274 
Chlorinated  Oil. 
f  Am.  Jonr.  Pliarm. 
\      June,  1882. 
The  oil  so  treated  showed  at  first  but  little  change,  save  that  of  tur- 
bidity, which  could  not  have  been  due  to  water  being  present,  as  the 
gas  had  been  well  dried.  It  soon  warmed  and  heated,  and  vapors  of 
hydrochloric  acid  were  then  evolved.  It  had  changed  its  color  but 
little,  grew  viscid  and  of  the  specific  gravity  of  1'059.  It  is  insoluble 
in  alcohol,  disproving  the  presence  of  free  oleic  acid ;  when  washed 
with  an  equal  bulk  of  water,  to  free  from  adherent  hydrochloric  acid, 
it  showed  au  emulsifiant  tendency.  Dissolved  therefrom  with  benzin, 
and  the  latter  evaporated  after  previously  filtering  the  solution,  it  left 
a  product  such  as  I  here  exhibit.  Neutral  to  test  paper  at  first,  it 
grew  acid  at  standing  for  some  time,  with  well  marked  turbidity,  thus 
proving  the  loosely  molecular  combination  of  the  chlorine,  which, 
being  again  substituted  by  hydroxyl,  forms  more  hydrochloric  acid. 
It  possesses  no  marked  odor,  and  certainly  not  that  of  chlorine,  and 
varied  in  taste  but  little  from  that  of  ordinary  oils,  no  irritant  action 
being  manifest  when  applied  to  the  tissues. 
An  inquiry  on  this  subject  at  our  former  meetings  led  me  to  inves- 
tigate this  matter  more  thoroughly,  and  I  arrived  at  results  which, 
from  a  chemical  point  of  view,  turned  out  very  interesting. 
In  order  to  understand,  the  chemistry  of  this  process  it  is  necessary', 
however,  to  enter  somewhat  into  the  molecular  position  of  the  vege- 
table and 'animal  oils  and  fats  to  show  exactly  where  and  how  a  chlo- 
rine substitution  can  take  place. 
Vegetable  and  animal  oils  consist  in  the  main  of  two  principles  : 
one  of  them,  forming  on  saponification,  either  w^ith  or  without  great 
heat  or  alkalies,  is  an  alcohol  named  glycerin ;  the  other,  forming 
acids,  are  termed  relatively  stearic,  j^jalmitic  and  oleic  acids,  etc.  The 
radicals  of  these  two  constituents  are  for  the  former  termed  propenyl 
or  glyceryl,  while  for  the  latter  they  are  known  as  stearyl,  palmityl, 
and  for  that  which  forms  the  greatest  part  of  the  liquid  and  semi- 
liquid  fats,  oleyl. 
While  the  propenyl  would  be  expressed  as  follows : 
H 
I 
— C— H 
I 
C3H5  =  — C — H 
— C— H 
I 
H 
the  glycerin  or  its  triatomic  alcohol  would  be  constituted  thus : 
