenesulphonamide,  and  parato- 
luenesulphodichloramide. 
When  first  introduced  in  this  country3  it  was  recommended  to  be 
used  in  solutions  of  chlorinated  eucalyptol  ranging  from  2  to  20 
per  cent.,  subsequently  diluted  with  chlorinated  paraffin  oil.  The 
solutions  were  extremely  unstable  and  especially  so  after  the  addi- 
tion of  the  chlorinated  paraffin  oil.  Chlorinated  eucalyptol  (Dakin) 
differed  physically  but  very  little  from  eucalyptol  U.  S.  P.,  but  con- 
tained varying  amounts  of  combined  chlorine  ranging  from  3  to  5 
per  cent.  Using  this  alone  as  a  solvent  was  unsatisfactory  because 
of  the  lack  of  density,  viscosity  and  its  volatility.  The  addition  of 
chlorinated  paraffin  oil  remedied  these  faults,  but  as  it  destroyed  the 
stability  of  the  solution  could  not  be  considered  the  ideal  means  of 
using  dichloramin-T. 
The  desire  to  arrive  at  a  satisfactory  solvent  measuring  up  to 
all  the  requirements  led  to  some  original  work  by  the  Phipps  Insti- 
tute of  the  University  of  Pennsylvania  and  chlorinated  eucalyptol 
1.2  was  introduced.  This  was  prepared  from  eucalyptol  U.  S.  P.  by 
forcing  chlorine  into  it  at  a  temperature  below  8o°  C.  until  the  spe- 
cific gravity  of  the  mixture  was  1.19  and  on  subsequent  washing 
free  from  acid  and  drying  with  calcium  chloride  the  finished  product 
was  a  pale  yellow  oily  liquid,  specific  gravity  1.2,  with  an  odor  a 
1  British  Medical  Journal,  August  25,  1915,  and  January  29,  1916. 
2  Trans.  Chem.  Soc,  1905,  lxxxvii,  153. 
3  Jr.  A.  M.  A.,  July  7,  1917. 
