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CN103620009A - 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 - Google Patents

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 Download PDF

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CN103620009A
CN103620009A CN201280028970.1A CN201280028970A CN103620009A CN 103620009 A CN103620009 A CN 103620009A CN 201280028970 A CN201280028970 A CN 201280028970A CN 103620009 A CN103620009 A CN 103620009A
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G·D·格林
R·斯韦多
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Abstract

一种对石油烃或液体生物来源的燃料进行标记的方法，所述方法通过向所述石油烃或液体生物来源的燃料中加入至少一种通式(I)所示的化合物来进行标记，
Figure DDA0000436149980000011
其中，R表示C1-C18烷基、C3-C18烯基或C3-C18炔基。

Description

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
本发明涉及一种使用合适的化合物标记液体烃以及其他燃料和油的方法。
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用途，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，美国专利第7,858,373号揭示了将各种有机化合物用于对液体烃以及其它的燃料和油进行标记。但是，人们一直需要用于这些产品的其它的标记化合物。可在量的比例形成被标记产品的编码的情况下，将标记物的组合用作数字标记体系。人们希望有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体烃以及其他燃料和油进行标记的标记物。
发明内容
本发明提供了一种对石油烃或液体生物来源的燃料进行标记的方法；所述方法包括向所述石油烃或液体生物来源的燃料中加入至少一种通式(I)所示的化合物
Figure BDA0000436149970000011
其中，R表示C1-C18烷基、C3-C18烯基或C3-C18炔基。
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/重量计或者以重量/体积计(毫克/升)的每百万分之份数(“ppm”);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，但是它们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。可将本发明的标记化合物添加至石油烃或液体生物来源的燃料；后者的例子是生物柴油燃料、乙醇、丁醇、乙基叔丁基醚或其混合物。如果一种物质在20℃时为液态，则认为该物质是液体。生物柴油燃料是生物来源的燃料，包含脂肪酸烷基酯，特别是脂肪酸甲酯的混合物。通常通过对新的或再循环的植物油进行酯交换而制得生物柴油燃料,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1-18个碳原子的取代或未取代的烃基，其可具有直链、支化或环状结构，或其组合。“烯基”或“炔基”分别是包含1个或多个双键或三键的烷基。可以用一个或多个羟基或烷氧基在烷基上进行取代。较佳的是，烷基是未取代的。较佳的是，烷基是非环状的。较佳的是，本发明的化合物包含的各种元素按照其天然同位素比例存在。
较佳的是，R表示C1-C18烷基或C3-C18烯基，优选C2-C18烷基或C3-C18烯基，优选C1-C18烷基，优选C3-C16烷基或C3-C16烯基，优选C2-C18烷基，优选C4-C16烷基或C4-C16烯基，优选C4-C16烷基，优选C5-C16烷基，优选C8-C14烷基。在通式(I)中，所述-OR基团可以在苯环上的任意位置，优选在每个环上的位置相同（例如2,2’-或4,4’-取代），优选地，所述-OR基团在苯环上的2,2’-位置，即通式(I)的化合物具有以下结构：
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0.02ppm,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，标记化合物的最大总量为100ppm，优选70ppm，优选50ppm，优选30ppm，优选20ppm，优选15ppm，优选12ppm，优选10ppm，优选8ppm，优选6ppm，优选4ppm，优选3ppm，优选2ppm，优选1ppm。较佳的是,在被标记的石油烃或液体生物来源的燃料中，标记化合物无法通过目视检测到,也就是说，不可能通过肉眼观察颜色或其它特征来测定石油烃或液体生物来源的燃料是否包含标记化合物。较佳的是，标记化合物不是其所加入的石油烃或液体生物来源的燃料中天然存在的化合物，也并不作为石油烃或液体生物来源的燃料本身的组分，或者作为其中使用的添加剂。
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值可以使用Meylan,W.M&Howard,P.H.,IPharm.Sci.,第84卷,第83-92页(1995)所揭示的方法估算。较佳的是，所述石油烃或液体生物来源的燃料是石油烃、生物柴油燃料或乙醇燃料；优选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。
较好的是，通过以下方式检测标记化合物，使用色谱技术将标记化合物至少部分地从所述石油烃或液体生物来源的燃料的组分中分离,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。标记化合物的鉴别优选通过质谱分析确定。较佳的是，在不进行任何分离的条件下，使用质谱分析检测石油烃或液体生物来源的燃料中的标记化合物。或者，可以通过例如蒸馏掉石油烃或液体生物来源的燃料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。使用多种标记化合物便于将它们混入有编码的信息的石油烃或液体生物来源的燃料中，该编码的信息可以用来鉴别所述石油烃或液体生物来源的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或液体生物来源的燃料中，或者加入包含其它化合物的添加剂包装中,例如用于润滑剂的抗磨损添加剂,用于汽油的洗涤剂等中,将所述添加剂包装加入石油烃或液体生物来源的燃料中。
本发明的化合物可以通过本领域已知的方法制备。例如，在存在碱的条件下，根据以下方程式，烷基卤化物可以与双酚进行反应
Figure BDA0000436149970000041
实施例
双酚醚的合成如以下实施例所述：
2,2’-二(十二烷氧基)-1,1’-联苯：100毫升三颈烧瓶装配了磁力搅拌器、带有氮气保护的回流冷凝器、以及带有温度控制器和热电偶的加热罩。将3.74克(0.02摩尔)2,2’-双酚、2.8克(0.04摩尔，85重量％)氢氧化钾和25毫升二甲亚砜加入烧瓶中。在氮气下对混合物进行搅拌同时加热至100℃。约21/2小时后，氢氧化钾已经溶解，将混合物冷却至约70℃。一次性加入十二烷基溴(9.60毫升；d1.038；9.97克；0.04摩尔)。观察到放热至约86℃。放热减退后，在70℃下对反应混合物进行搅拌。约5小时后，将反应混合物倒入约400毫升水中。通过过滤收集分离的白色固体，用几份水分几次在过滤器上对其进行洗涤。首先对该固体进行空气干燥，然后在50℃下的真空烘箱中干燥约2小时。产物的产量为9.49克(91%)，熔点为33-35℃。用IR、1H-NMR、13C-NMR和GC/MS分析来确认结构。
在当反应混合物在水中猝灭后产物以油状物形式分离出来的情况中，使用乙醚进行提取来代替过滤。
制备的2,2’-双酚醚：
R 产率% MP,℃
n-C8H17(BOct-BBPh) 94 (油状物)
n-C10H21(BDec-BBPh) 97 (油状物)
n-C12H25(BDD-BBPh) 91 33–35
n-C14H29(BTD-BBPh) 94 33-35
双酚醚的GC性能
使用FID(火焰离子化检测器)完成检测。
GC参数比较：
Figure BDA0000436149970000051
Figure BDA0000436149970000052

Claims (9)

1.一种对石油烃或液体生物来源的燃料进行标记的方法；所述方法包括向所述石油烃或液体生物来源的燃料中加入至少一种通式(I)所示的化合物
Figure FDA0000436149960000011
其中，R表示C1-C18烷基、C3-C18烯基或C3-C18炔基。
2.如权利要求1所述的方法，其特征在于，通式(I)的各种化合物的含量为0.01-20ppm。
3.如权利要求2所述的方法，其特征在于，-OR基团在通式(I)的苯环上的2,2’-位置上。
4.如权利要求3所述的方法，其特征在于，R表示C2-C18烷基或C3-C18烯基。
5.如权利要求4所述的方法，其特征在于，通式(I)的各种化合物的含量为0.01-10ppm。
6.如权利要求5所述的方法，其特征在于，R表示C3-C16烷基或C3-C16烯基。
7.如权利要求6所述的方法，其特征在于，所述方法还包括通过质谱分析检测通式(I)的化合物。
8.如权利要求7所述的方法，其特征在于，R表示C4-C16烷基。
9.如权利要求8所述的方法，其特征在于，所述石油烃或液体生物来源的燃料是石油烃、生物柴油燃料或乙醇燃料。
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