Tetramethylammonium hydroxide (TMAH) thermochemolysis of the aliphatic biopolymer cutan: Insights into the chemical structure

Organic Geochemistry

Volumn 24, Issue 6-7, 1996, Pages 641-650

  McKinney, D E ^a   Bortiatynski, J M ^a   Carson, D M ^a   Clifford, D J ^a   De Leeuw, J W ^b   Hatcher, P G ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b ROYAL NETHERLANDS INSTITUTE FOR SEA RESEARCH   (Netherlands)

Author keywords

aliphatic biopolymers; cutan; flash pyrolysis; tetramethylammonium hydroxide (TMAH); thermochemolysis

Indexed keywords

AMMONIUM COMPOUNDS; AROMATIC COMPOUNDS; DEGRADATION; ESTERS; NATURAL POLYMERS; PLANTS (BOTANY); PYROLYSIS; STRUCTURE (COMPOSITION); UNSATURATED COMPOUNDS;

AGAVE AMERICANA; CUTAN; DIAGENETICALLY RESISTANT BIOPOLYMERS; TETRAMETHYLAMMONIUM HYDROXIDE; THERMOCHEMOLYSIS;

BIOPOLYMERS;

CUTAN; FLASH PYROLYSIS; PYROLYSIS; THERMOCHEMOLYSIS; TMAH THERMOCHEMOLYSIS;

EID: 0030157182     PISSN: 01466380     EISSN: None     Source Type: Journal    
DOI: 10.1016/0146-6380(96)00055-1     Document Type: Conference Paper

References (42)

1. 1H dipolar interaction on cross polarization and carbon-proton dephasing. J. Am. Chem. Soc. 105, 6697-6704.
2. Anderson K. B. and Winans R. E. (1991) The nature and fate of natural resins in the geosphere. I. Evaluation of pyrolysis-gas chromatography-mass spectrometry for the analysis of natural resins and resinites. Analyt. Chem. 63, 2901-2908.
3. 13C NMR and elemental analyses. Geochim. Cosmochim. Acta 54, 2003-2013.
4. van Bergen P. F., Collinson M. E. and de Leeuw J. W. (1993) Chemical composition and ultrastructure of salvinialean microspore massulae and megaspores. Grana suppl. 1, 18-30.
5. van Bergen P. F., Collinson M. E. and de Leeuw J. W. (1994) Chemical and microscopical characterization of inner seed coats of fossil water plants. Geochim. Cosmochim. Acta 58, 231-239.
6. van Bergen P. F., van Moerkerken P., Barrie P. J., Collinson M. E. and de Leeuw J. W. (1995a) Sporopollenin revisited. In Organic Geochemistry: Developments and Applications to Energy, Climate, Environment, and Human History (Edited by Grimalt J. O. and Dorronsoro C.), pp. 988-990. A.I.G.O.A. Donostia-San Sebastian.
7. van Bergen P. F., Collinson M. E., Briggs D. E. G., de Leeuw J. W., Scott A. C., Evershed R. P. and Finch P.(1995) Resistant biomacromolecules in the fossil record. Acta Bot. Neerl. 44, 319-342.
8. Burczyk J. and Dworzanski J. P.(1988) Comparison of sporopollenin-like algal resistant biopolymer from the cell wall of Botryococcus Scenedesmus and Lycopodium clavatum by GC-pyrolysis. Phytochemistry 27, 2151-2153.
9. Challinor J. M.(1989) A pyrolysis-derivatization-gas chromatograph technique for the elucidation of some synthetic polymers. J. Anal. Appl. Pyrol. 16, 323-333.
10. Challinor J. M.(1991a) Structure determination of alkyd resins by simultaneous pyrolysis methylation. J. Anal. Appl. Pyrol. 18, 233-244.
11. Challinor J. M.(1991b) The scope of pyrolysis methylation reactions. J. Anal. Appl. Pyrol. 20, 15-24.
12. Clifford D. J., Carson D. M., McKinney D. E., Bortiatynski J. M. and Hatcher P. G.(1995) A new rapid technique for the characterization of lignin in vascular plants: thermochemolysis with tetramethylammonium hydroxide (TMAH). Org. Geochem. 23, 169-175.
13. Connan J. (1973) Diagenése naturelle et diagenèse artificielle de la matière organique a éléments végétaux prédominants. In Advances in Organic Geochemistry (Edited by Tissot B. and Bienner F.), pp. 73-95. Technip, Paris.
14. Derenne S., Largeau C., Sasadevall E., Tegelaar E. W. and de Leeuw J. W.(1988) Relationships between algal coals and resistant cell wall biopolymers of extant algae as revealed by Py-GC-MS. Fuel Process Technol. 20, 93-101.
15. Goth K., de Leeuw J. W., Puttman W. and Tegelaar E. W.(1988) Origin of Messel oil shale kerogen. Nature 336, 759-761.
16. Hartgers W. A., Sinninghe Damsté J. S. and de Leeuw J. W.(1995) Flash pyrolysis of sodium salts of functionalized fatty acids. J. Anal. Appl. Pyrol. 34, 191-217.
17. Hatcher P. G., Spiker E. C., Szeverenyi N. M. and Maciel B. E.(1983) Selective preservation: the origin of petroleum-forming aquatic kerogen. Nature 305, 498-501.
18. Hatcher P. G. and Clifford D. J.(1994) Flash pyrolysis and in situ methylation of humic acids from soil. Org. Geochem. 21, 1081-1092.
19. Hatcher P. G. and Minard R. D.(1995) Comment on the origin of benzenecarboxylic acids in pyrolysis methylation studies. Org. Geochem. 23, 991-994.
20. Hatcher P. G., Nanny M. A., Minard R. D., Dible S. D. and Carson D. M.(1995) Comparison of two thermochemolytic methods for the analysis of lignin in decomposing wood: the CuO oxidation method and the method of thermochemolysis with tetramethylammonium hydroxide (TMAH). Org. Geochem. 23, 881-888.
21. Kadouri A., Derenne S., Largeau C., Casadevall E. and Berkaloff C.(1988) Resistant biopolymer present in the outer walls of Botryococcus braunii, B-race. Phytochemistry 27, 551-557.
22. 15 NMR spectroscopic investigation on the formation of tobanite. In Organic Geochemistry: Developments and Applications to Energy, Climate, Environment, and Human History (Edited by Grimalt J. O. and Dorronsoro C.), pp. 943-945. A.I.G.O.A. Donostia-San Sebastian.
23. Largeau C., Derenne S., Casadevall L., Kadoure A. and Sellier N.(1986) Pyrolysis of immature torbanite and of the resistant biopolymer (PRB A) isolated from the extant alga Botryococcus braunii. Org. Geochem. 10, 1023-1032.
24. de Leeuw J. W., van Bergen P. F., van Aarssen B. G. K., Gatellier J.-P. L. A., Sinninghe Damsté J. S. and Collinson M. E.(1991) Resistant biomacromolecules as major contributors to kerogen. Phil. Trans. R. Soc. Lond. B. 333, 329-337.
25. de Leeuw J. W. and Baas J.(1993) The behavior of esters in the presence of tetramethylammonium salts at elevated temperatures; flash pyrolysis or flash chemolysis?. J. Anal. Appl. Pyrol. 26, 175-184.
26. Martin F., Gonzalez-Vila F. J., del Rio J. C. and Verdejo T.(1994) Pyrolysis derivatization of humic substances 1. Pyrolysis of fulvic acids in the presence of tetramethylammonium hydroxide. J. Anal. Appl. Pyrol. 28, 71-80.
27. Matsumoto G. I., Akiyama M., Watanuki K. and Torii T.(1990) Unusual distributions of long-chain n-alkanes and n-alkenes in Antarctic soil. Org. Geochem. 15, 403-412.
28. McKinney D. E. and Hatcher P. G. (1995) Characterization of coalified wood using thermochemolysis with tetramethylammonium hydroxide (TMAH). Inter. J. Coal Geol. (in press).
29. McKinney D. E., Carson D. M., Clifford D. J., Minard R. D. and Hatcher P. G.(1995) Off-line thermochemolysis versus flash pyrolysis for the in situ methylation of lignin: is pyrolysis necessary?. J. Anal. Appl. Pyrol. 34, 41-46.
30. 13C NMR analysis of present day and fossil plants. Naturwissenschaften 73, 579-585.
31. Nip M., Tegelaar E. W., Brinkhuis H., de Leeuw J. W., Schenck P. A. and Holloway P. J. (1986b) Analysis of modern and fossil plant cuticles by Curie-point Py-GC and Curie-point Py-GC-MS: recognition of a new, highly aliphatic and resistant biopolymer. Org. Geochem. 10, 769-778.
32. 13C NMR and IR spectroscopy in the analysis of a highly aliphatic biopolymer from plant cuticles. J. Anal. Appl. Pyrol. 11, 287-295.
33. Opella S. J. and Frey M. R.(1979) Selection of nonprotonated carbon resonances in solid-state nuclear magnetic resonance. J. Am. Chem. Soc. 101, 5854-5856.
34. 13C NMR and pyrolysis-methylation. Formation of benzenecarboxylic acid moieties during the coalification process. Org. Geochem. 22, 885-891.
35. del Rio J. C., Gonzalez-Vila F. J., Verdejo T. and Martin F. (1995) Pyrolysis-methylation of the kerogens and asphaltenes isolated from oil shales. In Organic Geochemistry: Developments and Applications to Energy, Climate, Environment, and Human History (Edited by Grimalt J. O. and Dorronsoro C.), pp. 994-997. A.I.G.O.A. Donostia-San Sebastian.
36. Saiz-Jimenez C.(1994) Analytical pyrolysis of humic substances: pitfalls limitations, and possible solutions. Environ. Sci. Technol. 28, 1773-1780.
37. Tegelaar E. W., de Leeuw J. W., Largeau C., Derenne S., Schulten H.-R., Müller R., Boon J. J., Nip M. and Sprenkels J. C. M. (1989a) Scope and limitations of several pyrolysis methods in the structural elucidation of a macromolecular plant constituent in the leaf cuticle of Agave americana L. J. Anal. Appl. Pyrol. 15, 29-54.
38. Tegelaar E. W., de Leeuw J. W., Derenne S. and Largeau C.(1989b) A reappraisal of kerogen formation. Geochim. Cosmochim. Acta 53, 3103-3106.
39. Tegelaar E. W., Hollman G., van der Vegt P., de Leeuw J. W. and Holloway P. J.(1995) Chemical characterization of the periderm tissue of some angiosperm species: recognition of an insoluble, non-hydrolyzable aliphatic biomacromolecule (Suberan). Org. Geochem. 23, 239.
40. Thompson D. L. and Reeves P. C.(1985) Phase-transfer-catalyzed alkylation of ethyl acetoacetate and diethyl malonate. J. Chem. Ed. 62, 907-908.
41. Wampler T. P. and Levy E. J. (1986) Effects of slow heating rates on products of polyethylene pyrolysis. Analyst 111, 1065-1067.
42. 13C nuclear resonance spectroscopy. Appl. Environ. Microbiol. 54, 1051-1060.