CN1054878C - 偶氮染料在标定烃类方面的应用及新的偶氮染料 - Google Patents

偶氮染料在标定烃类方面的应用及新的偶氮染料 Download PDF

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CN1054878C
CN1054878C CN94194631A CN94194631A CN1054878C CN 1054878 C CN1054878 C CN 1054878C CN 94194631 A CN94194631 A CN 94194631A CN 94194631 A CN94194631 A CN 94194631A CN 1054878 C CN1054878 C CN 1054878C
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G·赛德勒
G·索尔茨
C·克拉
K·H·贝克
U·迈耶
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Abstract

通式Ⅰ偶氮染料作为烃类的与pH-值相关的标定剂之应用，式中A环可以是苯并稠合的，n为0或1，R1为氢或任选的被取代了的C1-C15-烷基，R2为任选的被取代了的C1-C15-烷基，R3、R4、R5、R6和R7分别为氢、C1-C15-烷基或C1-C15-烷氧基和R8为氢、C1-C15-烷基、C1-C15-烷氧基、氰基、硝基或一个羧基，该羧基在必要时被酯化，含有上述偶氮染料的烃类，证明这类偶氮染料在烃类中的方法以及新的偶氮染料。

Description

偶氮染料在标定烃类方面的应用及新的偶氮染料
本发明涉及通式I的偶氮染料作为烃类的pH-值相关标定剂的应用，含有上述偶氮染料的烃类，用于证明烃类中该种偶氮染料的方法以及新的偶氮染料。
Figure C9419463100051
式中
A环可以是苯并稠合的，
n为0或1，
R1为氢或C1-C15-烷基，该烷基可以被醚官能中的1至4个氧原子中断，
R2为C1-C15-烷基，该烷基可以被醚官能中的1至4个氧原子中断，或者为一个通式L-NX1X2基团，其中L是C2-C8-亚烷基，X1和X2为互相独立的分别为C1-C6-烷基或者与连接它们的氮原子一起形成一个5元或6元的饱和的杂环基，在环中还可以包含一个氧原子，
R3、R4、R5、R6、和R7互为独立的分别是氢、C1-C15-烷基或C1-C15-烷氧基和
R8为氢、C1-C15-烷基、C1-C15-烷氧基、氰基、硝基或一个通式为COOX3的基团，其中X3为氢、C1-C15-烷基，该烷基可以被醚官能中的1-4个氧原子中断，或为一个通式L-NX1X2基，其中L、X1和X2分别具有上述的含义。
从文献US-A 5 145 573、US-A 5 182 372以及EP-A-499 845中已经得知偶氮染料作为矿物油的标定剂。然而文献指出，文中描述的染料在烃类中稀释性不够理想。
在文献US-A-4 009 008中，进一步描述了一种借助偶氮染料标定矿物油的方法，在该法中使得加入矿物油中的染料成为可见的，方法是向标定的矿物油中加入一种吸附剂，该吸附剂与矿物油的其它有色成分相结合。
本发明的目的是提供烃类的新型标定剂。新的标定剂应该容易取得并在烃类中很好溶解。另外，它们能用简单方法检验。在此，还应该用非常少量的标定材料，通过一个强的颜色反应使之变为可见的。
依此，发现开头定义的通式I偶氮染料特别适合作为与pH-值相关的烃类标定剂，从而实现了本发明的目的。
所有的在此提到的通式中出现的烷基和亚烷基可以是直链的也可以是带支链的。
如果X1和X2与连接它们的氮原子一起形成一个5元或6元的饱和的杂环基，在环中还可以含有一个氧原子的话，为此可以考虑以下基团：例如吡咯烷基、哌啶基或吗啉基。
R1、R2、R3、R4、R5、R6、R7、R8、X1、X2和X3，例如是甲基、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、己基或2-甲基戊基。
R1、R2、R3、R4、R5、R6、R7、R8和X3基进一步是，例如：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、十四烷基或十五烷基(上面名称的异辛基、异壬基、异癸基和异十三烷基是普通名称并且来源于根据羰基合成得到的醇类，参考文献：Ullmann’s Encyclopedia of Industrial Chemistry，5 th Edition，Vol.A1，Seiten 290-293，以及Vol.A10，Seiten284和285)。
R3、R4、R5、R6、R7和R8进一步是，例如：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、2-甲基戊氧基、庚氧基、辛氧基、2-乙基己氧基、异辛氧基、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、3，5，5，7-四甲基壬氧基、异十三烷氧基、十四烷氧基或十五烷氧基。
L基是，例如：(CH2)2，(CH2)3，(CH2)4，(CH2)5，(CH2)6，(CH2)7，(CH2)8，CH(CH3)CH2 oder CH(CH3)CH(CH3)，
R1、R2和X3基进一步是，例如：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、3，6-二氧杂庚基、3，6-二氧杂辛基、4，8-二氧杂壬基、3，7-二氧杂辛基、3，7-二氧杂壬基、4，7-二氧杂辛基、4，7-二氧杂壬基、2-或4-丁氧基丁基、4，8-二氧杂癸基、4，7-二氧杂十一烷基、3，6，9-三氧杂癸基、3，6，9-三氧杂十一烷基、3，6，9-三氧杂十二烷基、4，7，10-三氧杂十一烷基、3，6，9，12-四氧杂十三烷基或3，6，9，12-四氧杂十四烷基。
优选将通式Ia偶氮染料用于烃类标定，
Figure C9419463100081
式中
R1为氢或C1-C15-烷基，和
R2和R3互为独立的分别为C1-C15-烷基，
R7和R8分别具有上述的含义。
更优选将通式Ib偶氮染料用于烃类标定，式中
R1为氢或C1-C15-烷基，和
R2为C1-C15-烷基，
X3具有上述含义。
更优选将通式Ic偶氮染料用于烃类标定，式中
R2为C1-C15-烷基和
R5、R6、R7、和R8分别具有上述的含义。
特别优选将通式Ia偶氮染料用于烃类标定，式中R1和R2互为独立的分别代表C1-C13-烷基、R3代表甲基、R7代表氢和R8代表一个通式COOX3基，其中X3为C1-C13-烷基。
特别优选将通式Ic偶氮染料进一步用于烃类标定，式中
R2为C1-C13-烷基，
R5和R7分别为甲基和
R6和R8分别为氢。
一些通式I的染料是已知的，例如在文献GB-A-953 719、US-A-3 218 309或US-A-4 037 007中有描述。
作为pH-值相关的标定剂，根据本发明的意图对于通式I偶氮染料可以这样理解，即该染料在一种质子酸的作用下，在一种金属卤化物存在或不存在下(如锌、铝或锡的卤化物)，产生一种颜色反应，即变色，伴随出现颜色变深。
根据本发明意图的标定可以理解为通式I的偶氢染料以一定浓度加入到烃类中，通过加入该染料使烃类的颜色变化用肉眼几乎看不出或者稍许可见，然而通式I染料在这里通过本文详细描述的检验方法很容易被检测，并且清楚可见。
本发明还涉及含有一种或多种通式I偶氮染料的烃类。
根据本发明的意图对于烃类可以理解为脂肪族或芳香族烃类，它们在标准温度和压力条件下为液态，尤其是矿物油，例如发动机燃料，如汽油、煤油或柴油、或者油类，如燃料油或马达油。
通式I偶氮染料尤其适用于矿物油的标定，在矿物油中要求一种标记，例如出于控制的原因。为了使标记的费用尽量减少，力争用尽可能少量的标定剂进行标定。
通式I偶氮染料可以用本体材料或者以溶液形式进行烃类标定。作为溶剂用有机溶剂适宜。最好用芳香烃，如甲苯、二甲苯、十二烷基苯、二异丙基萘或高级芳香物质的混合物，商业上通常名为ShellsolAB(Fa.Shell)。为了避免得到的溶液粘度太高，通常选择偶氮染料I的浓度在20-80％重量，按溶液计算。
为了改善溶解性也可以使用其它的共溶剂，例如醇类，如：甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇、戊醇、己醇、庚醇、辛醇、2-乙基己醇或环己醇，甘醇，如：丁基乙二醇或甲基丙二醇，胺类，如：三乙胺、二异辛基胺、二环乙胺、苯胺、N-甲基苯胺、N，N-二甲基苯胺、甲苯胺或二甲苯胺，链烷醇胺，如：3-(2-甲氧乙氧)丙胺，邻甲酚、间甲酚，对甲酚，酮类，如：二乙酮或环己酮，内酰胺，如：r-丁基内酰胺，碳酸酯，如：碳酸亚乙酯或碳酸亚丙酯，酚类，如：叔丁基苯酚或壬基苯酚，酯类，如：邻苯二甲酸甲酯、邻苯二甲酸乙酯、邻苯二甲酸(2-乙基己)酯、醋酸乙酯、醋酸丁酯或醋酸环己酯，酰胺类，如：N，N-二甲基甲酰胺、N，N-二乙基乙酰胺或N-甲基吡咯烷酮，或者它们的混合物。
借助于本发明所使用的通式I偶氮染料，可以非常简单的检验标定的烃类，甚至标定物质的浓度只有大约10ppm或更少。
在有些情况下，使用通式I染料的混合物作为标定材料更为有利。
作为标定材料使用的通式I偶氮染料在烃类中存在的检测，最好用一种水-醇介质或醇介质处理烃类，所述介质含有一种质子酸，如需要的话，还含有一种金属锌-，铝-或锡的卤化物。在使用水-醇介质时，水与醇重量比为0.5∶1至4∶1，最好为大约1∶1。
在加入质子酸，及需要的话，加入金属卤化物到标定的烃类中时，导致一个明显的可见的颜色反应，并且在使用水-醇介质时偶氮染料I过渡到水-醇相里。
适宜的醇有，例如乙醇、丙醇、异丙醇、1-甲氧基丙-2-醇、乙二醇或1，2-或1，3-丙二醇。使用乙醇为最好。
适宜于本发明所述新方法的质子酸具体为强酸，即它的pKa-值≤3.5的质子酸。作为这类酸可以考虑的有无机酸或有机酸，如：高氯酸、氢碘酸、盐酸、氢溴酸、氢氟酸、硫酸、硝酸、磷酸、苯磺酸、甲苯磺酸、萘磺酸、甲磺酸、草酸、马来酸、氯乙酸、二氯乙酸和溴乙酸。在有些情况下，例如通过加醋酸对这些酸进行缓冲是有利的。
除了邻-或对-甲苯磺酸外，无机酸是特别突出的，其中盐酸或硫酸特别重要。
适宜的锌、铝或锡的金属卤化物是，例如氯化锌、溴化锌、氯化铝、溴化铝或四氯化锡。特别突出的是氯化锌。
通常大约10至50ml本发明所述的标定的烃类与10至50ml一种质子酸的水-醇或醇溶液并任选地加入金属卤化物进行摇动就足以获得颜色反应。也可以单独使用一种金属卤化物的水-醇溶液，因为该溶液同样呈酸性反应。
质子酸在水-醇或醇溶液中浓度通常为5至50％重量，优选的为10至30％重量。金属卤化物的浓度一般在0至50％重量，优选的在5至20％重量，分别以溶液的重量计算。
本发明还涉及通式II偶氮染料，式中
n为0或1，其中当n为0时，
Z1为C1-C15-烷基，它可以被在醚官能中的1至4个氧原子中断，或为一个通式L-NX1X2的基，式中L为C2-C8-亚烷基和X1与X2互为独立的分别为C1-C5-烷基或与连接它们的氮原子一起形成一个5-或6元的饱和杂环基，在环中还可以包含一个氧原子。
R7为氢、C1-C15-烷基或C1-C15-烷氧基，
Z2为一个通式COOZ3的基，其中Z3为C1-C15-烷基，该烷基可以被在醚官能中的1至4个氧原子中断，或为一个通式L-NX1X2的基，其中L、X1和X2分别具有上述含义，
附带指出，如果Z1为L-NX1X2基，在X1、X2和Z3基中存在的碳原子总数至少为8个，或者当n为1时，
Z1为通式L-NX1X2基，式中L、X1和X2各自具有上述含义，和
R5、R6、R7和Z2各自为氢、C1-C15-烷基或C1-C15-烷氧基，
前提条件是，在R5/R6和R7/Z2基对中分别有一个基团不是氢。
本发明还涉及通式III偶氮染料，式中
Q1为氢或C1-C15-烷基，
Q2为C1-C15-烷基，
Q3为C1-C15-烷基或C1-C15-烷氧基，
Q4为氢、C1-C15-烷基或C1-C15-烷氧基和
Q5为C1-C15-烷基，它可以被在醚官能中的1至4个氧原子中断，或为一个通式L-NX1X2的基，式中L为C2-C8-亚烷基和X1与X2互为独立的为C1-C6-烷基或与连接它们的氮原子一起组成一个5元或6元的饱和的杂环基，在环中还可以含有一个氧原子，
前提条件是，在Q1、Q2和Q5基中存在的碳原子总数至少为8个。
优选的通式II偶氮染料中的n为0。
特别优选的通式II偶氮染料是式中的n为0，Z1为C1-C13-烷基，R7为氢和Z2为COOZ3基，其中Z3具有上述的含义。
优选的另一个通式III偶氮染料是式中的Q1Q2和Q3互相独立地为C1-C15-烷基且Q4是氢。
特别优选的另一个通式III偶氮染料是式中的Q1和Q2互相独立地是C1-C13-烷基，Q3是甲基，Q4是氢和Q5是C1-C13-烷基。
通式II和III的新的染料可以根据本来已知的方法获得。
通式II染料的制备，例如可以将通式IVa或IVb的一种胺用已知的方法进行重氮化，并将产物与一个通式V的偶合组分进行偶合，式中的R5、R6、R7和Z2、Z1都具有上述的含义。
Figure C9419463100141
通式IVb胺的制取又可以通过通式IVa胺的重氮化和紧接着将产物用一种通式IVc苯胺进行偶合来得到，式中R5和R6分别具有上述含义。
通式III染料的制备，例如可以对通式IV胺用已知的方法进行重氮化，并用一个通式VII的偶合组分进行偶合，式中的Q4和Q5、Q1、Q2和Q3分别具有上述含义。
Figure C9419463100152
通式II和III的新的偶氮染料在有机溶剂中具有一个好的溶解性，并且如上面陈述的以优选的方式作为烃类的pH-值相关的标定剂。
本发明将通过下列实施例进行详细阐述。A，制备实施例1
将107g 4-(3′甲基苯基偶氮)-3-甲基苯胺盐酸盐和0.5g一种阴离子表面活性剂在一种由50ml水和30ml 5N的盐酸组成的混合物中，于室温进行悬浮。加入50g冰和20ml甲苯之后，与6.9g亚硝酸钠的浓水溶液进行反应。重氮化于5-10℃经过2小时结束，其中过量的亚硝酸盐用氨基磺酸除去。随后，为溶解重氮盐，于10-15℃滴加一种溶液，它由29.5g 1-(3-二乙基氨基丙基)氨基萘和35ml甲苯组成。随后，反应混合物的pH-值用2.5N醋酸钠溶液提高到大约4，偶合反应在30分钟之后结束。用10N苛性钠溶液把pH-值升高到大约8之后，产生一个相分离。有机相将于60℃通过多次用水萃取，洗到无盐为止。把甲苯蒸掉以后，得到50g油状的以下通式的染料，它在芳香物质中溶解好，呈红色，入max(甲苯)：522nm。
Figure C9419463100161
实施例2
于5-10℃将35.2g 58％重量的邻氨基苯甲酸(2-二甲基氨基乙)酯水溶液滴加到由33ml 10N盐酸和10ml冰醋酸组成的混合物中。随后，于10-15℃与6.9g亚硝酸钠浓水溶液进行反应，在此pH-值保持在0.5以下，重氮化反应于10-15℃经过30分钟结束，其中过剩的亚硝酸盐用氨基磺酸除掉。加入1g一种阴离子表面活性剂以后，于10-15℃，在30分钟内，向重氮盐溶液中滴加26.2g 1-(2-乙基己基氨基)萘，它事先溶在30ml冰醋酸中。随后，沉积物用100ml水冲稀，偶合反应在2小时之后结束。加入100ml甲苯之后，把pH-值用10N苛性钠溶液提高到大约7时产生一个相分离。有机相然后在60℃通过多次用水萃取，洗至无盐为止。蒸掉甲苯之后，得到48g具有以下通式的油状染料，
Figure C9419463100171
它在芳香物质中溶解好，呈橙色，入max(甲苯)：448nm。B)应用
一般方法
在商业通用的柴油中加入一种40％重量的标定材料在一种商业通用的高芳香物质混合物中的溶液-ShellsolA B(Fa.Shell)。
标定剂的附加量为10ppm。
a)50ml标定的柴油在分液漏斗中，用50ml-种酸性试剂，其组成为45g水、45g乙醇、5g对甲苯磺酸和5g氯化锌，进行反应。混合物被强烈振动大约10秒钟。之后产生相分离，检测溶液相的颜色变深。水相可以对已知浓度的溶液用光度法进行测量。
b)20ml标定的柴油用20ml试剂溶液(10％重量的氯化锌溶在水/乙醇混合物中(60∶40V/V)，pH-值通过加入85％重量的醋酸调节到2)强烈的振动。其中下层水相明显的变色。水相可以对应一种已知浓度的溶液用光度法进行测量。
在下列表中列出的染料按方法a进行测试。它们也可以按方法b进行测试，具有同样好的结果。
在下列表中，用*)标出的入max-值表示测试是分别在甲苯中进行，用**)标出的入max-值表示测试是分别在水∶乙醇∶对甲苯磺酸∶氯化锌＝45∶45∶5∶5(重量比)混合物中进行。
                          表1
Figure C9419463100181
                        表2
                         表3
Figure C9419463100192
                         表4
Figure C9419463100201
                          表5

Claims (4)

1.通式I偶氮染料作为烃类的与pH-值相关的标定剂之应用，
Figure C9419463100021
式中
A环可以是苯并稠合的；
n为0或1，
R1为氢或C1-C15-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、3，6-二氧杂庚基、3，6-二氧杂辛基、4，8-二氧杂壬基、3，7-二氧杂辛基、3，7-二氧杂壬基、4，7-二氧杂辛基、4，7-二氧杂壬基、2-或4-丁氧基丁基、4，8-二氧杂癸基、4，7-二氧杂十一烷基、3，6，9-三氧杂癸基、3，6，9-三氧杂十一烷基、3，6，9-三氧杂十二烷基、4，7，10-三氧杂十一烷基、3，6，9，12-四氧杂十三烷基或3，6，9，12-四氧杂十四烷基；
R2为C1-C15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、3，6-二氧杂庚基、3，6-二氧杂辛基、4，8-二氧杂壬基、3，7-二氧杂辛基、3，7-二氧杂壬基、4，7-二氧杂辛基、4，7-二氧杂壬基、2-或4-丁氧基丁基、4，8-二氧杂癸基、4，7-二氧杂十一烷基、3，6，9-三氧杂癸基、3，6，9-三氧杂十一烷基、3，6，9-三氧杂十二烷基、4，7，10-三氧杂十一烷基、3，6，9，12-四氧杂十三烷基或3，6，9，12-四氧杂十四烷基；或为一个通式L-NX1X2基，其中L是C2-C8亚烷基及X1和X2互相独立为C1-C6-烷基或者与连接它们的氮原子一起形成一个5元或6元的饱和的杂环基，在环中还可以包含一个氧原子，
R3、R4、R5、R6和R7互为独立的分别是氢、C1-C15烷基或C1-C15-烷氧基和
R8为氢、C1-C15-烷基、C1-C15-烷氧基、氰基、硝基或一个通式COOX3的基，其中X3为氢、C1-C15-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、3，6-二氧杂庚基、3，6-二氧杂辛基、4，8-二氧杂壬基、3，7-二氧杂辛基、3，7-二氧杂壬基、4，7-二氧杂辛基、4，7-二氧杂壬基、2-或4-丁氧基丁基、4，8-二氧杂癸基、4，7-二氧杂十一烷基、3，6，9-三氧杂癸基、3，6，9-三氧杂十一烷基、3，6，9-三氧杂十二烷基、4，7，10-三氧杂十一烷基、3，6，9，12-四氧杂十三烷基或3，6，9，12-四氧杂十四烷基；或为一个通式L-NX1X2基，其中L、X1和X2分别具有上述的含义。
2.根据权利要求1的偶氮染料之应用，该偶氮染料具有通式Ia，式中
R1为氢或C1-C15-烷基，和
R2和R3互为独立的分别为C1-C15-烷基和
R7和R8分别具有在权利要求1中所述的含义。
3.根据权利要求1的偶氮染料之应用，该偶氮染料具有通式Ib，
Figure C9419463100041
式中，
R1为氢或C1-C16-烷基和
R2为C1-C15-烷基和
X3具有在权利要求1中所述的含义。
4.根据权利要求1的偶氮染料之应用，该偶氮染料具有通式Ic，式中
R2为C1-C15-烷基和
R5、R6、R7和R8分别具有在权利要求1中所述的含义。
CN94194631A 1993-12-22 1994-12-09 偶氮染料在标定烃类方面的应用及新的偶氮染料 Expired - Fee Related CN1054878C (zh)

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