A NEW LOOK AT THE MECHANISMS OF OXIDATIVE SEDIMENT FORMATION IN FUELS

References

• Akaba , R. , Sakuragi , H. , Tokumaru , K. , 1984 . Autoxidation of Adamantylideneadmantane in a Protic Solvent. Facile Proton-Induced Electron Transfer from Olefin to Oxygen . Tet. Lett. , 25 : 665 – 68 .
   Google Scholar
• Bartlett , P.D. , Roof , A.A.M. , Subramanyum , R. , and W.J. , Winter , 1984 . Addition Reactions to eynanti-Sesquinorbornenes Involving Ionic Mechanisms, The Role of Tetracyanoethylene . J. Org. Chem. , 49 : 1875 – 80 .
   Web of Science ®Google Scholar
• Beaver , B.D. , Cooney , J.V. and J.M. Watkins , Jr. , 1985 . Autoxidation of Nitrogen Heterocycles. 2. Kintetic Measurements of the Autoxidation of 2,5-Dimethylpyrrole . Heterocycles , 23 : 2847 – 51 .
   Web of Science ®Google Scholar
• Beaver , B.D. , Cooney , J.V. , and J. M. Watkins , Jr. , 1986 . Autoxidation of Nitrogen Heterocycles. 3. Solvent Effects in the Autoxidation of 2,5-Dimethylpyrrole . J. Heterocyclic Chem. , 23 : 1095 – 7 .
   Google Scholar
• Beaver , B.D. , Hazlett , R.N. , Cooney , J.V. , and J.M. Watkins , Jr. , 1987a . The Significance of the Oxidation of 2,5-Dimethylpyrrole in Oxidative Fuel Stability . Preprints of the Fuel Division , ACS , 32 : 538 – 46 .
   Google Scholar
• Beaver , B.D. , 1987b unpublished data .
   Google Scholar
• Bruice , T.C. , 1984 . Oxygen-Flavin Chemistry , Isreal J. Chem. , 24 : 54 – 61 .
   Google Scholar
• Burton , G.W. , and K.U. Ingold , 1981 . Autoxidation of Biological Molecules. 1. The Antioxidant Activity of Vitamin E and Related Chain-Breaking Phenolic Antioxidants in Vitro . J. Am. Chem. Soc. , 98 : 6472 – 77 .
   Google Scholar
• Cooney , J.V. and R.N. Hazlett , 1984 . Autoxidation of Nitrogen Heterocycles.1. Ultraviolet Spectra of Alkylpyrroles. Evidence for a Molecular Association Complex Between Oxygen and 5,2-Dimethylpyrrole in Nonpolar Media . Heterocycles , 22 : 1513 – 1518 .
   Web of Science ®Google Scholar
• Cooney , J.V. , and M.A. Wechter , 1986a . Oxygen absorption by 2,5-Dimethylpyrrole Doped Shale Diesel Fuels . Fuel , 65 : 433 – 436 .
   Web of Science ®Google Scholar
• Cooney , J.V. , Beal , E.J. and B.D. Beaver , 1986b . Mechanisms of Synfuel Degradation.3. Interactive Effects in Nitrogen Compounds . Induced Storage Instability in Shale Derived Diesel Fuel . Fuel Science & Technology Int'l , 4 : 1 – 18 .
   Google Scholar
• Creary X , and M.E. Kehrsheikh-Mohammadi , 1986 . Captodative Rate Enhancements in the Methylenecyclapropane Rearrangement . J. Org. Chem. , 51 2664 – 2668 .
   Google Scholar
• Diaz , A.F. , Martinez , A. , and K.K. Kanazawa , 1981 . Electrochemistry of Some Substituted Pyrroles . J. Electroanal. Chem. , 130 : 181 – 7 . In aprotic solvents alkylpyrroles generally have oxidation potentials ( −0.8 V vs. SCE) that are very cloae in energy to the reduction potential of triplet oxygen ( −.8V vs. SCE). However, N-alkyl or pyrroles that contain withdrawing groups have oxidation potentials much more negative than −.80V vs. SCE. Therefore, the oxidation of these pyrroles would not be expected to occur by way of the electron-transfer initiated oxidation depicted in (Scheme VI) .
   Web of Science ®Google Scholar
• D'Souza , V.T. , Nanijundiah , R. , Baeza , J.H. , and H.H. Szmant , 1987 . Thio Olefin Cooxidation (TOCO) RX.9. A Self-Consistent Mechanism under Non-Radical Inducing Conditions . J. Org. Chem. , 52 : 1729 – 40 , and references cited therein .
   Web of Science ®Google Scholar
• Evans , D.F. , 1953 . Molecular Association of Oxygen and Aromatic Substances . J. Chem. Soc. 345 – 7 .
   Web of Science ®Google Scholar
• Foote , C.S. , 1979 . Singlet Oxygen . Wasaerman , H.H. , Murray , R.W. , Ed., Academic Press , New York .
   Google Scholar
• Frankenfeld , J.W. , Taylor , W.F. , and D.W. Brinkman , 1983a . Storage Stability of Synfuels from Oil Shale.1. General Features of Sediment Formation in Model Fuel Systems . Ind. Eng. Chem. Prod. Res. Dev. , 22 : 608 – 14 .
   Web of Science ®Google Scholar
• Frankenfeld , J.W. , Taylor , W.F. , and D.W. Brinkman , 1983b . Storage Stability of Synfuels from Oil Shale.2. Effects of Nitrogen Compounds Type and the Influence of other Nonhydrocarbons on Sediment Formation in Model Fuel Systems . Ind. Eng. Chem. Prod. Res. Deve. , 22 : 615 – 21 .
   Web of Science ®Google Scholar
• Frankenfeld , J.W. , Taylor , W.F. and D.W. Brinkman , 1983c . Storage Stability of Synfuels from Oil Shale.3. Studies with Actual Shale Derived Middle Distillates . Ind. Eng. Chem. Prod. Res. Dev. , 22 : 622 – 27 .
   Web of Science ®Google Scholar
• Howard , J.A. , 1973 . Homogeneous Liquid Phase Autoxidation . Vol. 2 Free Radicals , J.K. Kochi , ED.
   Google Scholar
• Ingold , K.U. , 1961 . Inhibition of the Autoxidation of Organic Substances in the Liquid Phase . Chem. Rev. , 61 : 563 – 89 .
   Web of Science ®Google Scholar
• Khan , A.U. , 1978 . Activated Oxygen Singlet Molecular Oxygen and Superoxide Anion . Photochem. and Photobio. , 28 : 615 – 27 .
   Web of Science ®Google Scholar
• Landen , G.L. , Park , Y.T. , and D.A. Lightner , 1983 . On the Role of Singlet Oxygen in the Self-Sensitized Photo-Oxygenation of Bilirubin and its Pyrromethenone Models . Tet. 39 : 1893 – 1907 .
   Google Scholar
• Leoffler , M.C. and N.C. Li , 1985 . Role of Nitrogen and Sulfur-Containing Compounds in the Ageing of Liquid Fuels . Fuel , 64 : 1045 – 53 .
   Google Scholar
• Li , J. and N.C. Li , 1985 . Storage Stability of Jet Fuels . Fuel , 64 : 1041 – 46 .
   Web of Science ®Google Scholar
• Lightner , D.A. , Bisacchi , G.S. , and Norris , R.D. , 1976 . On the Mechanism of Sensitized Photooxygenatioa of Pyrroles . J. Am. Chem. Soc. , 98 : 802 – 7 .
   Google Scholar
• Mahoney , L.R. , 1969 . Antioxidants . Angew. Chem. IE , 8 : 547 – 55 .
   Web of Science ®Google Scholar
• Mayo , F.R. , 1968 . Free Radical Autoxidation of Hydrocarbons . Ace. Chem. Res. , 2 : 193 – 201 .
   Google Scholar
• Peroutka , S.J. , Ison , P.J. , Liu , and R.W. Barrett , 1986 . Artifactual High-Affinity and Saturable Binding of [3H]5-hydroxy-tryptamine Induced by Radioligand Oxidation . J. Neurochem. , 47 : 38 – 45 .
   Google Scholar
• Sinhababu , A.K. , and R.T. Borchardt , 1985 . Mechanism and Products of Autoxidation of 5.7-Dihydroxytryptamine . J. Am. Chem. Soc. , 170 : 7618 – 27 .
   Google Scholar
• Smith , E.B. and H.B. Jensen , 1967 . Autoxidation of Three 1-Alkylpyrroles . J. Org. Chem. , 32 : 3330 – 34 .
   Google Scholar
• Szmant , H.H. , Mata , A.J. , Namis , A.M. , and A.M. Panthananickal , 1976 . The Tiol-Olefin Cooxidation (TOCO) Reaction.4. Temperature Effects on Product Distribution in the TOCO Reaction of Indene and Aromatic Thiol . Tet. , 32 : 2665 – 80 .
   Web of Science ®Google Scholar