CN1092098A - 用作矿物油标识物的苯胺 - Google Patents

用作矿物油标识物的苯胺 Download PDF

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CN1092098A
CN1092098A CN93121269A CN93121269A CN1092098A CN 1092098 A CN1092098 A CN 1092098A CN 93121269 A CN93121269 A CN 93121269A CN 93121269 A CN93121269 A CN 93121269A CN 1092098 A CN1092098 A CN 1092098A
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group
alkyl
unsubstituted
aniline
formula
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CN1045101C (zh
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R·迪利克·布伦茨革
F·W·劳弗茨
U·施勒舍
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BASF SE
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  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

式I的苯胺用于标识矿物油，并在矿物油中检测 所说的苯胺。
Figure 93121269.3_AB_0
其中R1，R2，R3，R4，R5，R6和R7的定义如说明 书所述。

Description

本发明是关于式Ⅰ苯胺用于标识矿物油的应用，用所说的苯胺标识的矿物油和关于在矿物油中测定所述苯胺的方法：
Figure 931212693_IMG3
其中R1和R2各自分别为氢，未取代的或取代的C1-C18烷基和可以被醚官能团中的1至3个氧原子或被1至3个C1-C4烷基亚氨基间断的未取代的或取代的C1-C18烷基，或C3-C18链烯基或未取代的或取代的苯基，或者R1和R2连同与其相连的氮原子一起形成可以另外再含有杂原子的5元或6元的饱和杂环基，或者R1可以是式为OL1或NL1L2的基团，其中L1和L2各自分别为氢，未取代或取代的C1-C18烷基，C3-C18链烯基或者是未取代或取代的苯基，R3和R7各自分别为氢，未取代或取代的C2-C18烷基，C2-C18链烯基，氰基，硝基，甲酰基，未取代或取代的C2-C4链烷酰基，甲酰氨基，未取代或取代的C2-C4链烷酰氨基，苯甲酰氨基或式为OL1，CH2COOL1，NL1L2，SL1或SO2NL1L2的基团，其中L1和L2分别具有如上所述的含义，或与R2连在一起表示未取代的或被1至3个甲基取代的C2或C3烯基或者是未取代的或苯基取代的C2或C3亚烯基，R4是氢，未取代或取代的C1-C18烷基，C2-C18链烯基，硝基或式为OL1，NL1L2，COOL1或SO2L1L2的基团，其中L1和L2分别具有如上所述的含义，R5和R6各自分别为氢，未取代的或取代的C1-C18烷基，C2-C18链烯基，未取代的或取代的苯基，硝基，甲酰氨基，未取代的或取代的C2-C4烷酰氨基，苯甲酰氨基或式为OL1，NL1L2，SO2NL1L2，SO2L3，COL1或COOL1的基团，其中L1和L2分别如上述定义，L3是未取代的或取代的C1-C18烷基，C3-C18链烯基或者是未取代的或取代的苯基，上述定义的先决条件是基团R3，R5或R7中至少有一个基团为氢。
US-A-4209302中公开了α或β萘胺用于标识矿物油的应用，其中在所说的萘胺的氨基上带有一个被另一个氨基所取代的丙基。标识物是通过将萘胺与重氮化2-氯-4-硝基苯胺反应来检测。但是已知发现这种标识和检测方法还不能完全令人满意。
本发明的目的是提供标识矿物油的新试剂。这类新试剂应易于获得和易溶于矿物油。而且它们应能用简单的方法来检测。另外，即使在使用很少量标识物的情况下也应能通过强的显色反应变成可见。最后，这类标识物应不能通过用水的简单萃取而将其从所标识的矿物油中除去。
我们发现上述这一发明目的已经达到和本文开头定义的式Ⅰ苯胺可以有效地被用来标识矿物油。
在上述式Ⅰ中的所有烷基和链烯基可以是直链的和支链的。
必须认识到，就本发明来说，作为主要基团的链烯基具有1至3个双键。
如果上述的式Ⅰ中具有取代的烷基，则合适的取代基是例如羟基，C1-C4烷氧基，苯氧基，氰基，苯基，C1-C4二烷基氨基，C1-C4烷酰氧基，1-C1-C4烷氧基-C2-C4烷氧基，N-C1-C4烷基-N-羟基-C2-C4烷基氨基甲酰基，C1-C4烷氧基羰基，苯氧基羰氧基，C1-C4烷基氨基羰氧基，苯氨基羰氧基或乙酰乙酰氧基。烷基通常具有1或2个取代基。
如果上述式Ⅰ中有取代的苯基，则合适的取代基为例如，C1-C4烷基或C1-C4烷氧基。苯基通常具有1至3个取代基。
如果R1和R2及与其相连的氮原子一起构成可进一步含有其他杂原子的5元或6元饱和杂环基团时，其合适基团的实例为吡咯烷基，哌啶基，吗啉基，哌嗪基或N-C1-C4烷基哌嗪基。
R1，R2，R3，R4，R5，R6，R7，L1，L2和L3为例如甲基，乙基，丙基，异丙基，丁基，异丁基，仲丁基，戊基，异戊基，新戊基，叔戊基，己基，2-甲基戊基，庚基，辛基，2-乙基己基，异辛基，壬基，异壬基，癸基，异癸基，十一烷基，十二烷基，十三烷基，3，5，5，7-四甲基壬基，异十三烷基（上述的异辛基，异壬基，异癸基和异十三烷基都俗名，它们是通过OXO合成从醇制得的;参见Ullmanns Encyklopadie der technischen Chemie，第4版，第7卷，第215-217页和第11卷，第435和436页），十四烷基，十五烷基，十六烷基，十七烷基，十八烷基，2-甲氧基乙基，2-乙氧基乙基，2-丙氧基乙基，2-异丙氧基乙基，2-丁氧基乙基，2-或3-甲氧基丙基，2-或3-乙氧基丙基，2-或3-丙氧基丙基，2-或3-丁氧基丙基，2-或4-甲氧基丁基，2-或4-乙氧基丁基，2-或4-丙氧基丁基，2-或4-丁氧基丁基，氰基甲基，2-氰基乙基，3-氰基丙基，2-氰基丁基，4-氰基丁基，5-氰基戊基，6-氰基己基，2-羟基乙基，2-羟基丙基，3-羟基丙基，2-羟基丁基，4-羟基丁基，5-羟基戊基，6-羟基己基，5-羟基-3-氧杂戊基，苄基，1-苯乙基，2-苯乙基，2-甲酰氧基乙基，2-乙酰氧基乙基，2-丙酰氧基乙基，2-异丁酰氧基乙基，2-或3-甲酰氧基丙基，2-或3-乙酰氧基丙基，2-或3-丙酰氧基丙基，2-或3-异丁酰氧基丙基，2-或4-甲酰氧基丁基，2-或4-乙酰氧基丁基，2-或4-丙酰氧基丁基，2-或4-异丁酰氧基丁基，N-甲基-N-（2-羟乙基）-氨基甲酰基，2-甲氧基羰基乙基，2-乙氧基羰基乙基，2-苯氧基羰酰氧乙基，2-甲氨基碳酰氧基，2-乙氨基碳酰氧基乙基，2-异丙基氨基碳酰氧基乙基，2-苯基氨基碳酰氧基乙基，2-乙酰乙酰氧基乙基，烯丙基丙-1-烯-1-基，甲代烯丙基，乙代烯丙基，戊烯基，戊二烯基，己二烯基，3，7-二甲基辛-1，6-二烯-1-基，十一烷-10-烯-1-基，6，10-二甲基十一烷-5，9-二烯-2-基，3，7，11-三甲基十二烷-1，6，10-三烯-1-基，3，7，11-三甲基十二烷-2，6，10-三烯-1-基，十八-9-烯-1-基，十八-9，12-二烯-1-基，十八-9，12，15-三烯-1-基，6，10，14-三甲基十五-5，9，13-三烯-2-基，羟基，甲氧基，乙氧基，丙氧基，异丙氧基，丁氧基，异丁氧基，仲丁氧基，戊氧基，异戊氧基，新戊氧基，叔戊氧基，己氧基，庚氧基，辛氧基，异辛氧基，2-乙基己氧基，壬氧基，异壬氧基，癸氧基，异癸氧基，十一烷氧基，十二烷氧基，十三烷氧基，异十三烷氧基，十四烷氧基，十五烷氧基，十六烷氧基，十七烷氧基，十八烷氧基，氨基，一或二甲基氨基，一或二乙基氨基，一或二丙基氨基，一或二异丙基氨基，一或二丁基氨基，N-甲基-N-乙基氨基，一或二烯丙基氨基，苯基氨基或N-苯基-N-甲基氨基。
R1和R2还可以是例如，3，6-二噁庚基，3，6-二噁辛基，4，8-二噁壬基，3，7-二噁辛基，3，7-二噁壬基，4，7-二噁辛基，4，7-二噁壬基，4，8-二噁癸基，3，6，8-三噁癸基，3，6，9-三噁十一烷基，2-二甲基氨基乙基，2-二乙基氨基乙基，2-或3-二甲基氨基丙基，2-或3-二乙基氨基丙基，2-或4-二甲基氨基丙基，2-或4-二乙基氨基丁基，3，6-二甲基-3，6-二氮杂庚基，3，6，9-三甲基-3，6，9-三氮杂癸基，2-（1-甲氧基乙氧基）乙基，2-（1-乙氧基乙氧基）乙基，2-（1-异丁氧基乙氧基）乙基，2-或3-（1-甲氧基乙氧基）丙基，2-或3-（1-乙氧基乙氧基）丙基或2-或3-（1-异丁氧基乙氧基）丙基。
R1，R2，R5，和R6还可以是例如，苯基，2-，3-或4-甲基苯基，2-，3-或4-乙基苯基，2，4-二甲基苯基，2-，3-或4-甲氧基苯基，2-，3-或4-乙氧基苯基或2，4-二甲氧基苯基。
R3，R5，R6和R7还可以是例如甲酰氨基，乙酰氨基，丙酰氨基，丁酰氨基或异丁酰氨基。
R3，R4，R5，R6和R7还可以是例如乙烯基，氨磺酰，一或二甲基氨磺酰，一或二乙基氨磺酰，一或二丙基氨磺酰，一或二异丙基氨磺酰，一或二丁基氨磺酰，N-甲基-N-乙基氨磺酰，一或二烯丙基氨磺酰或苯基氨磺酰。
R3和R7还可以是例如羧基甲基，甲氧基羰基甲基，乙氧基羰基甲基，丙氧基羰基甲基，异丙氧基羰基甲基，丁氧基羰基甲基，烯丙氧基羰基甲基，苯氧基羰基甲基，巯基，甲硫基，乙硫基，丙硫基，异丙硫基或丁硫基。
R4，R5和R6还可以是例如羧基，甲氧基羰基，乙氧基羰基，丙氧基羰基，异丙氧基羰基，丁氧基羰基，烯丙氧基羰基，苯氧基羰基，烯丙硫基或苯硫基。
R5和R6还可以是例如甲基磺酰基，乙磺酰基，丙磺酰基，异丙磺酰基，丁磺酰基，苯磺酰基，甲酰基，乙酰基，丙酰基，丁酰基，异丁酰基或苯甲酰基。
R2和R3或R2和R7合在一起可以是例如1，3-亚丙基，1，1，3-三甲基-1，3-亚丙基，亚乙烯基，苯基亚乙烯基或式CH＝CH-CH2的基团。
式Ⅰ中优选的苯胺是其中的R1和R2各自分别为氢，未取代的或取代的并可被1至3个醚官能团中的氧原子或1至3个C1-C4烷基亚氨基所间断的C1-C15烷基，或烯丙基，未取代或取代的苯基，或R1和R2及与其相连的氮原子一起构成可含有其他杂原子的5元或6元饱和杂环基团，R3和R7各自分别是氢，C1-C4烷氧基，或与R2合在一起为未取代的或被1至3个甲基取代的1，3-亚丙基，
R4和R5分别为氢，R6是氢，C1-C4烷基，C1-C4烷氧基，C1-C4烷酰氨基或苯甲酰氨基，这些优选的苯胺被优选地用于标识矿物油。
式Ⅰ中R1和R2分别为氢，C1-C4烷基或R1和R2至少有一个基团为被羟基取代的和可以被1至3个醚官能团的氧原子或1至3个C1-C4烷基亚氨基间断的C2-C15烷基，R6是C1-C4烷基，特别是甲基的苯胺可特别优选地用于标记矿物油。
式Ⅰ中R3是氢，C1-C4烷基，C1-C4烷氧基和R6是氢，C1-C4烷基，C1-C4烷氧基，氨基或乙酰氨基的苯胺也可特别优选地用于标记矿物油。
式Ⅰ中R7是氢，C1-C4烷基或C1-C4烷氧基的苯胺也可特别优选地同于标识矿物油。
尤其是式Ⅰ中R1和R2两个基团中至少有一个基团是被羟基取代的C2-C4烷基，R6是甲基的苯胺用于标识矿物油。
式Ⅰ中R1和R2分别为被羟基取代的C2-C4烷基，特别是2-羟基乙基或2-或3-羟基丙基或R1是被羟基取代的C2-C4烷基，特别是2-羟基乙基或2-或3-羟基丙基和R2是C1-C4烷基的苯胺用于标识矿物油的应用是值得注意的。
2-甲氧基或2-乙氧基-5-乙酰氨基苯胺用于标识矿物油也是值得注意的。
本发明还涉及含有一种或多种式Ⅰ苯胺的矿物油。
就本发明来说，矿物油应被认为是指例如燃料，如汽油，煤油或柴油，油如燃料油或机油。
式Ⅰ的苯胺特别适用于标识那些需要识别的例如征税的原因需要识别的矿物油。为了使识别所需的成本降低，人们希望使用极少量的标识物。
为了标识矿物油，式Ⅰ的苯胺可以在没有溶剂的情况下或以溶液的形式使用。优选的溶剂是芳香烃如十二烷基苯，二异丙基萘或商业上可获得的名为Shellsol  AB（Shell公司出品）的高级芳香烃的混合物。为了避免得到的溶液产生高的粘度，通常选择苯胺Ⅰ的浓度为以溶液计的30%至50%（重量）。
借助于按本发明使用的式Ⅰ的苯胺，即使标识物质仅以约10ppm或更低的浓度存在，我们也可以用简单的方法检测标识的矿物油。
如果通过用含水介质处理矿物油萃取得到式Ⅰ的苯胺并在水相中在有或无缓冲液存在下使其与重氮盐偶合生成偶氮染料则我们就能有效地在矿物油中检测用作标识物的式Ⅰ的苯胺，上面所述的重氮盐是由选自氨基蒽醌，氨基萘，苯胺，氨基噻吩，氨基噻唑或氨基苯并异噻唑类的胺衍生得到。
如果通过用重氮盐的水溶液处理矿物油来萃取式Ⅰ的苯胺并然后在有或无缓冲液存在的条件下使其与重氮盐偶合生成偶氮染料，则我们就能特别有效地在矿物油中检测用作标识物的式Ⅰ的苯胺。
基于酸性含水溶液的适当的酸为例如无机酸或有机酸如盐酸，硫酸，硝酸，磷酸，甲酸，乙酸或丙酸。酸性水溶液通常具有的酸浓度为0.5至20%（重量）。
如果通过用含水介质处理矿物油来萃取式Ⅰ的苯胺并在水相中，在有或无缓冲液存在下使其与以在基质上的固体状态存在的重氮盐偶合生成偶氮染料，则我们就能特别有效地在矿物油中检测用作标识物的式Ⅰ的苯胺。
用于从矿物油中萃取式Ⅰ苯胺的适用的含水介质是例如水或水与酸和/或与水混溶的有机溶剂和/或无机物质的混合物。
适用的酸是上面所说浓度的上面所述的酸。
与水混溶的有机溶剂的实例是醇如甲醇，乙醇，丙醇，异丙醇，乙基乙二醇或1，2-丙二醇，醚如2-甲氧基乙醇，2-乙氧基乙醇，2-丁氧基乙醇，2-（2-甲氧基乙氧基）乙醇，1-甲氧基丙-2-醇或四氢呋喃，羧酰胺如N，N-二甲基甲酰胺或N-甲基吡咯烷酮，丙烯碳酸酯，二甲基亚砜或四氢噻吩砜。与水混溶的有机溶剂的用量以含水介质的重量计通常为1%至50%（重量）。
无机物质是例如，盐如碱金属卤化物，卤化铝或卤化锌或氨。
使用可以进一步含有可与水混溶的有机溶剂的酸的水溶液作为含水介质是优选的。
合适的基质是无机材料如活性碳，分子筛，硅藻土，二氧化钛，氧化铝或氯化钙，或有机材料如纤维素纤维，棉花，磨木，聚苯乙烯或聚氯乙烯。
在将存在于基质之上的重氮盐加入式Ⅰ苯胺的含水萃取液中之后，重氮盐完全溶解或部分溶解并由此为偶氮的偶合创造了条件。
为了获得最佳的偶合反应（该反应可以在溶剂存在下进行）以达到最高的偶氮染料的收率，应该使用缓冲物质控制PH值和使用优选摩尔比的反应物（苯胺∶重氮盐为1∶500至1∶1，更优选的为1∶100至1∶20）。
合适的缓冲物质的实例是碱金属乙酸盐，柠檬酸单碱金属盐，碱金属磷酸二氢盐，特别是上述各种盐的钠盐或如“化学和物理手册”，第65版，1984-1985，第D148页至150页中所述的缓冲体系。
现已证明使用重氮纸或重氮薄膜来检测式Ⅰ的苯胺是有效的。这些重氮指示剂是由下述方法制得的，即用相应的重氮盐溶液浸渍纸如过滤纸或浸渍涂覆了例如纤维素的薄层色谱薄膜，而使在显色过程中直接与含水萃取液接触的部分处于未处理状态。将用这种方法制得的纸条或薄膜条浸入含水萃取液中，就可以根据相似于纸色谱的方法最恰当地得到偶氮染料。在开始阶段生成的偶氮染料会一直保留下来并随着苯胺量的不断增加而被浓缩，因而也就易于检测。
特别值得注意的蒽醌类的胺是1-氨基蒽醌和4-氯-1-氨基蒽醌。
合适的氨基萘是例如式Ⅱ的氨基萘
其中Y1和Y2各自分别为氢，羟基或羟基磺酰基。
用于制得重氮盐的合适的苯胺为例如，式Ⅲ的苯胺
Figure 931212693_IMG5
（Ⅲ）
其中
X1是氢，卤素，C1-C4烷氧基，硝基或羟基磺酰基，
X2是氢，卤素，C1-C4烷氧基，氰基和硝基或是未取代的或被甲基，乙基，甲氧基或乙氧基取代的苯偶氮基，
X3是氢，C1-C4二烷基氨基，吡咯烷基（Pyrolidino），哌啶子基，吗啉代，硝基或羟基磺酰基，
X4是氢，卤素，氰基或杂环基团如3-苯基-1，2，4-噁二唑-5-基。
合适的氨基噻吩，氨基噻唑或氨基苯并异噻唑是例如具有下列通式的化合物
Figure 931212693_IMG6
适合用作重氮阳离子抗衡离子的合适的阴离子是常用的阴离子如氯离子，溴离子，硫酸氢根离子，硫酸根离子，磷酸二氢根离子，磷酸一氢根离子，磷酸根离子，四氟硼酸根离子，四氯锌酸根离子，萘-1，5-二磺酸根离子或乙酸根离子。
在某些情况下，加入少量芳基磺酸的碱金属盐如萘-1，5-二磺酸的钠盐用作重氮盐的稳定剂也是有利的。
优选的检测方法是使用由1-氨基蒽醌或由式Ⅲ中X1是氢，氯，或硝基，X2是氯或硝基和X3是氢的苯胺衍生的重氮盐进行检测的方法。更优选的是使用由1-氨基蒽醌衍生的重氮盐进行的检测方法。
通常，在检测反应中使用的是以重氮盐溶液的重量计的含有0.1%至2%（重量）重氮盐的重氮盐水溶液。对于每份重量的标识物油一般使用0.001%至0.1%（重量）的重氮盐溶液。
如上所述，还可以使用含水介质，特别是可以进一步含有可与水混溶的有机溶剂的含水酸从矿物油中萃取式Ⅰ的苯胺，和使其在基质上以固体状态存在并溶解在含水萃取液中的上述重氮盐偶合以生成偶氮染料。可与水混溶的有机溶剂能有利地使苯胺Ⅰ易于向水相转移。
在这种检测方法中，保持最佳的PH是特别重要的。使用缓冲物质可以有效地做到这一点。
特别适用的基质是纸条如过滤纸条。可以用上述重氮盐之一的溶液浸渍所说的纸条并干燥。（在干燥和避光的条件下贮存浸渍的纸条以避免重氮盐的分解）。
如果将这样的浸渍纸条浸入含水萃取液中，则由于偶氮染料的生成就会在其表面上发生显色反应。使用这种方法就可以极其简单的方法检测式Ⅰ的苯胺。
在特别优选的方法中，将几片浸渍过的纸条加入含水萃取液中，如果需要再进行简短的加热。
当然还可以在矿物油中使用普通的物理分析方法如气相色谱法，高压液相色谱法，薄层色谱法或柱色谱法来检测式Ⅰ的苯胺。
按照本发明的方法，作为矿物油标识物的式Ⅰ苯胺是染料生产中的普通产物。它们易于获得。
即使极少量的这类苯胺存在于矿物油中也能被检测到，在它们的检测过程中给出了强的显色反应。
下列实施例将进一步说明本发明。
实施例1
a）试剂溶液A，B和C的制备
试剂溶液A
将在硫酸中的1-氨基蒽醌的重氮盐的湿滤饼（固体含量：73%（重量））溶解在水中得到重量浓度为2.5%的溶液。该溶液的PH为约1.2。
试剂溶液B
通过2-（3-苯基-1，2，4-噁二唑-5-基）苯胺与亚硝酸钠的水重氮化反应得到0.063摩尔的氯化重氮盐溶液。该溶液的PH为约0.1。
试剂溶液C
通过2-氯-4-硝基苯胺与亚硝酸钠的水重氮化反应得到0.208摩尔氯化重氮盐溶液。该溶液的PH为约0。
b）在酸性溶液中的一般检测反应
将特定的苯胺以10ppm的浓度溶于柴油燃料中。将10毫升该溶液与0.1毫升上述的试剂溶液A充分摇动1分钟。然后将得到的混合物与3毫升9%（重量）盐酸一起再摇动1分钟。在各相稳定之后，可以发现下层水相将会显色。
为了进行光电测定，用蒸馏水将水相稀释至初始浓度的10%。
c）在缓冲水溶液中的一般检测反应
用1克9%（重量）的盐酸萃取10克用10ppm标识的柴油燃料，水相用氢氧化钠溶液中和，在每种情况下都加入4倍量的下述三种缓冲溶液1，2和3中的一种。
缓冲溶液1：5%（重量）的柠檬酸水溶液，用10%（重量）的氢氧化钠溶液调节至PH达到3.3。
缓冲溶液2：PH为4.4的5%（重量）的磷酸二氢钾水溶液。
缓冲溶液3：PH为8.2的5%（重量）的乙酸钠三水合物水溶液。
然后加入0.1克三种试剂溶液A，B或C中的一种。
偶合反应一般进行得非常迅速，但是在大多数情况下可以通过加热来加速偶合反应。
试验的结果列于下列的表中。颜色的强度是用等级1至5来评定的（1表示无颜色，5表示非常强的颜色）。表中还说明了显色反应是否为立刻发生。
d）试剂纸的制备
在超声浴中将5克在上面有关试剂溶液A制备方法中提到过的1-氨基蒽醌的重氮盐的滤饼溶解在95毫升蒸馏水中并用折纸漏斗过滤所得的溶液。将滤纸条浸入上述溶液中，除去过量的溶液，将湿纸条置于暗处以便干燥。当这些纸条放置在暗处时，即使在几周后也不会降低其反应活性，但是重氮纸变成了棕色。在50℃下放置8天后会发生相当明显的变色，但是这些变色的纸仍适用于显色试验。
e）使用试纸进行的检测
在试管中，将1克4%（重量）的盐酸加入用10ppm  N，N-[双（2-羟乙基）]-3-甲基苯胺（见实施例3）标识的10毫升燃料油中，用手剧烈摇动试管1分钟。在相完全分离后，取出下层水相用于下面的检测试验。
将0.55毫升33%（重量）的乙酸钠三水合物水溶液加入1克上面得到的水相中。该溶液的PH为4.5。将1滴这种溶液滴到重氮纸上，该重氮纸立即显示出红色。
可以将重氮纸条放入溶液中来替代将溶液逐滴加在重氮纸上。本发明中，将稀释的芳香胺溶液在重氮纸上流动并只在初始阶段将染料展开，因为此后染料不再移动。纸上的这一色斑将随着苯胺量的增加而不断变深，因而即使在稀释溶液中也能满意地检测苯胺。
这种浓缩效果对于在公路上进行检测仅为痕量的苯胺的试验特别有效。
另外，还可以将重氮纸片加入溶液中。由此使重氮盐发生溶解并且迅速使胺溶液变色。在某些情况下，需将溶液加热。
f）对比试验（空白试样）
为了对比，将10毫升未标识的柴油燃料和0.1毫升试验溶液A一起充分摇动1分钟，然后再与3毫升9%（重量）的盐酸一起剧烈摇动。在各相稳定后，根据不同的柴油燃料的级别，水相会或多或少地显出黄色。为了进行光电测定评估（见b）），将这种空白试样的实际上无色的溶液置于对照光束中，所说的溶液己稀释至初始浓度的10%。
检测反应也可以在缓冲溶液中进行。该方法相似于C）。
实施例2
a）将1-氨基蒽醌的硫酸氢重氮盐以1∶1的重量比与二氧化钛混合并在研钵中将其研制。
将生成的粉末与一定量的水混合以制得0.5%（重量）的重氮盐溶液。在过滤后，将溶液放入避光的容器中。
b）将1滴（0.05毫升）用软化的水再一次稀释至其浓度一半（1∶1）的上述a）的溶液加入到用10ppm  N-乙基-N-（2-羟乙基）-3-甲基苯胺标识的10毫升柴油燃料中。然后将混合物摇动1分钟。两相生成后，下层水相基本上呈蓝红色。
在使用含有未标识的柴油染料的空白试样的情况中，水相实际上完全无颜色。
因此，在柴油染料中即使有1ppm的浓度的标识物也可以检测到。
本发明的检测反应可以同于任何式Ⅰ的苯胺。用这种方法（如使用HPLC或光电测定法）还可以定量地检测式Ⅰ的苯胺。
Figure 931212693_IMG11
Figure 931212693_IMG12
Figure 931212693_IMG14
Figure 931212693_IMG15
Figure 931212693_IMG16
Figure 931212693_IMG18
Figure 931212693_IMG20
Figure 931212693_IMG21
Figure 931212693_IMG22
Figure 931212693_IMG24
Figure 931212693_IMG26
Figure 931212693_IMG27
Figure 931212693_IMG28
Figure 931212693_IMG29
Figure 931212693_IMG30
Figure 931212693_IMG31
Figure 931212693_IMG32
其他优选的重氮化合物为例如下列物质
Figure 931212693_IMG33
与下式用作标识物的苯胺发生偶合，并分别发生了蓝色显色反应。
Figure 931212693_IMG34

Claims (7)

1、式Ⅰ苯胺用于标识矿物油的应用
Figure 931212693_IMG2
其中R1和R2各自分别为氢，未取代的或取代的并可以被醚官能团中的1至3个氧原子或被1至3个C1-C4烷基亚氨基间断的C1-C18烷基，C3-C18链烯基或未取代的或取代的苯基，或者R1和R2连同与其相连的氮原子一起构成可以另外再含有杂原子的5元或6元的饱和杂环基，或者R1可以是式为OL1或NL1L2的基团，其中L1和L2各自分别为氢，未取代或取代的C1-C18烷基，C3-C18链烯基或者是未取代的或取代的苯基，R3和R7各自分别为氢，未取代的或取代的C1-C18烷基，C2-C18链烯基，氰基，硝基，甲酰基，未取代的或取代的C2-C4链烷酰基，甲酰氨基，未取代的或取代的C2-C4链烷酰氨基，苯甲酰氨基或式为OL1，CH2COOL1，NL1L2，SL1或SO2NL1L2的基团，其中L1和L2分别如上述定义，或与R2一起表示未取代的或被1至3个甲基取代的C2或C3亚烷基，未取代的或苯基取代的C2或C3亚烯基，R4是氢，未取代的或取代的C1-C18烷基，C2-C18链烯基，硝基或式为OL1，NL1L2，COOL1或SO2NL1L2的基团，其中L1和L2分别具有如上所述的含义，R5和R6各自分别为氢，未取代的或取代的C1-C18烷基，C2-C18链烯基，未取代的或取代的苯基，硝基，甲酰氨基，未取代的或取代的C2-C4烷酰氨基，苯甲酰氨基或式为OL1，NL1L2，SO2NL1L2，SO2NL1L2，SO2L3，COL1或COOL1的基团，其中L1和L2分别如上述定义，L3是未取代的或取代的C1-C18烷基，C3-C18链烯基或者是未取代的或取代的苯基，上述定义的先决条件是基团R3，R5或R7基团中至少有一个基团为氢。
2、根据权利要求1所述的苯胺的应用，其中R1和R2各自分别为氢，未取代的或取代的并可被1至3个醚官能团中的氧原子或被1至3个C1-C4烷基亚氧基间断的C1-C15烷基，烯丙基或未取代的或取代的苯基，或R1和R2连同与其相连的氮原子一起构成可含有其他杂原子的5元或6元的饱和杂环基，R3和R7各自分别为氢，C1-C4烷氧基或与R2一起为未取代的或被1至3个甲基取代的1，3-亚丙基，R4和R5分别为氢，R6为氢，C1-C4烷基，C1-C4烷氧基，C1-C4链烷酰氨基或苯甲酰氨基。
3、根据权利要求1所述的苯胺的应用，其中R1和R2分别为氢或C1-C4烷基或R1和R2中至少有一个基团为被羟基取代的并可被1至3个醚官能团中的氧原子或被1至3个C1-C4烷基亚氨基间断的C2-C15烷基，R6为C1-C4烷基。
4、含有一种或多种权利要求1中所述的式Ⅰ苯胺的矿物油。
5、一种检测矿物油中存在的权利要求1的式Ⅰ苯胺的方法，其中用含水介质处理矿物油以萃取式Ⅰ的苯胺，并在有或无缓冲液存在下，在水相中使其与重氮盐偶合以生成偶氮染料，所说的重氮盐是由选自氨基蒽醌，氨基萘，苯胺，氨基噻吩，氨基噻唑或氨基苯并噻唑类的胺衍生得到。
6、按照权利要求5所述的方法，其中使用重氮盐的酸性水溶液处理矿物油以萃取式Ⅰ的苯胺，并然后在有或无缓冲液存在下使其与重氮盐偶合以生成偶氮染料。
7、根据权利要求5所述的方法，其中使用含水介质处理矿物油以萃取式Ⅰ的苯胺并在水相中，在有或无缓冲液存在下，使其与以固体状态存在于基质上的重氮盐偶合以生成偶氮染料。
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PL177657B1 (pl) 1999-12-31
HU9501467D0 (en) 1995-07-28
TR28259A (tr) 1996-03-28
KR950704451A (ko) 1995-11-20
HU215462B (hu) 1999-01-28
HUT72016A (en) 1996-03-28
MX9307195A (es) 1994-07-29
CA2149747A1 (en) 1994-05-26
ZA938611B (en) 1995-05-18
CZ130795A3 (en) 1995-11-15
CN1045101C (zh) 1999-09-15
FI952423A0 (fi) 1995-05-18
WO1994011466A1 (de) 1994-05-26
ATE148734T1 (de) 1997-02-15
EP0669968B1 (de) 1997-02-05
PH31584A (en) 1998-11-03
EP0669968A1 (de) 1995-09-06
IL107592A0 (en) 1994-02-27
GR3023146T3 (en) 1997-07-30
US5627077A (en) 1997-05-06
KR100278235B1 (ko) 2001-03-02
AU676517B2 (en) 1997-03-13
ES2098117T3 (es) 1997-04-16
IL107592A (en) 1997-03-18
DE4238994A1 (de) 1994-05-26
DK0669968T3 (da) 1997-04-28
JPH08505647A (ja) 1996-06-18
DE59305417D1 (de) 1997-03-20
FI952423A (fi) 1995-05-18
AU5464794A (en) 1994-06-08
PL309043A1 (en) 1995-09-18

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