TW200410974A - Pyrazinoporphyrazines as markers for liquid hydrocarbons - Google Patents
Pyrazinoporphyrazines as markers for liquid hydrocarbons Download PDFInfo
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- TW200410974A TW200410974A TW092117668A TW92117668A TW200410974A TW 200410974 A TW200410974 A TW 200410974A TW 092117668 A TW092117668 A TW 092117668A TW 92117668 A TW92117668 A TW 92117668A TW 200410974 A TW200410974 A TW 200410974A
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Description
200410974 玖、發明說明: 【發明所屬之技術領域】 本發明大體係關於一種使用吡嗪並紫菜嗪化物標記石油 烴以供後續識別使用之方法。 【先前技術】 M. Matsuoka 在 Near-Infrared Dyes for High Technology Applications (S. Daehne等編著),203-231 頁之“NIR Dyes for Information Recording”中,揭示了將p比嗪並紫菜唤化物用於 固態光學資訊記錄系統,例如,可記錄光碟。然而,該文 獻沒有提出一種標記石油烴之方法。 本發明所針對之問題係發現一種適用於石油烴之標記 物。 【發明内容】 本發明旨在一種標記液態石油烴之方法。該方法包括將 具有700 nm至900 nm之最大吸光值之咕嗔並紫菜嗓化物染 料加入液態石油烴。 【實施方式】 除非另外說明,所有百分比均為重量百分比。以每百萬 分之份數計之濃度(“ppm”)係以重量/體積基礎計算。術語 “石油烴”指來自石油精練製程而主要為烴組合物之產品, 唯其可含有少量之氧、氮、硫或磷,,以潤滑油、液壓流 體、刹車油、汽油、柴油、煤油、噴氣燃料及加熱油為佳。 “烷基”係指在直鏈、支鏈或環排列中具有1至20個碳原子之 烴基基團。烷基視需要可具有一個或多個雙或參键。允許 在烷基上具有一個或多個i基、羥基、烷氧基、烷醯基或 200410974 芳醯基之取代。烷基基團以不具有鹵基或烷氧基取代為 佳。“烷氧基”係與一氧原子相連之烷基,即烷基取代之和 基。“雜烷基”係具有至少一個被〇、nr或s替代之碳原子之 燒基’其中R係氫、纟元基、雜燒基、芳基或芳燒基。‘‘芳基,, 係衍生自芳香烴化合物之取代物 〜π 'm/、固尸:
原子’且具有一個或多個獨立或稠和環。“芳燒基,,係被‘ς V 基”取代之“烷基”。“雜環”基團係衍生自具有5至20個環原子
之雜環化合物之取代物,其中至少一個係氮、氧或硫。雜
環基團以不含硫為佳。允許在雜環上具有一個或多個I 基、氰基、羥基、烷基、雜烷基、烷醯基、芳醯基或烷氧 基之取代。芳基和雜環基團以不含南素原子為佳。“芳香雜 環”基團係衍生自芳香雜環化合物之雜環基團。 曰π “有機官能團”係指一不含金屬原子之官处 旎基團,且其且 有m2個碳原子、氫原子,及視需要之雜原子,該雜W 包括,但不限於氮、氧、硫、磷、石夕和_素原子。有機官 能團視需要可包含雙和/或參鍵;相連或稠合之環;及如
該基團全部或部分為脂肪族,脂肪族部衣 口 ^ 可為線性或支鏈。 外匕嗪並紫菜嗪化物染料,,係含紫菜嗪 如下所示。 -系統之化合物’
200410974 其中一吡嗪環通過其2-及夂位盥此γ a卢系姑击― Ή紧菜唤%糸統中母個。比p各 環之3-和4·位稠合’每個吡嗪環還被一芳基或芳香雜環基團 取代’該取代基以單鍵與心環相連或與ρ比嗪環铜合。 在本發明之-較佳具體實施方案中"比嗪並紫㈣化物
二了,…于;過渡金屬、梦或銘; =多個氧、幾化物、齒素或-種有機官能團取代之i 代表一與錫稠合之 壤基團。較佳地’ Μ代表兩個氫原子;鋼、鐵q 或氧,羥化物,銅、鐵、4 4或矽 、 鐵鋁或矽(鏈烷鉍鹽或醇鹽。乂取< 物之貫例包括,但不限於苯並、吡咯並、呋 莕並或苯並呋喃並。 並、^丨嗓並 在本發明之-較佳具體實施方案中,式 或被苯並取代之取代基,且所得❹並紫代表-苯」 吡嗪並紫菜嗪化物”)具有式⑼結構:來“匕物(“苯」 200410974
J:中 R1、R2 3 κ (Π) /、 R、R4、R)、R6、R7、R8、R9、V。、Rll 12 浐 、、和R16獨立地係氫或有機官能團,或位在相多 又任何成對R基團結合形成一脂肪族、芳香 環環系統,兮戸^ 妖万香狹或令 t μ 5衣系統與和R基團對相連之苯並基團稠人。4 佳;R、R2、R3、R4、R5、R6、R7、R8、R9、Ri。、R11 r12
Rl3、Rl4、R15和 R1&、「甘 、· 和R獨亙地係氫;烷基;雜烷基;芳基〆 二基:=;羥基或被烷基、雜烷基、芳基、芳烷:、病 :二:Τ芳酿基取代之經基;氰基;硝基;燒酿基 ::二t二胺或被燒基、雜燒基、芳基、芳燒基、矣 或芳㈣取代之胺;縣;垸基、芳垸基、者 :基或旨基團;未取代或被燒基、雜燒基、芳基q 火凡基4 %、k gi基或芳驢基取代之醯胺|目;或位在才 ^ 、之任何成對R基團結合形成一脂肪族、芳香族i 隹s "亥環系統與和R基團對相連之笨並基團稠合 200410974 在 八,XV、K1、R1 及 R16係氩。較佳地,R2、、R6、R7、R1G、Rn、i 獨立地係氫、烷基、芳基或雜環芳基;更佳地,R2、、 r6、r7、Rl〇、^1、RliR15獨立地係芳基或雜環芳基。在一 較隹異體實施方案中,較佳地R2、R3、r6、r7、Ri〇 " r14及R15係苯基。 、R 、 在本發明之另一較佳具體實施方案中,式⑴中X代表含有 5元雜環之芳香雜環環系統,且芳香雜環系統通過5元^環 與式(I)中每個吡嗪環裯合而相連。較佳地,5元雜環係吡咯 或吹p南環,其可分別在其2-和3-位,或3-和4-位上與p比嗪環 稠合,如下所示。
當五員雜環在2-和3-位上稠合時,環視需要可為一更大之多 環芳香雜環系統之部分,例如,4哚。當五員雜環在2_和 3-位上稠合時,依據四個“γ”基團相互之定向,所得吡嗪並 紫菜嗪化物具有幾種可能之異構體。最對稱之異構體如 式(III)所描述: 200410974
17 R 18 R
N 19
^ N
N
R
,20
N N N >24
N N
N R23 其中Y係〇或NR25
N
,21
R22 " (in) R17、R18、R19、R20、R21、R22、R23、R 24 及R獨二地係氫或有機官能團;或與相鄰環原子相連之任 何成對R基團結合形成一脂肪族、芳香族或雜環環系統,該 裱系統與和R基團對相連之吡咯或呋喃環稠合。較佳地,
Rl7、Rl8、Rl9、R2G、R21、R22、R23、R24及 R25獨立地係氫;燒 基;雜燒基;芳基;芳垸基;自基;經基或被燒基、雜燒 基、万基、万烷基、雜環、烷醯基或芳醯基取代之羥基; 氰基’硝基’ fe驗基、芳驢基;雜環;胺或被⑥基、雜燒 基万基万烷基、雜環、烷醯基或芳醯基取代之胺;羧 基;烷基、芳烷基、雜烷基或雜環酯基團;未取代或被烷 基、4 k基、万基、芳境基、雜環、燒酿基或芳酸基取代 之醯胺基團;或在相粼石卢;^ 1, #反原子上之任何成對R基團結合形成 一脂肪族、芳香族或雜提$ 3 旅衣J衣系統,該環系統與和R基團對相 連之吡咯或呋喃環稠合。 -11 - 200410974 在一較佳鼻體實施方案中,在具有在2-和%位上與 p比嗔裥R19、 合之吡咯或呔喃環之吡嗪並紫菜嗪化物中,Rn、r18 R2〇、R2\ r22、R23&r24結合形成與吡咯或呋喃環稠合之4 並基團。依據四個“Y”基團相互之定向,所得仆八 ^ 丁 口物具有幾 種可能之異構體。最對稱之異構體如下式αν)所描述· 30
(IV) 其中 R26、R27、R28、、r30、r31、r32、r33、r34、R35 6 39、tn 4q K R37、R38、R \ 及R41獨立地係氫或有機官能團;或與才 碳原子相連 < 任何成對尺基團結合形成一脂肪族、表、 鄰 或雜環環系6统環系統與和R基團對相連之笨並環稠人 較佳地,尺 R28、R29、R30、R31、R32、R33、r34、尺35 -12- 200410974 R36、R37、R38、r39、R4〇及r41獨立地係氫;烷基;雜烷基; 芳基;芳基;鹵基;輕基或被燒基、雜燒基、芳基、芳 虎基、雜環、烷醯基或芳醯基取代之羥基;氰基;硝基;
燒醯基、芳醯基;雜環;胺或被烷基、雜烷基、芳基、芳 燒基、雜環、烷醯基或芳醯基取代之胺;羧基;烷基、芳 燒基、雜烷基或雜環酯基團;未取代或被烷基、雜烷基、 芳基、芳燒基、雜環、烷醯基或芳醯基取代之醯胺基團; 或在相鄰碳原子上之任何成對R基團結合形成一脂肪族、芳 香族或雜環環系統,該環系統與和R基團對相連之苯並環稠 合0 在一較佳具體實施方案中,γ係NR25,且R25係烷基,較佳 地係至少C4燒基’最佳地係未取代之飽和燒基。較佳地,R27 和R28中至少一個,R3^R32中至少一個,r35和r36中至少一 個及R39和R4Q中至少一個係烷基,較佳地係至少C4烷基,最 佳地係未取代之飽和烷基。
車父佳地’母個加入石油烴之p比唤並紫菜嗪化物染料之量 為至少0.01 ppm,更佳地為至少0 02 ppm,且最佳地為至少 0.03 ppm。較佳地,每個吡嗪並紫菜嗪化物染料之量低於1〇 ppm ’更佳地低於2 ppm,且最佳地低於1 pp1T^標記以不可 見為佳,即不能通過簡單之目視觀察被標記烴觀測到染 料。較佳地,本發明方法使用之具有7〇〇腿至9〇〇 nm範圍内 之最大吸光值之吡嗪並紫菜嗪化物染料具有至少71〇 波 長之最大吸光值,更佳地至少72〇 nm,且最佳地至少750 疆,較佳地’最大吸光值不大於88〇 nm,更佳地不大於860 -13 - 200410974 nm。在一具體實施方案中,至少兩種具有不同波長之最大 吸光值之吡嗪並紫菜嗪化物染料被加入石油烴中。在另一 具體貫施方案中’將至少一種P比嗅並紫菜唤化物染料和至 少一種具有700 nm至900 nm範圍内(較佳地72〇腿至900 _範 圍内)之最大吸光值之其他染料加入石油烴中。較佳地,每 種在此範圍有吸收之其他染料以至少〇 〇1 ppm,更佳地至少 0·〇2 ppm,最佳地至少〇·03 ppn^量存在。較佳地,每種其
他染料之量低於10 ppm,更佳地低於2 ppm,且最佳地低於工 ppm 〇 較佳地,通過將標記之石油烴暴露於具有包含染料最大 吸光值之光瑨中一邯分波長之電磁射線下,並探測其對光 或螢光發射之吸收來檢測本發明使用之染料。最好檢測設 備能計算標記之石油烴中染料濃度和濃度比例。當其以至
少〇.〇lppm含量存在時,本領域熟知之典型分光光度計能法 測本發明使用之吡嗪並紫菜嗪化物染料。最好使用美國』 利5,225,679描述之檢測器,尤其係從R〇hm* h咖公^ (Philadelphia,PA)獲得之SpecTraceTM分析器。此等分析器使j 依據染料吸收光譜選擇之濾光器,並通過多元線性回歸^ 法進行仏號《化學計量學分析,&減少信號·雜訊比。 當檢測未涉及對標記石油烴進行任何化學處理時,測言 後樣品可放回其來源,從而避免了處理和處置危險化^ 之必要。例如’當染料僅通過測量其標記之石油烴樣品^ 光吸收度來進行檢測時,情況正係如此。 在本發明之—具體實施方案中,該染料係調配於以 -14 - 200410974 中,以便將其加入液態石油烴。吡嗪並紫菜嗪化物染料之 較佳溶劑係芳香烴溶劑。染料於溶劑中中之濃度以〇·1°/〇至 10%為佳。
在本發明之一具體實施方案中,將至少一種吡嗪並紫菜 喚化物染料,和視需要之另一具有700 nm至900 nm範圍内最 大吸光值之染料加入石油烴,其中具有至少一種可見染 料,即一種具有500 nm至700 nm範圍内之最大吸光值之染 料,較佳地550 nm至700 nm,且最佳地550 nm至680 nm。較 佳地,每種可見染料加入量為至少1 ppm,較佳地為至少2 ppm,且最佳地為至少5 ppm。較佳地,每種可見染料之量 不超過20 ppm,更佳地不超過15 ppm。在一較佳之具體實施 方案中,可見染料選自蒽醌類及偶氮類染料。具有在此區 域之最大吸光值之合適惠硫染料包括,例如,具有燒基胺 基、芳基·胺基或芳香雜環胺基取代基之1,4-二取代蒽醌。具 有在此區域之最大吸光值之合適偶氮染料包括,例如,那 些具有結構Ar-N=N-Ar-N=N-Ar之物質,其中Αι·係芳基,且每 個Ar可以不同。根據比色指數列出具有在此區域内之最大 吸光值之適合之商業蒽醌及偶氮染料之具體實例,其包括 C.I.溶劑藍98、C.I.溶劑藍79、C.I.溶劑藍99和C.I.溶劑藍 100 ° 摻入至少一種具有700 nm至900 nm區域内之最大吸光值 之吡嗪並紫菜嗪化物染料,使得可通過分光光度方法,在 光譜區域内相對無干擾地識別液體石油烴。在此區域内可 檢測到低含量之此等染料,可得到一低成本之標記方法, -15- 200410974 比例之資 燃料標記 且多種染料之可獲得性允許編碼有關染料用量及 訊。由於此等原因,在此範圍内有吸收且適於作 物之其他化合物也係非常有用的。 也可聯合使用在700 nm至900 nm内可檢測到之標^己物~ 在可見光範圍内可檢測到之標記物。摻入更高含量之s… 一種具有500 nm至700 nm區域内之最大吸光值之可見仇 料’更便於在此區域内之定量分光光度測定。準確測定= 料含量使得染料量及比例可作為識別烴之編碼之一部分。 因為在此區域有吸收之染料常較便宜,所以使用更高:量 標記方法之總費用。因此,聯合使 木枓可増加標記方法之靈活性及降低其費用。 如本::::::之製備方法為熟悉此项技術者所熟知。例 4月27日)·揭- /U6573 (MatSU〇ka等人,公開日期:1999年, 日)揭不了許多此類化合物之合成路徑。
-16 -
Claims (1)
- 200410974 拾、申請專利範圍· 1. 一種標記液態石油烴之方法,該方法包括於該液態石油 煙中加入具有700 nm至900 nm之最大吸光值的吡喚並紫 菜嗔化物染料。 2. 如申請專利範圍第1項之方法,其中該至少一種吡嗪並紫 菜嗪化物染料係具有通式(I)結構:其中Μ代表兩個氫原子;過渡金屬、碎或铭;或任何一 個被一或多個氧、氩、鹵素或一種有機官能團取代之過 渡金屬、矽和鋁;且X代表與吡嗪環稠合之芳環系統。 3·如申請專利範圍第2項之方法,其中該至少一種吡嗪並紫 菜嗪化物染料具有通式(II)結構: 13 R R、R、R5、R6、R7、r8、R9、R1。、H11、r12、 ^ f、R1^ Rl6係個別為氫或有機官能基團’成位在 ^奴原子上之任何成對R基團係結合形成-脂脉族、 芳香族或雜環環系統,該環系統與和該R基團對相連之 苯並基團稠合。 如申請專利範圍第2項之方法,其中χ代表包含五員雜環 之芳香雜環環系統,且芳香雜環環系統係藉由該五員雜 環與通式(I)中p比嗪環稠合而相連。 如申請專利範圍第4項之方法,其中該至少一種吡嗪並紫 米嘻化物染料係具有通式(III)結構或其具有不同Υ基團 定向之異構體: 200410974其中 Y係〇或 NR25 ; R17、R18、R19、R20、R21、R22、R23、R24 及R25個別係為氫或有機官能團;或連接於相鄰環原子之 任何成對R基團係結合形成一脂肪族、芳香族或雜環環 系統,該環系統與和R基團對相連之吡咯或呋喃環稠合。 6.如申請專利範圍第5項之方法,其中該至少一種吡嗪並紫 菜嗪化物染料具有通式(IV)結構或其具有不同Y基團定向之異構體: 2004109747. 如申凊專利範圍第!項之方法,其中每種吡嗪並紫菜嗪化 物染料 < 含量各為0·01 ?{)111至1〇卯以。 8. 如申請專利範圍第7項之方法,其中該液態石油煙選自下 列物質組成之群組:潤滑油、液壓流體、剎車油、汽油、 柴油、煤油、喷氣燃料和加熱油。 如申μ專利範圍第8項之方法,其尚包含至少一種含量為 1 ppm至20 ppm之可見染料。 9. 200410974 10.如申請專利範圍第9項之方法,其中每種吡嗪並紫菜嗪化 物染料之含量各為0.01 ppm至2 ppm,且每種可見染料之 含量各為2 ppm至20 ppm。 200410974 柒、指定代表圖: (一) 本案指定代表圖為:第()圖。 (二) 本代表圖之元件代表符號簡單說明: 捌、本案若有化學式時,請揭示最能顯示發明特徵的化學式:
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WO2012050844A1 (en) | 2010-09-28 | 2012-04-19 | Authentix, Inc. | Determining the quantity of a taggant in a liquid sample |
US9995681B2 (en) | 2010-09-28 | 2018-06-12 | Authentix, Inc. | Determining the quantity of a taggant in a liquid sample |
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TWI591339B (zh) * | 2013-05-02 | 2017-07-11 | 羅門哈斯公司 | 偵測燃料標記物之分析方法 |
WO2016077471A1 (en) | 2014-11-11 | 2016-05-19 | Altria Client Services Inc. | Method for detecting oil on tobacco products and packaging |
EP3325947A4 (en) | 2015-07-24 | 2019-01-23 | Authentix, Inc. | DETERMINATION OF THE QUANTITY OF A MARKER IN A LIQUID SAMPLE |
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