Am.  Jooti.  Pharbi.  ) 
Nov.  1,  1872.  J 
Note  on  Guaiacol. 
507 
good ;  almost  identical  with  guaiacol,  but  it  was  soluble  in  glycerin. 
Attempts  made  to  detect  the  presence  of  carbolic  acid  quite  failed. 
Other  means  were  then  tried  to  procure  evidence  of  the  presence  of 
carbolic  acid  in  creasote. 
It  is  stated  in  the  paper  first  referred  to  (Ph.  Jour.  No.  92,  p.  789), 
that  while  the  phenol  series  yields  with  nitric  acid  trinitrophenol  or 
picric  acid,  guaiacol  or  creasote  yields  only  oxalic  acid.  If  this  were 
true,  we  might  hope  to  detect  the  presence  of  picric  acid,  and  thus 
prove  that  carbolic  acid  had  beSn  contained  in  the  creasote. 
To  determine  this  point,  the  creasote  to  be  examined  was  first  dis- 
solved in  about  twice  its  weight  of  glacial  acetic  acid,  and  then  added 
to  an  equal  bulk  of  strong  nitric  acid,  sp.  gr.  1500.  (If  the  creasote 
to  be  examined  is  added  direct  to  the  nitric  acid,  the  action  is  so  vio- 
lent and  unmanageable  that  no  definite  result  can  be  arrived  at.)  The 
capsule  containing  the  mixture  must  be  placed  on  a  sand-bath,  and 
evaporated  almost  to  dryness.  When  pure  carbolic  acid  has  been 
used,  the  product  is  a  bright  yellow  crystalline  mass  (pure  picric  acid), 
but  in  the  case  of  guaiacol  or  creasote  (both  English  and  German), 
the  product  is  a  brown,  sticky,  semi-resinous  mass.  This  product, 
treated  with  a  little  hot  water,  is  transferred  to  a  large  test  tube  or 
small  retort,  and  a  gramme  or  so  of  ordinary  bleaching  powder  added, 
and  a  gentle  heat  applied,  the  result  being  the  production  of  chloro- 
picrin if  picric  acid  is  present,  which  can  be  distinguished  without 
doubt  or  difficulty  by  its  most  peculiar  and  repulsive  smell,  or  can  be 
separated  by  distillation  if  thought  necessary  ;  but  if  oxalic  acid  is  the 
product  of  the  reaction,  no  chloropicrin  is  produced,  but  simply  a  lib- 
eration of  chlorine.  I  am  sorry  to  say  that  in  all  my  trials  I  obtained 
chloropicrin,  and  not  a  trace  of  chlorine,  and  all  other  attempts  made 
to  isolate  oxalic  acid  from  the  product  of  the  reaction  of  nitric  acid 
upon  guaiacol  or  creasote  having  quite  failed  I  have  come  to  the  con- 
clusion that  the  statement  respecting  the  different  products  obtained 
from  creasote  and  carbolic  acid  by  oxidation  is  incorrect.  Picric  acid, 
or  some  isomer  of  that  body,  is  the  product  of  the  reaction  in  all  cases, 
irrespective  of  the  source  of  the  creasote  (or  carbolic  acid)  being  from 
coal-tar  or  from  wood. 
Attempts  were  made  to  distinguish  between  carbolic  acid  and  crea- 
sote by  the  production  of  sulpho-conjugated  acids.  But  the  acid  pro- 
duced by  creasote  appears  to  be  too  much  like  the  sulpho-carbolic  acid 
for  anything  like  a  distinguishing  test  to  be  founded  upon  that  re- 
action. 
