Abstract
Information is given on the presence of diamondoids, hydrocarbons with a diamond-like structure, in oils and gas condensates. Methods for their isolation and analysis are described.
Similar content being viewed by others
REFERENCES
G. N. Gordadze and G. V. Rusinova, Geochem. Int. 42, 1086 (2004).
O. Pirali, M. Vervloet, J. E. Dahl, et al., Astrophys. J. 661, 919 (2007).
A. P. Jones, L. B. d’Hendecourt, S. Y. Sheu, et al., Astron. Astrophys. 416, 235 (2004).
E. I. Bagrii, Adamantanes (Nauka, Moscow, 1989) [in Russian].
R. Lin and Z. A. Wilk, Fuel 74, 1512 (1995).
I. K. Moiseev, N. V. Makarova, and M. N. Zemtsova, Usp. Khim. 68, 1102 (1999).
I. S. Morozov, V. I. Petrov and S. A. Sergeeva, Pharmacology of Adamantanes (Volgogradskaya Meditsinskaya Akademiya, Volgograd, 2001) [in Russian].
G. A. Mansoori, Adv. Chem. Phys. 136, 207 (2007).
A. A. Fokin, P. R. Schreiner, and H. Schwertfeger, Angew. Chem., Int. Ed. Engl. 47, 1022 (2008).
G. N. Gordadze, Pet. Chem. 48, 241 (2008).
E. I. Bagrii, R. E. Safir, and Yu. A. Arinicheva, Pet. Chem. 50, 1 (2010).
H. Schwertfeger and P. R. Schreiner, Xenobiotica 44, 248 (2010).
J. Filik, Carbon Based Nanomaterials, vol. 65–66 of Materials Science Foundations (monograph series), Ed. by N. Ali, A. Öchsner, and W. Ahmed (Trans Tech, Stafa-Zuerich, 2010).
A. I. Nekhaev, E. I. Bagrii, and A. L. Maximov, Pet. Chem. 51, 86 (2011).
E. A. Shokova and V. V. Kovalev, Usp. Khim. 80, 927 (2011).
T. Newhouse and P. S. Baran, Angew. Chem., Int. Ed. Engl. 50, 3362 (2011).
E. A. Shokova and V. V. Kovalev, Rus. J. Org. Chem. 48, 1007 (2012).
A. A. Fokin and P. R. Schreiner, Strategies and Tactics in Organic Synthesis (Elsevier, Amsterdam, 2012), Vol. 8, p. 317.
G. A. Mansoori, P. L. B. de Aroujo, and E. S. de Aroujo, Diamondoid Molecules with Applications in Biomedicine, Materials Science, Nanotechnology & Petroleum Science (World Scientific, Hackensack, NJ, 2012). www.worldscientific.com/worldscibooks/10.1142/7559.
P. L. B. de Araujo, G. A. Mansoori, and E. S. de Araujo, Int. J. Oil, Gas Coal Technol. 5, 316 (2012).
A. T. Balaban, Carbon Materials: Chemistry and Physics, vol. 6: Diamond and Related Nanostructures, Ed. by M. V. Diudea and C. L. Nagy (Springer, Dordrecht, 2013), p. 1.
L. Wanka, K. Iqbal, and P. R. Schreiner, Chem. Rev. 113, 3516 (2013).
M. A. Gunawan, J.-C. Hierso, D. Poinsot, et al., New J. Chem. 38, 28 (2014).
M. A. Gunawan, D. Poinsot, B. Domenichini, et al., Chemistry of Organo-Hybrids: Synthesis and Characterization of Functional Nano-Objects, Ed. by B. Charleux, C. Copéret, and E. Lacôte (Wiley, Hoboken, NJ, 2015), Ch. 3, p. 69.
G. N. Gordadze, Hydrocarbons in Petroleum Geochemistry (Theory and Practice) (RGUNG imeni Gubkina, Moscow, 2015) [in Russian].
M. V. Giruts and G. N. Gordadze, Chemistry and Geochemistry of Diamondoid Hydrocarbons (Nedra, Moscow, 2017) [in Russian].
S. Stauss and K. Terashima, Diamondoids: Synthesis, Properties, and Applications (Pan Stanford, Singapore, 2017).
C. Cupas, P. v. R. Schleyer, and D. J. Trecker, J. Am. Chem. Soc. 87, 917 (1965).
I. L. Karle and J. Karle, J. Am. Chem. Soc. 87, 918 (1965).
T. M. Gund, V. Z. Williams, Jr., E. Osawa, and P. v. R. Schleyer, Tetrahedron Lett. 11, 3877 (1970).
T. Courtney, D. E. Johnston, M. A. McKervey, and J. J. Rooney, J. Chem. Soc., Perkin Trans. 1, Issue 0, 2691 (1972).
T. M. Gund, E. Osawa, V. Z. Williams, Jr., and P. v. R. Schleyer, Org. Chem. 39, 2979 (1974).
V. Z. Williams, Jr., P. v. R. Schleyer, G. Gleicher J., and L. B. Rodewald, J. Am. Chem. Soc. 88, 3862. 1966.
W. Burns, M. A. McKerwey, and J. J. Rooney, J. Chem. Soc., Chem. Commun., No. 24, 965 (1975).
W. Burns, T. R. B. Mitchell, M. A. McKervey, and J. J. Rooney, J. Chem. Soc., Chem. Commun., No. 21, 893 (1976).
W. Burns, M. A. McKervey, T. R. B. Mitchell, and J. J. Rooney, J. Am. Chem. Soc. 100, 906 (1978).
J. E. P. Dahl, J. M. Moldowan, Z. Wei, et al., Angew. Chem., Int. Ed. Engl. 49, 9881 (2010).
M. V. Giruts, G. V. Rusinova, and G. N. Gordadze, Pet. Chem. 45, 141 (2005).
M. V. Giruts, G. V. Rusinova, and G. N. Gordadze, Pet. Chem. 46, 225 (2006).
M. V. Giruts and G. N. Gordadze, Pet. Chem. 47, 12 (2007).
G. N. Gordadze and M. V. Giruts, Pet. Chem. 48, 414 (2008).
Ch. M. Badmaev, M. V. Giruts, O. G. Erdnieva, et al., Pet. Chem. 51, 331 (2011).
Y. Wei, J. Li, C. Yuan, et al., Chem. Commun. 48, 3082 (2012).
A. A. Fokin, B. A. Tkachenko, P. A. Gunchenko, et al., Chem.-Eur. J. 11, 7091 (2005).
B. A. Tkachenko, N. A. Fokina, L. V. Chernish, et al., Org. Lett. 8, 1767 (2006).
P. R. Schreiner, N. A. Fokina, B. A. Tkachenko, et al., Org. Chem. 71, 6709 (2006).
A. A. Fokin, P. R. Schreiner, N. A. Fokina, et al., Org. Chem. 71, 8532 (2006).
A. A. Fokin, E. D. Butova, L. V. Chernish, et al., Org. Lett. 9, 2541 (2007).
H. Schwertfeger, C. Würtele, M. Serafin, et al., Org. Chem. 73, 7789 (2008).
H. Richter, H. Schwertfeger, P. R. Schreiner, et al., Synlett 2, 193 (2009).
A. A. Fokin, T. S. Zhuk, A. E. Pashenko, et al., Org. Lett. 11, 3068 (2009).
P. R. Schreiner, A. A. Fokin, H. P. Reisenauer, et al., J. Am. Chem. Soc. 131, 11292 (2009).
A. A. Fokin, B. A. Tkachenko, N. A. Fokina, et al., Chem.-Eur. J. 15, 3851 (2009).
A. A. Fokin, P. A. Gunchenko, A. A. Novikovsky, et al., Eur. J. Org. Chem. 2009, 5153 (2009).
T. M. Willey, J. R. I. Lee, J. D. Fabbri, et al., J. Electron. Spectrosc. Relat. Phenom. 172, 69 (2009).
A. A. Fokin, A. Merz, N. A. Fokina, et al., Synthesis, No. 6, 909 (2009).
H. Schwertfeger, C. Würtele, H. Hausmann, et al., Adv. Synth. Catal. 351, 1041 (2009).
H. Schwertfeger, M. Machuy, C. Würtele, et al., Adv. Synth. Catal. 352, 609 (2010).
H. Schwertfeger, C. Würtele, and P. R. Schreiner, Synlett, No. 3, 493 (2010).
P. A. Gunchenko and A. A. Fokin, Theor. Exp. Chem. 47, 343 (2012).
N. A. Fokina, B. A. Tkachenko, J. E. P. Dahl, et al., Synthesis 44, 259 (2012).
A. A. Fokin, L. V. Chernish, P. A. Gunchenko, et al., J. Am. Chem. Soc. 134, 13641 (2012).
G. A. Senchyk, A. B. Lysenko, H. Krautscheid, et al., Inorg. Chem. 52, 863 (2013).
A. A. Fokin, E. D. Butova, A. V. Barabash, et al., Synth. Commun. 43, 1772 (2013).
J. Zhang, Z. Zhu, Y. Feng, et al., Angew. Chem., Int. Ed. Engl. 52, 3536 (2013).
F. H. Li, J. D. Fabbri, R. I. Yurchenko, et al., Langmuir 29, 9790 (2013).
A. A. Fokin, T. S. Zhuk, A. E. Pashenko, et al., Org. Chem. 79, 1861 (2014).
P. Kahl, B. A. Tkachenko, A. A. Novikovsky, et al., Synthesis 46, 787 (2014).
C. Samann, V. Dhayalan, P. R. Schreiner, and P. Knochel, Org. Lett. 16, 2418 (2014).
A. A. Fokin, R. I. Yurchenko, B. A. Tkachenko, et al., J. Org. Chem. 79, 5369 (2014).
B. E. K. Barth, B. A. Tkachenko, J. P. Eußner, et al., Organometallics 33, 1678 (2014).
A. V. Barabash, N. A. Didukh, N. A. Kibal’nyi, et al. Russ. J. Org. Chem. 50, 1690 (2014).
Y. Nakanishi, H. Omachi, N. A. Fokina, et al., Angew. Chem., Int. Ed. Engl. 54, 10802 (2015).
T. S. Zhuk, T. Koso, A. E. Pashenko, et al., J. Am. Chem. Soc. 137, 6577 (2015).
L. Valentin, A. Henss, B.A. Tkachenko, et al., J. Coord. Chem. 68, 3295 (2015).
P. Kahl, J. P. Wagner, C. Balestrieri, et al., Angew. Chem., Int. Ed. Engl. 55, 9277 (2016).
O. Moncea, M. A. Gunawan, D. Poinsot, et al., J. Org. Chem. 81, 8759 (2016).
T. M. Swager and V. Schroder, Synfacts 12, Article 0918 (2016).
A. A. Fokin, A. E. Pashenko, V. V. Bakhonsky, et al., Synthesis 49, 2003 (2017).
F. Schibilla, J. Voskuhl, N. A. Fokina, et al., Chem.-Eur. J. 23, 16059 (2017).
N. T. Hoc, V. N. Rodionov, and A. A. Fokin, Org. Commun. 11, 75 (2018).
Y. Nakanishi, H. Omachi, N. A. Fokina, et al., Chem. Commun. 54, 3823 (2018).
J. Reiser, E. McGregor, J. Jones, et al., Fluid Phase Equilib. 117, 160 (1996).
P. Karasek, J. Planeta, and M. Roth, J. Chem. Eng. Data 53, 816 (2008).
L. Landt, K. Klunder, J. E. Dahl, et al., Phys. Rev. Lett. 103, Article 047402 (2009).
S. Roth, D. Leuenberger, J. Osterwalder, et al., Chem. Phys. Lett. 495, 102 (2010).
L. Landt, M. Staiger, D. Wolter, et al. J. Chem. Phys. 132, Article 024710 (2010).
L. Landt, C. Bostedt, D. Wolter, et al. J. Chem. Phys. 132, Article 144305 (2010).
W. A. Clay, J. R. Maldonado, P. Pianetta, et al., Appl. Phys. Lett. 101, Article 241605 (2012).
S. N. Yashkin, Russ. Chem. Bull. 62, 1131 (2013).
T. Zimmermann, R. Richter, A. Knecht, et al, J. Chem. Phys. 139, Article 084310 (2013).
R. Meinke, R. Richter, T. Möller, et al., J. Phys. B 46, Article 025101 (2013).
R. Meinke, R. Richter, A. Merli, et al. J. Chem. Phys. 140, Article 034309 (2014).
F. Yang, Y. Lin, J. E. P. Dahl, et al., J. Phys. Chem. 118, 7683 (2014).
B. B. Hassine, P. Negrier, M. Barrio, et al., Cryst. Growth Des. 15, 4149 (2015).
J. L. Zhang, H. Ishiwata, T. M. Babinec, et al., Nano Lett. 16, 212 (2016).
F. Yang, Y. Lin, M. Baldini, et al., J. Phys. Chem. Lett. 7, 4641 (2016).
D. Ebeling, M. Sekutor, M. Stiefermann, et al., ACS Nano 11, 9459 (2017),
M. Goulart, M. Kuhn, L. Kranabetter, et al., J. Phys. Chem. C 121, 10767 (2017).
T. Rander, T. Bischoff, A. Knecht, et al., J. Am. Chem. Soc. 139, 11132 (2017).
A. A. Fokin, T. S. Zhuk, S. Blomeyer, et al., J. Am. Chem. Soc. 139, 16696 (2017).
C. Tyborski, R. Gillen, A. A. Fokin, et al., J. Phys. Chem. C 121, 27082 (2017).
C. Tyborski, R. Meinke, R. Gillen, et al., J. Chem. Phys. 147, Article 044303 (2017).
H. Yan, K. T. Narasimha, J. Denlinger, et al., Nano Lett. 18, 1099 (2018).
M. A. Gebbie, H. Ishiwata, P. J. McQuade, et al., Proc. Natl. Acad. Sci. U. S. A. 115, 8284 (2018).
N. W. Rosemann, H. Locke, P. R. Schreiner, and S. Chatterjee, Adv. Opt. Mater. 6 (12), Article 1701162 (2018).
C. S. Sarap, B. Adhikari, S. Meng, et al., J. Phys. Chem. A 122, 3583 (2018).
A. T. Balaban, D. J. Klein, J. E. Dahl, and R. M. K. Carlson, Open Org. Chem. J. 1, 13 (2007).
M. Linnolahti, A. J. Karttunen, and T. A. Pakkanen, J. Phys. Chem. C 111, 18118 (2007).
A. A. Fokin and P. R. Schreiner, J. Mol. Phys. 107, 823 (2009).
W. Zhang, B. Gao, J. Yang, et al., J. Chem. Phys. 130, Article 054705 (2009).
C. Maciel, T. Malaspina, and E. E. Fileti, J. Phys. Chem. B 116, 13467 (2012).
H.-Q. Wu, R.-L. Zhong, S.-L. Sun, et al., J. Phys. Chem. C 118, 6952 (2014).
M. Bremer, H. Untenecker, P. A. Gunchenko, et al., J. Org. Chem. 80, 6520 (2015).
W. Zhang, B. Gao, J. Yang, et al., J. Chem. Phys. 130, Article 054705 (2009).
A. T. Balaban, J. Chem. Inf. Model. 52, 2856 (2012).
W. S. Wingert, Fuel 71, 37 (1992).
K. Grice, R. Alexander, and R. I. Kagi, Org. Geochem. 31, 67 (2000).
J. G. Li, P. Philip, and M. Z. Cui, Org. Geochem. 31, 267 (2000).
L. K. Schulz, A. Wilhelms, E. Rein, and A. S. Steen, Org. Geochem. 32, 365 (2001).
D. A. Azevedo, J. B. Tamanqueira, J. C. M. Dias, et al., Fuel 87, 2122 (2008).
I. Matyasik, Nafta-Gaz, No. 5, 310 (2011).
C. Fang, Y. Xiong, Q. Liang, and Y. Li, Org. Geochem. 47, 1 (2012).
C. Fang, Y. Xiong, Y. Li, et al., Geochim. Cosmochim. Acta 120, 109 (2013).
A. Ma, J. Nat. Gas Geosci. 1, 257 (2016).
H. S. Chung, C. S. H. Chen, R. A. Kremer, and J. R. Boulton, Energy Fuels 13, 641 (1999).
Lei Wang, J.-J. Zou, X. Zhang, and Li Wang, Energy Fuels 25, 1342 (2011).
K. W. Harrison, K. E. Rosenkoetter, and B. G. Harvey, Energy Fuels 32, 7786 (2018).
S. A. Stout and G. S. Douglas, Environ. Forens. 5, 225 (2004).
Z. D. Wang, C. Yang, B. Hollebone, and M. Fingas, Environ. Sci. Technol. 40, 5636 (2006).
M. M. Wu, D. M. Shen, and C. S. H. Chen, US Patent No. 306851 (1994).
D. M. Shen and M. M. Wu, US Patent No. 5345020 (1994).
C. Sinkel, S. Agarwal, N. A. Fokina, and P. R. Schreiner, J. Appl. Polym. Sci. 114, 2109 (2009).
J. E. Dahl, R. M. Carlson, and S. G. Liu, US Patent No. 7061073 (2006).
S. G. Liu, J. E. Dahl, and R. M. Carlson, Patent USA, No. 7304190 (2007).
J. E. Dahl, R. M. Carlson, and S. G. Liu, US Patent No. 7306671 (2007).
G. C. McIntosh, M. Yoon, S. Berber, and D. Tomanek, Phys. Rev. B 70, Article 045401 (2004).
R. M. Carlson, J. E. Dahl, and S. G. Liu, US Patent No. 7309476 (2004).
H. Ishiwata, Y. Acremann, A. Scholl, et al., Appl. Phys. Lett. 101, Article 163102 (2012).
M. A. Gunawan, D. Poinsot, B. Domenichini, et al., Nanoscale 7, 1956 (2015).
K. T. Narasimha, C. Ge, J. D. Fabbri, et al., Nat. Nanotechnol. 11, 267 (2016).
H. Yan, J. N. Hohman, F. H. Li, et al., Nat. Mater. 16, 349 (2017).
Y.-K. Tzeng, J. L. Zhang, H. Lu, et al., Nano Lett. 17, 1489 (2017).
M. A. Gunawan, O. Moncea, D. Poinsot, et al., Adv. Funct. Mater, 28, (2018).
P. A. Kalmykov, N. A. Magdalinova, and M. V. Klyuev, Pet. Chem. 55, 63 (2015).
U. M. Dzhemilev, A. R. Tuktarov, V. V. Korolev, and L. M. Khalilov, Pet. Chem. 51, 123 (2011).
E. Mathonneau, EP Patent No. 1637187 (2006).
J. C. Randel, F. C. Niestemski, A. R. Botello-Mendez, et al., Nat. Commun. 5, Article 4877 (2014).
W. L. Yang, J. D. Fabbri, T. M. Willey, et al., Science 316, 1460 (2007).
Y. Wang, B. A. Tkachenko, P. R. Schreiner, and A. Marx, Org. Biomol. Chem. 9, 7482 (2011).
H. Hopf, Angew. Chem., Int. Ed. Engl. 42, 2000 (2003).
S. Landa, V. Machacek, M. Mzourek, and M. Landa, Chim. Ind., No. 506 (1933); (Chem. Abstr. 27, 5949 (1933)).
S. Landa and V. Machacek, Collect. Czech. Chem. Commun. 5, 1 (1933).
I. M. Sokolova, V. V. Makarov, B. A. Kul’dzhaev, and N. N. Abryutina, Neftekhimiya 30, 723 (1990).
C. Fang, W. Wu, D. Liu, and J. Liu, J. Nat. Gas Geosci. 1, 93 (2016).
J. E. Dahl, J. M. Moldowan, K. E. Peters, et al., Nature 399, 54 (1999).
G. N. Gordadze and O. A. Aref’ev, Pet. Chem. 37, 381 (1997).
J. E. P. Dahl, J. M. Moldowan, T.`M. Peakman, et al., Angew. Chem., Int. Ed. Engl. 42, 20402003. V.
J. E. Dahl, S. G. Liu, and R. M. K. Carlson, Science 299, 96 (2003).
M. V. Giruts, A. R. Stroeva, G. A. Gadzhiev, Pet. Chem. 54, 10 (2014).
Ch. M. Badmaev, T. V. Okunova, M. V. Giruts, et al., Khim. Tekhnol. Topl. Masel, No. 3, 45 (2010).
M. V. Giruts, Ch. M. Badmaev, O. G. Erdnieva, et al., Pet. Chem. 52, 65 (2012).
M. V. Giruts, N. B. Derbetova, O. G. Erdnieva, et al., Pet. Chem. 53, 285 (2013).
T. X. Nguyen and R. P. Philp, Org. Geochem. 95, 1 (2016).
L. Polyakova P., S. I. Dzhafarov, V. A. Adigezalova, and E. M. Movsumzade, Chemical Composition and Properties of Oils from Different Horizons of the Naftalan Field (Reaktiv, Ufa, 2001) [in Russian].
S. Zhang, H. Huang, Z. Xiao, and D. Liang, Org. Geochem. 36, 1215 (2005).
C. Cai, Q. Xiao, C. Fang, et al., Org. Geochem. 101, 49 (2016).
M. V. Springer, D. F. Garcia, F. T. T. Gonçalves, et al., Org. Geochem. 41, 1013 (2010).
S. Bhattacharya, S. Dutta, and R. Dutta, J. Earth Syst. Sci. 123, 923 (2014).
G. Zhu, M. Wang, Y. Zhang, and Z. Zhang, Energy Fuels 32, 4996 (2018).
C. C. Fang, Y. Q. Xiong, Q. Y. Liang, and Y. Li, Org. Geochem. 47, 1 (2012).
R. A. Alexander, C. E. Knight, and D. D. Whitehurst, US Patent No. 4952747 (1990).
D. S. Swanson, US Patent No. 5461184 (1995).
R. D. Partridge and D. D. Whitehurst, US Patent No. 5019665 (1991).
C. S. H. Chen and S. E. Wentzek, US Patent No. 5120899 (1992).
C. S. H. Chen and S. E. Wentzek, US Patent No. 5414189 (1995).
R. A. Alexander and D. D. Whitehurst, US Patent No. 5139621 (1992).
L. Huang, S. Zhang, H. Wang, et al., Org. Geochem. 42, 566 (2011).
N. S. Vorob’eva and Al. A. Petrov, Pet. Chem. 41, 314 (2001).
C. Yang, Z. D. Wang, Hollebone B.P., et al., Environ. Forens. 7, 377. 2006.
Q. Liang, Y. Xiong, C. Fang, and Y. Li, Org. Geochem. 43, 83 (2012).
C. Fang, Y. Xiong, Q. Liang, and Y. Li, Org. Geochem. 47, 1 (2012).
C. Fang, Y. Xiong, Y. Li, et al., Marine Pet. Geol. 67, 197 (2015).
R. C. Silva, R. S. F. Silva, E. V. R. de Castro, et al., Fuel 112, 125 (2013).
Funding
This work was carried out as part of the State assignment to the Topchiev Institute of Petrochemical Synthesis of the Russian Academy of Sciences.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated by S. Zatonsky
Rights and permissions
About this article
Cite this article
Nekhaev, A.I., Maksimov, A.L. Diamondoids in Oil and Gas Condensates (Review). Pet. Chem. 59, 1108–1117 (2019). https://doi.org/10.1134/S0965544119100098
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0965544119100098