Methylation, isopropylation, and sec-butylation are proposed as geosyn
thetic processes to account for the alkylphenol compositions of crude
oils with phenol distributions dominated by ortho and para substituted
compounds. Phenol distributions in eleven crude oils and four kerogen
pyrolysates were analysed using GC-MS (gas chromatography-mass spectr
ometry). Ten of the crude oils show high relative abundances of ortho
and para substituted phenol isomers and some were also enriched in C-3
-C-5 alkylphenols compared to the kerogen pyrolysates. Because the dis
tributions of products obtained from the laboratory alkylation of cres
ols closely resemble those of phenols in these crude oils, we propose
that similar alkylation processes occur in source rocks. Alkylation ra
tios reflecting the degree of methylation, isopropylation, and sec-but
ylation, which were based on the relative abundance of the dominant al
kylation products compared to their likely precursor ortho-cresol, ind
icate that high levels of methylation occurred in crude oils over a wi
de range of maturities, whereas high levels of isopropylation and sec-
butylation were observed only in mature samples. Dissolution of the ph
enols in crude oils by water contact was discounted as an explanation
for the observed phenol distributions based on the relative distributi
on coefficients of phenols between a hydrocarbon phase and water.