Geosynthesis of organic compounds. Part V - Methylation of alkylnaphthalenes

Organic Geochemistry

Volumn 31, Issue 6, 2000, Pages 523-534

  Bastow, Trevor P ^a   Alexander, Robert ^a   Fisher, Steven J ^a   Singh, Raj K ^a   Van Aarssen, Ben G K ^a   Kagi, Robert I ^a  

^a CURTIN UNIVERSITY   (Australia)

Author keywords

1,2,3,5,6,7 Hexamethylnaphthalene; Alkylation; Alkylnaphthalenes; Clay catalysis; Electrophilic aromatic substitution; Geosynthesis; Methylation

Indexed keywords

ALKYLNAPHTHALENES; METHYLATION;

ALKYLATION; CATALYSIS; CATALYSTS; CLAY; CRUDE PETROLEUM; SYNTHESIS (CHEMICAL);

AROMATIC HYDROCARBONS;

CRUDE OIL; NAPHTHALENE; ORGANIC COMPOUND; ORGANIC GEOCHEMISTRY;

EID: 0034046366     PISSN: 01466380     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0146-6380(00)00038-3     Document Type: Article

References (35)

1. Alexander R., Kagi R.I., Larcher A.V. Clay catalysis of alkyl hydrogen exchange reactions - reaction mechanisms. Organic Geochemistry. 6:1984;755-760.
2. Alexander R., Kagi R.I., Rowland S.J., Sheppard P.N., Chirila T.V. The effects of thermal maturity on distribution of dimethylnaphthalenes and trimethylnaphthaplenes in some Ancient sediments and petroleums. Geochimica et Cosmochimica Acta. 49:1985;385-395.
3. Alexander R., Strachan M.G., Kagi R.I., van Bronswijk W. Heating rate effects on aromatic maturity indicators. Geochimica et Cosmochimica Acta. 52:1986;1255-1264.
4. Alexander R., Bastow T.P., Kagi R.I., Singh R.K. Identification of 1,2,2,5-tetramethyltetralins and 1,2,2,5,6-pentamethyltetralin as racemates in petroleum. Journal of the Chemical Society, Chemical Communications. 23:1992;1712-1714.
5. Alexander R., Bastow T.P., Fisher S.J., Kagi R.I. Tetramethylnaphthalenes in crude oils. Polycyclic Aromatic Compounds. 3:1993;629-634.
6. Alexander R., Bastow T.P., Fisher S.J., Kagi R.I. Geosynthesis of organic compounds. II. Methylation of phenanthrene and alkylphenanthrenes Geochimica et Cosmochimica Acta. 59:1995;4259-4266.
7. Ansell, H.V., Sheppard, P.J., Simpson, C.F., Stroud, M.A., Talyor, R., 1979. Electrophilic aromatic substitution. Part 22. The effect of methyl sustituents on detritation of the 9-position of phenanthrene; tritium migration during exchange. Journal of the Chemical Society. Perkin I, 381-385.
8. Araki, M., Mukaiyama, T., 1974. Reaction of mixed carboxylic anhydrides with Grignard reagents. A useful method for the preparation of ketones. Chemistry Letters, 663-666.
9. Bastow T.P., Alexander R., Kagi R.I. Geosynthesis of organic compounds IV. Methylation of 1,2,7-trimethylnaphthalene. Polycyclic Aromatic Compounds. 9:1996;177-183.
10. Bastow T.P., Alexander R., Sosrowidjojo I.B., Kagi R.I. Pentamethylnaphthalenes and related compounds in sedimentary organic matter. Organic Geochemistry. 28:1998;585-595.
11. Bastow T.P., van Aarssen B.G.K., Alexander R., Kagi R.I. Biodegradation of aromatic land-plant biomarkers in some Australian crude oils. Organic Geochemistry. 30:1999;1229-1239.
12. Botto R.E., Hayatsu R., Carrado K.A., Winans R.E. Isotope labeling investigations in simulated coalification. a view of geological metamorphism Proc. 1989 Intl. Conf. Coal Sci. 1:1989;1-4.
13. Chen, T.S., Canonne, P., Leitch, L.C., 1973. Synthesis of 1,2,3-trimethyl-, 1,2,3,7-tetramethyl-, and 1,2,3,5,6,7-hexamethylnaphthalenes. Synthesis 620-621.
14. Derbyshire F.J., Whitehurst D.D. Study of coal conversion in polycondensed aromatic compounds. Fuel. 60:1981;655-662.
15. Ellis, L., 1994. Aromatic hydrocarbons in crude oil and sediments: molecular sieve separations and biomarkers. PhD dissertation, Curtin University of Technology.
16. Ellis L., Singh R.K., Alexander R., Kagi R.I. Geosynthesis of organic compounds. III. Formation of alkyltoluenes and alkylxylenes in sediments Geochimica et Cosmochimica Acta. 59:1995;5133-5140.
17. Ellis L., Singh R.K., Alexander R., Kagi R.I. Formation of isohexyl alkylaromatic hydrocarbons from aromatization-rearrangement of terpenoids in the sedimentary environment. a new class of biomarker Geochimica et Cosmochimica Acta. 60:1996;4747-4763.
18. Forster P.G., Alexander R., Kagi R.I. Identification of 2,2,7,8-tetramethyl-1,2,3,4-tetrahydronaphthalene in petroleum. Journal of the Chemical Society, Chemical Communications. 5:1989;274-276.
19. He S.J.X., Long M.A., Attalla M.I., Wilson M.A. Methylation of naphthalene by methane over substituted aluminophosphate molecular sieves. Energy and Fuels. 6:1992;498-502.
20. 13C over copper-exchanged silicoaluminophosphate. Energy and Fuels. 8:1994;286-287.
21. 13C over zeolitic catalysts at 400°C. Energy and Fuels. 9:1995;616-619.
22. Ioppolo-Armanios M., Alexander R., Kagi R.I. Geosynthesis of organic compounds. I-Alkylation of sedimentary phenols. Geochimica et Cosmochimica Acta. 59:1995;3017-3027.
23. Killops S.D. Novel aromatic hydrocarbons of probable bacterial origin in a Jurassic lacustrine sequence. Organic Geochemistry. 17:1991;25-36.
24. Martin E.L. The clemmensen reduction. Organic Reactions. 1:1942;155-209.
25. Püttmann W., Villar H. Occurrence and geochemical significance of 1,2,5,6-tetramethylnaphthalene. Geochimica et Cosmochimica Acta. 51:1987;3023-3029.
26. Radke M., Welte D.H., Willsch H. Geochemical study on a well in the Western Canada Basin. relation of the aromatic distribution pattern to maturity of organic matter Geochimica et Cosmochimica Acta. 46:1982;1-10.
27. Radke M., Willsch H., Leythaeuser D. Aromatic components of coal. relation of distribution pattern to rank Geochimica et Cosmochimica Acta. 46:1982;1831-1848.
28. Radke M., Garrigues P., Willsch H. Methylated dicyclic and tricyclic aromatic hydrocarbons in crude oils from the Handil field, Indonesia. Organic Geochemistry. 15:1990;17-34.
29. Radke M., Rullkotter J., Vriend S.P. Distribution of naphthalenes in crude oils from Java Sea. source and maturation effects Geochimica et Cosmochimica Acta. 58:1994;3675-3689.
30. Smith J.W., George S.C., Batts B.D. Pyrolysis of aromatic compounds as a guide to synthetic reactions in sediments. The APEA Journal. 34:1994;231-240.
31. Smith J.W., George S.C., Batts B.D. The geosynthesis of alkylaromatics. Organic Geochemistry. 23:1995;71-80.
32. Strachan M.G., Alexander R., Kagi R.I. Trimethylnaphthalenes in crude oils and sediments. effects of source and maturity Geochimica et Cosmochimica Acta. 52:1988;1255-1264.
33. van Aarssen B.G.K., Hessels J.K.C., Abbink O.A., de Leeuw J.W. The occurrence of polycyclic sesqui-, tri- and oligoterpenoids derived from a resinous polymeric cadinene in crude oils from South East Asia. Geochimica et Cosmochimica Acta. 56:1992;1231-1246.
34. van Aarssen B.G.K., Bastow T.P., Alexander R., Kagi R.I. Distributions of methylated naphthalenes in crude oils. indicators of maturity, biodegradation and mixing Organic Geochemistry. 30:1999;1213-1227.
35. van Duin A.C.T., Baas J.M.A., van de Graaf, de Leeuw J.W., Bastow T.P., Alexander R. Comparison of calculated equilibrium mixtures of alkylnaphthalenes and alkylphenanthrenes with experimental and sedimentary data - the importance of entropy calculations. Organic Geochemistry. 26:1997;275-280.