IJOC  Vol.1 No.3 , September 2011
Chemical and Microbiological Hydrolysis of Epoxides of Acetylene Series
ABSTRACT
The chemical and microbiological hydrolyses of epoxide compounds of acetylene series have been comparatively carried out. It has been shown that as distinguished from chemical one in microbiological hydrolysis along with corresponding optically active glycols, ketoalcohols of acetylene series are also formed. It has been also defined that the synthesized glycols of acetylene series have bactericide properties related to sulfate-reducing bacteria at concentration of 100 - 200 mg/l. It has been established that an introduction of electron-acceptor chlorine atoms in molecules influence on decreasing of bactericide activity of acetylene glycols.

Cite this paper
nullM. Veliyev, M. Salmanov, S. Aliyeva, M. Shatirova and G. Yagubova, "Chemical and Microbiological Hydrolysis of Epoxides of Acetylene Series," International Journal of Organic Chemistry, Vol. 1 No. 3, 2011, pp. 113-118. doi: 10.4236/ijoc.2011.13017.
References
[1]   I. A. Maretina and B. A. Trophimov, “Endiine Antibiotics and Their Models: New Possibilities of Chemistry of Acetylene,” Uspekhi Khimii, Vol. 75, No. 9, 2006, pp. 913-935.

[2]   D. M. Rudkovskiy, M. M. Ketslakh and F. A. Eppel, “Multiatom Alcohols,” Khimiya, Leningrad, 1972, p. 168.

[3]   A. A. Kunitskiy, N. V. Artyemeva, T. N. Antonova, E. M. Chabutkina, A. S. Danilova and G. N. Koshel, “Synthesis of Unsaturated Alycyclic 1,2-Diols С8, С12 on the Basis of Monoepoxides of Cycloolefins,” Neftekhimiya, Vol. 37, No. 3, 1997, pp. 259-265.

[4]   A. A. Kunitskiy, S. A. Mashina, E. M. Chabutkina, T. N. Antonova, N. V. Artyemeva and A. S. Danilova, “Conversion of Alycyclic Monoepoxides С8, С12 of Unsaturated and Saturated Series in the Process of Their Hydration,” Neftekhimiya, Vol. 39, No. 6, 1999, pp. 456-460.

[5]   M. G. Veliev, O. A. Sadigov, Kh. M. Alimardanov and M. I. Shatirova, “Investigation of Halogenation Reaction of Vinyl-, Allylacetylene Compounds and Some Chemical Conversions of the Prepared Products,” Journal of Organic Chemistry, Vol. 43, No. 11, 2007, pp. 1609-1616.

[6]   M. G. Veliev, O. A. Sadigov, M. I. Shatirova and Kh. M. Alimardanov, “Investigation Hypohalogenation Reaction of Functionally Substituted Norbornenes of Acetylenes series,” Journal of Organic Chemistry, Vol. 44, No. 9, 2008, pp. 1298-1307.

[7]   A. S. Dykman, N. S. Imyanitov, S. A. Polyakov and K. A. Vershinin, “Hydration of Isoprene,” Russian Journal of Applied Chemistry, Vol. 82, No. 11, 2009, pp. 1822- 1829.

[8]   S. Pedragosa-Morean, A. Archelas and R. Furstoss, “Microbiological Transformations. 28. Enantiocomple- mentery Epoxide Hydrolyses as a Preparative Access to Both Enantiomers of Styrene Oxide,” Journal of Organic Chemistry, Vol. 58, No. 20, 1993, pp. 5533-5536. doi:10.1021/jo00072a044

[9]   P. L. Barili, G. Berti, G. Catelani, F. Colonna, E. Mastrorilli and M. Paoli, “Preparation of Isobutyl 3,4-Anhy- dro-2,6-Dioboxy-dl-?-Lyxo-Hexopyranoside and Its Kinetic Resolution with Microsomal Epoxide Hydrolase,” Tetrahedron, Vol. 45, No. 5, 1989, pp. 1553- 1566.

[10]   X. J. Chen, A. Archelas and E. Furstoss, “Microbio- logical Transformations. 27. The First Examples for Preparative-Scale Enantioselective or Diastereoselective Epoxside Hydrolyces Using Microorganisms. An Unequivocal Access to All Bisabolol Stereoisomers,” Journal of Organic Chemistry, Vol. 58, No. 20, 1993, pp. 5528-5532. doi:10.1021/jo00072a043

[11]   A. A. Babashly, “Investigation of Phenol Degradation Status of Bacteria Isolated from Azerbaijan Shores of Middle/South Caspian,” Ph.D. Dissertation, Institute of Microbiology of Azerbaijan National Academy of Sci- ences, Baku, 2010.

[12]   M. A. Salmanov, M. G. Veliev, A. A. Babashly and N. R. Bektashi, “Biodegradation of Chlorine-Containing aro- Matic Xompounds with Bacteria Isolated from Azerbaijan Shores of Caspian Sea,” Vesrnik MGOU, Series of “Natural Sciences”, No. 2, 2010, pp. 57-62.

[13]   Yu. N. Karasevich, “Bases of Selection of Microorganisms Utilizing Synthetic Organic Compounds,” Nauka, Moscow, 1982.

[14]   G. K. Skryabin and E. L. Golovlev, “Use of Microorganisms in Organic Synthesis,” Nauka, Moscow, 1976.

[15]   S. R. Alieva, “Filamentous Fungi of Shore of Apsheron Peninsula of Caspian Sea and Degradation of Oil Hydrocarbons by Them,” Ph.D. Dissertation, Institute of Botany of Azerbaijan National Academy of Sciences, Baku, 2008.

[16]   M. Veliyev, S. Aliyeva and M. Shatirova, “Chemical and Microbiological Oxidation of Cyclic Alcohols and Hydrocarbons,” International Conference on Organic Chemistry, Erzurum-Turkey, 2007.

[17]   M. G. Veliev, B. Danielsson, M. A. Salmanov, S. R. Aliyeva and N. R. Bektashi, “Biodegradation of Baku Oil and Hydrocarbons by Micromycetes,” Petroleum Chemistry, Vol. 48, No. 1, pp. 56-62. doi:10.1134/S0965544108010118

[18]   M. A. Salmanov, M. G. Veliyev, S. R. Aliyeva and N. R. Bektashi, “Degradation of Baku Oils and Individual Aromatic Hydrocarbons by Micromycetes,” Proceedings of Azerbaijan NAS, No. 1-2, 2007, pp. 150-157.

[19]   A. E. Smorodin, N. M. Agaev, M. M. Guseinov, L. I. Antronov, M. G Veliyev and A. V. Allakhverdieva, “Suppression of Sufate-Reducing Bacteria by Cyclic Compounds of Acetylene Series,” Protection of Metals, No. 31983, pp. 471-473.

[20]   M. G. Veliev, N. M. Agaev, M. I. Shatirova, A. Z. Chalabieva, G. D. Geydarova and S. S. Alieva, “Allylacetylene and Their Derivatives as Inhibitors of Steel Corrosion in Sulphuric Acid,” Zhurnal Prikladnoy Khimii, Vol. 79, No. 11, 2006, pp. 1848-1854.

[21]   V. I. Romanenko and S. I. Kuznetsov, “Ecology of Microorganisms of Fresh Basins,” Nauka, Moscow, 1974.

[22]   M. G. Veliev, A. Z. Chalabieva, I. A. Vezirova, M. I. Shatirova and M. I. Gadzhieva, “Functional Derivatives of Acetylene as Reagents for Suppression of Growth of Sulfate-Reducing Bacteria at Oil-Extraction,” Neftekhimi- ya, Vol. 50, No. 6, 2010, pp. 1-5.

[23]   M. I. Shatirova, “Synthesis and Properties of 2-Chlor (brom)substituted Allylacetylene Alcohols,” Ph.D. Dissertation, Azerbaijan State Oil Academy, Baku, 1999.

[24]   S. F. Karaev, I. A. Shikhiev, M. G. Mirzakhanova and S. R. Yuzbasheva, “Some Chlorinated Alkinols and Their Conversions,” Azerbaijan Chemical Journal, No. 3, 1970, pp. 77-80.

 
 
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