464  Separation  of  Morphine  from  Glycerin.    { A™VTwb£,  w£m 
SEPARATION  OF  MORPHINE  FROM  ITS  SOLUTION  IN 
GLYCERIN.1 
By  H.  M.  Gordin. 
In  collaboration  with  W.  H.  Harrison. 
Owing  to  the  considerable  solubility  of  morphine  in  glycerin  it  is 
difficult  to  separate  this  alkaloid  from  its  solvent.  From  a  50  per 
cent,  solution  of  glycerin  containing  about  250  milligrammes  of  the 
alkaloid  in  100  c.c.  of  liquid,  morphine  is  not  precipitated  by  alka- 
line carbonates.  Ether  or  chloroform  do  not  dissolve  glycerin,  but 
neither  do  they  dissolve  much  morphine.  Amyl  alcohol  is  a  some- 
what better  solvent  for  morphine,  but  it  also  dissolves  about  8  per 
cent,  glycerin.  Hence  on  shaking  out  a  glycerin  solution  of  morphine 
with  amyl  alcohol  three  or  four  times  considerable  glycerin  will  go 
along  with  the  alkaloid,  and  when  the  amyl  alcohol  is  then  shaken 
out  with  acidulated  water  the  water  will  take  up  both  the  alkaloid 
and  glycerin. 
The  first  method  that  suggested  itself  was  to  remove  the  glycerin 
by  a  current  of  steam.  It  was  found  that  ordinary  steam  at  ioo° 
does  not  take  up  any  appreciable  amount  of  glycerin.  Even  super- 
heated steam  at  1 35 0  takes  up  very  little  glycerin. 
Steam  of  a  much  higher  temperature  would  undoubtedly  remove 
all  the  glycerin,  but  it  being  certain  that  high  temperatures  would 
destroy  the  morphine  during  the  long  time  that  is  required  to  remove 
all  the  glycerin  the  method  was  dropped. 
The  second  method  was  to  mix  the  glycerin  solution  of  morphine 
with  about  ten  times  its  amount  of  lead  oxide,  heat  on  the  water- 
bath  to  perfect  dryness  and  extract  the  morphine  repeatedly  with 
hot  amyl  alcohol.  From  the  latter  the  alkaloid  could  then  be  ex- 
tracted by  means  of  dilute  acid.  While  this  method  looked  prom- 
ising at  first  the  results  were  entirely  negative.  Not  a  trace  of 
morphine  was  recovered.  Either  the  alkaloid  is  destroyed  by  the 
heating  on  the  water-bath  with  the  lead  oxide  or,  what  is  more 
probable,  morphine  having  a  phenolic  character  forms  a  lead  salt 
with  the  metallic  oxide,  which  salt  is  completely  insoluble  in  hot 
amyl  alcohol. 
1  Read  at  the  meeting  of  the  American  Pharmaceutical  Association,  Sep- 
tember, 1906,  and  contributed  by  the  author. 
