THE  AMERICAN 
JOURNAL  OF  PHARMACY. 
FEBRUARY,  1887. 
TEREBENE. 
By  H.  W.  Jayne,  Ph.  D.  and  G.  H.  Chase. 
Read  at  the  Pharmaceutical  Meeting,  January  18. 
Terebene  first  appeared  in  chemical  literature  in  1840,  when  Sou- 
beiran  and  Capitaine  (Ann.  34,311),  gave  this  name  to  a  substance 
obtained  by  acting  on  oil  of  turpentine  with  gaseous  hydrochloric  acid. 
After  removing  the  solid  hydrochloride  of  turpentine,  the  liquid  por- 
tion was  distilled  over  lime.  This  distillate  was  their  so-called  tere- 
bene. It  was  a  liquid  boiling  at  135°  C.  and  differing  from  the  origi- 
nal oil  of  turpentine  by  being  inactive  to  polarized  light. 
Deville,  in  1841  (Ann.  37,178),  described  the  preparation  of  this 
body  by  the  action  of  concentrated  sulphuric  acid  on  oil  of  turpentine. 
His  terebene  was  a  liquid  having  a  pleasant  odor  like  thyme  and  the 
same  gravity  and  boiling  point  as  oil  of  turpentine. 
In  1873,  Riban  {Bulletin  Soc.  Chim.  xx.  100),  published  the  re- 
sults of  an  extensive  investigation  on  this  subject.  According  to  him 
the  substance  obtained  by  the  action  of  acid  on  oil  of  turpentine  and 
heretofore  called  terebene,  was  a  mixture  of  true  terebene  boiling  at 
155°-156°  C.  and  cymol  174-176°  C.  He  also  notes  the  presence  of 
a  camphor  among  the  products  of  the  reaction.  This  pure  terebene 
had  a  faint  odor  and  did  not  solidify  at — 27°  C.  When  treated  with 
more  acid  the  mixture  became  hot  and  a  certain  amount  of  terebene  was 
converted  into  cymol,  together  with  the  formation  of  colophene  or 
diterebene.  By  continued  treatment  the  terebene  was  entirely  con- 
verted into  cymol  and  colophene.  This  reaction  takes  place  with  the 
evolution  of  much  sulphurous  anhydride. 
In  1879  an  addition  to  the  already  copious  literature  on  this  sub- 
ject was  made  by  Armstrong  and  Tilden  (Berichte  xii,  1752),  who 
thought  that  terebene  was  not  a  chemical  compound  but  a  mixture  of 
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