Identification of Benzo[b]thiophene and its 2- and 3-Methyl Homologs in Wasson, Texas, Crude Oil

Spectrophotometric determination of primary aromatic amines with 9-chloroacridine

“…Investigation supported in part by the Office of General Research, University of Georgia. There is ample evidence that thiols (1-3), sulfides (1, 4-8), thiophenes (I, 9-12), benzothiophenes (13,14), and thiaindans (15) are present in crude oils. However, prior to this investigation no alkyl aryl sulfide had been identified in any crude oil.…”

Biotransformation of benzothiophene by isopropylbenzene-degrading bacteria

“…The sequence of events that occurs following attack at the 2,3 position of the thiophene ring is less clear, but it is proposed that 2,3 dioxygenation yields a product that is both a cis-dihydrodiol and a thiohemiacetal, which as a result of this structure undergoes two competing reactions: either spontaneous opening of the ring, yielding 2'-mercaptomandelaldehyde, or oxidation by the dihydrodiol dehydrogenase to another thiohemiacetal, 2-hydroxy-3-oxo-2,3-dihydrobenzothiophene, which is not a substrate for the ring cleavage dioxygenase but which spontaneously opens to form 2-mercaptophenylglyoxaldehyde and subsequently 2-mercaptophenylglyoxalate. The yellow product, trans4[3-hydroxy-2-thienylJ-2-oxobut-3-enoate, is a structural analog of nins-o-hydroxybenzylidenepyruvate, an intermediate of the naphthalene catabolic pathway; extracts of recombinant bacteria containing zns-o-hydroxybenzylidenepyruvate hydratase-aldolase catalyzed the conversion of ans-4-[3-hydroxy-2-thienyl]-2-oxobut-3-enoate to 3-hydroxythiophene-2-carboxaldehyde, which could then be further acted on, in the presence of NAD+, by extracts of recombinant bacteria containing the subsequent enzyme of the naphthalene pathway, salicylaldehyde dehydrogenase.Sulfur-containing heterocyclic chemicals, including benzothiophene (benzo-[b]-thiophene, thianaphthene), comprise a relatively small but significant fraction of petroleum, coal, and shale (5,9,26,30,42). …”

“…Sulfur-containing heterocyclic chemicals, including benzothiophene (benzo-[b]-thiophene, thianaphthene), comprise a relatively small but significant fraction of petroleum, coal, and shale (5,9,26,30,42).…”