Pyrolysis mechanisms of lignin model compounds Page: 4 of 6
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degradation of the -0-4 linkage, the dominant interunit linkage in lignin, by studying the FVP
of phenethyl phenyl ether (PPE) and phenethyl o-methoxyphenyl ether (o-CH30-PPE).
The synthesis of phenethyl phenyl ether, phenethyl-1,1-d2 phenyl ether, and phenethyl o-
methoxyphenyl ether has been previously described . The flash vacuum pyrolysis
apparatus was based on the design reported by Trahanovsky  and has been previously
reported . All experiments were run at 500 *C and pressures <10-3 Torr. Products were
analyzed by GC and GC-MS and identified by comparison of GC retention times and mass
spectral fragmentation patterns with authentic samples.
3. RESULTS AND DISCUSSION
The products from the FVP of PPE at 500 *C are shown below (average mol % from three
runs). The major products, styrene and phenol, can be produced by two competing
H H ~0.94 %
55.9 2.8 %
Q-CH2 -CH2 Q
+,N CH2 +
40.5 2.5 %
0.25 0.05 %
0.38 0.07 %
1.4 0.3 %
pathways: a) homolytic cleavage of the weakest bond in the molecule (D c-o estimated as 63
kcal mol"1) to give PhO- and PhCH2CH2- which can form phenol and styrene by addition and
(-scission of a hydrogen atom, respectively, or b) 1,2-elimination to produce the phenol and
styrene directly . Unfortunately, it is very difficult to deconvolute these two pathways in
-the decomposition of PPE since both routes lead to the same products. However, the rate of
1,2-elimination should be slower for PhCD2CH2OPh than for PPE as a consequence of
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Britt, P.F.; Buchanan, A.C. III & Cooney, M.J. Pyrolysis mechanisms of lignin model compounds, article, June 1, 1997; Tennessee. (digital.library.unt.edu/ark:/67531/metadc696366/m1/4/: accessed November 22, 2017), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT Libraries Government Documents Department.