NZ505170A - Ignition improved fuels doped with a cyclic ketone peroxide - Google Patents
Ignition improved fuels doped with a cyclic ketone peroxideInfo
- Publication number
- NZ505170A NZ505170A NZ505170A NZ50517098A NZ505170A NZ 505170 A NZ505170 A NZ 505170A NZ 505170 A NZ505170 A NZ 505170A NZ 50517098 A NZ50517098 A NZ 50517098A NZ 505170 A NZ505170 A NZ 505170A
- Authority
- NZ
- New Zealand
- Prior art keywords
- ketone
- fuel
- cyclic
- peroxides
- peroxide
- Prior art date
Links
- 239000000446 fuel Substances 0.000 title claims abstract description 101
- -1 cyclic ketone peroxide Chemical class 0.000 title claims abstract description 99
- 150000002978 peroxides Chemical class 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 30
- 150000002576 ketones Chemical class 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 23
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 21
- 239000002283 diesel fuel Substances 0.000 claims description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- 235000011468 Albizia julibrissin Nutrition 0.000 claims description 16
- 241001070944 Mimosa Species 0.000 claims description 16
- 229930195733 hydrocarbon Natural products 0.000 claims description 15
- 150000002430 hydrocarbons Chemical class 0.000 claims description 15
- 230000000052 comparative effect Effects 0.000 claims description 14
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims description 13
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 claims description 12
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 claims description 12
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 12
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 12
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 claims description 10
- 238000002485 combustion reaction Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 10
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 9
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 claims description 6
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 5
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 150000002118 epoxides Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 239000003344 environmental pollutant Substances 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 231100000719 pollutant Toxicity 0.000 claims description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 10
- NKRVGWFEFKCZAP-UHFFFAOYSA-N 2-ethylhexyl nitrate Chemical compound CCCCC(CC)CO[N+]([O-])=O NKRVGWFEFKCZAP-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000019401 acetone peroxide Nutrition 0.000 description 3
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000003997 cyclic ketones Chemical class 0.000 description 3
- 229940032007 methylethyl ketone Drugs 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- QSOMFNQEXNFPNU-UHFFFAOYSA-L magnesium;hydrogen sulfate;hydroxide;hydrate Chemical compound O.O.[Mg+2].[O-]S([O-])(=O)=O QSOMFNQEXNFPNU-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 description 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- NKXMBTKMOVMBPH-UHFFFAOYSA-N 1-phenylpentane-1,3-dione Chemical compound CCC(=O)CC(=O)C1=CC=CC=C1 NKXMBTKMOVMBPH-UHFFFAOYSA-N 0.000 description 1
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
- CEGGECULKVTYMM-UHFFFAOYSA-N 2,6-dimethylheptane-3,5-dione Chemical compound CC(C)C(=O)CC(=O)C(C)C CEGGECULKVTYMM-UHFFFAOYSA-N 0.000 description 1
- IEBAJFDSHJYDCK-UHFFFAOYSA-N 2-methylundecan-4-one Chemical compound CCCCCCCC(=O)CC(C)C IEBAJFDSHJYDCK-UHFFFAOYSA-N 0.000 description 1
- LCLCVVVHIPPHCG-UHFFFAOYSA-N 5,5-dimethylhexane-2,4-dione Chemical compound CC(=O)CC(=O)C(C)(C)C LCLCVVVHIPPHCG-UHFFFAOYSA-N 0.000 description 1
- KHZGUWAFFHXZLC-UHFFFAOYSA-N 5-methylhexane-2,4-dione Chemical compound CC(C)C(=O)CC(C)=O KHZGUWAFFHXZLC-UHFFFAOYSA-N 0.000 description 1
- IGMOYJSFRIASIE-UHFFFAOYSA-N 6-Methylheptan-2,4-dione Chemical compound CC(C)CC(=O)CC(C)=O IGMOYJSFRIASIE-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000000011 acetone peroxide Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000008264 cloud Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- TZMFJUDUGYTVRY-UHFFFAOYSA-N ethyl methyl diketone Natural products CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- ILPNRWUGFSPGAA-UHFFFAOYSA-N heptane-2,4-dione Chemical compound CCCC(=O)CC(C)=O ILPNRWUGFSPGAA-UHFFFAOYSA-N 0.000 description 1
- DGCTVLNZTFDPDJ-UHFFFAOYSA-N heptane-3,5-dione Chemical compound CCC(=O)CC(=O)CC DGCTVLNZTFDPDJ-UHFFFAOYSA-N 0.000 description 1
- NDOGLIPWGGRQCO-UHFFFAOYSA-N hexane-2,4-dione Chemical compound CCC(=O)CC(C)=O NDOGLIPWGGRQCO-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- GJYXGIIWJFZCLN-UHFFFAOYSA-N octane-2,4-dione Chemical compound CCCCC(=O)CC(C)=O GJYXGIIWJFZCLN-UHFFFAOYSA-N 0.000 description 1
- PJEPOHXMGDEIMR-UHFFFAOYSA-N octane-3,5-dione Chemical compound CCCC(=O)CC(=O)CC PJEPOHXMGDEIMR-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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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
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
-
- 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
- C10L1/1811—Organic compounds containing oxygen peroxides; ozonides
-
- 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
- C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
- C10L1/2286—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen triple bonds, e.g. nitriles
-
- 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
- C10L10/12—Use of additives to fuels or fires for particular purposes for improving the cetane number
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/16—Hydrocarbons
- C10L1/1608—Well defined compounds, e.g. hexane, benzene
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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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- C10L1/14—Organic compounds
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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
- C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
- C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
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Abstract
A fuel contains one or more cyclic ketone peroxides including 0.01 to 10 % weight of one or more cyclic ketone peroxides of formula I wherein R1 to R6 are independently hydrogen or optionally substituted, alkyl, cycloalkyl, aryl, aralkyl, or alkaryl provided that the peroxides of formula (I) make up at least 35% by weight of all cyclic ketone peroxides in the fuel.
Description
New Zealand Paient Spedficaiion for Paient Number 505170
IGNITION IMPROVED FUELS
The invention relates to fuels with improved ignition characteristics comprising one or more ketone peroxides, as well as to a process to prepare such fuels
The use of peroxides in fuels has long been common knowledge Back in the 1940s US 2,378,341 disclosed the use of a peroxide of a hydrocarbon having 10 at least one aliphatic tertiary carbon atom, the peroxy radical in said peroxide connecting two tertiary carbon atoms, while Ind. Ena Chem . Vol 41, No 8, pp 1679-1682 disclosed the use of di-tert-butyl peroxide and 2,2-bis(tert-butylperoxy)butane for the purpose of improving the ignition of diesel fuels Also, FR-B-862,070 disclosed a very hazardous process which is conducted at 15 undesired low temperatures to make polymeric ketone peroxides from mixtures of aliphatic ketones, and their use in fuel The products are said to have improved solubility in the fuel and a low crystallization temperature. FR-B-862,974 discloses the production of certain cyclic ketone peroxides and their use in diesel fuel to improve the ignition characteristics 20 In 1961, US 3,003,000 disclosed ketone peroxides and oligomeric ketone peroxides, a process to make them, and their generic use in, inter alia, diesel fuels. The process also yields some cyclic ketone peroxide by-products. These by-products are present in the oligomeric ketone peroxides in trace amounts Also, the use in diesel fuel formulations is not exemplified 25 US 3,116,300 (published in 1963) discloses dimeric cyclic ketone peroxides, viz. the product formed when two ketone molecules are reacted
Ignition improvers are desired for use in hydrocarbon distillates and residue-containing oils that are useful as fuels for combustion engines except for their 30 ignition characteristics Usually, such fuels suffer from a too long ignition lag, i e., the time between the injection of the fuel into the zone of combustion, as in
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directly injected engines such as diesel engines, and the moment the fuel ignites, or the time between the activation of external ignition sources, such as spark plugs, and the moment the fuel ignites As a result, poor combustion efficiency and rough engine operation are observed, with all attendant adverse 5 consequences The term improved ignition, therefore, means that in combustion engines fuel is burned with improved efficiency, which usually is obvious from the higher cetane number of the fuel and the reduced emission of pollutants upon combustion of the fuel in said engine As is well-known, the use of diesel fuel with improved ignition can result in reductions of the hydrocarbon, 10 carbon monoxide, NOx, and particulate matter (soot) emissions Depending on the type of fuel and the type and quantity of ignition improver used, reductions of 40% of said emissions are quite feasible
Despite the time lapse since the invention of ketone peroxides, they have not 15 found any commercial use as an ignition improver On the contrary, the presently used commercial products to improve the ignition of (diesel) fuels are di-tert-butyl peroxide and 2-ethylhexyl nitrate, as taught by Chemtech. 8-97, pp 38-41 However, these products suffer from various disadvantages Nitrates may lead to NOx formation upon combustion, while di-tert-butyl peroxide has a 20 low flash-point and high volatility, which can lead to various safety hazards Nor do most peroxides possess long-term (thermal) stability in diesel fuels Especially at higher temperatures such as can be encountered in fuel systems, decreased thermal stability can lead to gum formation or other degradation of the fuel Also, the decomposition products of peroxides generally are (partly) 25 alcoholic in nature, which tends to increase the undesired water uptake by the fuel. Furthermore, most of the peroxides used thus far suffer from a relatively low active matter content Also, the price/performance ratio of most peroxides stands in the way of their being widely introduced into (diesel) fuels In this respect it is noted that the unsatisfactory performance of dimeric cyclic ketone 30 peroxides as disclosed in, for instance, FR-B-862,974 is considered to lead to
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an unacceptable price/performance ratio of these products Furthermore, the dimeric structure of conventional cyclic ketone peroxides may present a safety hazard, due to the volatility and the low flash point of such products In consequence, there still is a need for fuels with improved characteristics
Surprisingly, some of the peroxide compositions disclosed in WO 96/03397 were found to be very suitable for improving the ignition characteristics of fuels WO 96/03397 relates to numerous formulations of cyclic ketone peroxides, as described below, comprising a variety of phlegmatizers However, this patent 10 application does not disclose or suggest the use of cyclic ketone peroxides in fuels A comparison between the cyclic ketone peroxides of WO 96/03397 that perform well and the cyclic ketone peroxides according to, for example, FR-B-862,974 showed that the surprising performance is related to the nature of the cyclic ketone peroxide that is used Therefore, the invention resides in the 15 proper selection of the ketone peroxide used to improve the fuel
The fuel according to the invention is characterized in that it comprises from 0 001 to 10 percent by weight of one or more cyclic ketone peroxides selected from the group of peroxides represented by formula I.
\ /R2 /Sr I
.o.
-°\ R3
\ / -A.
/'
^ R5
(I)
wherein R.,, R3, and R5 are independently selected from the group consisting of hydrogen, C^Cjq alkyl, C3-C20 cycloalkyl, C6-C20 aryl, C7-C20 aralkyl, and C7-C20 alkaryl, which groups may include linear or branched alkyl moieties, and R2, R4, 25 and R6 are independently selected from the group consisting of hydrogen, C2-C20 alkyl, C3-C20 cycloalkyl, C6-C20 aryl, C7-C20 aralkyl, and C7-C20 alkaryl, which groups may include linear or branched alkyl moieties, and each of R^Re may
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optionally be substituted with one or more groups selected from hydroxy, alkoxy, linear or branched alkyl, aryloxy, ester, carboxy, nitrile, and amido, with the proviso that said peroxides make up at least 35% by weight of all cyclic ketone peroxides in the fuel
The improved fuels according to the invention do not suffer from most of the disadvantages mentioned above More specifically, it was found that the use of the cyclic ketone peroxides of formula I results in fuels with an exceptionally good performance with respect to ignition timing and the correlated cetane 10 number, good miscibility, good chemical stability, le resistance to oxygen, acids, and metal oxides such as rust, and good compatibility with other parts of the fuel system, such as metals, rubber fittings, gaskets, and hoses
Preferably, the cyclic ketone peroxides according to the invention consist of 15 oxygen, carbon, and hydrogen atoms, so as to avoid an adverse effect on the NOx emission upon combustion of the fuel into which they are incorporated More preferably, the cyclic ketone peroxides according to formula I are derived from at least one ketone with a molecular weight greater than acetone, such that the total number of carbon atoms of the molecule is greater than 6 The 20 use of such ketones of higher molecular weight will have a positive effect on the solubility of said cyclic ketone peroxide in a fuel and was found to more effective as an ignition improver, based on the amount of active oxygen added Preferably, a ketone with at least 4 carbon atoms, more preferably with at least 5 carbon atoms, is used to produce the cyclic ketone peroxide used according 25 to the invention Also, the total number of carbon atoms in the cyclic ketone peroxide according to the invention preferably is less than 40, more preferably less than 30, and most preferably less than 25 Otherwise the molecular weight will be too high, necessitating a high dosing level of the peroxide to the fuel, which is economically unattractive. Incidentally, it is noted that if mixtures of 30 ketones comprising acetone are used, then some undesired dimeric and
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trimeric acetone peroxides will be formed Such cyclic acetone peroxides can precipitate at lower temperatures when used in a fuel, particularly in a diesel fuel, and thus may necessitate a further purification step Hence also the use of acetone in mixtures of ketones is undesired Furthermore, although mixtures of 5 ketones can be used to make the cyclic ketone peroxides according to the invention, it is preferred that just one ketone is used, such that R,=R3=R5 and R2=R<=R6 Such cyclic ketone peroxides are, inter alia, more easily produced and less prone to changes in composition due to changing process conditions. Hence, the quality of the ignition improvers thus formed is more easily 10 controlled
The ignition time improving cyclic ketone peroxide(s) preferably is/are present in such an amount that the self-ignition time of treated fuel is shorter in a model test as described below than the self-ignition time of untreated fuel. More 15 preferably, a reduction of the self-ignition time by more than 10% is observed at 270°C in said test Even more preferably, the reduction of the self-ignition time is more than 25% at this test temperature. Most preferred is a reduction of at least 50% of the self-ignition time at 270°C
Preferably, one or more of the cyclic ketone peroxides according to formula I are present in the final fuel formulation in an amount of between 0 025 and 5 percent by weight (% w/w) Most preferred is a concentration of cyclic peroxide of formula I in the fuel of between 0 05 and 2.5% w/w. Less peroxide will not result in any noticeable improvement of the ignition characteristics of the fuel, 25 whereas a higher amount may prove to be unsafe or uneconomical
The term fuels, as used throughout this document, is meant to encompass all hydrocarbon distillates and residue-containing oils for use in combustion engines and which distill between the kerosene fraction and the lubricating oil 30 fraction of petroleum The fuel may comprise the usual additives, such as anti-
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foam agents, injector cleaning agents, drying agents, cloud point depressants, also known as anti-gel agents, algea control agents, lubricants, dyes, and . oxidation inhibitors, but may also comprise further ignition improving or combustion improving additives, provided that such additives do not adversely 5 affect the storage stability of the final fuel composition according to the invention. A preferred fuel is diesel fuel
In a second embodiment, the invention relates to a process to make the ignition improved fuels To this end, an appropriate cyclic ketone peroxide composition 10 is combined with a fuel, or else the cyclic ketone peroxide is produced directly in said fuel
The cyclic ketone peroxide(s) can be produced as described in WO 96/03397. It is disclosed there how by changing the reaction conditions, the composition 15 of the resulting cyclic ketone peroxide can be controlled The trimeric cyclic ketone peroxides according to formula I preferably are formed when mild reaction conditions are chosen, e g. by lowering the amount of acid used in the process, lowering the temperature, reacting for a short period of time, and/or dosing the hydrogen peroxide and the acid at the same time Furthermore, the 20 production of the trimeric compound is favoured when less water is used in the reaction, probably because less trimeric compound is hydrolyzed to the dimeric compound. The exact conditions will depend on the type of ketone that is used and the concentration of the various reactants However, the skilled person will have no problem in determining which process conditions are to be selected for 25 producing the cyclic ketone peroxides as used in the invention Preferably, however, the process temperature ranges from 0-80°C, more preferably 5-60°C, and most preferably 20-45°C to allow for a cost-efficient process.
Suitable ketones for use in the synthesis of cyclic ketone peroxides as used in 30 the invention include, for example, acetone, acetophenone, methyl-n-amyl
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ketone, ethylbutyl ketone, ethylpropyl ketone, methylisoamyl ketone, methylheptyl ketone, methylhexyl ketone, ethylamyl ketone, dimethyl ketone, diethylketone, dipropyl ketone, methylethyl ketone, methylisobutyl ketone, methylisopropyl ketone, methylpropyl ketone, methyl-tert-butyl ketone, 5 isobutylheptyl ketone, dnsobutyl ketone, 2,4-pentanedione, 2,4-hexanedione, 2,4-heptanedione, 3,5-heptanedione, 3,5-octanedione, 5-methyl-2,4-hexanedione, 2,6-dimethyl-3,5-heptanedione, 2,4-octanedione, 5,5-dimethyl-2,4-hexanedione, 6-methyl-2,4-heptanedione, 1-phenyl-1,3-butanedione, 1-phenyl-1,3-pentanedione, 1,3-diphenyl-1,3-propanedione, 1 -phenyl-2,4-10 pentanedione, methylbenzyl ketone, phenylmethyl ketone, phenylethyl ketone, and coupling products thereof. Of course, other ketones having appropriate R groups corresponding to the peroxides of formula I can also be employed, as well as mixtures of two or more different ketones
Examples of preferred peroxides of formula I for use in accordance with the present invention are the cyclic ketone peroxides derived from methyl-n-amyl ketone, ethylbutyl ketone, ethylpropyl ketone, methylheptyl ketone, methylhexyl ketone, ethylamyl ketone, methylpropyl ketone, diethyl ketone, methylethyl ketone, isomers of these ketones, and mixtures thereof More preferably, the 20 peroxides of formula I are based on at least one ketone selected from the group consisting of methyl-n-amyl ketone, ethylbutyl ketone, ethylpropyl ketone, methylheptyl ketone, methylhexyl ketone, ethylamyl ketone, methylpropyl ketone, diethyl ketone, methylethyl ketone, and one or more isomers of these ketones, such as methyl-isobutyl ketone and methylisopropyl ketone
The peroxides can be prepared, transported, stored, and applied in any solid or liquid form, but solutions in a non-halogenated liquid phlegmatiser are preferred These compositions can then be combined with the fuel. It should be noted that certain phlegmatizers may not be suitable for use in all of the ketone 30 peroxide compositions of the present invention. More particularly, in order to
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obtain a safe composition, the phlegmatizer should have a certain minimum flash point and minimum boiling point relative to the decomposition temperature of the ketone peroxide, such that the phlegmatizer cannot be boiled off leaving a concentrated, unsafe ketone peroxide composition
Preferred phlegmatizers are selected from the group consisting of hydrocarbons, such as (diesel) fuel, paraffinic and white oils, oxygenated hydrocarbons, such as ethers, aldehydes, epoxides, esters, ketones, alcohols, and organic peroxides, such as linear ketone peroxides and di-tert-butyl 10 peroxide, alkyl nitrates, such as 2-ethylhexyl nitrate, and mixtures thereof Examples of preferred liquid phlegmatizers for the cyclic ketone peroxides include alkanots, in particular higher aliphatic alkanols, cycloalkanols, alkylene glycols, alkylene glycol monoalkyl ethers, ethers, in particular methyl tert-butyl ether, aldehydes, ketones, epoxides, esters, hydrocarbon solvents, including 15 toluene, xylene, (diesel) fuel, paraffinic oils, and white oils More preferred liquid phlegmatizers are ethers and hydrocarbons Most preferably, a fuel is used as the phlegmatiser A concentrated cyclic ketone peroxide composition is very suitable for further dilution with fuel in order to obtain a fuel comprising an ignition improving amount of said peroxide
The fuel according to the invention may contain just peroxides of formula I as the ignition improver. However, they may also be combined with other ignition improvers, such as conventional di-tert-butyl peroxide and/or 2-ethylhexyl nitrate. If the peroxides of formula I are used together with other cyclic ketone 25 peroxide ignition improvers, then it is preferred that they make up at least 40% w/w, more preferably at least 45% w/w, more preferably at least 50% w/w, more preferably at least 66% w/w, and even more preferably more than 75% w/w, based on the weight of all cyclic ketone peroxides in the fuel. Most preferred are compositions in which more than 80% w/w of the weight of all cyclic ketone 30 peroxides can be attributed to cyclic ketone peroxides according to formula I,
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9
because the ignition properties of such fuels is most efficiently improved If only cyclic ketone peroxides consisting essentially of a mixture of dimeric and trimeric compounds (according to formula I) are used in the fuel, then the indicated preferred ranges show that the ratio of dimeric to trimeric compounds 5 in the fuel is lower than about 2.1, more preferably lower than about 3 2, more preferably lower than about 5 4, more preferably lower than about 11, more preferably lower than 1 2, more preferably lower than about 1 3, and most preferably lower than about 1 4.
To avoid safety hazards, it is preferred that the cyclic ketone peroxide composition used to make up the claimed fuels is not essentially pure cyclic ketone peroxide More preferably, the compositions comprise less than 99% w/w, more preferably less than 90% w/w, and even more preferably less than 85% w/w of cyclic ketone peroxide, all based on the weight of the total 15 formulation Most preferably, the cyclic ketone peroxide composition that is used to make fuels according to the invention comprises less than 75% w/w of cyclic ketone peroxide, based on the weight of the total composition
Alternatively, the cyclic ketone peroxides can be prepared in a fuel, which can 20 be the fuel the ignition characteristics of which are to be improved, in the desired concentration of between 0 01 and 10% w/w To this end, the conventional reactants and catalyst(s) are introduced into untreated fuel and reacted Subsequently, the ignition improved fuel is separated from contaminants and process water, optionally washed, and optionally dried, all in 25 a conventional manner In this preparation, the streams to be processed are quite large in volume, but the handling of a peroxide concentrate can be avoided
The invention is elucidated by the following examples.
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WO 99/32584 PCT/EP98/08131
Examples
Materials used"
Isopar® M Cychc-MEKP-1
Cyclic-MEKP-2
2-EHN Trigonox® B DF-0
hydrocarbon phlegmatizer ex Exxon Chemical cyclic methyl-ethyl-ketone peroxide (41% w/w in Isopar M) ex Akzo Nobel 93% trimeric, 7% dimeric compounds (GC area%)
cyclic methyl-ethyl-ketone peroxide (29 7% w/w in Diesel 1) ex Akzo Nobel 85% trimeric, 15% dimeric compounds (GC area%)
2-ethylhexyl nitrate (97%) ex Aldrich di-tert-butyl peroxide ex Akzo Nobel
Low sulfur Diesel #2 ex Octel with a boiling range of 163-
370°C, a flash point of 51 6-65 5°C (D-93), and an auto-
ignition temperature of 257°C (E-659)
Procedure
The performance of ignition improvers in the process according to the invention 20 was evaluated by means of the following screening method'
• mixing the ignition improver in the specified amount with the diesel fuel at room temperature,
• injecting a sample of 100 j^l or 250 jxl by means of a syringe into an apparatus according to DIN 51794, which is controlled at a temperature of
270°C, and measuring the time that elapses before the sample ignites.
Alternatively, the cetane number of the fuel is measured according to method ASTM D-613
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The active oxygen content of the peroxides and fuels was analyzed by means of conventional analytical techniques such as lodometric titration and gas chromatographic analysis More specifically, linear ketone peroxides were analyzed by means of method Jo/97 3 and the total amount of active oxygen 5 was analyzed by means of method Jo/97 2 The ratio of dimeric to trimeric ketone peroxide was analyzed by means of method GC 97 8 These methods are available upon request from Akzo Nobel,
Predominantly trimeric cyclic methylisobutyl ketone peroxide to be used as a 10 fuel additive was produced by adding 97.1 g of hydrogen peroxide (70%) to a stirred mixture of 200 g of methylisobutyl ketone, 100 g of Isopar® M, and 196 g of sulfuric acid (50%) over a period of 20 minutes, under a temperature of 20-25°C The mixture was then stirred for another 3 hours at 40°C and for 18 hours at 30°C. The organic phase was separated, washed with water and 15 caustic and sulfite solutions, respectively, and dried over magnesium sulfate dihydrate This process resulted in 235 g of an organic liquid with a total active oxygen content of 2 14%, of which 2 07% was cyclic methylisobutyl ketone peroxide and less than 0 07% was linear methylisobutyl ketone peroxide The ratio of dimeric to trimeric cyclic compounds was 12 88 GC area%
Example 1
Diesel fuel DF0 was mixed with sufficient cyclic-MEKP-1 to give a 1% w/w concentration of cyclic ketone peroxide in the diesel fuel.
Both the 100 |il and the 250 (al sample, when tested as described above, 25 ignited after 3 0 seconds The cetane number of the ignition improved fuel was greater than 73.7
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Comparative Examples A-D
Example 1 was repeated, except that no or other conventional ignition improvers were used The compounds used, their concentration in the diesel fuel, and the results of the tests are incorporated into the following table
Comparative
Ignition
Concentration
Time to ignition (s)
Cetane
Example improver in the fuel
100nl
250^1
Number
A
None
0
106
11 1
54 7
B
2-EHN
1 %w/w
28
2.7
70 9
C
Trigonox B
1 %w/w
1 1
1 2
69 7
D
2-EHN and
1 %w/w each
1 1
1 1
n d
Trigonox B
n d = not determined
Example B was repeated using 0 787% w/w of 2-EHN and diesel 2 The ignition improved fuel (cetane number about 61) was evaluated according to 10 Conradson test ASTM-D189. When converted to equivalent values for the Ramsbottom residue test, 0 2% w/w of carbon deposits was formed
Comparative Examples E-G
The Examples 1, 3, and 5 of FR-862 974 were reworked as Comparative 15 Examples E-G, respectively, except that Example 5 was not reworked in a continuous but in a discontinuous fashion.
The dissolution and performance of the cyclic acetone peroxide of Comparative Example E in fuel was unsatisfactory
The cyclic butanone peroxides of Comparative Examples F and G contained 90 20 and 76% (GC area%) of dimeric butanone peroxide and 10 and 24% (GC area%) of trimeric butanone peroxide, based on the GC area of cyclic ketone peroxides.
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Examples 2-7 and Comparative Examples H-J
Using three types of diesel fuel, various ketone peroxides were evaluated for their influence on the cetane number In Examples 2-6 cyclic-MEKP-2 was used as an ignition fuel improver, while in Example 7 the cyclic methylisobutyl ketone peroxide as prepared above was used In Comparative Example H, no ketone peroxide was used, in Comparative Example I Butanox®M50 ex Akzo Nobel, a predominantly linear methylethyl ketone peroxide, was used, while in Comparative Example J, Trigonox®233 ex Akzo Nobel, a predominantly linear methylisobutyl ketone peroxide, was used.
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The diesel fuels that were used are characterized by the following
Diesel
1
2
3
Supplied as
Treated LGO
Treated LCO/LGO mix
Treated LGO
Sulfur
PPm
157
293
223
Density (at15°C)
g/ml
0 8273
0 8505
0.8400
Cetane index
58.83
49 36
57 87
Aromatic compounds
Mono
%w/w
22 7
36 3
0
Di
%w/w
27
6.7
38
Tri
%w/w
0 1
05
02
Saturates
%w/w
74.5
56.5
71 0
Sim Dist (ASTM D-2887)
IBP
°C
125.4
120.2
134 2
%
°C
206 9
201 4
235 3
%
233.0
227 1
263.1
%
252.7
246.1
280.7
40
°C
269.9
262.1
295 7
50
°C
286 6
278.2
309 6
60
°C
302.3
294.9
324 1
70
°C
318 1
311 4
341.6
80
°C
338 7
330.6
360.2
90
°C
365 5
356.3
385 7
FBP
°C
427 1
425 8
450 9
LGO = light gas oil LCO = light cycling oil
Printed from Mimosa
The following results were obtained
Example
Peroxide
Cetane number
%w/w
Type
Diesel 1
Diesel 2
Diesel 3
2
0 0596
Cyclic MEKP
61 5
49 5
60 4
3
0 179
Cyclic MEKP
65 0
52 5
65 3
4
0 298
Cyclic MEKP
66 1
56 7
66 1
0 447
Cyclic MEKP
70.6
59.0
69 9
6
0 596
Cyclic MEKP
73 5
61 4
74 0
7
0 397
Cyclic MiBKP
n d n d.
67 0
H
0
None
58.9
46 7
57.8
I
0.200
Linear MEKP
n d
49 6
n d
J
0 293
Linear MiBKP
nd
51 0
n.d n d = not determined
Obviously, on an equal active oxygen basis, the cyclic ketone peroxides of the higher ketones are more efficient at improving the cetane number
Also, the product of Example 6 in diesel 2 was evaluated according to Conradson test ASTM-D189. When converted to equivalent values for the Ramsbottom residue test, 0.05% w/w of carbon deposits was formed, which is much better than the result obtained in Comparative Example B
Example 8
A fuel according to the invention was prepared by adding 19.4 g of hydrogen peroxide to a stirred mixture of 27 g of diesel 1, 28.8 g of methylethyl ketone peroxide, and 14 0 g of sulfuric acid over a period of 20 minutes, while 15 maintaining a temperature of about 20°C The mixture was then stirred for another 90 minutes at 20°C, and the two layers were separated The organic layer was washed with 25 g of a 6% w/w solution of sodium hydrogen carbonate, dried over magnesium sulfate dihydrate, and filtered The product
Printed from Mimosa
Claims (1)
- WO 99/32584 PCT/EP98/08131 16 contained predominantly cyclic methylethyl ketone peroxide with a ratio of dimeric/trimeric compounds of 13 87 GC area% Example 9 and Comparative Example K 5 In order to demonstrate the differences in effect of dimeric and trimeric cyclic ketone peroxides when used as a fuel ignition improver, a diesel fuel was doped with 0.595% w/w of cyclic methylethyl ketone peroxide In Example 9, a product was used with a ratio of dimeric/trimeric compounds of 5 6 94 4 (GC area%), while in Comparative Example K this ratio was 98 6 1 4 (GC area%) 10 The cetane number of the untreated fuel was 54 7 The cetane number of the fuel of Example 9 was 69.3 The cetane number of the fuels of Comparative Example K was 64.7 Printed from Mimosa WO 99/32584 PCT/EP98/08131 17 Claims INTELLECTUAL PROPERTY OFFICE OF N Z. 1 5 nov 2001 RECEIVED V L (/ ) n 1 1 Fuel with improved ignition characteristics comprising one or more cyclic ketone peroxides, wherein it comprises from 0.01 to 10 percent by weight of one or more cyclic ketone peroxides selected from the group of peroxides represented by formula I R, R2 \ / 0 1 cx O' -O- /c\ R6 R5 -\ /"■ -A. (I) wherein R1( R3, and R5 are independently selected from the group consisting of hydrogen, ^Ikyl, ^3"^2o cycloalkyl > C6-C2o aryl, C7-C2o 10 aralkyl, and C7-C20 alkaryl, which groups may include linear or branched alkyl moieties; R2, R4, and R6 are independently selected from the group consisting of hydrogen, C2-C2Q alkyl, C3-C20 cycloalkyl, C6-C20 aryl, C7-C20 aralkyl, and C7-C20 alkaryl, which groups may include linear or branched alkyl moieties; and each of R-,-R6 may optionally be substituted with one or 15 more groups selected from hydroxy, alkoxy, linear or branched alkyl, aryioxy, ester, carboxy, nitnle, and amido, with the proviso that said peroxides make up at least 35% by weight of all cyclic ketone peroxides in the fuel. 20 2. A fuel according to claim 1, wherein the final concentration of the peroxide(s) according to formula I m the fuel is between 0 025 and 5 percent by weight, based on the weight of the total formulation 3 A fuel according to claim 1 or 2, wherein at least one of the 25 cyclic ketone peroxides in the fuei is derived from one or more ketones selected from the group consisting of acetone, methyl-n-amyl ketone, ethylbutyl ketone, ethylpropyl ketone, methylheptyl ketone, methylhexyl WO 99/32584 PCT/EP98/08131 18 50 4. 5 0 10 5 15 6. 20 ketone, ethylamyl ketone, methylpropyl ketone, diethyl ketone, methylethyl ketone, isomers of these ketones, and mixtures thereof A fuel according to claim 3, wherein it comprises a cyclic ketone peroxide of formula I derived from at least one ketone selected from the group consisting of methyl-n-amyl ketone, ethylbutyl ketone, ethylpropyl ketone, methylheptyl ketone, methylhexyl ketone, ethylamyl ketone, methylpropyl ketone, diethyl ketone, methylethyl ketone, and isomers thereof A fuel according to claim 4, wherein the cyclic ketone peroxide of formula I is derived from one ketone selected from the group consisting of methylbutyl ketone, methyl-n-amyl ketone, ethylbutyl ketone, ethylpropyl ketone, methylheptyl ketone, methylhexyl ketone, ethylamyl ketone, methylpropyl ketone, diethyl ketone, methylethyl ketone, and isomers thereof A fuel according to any one of claims 1-5, wherein the amount of cyclic ketone peroxide of formula I in the fuel is at least 40% by weight, preferably at least 50% by weight, and most preferably more than 80% by weight, based on the weight of all cyclic ketone peroxide in the fuel A fuel according to any one of claims 1-6, wherein the cyclic ketone peroxide of formula I is selected from the group consisting of cyclic methylethyl ketone peroxide, cyclic methylisobutyl ketone peroxide, and cyclic methylisopropyl ketone peroxide A fuel according to any one of claims 1-7, wherein the fuel is a diesel fuel. INTELLECTUAL PROPERTY OFFICE OF N.Z. 1 5 nov 2001 RECEIVED WO 99/32584 19 010 15 20 9 Process to make an ignition improved fuel according to any one of claims 1-8, wherein a cyclic ketone peroxide composition is combined with a fuel, which cyclic ketone peroxide composition comprises at least 35% by weight, based on the weight of all cyclic ketone peroxides, of one or more cyclic ketone peroxides selected from peroxides represented by formula I and further comprises one or more non-halogenated phlegmatizers selected from the group consisting of hydrocarbons, oxygenated hydrocarbons, alkyl nitrates, and mixtures thereof 10. A process according to claim 9 wherein a phlegmatizer is used that is selected from the group consisting of alkanols, cycloalkanols, alkylene glycols, alkylene glycol monoalkyl ethers, ethers, aldehydes, ketones, epoxides, esters, hydrocarbons, and mixtures thereof 11 A process according to claim 10 wherein the phlegmatizer is selected from ethers or hydrocarbons. 12 A process according to claim 10 or claim 11 wherein the phlegmatizer is selected from a hydrocarbon fuel 13. A process according to claim 12 wherein the hydrocarbon fuel is a diesel fuel 14 A process to make an ignition improved fuel according to any one of claims 1-8, wherein the cyclic ketone peroxide is produced in a concentration from 0.01 to 10 percent by weight in the fuel. 15 Use of a fuel according to any one of claims 1-8 in a combustion engine to reduce the emission of pollutants. INTELLECTUAL PROPERTY OFFICE OF NZ. 1 5 nov 2001 received ^ K U 20 16 Fuel according to claim 1, substantially as herein described with reference to 1 to 9. 17. Fuel according to any one of claims 1 to 8, substantially as herein described. 18. A process according to claim 9, substantially as herein described with reference to the examples 1 to 9 19. A process according to any one of claims 9 to 14 substantially as herein described. 20 Fuel obtained by the process according to claim 9, substantially as herein described with reference to the examples 1 to 9. 21. Fuel obtained by a process according to any one of claims 9 to 14, substantially as herein described INTELLECTUAL PROPERTY OFFICE OF N.Z. 1 5 nov 2001 received
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP97204051 | 1997-12-22 | ||
US7205098P | 1998-01-21 | 1998-01-21 | |
PCT/EP1998/008131 WO1999032584A1 (en) | 1997-12-22 | 1998-12-14 | Ignition improved fuels |
Publications (1)
Publication Number | Publication Date |
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NZ505170A true NZ505170A (en) | 2002-02-01 |
Family
ID=8229100
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NZ505170A NZ505170A (en) | 1997-12-22 | 1998-12-14 | Ignition improved fuels doped with a cyclic ketone peroxide |
Country Status (13)
Country | Link |
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EP (1) | EP1042433A1 (en) |
JP (1) | JP2001527124A (en) |
CN (1) | CN1121479C (en) |
AU (1) | AU2271399A (en) |
BR (1) | BR9814373A (en) |
CA (1) | CA2315683A1 (en) |
HU (1) | HUP0100654A2 (en) |
ID (1) | ID25464A (en) |
NZ (1) | NZ505170A (en) |
PL (1) | PL341331A1 (en) |
TR (1) | TR200001920T2 (en) |
WO (1) | WO1999032584A1 (en) |
ZA (1) | ZA9811722B (en) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
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AU2001293756A1 (en) * | 2000-08-15 | 2002-02-25 | Akzo Nobel N.V. | Use of trioxepans in ignition improved fuels |
EP1447404A1 (en) * | 2003-02-13 | 2004-08-18 | Akzo Nobel N.V. | Improved cyclic ketone peroxide compositions |
BRPI0407472B1 (en) * | 2003-02-13 | 2015-07-07 | Akzo Nobel Nv | Storage stable cyclic ketone peroxide compositions |
DE102009016492A1 (en) * | 2009-04-06 | 2010-10-14 | Bundesanstalt für Materialforschung und -Prüfung (BAM) | Fuel and use of the same |
US8621843B2 (en) | 2009-10-30 | 2014-01-07 | Bp Corporation North America Inc. | Composition and method for reducing NOx emissions from diesel engines at minimum fuel consumption |
DE102013112821A1 (en) | 2012-11-30 | 2014-06-05 | Shell Internationale Research Maatschappij B.V. | Fuel Compositions |
EP2935533B1 (en) | 2012-12-21 | 2019-03-27 | Shell International Research Maatschappij B.V. | Use of an organic sunscreen compound in a diesel fuel composition |
MY173652A (en) | 2013-10-24 | 2020-02-13 | Shell Int Research | Liquid fuel compositions |
WO2015091458A1 (en) | 2013-12-16 | 2015-06-25 | Shell Internationale Research Maatschappij B.V. | Liquid fuel compositions |
KR102384111B1 (en) | 2014-03-11 | 2022-04-06 | 누리온 케미칼즈 인터내셔널 비.브이. | Cyclic ketone peroxide composition |
EP2949732B1 (en) | 2014-05-28 | 2018-06-20 | Shell International Research Maatschappij B.V. | Use of an oxanilide compound in a diesel fuel composition for the purpose of modifying the ignition delay and/or the burn period |
EP3088495A1 (en) | 2015-04-28 | 2016-11-02 | United Initiators GmbH & Co. KG | Use of a fuel additive in diesel fuel for removing deposits in a diesel engine |
MY188997A (en) | 2015-11-11 | 2022-01-17 | Shell Int Research | Process for preparing a diesel fuel composition |
CN106221834B (en) * | 2016-08-22 | 2018-01-26 | 天津市苏同兴盛环保科技有限公司 | Low-temperature methanol starts additive |
WO2018077976A1 (en) | 2016-10-27 | 2018-05-03 | Shell Internationale Research Maatschappij B.V. | Process for preparing an automotive gasoil |
WO2018206729A1 (en) | 2017-05-11 | 2018-11-15 | Shell Internationale Research Maatschappij B.V. | Process for preparing an automotive gas oil fraction |
MX2020013813A (en) | 2018-07-02 | 2021-03-09 | Shell Int Research | Liquid fuel compositions. |
IT202000020368A1 (en) * | 2020-08-24 | 2022-02-24 | Cesare Pedrazzini | ADDITIVE TO REDUCE THE PARTICULATE IN THE EMISSIONS DERIVING FROM THE COMBUSTION OF DIESEL AND FUEL OIL AND THE FUEL COMPOSITION THAT CONTAINS THEM |
CN114686278A (en) * | 2022-02-18 | 2022-07-01 | 任国辉 | Use of cyclic peroxides in petroleum products |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE617492C (en) * | 1934-05-26 | 1935-08-20 | Bataafsche Petroleum | Process for the production of fuel oil for diesel and semi-diesel engines |
FR862070A (en) * | 1938-12-02 | 1941-02-26 | Bataafsche Petroleum | Process for the preparation of heteropolymeric aliphatic ketone peroxides and liquid fuels containing these peroxides |
FR862974A (en) * | 1940-01-18 | 1941-03-20 | Bataafsche Petroleum | Process for the preparation of peroxides of aliphatic ketones and liquid fuels having improved ignition quality |
US3003000A (en) * | 1959-07-01 | 1961-10-03 | Research Corp | Organic peroxides |
US3116300A (en) * | 1960-11-18 | 1963-12-31 | Pure Oil Co | Process for preparing dicyclo-alkylidene diperoxides |
RU2154649C2 (en) * | 1994-07-21 | 2000-08-20 | Акцо Нобель Н.В. | Composition based on cyclic ketone peroxides |
-
1998
- 1998-12-14 CA CA002315683A patent/CA2315683A1/en not_active Abandoned
- 1998-12-14 WO PCT/EP1998/008131 patent/WO1999032584A1/en not_active Application Discontinuation
- 1998-12-14 ID IDW20001206A patent/ID25464A/en unknown
- 1998-12-14 NZ NZ505170A patent/NZ505170A/en unknown
- 1998-12-14 TR TR2000/01920T patent/TR200001920T2/en unknown
- 1998-12-14 BR BR9814373-5A patent/BR9814373A/en not_active IP Right Cessation
- 1998-12-14 JP JP2000525509A patent/JP2001527124A/en active Pending
- 1998-12-14 PL PL98341331A patent/PL341331A1/en unknown
- 1998-12-14 EP EP98966311A patent/EP1042433A1/en not_active Ceased
- 1998-12-14 AU AU22713/99A patent/AU2271399A/en not_active Abandoned
- 1998-12-14 HU HU0100654A patent/HUP0100654A2/en unknown
- 1998-12-14 CN CN98812578A patent/CN1121479C/en not_active Expired - Fee Related
- 1998-12-21 ZA ZA9811722A patent/ZA9811722B/en unknown
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CN1283218A (en) | 2001-02-07 |
EP1042433A1 (en) | 2000-10-11 |
HUP0100654A2 (en) | 2001-06-28 |
ID25464A (en) | 2000-10-05 |
CA2315683A1 (en) | 1999-07-01 |
PL341331A1 (en) | 2001-04-09 |
AU2271399A (en) | 1999-07-12 |
JP2001527124A (en) | 2001-12-25 |
WO1999032584A1 (en) | 1999-07-01 |
BR9814373A (en) | 2000-10-10 |
TR200001920T2 (en) | 2000-12-21 |
ZA9811722B (en) | 1999-06-21 |
CN1121479C (en) | 2003-09-17 |
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