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
  • C10L1/16—Hydrocarbons
  • C10L1/1608—Well defined compounds, e.g. hexane, benzene
• • 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
  • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
• • 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
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
  • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
• • 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
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
  • C10L1/1857—Aldehydes; Ketones
• • 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
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
• • 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
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
  • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols

Definitions

• the present invention relates to a liquid hydrocarbon composition, intended in particular for use as fuel or fuel in engines and thermal machines. More specifically, the present invention relates to a composition of liquid hydrocarbons, the odor of which is improved thanks to the use of an original additive, the family of tricyclodecanes and / or tricyclodecènes. The present invention also relates to the use of such additive to improve the smell of fuels and / or to fight against bacterial proliferation in these.
• the hydrocarbon compositions, in particular fuels have a characteristic odor, particularly unpleasant for the user. This is why formulators of this type of product now seeks to mask the unpleasant odor, even even give them a pleasant smell by the use of specific additives called also additives or odor masks.
• patent application WO 91/18961 describes the use, to mask or reduce the odor of a fuel or fuel of petroleum origin, of at least one carboxylic acid ester and alcohol.
• This ester has at most 25 carbon atoms carbon, and preferably from 4 to 14 carbon atoms. It is advantageous used with a perfume composition comprising selected compounds among aldehydes, ketones, alcohols, other esters, terpenes, with which he would act synergistically.
• compositions have also been developed for the purpose of hide not so much the smell of the fuel itself, but the smell of gas of exhausts emitted during the combustion of the latter.
• US Patent 1,348,512 describes an agent masking the smells of exhaust gases and fumes from combustion of middle distillates, such as, in particular, diesel fuels or lamp oils.
• This agent incorporated into the distillate, consists of a mixture of vanillin with xylene musk.
• the agent also includes distillation residues of oxo alcohols and / or an ester, an alcohol, a ketone, an aldehyde having from 10 to 20 carbon atoms or a mixture of such compounds.
• US Patent 3,151,956 recommends incorporating diesel fuels an odor mask comprising benzyl salicylate, preferably in combination with oxo-synthesis derivatives and / or vanillin, synthetic musks (based on ter-butyl-nitro-benzenes), diethyl phthalate, the ionone, eugenol.
• application WO 01/74141 recommends, in order to reduce the unpleasant odor of these products, to employ a thiazole of formula R- (S) n -TZ- (S) n -R, TZ representing a thiazole ring, in combination with an odor mask consisting of conventional odor compounds including aromatic esters.
• thiazoles can not be used in fuels, on the one hand because they have different odors from those of lubricants, and on the other hand because of the fact that these compounds provide significant quantities of fuels. nitrogen and sulfur, which goes against the current environmental constraints that require on the contrary to reduce the nitrogen and sulfur content of fuels.
• compositions described in the prior art have an effectiveness limited.
• hydrocarbon fuels and fuels very specific olfactory profiles, which may vary according to the types of cuts used (light or heavy) and according to the origin of these cuts. It proves thus particularly difficult to develop an additive or a composition resorption additives that significantly improve the odor of hydrocarbon cuts usually constituting fuels, whatever their nature and origin.
• the present invention aims at providing a hydrocarbon composition, useful in particular as fuel or fuel, which has an olfactory profile particularly balanced with respect to the compositions known in the prior art.
• the present invention relates to a hydrocarbon composition
• a hydrocarbon composition comprising a major proportion of at least one liquid hydrocarbon fraction, characterized in that it comprises from 1 to 2000 ppm by weight of at least one additive of formula (I) below: wherein the cyclopentane ring is saturated or unsaturated, and R1, R2, R3, which may be identical or different, are chosen from hydrogen and hydrocarbon radicals comprising from 1 to 10 carbon atoms and optionally containing one or more heteroatoms, in particular from 1 to 3 heteroatoms.
• the hydrocarbon radicals can be linear or branched.
• heteroatom oxygen atoms, nitrogen and sulfur.
• the additives of formula (I) above have the advantage of masking very appreciable way the smell of fuels and fuels based of hydrocarbons, and even to impart a relatively pleasant odor to the latter.
• these additives additionally have the unexpected advantage of strengthening, in the matrices very particulars are the hydrocarbon mixtures, the olfactory intensity of the others additive additives, if added, so that the notes of these come out with more intensity than if they were used in the absence of the additive of formula (I). There is thus a synergistic effect between the additive according to the invention and the deodorant additives traditionally used in fuels.
• the additive of formula (I) has also been unexpectedly substantially reduce the proliferation of bacteria and fungi which usually tend to develop in compositions hydrocarbons, especially when they are contaminated with water. They are revealed indeed to have an excellent effect both bactericidal and fungicidal, and can be used for these purposes both curative and preventive.
• the invention can not be limited to any specific isomer, each particular isomer which can be used as an additive according to the invention, alone or in mixture with one or more other isomers. Often, these compounds are present as a mixture of some isomers, one of which is majority, and it may be more advantageous to use such a mixture of isomers than to seek, at the cost of expensive separation steps, to isolate the desired isomer.
• a preferred isomer (generally available in the form of a mixture with other isomers present in a smaller amount) is the one whose configuration is as follows:
• R3 is selected from hydrogen and alkylcarboxylate radicals of formula R'-COO with R 'linear or branched C1-C4 alkyl radical.
• R 1 or R 2 is hydrogen.
• R3 is hydrogen.
• R 1 is chosen from the alkylcarboxylate radicals of R'-COO formula with R 'C1-C4 alkyl radical, linear or branched.
• the concentration of the additive of formula (I) in the composition of hydrocarbons is between 1 and 1000 ppm by weight, preferably between 1 and 200 ppm mass.
• the additive of formula (I) is advantageously employed in the composition of hydrocarbons according to the invention, in combination with at least one other additive it will bring out the particular notes.
• the additive of formula (I) can so be used with all the compounds used in known manner to improve the smell of fuels. It is thus possible to prepare fuels with a wide range of olfactory profiles and relatively subtle.
• the ratio by weight additive (I): other additive reodorant is variable in a wide measurement, from 100: 0 (no other additive) to 1:99, especially between 99: 1 to 1:99, example 90:10 to 10:90.
• the additive of formula (I) according to the invention can thus be integrated with a perfume composition for fuels and which composition comprises this additive in admixture with other additive additives.
• At least one petrol cut, a distillate cut or a cut essentially paraffinic such as kerdane or a mixture of such cuts is preferable to use.
• biofuel is meant light alcohols such as methanol, ethanol and corresponding ethers, oils of vegetable and / or animal origin and esters of such oils.
• the hydrocarbon composition according to the invention can thus be advantageously contain from 0.1 to 60% by weight, and preferably from 0.5 to 50% mass of biofuel.
• Preferred biofuels are esters of alcohols containing 1 to 4 carbon atoms and fatty acids or mixtures of acids fat containing from 16 to 22 carbon atoms.
• Biofuels particularly preferred are the methyl esters of vegetable oils such as for example, but without limitation, soybean, rapeseed, sunflower, olive and palm oils.
• the hydrocarbon composition according to the invention comprises at least one distillate cut.
• the composition of hydrocarbons according to the invention is a diesel fuel, that is to say a hydrocarbon composition meeting the requirements of the NF EN 590 standard.
• its fraction distilled according to EN ISO 3405 is less than 65% volume at 250 ° C and greater than 95% volume at 370 ° C
• its sulfur content according to EN 590 is less than or equal to 350 ppm mass, preferably less than or equal to 50 ppm mass, even more preferably less than or equal to 10 ppm mass.
• Its content polycyclic aromatic hydrocarbons, determined according to the IP 391 standard is preferably less than or equal to 11% by weight.
• the hydrocarbon composition according to the invention is a domestic fuel oil, for example as defined in the CSR 441 specifications (dated July 1, 2002) of Union Chamber refining Oil (Paris).
• its fraction distilled according to standard NF EN ISO 3405 is less than 65% volume at 250 ° C and greater than 85% volume at 350 ° C
• its content in sulfur according to standard NF EN ISO 14596 is less than or equal to 2000 ppm mass, preferably less than or equal to 1000 ppm mass.
• the hydrocarbon composition according to the invention can be prepared from very simple way, by incorporating with hydrocarbons (by simple mixing physical) the additive according to the invention, alone or in mixture with the other additives.
• the invention therefore also comprises a process for preparing a composition hydrocarbons having an improved odor, including mixing all or part of the hydrocarbons with at least one additive of formula (I) as described above.
• the additive of formula (I) When the additive of formula (I) is used in combination with other additives (such as those mentioned above), it is preferable incorporated into the hydrocarbon composition as a composition fragrant.
• This perfume composition is advantageously in the form a liquid comprising the additive of formula (I) mixed with the other additives deodorants and optionally an organic solvent.
• Such a perfume composition advantageously contains from 2 to 50% by mass (solvent not included) of additive (s) of formula (I).
• the composition of hydrocarbons advantageously comprises from 1 to 5000 ppm by weight, preferably from 5 to 1000 ppm mass of perfume composition.
• the compound of formula (I), alone or in the form of a perfume composition as described above, is initially mixed with all or part of the other additives that must contain the hydrocarbon composition, thus forming an additive composition which is generally called in the profession "additive package”. Then, in a second step, this additive composition is incorporated by simple mixing in the hydrocarbon composition.
• This solution has the advantage of being able to formulate ready-to-use additive compositions that can be routed on the different places of preparation of fuels and / or fuels. It is It is also possible to store or even market such compositions additives.
• Such a composition may also contain other additives, such as inter alia one or more lubricant additives, one or more additives anticorrosion, one or more anti-foam additives. It can be diluted in a suitable organic solvent.
• the diesel fuel preferably contains from 250 to 5000 ppm volume of a such additive composition.
• Such a composition may also contain one or more other additives, for example biocidal additives. It can be diluted in a solvent appropriate organic.
• Domestic fuel oil preferably contains 500 to 5000 ppm volume such an additive composition.
• the present invention also relates to the use of a compound of formula (I), for improving the odor of hydrocarbon compositions, in particular petrol fuels, diesel fuels and domestic fuel oils.
• the invention includes a method for improving the odor of hydrocarbon compositions such as, in particular, petrol fuels, diesel fuels and domestic fuel oils, including the addition to all or part of hydrocarbons of at least one additive of formula (I) as described above, alone or mixed with other additives, such as, for example, conventional odor compounds as mentioned above.
• the present invention finally relates to the use of a compound of formula (I) as a bactericidal agent in hydrocarbon compositions, such as including gasoline fuels, diesel fuels and fuel oil servants. It also relates to the use of a compound of formula (I) as a fungicidal agent in such hydrocarbon compositions.
• the invention includes a method for eliminating bacteria and / or fungi in hydrocarbon compositions or prevent their appearance in such compositions, this method comprising adding to all or part of the hydrocarbons of at least one compound of formula (I) as described above.
• This example illustrates the effect of an additive A according to the invention on the odor of a conventional hydrocarbon composition.
• Additive A used is 3a, 4,5,6,7,7a-hexahydro-4,7-methanoinden-6-yl acetate (also called verdyl acetate). This compound is generally in admixture with its isomer, 3a, 4,5,6,7,7a-hexahydro-4,7-methanoinden-5-yl acetate.
• N be the number of times or the sample is preferred.
• p 1/2 the number of critical responses Nc corresponding to the chosen confidence level. If N> Nc, the solution is indeed preferred to the chosen confidence level. Otherwise the gap to the expectation can be put on the effect of chance and it can not be said that the solution is preferred.
• Nc 44 for a confidence level of 0.1%.
• This example illustrates the effect on the odor of a hydrocarbon composition conventional, an additive A according to the invention integrated in a perfume composition.
• the additive A used is identical to that of example 1.
• the composition of perfume consists of a perfume base B of the type used typically in fuels.
• This base B includes the following compounds (which are standard components of gas oils, known to those skilled in the art): isoamyl acetate, vanillin, anthranylate methyl, ethyl butyrate, raspberry ketone, C14 aldehyde.
• the total contents of the additive additives of the two compositions 1 and 2 are therefore identical (70 ppm).
• the incorporation of the additive A according to the invention therefore significantly improves the efficiency of the conventional deodorant additives. This underlines the importance of the use of additive A within a scented composition for fuels or fuel-based hydrocarbons.
• This example illustrates the bactericidal effect of an additive A according to the invention on a conventional hydrocarbon composition.
• the additive A used is identical to that of example 1.
• the strain of bacteria used is Pseudomonas aeruginosa (ATCC33988). The day before inoculation, this The bacterium is cultured in a liquid medium, with an incubation time of 16 hours at 37 ° C.
• Two hydrocarbon compositions are prepared as follows: two samples of 300 g of cut C are taken and placed in flasks of 1000 ml in brown glass. Additive A is added with the following concentrations: 0 (control, according to the prior art), 107 ppm (according to the invention). The bottles are closed in a non-hermetic manner. The contents of each bottle are stirred using a magnetic bar at room temperature.
• the inoculation of the two samples is carried out at t o in the following manner: the initial culture (concentration of which is 10 9 cfu / ml) is diluted 1/10 in physiological saline.
• the physiological saline used is prepared by dissolving 8 g of NaCl in 1000 ml of distilled water). 15 ml of the suspension thus diluted in the two hydrocarbon samples are added.
• cfu means "colony forming unit": 1 cfu corresponds to 1 cultivable cell.
• a sample is taken in each vial: 0.2 ml of aqueous phase is taken from each vial (after stopping the stirring and decantation), which is replaced by the same volume of physiological saline.
• 50 .mu.l are added to a tube containing 5 ml of Tryptone-salt (10 -2 dilution).
• the Tryptone-salt solution used in Examples 3 and 4 is prepared by dissolving 1 g of tryptone and 8.5 g of NaCl in 1000 ml of distilled water.
• cascade dilutions up to 10 -4 (10 -6 for the control) are carried out with physiological saline.
• PCA agar medium For counting the bacteria, 100 ⁇ l of each dilution PCA agar medium ("flat count agar").
• PCA agar is prepared by mixing 2.5 g of yeast extract, 5 g of tryptone, 1 g of glucose, 15 g of agar and 1000 ml distilled water.
• the initial concentration at t o in each vial is 2.9 ⁇ 10 8 cfu / ml.
• the concentration of bacteria after 24 hours is 10 3 cfu / ml.
• the concentration of bacteria after 24 hours is less than 10 cfu / ml, that is to say almost zero.
• This example illustrates the fungicidal effect of an additive A according to the invention on a conventional hydrocarbon composition.
• the additive A used is identical to that of Example 1.
• the mold strain used is Hormoconis resinae (ATCC20495). The day before inoculation, this mold is grown on a petri dish, with a 24 hour incubation time at 30 ° C.
• the inoculation of the two samples is carried out at t o in the following manner: 5 ml of physiological saline are introduced into the Petri dish containing the colonies, and lightly rubbed in order to detach the spores. An enumeration is then carried out under a microscope using a Malassez cell. The concentration is 2.2.10 7 spores / ml. After appropriate dilution of this suspension in the two hydrocarbon samples, the concentration obtained in each vial at t o is 5.10 3 cfu / ml.
• Samples are taken from each of the two vials at regular time intervals (at t o , t o + 24 h, t o + 48 h, t o + 72 h, t o + 7 days).
• 0.2 ml of aqueous phase is taken from each vial (after stopping the stirring and decantation) which is replaced by the same volume of physiological saline.
• 50 .mu.l are added to a tube containing 5 ml of Tryptone-salt (10 -2 dilution). After homogenization, cascade dilutions up to 10 -4 (10 -6 for the control) are carried out with physiological saline.
• the boxes are left overnight cover up to impregnate well the medium and then incubated for 3 days at 30 ° C.
• the count of molds is done according to ASTM E1259-94.

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• 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)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Liquid Carbonaceous Fuels (AREA)
• Lubricants (AREA)
• Disinfection, Sterilisation Or Deodorisation Of Air (AREA)

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• 2004
  • 2004-04-30 FR FR0404654A patent/FR2869621B1/fr not_active Expired - Fee Related
• 2005
  • 2005-04-26 PL PL05290917T patent/PL1591514T3/pl unknown
  • 2005-04-26 EP EP05290917.3A patent/EP1591514B1/de active Active

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