CN109988118A - 一种杂环偶氮化合物及其合成方法与应用 - Google Patents
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Abstract
本发明属于化合物合成领域，具体涉及一种杂环偶氮化合物及其合成方法与应用。杂环偶氮化合物结构式如式(Ⅰ)所示，式中，R1为H、C1‑C15烷基、C1‑C15烷氧基、苯基、C1‑C15烷基苯基或C1‑C15烷氧基苯基；R2为H、C1‑C15烷基、C1‑C15烷氧基、苯基、C1‑C15烷基苯基、C1‑C15烷氧基苯基、氰基、硝基或COOX；R3为H、C1‑C15烷基或C1‑C15烷氧基；R4为H或C1‑C15烷基；X为C1‑C15烷基。本发明获得的杂环偶氮染料作为新型杂环偶氮染料，其颜色鲜艳，色谱广并具有较高的发色强度，并且可作为新型标记化合物对油品进行染色标定。
Description
技术领域
本发明属于化合物合成领域，具体涉及一种杂环偶氮化合物及其合成方法与应用。
背景技术
三氮唑类偶氮染料是很重要的一类偶氮化合物，此类染料具有无致癌性、无毒性、颜色鲜艳和色谱广等优点，广泛用于染棉、羊毛、聚酰胺纤维。目前国内外偏重于苯系和萘系偶氮染料的研究工作，对于杂环类化合物研究工作很少，李德江等人发表文章及硕士论文以5-氨基-1H-1，2，4-三氮唑-3-羧酸为原料，与H酸、酚类和胺类化合物偶合，合成8种三氮唑类偶氮染料并对其结构进行了表征。但都未对此类染料的性能及用途作进一步的探讨。因此对此类化合物进行研究和开发并拓展其用途，具有一定的现实意义。
发明内容
本发明目的在于提供一种杂环偶氮化合物及其合成方法与应用。
为实现上述目的，本发明采用技术方案为：
一种杂环偶氮化合物，杂环偶氮化合物结构式如式(Ⅰ)所示：
式中，R1为H、C1-C15烷基、C1-C15烷氧基、苯基、C1-C15烷基苯基或C1-C15烷氧基苯基；
R2为H、C1-C15烷基、C1-C15烷氧基、苯基、C1-C15烷基苯基、C1-C15烷氧基苯基、氰基、硝基或COOX；
R3为H、C1-C15烷基或C1-C15烷氧基；
R4为H或C1-C15烷基；
X为C1-C15烷基。
优选，所述化合物为通式(Ia)所示：
式中,R1为H或C1-C3烷基；
X为C1-C3烷基；
R3为H、C1-C3烷基或C1-C3烷氧基；
R4为H或C1-C7烷基。
更优选，所述化合物为通式(Ib)所示
式中：R5、R6可相同或不同的为H、C1-C3烷基或C1-C3烷氧基；
R3为H，C1-C3烷基或C1-C3烷氧基；
R4为H或C1-C7烷基。
一种杂环偶氮化合物的合成方法，以5-氨基-1H-1，2，4-三氮唑衍生物为原料，原料经重氮化，而后与乙酰胺类化合物偶合为单偶氮化合物，所得单偶氮化合物再经重氮化，重氮化后与酚类化合物偶合得式(Ⅰ)所示杂环偶氮化合物。
进一步，
1)5-氨基-1H-1，2，4-三氮唑衍生物，亚硝酸钠，乙酰胺类化合物和水加入反应器中，在搅拌及氮气保护下滴加酸进行反应，然后升温至80-90℃保持2～3小时，制得单偶氮化合物；其中，5-氨基-1H-1，2，4-三氮唑衍生物：亚硝酸钠：乙酰胺类化合物摩尔比为1:(1～1.1):(1～1.3)；
2)上述单偶氮化合物经重氮化反应，将酚类化合物溶于有机溶剂中搅拌混匀后滴入上述获得重氮液中进行偶合反应，制得杂环偶氮化合物
所述步骤1)中滴加的酸为盐酸、硫酸、醋酸、磷酸或碳酸；所述步骤2)中有机溶剂为醇类或烷烃类化合物。
一种杂环偶氮化合物的应用，所述杂环偶氮化合物作为标记化合物在对油品进行染色标定中的应用。
本发明所具有的优点：
本发明所得杂环偶氮化合物可作为新型标记化合物对油品进行染色标记，同时还可用于染棉、羊毛或聚酰胺纤维染色。油品标记物是一种添加到油品中、用于检测识别石油产品的化合物，实施燃油税分类征收以及燃油分类精细化管理。本发明合成的杂环偶氮化合物为双偶氮杂环染料，其结构特点为一重氮组份为三氮唑杂环，其余为苯环和萘环。与苯及萘环类双偶氮染料相比，该类染料颜色鲜艳，色谱广，有相对较高的摩尔消光系数。体现为作油品标记物时具有较高发色强度，以ppm级浓度溶于油品中仍可以肉眼识别，在极低浓度下能有效检测，从而不影响油品性能。
具体实施方式
下面结合实施例对本发明作进一步的解释说明。
实施例1：
(1)将5-氨基-1H-1，2，4-三氮唑43克(98％，0.5mol)，亚硝酸钠36克(99％,0.51mol)，2，5-二甲基乙酰苯胺84克(99％,0.51mol)溶于600克水中，在氮气保护下于0℃滴加20％盐酸110克，滴加完毕，升温至85℃反应两个小时，加入氯化钠盐析，过滤得单偶氮中间产物。
(2)将上述单偶氮中间产物溶于500克水、200克20％盐酸中，搅拌下于0℃滴加30％亚硝酸钠水溶液，将重氮化反应液点于碘化钾淀粉试纸中，试纸变蓝，搅拌三分钟蓝色不消失即为反应终点。将2-萘酚74克(99％，0.51mol)，碳酸氢钠40克,50克甲苯加入反应器中，搅拌下于5℃缓缓滴入上述重氮液，滴加完毕于此温度下搅拌至反应终点，除去水并将溶剂蒸发，得下述结构式所示化合物1。该化合物1溶于乙醇，二甲苯中呈橙红色，λmax＝490nm
化合物1的1H-NMR(400Hz,DMSO-d6)数值为：δ＝2.41,2.44(s，CH3)；δ＝7.1(s，N-CH＝N)；δ＝7.26,7.87(s，C6H6)；δ＝6.91～8.57(m,C10H8)；δ＝16.42(s,OH).
实施例2.
(1)将5-氨基-1H-1，2，4-三氮唑-3-甲酸甲酯72克(98％，0.5mol)，亚硝酸钠36克(99％,0.51mol)，2，5-二甲基乙酰苯胺84克(99％,0.51mol)溶于600克水中，在氮气保护下于0℃滴加20％盐酸110克，滴加完毕，升温至85℃反应两个小时，加入氯化钠盐析，过滤得单偶氮中间产物。
(2)将上述单偶氮中间产物溶于500克水，200克20％盐酸中，搅拌下于5℃滴加30％亚硝酸钠水溶液，将重氮化反应液点于碘化钾淀粉试纸，试纸变蓝，搅拌三分钟蓝色不消失即为反应终点。将2-萘酚74克(99％，0.51mol)，碳酸氢钠40克,50克乙醇加入反应器中，搅拌下于10℃以下缓缓滴入上述重氮液，滴加完毕于此温度下搅拌至反应终点，除去水并将溶剂蒸发，得下述结构式所示化合物2。该化合物溶于乙醇中呈蓝光红色。λmax＝515nm
化合物2的1H-NMR(400Hz,DMSO-d6)数值为：δ＝2.51,2.76(s,CH3)；δ＝3.80(s,COOCH3)；δ＝7.58,8.04(s,C6H6)；δ＝6.87～8.60(m,C10H8)；δ＝16.54(s,OH).
实施例3-8
实施例3-8所得化合物的核磁数据如下：
应用例
将上述实施例2的样品以1000ppm浓度溶解在乙醇中，稀释至10ppm,得蓝光红色溶液，以分光光度法测得λmax＝515nm，计算摩尔消光系数＝3.58×104L/mol.cm。将上述实施例2样品以10ppm的浓度溶于石油烃中放入玻璃瓶中进行稳定性实验，于室外常温下放置三个月后，以分光光度法测石油烃溶液吸收值，石油烃溶液吸收值无变化，并无结晶物质存在，稳定性良好。以同样的方法检测实施例4,6的样品,并与现有油品标记商品染料溶剂红23,溶剂红24对比,数据如下:
溶剂红23和溶剂红24是目前多个国家使用的油品标记染料。从上表可看出，实施例4和实施例6化合物的摩尔消光系数要高于溶剂红23和溶剂红24，具有更高的发色性能。这种性能在用于油品标记中，体现为以ppm级浓度溶于石油烃中颜色更深，更易于肉眼识别，在标记相同颜色深度下，使用更少的染料，石油体系的稳定性更好。因此可作为油品标记化合物应用。
Claims (7)
1.一种杂环偶氮化合物，其特征在于：杂环偶氮化合物结构式如式(Ⅰ)所示：
式中，R1为H、C1-C15烷基、C1-C15烷氧基、苯基、C1-C15烷基苯基或C1-C15烷氧基苯基；
R2为H、C1-C15烷基、C1-C15烷氧基、苯基、C1-C15烷基苯基、C1-C15烷氧基苯基、氰基、硝基或COOX；
R3为H、C1-C15烷基或C1-C15烷氧基；
R4为H或C1-C15烷基；
X为C1-C15烷基。
2.按权利要求1的杂环偶氮化合物，其特征在于：所述化合物为通式(Ia)所示：
式中,R1为H或C1-C3烷基；
X为C1-C3烷基；
R3为H、C1-C3烷基或C1-C3烷氧基；
R4为H或C1-C7烷基。
3.按权利要求1的杂环偶氮化合物，其特征在于：所述化合物为通式(Ib)所示
式中：R5、R6可相同或不同的为H、C1-C3烷基或C1-C3烷氧基；
R3为H，C1-C3烷基或C1-C3烷氧基；
R4为H或C1-C7烷基。
4.一种权利要求1的杂环偶氮化合物的合成方法，其特征在于：以5-氨基-1H-1，2，4-三氮唑衍生物为原料，原料经重氮化，而后与乙酰胺类化合物偶合为单偶氮化合物，所得单偶氮化合物再经重氮化，重氮化后与酚类化合物偶合得式(Ⅰ)所示杂环偶氮化合物。
5.按权利要求4的杂环偶氮化合物的合成方法，其特征在于：
1)5-氨基-1H-1，2，4-三氮唑衍生物，亚硝酸钠，乙酰胺类化合物和水加入反应器中，在搅拌及氮气保护下滴加酸进行反应，然后升温至80-90℃保持2～3小时，制得单偶氮化合物；其中，5-氨基-1H-1，2，4-三氮唑衍生物：亚硝酸钠：乙酰胺类化合物摩尔比为1:(1～1.1):(1～1.3)；
2)上述单偶氮化合物经重氮化反应，将酚类化合物溶于有机溶剂中搅拌混匀后滴入上述获得重氮液中进行偶合反应，制得杂环偶氮化合物。
6.按权利要求5的杂环偶氮化合物的合成方法，其特征在于：
所述步骤1)中滴加的酸为盐酸、硫酸、醋酸、磷酸或碳酸；
所述步骤2)中有机溶剂为醇类或烷烃类化合物。
7.一种权利要求1所述的杂环偶氮化合物的应用，其特征在于：
所述杂环偶氮化合物作为标记化合物在对油品进行染色标定中的应用。
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US3133910A (en) * | 1960-05-20 | 1964-05-19 | Basf Ag | Tetrazapolymethine dyes |
| CN102863821A (zh) * | 2012-10-17 | 2013-01-09 | 江苏之江化工有限公司 | 一种分散型偶氮染料混合物 |
| CN106699930A (zh) * | 2016-12-01 | 2017-05-24 | 沈阳化工研究院有限公司 | 一种油品标记聚合物及制备方法和应用 |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133910A (en) * | 1960-05-20 | 1964-05-19 | Basf Ag | Tetrazapolymethine dyes |
| CN102863821A (zh) * | 2012-10-17 | 2013-01-09 | 江苏之江化工有限公司 | 一种分散型偶氮染料混合物 |
| CN106699930A (zh) * | 2016-12-01 | 2017-05-24 | 沈阳化工研究院有限公司 | 一种油品标记聚合物及制备方法和应用 |
Non-Patent Citations (2)
| Title |
|---|
| 智双等: "油品标记物的研究现状", 《染料与染色》 * |
| 李德江等: "两种新型杂环偶氮染料的合成研究", 《精细化工中间体》 * |
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