Synthesis and acidizing corrosion inhibition of the dimer indolizine derivative of quinolinium quaternary ammonium salts

doi:10.7623/syxb201901005

Acta Petrolei Sinica ›› 2019, Vol. 40 ›› Issue (1): 67-73,114.DOI: 10.7623/syxb201901005

• Oil Field Development • Previous Articles Next Articles

Synthesis and acidizing corrosion inhibition of the dimer indolizine derivative of quinolinium quaternary ammonium salts

Wang Yefei^1,2,3, Yang Zhen^1,2,3, Zhan Fengtao⁴, Hu Songqing⁵, Chen Wuhua^1,2,3, Ding Mingchen^1,2,3

1. Key Laboratory of Unconventional Oil & Gas Development of the Ministry of Education, China University of Petroleum, Shandong Qingdao 266580, China;
2. Shandong Key Laboratory of Oilfield Chemistry, School of Petroleum Engineering, China University of Petroleum, Shandong Qingdao 266580, China;
3. School of Petroleum Engineering, China University of Petroleum, Shandong Qingdao 266580, China;
4. College of Science, China University of Petroleum, Shandong Qingdao 266580, China;
5. School of Materials Science and Engineering, China University of Petroleum, Shandong Qingdao 266580, China

Received:2018-03-23 Revised:2018-10-15 Online:2019-01-25 Published:2019-01-29

喹啉季铵盐二聚体吲哚嗪衍生物的合成与酸化缓蚀性能

王业飞^1,2,3, 杨震^1,2,3, 战风涛⁴, 胡松青⁵, 陈五花^1,2,3, 丁名臣^1,2,3

1. 中国石油大学非常规油气开发教育部重点实验室山东青岛 266580;
2. 中国石油大学石油工程学院山东省油田化学重点实验室山东青岛 266580;
3. 中国石油大学石油工程学院山东青岛 266580;
4. 中国石油大学理学院山东青岛 266580;
5. 中国石油大学材料科学与工程学院山东青岛 266580

通讯作者: 王业飞,男,1968年9月生,1991年获石油大学(华东)学士学位,1998年获石油大学(华东)博士学位,现为中国石油大学(华东)教授、博士生导师,主要从事油田化学品和新型表面活性剂的研发,提高采收率与采油化学及物理化学课程的科研与教学工作。Email:wangyf@upc.edu.cn
作者简介:王业飞,男,1968年9月生,1991年获石油大学(华东)学士学位,1998年获石油大学(华东)博士学位,现为中国石油大学(华东)教授、博士生导师,主要从事油田化学品和新型表面活性剂的研发,提高采收率与采油化学及物理化学课程的科研与教学工作。Email:wangyf@upc.edu.cn
基金资助:
中央高校基本科研业务费专项资金项目（16CX06030A）资助。

Abstract

Abstract:

The research of acidizing technology for oil and gas wells always focuses on the novel acidizing corrosion inhibitor with high performance. BQC(Benzyl Quinolinium Chloride)is a common acidizing corrosion inhibitor, and its dimer derivative BQD has even higher corrosion inhibition performance. However, BQD is a dimer indolizne derivative, generated by its precursor BQC undergoing intermolecular 1, 3-dipolar cycloaddition reactions. According to the conditions of 1, 3-dipolar cycloaddition, the dimer indolizine derivative of Phenacyl Quinolinium Bromide(Di-PaQBr)and the dimer indolizine derivative of Ethyl Acetate Quinolinium Bromide(Di-EAQBr)were synthesized successfully from Phenacyl Quinolinium Bromide(PaQBr)and Ethyl Acetate Quinolinium Bromide(EAQBr)respectively. The yields of two derivatives were increased by enhancing the activity of α-H group in quaternary ammonium salts of the precursor. The structures of Di-PaQBr and Di-EAQBr were identified by high resolution mass spectrum(HRMS), magnetic resonance imaging(NMR)and other technologies, thus confirming the reaction mechanism of dimer indolizine derivative from two quaternary quinolinium moleculars via 1, 3-dipolar cycloaddition. The corrosion inhibitions of PaQBr, EAQBr, Di-PaQBr and Di-EAQBr for N80 steel were evaluated by static weight loss method. The corrosion inhibitions of the two derivatives were significantly superior to original quaternary quinolinium salts in 15% hydrochloric acid at 90℃. It is indicated that when the heterocyclic quaternary ammonium salts are transformed to their dimer indolizine derivative, the corrosion inhibition is likely to be promoted significantly.

Key words: acidification, corrosion inhibitor, quinolinium quaternary ammonium salt, heterocyclic base, indolizine derivative, 1,3-dipolar cycloaddition

摘要：

开发新型、高效酸化缓蚀剂是油气井酸化技术的研究重点之一。氯化苄基喹啉（BQC）是一种常用的酸化缓蚀剂，其二聚体衍生物BQD具有更高效的缓蚀性能。而BQD实际上是由其前体物质BQC经分子间1，3-偶极环加成反应而得到的一种二聚体吲哚嗪衍生物。参照1，3-偶极环加成反应条件，分别由溴化苯甲酰甲基喹啉季铵盐（PaQBr）及溴化乙酸乙酯基喹啉季铵盐（EAQBr）成功地合成了溴化苯甲酰甲基喹啉二聚体吲哚嗪衍生物（Di-PaQBr）和溴化乙酸乙酯基喹啉二聚体吲哚嗪衍生物（Di-EAQBr），通过增强前体季铵盐中α-H的活性提高了衍生物的产率。采用高分辨质谱（HRMS）以及核磁共振（NMR）等技术确认了两种二聚体吲哚嗪衍生物的结构，并由此证实了由两分子喹啉季铵盐经1，3-偶极环加成反应得到二聚体吲哚嗪衍生物的反应机理。通过静态失重法对比考察了两种喹啉季铵盐与相应二聚体吲哚嗪衍生物的缓蚀性能。衍生物在90℃、15%盐酸中对N80钢的缓蚀性能均明显优于相应前体物喹啉季铵盐，说明当杂环碱季铵盐转化为其二聚体吲哚嗪衍生物后，缓蚀性能可得到显著提高。

关键词: 酸化, 缓蚀剂, 喹啉季铵盐, 杂环碱, 吲哚嗪衍生物, 1, 3-偶极环加成反应

CLC Number:

TE357.2

Wang Yefei, Yang Zhen, Zhan Fengtao, Hu Songqing, Chen Wuhua, Ding Mingchen. Synthesis and acidizing corrosion inhibition of the dimer indolizine derivative of quinolinium quaternary ammonium salts[J]. Acta Petrolei Sinica, 2019, 40(1): 67-73,114.

王业飞, 杨震, 战风涛, 胡松青, 陈五花, 丁名臣. 喹啉季铵盐二聚体吲哚嗪衍生物的合成与酸化缓蚀性能[J]. 石油学报, 2019, 40(1): 67-73,114.

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Synthesis and acidizing corrosion inhibition of the dimer indolizine derivative of quinolinium quaternary ammonium salts

喹啉季铵盐二聚体吲哚嗪衍生物的合成与酸化缓蚀性能

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