376 
Aralia  Nu  die  a  u  lis . 
( Am.  Jour.  Pharm. 
I      August,  1899. 
It  was  then  subjected  to  repeated  distillations  at  reduced  pressure 
of  80  millimetres.  By  far  the  larger  portion  distils  at  this  pressure 
at  a  temperature  of  185 0  to  195 0  ;  at  normal  pressure  the  boiling  point 
is  from  2600  to  2700. 
After  a  series  of  tests  for  nitrogen,  sulphur  and  halogens,  show- 
ing the  absence  of  these  elements,  a  number  of  combustions  were 
made  with  the  following  result : 
c. 
H. 
0. 
(By  subtraction.) 
Per  Cent. 
Per  Cent. 
Per  Cent. 
.  86-24 
II-52 
2*24 
86-28 
11-47 
2  25 
•  85-95 
II-58 
2-47 
While  the  proportion  of  carbon 
and  hydro^ 
yen  seemed  to  indicate  the 
presence  of  a  terpene,  (C10H16)n,  it  was  clear  from  the  calculated 
oxygen  that  at  the  same  time  a  compound  containing  this  element, 
probably  an  alcohol,  was  mixed  with  it.  All  efforts  to  separate 
these  two  or  more  substances  by  fractional  distillation  were  futile, 
the  boiling  point  gradually  rising  from  2600  to  2700,  when  the  last 
particle  would  pass  over,  without  showing  any  indication  of  accumu- 
lation at  any  particular  point.  It  became,  therefore,  necessary  to 
adopt  chemical  methods  for  their  separation ;  this  could  be  done 
only  with  the  greatest  care  owing  to  the  small  quantity  disposable. 
After  several  unsuccessful  efforts,  metallic  sodium  was  added  to  the 
oil,  causing  a  lively  reaction  with  generation  of  hydrogen,  the 
sodium  combining  with  the  substance  or  a  part  of  it.  The  whole 
mass  became  thick  and  gelatinous,  and  it  was  then  supposed  that 
polymerization  had  taken  place.  At  this  point  the  investigation 
was  interrupted  for  a  number  of  months.  After  this  time  it  was 
observed  that  the  gelatinous  mass  consisted  of  two  parts  of  different 
aggregation,  and  for  their  separation  distillation  at  a  pressure  of  80 
millimetres  was  undertaken.  At  this  pressure  a  perfectly  colorless 
oil  of  a  strongly  aromatic  odor  distilled  over  at  a  temperature  of 
1890,  comprising  more  than  two-thirds  of  the  previous  quantity. 
The  remaining  fraction  showed  the  presence  of  sodium. 
On  raising  the  temperature  still  higher  at  ordinary  pressure,  a 
few  drops  of  a  clear  blue  oil  were  obtained,  at  a  temperature  of 
about  3000,  probably  azulene  of  the  formula  C16H260  (boiling  point, 
302°). 
The  clear  oil  was  redistilled  at  ordinary  pressure,  and  a  steady 
boiling  point  of  2700  observed.    Elementary  analyses  resulted  as 
follows : 
