Abstract-The acute toxicity of wastewater generated during the extraction of bitumen from oil sands is believed to be due to naphthenic acids (NAs). To determine the factors that affect the rate of degradation of representative NAs in microcosms containing wastewater and the acute toxicity of treated and untreated wastewater, the effects of temperature, dissolved oxygen concentration, and phosphate addition on the rate of 14 CO 2 release from two representative naphthenic acid substrates, (linear) U-14 C-palmitic acid (PA) and (bicyclic) decahydro-2-naphthoic acid-8-14 C (DHNA), were monitored. Tailings pond water (TPW) contained microorganisms well adapted to mineralizing both PA and DHNA: PA was degraded more quickly (10-15% in 4 weeks) compared to DHNA (2-4% in 8 weeks). On addition of phosphate, the rate of NA degradation increased up to twofold in the first 4 weeks, with a concurrent increase in the rate of oxygen consumption by oil sands TPW. The degradation rate then declined to levels equivalent to those measured in flasks without phosphate. The observed plateau was not due to phosphate limitation. Decreases in either the dissolved oxygen concentration or the temperature reduced the rate. Phosphate addition also significantly decreased the acute toxicity of TPW to fathead minnows. In contrast, Microtox analyses showed no reduction in the toxicity of treated or untreated TPW after incubation for up to 8 weeks at 15ЊC.

The purpose of this study was to determine the ability of nonbasidiomycete soil fungi to oxidize pyrene (four rings) and benzo[a]pyrene (BaP) (five rings). Fungi were isolated from five different soils in which the polycyclic aromatic hydrocarbon content ranged from 0.8 to 80 micrograms/g dry soil. Approximately 50% of the isolates in all sites were able to oxidize pyrene. The pyrene-oxidizing species belonged to all fungal divisions except basidiomycetes. The most common were Penicillium spp. of the subgenus Furcatum and these dominated the more contaminated soils. Penicillium janthinellum and Syncephalastrum racemosum exhibited the most rapid rates of pyrene oxidation. The major pyrene metabolites were identified by proton NMR and mass spectrometry as 1-pyrenol, 1,6- and 1,8-pyrenediol, and the 1,6-and 1,8-pyrenequinones. A high correlation was found between the ability to oxidize pyrene and BaP. As with pyrene, approximately 50% of the fungal isolates tested oxidized BaP to 9-hydroxy-BaP. Eighty percent of the pyrene-oxidizing strains were also able to metabolize BaP.

+)-/ra».i-Dihydroquercetin (taxifolin, 1) equilibrates with approximately 10% of its less stable (+)-«j diastereomer (epitaxifolin, 2) in hot aqueous or alcoholic solution by C-2 epimerization. The reaction is postulated to proceed through an optically active quinone methide formed by heterocyclic ring opening. Racemization and isomerization to alphitonin (2benzy 1-2,3' ,4,4' ,6-pentahydroxy-3 -coumaranone, 3) at elevated temperatures or with acid/base catalysts are attributable to slow deprotonation at C-3 and formation of an achiral ct-diketone intermediate. Dibasic sodium phosphate converts dihydroquercetin to the dihydrate of a hemisodium salt.

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The compounds 1,1′-carbonylbis(3-methylpyrazole) (1), 1,1′-carbonylbis(3,5-dimethylpyrazole) (2), and 1,1′-sulfinyldipyrazole (3) have been prepared. They react with aldehydes and ketones in the presence of metal ion catalysts to form 1,1′-alkylidenedipyrazoles together with carbon dioxide, from 1 and 2, or sulfur dioxide, from 3. Tetrapyrazol-1-ylmethane results from the pyrolysis at 200° of 1,1′-carbonyldipyrazole in the presence of cobalt(II) chloride.