EP0282845A1 - Combustibles contenant de petites quantités d'alcoxylate et d'imide d'acide polycarboxylique - Google Patents
Combustibles contenant de petites quantités d'alcoxylate et d'imide d'acide polycarboxylique Download PDFInfo
- Publication number
- EP0282845A1 EP0282845A1 EP88103420A EP88103420A EP0282845A1 EP 0282845 A1 EP0282845 A1 EP 0282845A1 EP 88103420 A EP88103420 A EP 88103420A EP 88103420 A EP88103420 A EP 88103420A EP 0282845 A1 EP0282845 A1 EP 0282845A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- oxide
- valve
- alkoxylates
- fuels
- engine
- 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.)
- Granted
Links
- 239000000446 fuel Substances 0.000 title claims abstract description 28
- 150000003949 imides Chemical class 0.000 title claims abstract description 6
- 239000002253 acid Substances 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims abstract description 38
- 150000001412 amines Chemical class 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 11
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims abstract description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 6
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- -1 amide imides Chemical class 0.000 abstract description 7
- 238000012360 testing method Methods 0.000 description 34
- 239000000654 additive Substances 0.000 description 18
- 230000000996 additive effect Effects 0.000 description 14
- 239000002816 fuel additive Substances 0.000 description 14
- 239000003921 oil Substances 0.000 description 12
- 239000007789 gas Substances 0.000 description 11
- 125000002947 alkylene group Chemical group 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 239000010705 motor oil Substances 0.000 description 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 description 6
- 239000003502 gasoline Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 238000006073 displacement reaction Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000002283 diesel fuel Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 241000722921 Tulipa gesneriana Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical compound OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000003749 cleanliness Effects 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003595 mist Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- CJYDNDLQIIGSTH-UHFFFAOYSA-N 1-(3,5,7-trinitro-1,3,5,7-tetrazocan-1-yl)ethanone Chemical compound CC(=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 CJYDNDLQIIGSTH-UHFFFAOYSA-N 0.000 description 1
- JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical compound CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 description 1
- JTOSHSWKQMEPKA-UHFFFAOYSA-N 1-n,1-n-dimethylpentane-1,4-diamine Chemical compound CC(N)CCCN(C)C JTOSHSWKQMEPKA-UHFFFAOYSA-N 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- XAYDWGMOPRHLEP-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical class C1CCCC2OC21C=C XAYDWGMOPRHLEP-UHFFFAOYSA-N 0.000 description 1
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 1
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 1
- MELPJGOMEMRMPL-UHFFFAOYSA-N 9-oxabicyclo[6.1.0]nonane Chemical compound C1CCCCCC2OC21 MELPJGOMEMRMPL-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- DQZXOIPVJBKPAK-UHFFFAOYSA-L potassium;sodium;phosphono phosphate Chemical compound [Na+].[K+].OP(O)(=O)OP([O-])([O-])=O DQZXOIPVJBKPAK-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood 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
- C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
- C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—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
- F02B3/00—Engines characterised by air compression and subsequent fuel addition
- F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
Definitions
- the invention relates to fuels for gasoline and diesel engines containing an additive A) small amounts of alkoxylates obtained by alkoxylation of mono- or polyhydroxy compounds and B) small amounts of tri- or tetracarboxamides or -imides.
- By returning these so-called “blow-by gases" to the intake part or the air filter part of the oil mist that is created in the crankcase is brought back into the engine via the intake system and largely burned there, but they are noticeable Oil mist also deposits in the interior of the carburetor, in the intake ducts, on the intake valves and on the injection nozzles.
- High-performance carburettors are complex structures with very fine channels and bores and precisely calibrated nozzles for spraying and metering the fuel.
- the ratio of carbon monoxide to carbon dioxide in the exhaust gases is adversely affected, i.e. higher amounts of carbon monoxide in the exhaust gas occur in the case of dirty injection units or intake systems.
- the amount of additives (A) and (B) according to the invention added to petrol and diesel fuels is between 0.01 and 0.3% by weight, preferably between 0.005 and 0.15% by weight.
- the weight ratio of components (A) and (B) is usually between 5: 1 to 1: 3.
- Alkoxylates used are preferably butoxylates of mono- or polyhydroxy compounds or mixed alkoxylates using propylene / butylene mixed oxides.
- the proportion of butylene oxide or longer-chain alkylene oxide in the mixed alkoxylate is responsible for the oil solubility or oil compatibility of the alkoxide.
- the propylene oxide / butylene oxide ratio can be between 5:95 and 95: 5 parts by weight.
- Advantageous mixtures contain propylene oxide / butylene oxide in a ratio of 60:40 to 30:70. In principle, all butylene oxides, i.e.
- Butene-1, butene-2 or isobutene oxide or any mixtures of these oxides with one another or with propylene oxide are suitable for the preparation of the alkoxylates according to the invention.
- Effective alkoxylates are likewise obtained from mixtures of propylene oxide, butylene oxide and higher open-chain and cyclic alkene oxides or from the higher open-chain and cyclic alkene oxides alone.
- Examples include: pentene-1-oxide, decene-1-oxide, cyclopentene oxide, cyclohexene oxide and cyclooctene oxide and vinyl-cyclohexene oxides.
- Alcohols of the general formula come as mono- or polyhydroxy compounds R (OH) n , in which n is the numbers 1 to 4 and R is a C1-C20 straight-chain or preferably branched alkane, into consideration.
- Typical examples are butanol, isobutanol, 2-ethylhexanol, isononanol, isodekanol, isotridekanol, ethylene glycol, 1,2-propylene glycol, 1,3-propanediol, 1,2-butylene glycol, 1,4-butanediol, 1,5-pentanediol, neopentyl glycol , 1,6-hexanediol, trimethylolpropane, 1,2,4-butanediol and pentaerythritol.
- the alkoxylates are prepared by the methods of the prior art, i.e.
- a mono- or polyhydroxy compound is placed in a reactor together with the catalyst (e.g. sodium hydroxide, potassium hydroxide or alkali alcoholates) and gassed with alkylene oxides or alkylene oxide mixtures or reacted with liquid alkylene oxides with stirring at temperatures from 120 to 150 ° C.
- the catalyst e.g. sodium hydroxide, potassium hydroxide or alkali alcoholates
- any gaseous alkylene oxide which has not reacted is drawn off under vacuum and the crude alkoxylate is optionally washed with water largely free of alkali.
- the alkaline catalyst e.g.
- the alkoxylate when using potassium hydroxide, the alkoxylate can be washed with a sufficient amount of an aqueous solution of sodium pyrophosphate (Na2H2P4O7).
- sodium potassium pyrophosphate precipitates as an insoluble double salt and can be filtered off.
- alkoxylates to be used according to the invention it is not necessary to start from mixtures of the alkylene oxides in question in the case of mixed alkoxylates. It is also possible to react two or more alkylene oxides in succession with the mono- or polyhydroxy compound as the starting molecule. Alkoxylates, which are initially obtained by reacting mono- or polyhydroxy compounds only with a small amount of ethylene oxide (e.g. 1-5 mol ethylene oxide per hydroxyl group of the mono- or polyhydroxy compound), can also be obtained by subsequent reaction with a correspondingly large amount of higher alkylene oxides implement alkoxylates to be used according to the invention.
- ethylene oxide e.g. 1-5 mol ethylene oxide per hydroxyl group of the mono- or polyhydroxy compound
- Possible components (B) are, for example, reaction products of nitrogen-containing polycarboxylic acids with mono-, oligo- or polyamines or technical amine mixtures, such as are described, for example, as mixed components in EP-A-6527.
- the compounds according to (B) of the formula I are prepared by methods known per se, for example by reacting nitrilotriacetic acid or ethylenediaminetetraacetic acid with the amines or amine mixtures R-NH2 obtained at temperatures of 150 to 220 ° C usually 160 to 200 ° C.
- the amines are used in a molar ratio of 2: 1 (cyclic diimide) or in an amount of 3 moles of amine or amine mixture per mole of ethylenediaminetetraacetic acid (amine imide) or 2 moles per mole of nitriloacetic acid (amide imide) or To a small extent, additional amounts applied. In most cases, amidimides or imides are obtained in this way in addition to minor amounts of amides, ie substitution of all carbonyl groups by one amide residue.
- the procedure is such that the amine or amine mixture is placed in a stirred vessel under a nitrogen atmosphere and the nitriloacetic acid or ethylenediaminetetraacetic acid is introduced at approximately 80 ° C. and the mixture is stirred at 160 to 200 ° C. for 4 to 10 hours, at slowly reacting amines or amine mixtures also heated to a higher temperature until the acid number is less than 10.
- amines of the formula R-NH2 those with 7 to 18, preferably 8 to 14 carbon atoms are suitable. These amines can also have further amino groups, for example non-primary amino groups or alkoxy groups. Likewise, oxygen atoms can be present in the chain.
- alkyl radicals can be interrupted by nitrogen or oxygen atoms: 2-ethylhexylamine, n-dodecylamine, n-tridecylamine, n-pentadecylamine, stearylamine, 2-amino-5-dimethylaminopentane and 1- (2-ethylhexoxy) -propylamine- (3).
- Fuel additives using the alkoxylates (A) and the polycarboximides can additionally contain a number of other known active components, such as sterically hindered substituted phenols as antioxidants, dipropylene glycol or similarly designed glycols as antiicing additives to protect the carburetor from ice formation, corrosion inhibitors, metal deactivators, Demulsifiers and antistatic agents to increase the conductivity of the fuels.
- active components such as sterically hindered substituted phenols as antioxidants, dipropylene glycol or similarly designed glycols as antiicing additives to protect the carburetor from ice formation, corrosion inhibitors, metal deactivators, Demulsifiers and antistatic agents to increase the conductivity of the fuels.
- the results are evaluated as follows.
- the new inlet valves are cleaned or degreased with solvent before the test and weighed exactly to three decimal places. At the end of the test, the valves are removed.
- the stems or the valve tulips are assessed by checking the stickiness with finger pressure.
- the valves, including the stems are then swung twice in n-heptane for 5 seconds and dried in air by swirling.
- the valves are then mechanically freed from the combustion residues adhering to the underside of the tulip after clamping on the shafts in a horizontally mounted drilling machine with the help of a wood chip or sanding cloth with a grain size of 400 and then at three points behind exactly weighed the comma.
- the Ab Bearings of all 4 valves are averaged and the result is given in mg / valve.
- the carburettor is kept clean by evaluating the carburettor according to the CRC rating scale.
- Carburetor contamination with non-additive fuels generally gives a rating of 6.5 to 8.5. If effective carburetor-cleaning additives are present, the rating after the end of the test is between 8.0 and 10.0.
- the rating 10.0 corresponds to a completely clean carburetor.
- Table 2 contains test results with fuels without the use of fuel additives (Ex. 1 to 3), as well as results of engine test runs using the components of the combination to be used according to the invention.
- a Daimler-Benz M 102 electric engine was also used to check the cleanliness in the intake system.
- Test procedure is similar to the Opel Kadett test, the test conditions are shown in the following list: Engine: 4-cylinder injection engine, 2.3 l displacement, 100 KW Engine oil: RL 51 or SAE 15W / 40, API-SF / CC Running time: 40 to 150 hours
- Test program per cycle Stage 1: 30 s idling at 800 rpm
- Stage 2 1 min at 3000 rpm 18.4
- Stage 3 1 min at 1300 rpm 4.4 KW
- Stage 4 2 min at 1750 rpm 7.4 KW Oil temperature in the oil pan 90 ⁇ 3 ° C
- Coolant temperature (outlet) 89 ⁇ 3 ° C
- valves are evaluated using the same method as for the Opel Kadett engine. Runtimes longer than 40 hours can also be selected to tighten the test conditions.
- Table 3 shows some results for valve deposits of non-additive fuels in the Daimler-Benz M 102 electric motor. Each test run was carried out over a test period of 40 hours.
- An additive mixture of the following composition was used: 24 parts by weight component F in Table 1 60 parts by weight of alkoxylate B in Table 1 16 parts by weight a high-boiling aromatic solvent (solvent naphtha with a boiling point of approx. 160 ° C, mainly consisting of C9 + aromatics, such as commercial products Solvesso 150 or Shellsol AB)
- a high-boiling aromatic solvent solvent naphtha with a boiling point of approx. 160 ° C, mainly consisting of C9 + aromatics, such as commercial products Solvesso 150 or Shellsol AB
- Valve deposit result 0 mg / valve Carburetor rating: Rating 9.9
- the additive mixture was the same as that given in Example 14, but was tested in a Daimler-Benz M 102 E test engine.
- valve deposits are 0 mg / valve and the carburetor rating is 9.4.
- the engine is operated according to the same test cycle as the Daimler Benz M 102 electric motor.
- the clean-up effect for the intake valves is evaluated after 40, 80, 120 or 200 hours; the evaluation is carried out in the same way as for the Opel Kadett and Daimler-Benz engines.
- valve stickiness is checked visually.
- the cylinder head is stored in an inclined position of approx. 45-60 ° with the intake valves still inside.
- the inlet valves slip through their own weight in a very short time out of the valve guide.
- Adhesive valves as a result of unsuitable fuel additives can be recognized by the fact that the inlet valves do not slide out of the guide due to their own weight or can only be moved out by mechanical assistance.
- Test runs were carried out in the 1.6 t engine, type Opel Ascona, to test the valve stickiness. All tests were carried out over a period of 200 hours. This corresponds to a fuel consumption of approx. 2000 l and an approximate running distance of 4000-5000 km. The results are shown in Table 4.
- Test conditions for testing valve stickiness in practical driving tests Engine: Volkswagen, boxer engine, 1.9 l displacement, 44 KW Driving program: 10 km with max. 50 km / h 10 km with max. 60 km / h 10 min standstill
- the outside temperature during the night of the vehicle was between +3 and -3 ° C.
- the temperatures in the engine compartment were between +3 and + 8 ° C the next morning before the measurement.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
- Liquid Carbonaceous Fuels (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19873708338 DE3708338A1 (de) | 1987-03-14 | 1987-03-14 | Kraftstoffe, enthaltend geringe mengen alkoxylate und polycarbonsaeureimide |
DE3708338 | 1987-03-14 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0282845A1 true EP0282845A1 (fr) | 1988-09-21 |
EP0282845B1 EP0282845B1 (fr) | 1992-06-10 |
Family
ID=6323088
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP88103420A Expired - Lifetime EP0282845B1 (fr) | 1987-03-14 | 1988-03-05 | Combustibles contenant de petites quantités d'alcoxylate et d'imide d'acide polycarboxylique |
Country Status (4)
Country | Link |
---|---|
US (1) | US4844714A (fr) |
EP (1) | EP0282845B1 (fr) |
DE (2) | DE3708338A1 (fr) |
DK (1) | DK132288A (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0374461A1 (fr) * | 1988-11-17 | 1990-06-27 | BASF Aktiengesellschaft | Combustibles pour machines à combustion |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7204863B2 (en) * | 2001-12-11 | 2007-04-17 | Exxonmobil Research And Engineering Company | Gasoline additives for reducing the amount of internal combustion engine intake valve deposits and combustion chamber deposits |
US7226489B2 (en) | 2001-12-12 | 2007-06-05 | Exxonmobil Research And Engineering Company | Gasoline additives for reducing the amount of internal combustion engine intake valve deposits and combustion chamber deposits |
MY155314A (en) * | 2007-11-28 | 2015-09-30 | Shell Int Research | Gasoline compositions |
US10457884B2 (en) | 2013-11-18 | 2019-10-29 | Afton Chemical Corporation | Mixed detergent composition for intake valve deposit control |
US10273425B2 (en) * | 2017-03-13 | 2019-04-30 | Afton Chemical Corporation | Polyol carrier fluids and fuel compositions including polyol carrier fluids |
US11873461B1 (en) | 2022-09-22 | 2024-01-16 | Afton Chemical Corporation | Extreme pressure additives with improved copper corrosion |
US11884890B1 (en) | 2023-02-07 | 2024-01-30 | Afton Chemical Corporation | Gasoline additive composition for improved engine performance |
US11795412B1 (en) | 2023-03-03 | 2023-10-24 | Afton Chemical Corporation | Lubricating composition for industrial gear fluids |
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US2763537A (en) * | 1949-05-24 | 1956-09-18 | California Research Corp | Diesel fuel oil |
US2841479A (en) * | 1954-05-28 | 1958-07-01 | Dow Chemical Co | Glycerol triether lubricant compositions |
US2938777A (en) * | 1956-04-19 | 1960-05-31 | Tidewater Oil Company | Gasoline fuel composition |
US3030939A (en) * | 1958-07-10 | 1962-04-24 | Standard Oil Co | Method of operating spark-ignition combustion engine |
US3838992A (en) * | 1971-02-22 | 1974-10-01 | Universal Oil Prod Co | Synergistic anti-icing composition |
US3901665A (en) * | 1972-10-06 | 1975-08-26 | Du Pont | Multi-functional fuel additive compositions |
EP0006527A1 (fr) * | 1978-06-26 | 1980-01-09 | BASF Aktiengesellschaft | Carburants pour moteurs à carburateur contenant un mélange d'additifs |
EP0110003A2 (fr) * | 1982-12-01 | 1984-06-13 | The Dow Chemical Company | Additif anti-nébulisation pour fluides hydrocarbonés |
GB2143846A (en) * | 1983-07-25 | 1985-02-20 | Shell Int Research | A diesel fuel based on methanol and/or ethanol |
EP0144922A2 (fr) * | 1983-12-03 | 1985-06-19 | Mineralölwerke Wenzel und Weidmann Zweigniederlassung der Fuchs Mineralölwerke GmbH, Mannheim | Lubrifiant |
US4548616A (en) * | 1984-06-14 | 1985-10-22 | Texaco Inc. | Gasoline containing as additive poly(oxyethylene) poly(oxypropylene) poly(oxyethylene) polyol to reduce octane requirement increase |
EP0061895B1 (fr) * | 1981-03-31 | 1986-03-05 | Exxon Research And Engineering Company | Additif pour améliorer l'écoulement des carburants distillés et leurs concentrats |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US4659338A (en) * | 1985-08-16 | 1987-04-21 | The Lubrizol Corporation | Fuel compositions for lessening valve seat recession |
-
1987
- 1987-03-14 DE DE19873708338 patent/DE3708338A1/de not_active Withdrawn
-
1988
- 1988-03-04 US US07/164,492 patent/US4844714A/en not_active Expired - Fee Related
- 1988-03-05 DE DE8888103420T patent/DE3871828D1/de not_active Expired - Lifetime
- 1988-03-05 EP EP88103420A patent/EP0282845B1/fr not_active Expired - Lifetime
- 1988-03-11 DK DK132288A patent/DK132288A/da not_active Application Discontinuation
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2763537A (en) * | 1949-05-24 | 1956-09-18 | California Research Corp | Diesel fuel oil |
US2841479A (en) * | 1954-05-28 | 1958-07-01 | Dow Chemical Co | Glycerol triether lubricant compositions |
US2938777A (en) * | 1956-04-19 | 1960-05-31 | Tidewater Oil Company | Gasoline fuel composition |
US3030939A (en) * | 1958-07-10 | 1962-04-24 | Standard Oil Co | Method of operating spark-ignition combustion engine |
US3838992A (en) * | 1971-02-22 | 1974-10-01 | Universal Oil Prod Co | Synergistic anti-icing composition |
US3901665A (en) * | 1972-10-06 | 1975-08-26 | Du Pont | Multi-functional fuel additive compositions |
EP0006527A1 (fr) * | 1978-06-26 | 1980-01-09 | BASF Aktiengesellschaft | Carburants pour moteurs à carburateur contenant un mélange d'additifs |
EP0061895B1 (fr) * | 1981-03-31 | 1986-03-05 | Exxon Research And Engineering Company | Additif pour améliorer l'écoulement des carburants distillés et leurs concentrats |
EP0110003A2 (fr) * | 1982-12-01 | 1984-06-13 | The Dow Chemical Company | Additif anti-nébulisation pour fluides hydrocarbonés |
GB2143846A (en) * | 1983-07-25 | 1985-02-20 | Shell Int Research | A diesel fuel based on methanol and/or ethanol |
EP0144922A2 (fr) * | 1983-12-03 | 1985-06-19 | Mineralölwerke Wenzel und Weidmann Zweigniederlassung der Fuchs Mineralölwerke GmbH, Mannheim | Lubrifiant |
US4548616A (en) * | 1984-06-14 | 1985-10-22 | Texaco Inc. | Gasoline containing as additive poly(oxyethylene) poly(oxypropylene) poly(oxyethylene) polyol to reduce octane requirement increase |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0374461A1 (fr) * | 1988-11-17 | 1990-06-27 | BASF Aktiengesellschaft | Combustibles pour machines à combustion |
Also Published As
Publication number | Publication date |
---|---|
DK132288A (da) | 1988-09-15 |
DE3871828D1 (de) | 1992-07-16 |
US4844714A (en) | 1989-07-04 |
DE3708338A1 (de) | 1988-09-22 |
DK132288D0 (da) | 1988-03-11 |
EP0282845B1 (fr) | 1992-06-10 |
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