EP2479245A1 - Additifs de carburant et essence contenant les additifs - Google Patents
Additifs de carburant et essence contenant les additifs Download PDFInfo
- Publication number
- EP2479245A1 EP2479245A1 EP11196230A EP11196230A EP2479245A1 EP 2479245 A1 EP2479245 A1 EP 2479245A1 EP 11196230 A EP11196230 A EP 11196230A EP 11196230 A EP11196230 A EP 11196230A EP 2479245 A1 EP2479245 A1 EP 2479245A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- gasoline
- concentrate
- composition
- fuel
- polyamine
- 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
- 239000000654 additive Substances 0.000 title claims abstract description 44
- 239000002816 fuel additive Substances 0.000 title description 2
- 239000000446 fuel Substances 0.000 claims abstract description 62
- 239000000203 mixture Substances 0.000 claims abstract description 56
- 239000012141 concentrate Substances 0.000 claims abstract description 38
- 229920000768 polyamine Polymers 0.000 claims abstract description 28
- 239000003254 gasoline additive Substances 0.000 claims abstract description 22
- 230000000996 additive effect Effects 0.000 claims abstract description 21
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 18
- 229940014800 succinic anhydride Drugs 0.000 claims abstract description 14
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims abstract description 13
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000005431 greenhouse gas Substances 0.000 claims abstract description 7
- 238000002347 injection Methods 0.000 claims description 16
- 239000007924 injection Substances 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 11
- 229920002367 Polyisobutene Polymers 0.000 claims description 10
- 239000003599 detergent Substances 0.000 claims description 10
- 239000012530 fluid Substances 0.000 claims description 10
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- ALMADHLGAHFBJQ-UHFFFAOYSA-N 2-aminoethanol;3-piperazin-1-ylpropan-1-amine Chemical compound NCCO.NCCCN1CCNCC1 ALMADHLGAHFBJQ-UHFFFAOYSA-N 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims description 2
- XMMDVXFQGOEOKH-UHFFFAOYSA-N n'-dodecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCNCCCN XMMDVXFQGOEOKH-UHFFFAOYSA-N 0.000 claims description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 2
- WJDXXMQCSSBFNS-UHFFFAOYSA-N ethene oxolane-2,5-dione Chemical group C=C.C=C.C=C.C=C.C1(CCC(=O)O1)=O WJDXXMQCSSBFNS-UHFFFAOYSA-N 0.000 claims 1
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 16
- 239000000126 substance Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- 239000000306 component Substances 0.000 description 12
- -1 hydrocarbyl phenol Chemical compound 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 5
- 238000002485 combustion reaction Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 239000010705 motor oil Substances 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229960002317 succinimide Drugs 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 230000009102 absorption Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002272 engine oil additive Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 230000000153 supplemental effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000001706 oxygenating effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
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
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development
-
- 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
- C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
-
- 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
-
- 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
- C10L1/234—Macromolecular compounds
- C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
-
- 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
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/18—Use of additives to fuels or fires for particular purposes use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/16—Hydrocarbons
- C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
-
- 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
- C10L2200/00—Components of fuel compositions
- C10L2200/04—Organic compounds
- C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
- C10L2200/0415—Light distillates, e.g. LPG, naphtha
- C10L2200/0423—Gasoline
-
- 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
- C10L2270/00—Specifically adapted fuels
- C10L2270/02—Specifically adapted fuels for internal combustion engines
- C10L2270/023—Specifically adapted fuels for internal combustion engines for gasoline engines
Definitions
- the present disclosure relates in one embodiment a gasoline additive concentrate comprising the product of combining a 1,8-naphthalic anhydride and a reaction product of a hydrocarbyl-substituted succinic anhydride with a polyamine.
- a fuel composition comprising the gasoline concentrate is also disclosed.
- a method for reducing greenhouse gas emissions comprising adding to a gasoline the disclosed additive and combusting the fuel composition in an engine.
- This invention materially enhances the quality of the environment by contributing to the restoration or maintenance of the basic life-sustaining natural elements.
- this invention materially contributes to greenhouse gas emission reduction.
- Gasoline fuel requires additives to maintain optimal performance for machineries that use gasoline fuel.
- Common fuel additives include a reaction product of hydrocarbyl phenol with formaldehyde and amines, which are generally known as Mannich base products or dispersant/detergents.
- Additives could also include hydrocarbons and alkyl polyols, which are commonly known as carrier fluids.
- One critical performance requirement of machinery such as automobile engines is maintaining a clean fuel delivery system. Additives mentioned above could mitigate the problem of fouling fuel delivery system. Yet there is always a need for additives that could afford better performance.
- DIG direct injection gasoline
- the additives which work well as detergents in multi-port injection engines will not necessarily work well in DIG engines, and as such additional detergents prepared especially for DIG engines may be required as a "top-treat" type additive or as an after-market fuel supplement.
- HSA hydrocarbyl succinic anhydride
- PAM polyamines
- the ratio of the naphthalic anhydride capping agent to the PIBSA was 0.60:1 and this compound was used in an engine oil containing known engine oil additives.
- engine oils contain additives that are not suitable for use in fuels, such as zinc dialkyldithiophosphate. Further, it is known to further treat with a cyclic carbonate, which is not required by the present invention.
- Figure 1 is a graph of the Long Term Fuel Trim (LTFT) of a conventional additized gasoline fuel comprising Mannich and carrier fluid.
- LTFT Long Term Fuel Trim
- Figure 2 is a graph of the LTFT for various comparative compositions.
- Figure 3 is a graph of the LTFT of various inventive compositions.
- a gasoline additive concentrate comprising the product of combining (a) a 1,8-naphthalic anhydride; and (b) a reaction product of a hydrocarbyl-substituted succinic anhydride with a polyamine.
- a method to reduce the amount of deposits in direct injection gasoline engines comprising adding to a gasoline to be combusted in the direct injection gasoline engine a gasoline additive concentrate to form a gasoline composition, then combusting the gasoline composition.
- a method to reduce greenhouse gas emissions comprising adding to a gasoline to be combusted in the direct injection gasoline engine a gasoline additive concentrate to form a gasoline composition, then combusting the gasoline composition.
- the present disclosure relates in one embodiment to a gasoline additive concentrate comprising a product of combining (a) a 1,8-naphthalic anhydride; and (b) a reaction product of a hydrocarbyl-substituted succinic anhydride with a polyamine. It is believed, without being limited to any particular theory, that the reaction product forms an imide.
- the molar ratio of (a) to (b) is about 1:1, for example ranging from about 0.95:0.05 to about 0.05:0.95, and as a further example from about 0.8:0.2 to about 0.2:0.8. In an aspect, the molar ratio is from about 0.5:1 to about 1:0.5.
- the prior art teaches using a reaction product of PIBSA and various amines in fuel and lubricant compositions, but an improvement herein lies in top treating a gasoline composition with a gasoline additive concentrate comprising a product of combining (a) a 1,8-naphthalic anhydride; and (b) a reaction product of a hydrocarbyl-substituted succinic anhydride with a polyamine.
- reaction products obtained by reacting a hydrocarbyl-substituted succinic anhydride, acid, acid-ester or lower alkyl ester with an amine containing at least two amino groups, such as a polyamine.
- a hydrocarbyl-substituted succinic anhydride may be prepared readily by heating a mixture of olefin and maleic anhydride to about 180-220° C.
- the hydrocarbyl is, in an embodiment, a polymer or copolymer of a lower monoolefin such as ethylene, propylene, isobutene and the like.
- the source of alkenyl group is from polyisobutene having a molecular weight up to 10,000 or higher.
- the alkenyl is a polyisobutene group having a molecular weight of about 200-5,000, for example about 500-2,000, and as a further example form about 700-1000.
- the polyisobutene group has a molecular weight less than about 1000, such as about 950.
- the hydrocarbyl substituent of the hydrocarbyl-substituted succinic anhydride is a polyisobutylene.
- Amines which may be employed include any that have at least two amino groups which can react to form an imide group.
- a few representative examples are: N-dodecyl propanediamine, N-aminopropyl piperazine ethanolamine, N-ethanol ethylene diamine and the like.
- Preferred amines include the alkylene polyamines such as propylene diamine, dipropylene triamine, di-(1,2-butylene)-triamine, tetra-(1,2-propylene)pentaamine.
- the amines are the ethylene polyamines that have the formula H 2 N(CH 2 CH 2 NH) n H wherein n is an integer from one to ten.
- These ethylene polyamines include ethylene diamine, diethylene triamine, triethylene tetraamine, tetraethylene pentaamine, pentaethylene hexaamine, and the like, including mixtures thereof in which case n is the average value of the mixture.
- These ethylene polyamines have a primary amine group at each end so can form mono-alkenylsuccinimides and bis-alkenylsuccinimides.
- a heavy polyamine can also be used.
- the polyamine is tetraethylene pentamine.
- the molar ratio of the hydrocarbyl-substituted succinic anhydride to the polyamine is about 1:1, but may include other ratios such as 5:1-1:5, and ranges in between.
- reaction product (b) for use in the present invention can also include the products of reaction of a polyethylenepolyamine, e.g. triethylene tetramine or tetraethylene pentamine, with a hydrocarbon substituted carboxylic acid or anhydride made by reaction of a polyolefin, such as polyisobutene, having a molecular weight of 250 to 5,000, for example 500 to 2000, and as a further example less than about 1000, with an unsaturated polycarboxylic acid or anhydride, e.g. maleic anhydride.
- a polyethylenepolyamine e.g. triethylene tetramine or tetraethylene pentamine
- a hydrocarbon substituted carboxylic acid or anhydride made by reaction of a polyolefin, such as polyisobutene, having a molecular weight of 250 to 5,000, for example 500 to 2000, and as a further example less than about 1000
- an unsaturated polycarboxylic acid or anhydride
- the gasoline additive concentrate can be used to top treat a gasoline composition in any amount effective to reduce intake valve deposits.
- the additive concentrate can be used in a gasoline composition in an amount of 0.1 ptb to about 10 ptb, such as 0.4 ptb to about 7 ptb, as a further example 1 ptb to about 6 ptb, and as a further example, 2 ptb to about 5.5 ptb.
- the fuel compositions disclosed herein comprise a minor amount of the disclosed gasoline additive concentrate and a major amount of a hydrocarbon fuel in the gasoline boiling range.
- minor amount means less than about 50% by weight of the total weight of the fuel composition.
- major amount means greater than or equal to about 50% by weight of the total weight of the fuel composition.
- the fuel utilized in the practice of this disclosure can be traditional blends or mixtures of hydrocarbons in the gasoline boiling range, or they can contain oxygenated blending components such as alcohols and/or ethers having suitable boiling temperatures and appropriate fuel solubility, such as methanol, ethanol, methyl tert-butyl ether (MTBE), ethyl tert-butyl ether (ETBE), tert-amyl methyl ether (TAME), and mixed oxygen-containing products formed by "oxygenating" gasolines and/or olefinic hydrocarbons falling in the gasoline boiling range.
- oxygenated blending components such as alcohols and/or ethers having suitable boiling temperatures and appropriate fuel solubility, such as methanol, ethanol, methyl tert-butyl ether (MTBE), ethyl tert-butyl ether (ETBE), tert-amyl methyl ether (TAME), and mixed oxygen-containing products formed by "oxygenating" gasolines and/or olefini
- gasolines including the so-called reformulated gasolines which are designed to satisfy various governmental regulations concerning composition of the base fuel itself, componentry used in the fuel, performance criteria, toxicological considerations and/or environmental considerations.
- the amounts of oxygenated components, detergents, antioxidants, demulsifiers, and the like that are used in the fuels can thus be varied to satisfy any applicable government regulations, provided that in so doing the amounts used do not materially impair the improved ignition performance made possible by the practice of this invention.
- the gasoline additive concentrate is employed in amounts sufficient to reduce or eliminate injector deposits.
- the fuels will comprise minor amounts of the gasoline additive, i.e., the reaction product of (a) an aromatic anhydride or derivative thereof, and (b) a hydrocarbyl amine or alcohol proportioned so as to prevent or reduce formation of engine deposits, especially fuel injector deposits, and most especially intake valve deposits.
- the gasoline additive concentrate or fuel composition further comprises other additives, such as a Mannich base detergent such as those disclosed in U.S. Patent No. 7,491,248 .
- a Mannich base detergent such as those disclosed in U.S. Patent No. 7,491,248 .
- the Mannich base detergents useful in embodiments of the present invention are the reaction products of an alkyl-substituted hydroxy aromatic compound, aldehydes and amines.
- the alkyl-substituted hydroxyaromatic compound, aldehydes and amines used in making the Mannich reaction products of the present invention may be any such compounds known and applied in the art, such as those disclosed in U.S. Patent No. 7,491,248 .
- the gasoline additive concentrate or fuel composition further comprises a liquid carrier or induction aid such as those disclosed in U.S. Patent No. 7,491,248 .
- a liquid carrier or induction aid such as those disclosed in U.S. Patent No. 7,491,248 .
- Such carriers can be of various types, such as for example liquid poly-alpha-olefin oligomers, mineral oils, liquid poly(oxyalkylene) compounds, liquid alcohols or polyols, polyalkenes, liquid esters, and similar liquid carriers. Mixtures of two or more such carriers can be employed.
- Liquid carriers can include but is not limited to 1) a mineral oil or a blend of mineral oils that have a viscosity index of less than about 120, 2) one or more poly-alpha-olefin oligomers, 3) one or more poly(oxyalkylene) compounds having an average molecular weight in the range of about 500 to about 3000, 4) polyalkenes, 5) polyalkyl-substituted hydroxyaromatic compounds or 6) mixtures thereof.
- the fuel compositions of the present invention may contain supplemental additives in addition to the detergent(s), and carrier fluids described above.
- Said supplemental additives include additional dispersants/detergents, antioxidants, carrier fluids, metal deactivators, dyes, markers, corrosion inhibitors, biocides, antistatic additives, drag reducing agents, demulsifiers, dehazers, anti-icing additives, antiknock additives, anti-valve-seat recession additives, lubricity additives and combustion improvers.
- the additives used in formulating the preferred fuels of the present invention can be blended into the base fuel individually or in various sub-combinations. However, it is preferable to blend all of the components concurrently using an additive concentrate as this takes advantage of the mutual compatibility afforded by the combination of ingredients when in the form of an additive concentrate. Also use of a concentrate reduces blending time and lessens the possibility of blending errors.
- aspects of the present invention include a method to reduce the amount of deposits in direct injection gasoline engines, the method comprising adding to a gasoline to be combusted in the direct injection gasoline engine a gasoline additive concentrate to form a gasoline composition, then combusting the gasoline composition.
- a method to reduce greenhouse gas emissions comprising adding to a gasoline to be combusted in the direct injection gasoline engine a gasoline additive concentrate to form a gasoline composition, then combusting the gasoline composition.
- PIBSA polyisobutylenesuccnic anhydride
- PAM polyamine
- TEPA tetraethylenepentamine
- 1,8-naphthalic anhydride (27.7g, 0.14 mol) was added to a PIBSI (950 MW PIB), a reaction product of PIBSA with TEPA in about 1 to 1 molar ratio with a method disclosed in US 5752989 (180.9g, 0.164 mol).
- Solvent aromatic 150 (128g) was added. The mixture was heated to 175° C for 1.5 hr under a slow nitrogen sweep. It was then filtered via celite 512 to afford product as a brown oil. The FTIR peak absorptions were at 1702 cm -1 and 1664 cm -1 .
- DIG test An engine test measuring fuel injector deposit is performed following a procedure disclosed in Society of Automotive Engineer (SAE) International publication 2009-01-2641"Test and Control of Fuel Injector Deposits in Direct Injected Spark Ignition Vehicles".
- SAE Society of Automotive Engineer
- a mathematical value of Long Term Fuel Trim (LTFT) is used to gauge the ability of the additive to keep deposits from accumulating in the injectors, or keep the injector clean. The higher the LTFT, the more deposit in the injectors, the less effective the additive is in keeping the injector clean.
- a 2008 General Motors Pontiac Solstice GXP equipped with a DISI 2.0 liter turbocharged 1-4 was used in the test. Table 1. Injector Cleanliness as determined by Long Term Fuel Trim (LTFT).
- Comparative example 1 DIG test with conventional additized gasoline fuel containing Mannich and carrier fluid. No additional additive was used. The treat rate of the Mannich and carrier fluid was 38.4 pound additive per thousand barrel of gasoline fuel (ptb). The LTFT was measured at 17.2%. Comparative example 2 - PIBSI from Example A was used at a treat rate of 1.5 ptb. The LTFT was measured at 11.7%.
- Comparative example 3 Same as comparative example 2 except that 2.0 ptb of active PIBSI from example A was mixed into the fuel. The LTFT was measured at 4.7%.
- Inventive example 4 - 2 ptb of active material from Example B was used.
- the LTFT was measured at 0.8%.
- inventive example 5 Same as inventive example 4 except that the amount of additive was reduced to 1 ptb.
- the LTFT was measured at 2.4%.
- inventive compositions 4-5 have a smaller LTFT, i.e., cleaner injectors, as compared to comparative composition 1-3. This demonstrates the unexpected and superior performance of the PIBSA-TEPA NA in a fuel composition.
- Ford 2.3-IVD test Another test (a modified ASTM D620) was conducted to determine the intake valve deposit-forming tendency of gasoline using a Ford 2.3-Liter engine (short for Ford 2.3-IVD test). The additive was mixed into gasoline to control the amount of deposit in the intake valve. For this test, a 1994 Ford 2.3-L dual spark plug engine on a dynamometer test stand was used. The test cycle consists of:
- compositions in Table 2 were run in a test cycle CRC for 100 hours.
- Inventive composition 10 exhibited a reduction in intake valve deposits as compared to Comparative compositions 8-9.
- the additives in tests 8 and 9 were 28 ptb of a mixture of a typical Mannich base and a typical carrier fluid.
- Comparative example 8 Ford 2.3-IVD test with conventional additive Mannich and carrier fluid.
- the average intake valve deposit (IVD) was at 118.8 mg.
- Inventive example 10 Same as comparative example 8 except that material from example B was added at a treat rate of 2.0 ptb. The average IVD was 72.1 mg. The less the amount of deposit, the more effective the additive was in reducing intake valve deposit. This also demonstrates the unexpected and superior performance of the PIBSA-TEPA NA in a fuel composition.
- reactants and components referred to by chemical name anywhere in the specification or claims hereof, whether referred to in the singular or plural, are identified as they exist prior to coming into contact with another substance referred to by chemical name or chemical type (e.g., base fuel, solvent, etc.). It matters not what chemical changes, transformations and/or reactions, if any, take place in the resulting mixture or solution or reaction medium as such changes, transformations and/or reactions are the natural result of bringing the specified reactants and/or components together under the conditions called for pursuant to this disclosure.
- the reactants and components are identified as ingredients to be brought together either in performing a desired chemical reaction (such as a Mannich condensation reaction) or in forming a desired composition (such as an additive concentrate or additized fuel blend).
- the additive components can be added or blended into or with the base fuels individually per se and/or as components used in forming preformed additive combinations and/or sub-combinations. Accordingly, even though the claims hereinafter may refer to substances, components and/or ingredients in the present tense ("comprises”, “is”, etc.), the reference is to the substance, components or ingredient as it existed at the time just before it was first blended or mixed with one or more other substances, components and/or ingredients in accordance with the present disclosure. The fact that the substance, components or ingredient may have lost its original identity through a chemical reaction or transformation during the course of such blending or mixing operations is thus wholly immaterial for an accurate understanding and appreciation of this disclosure and the claims thereof.
- fuel-soluble or “gasoline-soluble” means that the substance under discussion should be sufficiently soluble at 20° C in the base fuel selected for use to reach at least the minimum concentration required to enable the substance to serve its intended function.
- the substance will have a substantially greater solubility in the base fuel than this.
- the substance need not dissolve in the base fuel in all proportions.
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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Application Number | Priority Date | Filing Date | Title |
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US13/009,289 US20120180382A1 (en) | 2011-01-19 | 2011-01-19 | Fuel Additives and Gasoline Containing the Additives |
Publications (2)
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EP2479245A1 true EP2479245A1 (fr) | 2012-07-25 |
EP2479245B1 EP2479245B1 (fr) | 2015-05-06 |
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EP20110196230 Active EP2479245B1 (fr) | 2011-01-19 | 2011-12-30 | Concentré additif de carburant et essence contenant le concentré |
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US (1) | US20120180382A1 (fr) |
EP (1) | EP2479245B1 (fr) |
CN (1) | CN102604696B (fr) |
BR (1) | BR102012001058B1 (fr) |
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US9068135B1 (en) * | 2014-02-26 | 2015-06-30 | Afton Chemical Corporation | Lubricating oil composition and additive therefor having improved piston deposit control and emulsion stability |
US20180016515A1 (en) | 2016-07-14 | 2018-01-18 | Afton Chemical Corporation | Dispersant Viscosity Index Improver-Containing Lubricant Compositions and Methods of Use Thereof |
CN108179041A (zh) * | 2018-01-16 | 2018-06-19 | 山东吉利达能源科技有限公司 | 一种高效减排国v汽油品质提升剂 |
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US5752989A (en) | 1996-11-21 | 1998-05-19 | Ethyl Corporation | Diesel fuel and dispersant compositions and methods for making and using same |
EP1518918A1 (fr) * | 2003-09-25 | 2005-03-30 | Afton Chemical Corporation | Compositions de combustibles et méthodes les utilisant. |
US20100160192A1 (en) * | 2008-12-22 | 2010-06-24 | Chevron Oronite LLC | lubricating oil additive composition and method of making the same |
US20100160194A1 (en) * | 2008-12-22 | 2010-06-24 | Chevron Oronite LLC | Post-treated additive composition and method of making the same |
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US5069684A (en) * | 1989-12-18 | 1991-12-03 | Mobil Oil Corporation | Fuel and lube additives from polyether derivatives of polyamine alkenyl succinimides |
GB9207383D0 (en) * | 1992-04-03 | 1992-05-13 | Ass Octel | Multi-functional gasoline detergent compositions |
-
2011
- 2011-01-19 US US13/009,289 patent/US20120180382A1/en not_active Abandoned
- 2011-12-30 EP EP20110196230 patent/EP2479245B1/fr active Active
-
2012
- 2012-01-16 BR BR102012001058-5A patent/BR102012001058B1/pt active IP Right Grant
- 2012-01-18 CN CN201210015108.9A patent/CN102604696B/zh active Active
Patent Citations (13)
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US3172892A (en) | 1959-03-30 | 1965-03-09 | Reaction product of high molecular weight succinic acids and succinic anhydrides with an ethylene poly- amine | |
US3219666A (en) | 1959-03-30 | 1965-11-23 | Derivatives of succinic acids and nitrogen compounds | |
US3202678A (en) | 1959-08-24 | 1965-08-24 | California Research Corp | Alkenyl succinimides of tetraethylene pentamine |
US3254025A (en) | 1961-08-18 | 1966-05-31 | Lubrizol Corp | Boron-containing acylated amine and lubricating compositions containing the same |
US3216936A (en) | 1964-03-02 | 1965-11-09 | Lubrizol Corp | Process of preparing lubricant additives |
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US5752989A (en) | 1996-11-21 | 1998-05-19 | Ethyl Corporation | Diesel fuel and dispersant compositions and methods for making and using same |
EP1518918A1 (fr) * | 2003-09-25 | 2005-03-30 | Afton Chemical Corporation | Compositions de combustibles et méthodes les utilisant. |
US7491248B2 (en) | 2003-09-25 | 2009-02-17 | Afton Chemical Corporation | Fuels compositions and methods for using same |
US20100160192A1 (en) * | 2008-12-22 | 2010-06-24 | Chevron Oronite LLC | lubricating oil additive composition and method of making the same |
US20100160194A1 (en) * | 2008-12-22 | 2010-06-24 | Chevron Oronite LLC | Post-treated additive composition and method of making the same |
Also Published As
Publication number | Publication date |
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BR102012001058B1 (pt) | 2019-04-16 |
EP2479245B1 (fr) | 2015-05-06 |
CN102604696A (zh) | 2012-07-25 |
BR102012001058A2 (pt) | 2013-07-02 |
US20120180382A1 (en) | 2012-07-19 |
CN102604696B (zh) | 2015-01-14 |
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