Geosynthesis of organic compounds: I. Alkylphenols

Abstract

Methylation, isopropylation, and sec-butylation are proposed as geosynthetic 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 spectrometry). Ten of the crude oils show high relative abundances of ortho and para substituted phenol isomers and some were also enriched in C3–C5 alkylphenols compared to the kerogen pyrolysates. Because the distributions of products obtained from the laboratory alkylation of cresols closely resemble those of phenols in these crude oils, we propose that similar alkylation processes occur in source rocks. Alkylation ratios reflecting the degree of methylation, isopropylation, and sec-butylation, which were based on the relative abundance of the dominant alkylation products compared to their likely precursor ortho-cresol, indicate that high levels of methylation occurred in crude oils over a wide range of maturities, whereas high levels of isopropylation and sec-butylation were observed only in mature samples. Dissolution of the phenols in crude oils by water contact was discounted as an explanation for the observed phenol distributions based on the relative distribution coefficients of phenols between a hydrocarbon phase and water.