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Anthraquinones As Inhibitors of Sulfide Production from Sulfate-Reducing Bacteria

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Anthraquinones As Inhibitors of Sulfide Production from Sulfate-Reducing Bacteria Europaisches Patentamt 19 European Patent Office Office europeen des brevets © Publication number: 0 525 073 B1 12 EUROPEAN PATENT SPECIFICATION © Date of publication of patent specification © int. ci.5: A01N 35/06, C12Q 1/04, 25.05.94 Bulletin 94/21 C12Q 1/18 © Application number : 91908405.3 © Date of filing : 19.03.91 © International application number : PCT/US91/01734 @ International publication number : WO 91/15954 31.10.91 Gazette 91/25 @ ANTHRAQUINONES AS INHIBITORS OF SULFIDE PRODUCTION FROM SULFATE-REDUCING BACTERIA. © Priority: 18.04.90 US 510763 © Proprietor : E.I. DU PONT DE NEMOURS AND 07.02.91 US 652406 COMPANY 1007 Market Street Wilmington Delaware 19898 (US) @ Date of publication of application 03.02.93 Bulletin 93/05 © Inventor : ANDERSON, Albert Gordon 2410 St. Francis Street (45) Publication of the grant of the patent : Wilmington, DE 19808 (US) 25.05.94 Bulletin 94/21 Inventor : COOLING, Frederick Beiswanger, III 521 Cabot Drive @ Designated Contracting States : Hockessin, DE 19707-0731 (US) AT BE CH DE ES FR GB GR IT LI NL Inventor : ODOM, James Martin 28 Hilltop Road Avondale, PA 19311 (US) © References cited : Inventor : WEIMER, Paul James EP-A- 0 094 721 14 Oxwood Circle CH-A- 505 900 Madison, Wl 53717 (US) CH-A- 614 466 GB-A- 2 155 453 US-A- 4 532 117 © Representative : Jones, Alan John et al CHEMICAL ABSTRACTS, vol. 43, no. 7, 10 April CARPMAELS & RANSFORD 1949, Columbus, Ohio, US; M. ANCHEL: 43 Bloomsbury Square "Identification of the antibiotic substance London, WC1A 2RA (GB) from cassia reticulata as 4,5-dihydroxyanthra- CO quinone-2-carboxylic acid", abstract no. 3062f CO h- o If) CM If) Note : Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been UJ filed until the opposition fee has been paid (Art. 99(1) European patent convention). Jouve, 18, rue Saint-Denis, 75001 PARIS EP 0 525 073 B1 Description FIELD OF THE INVENTION 5 The first aspect of the invention is the novel discovery that many anthraquinones, or the corresponding anthraquinol or tetrahydroanthraquinone derivatives thereof, inhibit sulfide production from sulfate-reducing bacteria and are thus potentially useful chemicals for treating industrial situations where biological sulfide gen- eration is a problem. Examples include the prevention of souring of oil wells with hydrogen sulfide orthe con- tamination of surface operations such as pipelines, and storage tanks with hydrogen sulfide. The second as- 10 pect is the relative specificity of the anthraquinones, anthraquinols ortetrahydroanthraquinones for the proc- ess of respiratory sulfate reduction. This aspect extends the useful application of these inhibitors to situations where only sulfate-reducers should be inhibited, but not other bacterial types, as for example, in sewage treat- ment where bacterial digestion is desirable but sulfide generation is not, or in the utilization of biomass for the generation of fuel gases where hydrogen sulfide is a deleterious contaminant, or in the agricultural sphere 15 where sulfide generation and consequent soil alkalinity may be a problem for rice cultivation. Hereinafter, the term "anthraquinone(s)" as used in this application is defined to include anthraquinone compounds, the corresponding anthraquinol derivatives, the corresponding tetrahydroanthraquinone com- pounds, the corresponding octahydroanthraquinone compounds, and the reduced derivatives thereof. It is proposed that the anthraquinones are a novel treatment for the problem of hydrogen sulfide pollution 20 by virtue of their relatively benign environmental impact, which is due to their relatively specific toxicity for respiratory sulfide generation. As a consequence, these compounds may be useful in treating situations that are incompatible with the use of broad-spectrum biocides. BACKGROUND OF THE INVENTION 25 A recent review by Widdel (1986) in Anaerobic Bacteria in Habitats Other Than Man, pp 157-184, Eds. Barnes and Mead, Blackwell Scientific Publications, includes as sulfate-reducing bacteria the genera: Desul- fovibrio, Desulfotomaculum, Desulfobacter, Desulfobulbus, Desulfococcus, Desulfonema, Desulfosarcina and Thermodesulfobacterium. Significant inter- and even intra-generic differences exist in terms of morphologies, 30 ecological niches, and metabolic capabilities. However, all respiratory sulfate-reducing bacteria are strict anae- robes which are poisoned by oxygen. The preponderance of isolates are eubacterial and classified as Desul- fovibrio although extremely thermophilic archaebacterial sulfate-reducers have been isolated from undersea volcanoes (Stetter et al., 1987 Science 236:822-825). Thus, the term sulfate-reducer encompasses a broad spectrum of organisms across both eubacterial and archaebacterial branches of bacterial phylogeny. 35 The metabolic capabilities of the genus Desulfovibrio reflect the range of available niches. Utilization of sulfate as an electron sink and respiratory substrate is the characteristic and predominant mode of energy gen- eration. However, nitrate, elemental sulfur, f umarate and other sulfur oxy-acids, when present, can also serve in a similar capacity for a few species. These bacteria are specialists adapted to use the metabolic end-prod- ucts of primary degradative bacteria for electron and carbon sources as described by Odom et al., 1981 in 40 Trends in the Biology of Fermentations for Fuels and Chemicals, Eds. Hollaender, Rabson, Rogers, Pietro, Valentine, and Wolfe, Plenum Publishing and Odom etal., 1984 Ann. Rev. Microbiol. 38:551-592. Organic acids such as lactate, formate, and pyruvate, alcohols such as ethanol, and molecular hydrogen are the preferred electron sources for sulfate reduction. Acetate, which is the metabolic end-product of the Desulfovibrio, can be utilized by Desulfobacter as an electron donor with carbon dioxide as the sole end product (Stetter et al., 45 1 987 Science 236:822-825). Thus, the sulfate-reducers can effect total mineralization of organic matter from the level of alcohols and acids to carbon dioxide. The sulfate-reducers play a special role in methane formation as it occurs in sewage treatment and fresh- water bogs. In these situations, where sulfate concentrations are very low, the sulfate-reducer enters into a symbiotic relationship with methane-producing bacteria (methanogen) wherein the sulfate-reducers actually so produce hydrogen from organic acids and alcohols only if the hydrogen is continuously consumed by the me- thanogen. This important process, termed interspecies hydrogen transfer, is a vital link in the food chain from complex polymers to methane (Odom et al., 1981 in Trends in the Biology of Fermentations for Fuels and Chemicals, Eds. Hollaender, Rabson, Rogers, Pietro, Valentine, and Wolfe, Plenum Publishing). The most in- tensively studied aspect has been hydrogen metabolism due to its inherent relationship with methane (fuel) 55 generation from biomass. Similarly, the implication of microbial hydrogen uptake in the phenomenon of anae- robic corrosion of steel according to the theory of cathodic depolarization has stimulated research into the the hydrogen metabolism of sulfate-reducers as well as other microbial types (Von Wolzogen Kuhretal., 1934 Water 18:147-165, Odom etal., 1984 Ann. Rev. Microbiol. 38:551-592, Pankhania etal., 1986 J. Gen. Microbiol. 2 EP 0 525 073 B1 132:3357-3365, and Ringas et al., 1987 Corrosion Engineering 44 #6:386-396). There are currently approximately 130 different industrial biocide products registered with the U.S. En- vironmental Protection Agency which are produced by over a 100 different companies in the U.S. alone. The 5 leading biocides are halogenated compounds, which make up 35% of total sales, while quarternary detergents and phenolics represent 22% of total sales. Organometallic compounds, inorganic compounds, aldehydes, ani- lides, and organosulfur compounds make up the rest of the total. None of the known commercial chemicals are specif ic for sulfate-reducing bacteria, but many have demonstrated effectiveness against sulfate-reducers. Below are discussed some of the more commonly used inhibitors against sulfate-reducing bacteria. 10 Organo-sulfur or sulfur-nitrogen compounds contain some of the more effective industrial biocides against sulfate-reducers. The isothiazoline containing compounds (produced by Rohm & Haas, Inc. under the name "Kathon®") are effective against, but not specific for, sulfate-reducers at 12 ppm (Oil and Gas Journal March 8, 1982, p253). The thiocyanate containing compounds are effective in the range of 5-30 ppm (i.e. "Cytox®"). 2,2-Dibromo-3-nitrilopropionamide (DBNPA) is produced by Nalco, Inc. and is claimed to be particularly ef- 15 fective against sulfate-reducing bacteria at 3-12 ppm. This compound is also a good surfactant and corrosion inhibitor. Recently, Nalco, Inc. has introduced an oilfield biocide claimed to be effective against sulfate-reduc- ers. The product is essentially metronidazole, which is a pharmaceutical originally used to treat Trichosomal infections. The compound is not specific for sulfate-reducers but is claimed to be generally effective against anaerobic bacteria. 20 Acids and aldehydes are also effective inhibitors of sulfate-reducers. Glutaraldehyde is widely used in wa- ter flooding situations at concentrations in the range of 100
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