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Model studies and the ADMET polymerization of soybean oil
Author(s) -
Tian Qingping,
Larock Richard C.
Publication year - 2002
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-002-0509-3
Subject(s) - trimer , pentamer , polymerization , tetramer , chemistry , random hexamer , dimer , polymer chemistry , oligomer , metathesis , acyclic diene metathesis , ethylene glycol , polymer , organic chemistry , crystallography , biochemistry , enzyme
Grubbs' ruthenium catalyst 2 has been employed in model studies of the acyclic diene metathesis (ADMET) polymerization of soybean oil. In the presence of 0.1 mol% of catalyst 2 , the ADMET polymerization of ethylene glycol dioleate afforded the isomerized ( E )‐dioleate (27%), dimer (18%), trimer (13%), tetramer (7%), pentamer (5%), hexamer (4%), heptamer (4%), and 9‐octadecene (21%). Only a trace of any intramolecular cyclized product was formed. Under the same conditions, glycerol trioleate underwent ADMET polymerization to produce dimer, trimer, tetramer, pentamer, and monocyclic oligomers, with monocyclic oligomers predominating. The high number of repeat units in the monocyclic oligomers ( n ≅6, 10, and 21) in dicates that cross‐linking occurs readily in this process. Based on our model system studies, we have examined the ADMET polymerization of soybean oil and succeeded in producing polymeric materials ranging from sticky oils to rubbers.