US20030110684A1 - Extremely stable diesel fuel compositions - Google Patents
Extremely stable diesel fuel compositions Download PDFInfo
- Publication number
- US20030110684A1 US20030110684A1 US10/020,411 US2041101A US2003110684A1 US 20030110684 A1 US20030110684 A1 US 20030110684A1 US 2041101 A US2041101 A US 2041101A US 2003110684 A1 US2003110684 A1 US 2003110684A1
- Authority
- US
- United States
- Prior art keywords
- nitrate
- composition
- fuel
- diesel fuel
- indoles
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000002283 diesel fuel Substances 0.000 title claims abstract description 68
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 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 49
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims abstract description 45
- 229910002651 NO3 Inorganic materials 0.000 claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 27
- 150000002475 indoles Chemical class 0.000 claims abstract description 27
- -1 thioacids Chemical class 0.000 claims abstract description 27
- 150000003568 thioethers Chemical class 0.000 claims abstract description 27
- 150000002019 disulfides Chemical class 0.000 claims abstract description 26
- 150000002476 indolines Chemical class 0.000 claims abstract description 26
- 150000003233 pyrroles Chemical class 0.000 claims abstract description 26
- 150000003460 sulfonic acids Chemical class 0.000 claims abstract description 26
- 238000004062 sedimentation Methods 0.000 claims abstract description 17
- 238000002845 discoloration Methods 0.000 claims abstract description 15
- 239000000446 fuel Substances 0.000 claims description 47
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 239000011593 sulfur Substances 0.000 claims description 29
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 238000009835 boiling Methods 0.000 claims description 16
- NKRVGWFEFKCZAP-UHFFFAOYSA-N 2-ethylhexyl nitrate Chemical compound CCCCC(CC)CO[N+]([O-])=O NKRVGWFEFKCZAP-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- HSNWZBCBUUSSQD-UHFFFAOYSA-N amyl nitrate Chemical compound CCCCCO[N+]([O-])=O HSNWZBCBUUSSQD-UHFFFAOYSA-N 0.000 claims description 4
- PSTVZBXGCKLSQA-UHFFFAOYSA-N (1-methylcyclohexyl) nitrate Chemical compound [O-][N+](=O)OC1(C)CCCCC1 PSTVZBXGCKLSQA-UHFFFAOYSA-N 0.000 claims description 2
- OZUCSFZQPDHULO-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl nitrate Chemical compound CCOCCOCCO[N+]([O-])=O OZUCSFZQPDHULO-UHFFFAOYSA-N 0.000 claims description 2
- TXPURXMTKXRAMV-UHFFFAOYSA-N 2-[2-[2-(2-nitrooxyethoxy)ethoxy]ethoxy]ethyl nitrate Chemical compound [O-][N+](=O)OCCOCCOCCOCCO[N+]([O-])=O TXPURXMTKXRAMV-UHFFFAOYSA-N 0.000 claims description 2
- GDNQXPDYGNUKII-UHFFFAOYSA-N 2-ethoxyethyl nitrate Chemical compound CCOCCO[N+]([O-])=O GDNQXPDYGNUKII-UHFFFAOYSA-N 0.000 claims description 2
- LNNXFUZKZLXPOF-UHFFFAOYSA-N 2-methylpropyl nitrate Chemical compound CC(C)CO[N+]([O-])=O LNNXFUZKZLXPOF-UHFFFAOYSA-N 0.000 claims description 2
- NNKQLUVBPJEUOR-UHFFFAOYSA-N 3-ethynylaniline Chemical compound NC1=CC=CC(C#C)=C1 NNKQLUVBPJEUOR-UHFFFAOYSA-N 0.000 claims description 2
- NTHGIYFSMNNHSC-UHFFFAOYSA-N 3-methylbutyl nitrate Chemical compound CC(C)CCO[N+]([O-])=O NTHGIYFSMNNHSC-UHFFFAOYSA-N 0.000 claims description 2
- DYONNFFVDNILGI-UHFFFAOYSA-N butan-2-yl nitrate Chemical compound CCC(C)O[N+]([O-])=O DYONNFFVDNILGI-UHFFFAOYSA-N 0.000 claims description 2
- QQHZPQUHCAKSOL-UHFFFAOYSA-N butyl nitrate Chemical compound CCCCO[N+]([O-])=O QQHZPQUHCAKSOL-UHFFFAOYSA-N 0.000 claims description 2
- JYKKNPZBKRPDDP-UHFFFAOYSA-N cyclododecyl nitrate Chemical compound [O-][N+](=O)OC1CCCCCCCCCCC1 JYKKNPZBKRPDDP-UHFFFAOYSA-N 0.000 claims description 2
- HLYOOCIMLHNMOG-UHFFFAOYSA-N cyclohexyl nitrate Chemical compound [O-][N+](=O)OC1CCCCC1 HLYOOCIMLHNMOG-UHFFFAOYSA-N 0.000 claims description 2
- DDBCVXXAMXPHKF-UHFFFAOYSA-N cyclopentyl nitrate Chemical compound [O-][N+](=O)OC1CCCC1 DDBCVXXAMXPHKF-UHFFFAOYSA-N 0.000 claims description 2
- UEFBRXQBUTYIJI-UHFFFAOYSA-N decyl nitrate Chemical compound CCCCCCCCCCO[N+]([O-])=O UEFBRXQBUTYIJI-UHFFFAOYSA-N 0.000 claims description 2
- PAWHIGFHUHHWLN-UHFFFAOYSA-N dodecyl nitrate Chemical compound CCCCCCCCCCCCO[N+]([O-])=O PAWHIGFHUHHWLN-UHFFFAOYSA-N 0.000 claims description 2
- IDNUEBSJWINEMI-UHFFFAOYSA-N ethyl nitrate Chemical compound CCO[N+]([O-])=O IDNUEBSJWINEMI-UHFFFAOYSA-N 0.000 claims description 2
- HHXLSUKHLTZWKR-UHFFFAOYSA-N heptan-2-yl nitrate Chemical compound CCCCCC(C)O[N+]([O-])=O HHXLSUKHLTZWKR-UHFFFAOYSA-N 0.000 claims description 2
- JYMDZTRYDIQILZ-UHFFFAOYSA-N heptyl nitrate Chemical compound CCCCCCCO[N+]([O-])=O JYMDZTRYDIQILZ-UHFFFAOYSA-N 0.000 claims description 2
- AGDYNDJUZRMYRG-UHFFFAOYSA-N hexyl nitrate Chemical compound CCCCCCO[N+]([O-])=O AGDYNDJUZRMYRG-UHFFFAOYSA-N 0.000 claims description 2
- GAPFWGOSHOCNBM-UHFFFAOYSA-N isopropyl nitrate Chemical compound CC(C)O[N+]([O-])=O GAPFWGOSHOCNBM-UHFFFAOYSA-N 0.000 claims description 2
- LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical group CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 claims description 2
- CMNNRVWVNGXINV-UHFFFAOYSA-N nonyl nitrate Chemical compound CCCCCCCCCO[N+]([O-])=O CMNNRVWVNGXINV-UHFFFAOYSA-N 0.000 claims description 2
- TXQBMQNFXYOIPT-UHFFFAOYSA-N octyl nitrate Chemical compound CCCCCCCCO[N+]([O-])=O TXQBMQNFXYOIPT-UHFFFAOYSA-N 0.000 claims description 2
- PQGDRERZAVMTJA-UHFFFAOYSA-N oxolan-2-yl nitrate Chemical compound [O-][N+](=O)OC1CCCO1 PQGDRERZAVMTJA-UHFFFAOYSA-N 0.000 claims description 2
- OTRMXXQNSIVZNR-UHFFFAOYSA-N prop-2-enyl nitrate Chemical compound [O-][N+](=O)OCC=C OTRMXXQNSIVZNR-UHFFFAOYSA-N 0.000 claims description 2
- JNTOKFNBDFMTIV-UHFFFAOYSA-N propyl nitrate Chemical compound CCCO[N+]([O-])=O JNTOKFNBDFMTIV-UHFFFAOYSA-N 0.000 claims description 2
- AZAKMLHUDVIDFN-UHFFFAOYSA-N tert-butyl nitrate Chemical compound CC(C)(C)O[N+]([O-])=O AZAKMLHUDVIDFN-UHFFFAOYSA-N 0.000 claims description 2
- VTALQOYOTZKULH-UHFFFAOYSA-N undecyl nitrate Chemical compound CCCCCCCCCCCO[N+]([O-])=O VTALQOYOTZKULH-UHFFFAOYSA-N 0.000 claims description 2
- 230000002939 deleterious effect Effects 0.000 abstract description 9
- 239000000654 additive Substances 0.000 abstract description 5
- 230000015556 catabolic process Effects 0.000 abstract description 5
- 238000006731 degradation reaction Methods 0.000 abstract description 5
- 239000011800 void material Substances 0.000 abstract description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexanol Substances CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- 150000003577 thiophenes Chemical class 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 2
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 150000002830 nitrogen compounds Chemical class 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- BKCNDTDWDGQHSD-UHFFFAOYSA-N 2-(tert-butyldisulfanyl)-2-methylpropane Chemical compound CC(C)(C)SSC(C)(C)C BKCNDTDWDGQHSD-UHFFFAOYSA-N 0.000 description 1
- LNMBCRKRCIMQLW-UHFFFAOYSA-N 2-tert-butylsulfanyl-2-methylpropane Chemical compound CC(C)(C)SC(C)(C)C LNMBCRKRCIMQLW-UHFFFAOYSA-N 0.000 description 1
- QZYHIOPPLUPUJF-UHFFFAOYSA-N 3-nitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1 QZYHIOPPLUPUJF-UHFFFAOYSA-N 0.000 description 1
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- PDEDQSAFHNADLV-UHFFFAOYSA-M potassium;disodium;dinitrate;nitrite Chemical compound [Na+].[Na+].[K+].[O-]N=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PDEDQSAFHNADLV-UHFFFAOYSA-M 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 231100001234 toxic pollutant Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/23—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
- C10L1/231—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites nitro compounds; nitrates; nitrites
-
- 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
- C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
- C10L1/08—Liquid carbonaceous fuels essentially based on blends of hydrocarbons for compression ignition
-
- 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
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/12—Use of additives to fuels or fires for particular purposes for improving the cetane number
Definitions
- the present invention relates to diesel fuel compositions that are extremely stable against thermal degradation, sedimentation, and discoloration.
- the diesel fuel compositions of the present invention have been designed to be void or essentially void of certain heteroatomic compounds often present in diesel fuel and which have been discovered to cause the thermal degradation in the presence of nitrate-based cetane improver additives.
- Discoloration and sedimentation induced by nitrate-based cetane improvers can be undesirable to the consumer and can also interfere with common petroleum industry tests (e.g., ASTM D189, “Conradson Carbon Residue of Petroleum Products” and ASTM D524, “Ramsbottom Carbon Residue of Petroleum Products”). It is therefore desired to have a diesel fuel composition which can demonstrate excellent thermal stability, i.e., lack of sedimentation and minimal discoloration upon heating to >120° C. It has been discovered that certain components in the diesel fuel are responsible for these undesired effects, and that by eliminating these certain components, an improved diesel fuel is produced.
- a feature of the present invention is to provide a diesel fuel composition exhibiting improved ignition quality, which can demonstrate excellent thermal stability, i.e., lack of sedimentation and minimal discoloration when heated.
- Another feature of the present invention is to provide a diesel fuel composition containing a major amount of a hydrocarbon boiling in the middle distillate boiling range, and a minor amount of a nitrate-containing cetane improver, wherein the composition is free of, or essentially free of, certain heteroatomic compounds.
- a further feature of the present invention is to provide a method of reducing the sedimentation and/or discoloration of a middle distillate fuel containing nitrate-based cetane improver.
- the present invention relates to a diesel fuel composition containing a major amount of a hydrocarbon fuel boiling in the middle distillate boiling range, and a minor amount of a nitrate-containing cetane improver, wherein the composition is free of, or essentially free of, one or more heteroatomic compounds selected from pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids, and/or indolines.
- heteroatomic compound herein is meant one or more heteroatomic compounds selected from pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids, and/or indolines.
- heteroatomic compound herein is meant a heteroatomic compound that in a diesel fuel containing nitrated cetane improver causes discoloration and/or sedimentation of the diesel fuel upon heating of the fuel.
- free of in the present invention is meant a deleterious heteroatomic compound level generally undetectable in terms of adverse effect on color and sediment formation of the diesel fuel. This level is generally a level of less than about 2 ppm of deleterious heteroatomic compound in the finished diesel fuel. Similarly, by “removing all of” herein is meant a remaining level, if any, of deleterious heteratomic compound of less than about 2 ppm.
- essentially free of in the present invention is meant a level of less than about 5 ppm of heteroatomic compound in the finished diesel fuel. Similarly, by “removing essentially all of” herein is meant a remaining level, if any, of heteratomic compound of less than about 5 ppm.
- nitrate-containing cetane improver herein is meant chemical compounds that contain a nitrate group covalently bonded, ionically bonded, or generated in situ.
- nitrate-containing cetane improvers useful in the present invention include methyl nitrate, ethyl nitrate, propyl nitrate, isopropyl nitrate, allyl nitrate, butyl nitrate, isobutyl nitrate, sec-butyl nitrate, tert-butyl nitrate, amyl nitrate, isoamyl nitrate, 2-amyl nitrate, 3-amyl nitrate, n-pentyl nitrate, hexyl nitrate, heptyl nitrate, 2-heptyl nitrate, octyl nitrate, isooctyl nitrate, 2-
- an improved diesel fuel is prepared by combining a major amount of a middle distillate fuel, and a minor amount of a nitrate-based cetane improver, and removing before or after the addition of the nitrate-based cetane improver all or essentially all of one or more the following heteroatomic compounds: pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids, and/or indolines.
- middle distillate diesel fuel containing nitrate-based cetane improver has significantly improved thermal stability, i.e., reduced discoloration and reduced sedimentation, if the deleterious heteroatomic compounds of pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids, and/or indolines are removed or essentially removed from the fuel, relative to the comparable diesel fuel from which these heteroatomic compounds have not been removed.
- the aforementioned deleterious heteroatomic species may be removed by any method known to those skilled in the art, including hydrotreatment, selective adsorption, or oxidation
- the nitrate-based cetane improver can be present in the diesel fuel compositions of the present invention at a level of from about 100 ppm to about 10,000 ppm.
- heteroatomic compounds do not have an adverse or deleterious effect on sedimentation and discoloration of middle distillate fuel containing nitrate-based cetane improver.
- the heteroatomic compounds that do not have an adverse or deleterious effect on these properties of diesel fuel include anilines, pyridines, quinolines, amides, thiophenes, sulfoxides, phenols, carboxylic acids, nitriles, nitro compounds, aldehydes, esters, alcohols, peroxides, and carbazoles (see Table 1).
- a benefit of this particular invention over the prior art is that certain species that are hard to remove from the diesel fuel by desulfurization and/or denitrogenation can be left in the fuel because they have been discovered herein to be innocuous in terms of thermal stability of the resulting diesel fuel. For example, most nitrogen compounds and thiophenes are more difficult to remove by hydrogenation than sulfides, mercaptans, etc. However, since most nitrogen compounds and thiophenes do not cause thermal instability of the diesel fuel, they can be left in the fuel at substantial savings to the refiner.
- a low sulfur D-2 (ASTM D975) diesel fuel having the following properties:
- Cetane number ASTM D613 35-60, and preferably 40-55
- Pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids, and indolines ⁇ 5 ppm total heteroatomic content.
- the amount of each of pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids, and indolines is no more than 5 ppm, and in a more preferred embodiment, no more than 2 ppm.
- the present invention provides in another embodiment a diesel fuel meeting the requirements of ASTM D 975 for a low sulfur No. 2-D diesel and providing emission benefits at least equivalent to a diesel fuel as per Section 2282(g), Title 13, California Code of Regulations, said fuel containing from about 10 vol. % to about 30 vol.
- % aromatics and having (1) a Cetane number of at least 40 but less than 60, and preferably from 45 to 55; (2) a nitrogen content of no greater than 1000 ppmw; (3) a sulfur content of no greater than 50 ppmw; and (4) a total amount of nitrogen and sulfur from pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids and/or indolines of no more than 5 ppm, preferably no more than 2 ppm.
- the amount of each of pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids, and indolines is no more than 5 ppm, and in a more preferred embodiment, no more than 2 ppm.
- An ultralow-sulfur diesel fuel (Fuel 9041), with inspection data as listed in Table 2, was separately treated with enough of each of the additives listed in Table 1 to deliver 350 ppm of oxygen, nitrogen, or sulfur.
- Fuel 9041 contained very low amounts of sulfur and nitrogen, but was in all other properties typical for a No. 2 diesel fuel.
- the base fuel with no added heteroatomic compound was very stable in the presence of 2-EH nitrate, ensuring that any instability observed in subsequent experiments arose from the introduced heteroatomic species.
- the heteroatomic compounds were selected as representative of compounds that might typically be expected to be found in a diesel fuel.
- Half of each fuel composition was treated with 2500 ppmv of 2-EH nitrate.
- nitrate-free and nitrate-containing fuel compositions were subjected to 180-minute thermal stability testing at 150° C. as described in pad stability test ASTM D6468.
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Abstract
Description
- The present invention relates to diesel fuel compositions that are extremely stable against thermal degradation, sedimentation, and discoloration. The diesel fuel compositions of the present invention have been designed to be void or essentially void of certain heteroatomic compounds often present in diesel fuel and which have been discovered to cause the thermal degradation in the presence of nitrate-based cetane improver additives.
- The benefits of operating a diesel engine on a diesel fuel treated with a nitrate-based cetane improver are well known: improved cold starting, less combustion noise, smoother engine operation and reduced toxic pollutant emissions. It is known that diesel fuels containing nitrate-containing cetane improvers often exhibit instability in the form of discoloration and sedimentation when heated to high temperatures (>120° C.). It is also known that organic nitrate cetane improvers (e.g. 2-ethylhexyl nitrate, commercially available from Ethyl Corporation as HiTEC® 4103 cetane improver, also known as DII-3) can worsen diesel fuel discoloration and sedimentation in the 150° C. pad stability test (ASTM D6468). The reasons for this phenomenon, however, have never been satisfactorily explained and several studies carried out over the years have failed to establish a correlation between any of a fuel's physical and chemical characteristics and its thermal stability. It has been widely observed that severely hydrotreated fuels are, in general, less susceptible to thermal degradation than conventionally refined fuels. Severe hydrotreatment reduces the amounts of heteroatomic species (i.e., compounds containing oxygen, nitrogen and/or sulfur atoms) in diesel fuel. Additionally, many published studies have implicated heteroatomic compounds in diesel fuel sedimentation at relatively low temperatures (below about 100° C.). These results imply that heteroatomic compounds may be responsible for high-temperature instability. None of these studies, however, addresses the issue of high-temperature diesel fuel instability in the presence of additives such as cetane improvers.
- Several diesel fuels containing low amounts of total sulfur and/or nitrogen have been described. U.S. Pat. No. 6,150,575 shows low sulfur diesel fuels; U.S. Pat. No. 5,807,413 shows very low sulfur content and nitrogen content diesel fuels; U.S. Pat. No. 5,792,339 shows low sulfur content and higher nitrogen content diesel fuels; U.S. Pat. Nos. 5,389,111 and 5,389,112 show low sulfur content diesel fuels; EP 457589 shows a low sulfur content diesel fuel; and WO 00/12654 shows a very low sulfur content and nitrogen content diesel fuel. In all of these cases, the amounts of sulfur and nitrogen are considered only as bulk properties of the fuel; differences between chemical types of heteroatomic compounds are not taken into account. We have discovered that different types of heteroatomic molecules have different effects on a fuel's high-temperature stability in the presence of nitrate-based cetane improvers.
- In the patents and patent applications involving ultralow-sulfur content diesel fuels (i.e., fuels with less than about 50 ppmw sulfur), the presence of nitrogen-containing additives such as nitrate-based cetane improvers is severely limited by the allowable or preferred total nitrogen content of the disclosed fuel compositions. Some of these patents and patent applications also require fuel compositions of limited aromatic content; however, low aromatic content is not required for this invention.
- The patents, patent applications, and other documents recited herein are fully incorporated by reference.
- Discoloration and sedimentation induced by nitrate-based cetane improvers can be undesirable to the consumer and can also interfere with common petroleum industry tests (e.g., ASTM D189, “Conradson Carbon Residue of Petroleum Products” and ASTM D524, “Ramsbottom Carbon Residue of Petroleum Products”). It is therefore desired to have a diesel fuel composition which can demonstrate excellent thermal stability, i.e., lack of sedimentation and minimal discoloration upon heating to >120° C. It has been discovered that certain components in the diesel fuel are responsible for these undesired effects, and that by eliminating these certain components, an improved diesel fuel is produced.
- A feature of the present invention is to provide a diesel fuel composition exhibiting improved ignition quality, which can demonstrate excellent thermal stability, i.e., lack of sedimentation and minimal discoloration when heated.
- It has been discovered that certain heteroatomic compounds when present in diesel fuel containing nitrate-containing cetane improver cause severe discoloration and/or sedimentation when the fuel is heated.
- It has also been discovered that the absence or removal of these certain heteroatomic compounds from diesel fuel containing, or to later contain, nitrate-containing cetane improver, significantly improves the fuel's thermal stability and minimizes discoloration and/or sedimentation.
- Another feature of the present invention is to provide a diesel fuel composition containing a major amount of a hydrocarbon boiling in the middle distillate boiling range, and a minor amount of a nitrate-containing cetane improver, wherein the composition is free of, or essentially free of, certain heteroatomic compounds.
- A further feature of the present invention is to provide a method of reducing the sedimentation and/or discoloration of a middle distillate fuel containing nitrate-based cetane improver.
- Accordingly, the present invention relates to a diesel fuel composition containing a major amount of a hydrocarbon fuel boiling in the middle distillate boiling range, and a minor amount of a nitrate-containing cetane improver, wherein the composition is free of, or essentially free of, one or more heteroatomic compounds selected from pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids, and/or indolines.
- By “heteratomic compound” herein is meant one or more heteroatomic compounds selected from pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids, and/or indolines.
- By “deleterious” heteroatomic compound herein is meant a heteroatomic compound that in a diesel fuel containing nitrated cetane improver causes discoloration and/or sedimentation of the diesel fuel upon heating of the fuel.
- By “free of” in the present invention is meant a deleterious heteroatomic compound level generally undetectable in terms of adverse effect on color and sediment formation of the diesel fuel. This level is generally a level of less than about 2 ppm of deleterious heteroatomic compound in the finished diesel fuel. Similarly, by “removing all of” herein is meant a remaining level, if any, of deleterious heteratomic compound of less than about 2 ppm.
- By “essentially free of” in the present invention is meant a level of less than about 5 ppm of heteroatomic compound in the finished diesel fuel. Similarly, by “removing essentially all of” herein is meant a remaining level, if any, of heteratomic compound of less than about 5 ppm.
- By “nitrate-containing cetane improver” herein is meant chemical compounds that contain a nitrate group covalently bonded, ionically bonded, or generated in situ. Examples of nitrate-containing cetane improvers useful in the present invention include methyl nitrate, ethyl nitrate, propyl nitrate, isopropyl nitrate, allyl nitrate, butyl nitrate, isobutyl nitrate, sec-butyl nitrate, tert-butyl nitrate, amyl nitrate, isoamyl nitrate, 2-amyl nitrate, 3-amyl nitrate, n-pentyl nitrate, hexyl nitrate, heptyl nitrate, 2-heptyl nitrate, octyl nitrate, isooctyl nitrate, 2-ethylhexyl nitrate, nonyl nitrate, decyl nitrate, undecyl nitrate, dodecyl nitrate, cyclopentyl nitrate, cyclohexyl nitrate, methylcyclohexyl nitrate, cyclododecyl nitrate, 2-ethoxyethyl nitrate, 2-(2-ethoxyethoxy)ethyl nitrate, tetrahydrofuranyl nitrate, tetraethyleneglycol dinitrate, isomers thereof, and mixtures thereof A preferred nitrate-containing cetane improver in an embodiment of the present invention is 2-ethyl hexyl nitrate (“2-EH nitrate”).
- It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are intended to provide further explanation of the present invention, as claimed.
- According to an embodiment of the present invention, an improved diesel fuel is prepared by combining a major amount of a middle distillate fuel, and a minor amount of a nitrate-based cetane improver, and removing before or after the addition of the nitrate-based cetane improver all or essentially all of one or more the following heteroatomic compounds: pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids, and/or indolines.
- It has been discovered that middle distillate diesel fuel containing nitrate-based cetane improver has significantly improved thermal stability, i.e., reduced discoloration and reduced sedimentation, if the deleterious heteroatomic compounds of pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids, and/or indolines are removed or essentially removed from the fuel, relative to the comparable diesel fuel from which these heteroatomic compounds have not been removed. The aforementioned deleterious heteroatomic species may be removed by any method known to those skilled in the art, including hydrotreatment, selective adsorption, or oxidation
- The nitrate-based cetane improver can be present in the diesel fuel compositions of the present invention at a level of from about 100 ppm to about 10,000 ppm.
- It has also been discovered that certain heteroatomic compounds do not have an adverse or deleterious effect on sedimentation and discoloration of middle distillate fuel containing nitrate-based cetane improver. The heteroatomic compounds that do not have an adverse or deleterious effect on these properties of diesel fuel include anilines, pyridines, quinolines, amides, thiophenes, sulfoxides, phenols, carboxylic acids, nitriles, nitro compounds, aldehydes, esters, alcohols, peroxides, and carbazoles (see Table 1).
- A benefit of this particular invention over the prior art is that certain species that are hard to remove from the diesel fuel by desulfurization and/or denitrogenation can be left in the fuel because they have been discovered herein to be innocuous in terms of thermal stability of the resulting diesel fuel. For example, most nitrogen compounds and thiophenes are more difficult to remove by hydrogenation than sulfides, mercaptans, etc. However, since most nitrogen compounds and thiophenes do not cause thermal instability of the diesel fuel, they can be left in the fuel at substantial savings to the refiner.
TABLE 1 Summary of tendencies of heteroatomic compounds to cause thermal instability of diesel fuel containing 2-EH nitrate Compounds that cause thermal Compounds that do not cause thermal instability (degree of effect) instability Pyrroles (severe) Anilines Indoles (moderate to severe) Pyridines Indolines (moderate) Quinolines Sulfides (severe) Amides Disulfides (severe) Carbazoles Mercaptans (severe) Thiophenes Thioacids (severe) Sulfoxides Sulfonic acids (very severe) Phenols Carboxylic acids Nitriles Nitro compounds Aldehydes Alcohols Esters Peroxides - Thus, in another embodiment of the present invention is provided a low sulfur D-2 (ASTM D975) diesel fuel having the following properties:
- Cetane number, ASTM D613 35-60, and preferably 40-55
- Cetane index, ASTM D4737 <60
- Aromatics, total, wt. % ASTM D5186 <40
- Polynuclear aromatics, wt. %, ASTM D2425 <11
- Sulfur, ppmw, ASTM D2622-1 <50
- Nitrogen, ppmw ASTM D4629 <1000 (from all sources)
- Pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids, and indolines <5 ppm total heteroatomic content. In a preferred e mbodiment, the amount of each of pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids, and indolines is no more than 5 ppm, and in a more preferred embodiment, no more than 2 ppm.
- In addition, the present invention provides in another embodiment a diesel fuel meeting the requirements of ASTM D 975 for a low sulfur No. 2-D diesel and providing emission benefits at least equivalent to a diesel fuel as per Section 2282(g), Title 13, California Code of Regulations, said fuel containing from about 10 vol. % to about 30 vol. % aromatics and having (1) a Cetane number of at least 40 but less than 60, and preferably from 45 to 55; (2) a nitrogen content of no greater than 1000 ppmw; (3) a sulfur content of no greater than 50 ppmw; and (4) a total amount of nitrogen and sulfur from pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids and/or indolines of no more than 5 ppm, preferably no more than 2 ppm. In a preferred embodiment, the amount of each of pyrroles, indoles, sulfides, disulfides, mercaptans, thioacids, sulfonic acids, and indolines is no more than 5 ppm, and in a more preferred embodiment, no more than 2 ppm.
- The following examples further illustrate aspects of the present invention but do not limit the present invention.
- An ultralow-sulfur diesel fuel (Fuel 9041), with inspection data as listed in Table 2, was separately treated with enough of each of the additives listed in Table 1 to deliver 350 ppm of oxygen, nitrogen, or sulfur. Fuel 9041 contained very low amounts of sulfur and nitrogen, but was in all other properties typical for a No. 2 diesel fuel. The base fuel with no added heteroatomic compound was very stable in the presence of 2-EH nitrate, ensuring that any instability observed in subsequent experiments arose from the introduced heteroatomic species. The heteroatomic compounds were selected as representative of compounds that might typically be expected to be found in a diesel fuel. Half of each fuel composition was treated with 2500 ppmv of 2-EH nitrate. The nitrate-free and nitrate-containing fuel compositions were subjected to 180-minute thermal stability testing at 150° C. as described in pad stability test ASTM D6468.
TABLE 2 Inspection data for Fuel 9041 Aromatics, vol. % 33.6 Olefins, vol. % 2.1 Saturates, vol. % 64.3 Specific gravity 0.850 T10, ° C. 222 T50, ° C. 271 T90, ° C. 323 Sulfur, ppmw 7 Nitrogen, ppmw 27 Cetane number 44.2 Kinematic viscosity, cSt, 40° C. 2.87 - In the thermal pad stability test ASTM D6468, the reflectance of light on a filter pad is measured and higher pad reflectances are desired as indicia that less sedimentation has occurred in the fuel.
- Results from Thermal Stability Pad Test (ASTM D6468)
w/o DII-3 w/ DII-3 Oxygen-containing compound None 98.7 97.3 Phenylacetaldehyde 99.6 99.7 Dimethylmalonate 99.5 99.6 p-Cresol 98.6 98.2 Lauric acid 98.6 96.1 2-Ethylhexanol 94.9 97.1 di-t-butyl peroxide 94.9 95.8 Benzoic acid 94.0 95.0 Sulfur-containing compound None 98.7 97.3 Thianaphthene 97.5 97.2 Dimethyl sulfoxide 96.5 97.2 Di-t-butyl sulfide 48.7 3.7 4-methylbenzenethiol 24.8 12.0 1-octanethiol 12.6 3.3 Di-t-butyl disulfide 7.4 2.5 Thiobenzoic acid 7.3 1.8 p-Toluenesulfonic acid 3.8 1.0 Nitrogen-containing compound None 98.7 97.3 N,N-dimethylaniline 98.6 96.0 3,5-lutidine 98.5 97.1 2,5-dimethylaniline 98.1 98.3 3-nitrotoluene 98.0 94.4 Quinaldine 97.4 97.5 2,4,6-collidine 97.1 96.9 Benzonitrile 94.9 97.9 2-pyrrolidinone 91.6 97.7 Indole 84.8 91.5 2-methylindole 79.6 48.6 Indoline 62.3 65.7 2,5-dimethylpyrrole 7.0 3.1 - A number of conclusions can be drawn from these results. First, oxygen-containing compounds, even moderately strong carboxylic acids, have no adverse effect on the diesel fuel containing 2-EH nitrate cetane improver when the fuel was subjected to thermal stressing. With the exception of pyrroles and indoles, the same is true for the nitrogenous compounds investigated. In contrast, most of the sulfur-containing species studied had a strongly detrimental effect on the thermal stability of diesel fuel containing 2-EH nitrate.
- Other embodiments of the present invention will be apparent to those skilled in the art from consideration of the specification and practice of the invention disclosed herein. It is intended that the specification and examples be considered as exemplary only, with a true scope and spirit of the invention being indicated by the following claims. This invention is susceptible to considerable variation in its practice. Accordingly, this invention is not limited to the specific exemplifications set forth hereinabove. Rather, this invention is within the spirit and scope of the appended claims, including the equivalents thereof available as a matter of law.
- The patentee does not intend to dedicate any disclosed embodiments to the public, and to the extent any disclosed modifications or alterations may not literally fall within the scope of the claims, they are considered to be part of the invention under the doctrine of equivalents.
Claims (26)
Priority Applications (4)
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US10/020,411 US20030110684A1 (en) | 2001-12-18 | 2001-12-18 | Extremely stable diesel fuel compositions |
CA002411933A CA2411933C (en) | 2001-12-18 | 2002-11-15 | Extremely stable diesel fuel compositions |
JP2002360503A JP3764721B2 (en) | 2001-12-18 | 2002-12-12 | Extremely stable diesel fuel composition |
EP02258749A EP1321504A3 (en) | 2001-12-18 | 2002-12-18 | Extremely stable diesel fuel compositions |
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US10/020,411 US20030110684A1 (en) | 2001-12-18 | 2001-12-18 | Extremely stable diesel fuel compositions |
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US20070220803A1 (en) * | 2006-03-24 | 2007-09-27 | Henry Cyrus P Jr | Enhanced antistatic additives for hydrocarbon fuels & solvents |
US20080067110A1 (en) * | 2002-04-26 | 2008-03-20 | Bp Oil International Limited | Method and apparatus for improving the oxidative thermal stability of distillate fuel |
WO2009141166A1 (en) | 2008-05-19 | 2009-11-26 | Furanix Technologies B.V. | Fuel composition |
EP2128227A1 (en) | 2008-05-19 | 2009-12-02 | Furanix Technologies B.V | Monosubstituted furan derivatives via decarboxylation and use thereof as (aviation) fuel |
US20090320354A1 (en) * | 2007-01-29 | 2009-12-31 | Basf Se | Branched decyl nitrates and their use as combustion improvers and/or cetane number improvers in fuels |
WO2019089225A1 (en) | 2017-11-02 | 2019-05-09 | Exxonmobil Research And Engineering Company | Cetane improver in fuel oil |
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WO2021225734A1 (en) * | 2020-05-08 | 2021-11-11 | Exxonmobil Research And Engineering Company | Motor gasoline with improved octane and method of use |
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JP2003193069A (en) | 2003-07-09 |
EP1321504A2 (en) | 2003-06-25 |
EP1321504A3 (en) | 2003-10-22 |
CA2411933C (en) | 2009-03-24 |
CA2411933A1 (en) | 2003-06-18 |
JP3764721B2 (en) | 2006-04-12 |
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