TWI444467B - 用於液體碳氫化合物及其他燃料與油之標記物化合物 - Google Patents
用於液體碳氫化合物及其他燃料與油之標記物化合物 Download PDFInfo
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- TWI444467B TWI444467B TW100115554A TW100115554A TWI444467B TW I444467 B TWI444467 B TW I444467B TW 100115554 A TW100115554 A TW 100115554A TW 100115554 A TW100115554 A TW 100115554A TW I444467 B TWI444467 B TW I444467B
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- 150000001875 compounds Chemical class 0.000 title claims description 35
- 239000000446 fuel Substances 0.000 title claims description 34
- 229930195733 hydrocarbon Natural products 0.000 title claims description 18
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 18
- 239000003550 marker Substances 0.000 title description 20
- 239000003921 oil Substances 0.000 title description 6
- 239000007788 liquid Substances 0.000 title description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- 239000003225 biodiesel Substances 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- 239000003208 petroleum Substances 0.000 claims description 13
- 239000003209 petroleum derivative Substances 0.000 claims description 11
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- WGCDPEPDHWCDPT-UHFFFAOYSA-N 2-[[4-[4-[(2,5-dimethylphenyl)methyl]phenyl]phenyl]methyl]-1,4-dimethylbenzene Chemical group CC1=CC=C(C)C(CC=2C=CC(=CC=2)C=2C=CC(CC=3C(=CC=C(C)C=3)C)=CC=2)=C1 WGCDPEPDHWCDPT-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- 239000002283 diesel fuel Substances 0.000 description 4
- 239000003502 gasoline Substances 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- INZDTEICWPZYJM-UHFFFAOYSA-N 1-(chloromethyl)-4-[4-(chloromethyl)phenyl]benzene Chemical group C1=CC(CCl)=CC=C1C1=CC=C(CCl)C=C1 INZDTEICWPZYJM-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000000295 fuel oil Substances 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000004847 absorption spectroscopy Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- KZPIOEYBLTUCFP-UHFFFAOYSA-N 1-methyl-4-[[4-[4-[(4-methylphenyl)methyl]phenyl]phenyl]methyl]benzene Chemical group C1=CC(C)=CC=C1CC1=CC=C(C=2C=CC(CC=3C=CC(C)=CC=3)=CC=2)C=C1 KZPIOEYBLTUCFP-UHFFFAOYSA-N 0.000 description 1
- VFYFMNCKPJDAPV-UHFFFAOYSA-N 2,2'-(5-oxo-1,3-dioxolan-4,4-diyl)diessigs Chemical compound C1N(C2)CN3CN1CN2C3.OC(=O)CC1(CC(O)=O)OCOC1=O VFYFMNCKPJDAPV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 238000001042 affinity chromatography Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 238000002270 exclusion chromatography Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C10L1/00—Liquid carbonaceous fuels
- C10L1/003—Marking, e.g. coloration by addition of pigments
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/12—Polycyclic non-condensed hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/164—Unsaturated ethers containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
-
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
- C10L1/023—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for spark ignition
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
- C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/16—Hydrocarbons
- C10L1/1608—Well defined compounds, e.g. hexane, benzene
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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
- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M127/00—Lubricating compositions characterised by the additive being a non- macromolecular hydrocarbon
- C10M127/04—Lubricating compositions characterised by the additive being a non- macromolecular hydrocarbon well-defined aromatic
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- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
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- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/007—Coloured or dyes-containing lubricant compositions
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/26—Oils; Viscous liquids; Paints; Inks
- G01N33/28—Oils, i.e. hydrocarbon liquids
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
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Description
本發明係關於有用於作為用於液體碳氫化合物及其他燃料與油之化學標記物之化合物。
以各種化學標記物對石油碳氫化合物及其他燃料與油進行標記係於本領域中周知。各種化合物以及大量用於偵檢該等標記物之技術已用於此目的,該等技術係例如:吸收光譜學及質譜學。例如:美國申請案公開第2007/0184555號揭露使用各種用於標記液態碳氫化合物及其他燃料與油之有機化合物。然而,對於用於此等產物之額外的標記物化合物一直有所需求。標記物的組合可用作數位標記系統而以該等標記物之用量比例構成經標記產物之代碼。額外可用作燃料及潤滑劑標記物之化合物係所欲者以增加可用代碼至最大值。本發明欲解決之問題為尋找可用於標記液體碳氫化合物及其他燃料與油之額外標記物。
本發明提供一種具有式(I)之化合物:
其中,G表示至少一個選自由C1
-C12
烷基和C1
-C12
烷氧基所組成群組之取代基。
本發明進一步提供一種用於標記石油碳氫化合物、生質柴油燃料或乙醇燃料之方法,該方法係包含將至少一種具有式(I)之化合物加入該石油碳氫化合物、生質柴油燃料或乙醇燃料中。
除非另外說明,否則百分比為重量百分比(wt%)且溫度為℃。濃度係以重量/重量為基準或以重量/容量(毫克(mg)/公升(L))為基準所計算之每百萬分之分數(ppm)來表示;較佳以重量/容量為基準。術語“石油碳氫化合物”係指具有碳氫化合物組成為主之產物,然而其可含有少量氧、氮、硫或磷;石油碳氫化合物包含原油類以及從石油精煉過程衍生之產物;其包括,舉例而言,原油、潤滑油、液壓油、煞車油、汽油、柴油燃料、煤油、噴射機燃料及燃料油。可將本發明之標記物化合物加入石油碳氫化合物、生質柴油燃料、乙醇燃料,或其混合物中。生質柴油燃料為從生物衍生之含有脂肪酸烷酯(特別係甲酯)之混合物之燃料。生質柴油燃料係典型地藉由將原生(virgin)或回收(recycled)植物油進行轉酯反應而產生,雖然亦可使用動物脂肪。乙醇燃料為任何含有純形式之乙醇或與石油碳氫化合物混合之乙醇(如“酒精汽油(gasohol)”)之燃料。“烷基”為具有一個至二十二個以直鏈或分支鏈排列之碳原子之經取代或未經取代之烴基(hydrocarbyl)。較佳地,本發明之化合物係含有以其天然之同位素比例存在的元素。
G表示至少一個選自由C1
-C12
烷基和C1
-C12
烷氧基所組成群組之取代基,亦即,式(I)中載有“G”取代基之各芳香環具有至少一個選自由C1
-C12
烷基和C1
-C12
烷氧基所組成群組之取代基。較佳地,G表示在各芳香環上之一個至三個可為相同或不同的取代基,較佳為兩或三個取代基,較佳為兩個或三個相同的取代基。然而,“G”所表示之取代基在這兩個經G取代之芳香環上係相同,亦即,該化合物以在中央聯苯部分(moiety)之苯環之間的對稱平面呈對稱。較佳地,G表示至少一個選自由C1
-C6
烷基和C1
-C6
烷氧基(較佳為C1
-C4
烷基和C1
-C4
烷氧基,較佳為C1
-C4
烷基,較佳為C1
-C3
烷基,較佳為甲基和乙基)所組成群組之取代基。
較佳地,於本發明之方法中,每種標記物之最小量為至少0.01 ppm,較佳為至少0.05 ppm,較佳為至少0.1 ppm,較佳為至少0.2 ppm。較佳地,每種標記物之最大量為50 ppm,較佳為20 ppm,較佳為15 ppm,較佳為10 ppm,較佳為5 ppm,較佳為2 ppm,較佳為1 ppm,較佳為0.5 ppm。較佳地,標記物化合物無法經由視覺手段於經標記之石油碳氫化合物、生質柴油燃料或乙醇燃料中偵檢,亦即不可能經由未受幫助之顏色或其他特徵之肉眼觀察,而決定該石油碳氫化合物、生質柴油燃料或乙醇燃料含有標記物化合物。較佳地,標記物化合物為一種通常不作為石油碳氫化合物、生質柴油燃料或乙醇燃料本身之成分,或不作為用於該石油碳氫化合物、生質柴油燃料或乙醇燃料之添加劑存在於其所添加之石油碳氫化合物、生質柴油燃料或乙醇燃料中之標記物化合物。
較佳地,該標記物化合物係具有至少3之log P值,其中P為1-辛醇/水分配係數(partition coefficient)。較佳地,該標記物化合物具有至少4、較佳為至少5之log P值。未曾以實驗方式測定且未於文獻中發表之log P值可使用Meylan,W.M. & Howard,P. H.,J. Pharm Sci.
,vol. 84,pp.83-92(1995)中揭露之方法進行估計。較佳地,該石油碳氫化合物、生質柴油燃料或乙醇燃料為石油碳氫化合物或生質柴油燃料;較佳為石油碳氫化合物;較佳為原油、汽油、柴油燃料、煤油、噴射機燃料或燃料油;較佳為汽油。
於本發明一個具體例中,此等標記物化合物係經由使用層析技術(例如:氣相層析法、液相層析法、薄層層析法、紙層析法、吸附層析法、親和層析法、毛細管電泳、離子交換及分子排除層析法)將其從石油碳氫化合物、生質柴油燃料或乙醇燃料之成分至少部分分離而予以偵檢。層析法後接著進行下列至少一者:(i)質譜分析,及(ii)傅立葉轉換紅外光譜分析(FTIR)。較佳係經由質譜分析測定標記物化合物之身份(identity)。較佳地,質譜分析係用以偵檢石油碳氫化合物、生質柴油燃料或乙醇燃料中之標記物化合物,而無須進行任何分離。或者,標記物化合物可於分析前濃縮,例如:經由蒸餾除去石油碳氫化合物或乙醇之某些較具揮發性之成分。
較佳地,存在超過一種標記物化合物。多重標記物化合物之使用促進將可用於識別石油碳氫化合物、生質柴油燃料或乙醇燃料之來源與其他特徵之經編碼資訊併入石油碳氫化合物、生質柴油燃料或乙醇燃料中。此代碼包含標記物化合物之身份性與相對量,例如:固定整數比。一種、二種、三種或更多種標記物化合物可用於形成該代碼。依據本發明之標記物化合物可與其他類型之標記物組合,其他類型之標記物例如,可由吸收光譜法偵檢之標記物,包括美國專利案第6,811,575號;美國專利申請案公開第2004/0250469號及歐洲申請案公開第1,479,749號中揭露之標記物。標記物化合物係直接置於石油碳氫化合物、生質柴油燃料或乙醇燃料中,或置於含有其他化合物之添加劑包裝(例如,潤滑劑之抗磨損添加劑、汽油之清潔劑等等)中,再將該添加劑包裝添加於石油碳氫化合物、生質柴油燃料或乙醇燃料中。
本發明之化合物可藉由本領域中已知的方法製備。例如,可根據下述反應式以4,4’-雙氯甲基-1,1’-聯苯烷化經取代之苯:
用於將經取代之苯烷化之典型路易士酸適合用於此製程。較佳地,經取代之苯僅在1,4-或1,3,5-位置具有取代基,造成烷化反應之產物中僅有單一種可能的位置異構物。例如,若經取代之苯為1,4-二甲基苯,則該產物具有下述結構,其中該產物之甲基在2和5位置。
將4,4’-雙(氯甲基)-1,1’-聯苯(1.0g)和對二甲苯(25mL)加入00mL燒瓶中。將四氯化鈦(6滴)加入於室溫攪拌之該清澈溶液中,而混合物迅速變深褐色。於室溫攪拌隔夜後,添加乙醇(2mL)以壓制(kill)觸媒,而混合物變成淡黃色(light,cream colored)懸浮液。將混合物轉移至分液漏斗,並且以稀釋之HCl水溶液及隨後之飽和碳酸氫鈉水溶液清洗。以硫酸鎂乾燥有機層,且在旋轉蒸發器上於真空下濃縮成乾燥。使淺棕色(tan)固體自甲苯再結晶,產生白色結晶產物,mp=144.6℃。GC/MS、HNMR、CNMR以及IR均與期望的產物一致。
將4,4’-雙(氯甲基)-1,1’-聯苯(25.1g)和甲苯(300mL)加入500mL燒瓶中。將四氯化鈦(1mL)加入於室溫攪拌之該清澈溶液中,而混合物迅速變深褐色。在5分鐘後,加入第二份1mL等分分裝之觸酶。於室溫攪拌隔夜後,添加乙醇(10 mL)以壓制(kill)觸媒,而混合物變成淡黃色懸浮液。將有機層在旋轉蒸發器上於真空下濃縮成乾燥。將淺棕色固體懸浮於200mL沸騰之甲苯中,並且以MgSO4
處理。經由真空過濾通過玻璃纖維過濾纸,而給出澄清溶液,稍候趁熱將200mL之庚烷加入其中。使稍微混濁之溶液冷卻至室溫,隨後放置於冷凍室隔夜以完成結晶反應。回收白色結晶,17.4g,mp=161.8℃。GC/MS、HNMR、CNMR以及IR均與期望的產物一致。
以0.1ppm之濃度,將4,4’-雙(2,5-二甲基苯甲基)-1,1’-聯苯加入自地方Marathon加油站購買之商用柴油燃料中。藉由使用Agilent DB-35ms柱(15公尺×0.25mm ID×0.25μm)之GC/MS分析經標記之燃料。使用下述溫度程式(program)分析該等樣本:起始於100℃,以20℃/分鐘之升溫速度升至280℃,於280℃保持10分鐘,之後以20℃/分鐘之升溫速度升至340℃,於340℃保持6分鐘,隨後以20℃/分鐘之升溫速度最終升至360℃,於360℃保持1分鐘。使用SIM:390輕易地偵檢出4,4’-雙(2,5-二甲基苯甲基)-1,1’-聯苯。重複分析(n=6)證實有少於5%之相對標準差(RSD)。
使用含有100至1000ppm之標記物以及等量之鯊烯內參考標準品的二甲苯溶液以下述方法(protocol)施行標記物的安定性及可萃取性:
洗滌:
將95份經標記之二甲苯與5份洗滌劑於100mL小瓶中混合。使用磁力攪拌棒溫和混合8小時。停止攪拌,取二甲苯溶液之等分分裝物。藉由GC分析,並比較標記物相對於參考(未洗滌)樣本之反應。
洗滌劑:
1)5%硫酸
2)98%硫酸
3)5% NaOH溶液
4)50% NaOH溶液
5)活性木炭(使用98份二甲苯溶液對2份木炭)
6)5%漂白劑
為了測試金屬吸附性,將100mL經標記之二甲苯溶液於室溫以5公克金屬刨花(shaving)處理8小時。再度使用GC分析,以測定任何流失至金屬表面之標記物。
Claims (10)
- 一種具有式(I)之化合物:
- 如申請專利範圍第1項所述之化合物,其中,G表示至少一個選自由C1 -C6 烷基所組成群組之取代基。
- 如申請專利範圍第2項所述之化合物,其中,G表示兩個或三個選自由C1 -C6 烷基所組成群組之取代基。
- 如申請專利範圍第3項所述之化合物,其中,G表示兩個或三個選自由C1 -C4 烷基所組成群組之取代基。
- 如申請專利範圍第4項所述之化合物,其中,G表示兩個或三個甲基或兩個或三個乙基。
- 一種用於標記石油碳氫化合物、生質柴油燃料或乙醇燃料之方法,該方法包括對該石油碳氫化合物、生質柴油燃料或乙醇燃料加入至少一種具有式(I)之化合物:
- 如申請專利範圍第6項所述之方法,其中,每種式(I)之化合物係以0.05ppm至20ppm之濃度存在。
- 如申請專利範圍第7項所述之方法,其中,G表示兩個或三個選自由C1 -C6 烷基所組成群組之取代基。
- 如申請專利範圍第8項所述之方法,其中,G表示兩個或三個選自由C1 -C4 烷基所組成群組之取代基。
- 如申請專利範圍第9項所述之方法,其中,G表示兩個或三個甲基或兩個或三個乙基。
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