38 
Chlor  acetones. 
Am.  Jour.  Pharm, 
Jan.,  1888. 
The  fraction  boiling  at  290°  contains  a  considerable  quantity  of  hexa- 
clilorobenzene,  which  is  probably  formed  by  pyrogenic  decomposition, 
and  does  not  exist  in  the  product  before  distillation.  It  is  not  always 
formed. 
Hexachloracetone  is  a  very  limpid  liquid  with  an  odor  which  is 
feeble  at  a  low  temperature,  but  becomes  very  pungent  and  irritating 
when  the  liquid  is  warmed.  It  boils  without  decomposition  at  202 — 
204°,  and  when  cooled  solidifies  in  large,  white  plates  melting  at 
— 2°;  sp.  gr.  at  12°=l-744;  vapor  density  9-615.  It  is  slightly 
soluble  in  water,  and  forms  a  crystalline  monohydrate  which  is  almost 
insoluble  in  water.  With  aqueous  ammonia,  it  yields  chloroform  and 
trichloracetamicle,  and  with  aniline  it  yields  chloroform  and  trichlor- 
acetanilide.  When  heated  with  water  in  sealed  tubes  at  120°,  it  splits 
up  into  chloroform  and  trichloracetic  acid.  The  action  of  chlorine  on 
epichlorhydrin  in  sunlight  yields  crystals  which  seem  to  be  hexachloro- 
benzene,  and  a  small  quantity  of  a  liquid  which  boils  at  200 — 210° 
and  yields  chloroform  and  trichloracetamide  with  ammonia.  Most 
CC] 
probably  the  product  has  the  constitution  CC13'CC1<_q_^>. 
Chlor obromacetones. — Theegarten  treated  epichlorhydrin  with  bro- 
mine, and  oxidized  the  product.  In  this  way,  he  obtained  crystals 
which  have  an  irritating  odor,  melt  at  34 — 35°,  and  boil  at  177 — 180°. 
This  compound  is  only  slightly  soluble  in  water,  but  dissolves  readily 
in  alcohol  and  ether.  It  does  not  combine  with  bisulphites,  and  doubt- 
less has  the  constitution 
CHoCl-CH<^^^> 
A  compound  with  the  composition  of  monochlorotribromacetone 
was  obtained  by  Claus  and  Lindhorst  (1880)  by  the  action  of 
bromine  and  water  on  dichlorhydrin,  and  by  Grimaux  and  Adam 
by  the  action  of  bromine  on  epichlorhydrin  at  100°.  With  equal 
molecular  proportions  of  bromine  and  epichlorhydrin,  the  reaction  is 
complete  in  a  few  hours.  The  product  is  a  colorless,  pungent  liquid, 
heavier  than  water,  with  which  it  forms  a  hydrate  melting  at  55°, 
soluble  in  alcohol,  and  stable  when  exposed  to  air.  The  compound 
itself  decomposes  when  boiled  even  under  reduced  pressure.  It  is 
not  a  true  derivative  of  acetone,  but  is  derived  from  epichlorhy- 
drin. 
When  monochloracetone  is  heated  with  bromine  at  100°  and  the 
