CN105503561B - 一种酸碱指示剂及其合成方法与应用 - Google Patents

一种酸碱指示剂及其合成方法与应用 Download PDF

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CN105503561B
CN105503561B CN201510980119.4A CN201510980119A CN105503561B CN 105503561 B CN105503561 B CN 105503561B CN 201510980119 A CN201510980119 A CN 201510980119A CN 105503561 B CN105503561 B CN 105503561B
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王石发
杨金来
徐徐
杨益琴
杨丽娟
王忠龙
芮坚
曹晓琴
丁志斌
王芸芸
张齐
孙楠
张燕
匡洪波
刘艳芳
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Nanjing Forestry University
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Abstract

本发明公开了一种酸碱指示剂，在酸性环境中显示无色，在碱性环境中示橙黄色，该酸碱指示剂为3‑(2′‑羟基亚苄基)诺蒎酮。本发明提供的酸碱指示剂为新型蒎烷基指示剂3‑(2′‑羟基亚苄基)诺蒎酮，具有遇碱由无色变成橙黄色的指示剂性能，显色范围为pH≥8.4。该指示剂，易溶于甲醇、乙醇、乙酸乙酯等溶剂。合成简单、显色清晰、用碱量少、指示效果比酚酞灵敏，具有很好的实用性。

Description

一种酸碱指示剂及其合成方法与应用
技术领域
本发明属于酸碱指示剂合成技术领域，具体涉及一种酸碱指示剂及其合成方法与应用。
背景技术
β-蒎烯是松节油的主要成分之一，是一种含四元环和六元环的双环单萜烯烃化合物，具有一个环外双键，可进行氧化、异构、加成、氢化、聚合等多种反应，广泛应用于香料、医药、食品、农业、高分子材料等行业中。
酸碱指示剂是一种非常有用的化学试剂，目前主要有硝基酚类、酚酞类、磺代酚酞类、偶氮化合物类等类型，其中酚酞是最为普遍的酸碱指示剂。诺蒎酮是β-蒎烯的氧化衍生物之一，具有重要的应用价值。然而，以诺蒎酮为原料合成酸碱指示剂的研究未见文献报道。本文以绿色、天然可再生的生物质资源β-蒎烯为原料，通过氧化、缩合等手段，成功合成了一种新型蒎烷基酸碱指示剂。该指示剂具有制备简单、稳定性好、指示灵敏的优点。
发明内容
发明目的：本发明的目的是提供一种酸碱指示剂，该指示剂为新型的蒎烷基酸碱指示剂，具有制备简单、得率较高、变色灵敏、指示性能好的优点。本发明的另一目的在于提供一种上述酸碱指示剂的合成方法。本发明还有一目的是提供一种上述酸碱指示剂的应用。
技术方案：为了实现上述发明目的，本发明采用的技术方案为：
一种酸碱指示剂，在酸性环境中显示无色，在碱性环境中示橙黄色，该酸碱指示剂为3-(2′-羟基亚苄基)诺蒎酮。
所述的3-(2′-羟基亚苄基)诺蒎酮能溶于甲醇、乙醇、乙酸乙酯、三氯甲烷、二氯甲烷。
一种所述的3-(2′-羟基亚苄基)诺蒎酮的合成方法，其特征在于，以叔丁醇为溶剂、以叔丁醇钾为催化剂，诺蒎酮与水杨醛在回流状态下进行缩合，得到3-(2′-羟基亚苄基)诺蒎酮。
该合成方法反应式为：
该合成方法的具体步骤为：
1)将10～12mmol诺蒎酮、10～18mmol水杨醛、10～60mL叔丁醇和1～6g叔丁醇钾依次加入配有搅拌器、温度计和回流冷凝器的100-mL三口烧瓶中，搅拌均匀，油浴加热进行回流反应1～8h；
2)反应结束后，反应液先经减压蒸馏回收叔丁醇，剩余物中加入10～30mL水，并用50～60mL乙酸乙酯萃取3次，合并萃取液；用蒸馏水和饱和食盐水洗涤萃取液至中性后，再经无水Na2SO4干燥、过滤、浓缩，再用乙酸乙酯进行重结晶，得到无色透明晶体。
所述的3-(2′-羟基亚苄基)诺蒎酮在制备酸碱指示剂中的应用。
3-(2′-羟基亚苄基)诺蒎酮在酸性环境中不显色、在碱性环境中显橙黄色，显色范围为pH≥8.4。
有益效果：本发明提供的酸碱指示剂为新型蒎烷基指示剂3-(2′-羟基亚苄基)诺蒎酮，具有遇碱由无色变成橙黄色的指示剂性能，显色范围为pH≥8.4。该指示剂，易溶于甲醇、乙醇、乙酸乙酯等溶剂。具有合成简单、显色清晰、用碱量少、指示效果比酚酞灵敏的特点，具有很好的实用性。
具体实施方式
下面结合具体实施例对本发明做出详细说明，这些实例完全是例证性的，仅用来对本发明进行具体描述，而不是对本发明的限制。
实施例1 3-(2′-羟基亚苄基)诺蒎酮的制备
将诺蒎酮10mmol、水杨醛12mmol、叔丁醇30mL和叔丁醇钾2.5g依次加入配有搅拌器、温度计和回流冷凝器的100mL三口烧瓶中，搅拌均匀，油浴加热进行回流反应2h。反应结束后，反应液先经减压蒸馏回收叔丁醇，剩余物中加入30mL水，并用50mL乙酸乙酯萃取2次，合并萃取液。然后，萃取液用饱和食盐水洗至中性，经无水Na2SO4干燥、过滤、浓缩结晶，得到无色透明晶体。
采用MS、IR、NMR、x-射线单晶衍射等方法对无色透明晶体产品进行表征，数据为：mp:238.8-238.9℃；FT-IR(KBr)ν(cm-1):3109,2962,2930,1662,1591,1489,1451,752；1HNMR(DMSO,500MHz):0.82(s,3H,8-CH3),1.31(s,3H,9-CH3),1.34～1.37(d,J＝10.2Hz,1H,7α-CH),2.26-2.27(d,1H,7β-CH),2.51～2.53(t,1H,1-CH),2.54-2.58(m,J＝16.1Hz,1H,5-CH),2.85-2.86(d,2H,4-CH2),6.83-6.85(1.d,1H,3'-CH),6.86-6.94(d,1H,5'-CH),7.18-7.22(m,1H,4'-CH),7.55-7.56(d,1H,6'-CH),7.94(s,1H,10-CH),9.99(s,1H,Ar-OH)；13CNMR(DMSO,75MHz),δ(ppm):21.30,25.81,26.84,30.20,55.24,115.62,118.84,122.17,129.48,129.55,130.38,131.25,157.06,201.88；EI-MS m/z(％):242(M+,20),201(100),199(42),131(59),77(36),55(44)；HRMS(m/z):[M+H]+calcd for C16H18O2+H+,243.1379；found,243.1368。
确定该产品为3-(2′-羟基亚苄基)诺蒎酮，结构式为：
3-(2′-羟基亚苄基)诺蒎酮为无色透明晶体，易溶于甲醇、乙醇、乙酸乙酯等溶剂。3-(2′-羟基亚苄基)诺蒎酮指示剂具有遇碱由无色变成橘黄色的性能，显色范围为pH≥8.4。
实施例2 3-(2′-羟基亚苄基)诺蒎酮酸碱指示剂的应用
利用酚酞与所合成指示剂进行了碱滴定对比试验，以盐酸溶液为实验样品(标定浓度为0.2574mol/L)，采用氢氧化钠溶液(标定浓度为0.1497mol/L)进行滴定实验，实验结果如表1。酚酞指示剂的指示颜色为粉红色，新型蒎烷基指示剂(3-(2′-羟基亚苄基)诺蒎酮)的指示颜色为橘黄色，两种结果的变色效果明显。3-(2′-羟基亚苄基)诺蒎酮和酚酞作为指示剂测定盐酸溶液的浓度分别为0.2596mol/L和0.2610mol/L，通过指示剂指示性能对比实验可知，3-(2′-羟基亚苄基)诺蒎酮测定的浓度更接近于盐酸标定浓度(0.2574mol/L)。结果表明，新合成的蒎烷基指示剂灵敏度更高，效果优于酚酞，是一种理想的酸碱指示剂。
表1 3-(2′-羟基亚苄基)诺蒎酮与酚酞指示剂的对比效果

Claims (5)

1.一种酸碱指示剂，其特征在于，所述的酸碱指示剂在酸性环境中显示无色，在碱性环境中示橙黄色，该酸碱指示剂为3-(2′-羟基亚苄基)诺蒎酮。
2.一种权利要求1所述的3-(2′-羟基亚苄基)诺蒎酮的合成方法，其特征在于，以叔丁醇为溶剂、以叔丁醇钾为催化剂，诺蒎酮与水杨醛在回流状态下进行缩合，得到3-(2′-羟基亚苄基)诺蒎酮。
3.根据权利要求2所述的3-(2′-羟基亚苄基)诺蒎酮的合成方法，其特征在于，具体包括如下步骤：
1)将10～12mmol诺蒎酮、10～18mmol水杨醛、10～60mL叔丁醇和1～6g叔丁醇钾依次加入配有搅拌器、温度计和回流冷凝器的100mL三口烧瓶中，搅拌均匀，油浴加热进行回流反应1～8h；
2)反应结束后，反应液先经减压蒸馏回收叔丁醇，剩余物中加入10～30mL水，并用50～60mL乙酸乙酯萃取3次，合并萃取液；用蒸馏水和饱和食盐水洗涤萃取液至中性后，再经无水Na2SO4干燥、过滤、浓缩，再用乙酸乙酯进行重结晶，得到无色透明晶体。
4.权利要求1所述的3-(2′-羟基亚苄基)诺蒎酮在制备酸碱指示剂中的应用。
5.根据权利要求4所述的应用，其特征在于，3-(2′-羟基亚苄基)诺蒎酮在酸性环境中不显色、在碱性环境中显橙黄色，显色范围为pH≥8.4。
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