Skip to main content

Catalytic Activation of Methane and Ethane by Metal Compounds

  • Chapter
  • First Online:
Book cover Activation of Unreactive Bonds and Organic Synthesis

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 3))

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.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Axelrod MG, Gaffney AM, Pitchai R, Sofranko JA (1994) In: Curry-Hyde HE, Howe RF (eds) Natural gas conversion II; Elsevier, Amsterdam, p 93.

    Chapter  Google Scholar 

  2. Masters CD, Root DH, Attanasi ED (1991) Science 253:146.

    Article  Google Scholar 

  3. Starr C, Searl MF, Alpert S(1992) Science 256:981

    Article  Google Scholar 

  4. Recent reviews: (a) Sen A (1996) In: Herrmann WA, Cornils B (eds) Applied homogeneous catalysis with organometallic compounds, vol 2. VCH, Weinheim, p 1081.

    Google Scholar 

  5. Olah GA, Molnár A (1995) Hydrocarbon chemistry. Wiley, New York.

    Google Scholar 

  6. Crabtree RH (1995) Chem Rev 95:987.

    Article  CAS  Google Scholar 

  7. Labinger JA (1995) Fuel Process Technol 42:325.

    Article  CAS  Google Scholar 

  8. Hall TJ, Hargreaves JSJ, Huchings GJ, Joyner RW, Taylor SH (1995) Fuel Process Technol 42:151.

    Article  CAS  Google Scholar 

  9. Fierro JLG (1993) Catalysis Lett 22:67.

    Article  CAS  Google Scholar 

  10. Srivastava RD, Zhou P, Stiegel GJ, Rao VUS, Cinquegrane G (1992) Catalysis (London) 9:183.

    Article  CAS  Google Scholar 

  11. Brown MJ, Parkynes ND (1991) Catalysis Today 8:305

    Article  CAS  Google Scholar 

  12. Chemical & Engineering News April 8, 1996, p 17

    Google Scholar 

  13. Cheng WH, Kung HH (eds) (1994) Methanol production and use. Marcel Dekker, New York.

    Google Scholar 

  14. Wade LE, Gengelbach RB, Trumbley JL, Hallbauer WL (1981) In: Kirk-Othmer Encyclopedia of Chemical Technology, vol 15. Wiley, New York, p 398

    Google Scholar 

  15. Gerberich HR, Stautzenberger AL, Hopkins, WC (1980) In: Kirk-Othmer Encyclopedia of Chemical Technology, vol 11. Wiley, New York, p 231

    Google Scholar 

  16. Agreda VH, Zoeller JR (eds) (1993) Acetic acid and its derivatives. Marcel Dekker, New York.

    Google Scholar 

  17. Wagner FS (1978) In: Kirk-Othmer Encyclopedia of Chemical Technology, vol 1. Wiley, New York, p 124

    Google Scholar 

  18. Review: Forster D (1979) Adv Organomet Chem 17:255

    Article  Google Scholar 

  19. March J (1985) Advanced organic chemistry. Wiley, New York, p 620 and references therein.

    Google Scholar 

  20. Poutsma ML (1973) In: Kochi JK (ed) Free radicals, vol II. Wiley, New York, p 159

    Google Scholar 

  21. Olah G (1987) Acc Chem Res 20:422

    Article  CAS  Google Scholar 

  22. Reviews: (a) Parshall GW, Ittel SD (1992) Homogeneous catalysis. Wiley, New York, p 237.

    Google Scholar 

  23. Howard JA (1973) In: reference 8b, p 3

    Google Scholar 

  24. Reviews: (a) Drago RS (1992) Coord Chem Rev 117:185.

    Article  Google Scholar 

  25. Simándi LI (1992) Catalytic activation of dioxygen by metal complexes. Kluwer Academic, Dordrecht, p 74

    Google Scholar 

  26. Crabtree RH (1992) In: Patai S, Rappoport Z (eds) The chemistry of alkanes and cycloalkanes. Wiley, New York, p 653.

    Chapter  Google Scholar 

  27. Halpern J (1985) Inorg Chim Acta 100:41.

    Article  CAS  Google Scholar 

  28. Halpern J (1982) Acc Chem Res 15:238

    Article  CAS  Google Scholar 

  29. 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.

    Google Scholar 

  30. Armentrout PB, Beauchamp JL (1989) Acc Chem Res 22:315.

    Article  CAS  Google Scholar 

  31. Eller K, Schwarz H (1991) Chem Rev 91:1121.

    Article  CAS  Google Scholar 

  32. Schwarz H (1989) Acc Chem Res 22:282

    Article  CAS  Google Scholar 

  33. Simoes JAM, Beauchamp JL (1990) Chem Rev 90:629

    Article  CAS  Google Scholar 

  34. Arndtsen BA, Bergman RG, Mobley Peterson TH (1995) Acc Chem Res 28:154.

    Article  CAS  Google Scholar 

  35. Davies JA, Watson PL, Greenberg A, Liebman JF (eds) (1990) Selective hydrocarbon oxidation and functionalization. VCH, New York, Chaps 1-5.

    Google Scholar 

  36. Hill CL (ed) (1989) Activation and functionalization of alkanes. Wiley, New York.

    Google Scholar 

  37. Shilov AE, Shulpin GB (1997) Chem Rev 97:2879.

    Article  CAS  Google Scholar 

  38. Shilov AE (1984) Activation of saturated hydrocarbons by transition metal complexes. D. Reidel, Dordrecht

    Google Scholar 

  39. Reviews: (a) Groh SE, Nelson MJ (1990) In: reference 15c,p 305.

    Google Scholar 

  40. Valentine JS (1994) In: Bertini I, Gray HB, Lippard SJ, Valentine JS (eds) Bioinorganic chemistry. University Science Books, Mill Valley, CA, p 253.

    Google Scholar 

  41. Mansuy D, Battioni P (1993) In: Reedijk J (ed) Bioinorganic catalysis. Marcel Dekker, New York, p 395.

    Google Scholar 

  42. Omura T, Ishimura Y, Fujii-Kuriyama Y (eds) (1993) Cytochrome P-450. VCH, New York, p 17

    Google Scholar 

  43. Reviews: (a) Liu KE, Lippard SJ (1995) Adv Inorg Chem 42:263.

    Article  Google Scholar 

  44. Feig AL, Lippard SJ (1994) Chem Rev 94:759.

    Article  CAS  Google Scholar 

  45. Que L (1993) In: Reedijk J (ed) Bioinorganic catalysis. Marcel Dekker, New York, p 347

    Google Scholar 

  46. Zhang XX, Wayland BB (1994) J Am Chem Soc 116:7897.

    Article  CAS  Google Scholar 

  47. Wayland BB, Ba S, Sherry AE (1991) J Am Chem Soc 113:5305

    Article  CAS  Google Scholar 

  48. 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

    Article  CAS  Google Scholar 

  49. Sen A, Benvenuto MA, Lin M, Hutson AC, Basickes N (1994) J Am Chem Soc 116:998

    Article  CAS  Google Scholar 

  50. Lin M, Sen A (1992) J Chem Soc, Chem Commun 892

    Google Scholar 

  51. 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.

    Article  CAS  Google Scholar 

  52. Newcomb M, Le Tadic-Biadatti MH, Chestney DL, Roberts ES, Hollenberg PF (1995) J Am Chem Soc 117:12085

    Article  CAS  Google Scholar 

  53. Olah GA, Lin HC (1971) J Am Chem Soc 93:1259

    Article  CAS  Google Scholar 

  54. Review: Fabre PL, Devynck J, Trémillon B (1982) Chem Rev 82:591

    Article  Google Scholar 

  55. Basickes N, Hogan TE, Sen A (1996) J Am Chem Soc 118:13111

    Article  CAS  Google Scholar 

  56. Sen A (1991) Platinum Metals Rev 35:126.

    CAS  Google Scholar 

  57. Kao LC, Hutson AC, Sen A (1991) J Am Chem Soc 113:700

    Article  CAS  Google Scholar 

  58. Reviews: (a) Fujiwara Y, Takaki K, Taniguchi Y (1996) Synlett 591.

    Google Scholar 

  59. Nakata K, Yamaoka Y, Miyata T, Taniguchi Y, Takaki K, Fujiwara Y (1994) J Organomet Chem 473:329

    Article  CAS  Google Scholar 

  60. Stolarov IP, Vargaftik MN, Shishkin DI, Moiseev II (1991) J Chem Soc, Chem Commun 938.

    Google Scholar 

  61. Vargaftik MN, Stolarov IP, Moiseev II (1990) J Chem Soc, Chem Commun 1049

    Google Scholar 

  62. Hogan T, Sen A (1997) J Am Chem Soc 119:2642

    Article  CAS  Google Scholar 

  63. Motherwell WB, Crich D (1992) Free radical chain reactions in organic synthesis. Academic Press, London, p 4

    Google Scholar 

  64. Volkova LK, Tret'yakov VP (1995) Theoretical Experimental Chem 31:27

    Article  Google Scholar 

  65. Batamack P, Bucsi I, Molnár A, Olah, GA (1994) Catal Lett 25:11

    Article  CAS  Google Scholar 

  66. Review: Hall C, Perutz RN (1996) Chem Rev 96:3125

    Article  Google Scholar 

  67. Sen A, Benvenuto MA, Lin M, Hutson AC, Basickes N (1994) J Am Chem Soc 116:998.

    Article  CAS  Google Scholar 

  68. Sen A, Lin M, Kao LC, Hutson AC (1992) J Am Chem Soc 114:6385.

    Article  CAS  Google Scholar 

  69. Kao LC, Sen A (1991) J Chem Soc, Chem Commun 1242.

    Google Scholar 

  70. Basickes N, Sen A (1995) Polyhedron 14:197.

    Article  CAS  Google Scholar 

  71. Hutson AC, Lin M, Basickes N, Sen A (1995) J Organomet Chem 504:69

    Article  CAS  Google Scholar 

  72. Labinger JA, Herring AM, Lyon DK, Luinstra GA, Bercaw JE, Horváth IT, Eller K (1993) Organometallics 12:895.

    Article  CAS  Google Scholar 

  73. Luinstra GA, Labinger JA, Bercaw JE (1993) J Am Chem Soc 115:3004.

    Article  CAS  Google Scholar 

  74. Luinstra GA, Wang L, Stahl SS, Labinger JA, Bercaw JE (1994) Organometallics 13:755.

    Article  CAS  Google Scholar 

  75. Luinstra GA, Wang L, Stahl SS, Labinger JA, Bercaw JE (1995) J Organomet Chem 504:75

    Article  CAS  Google Scholar 

  76. Horváth IT, Cook RA, Millar JM, Kiss G (1993) Organometallics 12:8

    Article  Google Scholar 

  77. Wick DD, Goldberg KI (1997) J Am Chem Soc 119:10235.

    Article  CAS  Google Scholar 

  78. Stahl SS, Labinger JA, Bercaw JE (1996) J Am Chem Soc 118:5961.

    Article  CAS  Google Scholar 

  79. Zamashchikov VV, Popov VG, Rudakov ES (1994) Kinet Katal 35:436.

    Google Scholar 

  80. Theoretical study: Siegbahn Crabtree RH (1996) J Am Chem Soc 118:4442

    Article  Google Scholar 

  81. Freund MS, Labinger JA, Lewis NS, Bercaw JE (1994) J Mol Catal 87:L11.

    Article  CAS  Google Scholar 

  82. Geletii Yu V, Shilov AE (1983) Kinet Katal 24:486

    Google Scholar 

  83. Goldstein AS, Drago RS (1991) J Chem Soc, Chem Commun 21

    Google Scholar 

  84. Nizova GV, Süss-Fink G, Shul'pin GB (1997) J Chem Soc, Chem Commun 397

    Google Scholar 

  85. Michos M, Krajnik J, Sassano C, Crabtree RH (1993) Angew Chem, Int Ed Engl 32:1491.

    Article  Google Scholar 

  86. Krajnik J, Michos M, Crabtree RH (1993) New J Chem 17:805

    CAS  Google Scholar 

  87. Lin M, Sen A (1992) J Am Chem Soc 114:7307.

    Article  CAS  Google Scholar 

  88. Lin M, Hogan TE, Sen A (1997) J Am Chem Soc 119:6048

    Article  CAS  Google Scholar 

  89. Gosser LW (1987) U.S. Patent 4,681,751

    Google Scholar 

  90. Lin M, Sen A (1994) Nature 368:613.

    Article  CAS  Google Scholar 

  91. Lin M, Hogan TE, Sen A (1996) J Am Chem Soc 118:4574

    Article  CAS  Google Scholar 

  92. Chepaikin EG, Boiko GN, Bezruchenko AP, Lescheva AA, Grigoryan EA (1997) Doklady Phys Chem 353:120

    Google Scholar 

  93. Wang Y, Katagiri M, Otsuka K (1997) J Chem Soc, Chem Commun 1187

    Google Scholar 

  94. Barton DHR, Doller D (1992) Acc Chem Res 25:504

    Article  CAS  Google Scholar 

  95. Yamanaka I, Soma M, Otsuka K (1996) Chemistry Lett 565

    Google Scholar 

  96. Representative examples: (a) Tabushi I (1988) Coord Chem Rev 86:1.

    Article  Google Scholar 

  97. Otake M (1995) Chemtech 36.

    Google Scholar 

  98. Miyake T, Hamada M, Sasaki Y, Oguri M (1995) Appl Catal A: General 131:33.

    Article  CAS  Google Scholar 

  99. Teranishi T, Toshima N (1995) J Chem Soc, Dalton Trans 979.

    Google Scholar 

  100. Wang Y, Otsuka K (1995) J Catal 155:256

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1999 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

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

Download citation

  • DOI: https://doi.org/10.1007/3-540-68525-1_4

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-64862-8

  • Online ISBN: 978-3-540-68525-8

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics