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 PDF

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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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George David Green
Raymond John Swedo
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Description

用於液體碳氫化合物及其他燃料與油之標記物化合物
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。
[實施例] 實施例1:4,4’-雙(2,5-二甲基苯甲基)-1,1’-聯苯之製備
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。
實施例2:4,4’-雙(4-甲基苯甲基)-1,1’-聯苯之製備
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。
實施例3:商用柴油燃料之標記
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)。
實施例4:4,4’-雙(2,5-二甲基苯甲基)-1,1’-聯苯之安定性和可萃取性
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)

  1. 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。
  2. 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。
  3. 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。
  4. 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。
  5. 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。
  6. 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: 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。
  7. 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。
  8. 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。
  9. 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。
  10. 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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