EP1884555A2 - Masquage d'odeurs d'huiles minérales et embaumement d'huiles minérales - Google Patents

Masquage d'odeurs d'huiles minérales et embaumement d'huiles minérales Download PDF

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Publication number
EP1884555A2
EP1884555A2 EP07113304A EP07113304A EP1884555A2 EP 1884555 A2 EP1884555 A2 EP 1884555A2 EP 07113304 A EP07113304 A EP 07113304A EP 07113304 A EP07113304 A EP 07113304A EP 1884555 A2 EP1884555 A2 EP 1884555A2
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European Patent Office
Prior art keywords
methyl
dimethyl
trimethyl
mineral oil
group
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EP07113304A
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German (de)
English (en)
Inventor
Anja Finke
Jörg Eilers
Falk Harzke
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Symrise AG
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Symrise AG
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Publication of EP1884555A2 publication Critical patent/EP1884555A2/fr
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/38—Heterocyclic nitrogen compounds
    • C10M133/40—Six-membered ring containing nitrogen and carbon only
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
    • C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
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    • 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
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/04—Well-defined cycloaliphatic compounds
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    • C10M2203/06—Well-defined aromatic compounds
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/044—Cyclic ethers having four or more ring atoms, e.g. furans, dioxolanes
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/08—Aldehydes; Ketones
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/122—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C10M2207/128—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids containing hydroxy groups; Ethers thereof
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/284—Esters of aromatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/16—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/34—Fragrance or deodorizing properties

Definitions

  • the invention relates to the field of masking mineral oil odor and the scenting of mineral oils.
  • the invention relates to a selection of particularly suitable fragrances for masking a mineral oil odor and the scenting of mineral oils.
  • the invention relates to additives and corresponding scented mineral oils themselves, in particular fuels and heating or lubricating oils.
  • mineral oils are the so-called middle distillates which have a boiling range of from 180 to 360 ° C. under normal pressure (1013 mbar), in particular fuel oil EL according to DIN 51603 and diesel fuel according to DIN EN 590, fuel oil according to DIN 51601 part 1.
  • mineral oil fraction Boiling range (at 1013 mbar) use LPG below 30 ° C Heating gas for industry and household petroleum ether 40 - 70 ° C Petrol, solvent benzine 60 - 100 ° C Production of benzene, production of gases by cracking, solvents means petrol 70 - 150 ° C Carburetor fuel (gasoline) solvent naphtha 120 - 180 ° C Fuel for jet aircraft, solvent Kerosene (petroleum) 150-280 ° C Jet fuel petrol solvent, light fuel oil gas oil 200 - 360 ° C Diesel fuel, heating oil Residue over 360 ° C By vacuum distillation: Production of motor oil, heavy fuel oil Rest: bitumen ("tar”)
  • Mineral oil odor is understood to mean the odor which emanates from higher-boiling, unperfumed mineral-oil fractions such as fuel oil, diesel, gasoline, aviation gasoline, lubricating oil for engines or chains or cutting oil.
  • This smell of mineral oil fractions (mineral oil odor), which is perceived as unpleasant by humans, is also referred to below as a bad smell or malodor.
  • the masking, reducing or covering the mineral oil malodors has been found to be particularly difficult if the mineral oil is a heating oil, in particular a heating oil EL according to DIN 51603, a heating oil according to DIN 51601 part 1 and a diesel fuel according to DIN EN 590, so a share of at least 90% by weight and in particular of 95-99.9% by weight, based on the total mineral oil, of a heating oil EL according to DIN 51603, a heating oil according to DIN 51601 part 1 and / or a diesel fuel according to DIN EN 590.
  • Scenting or perfuming is understood to mean the imparting of an odor impression, here of mineral oils, i. an additional odor effect over the total or partial coverage of the odor of mineral oil fractions; the fragrance goes beyond mere masking.
  • a perfume is in the broader sense any substance that evokes an odor impression or changes the smell perception of another substance.
  • a fragrance is a substance that causes an odor impression (in humans).
  • a fragrance mixture according to the invention is a mixture containing two or more fragrances in the narrower or broader sense.
  • Additives are additives, active ingredients or mixtures of active ingredients which enhance desired properties in fuels, fuels and lubricants, suppress undesirable properties or exert new effects.
  • the engine intake system can be kept clean and deposits in the engine can be prevented, or the resistance to aging can be extended in lubricating oils.
  • Lowering pollutant emissions in the exhaust and preventing corrosion of metal parts in the fuel system are other desirable effects of additives.
  • Essential mineral oils according to the invention essentially contain no substances with a boiling point of less than 120 ° C. at 1013 mbar. Preference is given to mineral oils in which at least 90% by weight, particularly preferably at least 95% by weight, of the compounds contained therein have a boiling point in the range from 180 ° to 380 ° C. at 1013 mbar. Particularly preferred mineral oils are heating oil and diesel, in particular as indicated above.
  • Mineral oils preferred according to the invention have a water content of at most 1% by weight, preferably of at most 0.5% by weight.
  • the sulfur content in mineral oils according to the invention is preferably at most 500 mg / kg, preferably at most 200 mg / kg.
  • the proportion of mineral oil fractions according to the above table, in particular heavy fuel, kerosene and gas oil, to a mineral oil according to the invention is at least 90 wt .-%, particularly preferably 95 to 99.9% by weight, each based on the total mineral oil.
  • the fragrances or perfume mixtures should give the mineral oil fractions a pleasant odor or at least mask the malodor of the mineral oil fractions, a warning smell should not be imparted.
  • the relevant in the context of the present invention mineral oil fractions are fundamentally different from the essentially odorless fuels such as methane or LPG by their characteristic odor.
  • the mineral oil fractions which are relevant in the context of the present invention differ in their boiling point range or state of aggregation from the abovementioned fuels, so that the physicochemical interactions between the mineral oil fractions considered here and the fragrances or perfume mixtures incorporated therein and their release from the respective mineral oil fraction or whose masking properties are different with respect to the odor of the mineral oil fraction than with the abovementioned fuels.
  • odorants ie substances which should give the fuel gas a warning smell and no pleasant smell
  • the amount of odorant is 50 ppm by weight (mg / kg gas), preferably greater than or equal to 100 ppm.
  • the best results in LPG were obtained with mixtures comprising tert-butylmercaptan.
  • JP 59-185813 deals with the odor overlap of exhaust gases of a two-stroke engine.
  • the solution shown there provides that the provided with an aromatic perfume lubricating oil is fed via a pump in the combustible fuel-air - mixture and the resulting mixture is introduced into the cylinder, wherein the provided with an aromatic perfume lubricating oil only partially burns. By remaining in the exhaust gas residual amount of perfume then the exhaust odor should be covered.
  • Usual perfumes for use in cosmetic products, etc. are considered suitable, the amount of perfume used is about 1 wt .-%, based on the mass of the lubricating oil.
  • CN 1 049 176 describes the scenting of fuels such as LPG (Liquefied Petroleum Gas), gasoline and diesel by adding essences such as orange oil or jasmine oil, so that sweet smelling fuels are obtained.
  • the proportion of essences is in the range of 0.5 to 5 wt .-%, based on the total mass of the fuels.
  • JP 53-081634 is a mixture of odorous substances described, which causes petroleum-like solvents smell very unpleasant. This should prevent abuse of the same. These additives to unpleasant-smelling substances related to smell cause the opposite of what should be effected in the context of this invention.
  • EP 0 134 014 describes mineral oil compositions containing 2-70% terpenes, such as pinenes, cineole, limonene, dipentene, terpineols, menthol. Due to the high proportion of fragrances, the exhaust gases formed during the combustion of these mineral oil compositions should be given a more pleasant odor.
  • DE 1 037 668 describes kerosene containing steppe grass oil.
  • EP 1 591 514 describes hydrocarbon compositions containing tricyclododecanes or - dodecenes, such as cycloaddol acetate.
  • US 4,451,266 describes an additive for hydrocarbon mixtures such as gasoline or diesel, which in addition to an alcohol having at most four carbon atoms, an aromatic hydrocarbon, a halogenated alkene, a hydroxy acid and a hydrocarbon fraction of a certain boiling range also 5 to 15 wt.% Of an aliphatic ester comprising has at most 6 carbon atoms.
  • esters are there: methyl acetate, ethyl acetate, propyl acetate, tert-butyl acetate, methyl propionate, ethyl propionate, methyl n-butyrate, isopropyl acetate, methyl isobutyrate and mixtures thereof, with acetates, in particular propyl acetate, being preferred.
  • Extenders for hydrocarbon fuels which are heavier than gasoline (eg middle distillates), are used in US 4,353,710 described. Such Extenders are characterized by the presence of a methoxy or ethoxy group, especially from the class of ethers or esters. Representative examples of such extenders are methyl acetate, methyl propionate, methyl butyrate, ethyl acetate, ethyl propionate and ethyl butyrate. Typically, there is the proportion of said extenders 1 to 30 wt .-%, preferably 5 to 25 wt .-%, in particular by 20 wt .-%, based on the weight of the middle distillate.
  • the acid there comprises 1 to 4 C atoms, more preferably there are C 4 -C 10 esters of acetic acid, for example n-heptyl acetate or a 1: 1 mixture of n-hexyl acetate and n-octyl acetate.
  • reodorants may also contain aldehydes, ketones, alcohols, etc.
  • amyl acetate for the deodorization of hydrocarbons, especially of petroleum, is out GB 10,772 known. It is recommended that a dosage of 10 g of amyl acetate to 1 L petroleum.
  • Aerosol compositions which preferably contain 20-60% by weight of a low molecular weight ketone such as acetone and 20-60% by weight of petroleum ether having a boiling range of 30-40 ° C are disclosed in US Pat GB 1 385 199 described.
  • the aerosol compositions described therein preferably comprise, for the purpose of leak detection, a perfume which contains hexanoic acid allyl ester, ethylhexanoate, amyl acetate or furfurylmercaptan.
  • alkanecarboxylic acid alkyl esters such as amyl acetate (n-pentyl acetate), ethyl acetate, n-butyl acetate or n-heptyl acetate have no satisfactory masking effect on mineral oil odor (see also the results summarized in Table 2) fragrances not to be used according to the invention). Also, compounds such as hexanoic acid allyl ester, benzyl acetate and ethyl vanillin did not show a sufficient masking effect.
  • the stated object is achieved by a mineral oil, characterized in that the mineral oil has a proportion of 0.5 ppm to 1.2 wt .-%, based on the total mineral oil, on one or more fragrances which are selected from the group consisting of (A) number Surname 1 1,2,3,4,4a, 9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester; 7-Isopropyl-1,4a-dimethyl- 2 1,3,5-trioxane; 2,4,6-trimethyl 3 1,3-benzodioxolan-5-propanal; alpha-methyl 4 1,3-dioxane; 2,4,6-trimethyl-4-phenyl- 5 1,3-dioxolan-2-acetic acid ethyl ester; 2,4-dimethyl- 6 1,3-dioxolane 2-acetic acid ethyl ester; 2-methyl- 7 1,3-oxathiane
  • the fragrances or fragrance mixtures of group (A) to be used according to the invention are preferably formulated in an additive and added to a mineral oil fraction or a mixture of several mineral oil fractions to form a mineral oil according to the invention.
  • the fragrances of group (A) have a masking effect against unpleasant mineral oil odor and thus ensure a higher acceptance and nobler quality of these fragrances containing mineral oils.
  • the fragrances of group (A) have a masking effect against unpleasant mineral oil odor, in particular against the malodor of diesel and heating oil.
  • An additive contained in the mineral oil according to the invention in particular heating oil, diesel or gasoline, or usable for producing a mineral oil according to the invention preferably comprises, in addition to one or more fragrances of group (A) at least one, preferably 2, 3, 4, 5, 6, 7 or all the following ingredients: flow improver (WASA), lubricity improvers, antioxidants, ignition accelerators, anti-smoke, metal deactivators (chelating agents), stabilizers, detergents.
  • WASA flow improver
  • lubricity improvers lubricity improvers
  • antioxidants antioxidants
  • ignition accelerators antioxidants
  • anti-smoke anti-smoke
  • metal deactivators chelating agents
  • stabilizers detergents.
  • Solvents of the group L2 are e.g. under the name Shellsol D60 or Shellsol D100 (defined mixtures of n- and iso-paraffins in the range of 9 to 14 C-atoms) or Shellsol T (mixture of iso-paraffins) commercially available.
  • the concentration of fragrances of group (A) is preferably 1 to 1000 ppm in total, preferably 10 to 500 ppm and more preferably 30 to 300 ppm in heating oil, diesel and gasoline and 0.01 to 2% by weight, preferably 0.1 - 2 wt .-% and particularly preferably 0.2 - 2 wt .-% of lubricating oils.
  • mineral oils and additives having a number of at most 100 fragrances which furthermore preferably comprise at most 80 fragrances of group (A) to be used according to the invention or consist of fragrances of group (A).
  • Preferred mineral oils and additives comprise at most 60 fragrances, which further preferably at most 50 according to the invention odiferous substances of group (A) to be used or consist of odoriferous substances of group (A).
  • Particularly preferred mineral oils and additives comprise at most 30 fragrances which furthermore preferably comprise 3 to 30 fragrances of group (A) to be used according to the invention or consist of fragrances of group (A).
  • the fragrances of the following group (B) are particularly suitable for reducing, masking or suppressing the malodor of a mineral oil: number Surname 2 1,3,5-trioxane; 2,4,6-trimethyl 154 1,6-octadiene-3-ol; 3,7-dimethyl 9 1-Butanolacetat; 3-methyl 16 2 (3H) -furanone; 4-hydroxy-2,5-dimethyl- 152 2 (3H) -furanone; 5-butyl-tetrahydro- 19 2 (3H) -furanone; Dihydro-5-pentyl- 23 2,6-octadiene-1-ol; 3,7-dimethyl- (2E) 27 2,6-octadienal; 3,7-dimethyl- (2E) 150 2,6-octadienenitrile; 3,7-dimethyl- (2E) 149 2,6-octadienenitrile; 3,7-
  • fragrances group (B) have the strongest effect of reducing, masking or suppressing the mineral oil malodor. They are therefore preferred in used mineral oils of the invention, especially in diesel and fuel oil. Particularly preferably, a corresponding mineral oil contains two, three, four, five or more, preferably not more than 25, fragrances of group (B).
  • a mineral oil according to the invention which contains one or more fragrances of the group (A) of the fragrances of group (A): number Surname 4 1,3-dioxane; 2,4,6-trimethyl-4-phenyl- 5 1,3-dioxolan-2-acetic acid ethyl ester; 2,4-dimethyl- 7 1,3-oxathiane; 2-methyl-4-propyl- (Z) 13 1-nonyne; 1,1-dimethoxy- 14 1-octanol 18 2 (3H) -furanone; 5-hexyl-dihydro- 20 2,2-dimethylpropanal; 3- (4-ethylphenyl) - 21 2,4-decadienal (2E, 4E) 22 2,6-nonadienal (2E, 6Z) 26 2,6-octadiene-1-olformiat; 3,7-dimethyl- (2E) 29 2-butene-1-ol acetate; 3-methyl 31
  • fragrances of the group (C) in addition to a good Malodorreduktionswert (more below) also have a strong and pleasant odor, which can contribute to improving the acceptance of a mineral oil according to the invention. Accordingly, preferred is a corresponding mineral oil containing two, three, four, five or more, preferably not more than 25, fragrances of group (C).
  • a mineral oil according to the invention contains at least one, preferably two, three, four, five or more, and further preferably up to 25 fragrances of group (B) and at least one, preferably two, three, four, five or more and further preferably up to 25 fragrances of the group (C).
  • a mineral oil which in addition to the one or more fragrances of group (B) and / or (C) additionally contains one or more of the fragrances of the following group (D): number Surname 1 1,2,3,4,4a, 9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester; 7-Isopropyl-1,4a-dimethyl- 3 1,3-benzodioxolan-5-propanal; alpha-methyl 6 1,3-dioxolan-2-acetic acid ethyl ester; 2-methyl- 8th 10-undecenal 10 1-decanol 11 1H-4,7-methanoinden-5-olpropionat; 3a, 4,5,6,7,7a-hexahydro- 12 1-hexanol; 3,5,5-trimethyl 15 1-octen-3-ol acetate 17 2 (3H) -furanone; 5-heptyl-dihydro- 24 2,6-
  • the proportion of the total mass of fragrances of group (A) in additives of the invention from 0.5 to 80 wt .-%, preferably 2 to 50 wt .-%, preferably 3 to 30 wt .-%, each based on the total weight of the additive.
  • the number of the fragrances of the group (A), particularly the group (B), (C) and / or (D), in a mineral oil or additive of the invention is from 2 to 50, more preferably a number Fragrances of 3 to 30 to be used according to the invention, in each case based on the total mixture of the fragrances of group (A) in the mineral oil or additive.
  • fragrances of group (A), in particular of groups (B), (C) and / or (D) may additionally be present.
  • the total number of fragrances in a mineral oil according to the invention should not be more than 100.
  • fragrances in mineral oils according to the invention requires particularly effective fragrances and fragrance mixtures, therefore these should preferably be composed of a not too large number of particularly effective fragrances.
  • the possibility of discoloring an additive poses a difficulty. These discolorations can be triggered, for example, by an excessive concentration of vanillin, ethyl vanillin, maltol and / or ethyl maltol in the perfuming. Vanillin is effective against the unpleasant smell of mineral oil, but can lead to strong discoloration in the additive.
  • Vanillin, ethyl vanillin, maltol and / or ethyl maltol should only be present in minimal amounts in an additive for malodormask réelle, -erring réelle or -unterdschreibung or completely absent.
  • a mineral oil or additive according to the invention preferably comprises at least one, two or more, preferably no more than ten, other fragrances (which are therefore not part of the fragrances of group (A) to be used according to the invention) having a vapor pressure of greater than or equal to 0.1 Pa 25 ° C, preferably with a vapor pressure of greater than or equal to 0.5 Pa at 25 ° C, more preferably with a vapor pressure of greater than or equal to 1 Pa at 25 ° C.
  • fragrances which may be part of an additive according to the invention or of a mineral oil according to the invention can be found, for example, in US Pat S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, NJ, 1969 , Self-published or K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 4th. Ed., Wiley-VCH, Weinheim 2001 ,
  • the total proportion of essential oils in mineral oils and additives according to the invention is preferably at the highest 25 wt .-%, preferably at most 15 wt .-%, more preferably at most 7 wt .-%, based on the total amount of fragrances of group (A) in the mineral oil or additive.
  • additives according to the invention and mineral oil fractions are free of essential oils, especially since essential oils can partly lead to discoloration, separation and / or clouding in additives according to the invention and mineral oil fractions.
  • a mineral oil or additive according to the invention which comprises a total fraction of less than 8% by weight of vanillin, ethylvanillin, maltol and / or ethylmaltol, based on the total mass of the fragrances of group (A), is advantageous.
  • an inventive mineral oil or additive with a proportion of less than 8 wt .-% of vanillin based on the total amount of fragrances of group (A).
  • a mineral oil and additive according to the invention which has a proportion of less than 4% by weight and more preferably less than 1.5% by weight of vanillin, based on the total amount of fragrances of group (A) in the mineral oil or Additive includes.
  • a product By using mixtures of the specified fragrances of group (A) and especially groups (B) and (C), a product can be perfumed so that a faint fragrance is perceived, but at the same time the presence of the unpleasant odor of mineral oil fractions is suppressed , Strong high intensity perfuming is not necessary to achieve the desired effect.
  • fragrance masking odor odor or a fragrance mixture is currently consuming.
  • the intensity of a substance or substance mixture describes the intensity of the mixture perceived by trained examiners as odorless or odor, regardless of the quality of the odor.
  • the intensity is rated here on a scale of 1 to 9.
  • the value 1 means odorless, 9 means very strong smelling.
  • the malodorous impression in turn describes the intensity of the perceived bad smell.
  • the term malodor reduction value in the present case describes the intensity difference, i. the difference, bad odor (malodor) of the malodor standard mixture and the test mixture.
  • the test method is carried out at 20 ° C and 1013 mbar. It is likewise preferred if the concentration of heating oil in the malodor standard mixture and the test mixture is the same. This allows a particularly good comparison of the mixtures.
  • the test sample according to the invention preferably comprises one or more fragrances.
  • more complex fragrance mixtures such as chords of fragrances and essential oils can be checked for their suitability for masking mineral oil odor.
  • a defined amount of a mineral oil fraction is preferably used.
  • the concentration of the malodor standard heating oil in the test and / or malodor standard mixture is at least 0.1 ⁇ l / l, preferably 0.1 to 1 ⁇ l / l and particularly preferably 0.3 to 0.8 ⁇ l / l.
  • concentrations the Bad odor of Malodor standards already clearly perceptible, but without the olfactory sense of an examiner is largely blocked by the malodor standard. This concentration does not affect the cognitive ability or well-being of the examiners even if many (10-30) samples are evaluated promptly.
  • concentrations can be adjusted particularly easily by evaporating 5 .mu.l of the mineral oil fraction to be investigated in 7 l of air.
  • the test method is particularly preferably carried out by testing the individual test samples in the suitability for covering the mineral oil odor in vessels of the same size.
  • the individual samples are evaluated in each case by at least 8 examiners (experts) by smelling compared to a sample only with the mineral oil fraction (malodor standard). This malodor standard without fragrance gets the intensity 6 specified.
  • the evaluation of the odor intensities is carried out on a scale from 1 according to "odorless” to 9 corresponding to "very strong”.
  • the reduction value is calculated by subtracting the intensity of the standard from the mean odor intensity of the malodor.
  • the examiners are chosen for their ability to reproducibly evaluate the strengths of odors.
  • the examiners are trained before the test series on the recognition of mineral oil odor.
  • the fragrance to be tested or the fragrance mixture to be tested is incorporated in a concentration of 50 ppm in the relevant mineral oil fraction.
  • fragrances or perfume mixtures to be used according to the invention and the test sample containing one or more fragrances according to the invention can be combined with perfume oils in particularly preferred embodiments of the invention.
  • a mineral oil odor masking additive is specified, prepared by a production process according to the invention.
  • Fragrances of group (A) to be used according to the invention or a fragrance mixture to be used according to the invention comprising 2, 3, 4, 5, 6, 7, 8, 9, 10 or more fragrances of group (A) have a malodor reduction value of greater than or equal to 2.3 on.
  • Preferred fragrances of group (A) to be used according to the invention or a fragrance mixture to be used according to the invention comprising 2, 3, 4, 5, 6, 7, 8, 9, 10 or more fragrances of group (A) have a Malodorreduktionswert of greater or equal 3.0, more preferably a malodor reduction value of greater than or equal to 3.5.
  • the fragrances investigated are individual fragrances (in individual cases, these may also be mixtures of (E) and (Z) isomers or of stereoisomers).
  • the fragrances are evaluated by the selected examiners in a defined gaseous sample with regard to intensity and residual odor strength of the diesel or heating oil.
  • fragrances are equally soluble in mineral oil fractions. Therefore, 30 ⁇ l fragrance and 150 ⁇ l each of the diesel or fuel oil are mixed for sample preparation. From the oil phase, place 6 ⁇ l in an air-filled 7 l volume container. The samples are held at room temperature (about 20 ° C) for 15 hours prior to evaluation. The individual samples are each smelled by at least 8 examiners compared to a sample containing only 5 ⁇ l of diesel or fuel oil. From the obtained at least 8 values for the respective raw material then the mean value is formed.
  • Example 2 Test of mixtures / chords against fuel oil odor
  • the mixtures AC were compared to 4.4a.5.9b-tetrahydro-indeno [1.2-d] -1,3-dioxin, 1-methyl-4- (1-methylethenyl) -cyclohexene and 2- (2-ethoxyethoxy) -ethanol after the above method tested.
  • the mixtures have the desired effect.
  • the values of the individual substances could be repeated.
  • the mixtures AC were also compared to 4.4a.5.9b-tetrahydro-indeno [1,2-d] -1,3-dioxin, 1-methyl-4- (1-methylethenyl) -cyclohexene and 2- (2-ethoxyethoxy) -ethanol tested in a dosage of 50 ppm in heating oil.
  • the perfumes were stirred in this dosage in fuel oil.
  • 10 g of the perfumed fuel oil were filled in 30 ml screw jars.
  • the samples were evaluated on the same scale as unperfumed fuel oil, as in the above procedure.
  • the mixtures also have the desired effect in this test, closer to the actual use of the products.

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  • Engineering & Computer Science (AREA)
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EP07113304A 2006-08-01 2007-07-27 Masquage d'odeurs d'huiles minérales et embaumement d'huiles minérales Withdrawn EP1884555A2 (fr)

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EP2119925A1 (fr) * 2008-05-13 2009-11-18 Siemens Aktiengesellschaft Lubrifiant doté d'un additif volatile pour la lubrification de machines à grande vitesse
WO2012080235A1 (fr) * 2010-12-13 2012-06-21 Givaudan Sa Compositions de lutte contre les mauvaises odeurs
WO2013077738A1 (fr) * 2011-11-25 2013-05-30 Progression-Industry B.V. Procédé de préparation d'un combustible par l'ajout d'un ou de plusieurs composants à un combustible de base
CN108587709A (zh) * 2018-05-18 2018-09-28 萧县沃德化工科技有限公司 2-萘酚废母液和反应残余物制备水煤浆添加剂的方法
EP3922707A1 (fr) 2020-06-10 2021-12-15 Brauns-Heitmann GmbH & Co. KG Réduction des mauvaises odeurs dans le bioéthanol
EP4183462A1 (fr) 2021-11-23 2023-05-24 TotalEnergies OneTech Procédé de désodorisation d'huiles lubrifiantes régénérées utilisant du co2 supercritique

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FR2942804B1 (fr) * 2009-03-09 2011-08-19 Arkema France Carburant aviation contenant une proportion de composes organiques ex-biomasse
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JP5593271B2 (ja) 2011-06-06 2014-09-17 花王株式会社 悪臭抑制剤の探索方法
NL2007304C2 (en) 2011-08-26 2013-02-27 Progression Industry B V Use of perfume composition as fuel for internal combustion engines.
TW201328010A (zh) * 2011-12-16 2013-07-01 Univ Nat Cheng Kung 用於熱光電系統之燃燒裝置
US20130210775A1 (en) * 2012-02-09 2013-08-15 Kao Corporation Agent for inhibiting odor of pyrazine derivatives
US9057090B2 (en) 2012-02-09 2015-06-16 Kao Corporation Method of identifying an agent for inhibiting odor of pyrazine derivatives
WO2015048163A1 (fr) * 2013-09-25 2015-04-02 Takasago International Corp. (Usa) (6z)-non-6-ènenitrile utilisé en tant que matière de parfum et d'arôme
US10294193B2 (en) 2014-06-04 2019-05-21 Takasago International Corporation Compound, and flavor composition and/or fragrance composition containing same
EP3174561A4 (fr) 2014-07-30 2019-07-24 GPCP IP Holdings LLC Distributeurs d'assainisseur d'air, cartouches, systèmes et procédés associés
WO2016188830A1 (fr) 2015-05-22 2016-12-01 Akzo Nobel Chemicals International B.V. Solvants à base de nitriles gras pour formulations agricoles
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JP6867622B2 (ja) * 2016-07-29 2021-04-28 山本香料株式会社 臭気変調用油剤及び潤滑油
JP6853524B2 (ja) * 2016-07-29 2021-03-31 山本香料株式会社 臭気変調方法
WO2019201630A1 (fr) * 2018-04-20 2019-10-24 Shell Internationale Research Maatschappij B.V. Carburant diesel présentant des caractéristiques d'allumage améliorées
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EP2119925A1 (fr) * 2008-05-13 2009-11-18 Siemens Aktiengesellschaft Lubrifiant doté d'un additif volatile pour la lubrification de machines à grande vitesse
WO2012080235A1 (fr) * 2010-12-13 2012-06-21 Givaudan Sa Compositions de lutte contre les mauvaises odeurs
US9125828B2 (en) 2010-12-13 2015-09-08 Givaudan Sa MOC compositions
WO2013077738A1 (fr) * 2011-11-25 2013-05-30 Progression-Industry B.V. Procédé de préparation d'un combustible par l'ajout d'un ou de plusieurs composants à un combustible de base
CN108587709A (zh) * 2018-05-18 2018-09-28 萧县沃德化工科技有限公司 2-萘酚废母液和反应残余物制备水煤浆添加剂的方法
EP3922707A1 (fr) 2020-06-10 2021-12-15 Brauns-Heitmann GmbH & Co. KG Réduction des mauvaises odeurs dans le bioéthanol
DE102020115468A1 (de) 2020-06-10 2021-12-16 Brauns-Heitmann GmbH & Co Kommanditgesellschaft Minderung von Fehlgerüchen in Bioethanol
EP4183462A1 (fr) 2021-11-23 2023-05-24 TotalEnergies OneTech Procédé de désodorisation d'huiles lubrifiantes régénérées utilisant du co2 supercritique
WO2023094285A1 (fr) 2021-11-23 2023-06-01 Totalenergies Onetech Procédé de désodorisation d'huiles lubrifiantes régénérées au moyen de co2 supercritique

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