EP0436864B1 - Carburants pour moteurs à allumage par étincelle - Google Patents
Carburants pour moteurs à allumage par étincelle Download PDFInfo
- Publication number
- EP0436864B1 EP0436864B1 EP90124072A EP90124072A EP0436864B1 EP 0436864 B1 EP0436864 B1 EP 0436864B1 EP 90124072 A EP90124072 A EP 90124072A EP 90124072 A EP90124072 A EP 90124072A EP 0436864 B1 EP0436864 B1 EP 0436864B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- fuel
- carbon atoms
- straight
- amides
- fuels
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000446 fuel Substances 0.000 title claims description 20
- 150000001412 amines Chemical class 0.000 claims description 18
- 150000001408 amides Chemical class 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000003599 detergent Substances 0.000 claims description 6
- 230000007797 corrosion Effects 0.000 claims description 5
- 238000005260 corrosion Methods 0.000 claims description 5
- -1 amide ammonium salts Chemical class 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 150000007942 carboxylates Chemical group 0.000 claims 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000005131 dialkylammonium group Chemical group 0.000 claims 1
- 239000003760 tallow Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 description 10
- 239000000654 additive Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000003863 ammonium salts Chemical group 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000006294 amino alkylene group Chemical group 0.000 description 3
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- JTQQDDNCCLCMER-CLFAGFIQSA-N (z)-n-[(z)-octadec-9-enyl]octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCNCCCCCCCC\C=C/CCCCCCCC JTQQDDNCCLCMER-CLFAGFIQSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical class NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- QUISWUAUMRRNFA-UHFFFAOYSA-N n-docosyldocosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCCCCCC QUISWUAUMRRNFA-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/224—Amides; Imides carboxylic acid amides, imides
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B1/00—Engines characterised by fuel-air mixture compression
- F02B1/02—Engines characterised by fuel-air mixture compression with positive ignition
- F02B1/04—Engines characterised by fuel-air mixture compression with positive ignition with fuel-air mixture admission into cylinder
Definitions
- the invention relates to fuels for gasoline engines with small amounts of amides or amidammonium salts from aminoalkylene polycarboxylic acids and secondary long-chain amines.
- Carburetor and intake system of gasoline engines are increasingly contaminated by contaminants caused by dust particles from the air, unburned hydrocarbon residues from the combustion chamber and the crankcase ventilation gases that are led into the carburetor.
- the first generation of additives could only prevent the formation of deposits in the intake system, but not remove existing deposits again, whereas the modern additives of the second generation can do both ("keep-clean” and “clean-up effect") and indeed, due to changed thermal properties, in particular also at zones of higher temperatures, namely at the inlet valves.
- the molecular construction principle of fuel detergents can be generalized as a link between polar structures and mostly higher molecular weight, non-polar or lipophilic residues.
- No. 2,901,335 discloses amine salts of aminocarboxylic acids which are used in leaded fuels to stabilize the lead compounds.
- A is a straight-chain or branched alkylene radical having 2 to 6 carbon atoms or the rest of the formula and R essentially denotes straight-chain aliphatic radicals, in particular alkyl radicals having 10 to 30, preferably 14 to 24, carbon atoms, the amide structures also partly in the form of the ammonium salt structure of the formula can be present, is particularly effective with regard to carburetor and valve cleaning.
- the amides or amide ammonium salts e.g. Nitrilotriacetic acid, ethylenediaminetetraacetic acid or propylene-1,2-diaminetetraacetic acid are obtained by reacting the acids with 0.5 to 1.5 mol amine, preferably 0.8 to 1.2 mol amine per carboxyl group.
- reaction temperatures are about 80 to 200 ° C, with the amides being continuously removed from the water of reaction formed. However, the reaction does not have to be completely led to the amide.
- Dialkylamines are particularly suitable in which R is a straight-chain alkyl radical having 10 to 30 carbon atoms, preferably 14 to 24 carbon atoms.
- Dioleylamine, dipalmitinamine, dicoconut fatty amine and dibehenylamine and preferably ditallow fatty amine may be mentioned in particular.
- the amides or ammonium salts of the amino alkylene polycarboxylic acids of the formulas I and II to be used according to the invention are added to the fuels in amounts of 50 to 1500 ppm, preferably 50 to 1000 ppm, in particular 100 to 500 ppm.
- Leaded and unleaded regular and premium gasoline can be used as fuels for gasoline engines.
- the gasolines can also contain components other than hydrocarbons, e.g. Alcohols such as methanol, ethanol, tert-butanol and ethers, e.g. Contain methyl tertiary butyl ether.
- the fuels generally also contain further additives such as corrosion inhibitors, stabilizers, antioxidants and / or detergents.
- Corrosion inhibitors are mostly ammonium salts org. Carboxylic acids which tend to form films due to the structure of the starting compounds. Amines to lower the pH are also often found in corrosion inhibitors. Heterocyclic aromatics are mostly used as non-ferrous metal corrosion protection.
- amines such as para-phenylenediamine, dicyclohexylamine, morpholine or derivatives of these amines are antioxidants or stabilizers call.
- Phenolic antioxidants such as 2,4-di-tert-butylphenol or 3,5-di-tert-butyl-4-hydroxiphenylpropionic acid and their derivatives are also added to fuels and lubricants.
- Amides and imides of polyisobutylene succinic anhydride, polybutene polyamines and long-chain carbonamides and imides are also optionally contained in the fuels as further carburetor, injector and valve detergents.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
Claims (6)
- Carburants pour moteurs à allumage par étincelles, qui contiennent, à titre de détergent, des proportions actives d'amides ou de sels d'amidammonium répondant aux formules I et II
- Carburants suivant la revendication 1, qui contiennent des sels d'amides ou d'amidammonium et leurs mélanges, caractérisés en ce que le radical R représente un groupe alkyle à chaîne droite comportant de 14 à 24 atomes de carbone.
- Carburants selon la revendication 1, caractérisés en ce qu'ils contiennent des composés de la formule
- Carburants suivant la revendication 1, caractérisés en ce qu'ils contiennent les composés des formules I et II en proportions de 50 à 1500 ppm, par rapport au carburant.
- Carburants suivant la revendication 1, caractérisés en ce qu'ils contiennent d'autres détergents pour carburants, des agents antigivrage, des inhibiteurs de corrosion et/ou d'autres antioxydants.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4000539A DE4000539A1 (de) | 1990-01-10 | 1990-01-10 | Kraftstoffe fuer ottomotoren |
DE4000539 | 1990-01-10 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0436864A1 EP0436864A1 (fr) | 1991-07-17 |
EP0436864B1 true EP0436864B1 (fr) | 1993-09-22 |
Family
ID=6397836
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP90124072A Expired - Lifetime EP0436864B1 (fr) | 1990-01-10 | 1990-12-13 | Carburants pour moteurs à allumage par étincelle |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0436864B1 (fr) |
CA (1) | CA2033829A1 (fr) |
DE (2) | DE4000539A1 (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2022360759A1 (en) * | 2021-10-04 | 2024-02-29 | Innospec Fuel Specialties Llc | Improvements in fuels |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2901335A (en) * | 1954-10-05 | 1959-08-25 | Standard Oil Co | Additive for leaded gasoline |
US3893825A (en) * | 1970-12-30 | 1975-07-08 | Universal Oil Prod Co | Inhibition of corrosion |
DE2531469C3 (de) * | 1975-07-15 | 1980-10-23 | Basf Ag, 6700 Ludwigshafen | Verwendung von w -N.N.N'.N'tetrasubstituierten Aminoalkansäureamiden, w -N,N,N',N'tetrasubstituierte Aminobuttersäure-amide und Verfahren zu deren Herstellung |
DE2828038A1 (de) * | 1978-06-26 | 1980-01-10 | Basf Ag | Kraftstoffe fuer ottomotoren |
-
1990
- 1990-01-10 DE DE4000539A patent/DE4000539A1/de not_active Withdrawn
- 1990-12-13 EP EP90124072A patent/EP0436864B1/fr not_active Expired - Lifetime
- 1990-12-13 DE DE90124072T patent/DE59002846D1/de not_active Expired - Fee Related
-
1991
- 1991-01-09 CA CA002033829A patent/CA2033829A1/fr not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
DE4000539A1 (de) | 1991-07-11 |
EP0436864A1 (fr) | 1991-07-17 |
CA2033829A1 (fr) | 1991-07-11 |
DE59002846D1 (de) | 1993-10-28 |
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