AU2022366282A1 - Polyamide fuel additives - Google Patents
Polyamide fuel additives Download PDFInfo
- Publication number
- AU2022366282A1 AU2022366282A1 AU2022366282A AU2022366282A AU2022366282A1 AU 2022366282 A1 AU2022366282 A1 AU 2022366282A1 AU 2022366282 A AU2022366282 A AU 2022366282A AU 2022366282 A AU2022366282 A AU 2022366282A AU 2022366282 A1 AU2022366282 A1 AU 2022366282A1
- Authority
- AU
- Australia
- Prior art keywords
- acid
- aminoethyl
- piperazine
- polyamine
- fuel
- 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.)
- Pending
Links
- 239000002816 fuel additive Substances 0.000 title claims description 12
- 239000004952 Polyamide Substances 0.000 title description 14
- 229920002647 polyamide Polymers 0.000 title description 14
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 239000000446 fuel Substances 0.000 claims abstract description 40
- 229920000768 polyamine Polymers 0.000 claims abstract description 33
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 30
- 239000000194 fatty acid Substances 0.000 claims abstract description 30
- 229930195729 fatty acid Natural products 0.000 claims abstract description 30
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000003502 gasoline Substances 0.000 claims abstract description 15
- 238000005260 corrosion Methods 0.000 claims abstract description 11
- 230000007797 corrosion Effects 0.000 claims abstract description 11
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 12
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 11
- -1 aliphatic fatty acid Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 9
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 claims description 6
- OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 claims description 6
- DIVCBWJKVSFZKJ-UHFFFAOYSA-N 4-methyl-hexanoic acid Chemical compound CCC(C)CCC(O)=O DIVCBWJKVSFZKJ-UHFFFAOYSA-N 0.000 claims description 6
- YMUHUYBRWUUAJF-UHFFFAOYSA-N 5-cyclohexylpentanoic acid Chemical compound OC(=O)CCCCC1CCCCC1 YMUHUYBRWUUAJF-UHFFFAOYSA-N 0.000 claims description 6
- MHPUGCYGQWGLJL-UHFFFAOYSA-N 5-methyl-hexanoic acid Chemical compound CC(C)CCCC(O)=O MHPUGCYGQWGLJL-UHFFFAOYSA-N 0.000 claims description 6
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 claims description 6
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical group NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 6
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims description 6
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 6
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 6
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims description 6
- SIOLDWZBFABPJU-UHFFFAOYSA-N isotridecanoic acid Chemical compound CC(C)CCCCCCCCCC(O)=O SIOLDWZBFABPJU-UHFFFAOYSA-N 0.000 claims description 6
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 6
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 claims description 6
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 5
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 3
- 239000001131 (4R)-4-methylnonanoic acid Substances 0.000 claims description 3
- 239000001706 (4R)-4-methyloctanoic acid Substances 0.000 claims description 3
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 3
- ZONJATNKKGGVSU-UHFFFAOYSA-N 14-methylpentadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCC(O)=O ZONJATNKKGGVSU-UHFFFAOYSA-N 0.000 claims description 3
- OCOCFNMFLNFNIA-ZSCHJXSPSA-N 2-(1-benzylindazol-3-yl)oxyacetic acid;(2s)-2,6-diaminohexanoic acid Chemical compound [NH3+]CCCC[C@H]([NH3+])C([O-])=O.C12=CC=CC=C2C(OCC(=O)[O-])=NN1CC1=CC=CC=C1 OCOCFNMFLNFNIA-ZSCHJXSPSA-N 0.000 claims description 3
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 claims description 3
- PAOXFRSJRCGJLV-UHFFFAOYSA-N 2-[4-(2-aminoethyl)piperazin-1-yl]ethanamine Chemical compound NCCN1CCN(CCN)CC1 PAOXFRSJRCGJLV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
- OARDBPIZDHVTCK-UHFFFAOYSA-N 2-butyloctanoic acid Chemical compound CCCCCCC(C(O)=O)CCCC OARDBPIZDHVTCK-UHFFFAOYSA-N 0.000 claims description 3
- CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 claims description 3
- MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical compound CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 claims description 3
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 claims description 3
- WQTZCQIRCYSUBQ-UHFFFAOYSA-N 4-Methylnonanoic acid Chemical compound CCCCCC(C)CCC(O)=O WQTZCQIRCYSUBQ-UHFFFAOYSA-N 0.000 claims description 3
- LEGGANXCVQPIAI-UHFFFAOYSA-N 4-methyl-octanoic acid Chemical compound CCCCC(C)CCC(O)=O LEGGANXCVQPIAI-UHFFFAOYSA-N 0.000 claims description 3
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims description 3
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 claims description 3
- 235000021357 Behenic acid Nutrition 0.000 claims description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005639 Lauric acid Substances 0.000 claims description 3
- 235000021314 Palmitic acid Nutrition 0.000 claims description 3
- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- ZRYCZAWRXHAAPZ-UHFFFAOYSA-N alpha,alpha-dimethyl valeric acid Chemical compound CCCC(C)(C)C(O)=O ZRYCZAWRXHAAPZ-UHFFFAOYSA-N 0.000 claims description 3
- 229940116226 behenic acid Drugs 0.000 claims description 3
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 3
- HJZLEGIHUQOJBA-UHFFFAOYSA-N cyclohexane propionic acid Chemical compound OC(=O)CCC1CCCCC1 HJZLEGIHUQOJBA-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- JMOLZNNXZPAGBH-UHFFFAOYSA-N hexyldecanoic acid Chemical compound CCCCCCCCC(C(O)=O)CCCCCC JMOLZNNXZPAGBH-UHFFFAOYSA-N 0.000 claims description 3
- 229950004531 hexyldecanoic acid Drugs 0.000 claims description 3
- WBIWIXJUBVWKLS-UHFFFAOYSA-N n'-(2-piperazin-1-ylethyl)ethane-1,2-diamine Chemical compound NCCNCCN1CCNCC1 WBIWIXJUBVWKLS-UHFFFAOYSA-N 0.000 claims description 3
- LPOUQGUYVMSQOH-UHFFFAOYSA-N n'-[2-(2-piperazin-1-ylethylamino)ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCN1CCNCC1 LPOUQGUYVMSQOH-UHFFFAOYSA-N 0.000 claims description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 239000008117 stearic acid Substances 0.000 claims description 3
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 3
- 229960000604 valproic acid Drugs 0.000 claims description 3
- 239000000654 additive Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000002485 combustion reaction Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000012530 fluid Substances 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 6
- 239000003607 modifier Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 238000009472 formulation Methods 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 239000010687 lubricating oil Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 3
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229960001124 trientine Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 description 1
- 239000004953 Aliphatic polyamide Substances 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 229920002323 Silicone foam Polymers 0.000 description 1
- 235000021322 Vaccenic acid Nutrition 0.000 description 1
- UWHZIFQPPBDJPM-FPLPWBNLSA-M Vaccenic acid Natural products CCCCCC\C=C/CCCCCCCCCC([O-])=O UWHZIFQPPBDJPM-FPLPWBNLSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229920003231 aliphatic polyamide Polymers 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 239000006079 antiknock agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- OYHQOLUKZRVURQ-AVQMFFATSA-N linoelaidic acid Chemical compound CCCCC\C=C\C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-AVQMFFATSA-N 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- NNNVXFKZMRGJPM-KHPPLWFESA-N sapienic acid Chemical compound CCCCCCCCC\C=C/CCCCC(O)=O NNNVXFKZMRGJPM-KHPPLWFESA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000013514 silicone foam Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- 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
- C10L1/2381—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds polyamides; polyamide-esters; polyurethane, polyureas
-
- 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
- C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
-
- 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
- C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
-
- 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
- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
Abstract
Method for preventing or reducing corrosion or wear in gasoline engine is provided. The step of the method includes supplying a fuel composition comprising a reaction product of fatty acid and polyamine.
Description
POLYAMIDE FUEL ADDITIVES
TECHNICAL FIELD
[001] This disclosure relates to fuel additive compositions and fuel compositions. More specifically, this disclosure relates to long-chain aliphatic polyamide compounds that can prevent corrosion/rust while providing anti- wear/friction protection.
BACKGROUND
[002] There has been considerable effort in recent years to improve the fuel economy of motor vehicles. In general, the efficiency of automotive engines is greatly enhanced by the presence of effective lubrication, particularly at the interface of moving parts that are prone to high friction and excessive wear. Thus, one approach for improving fuel economy has been to develop lubricants and lubricating oil additives that reduce engine friction and thus reduce energy requirements.
[003] Some of these efforts have focused on friction modifiers which are known lubricating oil additives that can reduce boundary friction by adsorbing or reacting on metal surfaces to form thin low-shear-strength films.
[004] Friction modifiers have been used in limited slip gear oils, automatic transmission fluids, slideway lubricants and multipurpose tractor fluids. In particular, with the desire for increased fuel economy, friction modifiers have been added to automotive crankcase lubricants. These friction modifiers generally operate at boundary layer conditions at temperatures where anti-wear and extreme pressure additives are not yet reactive by forming a thin mono-molecular layers of physically adsorbed polar oil-soluble products or reaction layers which exhibit a significantly lower friction compared to typical anti-wear or extreme pressure agents. However, under more severe conditions and in mixed lubrication regime these friction modifiers are added with an anti-wear or extreme pressure agent.
[005] The most common type of anti-wear or extreme pressure agent is a zinc dialkyl dithiophosphate (ZnDTP or ZDDP). ZDDP limit wear by forming a thick protective tribofilm on rubbing surfaces. Although ZDDP has been widely used in motor vehicles for many decades, some recent studies have shown that phosphorus- based anti-wear films can cause significant increase in friction in thin film, high- pressure, lubricated contacts. This, in turn, can have a negative effect on fuel efficiency.
[006] While reducing friction with lubricant additives has been important, there is potential to further improve fuel efficiency with fuel additives. Since the conditions of an internal combustion chamber are substantially different from those in a crankcase, it is not a given that a particular additive or class of additives that has provided performance benefits in a lubricating oil will provide similar benefits in fuel. Thus, there is a need to develop fuel additives that can reduce friction and/or improve fuel economy.
DESCRIPTION OF FIGURE
[007] FIG. 1 is described in the Example section.
SUMMARY OF THE INVENTION
[008] In one aspect, there is provided a method for preventing or reducing corrosion or wear in gasoline engine by supplying a fuel composition comprising a reaction product of fatty acid and polyamine.
[009] In another aspect, there is provided a method for preventing or reducing corrosion or wear in gasoline engine while providing anti-wear or friction protection by supplying a fuel composition comprising a fuel additive comprising a reaction product of fatty acid and polyamine.
DETAILED DESCRIPTION
Introduction
[010] In this specification, the following words and expressions, if and when used, have the meanings ascribed below.
[011] "Gasoline" or "gasoline boiling range components" refers to a composition containing at least predominantly C4-C12 hydrocarbons. In one embodiment, gasoline or gasoline boiling range components is further defined to refer to a composition containing at least predominantly C4-C12 hydrocarbons and further having a boiling range of from about 37.8 °C (100°F) to about 204° C (400 °F). In an alternative embodiment, gasoline or gasoline boiling range components is defined to refer to a composition containing at least predominantly C4-C12 hydrocarbons, having a boiling range of from about 37.8 °C (100 °F) to about 204 °C (400 °F), and further defined to meet ASTM D4814.
[012] The term "diesel" refers to middle distillate fuels containing at least predominantly C10-C25 hydrocarbons. In one embodiment, diesel is further defined to refer to a composition containing at least predominantly C10-C25 hydrocarbons, and further having a boiling range of from about 165.6 °C (330 °F) to about 371.1 °C (700 °F). In an alternative embodiment, diesel is as defined above to refer to a composition containing at least predominantly C10-C25 hydrocarbons, having a boiling range of from about 165.6 °C (330 °F) to about 371.1 °C (700 °F), and further defined to meet ASTM D975.
[013] The term "oil soluble" means that for a given additive, the amount needed to provide the desired level of activity or performance can be incorporated by being dissolved, dispersed or suspended in an oil of lubricating viscosity. Usually, this means that at least 0.001% by weight of the additive can be incorporated in a lubricating oil composition. The term "fuel soluble" is an analogous expression for additives dissolved, dispersed or suspended in fuel.
[014] A "minor amount" means less than 50 wt% of a composition, expressed in respect of the stated additive and in respect of the total weight of the composition, reckoned as active ingredient of the additive.
[015] An "engine" or a "combustion engine" is a heat engine where the combustion of fuel occurs in a combustion chamber. An "internal combustion engine" is a heat engine where the combustion of fuel occurs in a confined space ("combustion chamber"). A "spark ignition engine" is a heat engine where the combustion is ignited by a spark, usually from a spark plug. This is contrast to a "compression-ignition engine," typically a diesel engine, where the heat generated from compression together with injection of fuel is sufficient to initiate combustion without an external spark.
[016] The present invention provides fuel additive compositions and fuel compositions with one or more performance benefits. In some embodiments, the compositions are effective to prevent or reduce corrosion or rust. In some embodiments, the compositions are effective to prevent or reduce wear or friction. In particular, the reduction in friction may lead to gains in fuel efficiency. In some embodiments, the compositions are multifunctional in that two or more benefits (e.g., corrosion/rust and wear/friction reduction) are provided.
[017] In general, the fuel additive composition is a product of a reaction between a fatty acid and a polyamine which results in a long-chain polyamide. Whereas conventional rust and/or wear inhibitors rely on organic acid-type compositions, the polyamides of the present invention are non-acids which minimizes interactions with potential refinery process contaminants that can result in deposit formation or increased filter plugging. Other advantages will be apparent from the disclosure herein.
Fatty Acid
[018] In accordance with the present invention, the fuel additive is the product of an amidification reaction between a fatty acid and a polyamine. Any fatty acid
compatible with the present invention may be used. Typical fatty acid can have the following structure:
wherein R is an organic moiety having about 5 to 40 carbon atoms such as from 8 to 35 carbon atoms, 10 to 30 carbon atoms, or 15 to 25 carbon atoms. In some embodiments, R includes one or more heteroatoms. Suitable fatty acids include saturated and unsaturated fatty acids. The fatty acid may also be a mono-carboxylic acid or may have more one acid moiety (e.g., di-carboxylic acid).
[019] In some embodiments, the fatty acid is an aliphatic fatty acid. Examples of saturated fatty acids include aliphatic fatty acids. The aliphatic group may be linear or branched.
[020] Suitable aliphatic acids include, but are not limited to, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, 2- ethylbutyric acid, 3,3-dimethylbutyric acid, 2-methylpentanoic acid, 2-methylhexanoic acid, 4-methylhexanoic acid, 5-methylhexanoic acid, 2,2-dimethylpentanoic acid, 2- propylpentanoic acid, 2-ethylhexanoic acid, 2-methylheptanoic acid, isooctanoic acid, 3,5,5-trimethylhexanoic acid, 4-methyloctanoic acid, 4-methylnonanoic acid, isodecanoic acid, 2-butyloctanoic acid, isotridecanoic acid, 2-hexyldecanoic acid, isopalmitic acid, isostearic acid, 3-cyclohexylpropionic acid, 4-cyclohexylbutyric acid, and cyclohexanepentanoic acid.
[021] Suitable unsaturated fatty acids include fatty acids that contain double or triple carbon-carbon bond. Representative unsaturated fatty acids include palmitoleic acid, myristoleic acid, sapienic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linoelaidic acid, a-linoelaidic acid, arachidonic acid, eicosapentaenoic acid, erucic acid, and docasahexaenoic acid.
Polyamine
[022] Preferably, the polyamine has at least three amine nitrogen atoms per molecule, and more preferably, 4 to 12 amine nitrogens per molecule. Most preferred are polyamines having from about 6 to 10 nitrogen atoms per molecule.
[023] Preferred polyalkene polyamines also contain from about 4 to 20 carbon atoms, preferably from 2 to 3 carbon atoms per alkylene unit. The polyamine preferably has a carbon-to-nitrogen ratio of from 1 :1 to 10:1.
[024] Suitable polyamines include polyalkylene polyamines. Such polyamines will typically contain about 2 to about 12 nitrogen atoms and about 2 to about 24 carbon atoms. Specific examples include diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylene hexamine (PEHA), and heavier poly-alkylene-amines (HPA).
[025] Other specific examples of polyamines include N, N'-bis-(2- aminoethyl)piperazine) (Bis AEP), N-[(2-aminoethyl) 2-aminoethyl]piperazine) (PEEDA), 1 -(2-aminoethyl)-4-[(2-aminoethyl)amino]ethyl]-piperazine) (AEPEEDA) and 1-[2-[[2- [(2-aminoethyl)amino]ethyl]amino]ethyl]-piperazine) (PEDETA).
[026] Many of the polyamines suitable for use in the present invention are commercially available and others may be prepared by methods which are well known in the art. For example, methods for preparing amines and their reactions are detailed in Sidgewick's "The Organic Chemistry of Nitrogen", Clarendon Press, Oxford, 1966; Noller's "Chemistry of Organic Compounds", Saunders, Philadelphia, 2nd Ed., 1957; and Kirk-Othmer's "Encyclopedia of Chemical Technology", 2nd Ed., especially Volume 2, pp. 99 116.
[027] The polyamine reactant may be a single compound, but typically will be a mixture of compounds reflecting commercial polyamines. Typically, the commercial polyamine will be a mixture in which one or several compounds predominate with the average composition indicated. For example, tetraethylene pentamine prepared by the polymerization of aziridine or the reaction of dichloroethylene and ammonia will have both lower and higher amine members, e.g., triethylene tetramine, substituted
piperazines and pentaethylene hexamine, but the composition will be largely tetraethylene pentamine and the empirical formula of the total amine composition will closely approximate that of tetraethylene pentamine.
[028] Other examples of suitable polyamines include admixtures of amines of various molecular weights. Included are mixtures of diethylene triamine and heavy polyamine. A preferred polyamine admixture is a mixture containing 20% by weight diethylene triamine and 80% by weight heavy polyamine.
Reaction
[029] The fuel additive of the present invention is a reaction product of fatty acid and polyamine. The reaction product is a polyamide or a fatty acid polyamide. The polyamides of the present invention may be obtained commercially or synthesized by any known method.
[030] As an illustrative example, a reaction between fatty acid and polyamine is described in U.S. Patent No. 3,169,980, which is hereby incorporated by reference. Here the polyamide is prepared by reacting the fatty acid and polyamine at temperatures in the range from about 120 °C (248 °F) to about 260 °C (500 °F). The amidification reaction requires from about 2 to 10 hours. Condensate water is subsequently removed. Reduced pressures may be needed to achieve amidification at the lower reaction temperatures. The proportion of fatty acid and polyamine may be such that the moles of fatty acid are equal to the molar equivalents of amine groups in the polyamine.
[031] A polyamide resulting from tetraethylenepentamine and a mixture of straight and branched-chain fatty acids is described by the following. A reaction vessel is charged with a mixture of tetraethylenepentamine and silicone foam inhibitor. The mixture is blanketed with nitrogen gas and heated to about 120°C. Next, a mixture of fatty acids is introduced and reaction temperature is raised to remove water. Temperature is raised again at atmospheric pressure for about an hour and then maintained under vacuum for about 7 hours.
Fuel Compositions
[032] The compounds of the present disclosure may be useful as additives in hydrocarbon fuels boiling in the gasoline or diesel range.
[033] The concentration of the polyamide compounds of the present disclosure in hydrocarbon fuel may range from 25 to 5000 parts per million (ppm) by weight (e.g., 50 to 1000 ppm).
[034] The compounds of the present disclosure may be formulated as a concentrate using an inert stable oleophilic (i.e., soluble in hydrocarbon fuel) organic solvent boiling in a range of 65 °C to 205 °C. An aliphatic or an aromatic hydrocarbon solvent may be used, such as benzene, toluene, xylene, or higher-boiling aromatics or aromatic thinners. Aliphatic alcohols containing 2 to 8 carbon atoms, such as ethanol, isopropanol, methyl isobutyl carbinol, n-butanol and the like, in combination with the hydrocarbon solvents are also suitable for use with the present additives. In the concentrate, the amount of the additive may range from 10 to 70 wt% (e.g., 20 to 40 wt%).
[035] In gasoline fuels, other well-known additives can be employed including oxygenates (e.g., ethanol, methyl tert-butyl ether), other anti-knock agents, and detergents/dispersants (e.g., hydrocarbyl amines, hydrocarbyl poly(oxyalkylene) amines, succinimides, Mannich reaction products, aromatic esters of polyalkylphenoxyalkanols, or polyalkylphenoxyaminoalkanes). Additionally, friction modifiers, antioxidants, metal deactivators and demulsifiers may be present.
[036] In diesel fuels, other well-known additives can be employed, such as pour point depressants, flow improvers, cetane improvers, and the like.
[037] A fuel-soluble, non-volatile carrier fluid or oil may also be used with compounds of this disclosure. The carrier fluid is a chemically inert hydrocarbon- soluble liquid vehicle which substantially increases the non-volatile residue (NVR), or solvent-free liquid fraction of the fuel additive composition while not overwhelmingly contributing to octane requirement increase. The carrier fluid may be a natural or synthetic oil, such as mineral oil, refined petroleum oils, synthetic polyalkanes and
alkenes, including hydrogenated and unhydrogenated polyalphaolefins, synthetic polyoxyalkylene-derived oils, such as those described in U.S. Patent Nos. 3,756,793; 4,191,537; and 5,004,478; and in European Patent Appl. Pub. Nos. 356,726 and 382,159.
[038] The carrier fluids may be employed in amounts ranging from 35 to 5000 ppm by weight of the hydrocarbon fuel (e.g., 50 to 3000 ppm of the fuel). When employed in a fuel concentrate, carrier fluids may be present in amounts ranging from 20 to 60 wt% (e.g., 30 to 50 wt%).
[039] The following illustrative examples are intended to be non-limiting.
EXAMPLES
[040] The polyamide tested is the reaction product of isostearic acid and tetraethylenepentamine (TEPA). Initially, 6 samples were prepared and tested for corrosion according to ASTM D665B. The samples contain either just base fuel (Samples 1 and 2) or base fuel and the polyamide (Samples 3, 4, 5, and 6) at varying amounts.
[041] Summary of the tested samples and corrosion results (ASTM D665B) is shown in Table 1 below. Visual confirmation of the corrosion test is shown clearly in FIG. 1.
Table 1
[042] Additional testing was performed to measure the friction performance of the polyamide according to ASTM 6079. Sample 7 contains just the base fuel. Samples 8, 9, 10, and 11 contain either baseline formulation 1 or baseline formulation 2 and varying amounts of the polyamide.
[043] Table 2 summarizes the tested samples and the results (ASTM 6079).
Table 2
Baseline Formulation 1 (BL1): Base fuel + mixture of fuel detergents + 5 vol% Methyl tert-butyl ether
Baseline Formulation 2 (BL2): Base fuel + mixture of fuel detergents + E10
Claims (12)
1. A method for preventing or reducing corrosion or wear in gasoline engine by supplying a fuel composition comprising a reaction product of fatty acid and polyamine.
2. The method of claim 1, wherein the fuel composition comprises a hydrocarbon fuel boiling within range of gasoline or diesel.
3. The method of claim 1, wherein the fatty acid is an aliphatic fatty acid having 2 to 30 carbons.
4. The method of claim 3, wherein the aliphatic fatty acid is hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, 2- ethylbutyric acid, 3,3-dimethylbutyric acid, 2-methylpentanoic acid, 2-methylhexanoic acid, 4-methylhexanoic acid, 5-methylhexanoic acid, 2,2-dimethylpentanoic acid, 2- propylpentanoic acid, 2-ethylhexanoic acid, 2-methylheptanoic acid, isooctanoic acid, 3,5,5-trimethylhexanoic acid, 4-methyloctanoic acid, 4-methylnonanoic acid, isodecanoic acid, 2-butyloctanoic acid, isotridecanoic acid, 2-hexyldecanoic acid, isopalmitic acid, isostearic acid, 3-cyclohexylpropionic acid, 4-cyclohexylbutyric acid, or cyclohexanepentanoic acid.
5. The method of claim 1, wherein the polyamine has about 2 to about 12 nitrogen atoms and about 2 to about 24 carbon atoms.
6. The method of claim 1, wherein the polyamine is diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylene hexamine, poly- alkylene-amines, N, N'-bis-(2-aminoethyl)piperazine), N-[(2-aminoethyl) 2-
aminoethyl] piperazine), 1 -(2-aminoethyl)-4-[(2-aminoethyl)amino]ethyl]-piperazine) or 1-[2-[[2-[(2-aminoethyl)amino]ethyl]amino]ethyl]-piperazine).
7. A method for preventing or reducing corrosion or wear in gasoline engine while providing anti-wear or friction protection by supplying a fuel composition comprising a fuel additive comprising a reaction product of fatty acid and polyamine.
8. The method of claim 7, wherein the fuel composition comprises a hydrocarbon fuel boiling within range of gasoline or diesel.
9. The method of claim 7, wherein the fatty acid is an aliphatic fatty acid having 2 to 30 carbons.
10. The method of claim 9, wherein the aliphatic fatty acid is hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, 2- ethylbutyric acid, 3,3-dimethylbutyric acid, 2-methylpentanoic acid, 2-methylhexanoic acid, 4-methylhexanoic acid, 5-methylhexanoic acid, 2,2-dimethylpentanoic acid, 2- propylpentanoic acid, 2-ethylhexanoic acid, 2-methylheptanoic acid, isooctanoic acid, 3,5,5-trimethylhexanoic acid, 4-methyloctanoic acid, 4-methylnonanoic acid, isodecanoic acid, 2-butyloctanoic acid, isotridecanoic acid, 2-hexyldecanoic acid, isopalmitic acid, isostearic acid, 3-cyclohexylpropionic acid, 4-cyclohexylbutyric acid, or cyclohexanepentanoic acid.
11. The method of claim 7, wherein the polyamine has about 2 to about 12 nitrogen atoms and about 2 to about 24 carbon atoms.
12. The method of claim 7, wherein the polyamine is diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylene hexamine, poly-
14 alkylene-amines, N, N'-bis-(2-aminoethyl)piperazine), N-[(2-aminoethyl) 2- aminoethyl] piperazine), 1-(2-aminoethyl)-4-[(2-aminoethyl)amino]ethyl]-piperazine) or 1-[2-[[2-[(2-aminoethyl)amino]ethyl]amino]ethyl]-piperazine).
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US202163255593P | 2021-10-14 | 2021-10-14 | |
US63/255,593 | 2021-10-14 | ||
PCT/IB2022/059422 WO2023062477A1 (en) | 2021-10-14 | 2022-10-03 | Polyamide fuel additives |
Publications (1)
Publication Number | Publication Date |
---|---|
AU2022366282A1 true AU2022366282A1 (en) | 2024-03-28 |
Family
ID=83594298
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2022366282A Pending AU2022366282A1 (en) | 2021-10-14 | 2022-10-03 | Polyamide fuel additives |
Country Status (5)
Country | Link |
---|---|
CN (1) | CN118019833A (en) |
AU (1) | AU2022366282A1 (en) |
CA (1) | CA3234489A1 (en) |
CO (1) | CO2024005982A2 (en) |
WO (1) | WO2023062477A1 (en) |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3169980A (en) | 1961-03-31 | 1965-02-16 | California Research Corp | Fatty acid polyamide |
US3468639A (en) * | 1965-08-06 | 1969-09-23 | Chevron Res | Gasolines containing deposit-reducing monoamides of polyamines characterized by improved water tolerance |
US3655351A (en) * | 1969-05-29 | 1972-04-11 | Cities Service Oil Co | Gasoline composition |
GB1346765A (en) | 1970-06-16 | 1974-02-13 | Shell Int Research | Fuel compositions |
US3894849A (en) * | 1973-11-29 | 1975-07-15 | Du Pont | Gasoline |
US4191537A (en) | 1976-06-21 | 1980-03-04 | Chevron Research Company | Fuel compositions of poly(oxyalkylene) aminocarbamate |
DE3826797A1 (en) | 1988-08-06 | 1990-02-08 | Basf Ag | FUEL COMPOSITIONS CONTAINING POLYCARBONIC ACIDIC LOW-CHAIN ALCOHOLS |
DE3838918A1 (en) | 1988-11-17 | 1990-05-23 | Basf Ag | FUELS FOR COMBUSTION ENGINES |
EP0382159A1 (en) | 1989-02-06 | 1990-08-16 | E.I. Du Pont De Nemours And Company | Defouling of fuel systems |
GB2486255A (en) * | 2010-12-09 | 2012-06-13 | Innospec Ltd | Improvements in or relating to additives for fuels and lubricants |
-
2022
- 2022-10-03 AU AU2022366282A patent/AU2022366282A1/en active Pending
- 2022-10-03 CA CA3234489A patent/CA3234489A1/en active Pending
- 2022-10-03 WO PCT/IB2022/059422 patent/WO2023062477A1/en active Application Filing
- 2022-10-03 CN CN202280064836.0A patent/CN118019833A/en active Pending
-
2024
- 2024-05-09 CO CONC2024/0005982A patent/CO2024005982A2/en unknown
Also Published As
Publication number | Publication date |
---|---|
CN118019833A (en) | 2024-05-10 |
CA3234489A1 (en) | 2023-04-20 |
CO2024005982A2 (en) | 2024-05-20 |
WO2023062477A1 (en) | 2023-04-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7402185B2 (en) | Additives for fuel compositions to reduce formation of combustion chamber deposits | |
EP1357170B9 (en) | Friction modifier additives for fuel compositions and methods of use thereof | |
RU2485171C2 (en) | Functional fluids for internal combustion engines | |
US7435272B2 (en) | Friction modifier alkoxyamine salts of carboxylic acids as additives for fuel compositions and methods of use thereof | |
JP4713804B2 (en) | Use of alkoxylated oligoamine fatty acid salts as lubricity improvers for petroleum products | |
US20070193110A1 (en) | Fuel lubricity additives | |
EP2611892A2 (en) | Functionalized maleated fatty acids as non acidic fluid additives | |
CN113195691A (en) | Aminoalkanediols and carboxylates as fuel efficiency improving additives | |
WO2023062477A1 (en) | Polyamide fuel additives | |
KR20240088856A (en) | polyamide fuel additive | |
CA2173072C (en) | Fuel compositions containing organic molybdenum complexes | |
US20220333027A1 (en) | Reducing friction in combustion engines through fuel additives |