WO2007014903A1 - Verfahren zum nachweis einer kraftstoffadditiv-komponente - Google Patents
Verfahren zum nachweis einer kraftstoffadditiv-komponente Download PDFInfo
- Publication number
- WO2007014903A1 WO2007014903A1 PCT/EP2006/064745 EP2006064745W WO2007014903A1 WO 2007014903 A1 WO2007014903 A1 WO 2007014903A1 EP 2006064745 W EP2006064745 W EP 2006064745W WO 2007014903 A1 WO2007014903 A1 WO 2007014903A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fuel additive
- fuel
- additive component
- indicator
- analyte
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 26
- 239000000446 fuel Substances 0.000 claims abstract description 28
- 239000012491 analyte Substances 0.000 claims abstract description 23
- 230000008859 change Effects 0.000 claims abstract description 15
- 230000003993 interaction Effects 0.000 claims abstract description 6
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- POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 description 1
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- 239000011159 matrix material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
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- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
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- JCYPECIVGRXBMO-FOCLMDBBSA-N methyl yellow Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1 JCYPECIVGRXBMO-FOCLMDBBSA-N 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- ZLQJVGSVJRBUNL-UHFFFAOYSA-N methylumbelliferone Natural products C1=C(O)C=C2OC(=O)C(C)=CC2=C1 ZLQJVGSVJRBUNL-UHFFFAOYSA-N 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 1
- 235000007708 morin Nutrition 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- HQHBAGKIEAOSNM-UHFFFAOYSA-N naphtholphthalein Chemical compound C1=CC=C2C(C3(C4=CC=CC=C4C(=O)O3)C3=CC=C(C4=CC=CC=C43)O)=CC=C(O)C2=C1 HQHBAGKIEAOSNM-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- VDDWRTZCUJCDJM-PNHLSOANSA-N p-Naphtholbenzein Chemical compound C12=CC=CC=C2C(O)=CC=C1\C(=C\1C2=CC=CC=C2C(=O)C=C/1)C1=CC=CC=C1 VDDWRTZCUJCDJM-PNHLSOANSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000007793 ph indicator Substances 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- GVKCHTBDSMQENH-UHFFFAOYSA-L phloxine B Chemical compound [Na+].[Na+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 GVKCHTBDSMQENH-UHFFFAOYSA-L 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000002824 redox indicator Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- 239000002455 scale inhibitor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- ZHFPEICFUVWJIS-UHFFFAOYSA-M sodium 2-hydroxy-5-[(3-nitrophenyl)diazenyl]benzoate Chemical compound [Na+].Oc1ccc(cc1C([O-])=O)N=Nc1cccc(c1)[N+]([O-])=O ZHFPEICFUVWJIS-UHFFFAOYSA-M 0.000 description 1
- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 1
- AZLXCBPKSXFMET-UHFFFAOYSA-M sodium 4-[(4-sulfophenyl)diazenyl]naphthalen-1-olate Chemical compound [Na+].C12=CC=CC=C2C(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 AZLXCBPKSXFMET-UHFFFAOYSA-M 0.000 description 1
- JGCBNZLRTUKUAQ-UHFFFAOYSA-M sodium 4-[[4-(benzylamino)phenyl]diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(S(=O)(=O)[O-])=CC=C1N=NC(C=C1)=CC=C1NCC1=CC=CC=C1 JGCBNZLRTUKUAQ-UHFFFAOYSA-M 0.000 description 1
- TYVJJYHBZVERDC-UHFFFAOYSA-N sodium 8-hydroxy-7-[(4-nitrophenyl)diazenyl]naphthalene-1,6-disulfonic acid Chemical compound C1=CC2=CC(=C(C(=C2C(=C1)S(=O)(=O)O)O)N=NC3=CC=C(C=C3)[N+](=O)[O-])S(=O)(=O)O.[Na+] TYVJJYHBZVERDC-UHFFFAOYSA-N 0.000 description 1
- MLVYOYVMOZFHIU-UHFFFAOYSA-M sodium;4-[(4-anilinophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(S(=O)(=O)[O-])=CC=C1N=NC(C=C1)=CC=C1NC1=CC=CC=C1 MLVYOYVMOZFHIU-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XOSXWYQMOYSSKB-LDKJGXKFSA-L water blue Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC(C=C2)=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C(C=C2)=CC=C2S([O-])(=O)=O)=CC(S(O)(=O)=O)=C1N.[Na+].[Na+] XOSXWYQMOYSSKB-LDKJGXKFSA-L 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000019235 yellow 2G Nutrition 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/26—Oils; Viscous liquids; Paints; Inks
- G01N33/28—Oils, i.e. hydrocarbon liquids
- G01N33/2835—Specific substances contained in the oils or fuels
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/22—Fuels; Explosives
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
- G01N21/80—Indicating pH value
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/142222—Hetero-O [e.g., ascorbic acid, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/145555—Hetero-N
Definitions
- the present invention relates to a method for the qualitative or quantitative detection of a fuel additive component, in particular in diesel fuel or gasoline. Furthermore, the subject of the present invention is the use of this method for the qualitative or quantitative detection of a fuel additive component in diesel fuel or gasoline.
- Petrol consists of a hydrocarbon mixture, which may contain, for example, additives of oxygen-containing organic components and additives to improve the properties.
- additives which are used in unleaded gasoline are e.g. Antioxidants, corrosion inhibitors, metal deactivators and detergents.
- the additives are used inter alia to prevent corrosion, deposits in the inlet system, sludge formation and valve sticking in an internal combustion engine.
- the additive concentrations are usually in gasoline in the range below 0.1 wt .-%.
- the additives are usually already metered by the fuel manufacturer in the form of additive packages and added to the petrol when filling the tank trucks in the refinery.
- diesel fuel Even with diesel fuel, the addition of additives for quality improvement has largely prevailed.
- the diesel fuel is usually added additive packages with a total concentration below 0.1 wt .-%.
- the most common additives for diesel fuel are flow improvers, lubricity improvers, ignition improvers, detergents, corrosion inhibitors and antifoams.
- a method has been found for the qualitative or quantitative detection of a fuel additive component, which is part of an analyte containing fuel and / or other fuel additive components, which is characterized in that the analyte is brought into contact with an indicator and by the Interaction between fuel additive component and indicator determined change in the color properties of the indicator determined in the analyte.
- the method according to the invention can be used qualitatively and quantitatively, i. It can hereby be proven whether a certain fuel additive component is present and in what quantity it is present.
- the proof can be carried out in particular in the fuel itself, but also in the underlying additive packages.
- the analyte, ie, the determination sample is thus the fuel or fuel additive package, which may be diluted with suitable inert solvents, if necessary, to carry out the determination.
- all indicators are considered as indicators which change their color properties upon contact with and interaction with the fuel additive component, be they in the range of visible light or in the range of fluorescence or chemiluminescence behavior.
- an acid-base indicator (also referred to as a pH indicator or neutralization indicator) is used.
- the acids or bases on which these indicators are based show a color change which usually occurs in the visible range during their protolysis or deproteinization.
- Typical examples of acid-base indicators are cresol red, metanil yellow, thymol blue, m-cresol purple, tropaeolin OO, 2,6-dinitrophenol, benzyl orange, 2,4-dinitrophenol, benzopurpurine 4 B, dimethyl yellow, Congo Red, Bromophenol blue, bromochlorophenol blue, methyl orange, ⁇ -naphthyl red, bromocresol green, 2,5-dinitrophenol, mixed indicator 5, methyl red, ethyl red, chlorophenol red, carminic acid, alizarin red S, 2-nitrophenol, litmus, bromocresol purple, bromophenol red, 4-nitrophenol, alizarin, Bromothymol blue, bromoxylenol blue,
- bromocresol green As a particularly preferred acid-base indicator, bromocresol green, ⁇ -naphthyl red, 2,5-dinitrophenol, mixed indicator 5 or methyl red is used.
- the acid-base indicator exploits basic functionalities in the fuel additive component to produce the color change.
- adsorption indicators e.g. Fluorescein or eosin
- fluorescence indicators e.g. Flucescein, eosin, benzoflavin, phloxine, chromotropic acid, methylumbelliferone, benzquinoline, morin, naphthols, naphthionic acid, quinine, coumarin or acridine
- chemiluminescent indicators e.g. Lucigenin
- redox indicators e.g. Neutral red, safranine or methylene blue
- metal indicators metal indicators
- a specific color change occurs when the indicator and the analyte come together, for example in the case of bromocresol green from yellow (acidic range below pH 3.8) to blue (alkaline range above pH 5, 4).
- the occurrence of the color change is the evidence of the presence of the desired fuel additive component.
- a blank test with an analyte to which a test quantity of the fuel additive component to be detected has been added and / or an analyte containing unadditized fuel is recommended.
- the intensity of the coloration is determined after the change in the color properties in the analyte, ie after the color change has taken place.
- the photometric determination is suitable in a preferred embodiment, usually using commercially available photometers.
- the measurement is usually carried out by adding a certain amount of analyte to a set amount of the indicator, mixing (for example by shaking) and irradiating the sample in a sample vessel (cuvette) with light of a specific wavelength.
- the measured absorbance correlated to a blank or to a calibration curve made with different amounts of the fuel additive component to be determined gives the amount of fuel additive component in the analyte.
- the photometric determination of the extinction at a wavelength of 620 nm is recommended, for example.
- the analyte used is diesel fuel or gasoline which, in addition to the fuel additive component to be detected, optionally contains further fuel additive components, ie the determination is carried out directly on the diesel or gasoline fuel supplied by the refineries and commercially available ,
- petrol for operating internal combustion engines (gasoline engines) in motor vehicles are usually petroleum raffinates, which generally have a boiling range of 70 to 18O 0 C. They usually represent C5-C12 hydrocarbon mixtures of alkanes, alkenes, cycloalkanes, cycloalkenes and aromatics in varying composition. Petrol is preferably used unleaded.
- the method according to the invention for detecting a fuel additive component can in principle also be carried out in kerosene as analyte.
- Kerosene as a higher-boiling gasoline grade (boiling range about 180 to 27O 0 C) is used in particular in the aircraft sector.
- diesel fuels whose major components are longer chain paraffins
- those obtainable by coal gasification or gas liquefaction [GTL] fuels are also suitable.
- mixtures of the abovementioned diesel fuels with regenerative fuels such as biodiesel or bioethanol.
- regenerative fuels such as biodiesel or bioethanol.
- Diesel fuels may also contain water, for example in an amount of up to 20% by weight, for example in the form of diesel-water microemulsions or as so-called "white diesel".
- the process of the present invention is used to detect a polar detergent-additive component typically used as an additive in most types of fuel, particularly diesel fuel and gasoline, as well as in the underlying additive compositions (especially additive packages) for diesel or diesel fuel Petrol is located.
- a polar detergent-additive component typically used as an additive in most types of fuel, particularly diesel fuel and gasoline, as well as in the underlying additive compositions (especially additive packages) for diesel or diesel fuel Petrol is located.
- overall suitable polar detergent additives with in particular basic functionalities or polar functional groups, which interact with the indicators mostly in the sense of an acid-base interaction, are described below.
- the above additive compositions and fuels may additionally contain various other fuel additive components such as demulsifiers, carrier oils, solvents and diluents, corrosion inhibitors, antioxidants, metal deactivators, antistatic agents, color markers, flow improvers, lubricity improvers, ignition improvers and antifoam agents.
- Suitable other fuel additive components are also set forth below.
- Detergent additives are commonly referred to as gasoline and diesel fuel scale inhibitors.
- the detergent additives are amphiphilic substances having at least one hydrophobic hydrocarbon radical having a number average molecular weight (Mn) of from 85 to 20,000 and at least one polar moiety selected from:
- the hydrophobic hydrocarbon radical in the above detergent additives which provides the sufficient solubility in the fuel, has a number average molecular weight (Mn) of 85 to 20,000, especially from 113 to 10,000, especially from 300 to 5000.
- Mn number average molecular weight
- polypropene or conventional (ie, with predominantly central double bonds) polybutene or polyisobutene with Mn 300 to 5000.
- amines such as e.g.
- Ammonia monoamines or polyamines, such as dimethylaminopropylamine, ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine.
- Corresponding additives based on poly (iso) butene are in particular in EP-B 244 616, corresponding additives based on polypropene are described in particular in WO 94/24231.
- monoamino groups (a) containing additives are the polyisobutene epoxides by reaction with amines and subsequent dehydration and reduction of the amino alcohols obtainable compounds, as described in particular in DE-A 196 20 262.
- Carboxyl groups or their alkali metal or alkaline earth metal salts (d) containing additives are preferably copolymers of C2-C4o-olefins with maleic anhydride having a total molecular weight of 500 to 20,000, the carboxyl groups wholly or partially to the alkali metal or alkaline earth metal salts and a remainder of the Carboxyl groups are reacted with alcohols or amines.
- additives are known in particular from EP-A 307 815.
- Such additives are primarily used to prevent valve seat wear and, as described in WO 87/01126, can be advantageously used in combination with conventional fuel detergents such as poly (iso) butenamines or polyetheramines.
- Sulfonic acid groups or their alkali metal or alkaline earth metal salts (e) containing additives are preferably alkali metal or alkaline earth metal salts of a Sulfobern- steinklaklalesters, as described in particular in EP-A 639 632.
- Such additives are mainly used to prevent valve seat wear and can be used to advantage in combination with conventional fuel detergents such as poly (iso) buteneamines or polyetheramines.
- Polyoxy-C 2 -C 4 -alkylene groups (f) containing additives are preferably polyether or polyetheramines, which by reaction of C 2 -C 6 o-alkanols, C 6 -C 30 -alkanediols, mono- or di-C 2 -C 3 o-alkylamines, Ci-C 3 o-alkylcyclohexanols or Ci-C 30 - alkylphenols with 1 to 30 moles of ethylene oxide and / or propylene oxide and / or butylene oxide per hydroxyl group or amino group and, in the case of polyetheramines, by subsequent reductive amination with ammonia, monoamines or polyamines are available.
- Such products are disclosed in particular in EP-A 310 875,
- EP-A 356 725, EP-A 700 985 and US-A 4,877,416 In the case of polyesters, such products also fulfill carrier oil properties. Typical examples thereof are tridecanol or isotridecanol butoxylates, isononylphenol butoxylates and also polyisobutenol butoxylates and propoxylates and the corresponding reaction products with ammonia.
- Carboxyl ester groups (g) containing additives are preferably esters of mono-, di- or tricarboxylic acids with long-chain alkanols or polyols, especially those having a minimum viscosity of 2 mm 2 / s at 100 0 C, as described in particular in DE-A 38 38 918 are.
- Aliphatic or aromatic acids can be used as the mono-, di- or tricarboxylic acids, especially suitable as ester alcohols or polyols are long-chain representatives with, for example, 6 to 24 C atoms.
- esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of iso-octanol, iso-nonanol, iso-decanol and of isotridecanol. Such products also meet carrier oil properties.
- derivatives with aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine.
- the groups having hydroxyl and / or amino and / or amido and / or imido groups are, for example, carboxylic acid groups, acid anhydrides, acid amides of diamines or polyamines which, in addition to the amide function, still have free amine groups, succinic acid derivatives with an acid - And an amide function, carboxylic imides with monoamines, carboxylic imides with di- or polyamines, which still have free amine groups in addition to the imide function, and diimides, which are formed by the reaction of di- or polyamines with two succinic acid derivatives.
- Such fuel additives are described in particular in US Pat. No. 4,849,572.
- Mannich reaction of substituted phenols with aldehydes and mono- or polyamines generated groupings (i) containing additives are preferably reaction products of polyisobutene-substituted phenols with formaldehyde and mono- or polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine or dimethylaminopropylamine.
- Such "polyisobutene-Mannich bases" are described in particular in EP-A-831 141.
- Detergent additives from group (h) are particularly preferred in the process according to the invention. These are, in particular, polyisobutenyl-substituted succinimides, especially the imides with aliphatic polyamines. Such polyisobutenyl-substituted succinimides are primarily used as a polar fuel additive component with detergent action in diesel fuel.
- Demulsifiers are substances which cause the separation of an emulsion. These may be both ionogenic and non-ionic substances which are effective at the phase boundary. Accordingly, basically all surface-active substances are suitable as demulsifiers. Particularly suitable demulsifiers are selected from anion-active compounds such as the alkali or alkaline earth salts of alkyl-substituted phenol and naphthalenesulfonates and the alkali or alkaline earth salts of fatty acids, as well as neutral compounds such as alcohol alkoxylates, e.g. Alcohol ethoxylates, phenol alkoxylates, e.g.
- tert-butylphenol ethoxylate or tert-pentylphenol ethoxylate fatty acids, alkylphenols, condensation products of ethylene oxide (EO) and propylene oxide (PO), e.g. also in the form of EO / PO block copolymers, polyethyleneimines or else polysiloxanes.
- EO ethylene oxide
- PO propylene oxide
- the additive composition and the fuel can also be combined with other conventional components and additives.
- carrier oils without pronounced detergent action to name, and these come in particular when used in petrol fuel to fruition. Occasionally, however, they are also used in middle distillates.
- Carrier oils are usually used in combination with detergent additives and exercise with these a solvent or washing function.
- Carrier oils are typically high boiling, viscous, thermostable liquids which coat a hot metal surface and thereby prevent the formation or deposition of contaminants on the metal surface.
- Suitable mineral carrier oils are fractions obtained in petroleum processing, such as bright stock or base oils with viscosities such as from class SN 500-2000; but also aromatic hydrocarbons, paraffinic hydrocarbons and alkoxyalkanols. Useful is also a technique known as "hydrocrack oil” and obtained in the refining of mineral oil fraction (vacuum distillate cut having a boiling range of about 360-500 0 C, available natural out catalytic high pressure table hydrogenated and isomerized and also deparaffinized mineral oil). Also suitable are mixtures of the abovementioned mineral carrier oils.
- Examples of synthetic carrier oils which can be used according to the invention are selected from polyolefins (polyalphaolefins or polyethylenemolefins), (poly) esters, (poly) acrylates, polyethers, aliphatic polyetheramines, alkylphenol-initiated polyethers, alkylphenol-initiated polyetheramines and carboxylic acid esters of long-chain alkanols.
- suitable polyethers or polyetheramines are preferably compounds containing polyoxy-C 2 -C 4 -alkylene groups, which are prepared by reacting C 2 -C 6 -alkanols, C 6 -C 50 -alkanediols, mono- or di-C 2 -C 30 -alkylamines, C 1 -C 30 -alkyl - Cyclohexanolen or Ci-C3o-Alkylphenolen with 1 to 30 mol of ethylene oxide and / or propylene oxide and / or butylene oxide per hydroxyl group or amino group and, in the case of polyether amines, by subsequent reductive amination with ammonia, mono amines or polyamines are available.
- Such products are described in particular in EP-A 310 875, EP-A 356 725, EP-A 700 985 and US-A 4,877,416.
- polyetheramines poly-C 2 -C 6 -alkylene oxide amines or functional derivatives thereof can be used. Typical examples of these are tridecanol or Isotridecanolbutoxylate, Isononylphenolbutoxylate and Polyisobutenolbutoxylate and propoxylates and the corresponding reaction products with ammonia.
- carboxylic acid esters of long-chain alkanols are in particular esters of mono-, di- or tricarboxylic acids with long-chain alkanols or polyols, as described in particular in DE-A 38 38 918.
- mono-, di- or tricarboxylic acids it is possible to use aliphatic or aromatic acids, especially suitable ester alcohols or polyols are long-chain representatives having, for example, 6 to 24 carbon atoms.
- suitable representatives of the esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of isooctanol, isononanol, isodecanol and isotridecanol, such as e.g. Di (n- or iso-tridecyl) phthalate.
- suitable synthetic carrier oils are alcohol-started polyethers having about 5 to 35, such as about 5 to 30, C 3 -C 6 alkylene oxide units, for example selected from propylene oxide, n-butylene oxide and i-butylene oxide units, or mixtures from that.
- suitable starter alcohols are long-chain alkanols or long-chain alkyl-substituted phenols, where the long-chain alkyl radical is in particular a straight-chain or branched C 6 -C 18 -alkyl radical.
- Preferred examples are tridecanol and nonylphenol.
- Further common additives are the cold properties of the fuel-improving additives, e.g. Nucleators, flow improvers, paraffin dispersants and mixtures thereof, e.g. Ethylene-vinyl acetate copolymers; Corrosion inhibitors, for example based on film-forming ammonium salts of organic carboxylic acids or of heterocyclic aromatics in the case of non-ferrous metal corrosion protection; dehazers; Anti-foaming agent, e.g.
- siloxane compounds cetane number improvers (ignitability improvers); combustion improvers; Antioxidants or stabilizers, for example based on amines such as p-phenylenediamine, dicyclohexylamine or derivatives thereof or of phenols such as 2,4-di-tert-butylphenol or 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid; Antistatic agents; Metallocenes such as ferrocene; Methylcyclopentadienyl manganese tricarbonyl; Lubricity improver, e.g.
- fatty acids alkenyl succinic esters, bis (hydroxyalkyl) fatty amines, hydroxyacetamides or castor oil; as well as dyes (markers).
- amines are added to lower the pH of the fuel.
- Suitable diluents and solvents are, for example, aromatic and aliphatic hydrocarbons, for example Cs-Cio-alkanes, such as pentane, hexane, heptane, octane, nonane, decane, their constitution isomers and mixtures; Petroleum ethers, aromatics such as benzene, toluene, xylene and solvent naphtha; Alkanols of 3 to 8 carbon atoms, e.g. Propanol, isopropanol, n-butanol, sec-butanol, isobutanol and the like, in combination with hydrocarbon solvents; and alkoxyalkanoethylene.
- aromatic and aliphatic hydrocarbons for example Cs-Cio-alkanes, such as pentane, hexane, heptane, octane, nonane, decane, their constitution isomers and mixtures
- Suitable diluents are, for example, fractions obtained in petroleum processing, such as kerosene, naphtha or bright stock.
- middle distillates especially in diesel fuels and heating oils preferred diluent used are naphtha, kerosene, diesel fuels, aromatic hydrocarbons such as Solvent Naphtha heavy, Solvesso ® or Shellsol ®, as well as mixtures of these solvents and diluents.
- detergent additives e.g. those with the polar groupings (a) to (i), in the fuel, in particular in diesel fuel or gasoline, are used, they are the fuel usually in an amount of 10 to 5000 ppm by weight, especially 50 to 1000 parts by weight. ppm, added.
- demulsifiers When demulsifiers are used, they are usually added to the fuel in an amount of 0.1 to 100 ppm by weight, especially 0.2 to 10 ppm by weight.
- the subject of the present invention is the use of the described method for the qualitative or quantitative detection of a fuel additive component in a diesel fuel or gasoline containing the fuel additive component and optionally further fuel additive components as analytes lyte.
- the method according to the invention is a simple detection method for a fuel additive component, in particular a basic detergent additive, in a fuel additive package or in the fuel itself and can also be carried out "on site", ie in the refinery or at the filling station, with simple measuring instruments
- the detection method is largely independent of the origin of the respective fuel grade, ie the composition of the respective fuel has no influence on the interaction between the fuel additive component and the indicator caused change in the color properties of the indicator in the analyte.
- Samples of commercially available unadditized diesel fuel from various refineries and refinery cuts were each mixed with the same amounts of a detergent additive based on the imide of polyisobutenylsuccinic anhydride (number average molecular weight of the polyisobutenyl radical: about 1000) and tetraethylene pentamine, which is in the form of a conventional Diesel performance package was added, additized in practical quantities. From the extinction values determined with the different dosing rates of the detergent additive in the individual diesel fuel samples (analytes) in a commercially available photometer, a corresponding calibration curve for the range from 0 to 170 ppm by weight of detergent additive (based on active substance) was prepared.
- 1.0 ml of an ethanolic bromocresol green solution (13 mg bromocresol green in 100 ml ethanol, red-orange solution) was added to 10 ml of additized diesel fuel.
- the measurements were carried out after a color change in the analyte from yellow to blue, which was initiated and completed by vigorously shaking the sample with the indicator solution in a volumetric flask, in a 1 ml cuvette at a wavelength of 620 nm.
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Priority Applications (7)
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JP2008524494A JP2009503526A (ja) | 2005-08-03 | 2006-07-27 | 燃料添加剤成分を検出する方法 |
EP06792588A EP1913369A1 (de) | 2005-08-03 | 2006-07-27 | Verfahren zum nachweis einer kraftstoffadditiv-komponente |
MX2008000952A MX2008000952A (es) | 2005-08-03 | 2006-07-27 | Metodo para detectar un componente de aditivo de combustible. |
AU2006274842A AU2006274842A1 (en) | 2005-08-03 | 2006-07-27 | Method for detecting a fuel additive component |
US11/997,179 US20080233656A1 (en) | 2005-08-03 | 2006-07-27 | Method For Detecting a Fuel Additive Component |
CA002618234A CA2618234A1 (en) | 2005-08-03 | 2006-07-27 | Method for detecting a fuel additive component |
NO20080294A NO20080294L (no) | 2005-08-03 | 2008-01-16 | Fremgangsmate for a pavise en drivstoffadditivkomponent |
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DE102005037112.4 | 2005-08-03 | ||
DE102005037112A DE102005037112A1 (de) | 2005-08-03 | 2005-08-03 | Verfahren zum Nachweis einer Kraftstoffadditiv-Komponente |
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US (1) | US20080233656A1 (de) |
EP (1) | EP1913369A1 (de) |
JP (1) | JP2009503526A (de) |
KR (1) | KR20080041213A (de) |
CN (1) | CN101228432A (de) |
AU (1) | AU2006274842A1 (de) |
CA (1) | CA2618234A1 (de) |
DE (1) | DE102005037112A1 (de) |
MX (1) | MX2008000952A (de) |
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WO2009120563A1 (en) * | 2008-03-25 | 2009-10-01 | The Lubrizol Corporation | Marker dyes for petroleum products |
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WO2008092809A1 (de) * | 2007-01-29 | 2008-08-07 | Basf Se | Verzweigte decylnitrate und ihre verwendung als verbrennungsverbesserer und/oder cetanzahlverbesserer in kraftstoffen |
DE102008044299A1 (de) * | 2008-12-03 | 2010-06-10 | Robert Bosch Gmbh | Vorrichtung zur Überwachung eines Betriebsfluids für Kraftfahrzeuge und Verfahren zum Betrieb derselben |
BR102012029230A2 (pt) * | 2012-11-16 | 2014-12-23 | Univ Fed Do Amazonas | Processo para monitoramento da qualidade de combustível e óleos lubrificantes e kit para realizar o referido monitoramento |
US9678002B2 (en) * | 2014-10-29 | 2017-06-13 | Chevron U.S.A. Inc. | Method and system for NIR spectroscopy of mixtures to evaluate composition of components of the mixtures |
JP6438508B2 (ja) | 2017-02-28 | 2018-12-12 | 株式会社Subaru | エンジン制御装置 |
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- 2005-08-03 DE DE102005037112A patent/DE102005037112A1/de not_active Withdrawn
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2006
- 2006-07-27 RU RU2008107577/28A patent/RU2008107577A/ru unknown
- 2006-07-27 AU AU2006274842A patent/AU2006274842A1/en not_active Abandoned
- 2006-07-27 CN CNA2006800269967A patent/CN101228432A/zh active Pending
- 2006-07-27 WO PCT/EP2006/064745 patent/WO2007014903A1/de active Application Filing
- 2006-07-27 MX MX2008000952A patent/MX2008000952A/es unknown
- 2006-07-27 KR KR1020087004077A patent/KR20080041213A/ko not_active Application Discontinuation
- 2006-07-27 EP EP06792588A patent/EP1913369A1/de not_active Ceased
- 2006-07-27 CA CA002618234A patent/CA2618234A1/en not_active Abandoned
- 2006-07-27 JP JP2008524494A patent/JP2009503526A/ja not_active Withdrawn
- 2006-07-27 US US11/997,179 patent/US20080233656A1/en not_active Abandoned
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2009120563A1 (en) * | 2008-03-25 | 2009-10-01 | The Lubrizol Corporation | Marker dyes for petroleum products |
US8257975B2 (en) | 2008-03-25 | 2012-09-04 | The Lubrizol Corporation | Marker dyes for petroleum products |
Also Published As
Publication number | Publication date |
---|---|
EP1913369A1 (de) | 2008-04-23 |
CN101228432A (zh) | 2008-07-23 |
AU2006274842A1 (en) | 2007-02-08 |
NO20080294L (no) | 2008-02-13 |
JP2009503526A (ja) | 2009-01-29 |
KR20080041213A (ko) | 2008-05-09 |
US20080233656A1 (en) | 2008-09-25 |
MX2008000952A (es) | 2008-03-27 |
CA2618234A1 (en) | 2007-02-08 |
DE102005037112A1 (de) | 2007-02-08 |
RU2008107577A (ru) | 2009-09-10 |
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