Abstract
Methane and ethane are the most abundant and the least reactive members of the hydrocarbon family, and their selective conversion to useful chemical products is of great scientific, as well as practical, interest. This review highlights some of the recent advances in the area of low temperature, catalytic, activation and functionalization of methane and ethane. Particular emphasis has been placed on C-H and C-C activation processes leading to the formation of oxygenates.
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References
Axelrod MG, Gaffney AM, Pitchai R, Sofranko JA (1994) In: Curry-Hyde HE, Howe RF (eds) Natural gas conversion II; Elsevier, Amsterdam, p 93.
Masters CD, Root DH, Attanasi ED (1991) Science 253:146.
Starr C, Searl MF, Alpert S(1992) Science 256:981
Recent reviews: (a) Sen A (1996) In: Herrmann WA, Cornils B (eds) Applied homogeneous catalysis with organometallic compounds, vol 2. VCH, Weinheim, p 1081.
Olah GA, Molnár A (1995) Hydrocarbon chemistry. Wiley, New York.
Crabtree RH (1995) Chem Rev 95:987.
Labinger JA (1995) Fuel Process Technol 42:325.
Hall TJ, Hargreaves JSJ, Huchings GJ, Joyner RW, Taylor SH (1995) Fuel Process Technol 42:151.
Fierro JLG (1993) Catalysis Lett 22:67.
Srivastava RD, Zhou P, Stiegel GJ, Rao VUS, Cinquegrane G (1992) Catalysis (London) 9:183.
Brown MJ, Parkynes ND (1991) Catalysis Today 8:305
Chemical & Engineering News April 8, 1996, p 17
Cheng WH, Kung HH (eds) (1994) Methanol production and use. Marcel Dekker, New York.
Wade LE, Gengelbach RB, Trumbley JL, Hallbauer WL (1981) In: Kirk-Othmer Encyclopedia of Chemical Technology, vol 15. Wiley, New York, p 398
Gerberich HR, Stautzenberger AL, Hopkins, WC (1980) In: Kirk-Othmer Encyclopedia of Chemical Technology, vol 11. Wiley, New York, p 231
Agreda VH, Zoeller JR (eds) (1993) Acetic acid and its derivatives. Marcel Dekker, New York.
Wagner FS (1978) In: Kirk-Othmer Encyclopedia of Chemical Technology, vol 1. Wiley, New York, p 124
Review: Forster D (1979) Adv Organomet Chem 17:255
March J (1985) Advanced organic chemistry. Wiley, New York, p 620 and references therein.
Poutsma ML (1973) In: Kochi JK (ed) Free radicals, vol II. Wiley, New York, p 159
Olah G (1987) Acc Chem Res 20:422
Reviews: (a) Parshall GW, Ittel SD (1992) Homogeneous catalysis. Wiley, New York, p 237.
Howard JA (1973) In: reference 8b, p 3
Reviews: (a) Drago RS (1992) Coord Chem Rev 117:185.
Simándi LI (1992) Catalytic activation of dioxygen by metal complexes. Kluwer Academic, Dordrecht, p 74
Crabtree RH (1992) In: Patai S, Rappoport Z (eds) The chemistry of alkanes and cycloalkanes. Wiley, New York, p 653.
Halpern J (1985) Inorg Chim Acta 100:41.
Halpern J (1982) Acc Chem Res 15:238
Reviews: (a) Armentrout PB (1990) In: Davies JA, Watson PL, Greenberg A, Liebman JF (eds) Selective hydrocarbon oxidation and functionalization. VCH, New York, p 467.
Armentrout PB, Beauchamp JL (1989) Acc Chem Res 22:315.
Eller K, Schwarz H (1991) Chem Rev 91:1121.
Schwarz H (1989) Acc Chem Res 22:282
Simoes JAM, Beauchamp JL (1990) Chem Rev 90:629
Arndtsen BA, Bergman RG, Mobley Peterson TH (1995) Acc Chem Res 28:154.
Davies JA, Watson PL, Greenberg A, Liebman JF (eds) (1990) Selective hydrocarbon oxidation and functionalization. VCH, New York, Chaps 1-5.
Hill CL (ed) (1989) Activation and functionalization of alkanes. Wiley, New York.
Shilov AE, Shulpin GB (1997) Chem Rev 97:2879.
Shilov AE (1984) Activation of saturated hydrocarbons by transition metal complexes. D. Reidel, Dordrecht
Reviews: (a) Groh SE, Nelson MJ (1990) In: reference 15c,p 305.
Valentine JS (1994) In: Bertini I, Gray HB, Lippard SJ, Valentine JS (eds) Bioinorganic chemistry. University Science Books, Mill Valley, CA, p 253.
Mansuy D, Battioni P (1993) In: Reedijk J (ed) Bioinorganic catalysis. Marcel Dekker, New York, p 395.
Omura T, Ishimura Y, Fujii-Kuriyama Y (eds) (1993) Cytochrome P-450. VCH, New York, p 17
Reviews: (a) Liu KE, Lippard SJ (1995) Adv Inorg Chem 42:263.
Feig AL, Lippard SJ (1994) Chem Rev 94:759.
Que L (1993) In: Reedijk J (ed) Bioinorganic catalysis. Marcel Dekker, New York, p 347
Zhang XX, Wayland BB (1994) J Am Chem Soc 116:7897.
Wayland BB, Ba S, Sherry AE (1991) J Am Chem Soc 113:5305
Periana RA, Taube DJ, Evitt ER, Löffler DG, Wentrcek, PR, Voss G, Masuda T (1993) Science 259:340. See also: Snyder JC, Grosse AV (1950) U.S. Patent 2,493,038
Sen A, Benvenuto MA, Lin M, Hutson AC, Basickes N (1994) J Am Chem Soc 116:998
Lin M, Sen A (1992) J Chem Soc, Chem Commun 892
Valentine AM, Wilkinson B, Liu KE, Komar-Panicucci S, Priestley ND, Williams PG, Morimoto H, Floss HG, Lippard SJ (1997) J Am Chem Soc 119:1818.
Newcomb M, Le Tadic-Biadatti MH, Chestney DL, Roberts ES, Hollenberg PF (1995) J Am Chem Soc 117:12085
Olah GA, Lin HC (1971) J Am Chem Soc 93:1259
Review: Fabre PL, Devynck J, Trémillon B (1982) Chem Rev 82:591
Basickes N, Hogan TE, Sen A (1996) J Am Chem Soc 118:13111
Sen A (1991) Platinum Metals Rev 35:126.
Kao LC, Hutson AC, Sen A (1991) J Am Chem Soc 113:700
Reviews: (a) Fujiwara Y, Takaki K, Taniguchi Y (1996) Synlett 591.
Nakata K, Yamaoka Y, Miyata T, Taniguchi Y, Takaki K, Fujiwara Y (1994) J Organomet Chem 473:329
Stolarov IP, Vargaftik MN, Shishkin DI, Moiseev II (1991) J Chem Soc, Chem Commun 938.
Vargaftik MN, Stolarov IP, Moiseev II (1990) J Chem Soc, Chem Commun 1049
Hogan T, Sen A (1997) J Am Chem Soc 119:2642
Motherwell WB, Crich D (1992) Free radical chain reactions in organic synthesis. Academic Press, London, p 4
Volkova LK, Tret'yakov VP (1995) Theoretical Experimental Chem 31:27
Batamack P, Bucsi I, Molnár A, Olah, GA (1994) Catal Lett 25:11
Review: Hall C, Perutz RN (1996) Chem Rev 96:3125
Sen A, Benvenuto MA, Lin M, Hutson AC, Basickes N (1994) J Am Chem Soc 116:998.
Sen A, Lin M, Kao LC, Hutson AC (1992) J Am Chem Soc 114:6385.
Kao LC, Sen A (1991) J Chem Soc, Chem Commun 1242.
Basickes N, Sen A (1995) Polyhedron 14:197.
Hutson AC, Lin M, Basickes N, Sen A (1995) J Organomet Chem 504:69
Labinger JA, Herring AM, Lyon DK, Luinstra GA, Bercaw JE, Horváth IT, Eller K (1993) Organometallics 12:895.
Luinstra GA, Labinger JA, Bercaw JE (1993) J Am Chem Soc 115:3004.
Luinstra GA, Wang L, Stahl SS, Labinger JA, Bercaw JE (1994) Organometallics 13:755.
Luinstra GA, Wang L, Stahl SS, Labinger JA, Bercaw JE (1995) J Organomet Chem 504:75
Horváth IT, Cook RA, Millar JM, Kiss G (1993) Organometallics 12:8
Wick DD, Goldberg KI (1997) J Am Chem Soc 119:10235.
Stahl SS, Labinger JA, Bercaw JE (1996) J Am Chem Soc 118:5961.
Zamashchikov VV, Popov VG, Rudakov ES (1994) Kinet Katal 35:436.
Theoretical study: Siegbahn Crabtree RH (1996) J Am Chem Soc 118:4442
Freund MS, Labinger JA, Lewis NS, Bercaw JE (1994) J Mol Catal 87:L11.
Geletii Yu V, Shilov AE (1983) Kinet Katal 24:486
Goldstein AS, Drago RS (1991) J Chem Soc, Chem Commun 21
Nizova GV, Süss-Fink G, Shul'pin GB (1997) J Chem Soc, Chem Commun 397
Michos M, Krajnik J, Sassano C, Crabtree RH (1993) Angew Chem, Int Ed Engl 32:1491.
Krajnik J, Michos M, Crabtree RH (1993) New J Chem 17:805
Lin M, Sen A (1992) J Am Chem Soc 114:7307.
Lin M, Hogan TE, Sen A (1997) J Am Chem Soc 119:6048
Gosser LW (1987) U.S. Patent 4,681,751
Lin M, Sen A (1994) Nature 368:613.
Lin M, Hogan TE, Sen A (1996) J Am Chem Soc 118:4574
Chepaikin EG, Boiko GN, Bezruchenko AP, Lescheva AA, Grigoryan EA (1997) Doklady Phys Chem 353:120
Wang Y, Katagiri M, Otsuka K (1997) J Chem Soc, Chem Commun 1187
Barton DHR, Doller D (1992) Acc Chem Res 25:504
Yamanaka I, Soma M, Otsuka K (1996) Chemistry Lett 565
Representative examples: (a) Tabushi I (1988) Coord Chem Rev 86:1.
Otake M (1995) Chemtech 36.
Miyake T, Hamada M, Sasaki Y, Oguri M (1995) Appl Catal A: General 131:33.
Teranishi T, Toshima N (1995) J Chem Soc, Dalton Trans 979.
Wang Y, Otsuka K (1995) J Catal 155:256
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Sen, A. (1999). Catalytic Activation of Methane and Ethane by Metal Compounds. In: Murai, S., et al. Activation of Unreactive Bonds and Organic Synthesis. Topics in Organometallic Chemistry, vol 3. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-68525-1_4
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DOI: https://doi.org/10.1007/3-540-68525-1_4
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