Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/23—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
  • C10L1/231—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites nitro compounds; nitrates; nitrites

Definitions

• This invention relates to a process for inhibiting the growth of bacterial and fungal microorganisms and to compositions therefor. More particularly this invention relates to the use of nitro-substituted benzonitriles as antibacterial and antifungal agents.
• antibacterial and antifungal agents employed in this invention have the following structural formula:
• nitro group may be substitued at any of the available positions on the benzene ring and wherein Y and Z may be hydrogen, lower alkoxy containing from 1 to 4 carbon atoms, lower alkyl containing from 1 to 4 carbon atoms, cyano, or nitro. Where only one nitro group is present, it is preferred that this group be in a position ortho or para to the cyano substituent.
• the compounds employed in the practice of this invention possess a broad spectrum of antibacterial and antifungal activity and are usfeul for suppressing the growth of undesirable microorganisms in a wide variety of applications.
• an inhibitory concentration of the compounds can be included as one of the components of the disinfectant solution commonly employed in the foot baths which are used around swimming pools, shower rooms and the like, to minimize the spread of bac terial and fungal infections.
• the compounds may also be employed in the solutions utilized in the cleaning of floors in such public areas.
• the antibacterial and antifungal agents of this invention can also be employed as additives in paints, in the treatment of leather to impart resistance to attack by microorganisms and in like situations where the outstanding antibacterial and antifungal properties of these agents are desired.
• An especially useful application of the subject compounds lies in their use as additives in hydrocarbon fuels for the suppression of growth of microorganisms therein.
• a further object of this invention is to provide hydrocarbon fuel compositions containing additives which prevent the growth of undesirable bacterial and fungal microorganisms.
• Another object is to provide such compositions which do not produce corrosive by-products upon combustion.
• Still another object of the invention is to provide a process for inhibiting the growth of such microorganisms in hydrocarbon fuels.
• the outstanding antibacterial and antifungal properties of the compounds employed in this invention provide an excellent means for controlling the growth of objectionable mold, bacteria, and fungi in hydrocarbon fuels and that the difiiculties arising from the presence of scums and other residues produced by the microorganisms are circumvented.
• the hydrocarbon fuel is in contact with an aqueous phase, this being the state in which such fuels are usually encountered under normal storage conditions.
• the antibacterial and antifungal agents employed in the practice of this invention include, in addition to the simple nitrobenzonitriles, compounds containing a plurality of nitro and cyano groups, and, in fact, a highly preferred compound is 2,4-dinitrobenzonitrile.
• Other compounds which are used effectively to inhibit bacteria and fungi include 2,3-dinitrobenzonitrile, 2-nitro-4-methoxybenzonitrile, 2-nitro-3-rnethylbenzonitrile, 2-nitro-6-methoxybenzonitrile, 2,6-dinit-robenzonitrile, 3,5-dinitrobenzonitrile, 2,S-dinitrobenzontittrile, 3,4-dinitrobenzonitrile, Z-nitrobenzonitrile, 3-nitrobenzonitrile, 4-nitrobenzontrile, Z-nitrophthalonitrile, 2-nitroterephthalonitrile, 2-nitro-4- butoxybenzonitrile, 2-nitro-4-t-butylbenzonitrile, and the like.
• nitriles are extremely effective against a representative group of microorganisms isolated from contaminated IP-4 jet engine fuel.
• bacterial and fungal organisms isolated therefrom are two species of Bacillus, Pseudomonas acluginosal, a green fungus tentatively identified as a species of Penicillium, a brown fungus thought to be a species of Hormodendrum, Cladiosporum resinae, a black fungus tentatively classified as a species of Aspergillus, and a gray fungus and a yellow-green fungus both of which remain unidentified. All of these organisms are controlled to a highly effective degree by the compounds of this invention, as is apparent from the follow ing description of the method used in determining the activity of the subject compounds by an agar plate procedure.
• the compounds employed in this invention possess a number of outstanding advantages. Because of the enormous volumes of hydrocarbon fuels consumed, economic considerations require that any 'antimiorcbial agent employed therein be effective at relatively low concentrations and be available at a reasonable cost.
• the nitrobenzonitriles of this invention are effective against the microorganisms contaminating hydrocarbon fuels at concentrations as low as about 10 ppm. and are in addition very inexpensive.
• the partition coefficients of the compounds for fuel water mixtures are such that a favorable distribution of the compounds between the fuel and aqueous phases results.
• a further advantage of these compounds is that they are completely consumed in the combustion process, leaving neither solid residues nor corrosive by-products which could themselves give rise to serious problems.
• nitrobenzonitriles are fully effective in the presence of other additives normally employed in hydrocarbon fuels.
• the said additives include organo-metallic de- (mas aerugi'hosa; R-l, probably Penlclllium sp.; R-4, R6, yellow-green fungus, unidentified; R-7, probably Aspergillus sp.; C.r., Cladi'osporum rivatives such as organolead and organoaluminum compounds, ignition control compounds such as boron and phosphorus derivatives, deicing compositions, and the like.
• the compounds are employed for the control of bacteria and fungi by applying them to the locus of the microorganisms.
• the compounds are generally added in the form of a concentrate in a combustible solvent compatible with the hydrocarbon fuel in an amount such that the final concentration is between about p.p.m. and about 1000 ppm, preferably between about 10 ppm. and about 200 ppm.
• the low cost of the subject compounds renders use at these concentrations eminently practical.
• Example 1 Solutions of 2,5-dinitrobenzonitrile in JP4 jet fuel which have been sterilized 'by Seitz filtration are prepared providing concentrations between 62.5 and 1000 ppm. Three hundred milliliter portions of the solutions are placed over ml. of an aqueous base consisting of Bushnell-Haas medium a simple mineral salts medium which contains no source of carbon. The fuel-medium mixtures are placed in 250 ml. of flasks which are sterilized prior to use. Each of the flasks containing the fuel-water mixture is inoculated with 0.3 ml. of an inoculum containing 675x10 organisms per ml.
• Example 2 The general procedure of Example l is followed except that concentrations of 125, 250, 500 and 1000 ppm. of 2,4-dinitrobenzonitrile are employed.
• the additive is provided by adding to the fuel mixture a suitable quantity of a concentrate comprising a 10 percent solution of 2,4-dinitrobenzonitrile in methyl Cellosolve to which a small quantity of glycerine has been added.
• a suitable quantity of a concentrate comprising a 10 percent solution of 2,4-dinitrobenzonitrile in methyl Cellosolve to which a small quantity of glycerine has been added.
• actual plate counts are done in order to determine the number of organisms present in the aqueous phase at various time intervals.
• the mixed inoculum again contains 675 10 organisms per ml.
• Example 3 The procedure of Example 2 is repeated using Z-nitrobenzonitrile as the additive. All flasks containing 250 p.p.m. or more of the additive are entirely free of bacterial or fungal contamination at each observation. The control flasks contain organisms as indicated in Example 2.
• Example 4 The procedure of Example 2 is repeated with identical results using 3,4-dinitrobenzonitrile.
• the additive is provided as a concentrate in benzene solution.
• a hydrocarbon fuel composition comprising essentially a major portion of a hydrocarbon fuel and an inhibitory concentration of .an antimicrobial compound selected from the group consisting of 2-nitrobenzonitrile. 2,4-dinitrobenzonitrile, 2-nitroterephthalonitrile, 3-nitrophthalonitrile, and 4-nitrophthalonitrile.
• composition of claim 1 in which the antimicrobial compound is 2-nitrobenz-onitrile.
• composition of claim 1 in which the antimicrobial compound is 2,4-dinitrobenzonitrile.
• composition of claim 1 in which the antimicrobial compound is 2-nitroterephthalonitrile.
• a composition for the prevention of fouling of hydrocarbon fuels which comprises a concentrate of an antimicrobial compound selected from the group consisting of Z-nitrobenzonitrile, 2,4-dinitrobenzonitrile, 2-nitroterephthalonitrile, 3-nitrophthalonitrile, and 4-nitrophthalonitrile in a combustible solvent which is compatible with the hydrocarbon fuel.
• composition of claim 6 in which the antimicrobial compound is 2,4-dinitrobenzonitrile.

Landscapes

• Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Liquid Carbonaceous Fuels (AREA)

Priority Applications (9)

Applications Claiming Priority (1)

Publications (1)

Family

ID=23161178

Family Applications (1)

Country Status (8)

Cited By (1)

Families Citing this family (1)

Citations (2)

Family Cites Families (1)

• 0
  • GB GB1051055D patent/GB1051055A/en active Active
• 1963
  • 1963-08-08 US US300923A patent/US3353939A/en not_active Expired - Lifetime
• 1964
  • 1964-08-03 ES ES0302764A patent/ES302764A1/es not_active Expired
  • 1964-08-03 DE DEE27535A patent/DE1203424B/de active Pending
  • 1964-08-06 NL NL6409010A patent/NL6409010A/xx unknown
  • 1964-08-07 BE BE651579A patent/BE651579A/xx unknown
  • 1964-08-07 DK DK392764AA patent/DK111256B/da unknown
  • 1964-08-07 CH CH1038964A patent/CH478908A/de not_active IP Right Cessation

Patent Citations (2)

Also Published As

Similar Documents