334  An  Old  Sample  of  Camphor  Oil  {Amju^m9arm- 
The  lighter  fractions  of  this  oil  are  identical  in  boiling  points  with 
those  obtained  from  No.  1  oil  of  our  last  paper3  with  exception  of  frac- 
tion (1)  which  was  entirely  absent ;  these  lighter  fractions  however, 
exist  only  in  one-half  the  quantity. 
The  large  percentage  of  camphor  is  due  no  doubt  to  the  ageing  of 
the  oil,  having  probably  been  originally  present  as  the  compound  (8), 
camphorogenol.  This  compound  (8)  exists  now  in  the  oil  to  only  one- 
half  the  amount  it  was  present  in  No.  I  oil.  Fraction  (9),  safrol,  and 
(10),  eugenol,  could  not  be  detected  in  this  sample  by  any  of  the 
methods  used  for  obtaining  these  compounds  from  No.  I  oil.  A  por- 
tion of  the  oil  when  shaken  with  concentrated  aqueous  solution  of  po- 
tassium hydrate,  showed  no  separation  of  eugenate  of  potassium,  and 
on  addition  of  a  mineral  acid  to  this  mixture,  no  odor  of  eugenol  was 
developed.  The  odor  of  safrol  was  not  detected  in  any  of  the  meth- 
ods used  for  treatment  of  the  higher  boiling  fractions. 
Fraction  (11)  possessed  not  the  greenish  blue  color  as  from  No.  I 
oil,  but  had  a  very  deep  yellow  color.  It,  however,  gave  Wallach's 
reaction  for  a  sesquiterpene,  with  glacial  acetic  and  concentrated  sul- 
phuric acids.  The  greenish  blue  oil  detected  in  samples  I  and  II  was 
entirely  absent  from  this  sample.  This  fraction  gave  with  an  alcoholic 
solution  of  ferric  chloride  a  brownish  green  coloration.  This  however 
was  not  due  to  eugenol,  since  we  had  evidence  of  its  absence.  (11.) 
from  No.  I  oil  also  gave  this  greenish  coloration.  Alcoholic  ferric 
chloride  added  to  fraction  R,  eugenol,  from  No.  I  oil,  gave  a  blueish 
green  coloration,  which  was  decidedly  different  from  that  produced 
with  fractions  (11). 
Fractions  (2)  to  (6),  inclusive,  are  no  doubt  identical  with  those 
obtained  from  No.  I  oil  with  the  same  boiling  points,  since  their  action 
on  polarized  light  proved  to  be  about  the  same. 
The  polariscope  readings  for  (2),  (3)  and  (5)  with  the  200  mm.  tube 
were  as  follows,  compared  with  No.  I  oil  : 
No.  IX  Oil.  No.  I  Oil. 
(2)  .  From  158°-161°  C                           -f54'20  +54-°. 
(3)  .     "      167°-169°C                          +57-2°  +56-9°. 
(5).     «      175°-177°  C                          +62-2°  +62-4°. 
The  absence  of  safrol  and  eugenol  was  also  indicated  by  the  strong 
dextro-rotary  power  this  sample  exerted  on  polarized  light,  being  sim- 
ilar to  samples  III,  IV  and  V,  all  of  which  consisted  of  a  solution 
of  camphor  in  the  light  fractions  of  camphor  oil.    This  sample  of  oil 
