Am.  Jour.  Pharm. 
Jan..  1888. 
CM  or  acetones. 
33 
odor^  forms  crystals  which  melt  at  44°^  and  boils  at  170°  without 
decomposition. 
When  dichlorhydrin  is  oxidized  by  means  of  a  well-cooled  mixture 
of  sulphiaric  acid  and  potassium  dichromate,  in  the  manner  described 
by  Grimaux  and  Adam,  it  yields  a  liquid  which  has  the  composition 
of  dichloracetone.  When  this  product  is  cooled,  it  crystallizes  in 
large  needles  melting  at  43 — 44°,  which  change  spontaneously,  es- 
pecially in  presence  of  ether,  into  short  prisms  with  the  same  melting 
point.  It  boils  at  170°,  has  a  very  pungent  odor,  and  in  ethereal 
or  alcoholic  solution  is  a  most  powerful  caustic,  producing  very  severe 
burns.  With  ammonia,  it  forms  an  unstable  compound  which  crys- 
tallizes in  large  plates. 
In  diffused  daylight,  chlorine  acts  somewhat  slowly  on  epichlor- 
hydrin.  When  the  product  is  distilled  and  the  fraction  boiling  at 
160 — 180°  is  purified,  it  yields  a  liquid  which  boils  at  170°  and  has 
CH 
the  composition  CHClg'Cll  '<_qJ>  ,  and  is  therefore  an  isomeride 
of  dichloracetone.  With  ammonia  at  a  low  temperature,  it  yields  a 
w^hite,  amorphous,  unstable  substance,  almost  insoluble  in  water, 
alcohol,  and  ether ;  this  has  the  formula  C6H4CI2NO2,  but  its  constitu- 
tion could  not  be  determined. 
The  dichloracetone  obtained  from  diiodoacetone  is  not  identical  with 
the  so-called  symmetrical  dichloracetone  obtained  by  the  oxidation  of 
dichlorhydrin.  The  action  of  bromine,  potash,  or  oxidising  agents  on 
dichlorhydrin  yields  derivatives  which  closely  resemble  derivatives  of 
the  acetone?,  but  are  never  identical  with  them.  Potash  yields  ,epi- 
chlorhydrin,  which  closely  resembles  monochloracetone  in  its  physical 
properties.  Bromine  yields  a  derivative  to  which  the  constitution 
CO(CHClBr)2  has  been  assigned.  A  compound,  CHCl^CO'CHBr^, 
can  also  be  obtained  from  acetone.  If  the  two  compounds  are  treated 
with  mercuric  chloride  the  latter  yields  tetrachloracetone,  whilst 
the  former  yields  a  compound  containing  a  lower  percentage  of 
chlorine. 
If  ordinary  dichloracetone  and  the  symmetrical  dichloracetone  from 
the  iodo-derivative  are  treated  with  bromine,  they  both  yield  dichloro- 
dibromacetones,  and  when  the  latter  are  treated  with  mercuric  chloride 
the  same  symmetrical  tetrachloracetone  is  obtained  in  both  cases. 
When  the  pseudodichloracetone  from  dichlorhydrin  is  treated  in  the 
same  way,  the  product  is  an  isomeride  of  tetrachloracetone,  very  dis- 
