CN102260551A - 用于液态烃以及其它的燃料和油的标记化合物 - Google Patents
用于液态烃以及其它的燃料和油的标记化合物 Download PDFInfo
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- CN102260551A CN102260551A CN201110151952XA CN201110151952A CN102260551A CN 102260551 A CN102260551 A CN 102260551A CN 201110151952X A CN201110151952X A CN 201110151952XA CN 201110151952 A CN201110151952 A CN 201110151952A CN 102260551 A CN102260551 A CN 102260551A
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- fuel
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- alkyl
- petroleum hydrocarbon
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 35
- 239000000446 fuel Substances 0.000 title claims description 32
- 239000003550 marker Substances 0.000 title description 13
- 239000003921 oil Substances 0.000 title description 10
- 229930195733 hydrocarbon Natural products 0.000 title description 6
- 150000002430 hydrocarbons Chemical class 0.000 title description 6
- 239000007788 liquid Substances 0.000 title description 5
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000003209 petroleum derivative Substances 0.000 claims description 24
- 239000003225 biodiesel Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 14
- 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
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 239000002283 diesel fuel Substances 0.000 description 5
- 239000003502 gasoline Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QEFMDEFYYCMJPY-UHFFFAOYSA-N 1-(chloromethyl)-2-phenylbenzene Chemical group ClCC1=CC=CC=C1C1=CC=CC=C1 QEFMDEFYYCMJPY-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- 239000002253 acid Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000012856 packing Methods 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
- 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
- ALLIZEAXNXSFGD-UHFFFAOYSA-N 1-methyl-2-phenylbenzene Chemical group CC1=CC=CC=C1C1=CC=CC=C1 ALLIZEAXNXSFGD-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 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
- 239000005864 Sulphur Substances 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
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 238000003556 assay Methods 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
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 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
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000003365 glass fiber Substances 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
- 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
- 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
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 239000003760 tallow Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 235000013311 vegetables Nutrition 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
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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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- 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
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Abstract
Description
技术领域
本发明涉及一种用来作为液态烃以及其他燃料和油的化学标记物的化合物。
背景技术
用各种化学标记物对石油烃以及其它的燃料和油进行标记的做法是本领域众所周知的。人们已经将各种化合物用于该目的,还使用很多的技术来检测标记物,例如采用吸收光谱和质谱技术。例如,美国公开申请第2007/0184555号揭示了将各种有机化合物用于对液态烃以及其它的燃料和油进行标记。但是,人们仍然需要用于这些产品的其它的标记化合物。可以将标记物的组合用作数字标记体系,用量的比例形成被标记产品的编码。人们需要其它的可以用作燃料和润滑剂标记物的化合物,以便获得尽可能多的可用编码。本发明所要解决的问题是找到另外的可以用来对液态烃以及其他燃料和油进行标记的标记物。
发明内容
本发明提供式(I)化合物
式中G表示选自以下的至少一种取代基:C1-C12烷基和C1-C12烷氧基。
本发明还提供了一种对石油烃、生物柴油燃料或者乙醇燃料进行标记的方法;所述方法包括向所述石油烃、生物柴油燃料或乙醇燃料中加入至少一种式(I)所示的化合物。
发明详述
除非另外说明,否则,百分数为重量百分数(重量%),温度的单位为℃。浓度的单位是以重量/重量计的每百万分之份数(“ppm”),或者以重量/体积计(毫克/升);优选以重量/体积计。术语“石油烃”表示主要具有烃组成的产品,但是也可以包含少量的氧、氮、硫或磷;石油烃包括原油以及源自石油精炼工艺的产品;它们包括例如原油、润滑油、液压流体、制动液、汽油、柴油燃料、煤油、喷气发动机燃料和加热油。可以将本发明的标记化合物加入石油烃、生物柴油燃料、乙醇燃料、或者它们的混合物中。生物柴油燃料是源自生物来源的燃料,其包含脂肪酸烷基酯的混合物,特别是脂肪酸甲酯。通常通过对新鲜的或再循环的植物油进行酯交换而制备生物柴油燃料,但是也可以使用动物脂肪。乙醇燃料是任何包含乙醇的燃料,可以是纯的乙醇形式,或者可以包含乙醇与石油烃的混合物,例如“酒精汽油”。“烷基”是包含1-22个碳原子的取代或未取代的烃基,具有直链或支化结构。较佳的是,本发明的化合物按照天然同位素比例包含各种元素。
G表示选自以下的至少一种取代基:C1-C12烷基和C1-C12烷氧基,即式(I)中具有“G”取代基的各个芳环包含选自以下的至少一种取代基:C1-C12烷基和C1-C12烷氧基。较佳的是,G表示各个芳环上的1-3个取代基,它们可以是相同的或者不同的,优选是两个或三个取代基,优选是两个或三个相同的取代基。但是,在两个被G取代的芳环上,“G”表示的取代基是相同的,也即是说,相对于中间联苯部分的苯环之间的对称面,所述化合物是对称的。较佳的是,G表示选自以下的至少一种取代基:C1-C6烷基和C1-C6烷氧基,优选C1-C4烷基和C1-C4烷氧基,优选C1-C4烷基,优选C1-C3烷基,优选甲基和乙基。
在本发明的方法中,优选每种标记物的最小量至少为0.01ppm,优选至少为0.05ppm,优选至少为0.1ppm,优选至少为0.2ppm。较佳的是,各种标记物的最大量为50ppm,优选20ppm,优选15ppm,优选10ppm,优选5ppm,优选2ppm,优选1ppm,优选0.5ppm。较佳的是,在被标记的石油烃、生物柴油燃料或乙醇燃料中,标记化合物无法通过观察检测到,也即是说,不可能在没有辅助条件的情况下,通过观察包含所述标记化合物的石油烃、生物柴油燃料或乙醇燃料的颜色或其他特征而进行测定。较佳的是,标记化合物是在其所加入的石油烃、生物柴油燃料或乙醇燃料中通常不会出现的化合物,无论是作为所述石油烃、生物柴油燃料或乙醇燃料自身的组分出现,或者作为石油烃、生物柴油燃料或乙醇燃料中使用的添加剂出现。
较佳的是,所述标记化合物的log P值至少为3,其中P是1-辛醇/水分配系数。较佳的是,所述标记化合物的log P至少为4,优选至少为5。没有在文献中通过试验测定并报道的Log P值可以通过Meylan,W.M &Howard,P.H.,I Pharm.Sci.,第84卷,第83-92页(1995)所述的方法预测。较佳的是,所述石油烃、生物柴油燃料或乙醇燃料是石油烃或生物柴油燃料;优选是石油烃;优选是原油、汽油、柴油燃料、煤油、喷气发动机燃料或加热油;优选是汽油。
在本发明的一个实施方式中,通过以下方式检测标记化合物,通过色谱技术将其至少部分地从所述石油烃、生物柴油燃料或乙醇燃料的组分中分离,所述色谱技术包括例如气相色谱、液相色谱、薄层色谱、纸色谱、吸附色谱、亲合性色谱、毛细管电泳、离子交换和分子排阻色谱。在进行色谱操作之后,进行以下操作中的至少一种:(i)质谱分析,以及(ii)FTIR。标记化合物的种类优选通过质谱分析测定。较佳的是,在不进行任何分离的条件下,通过质谱分析测定石油烃、生物柴油燃料或乙醇燃料中的标记化合物。或者,可以通过例如蒸馏掉石油烃或乙醇的一些挥发性较强的组分,将标记化合物浓缩,然后进行分析。
较佳的是,存在超过一种标记化合物。通过使用多种标记化合物能够促进在石油烃、生物柴油燃料或乙醇燃料中结合编码的信息,该编码的信息可以用来鉴别所述石油烃、生物柴油燃料或乙醇燃料的来源以及其它的特征。所述编码包括标记化合物的种类以及相对量,例如固定整数比。可以使用一种、两种、三种或更多种标记化合物形成所述编码。可以将本发明的标记化合物与其他种类的标记物(例如通过吸收光谱测定的标记物)组合,所述其他种类的标记物包括以下文献所述的那些:美国专利第6,811,575号;美国专利申请公开第2004/0250469号以及欧洲申请公开第1,479,749号。标记化合物被直接加入石油烃、生物柴油燃料或乙醇燃料中,或者加入包含其他化合物的添加剂包装中,例如用于润滑剂的抗磨损添加剂,用于汽油的清洁剂等,将所述添加剂包装加入石油烃、生物柴油燃料或乙醇燃料中。
本发明的化合物可以通过本领域已知的方法制备。例如,可以根据下式,用4,4’-双氯甲基-1,1’-联苯对取代的苯进行烷基化
用于取代的苯的烷基化的常规路易斯酸适合用于该方法。较佳的是,所述取代的苯仅在1,4-位或者1,3,5-位有取代基,这使得烷基化反应制得的产物仅有一种可能的位置异构体。例如,如果取代的苯是1,4-二甲基苯,则产物具有以下结构:产物中的甲基在2位和5位。
实施例
实施例1:4,4’-双(2,5-二甲基苄基)-1,1’-联苯的制备
在100毫升的烧瓶中加入4,4’-双(氯甲基)-1,1’-联苯(10g)和对二甲苯(25毫升)。在室温下,在搅拌的条件下向澄清溶液加入四氯化钛(6滴),该混合物立刻变成深棕色。在室温下搅拌过夜之后,加入乙醇(2毫升)以破坏催化剂,该混合物变成浅米色悬浮液。将该混合物转移到分液漏斗中,用稀盐酸水溶液洗涤,然后用碳酸氢钠饱和水溶液洗涤。有机层用硫酸镁干燥,使用旋转蒸发仪,在真空条件下浓缩至干。棕褐色的固体用甲苯重结晶,制得白色晶体产物,mp=144.6℃。GC/MS,HNMR,CNMR和IR均与所需产物相符。
实施例2:4,4’-双(4-甲基苄基)-1,1’-联苯的制备
在500毫升的烧瓶中加入4,4’-双(氯甲基)-1,1’-联苯(25.1g)和甲苯(300毫升)。在室温下,在搅拌的条件下向澄清溶液加入四氯化钛(1毫升),该混合物立刻变成深棕色。5分钟后,加入第二整份1毫升的催化剂。在室温下搅拌过夜之后,加入乙醇(10毫升)以破坏催化剂,该混合物变成浅米色悬浮液。在旋转蒸发仪中,在真空条件下将有机层浓缩至干。棕褐色固体悬浮在200毫升沸腾的甲苯中,用MgSO4处理。通过玻璃纤维滤纸真空过滤,制得透明溶液,趁热向其中加入200毫升庚烷。将该略微混浊的溶液冷却至室温,然后在冷冻器中过夜,以完成结晶。回收得到白色晶体,17.4克,mp=161.8℃。GC/MS,HNMR,CNMR和IR均与所需产物相符。
实施例3:商业柴油燃料的标记
将4,4’-双(2,5-二甲基苄基)-1,1’-联苯以0.1ppm的浓度加入商业柴油燃料,所述商业柴油燃料购自当地的马拉松加油站(local Marathon fillingstation)。通过GC/MS对标记的燃料进行分析,所述GC/MS设备使用尺寸为15米×内径0.25毫米×0.25微米的Agilent DB-35ms柱。采用以下温控程序对样品进行分析:起始温度100℃,以20℃/分钟的速率升温至280℃,保持10分钟,然后以20℃/分钟的速率升温至340℃,保持6分钟,最后以20℃/分钟的速率升温至360℃,保持1分钟。很容易地用SIM:390测定4,4’-双(2,5-二甲基苄基)-1,1’-联苯。重复分析(n=6)表明相对标准偏差(RSD)小于5%。
实施例4:4,4’-双(2,5-二甲基苄基)-1,1’-联苯的稳定性和可萃取性
采用以下步骤,使用包含100-1000ppm标记物以及等量的角鲨烯内部参比标样的二甲苯溶液,测量标记物的稳定性和可萃取性。
洗涤:
在100毫升的小瓶中将95份标记的二甲苯与5份洗涤剂混合。使用磁力搅拌子温和地混合8小时。停止混合,取出二甲苯溶液等分样。通过GC进行分析,将标记物的响应结果与参比(未洗涤的)样品进行比较。洗涤剂:
1)5%硫酸
2)98%硫酸
3)5%NaOH溶液
4)50%NaOH溶液
5)活性炭(使用98份二甲苯溶液以及2份炭)
6)5%漂白剂
为了测量金属吸附性,在室温下,用5克金属碎屑对100毫升标记的二甲苯测试溶液处理8小时。再次通过GC分析测定标记物吸附到金属表面上造成的任何损失。
样品 | 标记物面积 | 内标面积 | 比例 | 标记物 | 变化% |
参比 | 172357 | 189770 | 0.91 | 100.00 | 0.00 |
5%NaOH | 180432 | 193264 | 0.93 | 102.79 | -2.79 |
50%NaOH | 174722 | 195774 | 0.89 | 98.26 | -1.74 |
5%H2SO4 | 171384 | 192065 | 0.89 | 98.25 | -1.75 |
98%H2SO4 | 180035 | 197296 | 0.91 | 100.47 | 0.47 |
2%炭 | NA | NA | NA | 94 | -6 |
5%漂白剂 | NA | NA | NA | 35 | -65 |
金属 | NA | NA | NA | 104 | +4 |
Claims (10)
2.如权利要求1所述的化合物,其特征在于,G表示选自以下的至少一种取代基:C1-C6烷基。
3.如权利要求2所述的化合物,其特征在于,G表示选自以下的两种或三种取代基:C1-C6烷基。
4.如权利要求3所述的化合物,其特征在于,G表示选自以下的两种或三种取代基:C1-C4烷基。
5.如权利要求4所述的化合物,其特征在于,G表示两个或三个甲基,或者两个或三个乙基。
7.如权利要求6所述的方法,其特征在于,式(I)的各种化合物的含量为0.05-20ppm。
8.如权利要求7所述的方法,其特征在于,G表示选自以下的两种或三种取代基:C1-C6烷基。
9.如权利要求8所述的方法,其特征在于,G表示选自以下的两种或三种取代基:C1-C4烷基。
10.如权利要求9所述的方法,其特征在于,G表示两个或三个甲基,或者两个或三个乙基。
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CN103620009A (zh) * | 2011-06-30 | 2014-03-05 | 安格斯化学公司 | 用于液体烃以及其它的燃料和油作为标记物的双酚醚化合物 |
CN104822805B (zh) * | 2012-12-06 | 2017-08-22 | 陶氏环球技术有限责任公司 | Thpe醚 |
CN109863146A (zh) * | 2016-09-01 | 2019-06-07 | 百时美施贵宝公司 | 用作免疫调节剂的联芳基化合物 |
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JP5851593B2 (ja) | 2011-05-09 | 2016-02-03 | ダウ グローバル テクノロジーズ エルエルシー | 炭化水素並びに他の燃料および油の標識としてのオルト−フェニルフェノール化合物 |
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