WO2014146928A1 - Use of a hydrocarbyl-substituted dicarboxylic acid for improving or boosting the separation of water from fuel oils which comprises detergent additive - Google Patents
Use of a hydrocarbyl-substituted dicarboxylic acid for improving or boosting the separation of water from fuel oils which comprises detergent additive Download PDFInfo
- Publication number
- WO2014146928A1 WO2014146928A1 PCT/EP2014/054636 EP2014054636W WO2014146928A1 WO 2014146928 A1 WO2014146928 A1 WO 2014146928A1 EP 2014054636 W EP2014054636 W EP 2014054636W WO 2014146928 A1 WO2014146928 A1 WO 2014146928A1
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- WO
- WIPO (PCT)
- Prior art keywords
- weight
- hydrocarbyl
- acid
- fuel oils
- use according
- Prior art date
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- 239000000295 fuel oil Substances 0.000 title claims abstract description 42
- 239000000654 additive Substances 0.000 title claims abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 239000003599 detergent Substances 0.000 title claims abstract description 20
- 238000000926 separation method Methods 0.000 title claims abstract description 11
- 230000000996 additive effect Effects 0.000 title claims description 21
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 title abstract description 21
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 239000003085 diluting agent Substances 0.000 claims abstract description 5
- 239000002816 fuel additive Substances 0.000 claims abstract description 5
- 239000012141 concentrate Substances 0.000 claims abstract description 4
- -1 anhydride compound Chemical class 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 150000008064 anhydrides Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 239000003921 oil Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 11
- 239000000194 fatty acid Substances 0.000 claims description 11
- 229930195729 fatty acid Natural products 0.000 claims description 11
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 9
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 9
- 235000013311 vegetables Nutrition 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 229940014800 succinic anhydride Drugs 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 238000005956 quaternization reaction Methods 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000002551 biofuel Substances 0.000 claims description 4
- 229920001568 phenolic resin Polymers 0.000 claims description 4
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 2
- 125000000743 hydrocarbylene group Chemical group 0.000 claims 1
- 239000000306 component Substances 0.000 description 22
- 239000002283 diesel fuel Substances 0.000 description 18
- 239000000446 fuel Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- 239000003225 biodiesel Substances 0.000 description 11
- 125000005907 alkyl ester group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000003925 fat Substances 0.000 description 6
- 235000019197 fats Nutrition 0.000 description 6
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 6
- 239000008158 vegetable oil Substances 0.000 description 6
- 239000010775 animal oil Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 150000002823 nitrates Chemical class 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 230000001804 emulsifying effect Effects 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 239000006078 metal deactivator Substances 0.000 description 3
- 229960001047 methyl salicylate Drugs 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- NKRVGWFEFKCZAP-UHFFFAOYSA-N 2-ethylhexyl nitrate Chemical compound CCCCC(CC)CO[N+]([O-])=O NKRVGWFEFKCZAP-UHFFFAOYSA-N 0.000 description 2
- 208000016444 Benign adult familial myoclonic epilepsy Diseases 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-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
- 235000019482 Palm oil Nutrition 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- UEFBRXQBUTYIJI-UHFFFAOYSA-N decyl nitrate Chemical compound CCCCCCCCCCO[N+]([O-])=O UEFBRXQBUTYIJI-UHFFFAOYSA-N 0.000 description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 208000016427 familial adult myoclonic epilepsy Diseases 0.000 description 2
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 2
- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid group Chemical class C(CCCC(=O)O)(=O)O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- AGDYNDJUZRMYRG-UHFFFAOYSA-N hexyl nitrate Chemical compound CCCCCCO[N+]([O-])=O AGDYNDJUZRMYRG-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000003949 imides Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- TXQBMQNFXYOIPT-UHFFFAOYSA-N octyl nitrate Chemical compound CCCCCCCCO[N+]([O-])=O TXQBMQNFXYOIPT-UHFFFAOYSA-N 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
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- 238000006116 polymerization reaction Methods 0.000 description 2
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- PSTVZBXGCKLSQA-UHFFFAOYSA-N (1-methylcyclohexyl) nitrate Chemical compound [O-][N+](=O)OC1(C)CCCCC1 PSTVZBXGCKLSQA-UHFFFAOYSA-N 0.000 description 1
- OLJOBIJKBAHJBG-UHFFFAOYSA-N (1-propan-2-ylcyclohexyl) nitrate Chemical compound [O-][N+](=O)OC1(C(C)C)CCCCC1 OLJOBIJKBAHJBG-UHFFFAOYSA-N 0.000 description 1
- 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
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
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- C—CHEMISTRY; METALLURGY
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- 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
- C10L1/146—Macromolecular compounds according to different macromolecular groups, mixtures thereof
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
-
- 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
-
- 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
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- 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
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- 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
- C10L1/188—Carboxylic acids; metal salts thereof
- C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
- C10L1/1883—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom polycarboxylic acid
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- 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
- C10L1/188—Carboxylic acids; metal salts thereof
- C10L1/189—Carboxylic acids; metal salts thereof having at least one carboxyl group bound to an aromatic carbon atom
- C10L1/1895—Carboxylic acids; metal salts thereof having at least one carboxyl group bound to an aromatic carbon atom polycarboxylic acid
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
- C10L1/1981—Condensation polymers of aldehydes or ketones
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- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
- C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/23—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
- C10L1/233—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles
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- C10L1/00—Liquid carbonaceous fuels
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- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
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- 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)
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- C10L2200/00—Components of fuel compositions
- C10L2200/04—Organic compounds
- C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
- C10L2200/0438—Middle or heavy distillates, heating oil, gasoil, marine fuels, residua
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- 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
- C10L2200/0461—Fractions defined by their origin
- C10L2200/0469—Renewables or materials of biological origin
- C10L2200/0476—Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel
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- 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
- C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
- C10L2230/08—Inhibitors
- C10L2230/086—Demulsifiers
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- 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
- C10L2300/00—Mixture of two or more additives covered by the same group of C10L1/00 - C10L1/308
- C10L2300/20—Mixture of two components
Definitions
- the present invention relates to the use of a hydrocarbyl-substituted dicarboxylic acid comprising at least one hydrocarbyl substituent of from 10 to 3000 carbon atoms for improving or boosting the separation of water from fuel oils which comprise (B) at least one additive with detergent action.
- Fuel oils such as middle distillates, e.g. diesel fuels, heating oils or jet fuels, often contain small amounts of water, typically in the region of from several parts per millions up to several per cent by weight, due to condensation of water into the cold fuel oils and into the storage tanks and pipelines during transport and storage. This amount of water partly separates as a layer at the bottom of the storage tank and partly is emulsified in the fuel oil. The presence of water is unde- sired as it can cause severe problems on transport and on use in combustion engines and heating devices.
- German laid open Patent Application 1 645 705 discloses to use of amides of carboxylic acids to dehaze hydrocarbon mixtures, e.g. heating oil and diesel fuel. No hint is given to any possible interactions or synergistic interactions of the said amides with further middle distillate performance additives such as additives with detergent action or further additives with dehazing action.
- the teaching of (1 ) refers to dehaze the hydrocarbon mixtures, i.e. to clear them up by generating hydrocarbon-water-emulsions, such technical solution may only work with relatively small amounts of water; this method will fail with larger amounts of water.
- Chinese Patent Application 102277212 A (2) relates to a diesel performance additive which is a mixture of tall oil fatty acids, an oleic acid amide and a naphthenic acid imidazoline.
- the said three-component additive is recommended as an emulsifying agent to dehaze and clear up die- sel fuels. Similar to (1 ) above, no hint is given to any possible interactions or synergistic interactions of the said amides with further middle distillate performance additives such as additives with detergent action or further additives with dehazing action.
- As the teaching of (2) also refers to dehaze the diesel fuels, i.e. to clear them up by generating hydrocarbon-water-emulsions, such technical solution may only work with relatively small amounts of water; this method will fail with larger amounts of water.
- U.S. Patent No. 4 129 508 (3) discloses reaction products of hydrocarbyl-substituted succinic acids or their anhydrides with polyalkylene glycols or their monoethers, organic alkaline metal salts and alkoxylated amines. Such reaction products act as demulsifiers in fuels like diesel fuel.
- hydrocarbyl-substituted dicarboxylic acid (A) for improv- ing or boosting the separation of water from fuel oils comprising one or more additives with detergent action has been found.
- water present in the fuel oils is separated as a layer at the bottom of a separation device and, thereafter, can be easily removed.
- the water content in fuel oils which can be removed in this way is normally from about 200 ppm by weight to about 10% by weight, especially from about 1000 ppm by weight to about 5% by weight.
- Emulsifying water in the fuel oil by interaction with the hydrocarbyl-sub-stituted dicarboxylic acid (A) occurs only to a negligible minor amount.
- the hydrocarbyl-substituted dicarboxylic acid (A) improves and completes the phase separation of water from the fuel oils which occurs with larger amounts of water present in the fuel oils already without any performance additive but in an incomplete way.
- (A) boosts the phase separation of water from fuel oils if other surface active additives, especially certain commercially available dehazers, are already present in the fuel oils. Astonishingly, the interaction between (A) and certain commercially available dehazers which are by nature emulsi-fying additives also leads to an improved demulsifying and water phase separating action.
- the hydrocarbyl-substituted dicarboxylic acid (A) is applied in the form of the free acid, i.e. two COOH groups are present, or in the form of the anhydride which may be an intramolecular anhydride (like succinic anhydride, glutaric anhydride or phthalic anhydride) or an intermolecular anhydride linking two dicarboxylic acid molecules together.
- the car- boxylic functions may be present in salt form, e.g. as alkali or alkaline metal salts salts or as ammonium or substituted ammonium salts, depending on the pH value of the liquid phase.
- a single hydrocarbyl-substituted dicarboxylic acid species (A) or a mixture of different hydrocarbyl- substituted dicarboxylic acids (A) may be used.
- the hydrocarbyl substituent to the instant dicarboxylic acids preferably exhibits from 12 to 2000, more preferably from 14 to 1000, still more preferably from 16 to 500, most preferably from 20 to 200 carbon atoms.
- the hydrocarbyl substituent may be saturated or unsaturated, linear or branched; it may also include alicyclic, heterocyclic or aro-matic ring systems.
- Typical examples of hydrocarbyl substituents include linear and branched alkyl and alkenyl radical with 10, 1 1 , 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 24, 26, 28 and 30 carbon atoms in the chain.
- hydrocarbyl substituents are synthetically produced by oligomeri-zation or polymerization of olefin monomers such as ethene, propene, 1 -butene, 2-butene, isobutene, 1 - penten, 1 -hexen, 1 -octen or 1 -decen; follow-up transformations of such oligomerization or polymerization products may be applied.
- olefin monomers such as ethene, propene, 1 -butene, 2-butene, isobutene, 1 - penten, 1 -hexen, 1 -octen or 1 -decen
- dodecyl or dodecenyl substituents are produced by tetramerization of propene or trimerization of butenes and tridecyl or tride- cenyl substituents are made from the aforementioned Ci2-substituents by subsequent hydro- formylation.
- substituents with 10 to about 30 carbon atoms may also be of natural origin.
- Substituents of natural origin are normally derived from saturated or unsaturated fatty acids or the corresponding fatty alcohols. Such substituents of natural origin are in most cases linear.
- the at least one hydrocarbyl substituent of (A) is a polyisobutenyl substituent comprising from 20 to 200, preferably from 24 to 160, more preferably from 28 to 140, most preferably from 32 to 100 carbon atoms.
- the length of the polyisobutenyl substituent can be defined by its number average molecular weight (M n ) of from 300 to 2800, preferably of from 350 to 2300, more preferably of from 400 to 2000, most preferably of from 450 to 1400; such M n numbers normally relate to a polydispersity (M w /M n ) of from 1.1 to 4, preferably of from 1 .3 to 2.5.
- a typical polyisobutenyl substitutent comprises from 60 to 80 carbon atoms or is defined by a number average molecular weight of from 850 to 1 150.
- the polyisobutenyl substituent may be saturated, e.g.
- a polyisobutyl halide when attaching a polyisobutyl halide to an aromatic dicarboxylic acid (such as phthalic acid) via Friedel-Crafts reaction or to an olefinically unsaturated dicarbocylic acid (such as maleic acid or maleic anhydride), or may contain an olefinic double bond next to the link-up to the dicarboxylic acid molecule, e.g. when attaching a polyisobuten molecule with a terminal double bond to an olefinically unsaturated dicarbocylic acid (such as maleic acid or maleic anhydride) via en reaction.
- aromatic dicarboxylic acid such as phthalic acid
- olefinically unsaturated dicarbocylic acid such as maleic acid or maleic anhydride
- hydrocarbyl-substituted dicarboxylic acid (A) itself may be of aliphatic, cycloalipha-tic, arali- phatic or aromatic nature, aliphatic dicarboxylic acids being preferred.
- Typical hydrocarbyl- substituted dicarboxylic acids (A) suitable for the present invention are derived from hydrocarbyl-substituted malonic acid, hydrocarbyl-substituted succinic acid, hydrocarbyl-substituted glutaric acid, hydrocarbyl-substituted adipic acid, hydro-carbyl-substituted pimelic acid, hydrocarbyl-substituted suberic acid, hydrocarbyl-substituted azelaic acid, hydrocarbyl-substituted sebacic acid, hydrocarbyl-substituted undecanedioic acid, hydrocarbyl-substituted dodecanedio- ic acid, hydrocar
- the hydrocarbyl-substituted dicarboxylic acid (A) comprises a hy- drocarbylene bridging group between the two carboxylic functions of from 1 to 10, preferably of from 2 to 8, more preferably of from 2 to 6, most preferably of 2, 3 or 4 carbon atoms in a line.
- bridging carbon atom line may be a linear aliphatic alkylene or alkenylene chain with or without C1 - to C 4 -side chains, an araliphatic bridging group incorporating a benzene ring into the aliphatic carbon atom chain, or a phenylene bridging group.
- the hydrocarbyl-substituted dicarboxylic acid (A) is a polyisobutenylsuccinic acid with one polyisobutenyl substituent comprising from 20 to 200, pref- erably from 24 to 160, more preferably from 28 to 140, most preferably from 32 to 100 carbon atoms or, as an alternative, with a polyisobutenyl with a number average molecular weight (M n ) of from 300 to 2800, preferably of from 350 to 2300, more preferably of from 400 to 2000, most preferably of from 450 to 1400.
- M n number average molecular weight
- Such preferred polyisobutenylsuccinic acid may also be applied according to the present invention in the form of the polyisobutenylsuccinic anhydride.
- Polyisobutenylsuccinic acids with two free COOH functions which are suitable for use of water separation from fuel oils according the present invention can be easily prepared in dry substance by hydrolysis of the corresponding anhydrides, i.e. by simply mixing the said anhydrides with the equimolar amount of water and heating up to a temperature of from about 70°C to about 120°C for a sufficient time period (usually from 2 to 20 hours).
- Additives with detergent action of component (B) refer, in the context of the present invention, to those compounds whose effect in an internal combustion engine or in a heating device, especially a diesel engine, consists predominantly or at least essentially of eliminating and/or pre- venting deposits.
- the detergents are preferably amphiphilic substances which have at least one hydrophobic hydrocarbyl radical having a number-average molecular weight (M n ) of 85 to 20.000, especially of 300 to 5000, and in particular of 500 to 2500, and at least one polar moiety-
- the fuel oils comprise at least one additive component with detergent action (B) which is selected from (i) compounds with moieties derived from succinic anhydride and having hydroxyl and/or amino and/or amido and/or imido groups; nitrogen compounds quaternized in the presence of an acid or in an acid-free manner, obtainable by addition of a compound comprising at least one oxygen- or nitrogen- containing group reactive with an anhydride and additionally at least one quaternizable amino group onto a polycarboxylic anhydride compound and subsequent quaternization;
- derivatives with aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetet- ramine or tetraethylenepentamine.
- the moieties with hydroxyl and/or amino and/or amido and/or imido groups are for example carboxylic acid groups, acid amides, acid amides of di- or polyamines, which, as well as the amide function, also have free amine groups, succinic acid derivatives with an acid and an amide function, carboxyimides with monoamines, carboxyimides with di- or polyamines, which, as well as the imide function, also have free amine groups, and diimides, which are formed by the reaction of di- or polyamines with two succinic acid derivatives.
- Such fuel additives are described especially in US-A 4 849 572.
- Nitrogen compounds quaternized in the presence of an acid or in an acid-free manner according to the above group (ii) are obtainable by addition of a compound which corn-prises at least one oxygen- or nitrogen-containing group reactive with an anhydride and additionally at least one quaternizable amino group onto a polycarboxylic anhydride compound and subsequent quaternization, especially with an epoxide, e.g. styrene or propylene oxide, in the absence of free acid, as described in WO 2012/004300, or with a carboxylic ester, e.g. dimethyl oxalate or methyl salicylate.
- epoxide e.g. styrene or propylene oxide
- Suitable compounds having at least one oxygen- or nitrogen-containing group reactive with anhydride and additionally at least one quaternizable amino group are especially polyamines having at least one primary or secondary amino group and at least one tertiary amino group.
- Useful polycarboxylic anhydrides are especially dicarboxylic acids such as succinic acid, having a relatively long-chain hydrocarbyl substituent, preferably having a number- average molecular weight M n for the hydrocarbyl substituent of 200 to 10.000, in particular of 350 to 5000.
- Such a quaternized nitrogen compound is, for example, the reaction product, obtained at 40°C, of polyisobutenylsuccinic anhydride, in which the polyisobutenyl radical typically has an M n of 1000, with 3-(dimethylamino)propylamine, which constitutes a polyisobutenylsuc- cinic monoamide and which is subsequently quaternized with dimethyl oxalate or methyl salicylate or with styrene oxide or propylene oxide in the absence of free acid.
- polyisobutenylsuccinic anhydride in which the polyisobutenyl radical typically has an M n of 1000, with 3-(dimethylamino)propylamine, which constitutes a polyisobutenylsuc- cinic monoamide and which is subsequently quaternized with dimethyl oxalate or methyl salicylate or with styrene oxide or propylene oxide in the absence of free
- polytetrahydrobenzoxazines and bistetrahydrobenzoxazines according to the above group (iii) are described in WO 2012/076428.
- Such polytetrahydro-benzoxazines and bistetrahydrobenzoxazines are obtainable by successively reacting, in a first reaction step, a Ci- to C20- alkylenediamine having two primary amino functions, e.g. 1 ,2-ethylenediamine, with a Ci- to Ci2-aldehyde, e.g.
- a tert-octyl, n-nonyl, n-dodecyl or polyisobutyl radical having an M n of 1000, in a stoichiometric ratio relative to the originally used alkylenediamine of 1.2:1 to 3:1 at a temperature of 30 to 120°C and optionally in a third reaction step heating the bistetrahydrobenzoxazine thus obtained to a temperature of 125 to 280°C for at least 10 minutes.
- the hydrocarbyl-substituted dicarboxylic acid (A) is preferably used together with quarternized nitrogen compounds (ii) for compo-nent (B).
- the present hydrocarbyl-substituted dicarboxylic acid (A) and the at least one additive with detergent action for component (B) exhibit superior performance - even in the sense of synergism - in improving and/or boosting the separation of water from fuel oils when applied together with at least one dehazer exhibiting emulsifying action on its own when used alone as additive component (C) selected from ) alkoxylation copolymers of ethylene oxide, propylene oxide, butylene oxide, styrene oxide and/or other oxides, e.g. epoxy based resins;
- Dehazer components (iv) and (v) are normally commercially available products, e.g. the dehaz- er products available from Baker Petrolite under the brand name of Tolad® such as Tolad® 2898, 9360K, 9348, 9352K or 9327.
- the fuel oils additionally comprise as additive component (D) at least on cetane number improver.
- Cetane number improvers used are typically organic nitrates. Such organic nitrates are especially nitrate esters of unsubstituted or substituted aliphatic or cycloaliphatic alcohols, usually having up to about 10, in particular having 2 to 10 carbon atoms.
- the alkyl group in these nitrate esters may be linear or branched, and saturated or unsaturated.
- Typical examples of such nitrate esters are methyl nitrate, ethyl nitrate, n-propyl nitrate, isopropyl nitrate, allyl nitrate, n-butyl nitrate, isobutyl nitrate, sec-butyl nitrate, tert-butyl nitrate, n-amyl nitrate, isoamyl nitrate, 2-amyl nitrate, 3-amyl nitrate, tert-amyl nitrate, n-hexyl nitrate, n-heptyl nitrate, sec-heptyl nitrate, n-octyl nitrate, 2-ethylhexyl nitrate, sec-octyl nit
- nitrate esters of alkoxy-substituted aliphatic alcohols such as 2- ethoxyethyl nitrate, 2-(2-ethoxy-ethoxy)ethyl nitrate, 1 -methoxypropyl nitrate or 4-ethoxybutyl nitrate.
- diol nitrates such as 1 ,6-hexamethylene dinitrate.
- cetane number improver classes mentioned preference is given to primary amyl nitrates, primary hexyl nitrates, octyl nitrates and mixtures thereof.
- 2-ethylhexyl nitrate is present in the fuel oils as the sole cetane number improver or in a mixture with other cetane number improvers.
- fuel oils means preferably middle distillate fuels, especially diesel fuels.
- heating oils, jet fuels and kerosene shall also be encompassed.
- Diesel fuels or middle distillate fuels are typically mineral oil raffinates which generally have a boiling range from 100 to 400°C. These are usually distillates having a 95% point up to 360°C or even higher. However, these may also be what is called “ultra low sulfur diesel” or "city diesel", characterized by a 95% point of, for example, not more than 345°C and a sulfur content of not more than 0.005% by weight, or by a 95% point of, for example, 285°C and a sulfur content of not more than 0.001 % by weight.
- diesel fuels obtainable by refining, the main constituents of which are relatively long-chain paraffins, those obtainable in a synthetic way by coal gasification or gas liquefaction ["gas to liquid” (GTL) fuels] are suitable, too.
- mixtures of the aforementioned diesel fuels with renewable fuels (biofuel oils) such as bio- diesel or bioethanol.
- biofuel oils renewable fuels
- diesel fuels with low sulfur content i.e. with a sulfur content of less than 0.05% by weight, preferably of less than 0.02% by weight, particularly of less than 0.005% by weight and especially of less than 0.001 % by weight of sulfur.
- the hydrocarbyl-substituted dicarboxylic acid (A) is used together with the aforementioned components (B), (C) and, if desired (D), in fuel oils which consist to an extent of 0.1 to 100% by weight, preferably to an extent of 0.1 to less than 100% by weight, especially to an extent of 10 to 95% by weight and in particular to an extent of 30 to 90% by weight, of at least one biofuel oil based on fatty acid esters, and to an extent of 0 to 99.9% by weight, preferably to an extent of more than 0 to 99.9% by weight, especially to an extent of 5 to 90% by weight, and in particular to an extent of 10 to 70% by weight, of middle distillates of fossil origin and/or of synthetic origin and/or of vegetable and/or animal origin, which are essentially hydrocarbon mixtures and are free of fatty acid esters.
- hydrocarbyl-substituted dicarboxylic acid (A) can also be used together with the aforementioned components (B), (C) and, if desired (D), in fuel oils which consist exclusively of middle distillates of fossil origin and/or of synthetic origin and/or of vegetable and/or animal origin, which are essentially hydrocarbon mixtures and are free of fatty acid esters.
- Fuel oil component (a) is usually also referred to as "biodiesel”.
- This preferably corn-prises essentially alkyl esters of fatty acids which derive from vegetable and/or animal oils and/or fats.
- Alkyl esters typically refer to lower alkyl esters, especially Ci- to C 4 -alkyl esters, which are ob- tainable by transesterifying the glycerides which occur in vegetable and/or animal oils and/or fats, especially triglycerides, by means of lower alcohols, for example, ethanol, n-propanol, iso- propanol, n-butanol, isobutanol, sec-butanol, tert-butanol or especially methanol ("FAME").
- FAME methanol
- oils which can be converted to corresponding alkyl esters and can thus serve as the basis of biodiesel are castor oil, olive oil, peanut oil, palm kernel oil, coconut oil, mustard oil, cottonseed oil, and especially sunflower oil, palm oil, soybean oil and rapeseed oil. Further examples include oils which can be obtained from wheat, jute, sesame and shea tree nut; it is additionally also possible to use arachis oil, jatropha oil and linseed oil. The extraction of these oils and the conversion thereof to the alkyl esters are known from the prior art or can be inferred therefrom.
- Vegetable fats can in principle likewise be used as a source for biodiesel, but play a minor role.
- animal oils and fats which can be converted to corresponding alkyl esters and can thus serve as the basis of biodiesel are fish oil, bovine tallow, porcine tallow and similar fats and oils obtained as wastes in the slaughter or utilization of farm animals or wild animals.
- the parent saturated or unsaturated fatty acids of said vegetable and/or animal oils and/or fats which usually have 12 to 22 carbon atoms and may bear an additional functional group such as hydroxyl groups, and which occur in the alkyl esters, are especially lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, elaidic acid, erucic acid and/or ricinoleic acid.
- Typical lower alkyl esters based on vegetable and/or animal oils and/or fats which find use as biodiesel or biodiesel components, are, for example, sunflower methyl ester, palm oil methyl ester (“PME”), soybean oil methyl ester (“SME”) and especially rapeseed oil methyl ester (“RME”).
- PME palm oil methyl ester
- SME soybean oil methyl ester
- RME rapeseed oil methyl ester
- the fuel oil component (b) shall be understood to mean the abovementioned middle distillate fuels, especially diesel fuels, especially those which boil in the range from 120 to 450°C.
- hydrocarbyl-substituted dicarboxylic acid (A) is used to- gether with the aforementioned components (B), (C) and, if desired (D), in fuel oils which have at least one of the following properties:
- polycyclic aromatic hydrocarbons in ( ⁇ ) shall be understood to mean polyaromatic hydrocarbons according to standard EN 12916. They are determined according to this standard.
- the fuel oils comprise said hydrocarbyl-substituted dicarboxylic acid (A) in the context of the present invention generally in an amount of from 1 to 1000 ppm by weight, preferably of from 5 to 500 ppm by weight, more preferably of from 3 to 300 ppm by weight, most preferably of from 5 to 200 ppm by weight, for example of from 10 to 100 ppm by weight.
- the additive with detergent action (B) or a mixture of a plurality of such additives with detergent action is present in the fuel oils typically in an amount of from 10 to 2000 ppm by weight, preferably of from 20 to 1000 ppm by weight, more preferably of from 50 to 500 ppm by weight, most preferably of from 30 to 250 ppm by weight, for example of from 50 to 150 ppm by weight.
- One or more dehazers as additive component (C), if any, are present in the fuel oils generally in an amount of from 0.5 to 100 ppm by weight, preferably of from 1 to 50 ppm by weight, more preferably of from 1.5 to 40 ppm by weight, most preferably of from 2 to 30 ppm by weight, for example of from 3 to 20 ppm by weight.
- the cetane number improver (D) or a mixture of a plurality of cetane number improvers is present in the fuel oils normally in an amount of form 10 to 10.000 ppm by weight, preferably of from 20 to 5000 ppm by weight, more preferably of from 50 to 2500 ppm by weight, most preferably of from 100 to 1000 ppm by weight, for example of from 150 to 500 ppm by weight.
- Subject matter of the present invention is also a fuel additive concentrate suitable for use in fuel oils, especially in diesel fuel, comprising
- hydrocarbyl-substituted dicarboxylic acid comprising at least one hydrocarbyl substituent of from 10 to 3000 carbon atoms
- nitrogen compounds quaternized in the presence of an acid or in an acid-free manner obtainable by addition of a compound comprising at least one oxygen- or nitrogen-containing group reactive with an anhydride and
- styrene oxide and/or other oxides e.g. epoxy based resins (v) alkoxylated phenol formaldehyde resins;
- (E) 0 to 50% by weight, preferably 5 to 50% by weight, more preferably 10 to 40% by
- Said fuel oils such as diesel fuels, or said mixtures of biofuel oils and middle distillates of fossil, synthetic, vegetable or animal origin, may comprise, in addition to the hydro-carbyl-substituted dicarboxylic acid (A) and components (B) and, if any (C) and (D), as coadditives further custom- ary additive components in amounts customary therefor, especially cold flow improvers, corrosion inhibitors, further demulsifiers, antifoams, antioxidants and stabilizers, metal deactivators, antistats, lubricity improvers, dyes (markers) and/or diluents and solvents.
- Said fuel additive concentrates may also comprise certain of the above coadditives in amounts customary therefor, e.g. corro-sion improvers, further demulsifiers, antifoams, antioxidants and stabilizers, metal deactivators, antistats and lubricity improvers.
- Cold flow improvers suitable as further coadditives are, for example, copolymers of ethylene with at least one further unsaturated monomer, in particular ethylene-vinyl acetate copolymers.
- Corrosion inhibitors suitable as further coadditives are, for example, succinic esters, in particular with polyols, fatty acid derivatives, for example oleic esters, oligomerized fatty acids and substituted ethanolamines.
- demulsifiers suitable as further coadditives are, for example, the alkali metal and alka- line earth metal salts of alkyl-substituted phenol- and naphthalenesulfonates and the alkali metal and alkaline earth metal salts of fatty acids, and also alcohol alkoxylates, e.g. alcohol ethox- ylates, phenol alkoxylates, e.g. tert-butylphenol ethoxylates or tert-pentylphenol ethoxylates, fatty acids themselves, alkylphenols, condensation products of ethylene oxide and propylene oxide, e.g. ethylene oxide-propylene oxide block copolymers, polyethyleneimines and polysilox- anes.
- alcohol alkoxylates e.g. alcohol ethox- ylates
- phenol alkoxylates e.g. tert-butylphenol ethoxylates or
- Antifoams suitable as further coadditives are, for example, polyether-modified poly-siloxanes.
- Antioxidants suitable as further coadditives are, for example, substituted phenols, e.g. 2,6-di- tert-butylphenol and 2,6-di-tert-butyl-3-methylphenol, and also phenylene-diamines, e.g. N,N'-di- sec-butyl-p-phenylenediamine.
- Metal deactivators suitable as further coadditives are, for example, salicylic acid derivatives, e.g. N,N'-disalicylidene-1 ,2-propanediamine.
- a lubricity improver suitable as a further coadditive is, for example, glyceryl mono-oleate.
- Suitable solvents and diluents as component (E), especially for diesel performance packages are, for example, nonpolar organic solvents, especially aromatic and aliphatic hydrocarbons, for example toluene, xylenes, "white spirit” and the technical solvent mixtures of the designations Shellsol® (manufactured by Royal Dutch/Shell Group), Exxol® (manu-factured by ExxonMobil) and Solvent Naphtha.
- polar organic solvents in particular alcohols such as 2-ethylhexanol, decanol and isotridecanol.
- the test was carried through in a commercially available diesel fuel composed of 100% of middle distillates of fossil origin (“DF1 ”) an in a commercially available biodiesel containing diesel fuel composed of 95% by weight of middle distillates of fossil origin and 5% by weight of FAME (“DF2").
- DF1 middle distillates of fossil origin
- DF2 biodiesel containing diesel fuel composed of 95% by weight of middle distillates of fossil origin and 5% by weight of FAME
- A1 was polyisobuten- ylsuccinic acid and A2 was polyisobutenylsuccinic anhydride.
- A2 was prepared by thermal en- reaction between polyisobuten (having an M n of 1000 and a content of 70 mol-% of terminal vinylidene double bonds) and maleic anhydride;
- A1 was prepared by hydrolysis of A2 with the equimolar amount of water at 100°C for 16 hours.
- A1 or A2 was admixed to a usual diesel detergent package comprising as component (B)(ii) the imide reaction product of polyisobutenylsuccinic anhydride, in which the polyiso- butenyl radical has an M n of 1000, with 3-(dimethylamino)propylamine which is subsequently quaternized with methyl salicylate, as component (C)(v) a dehazer commercially available from Baker Petrolite under the name of Tolad® 2898 and a commercially available polyether- modified polysiloxane antifoam ("AF").
- component (B)(ii) the imide reaction product of polyisobutenylsuccinic anhydride, in which the polyiso- butenyl radical has an M n of 1000, with 3-(dimethylamino)propylamine which is subsequently quaternized with methyl salicylate
- component (C)(v) a dehazer commercially available from Baker Petrolite under
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- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
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Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SG11201506396PA SG11201506396PA (en) | 2013-03-21 | 2014-03-11 | Use of a hydrocarbyl-substituted dicarboxylic acid for improving or boosting the separation of water from fuel oils which comprises detergent additive |
EP14708894.2A EP2976411A1 (en) | 2013-03-21 | 2014-03-11 | Use of a hydrocarbyl-substituted dicarboxylic acid for improving or boosting the separation of water from fuel oils which comprises detergent additive |
AU2014234560A AU2014234560A1 (en) | 2013-03-21 | 2014-03-11 | Use of a hydrocarbyl-substituted dicarboxylic acid for improving or boosting the separation of water from fuel oils which comprises detergent additive |
MYPI2015002144A MY185204A (en) | 2013-03-21 | 2014-03-11 | Use of a hydrocarbyl-substituted dicarboxylic acid for improving or boosting the separation of water from fuel oils which comprises detergent additive |
CN201480017246.8A CN105102594A (en) | 2013-03-21 | 2014-03-11 | Use of hydrocarbyl-substituted dicarboxylic acid for improving or boosting the separation of water from fuel oils which comprises detergent additive |
RU2015145010A RU2015145010A (en) | 2013-03-21 | 2014-03-11 | APPLICATION OF HYDROCARBIL-SUBSTITUTED DICARBOXYLIC ACID TO IMPROVE OR STIMULATE WATER SEPARATION FROM LIQUID FUEL |
KR1020157030284A KR20150133265A (en) | 2013-03-21 | 2014-03-11 | Use of a hydrocarbyl-substituted dicarboxylic acid for improving or boosting the separation of water from fuel oils which comprises detergent additive |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP13160351.6 | 2013-03-21 | ||
EP13160351 | 2013-03-21 |
Publications (1)
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WO2014146928A1 true WO2014146928A1 (en) | 2014-09-25 |
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PCT/EP2014/054636 WO2014146928A1 (en) | 2013-03-21 | 2014-03-11 | Use of a hydrocarbyl-substituted dicarboxylic acid for improving or boosting the separation of water from fuel oils which comprises detergent additive |
Country Status (9)
Country | Link |
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EP (1) | EP2976411A1 (en) |
KR (1) | KR20150133265A (en) |
CN (1) | CN105102594A (en) |
AR (1) | AR097129A1 (en) |
AU (1) | AU2014234560A1 (en) |
MY (1) | MY185204A (en) |
RU (1) | RU2015145010A (en) |
SG (1) | SG11201506396PA (en) |
WO (1) | WO2014146928A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015003961A1 (en) * | 2013-07-12 | 2015-01-15 | Basf Se | Use of a hydrocarbyl-substituted dicarboxylic acid for improving or boosting the separation of water from fuel oils and gasoline fuels |
GB2546866A (en) * | 2015-12-04 | 2017-08-02 | Afton Chemical Corp | Fuel additives for treating internal deposits of fuel injectors |
US10414988B2 (en) | 2015-12-02 | 2019-09-17 | Ecolab Usa Inc. | Methods of treating a stream comprising crude oil and water |
EP3511396B1 (en) | 2014-05-30 | 2020-07-29 | The Lubrizol Corporation | Low molecular weight imide containing quaternary ammonium salts |
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Also Published As
Publication number | Publication date |
---|---|
MY185204A (en) | 2021-04-30 |
AR097129A1 (en) | 2016-02-24 |
KR20150133265A (en) | 2015-11-27 |
CN105102594A (en) | 2015-11-25 |
RU2015145010A (en) | 2017-04-26 |
AU2014234560A1 (en) | 2015-09-10 |
EP2976411A1 (en) | 2016-01-27 |
SG11201506396PA (en) | 2015-10-29 |
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