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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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。
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 ofα-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.
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 ofα-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.
引文
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[16] SHI Fei,ZHANG Yu,LU Zhaole.et al.Transition-metal-free synthesis of indolizines from electron-deficient alkenes via one-pot reaction using TEMPO as an oxidant[J].Synthesis,2016,48(3):413-420.
[17]王炳祥,胡家欣,胡跃飞,等.由吡啶叶立德和Mannich碱一步合成1-酰基中氮茚衍生物[J].高等学校化学学报,1999,20(3):418-420.WANG Bingxiang,HU Jiaxin,HU Yuefei,et al.A facile one-step synthesis of 1-acylindolizines by the reaction of Pyridinium salts with Mannich bases in the presence of TPCD[J].Chemical Journal of Chinese Universities,1999,20(3):418-420.
[18] SHIPMAN M.Product class 16:indolizines[J].Science of Synthesis,2001,10:745-787.
[19] YURCHENKO R I,DOLINA A V,YURCHENKO A G.Inhibiting action of 1-Phenacylmethyl-2-R-Quinolinium Bromides at steel acid corrosion[J].Russian Journal of Applied Chemistry,2011,84(11):2011-2012.
[20] YURCHENKO R I,DOLINA A V,YURCHENKO A G.Intermolecular synergy effect on the inhibiting action of N-Phenacylmethylquinolinium halides[J].Russian Journal of Applied Chemistry,2011,84(11):2013-2014.
[21] TIWARI L.Mono and bis-ester derivatives of pyridinium and quinolinium compounds as environmentally friendly corrosion inhibitors:WO Patent 20080308770[P].2007-06-14.
[22] BAKSHI D,SINGH A.Transition-metal-free synthesis of nitrogen containing heterocycles with fully substituted N-fused pyrrole rings[J].Asian Journal of Organic Chemistry,2016,5(1):70-73.
[23] ALLGEUER D S,MAYER P,MARY H.Nucleophilicity parameters of pyridinium ylides and their use in mechanistic analyses[J].Journal of the American Chemical Society,2013,135(40):15216-15224.
[24] KRHNKE F,ZECHER W,CURTZE J,et al.Syntheses using the michael adddition of phridinium salts[J].Angewandte Chemie International Edition in English,1962,1(12):626-632.
[25]中国石油天然气总公司.酸化用缓蚀剂性能试验方法及评价指标:SY/T5405—1996[S].北京:石油工业出版社,1996.China National Petroleum Corporation.Experimental instruction and standards for inhibitive performance of inhibitors in acidizing:SY/T5405—1996[S].Beijing:Petroleum Industry Press,1996.
[26] GEORGESCU E,DRAGHICI C,IUHAS P C,et al.A new approach for the synthesis of benzo[f]pyrrolo[1,2-a]-quinolines[J].Arkivoc,2005,2005(10):95-104.
[27] QUAST H,GELLRI A.Heterocyclische Ylide,IV.decarboxylierung von 1-methylchinolinium-2-carboxylat in abwesenheit elektrophiler reagenzien[J].Justus Liebigs Annalen der Chemie,1975,1975(5):929-938.
[28] MAITY A,CHAKRABORTY D,HAZRA A,et al.Novel betaines/mesoionic compounds via a simple and convenient MCR in aqueous micellar system:synthesis of thiazolo[2,3-a]isoquinolin-4-ium derivatives[J].Tetrahedron Letters,2014,55(19):3059-3063.
[29] KANEMASA S,TAKENAKA S,WATANABE H,et al.Tandem1,3-dipolar cycloadditions of pyridinium or isoquinolinium methylides with olefinic dipolarophiles leading to cycl[3.2.2]azines.Enamine route as a new generation method of azomethine ylides[J].Journal of Organic Chemistry,1989,54(2):420-424.
[30]中华人民共和国国家标准.水质化学需氧量的测定重铬酸盐法:GB11914—1989[S].北京:中国标准出版社,1989.National standards of P.R.China.Water quality—Determination of the chemical oxygen demand—Dichromate method:GB11914—1989[S].Beijing:Standards Press of China,1989.
[31] FINGAR M,JACKSON J.Application of corrosion inhibitors for steels in acidic media for the oil and gas industry:a review[J].Corroion Science,2014,86:17-41.
[32] PAN Yuan,ZHAN Fengtao,LV Zhifeng,et al.A Mannich base 1-p henyl-3-(1-pyrrolidinyl)-1-propanone:synthesis and performance study on corrosion inhibition for N80 steel in 15%hydrochloric acid[J].Anti-Corrosion Methods and Materials,2016,63(2):153-159.
[33]宗鹏.季铵盐型酸化缓蚀剂的合成及其缓蚀机理研究[D].青岛:中国石油大学,2008.ZONG Peng.Synthetise and corrosion inhibition mechanism investigation of quaternary ammonium corrosion inhibitors for acidification[D].Qingdao:China University of Petroleum,2008.
[34] HOU Baofeng,WANG Yefei,HUANG Yong.Mechanistic study of wettability alteration of oil-wet sandstone surface using different surfactants[J].Applied Surface Science,2015,330:56-64.
[35] POPOVA A,CHRISTOV M,VASILEV A.Mono-and dicationic benzothiazolic quaternary ammonium bromides as mild steel corrosion inhibitors.Part II:Electrochemical impedance and polarisation resistance results[J].Corrosion Science,2011,53(5):1770-1777.
[2]何延龙,蒲春生,董巧玲,等.水力脉冲波协同多氢酸酸化解堵反应动力学模型[J].石油学报,2016,37(4):499-507.HE Yanlong,PU Chunsheng,DONG Qiaoling et al.Kinetic model of plug removal reaction based on a synergy between hydraulic pulse wave and multi-hydracid acidification[J].Acta Petrolei Sin-ica,2016,37(4):499-507.
[3]赵福麟.采油用剂[M].东营:石油大学出版社,1997:171.ZHAO Fulin.Agent for oil production[M].Dongying:China University of Petroleum Press,1997:171.
[4]张鹏,彭杨.考虑随机变量相关性的腐蚀管道失效概率[J].石油学报,2016,37(10):1293-1301.ZHANG Peng,PENG Yang.Failure probability of corroded pipeline considering random variables correlation[J].Acta Petrolei Sinica,2016,37(10):1293-1301.
[5]张新生,李亚云,王小完.基于逆高斯过程的腐蚀油气管道维修策略[J].石油学报,2017,38(3):356-362.ZHANG Xinsheng,LI Yayun,WANG Xiaowan.Maintenance strategy of corroded oil-gas pipeline based on inverse Gaussian process[J].Acta Petrolei Sinica,2017,38(3):356-362.
[6]张智,刘志伟,谢玉洪,等.井筒载荷-腐蚀耦合作用对碳钢套管服役寿命的影响[J].石油学报,2017,38(3):342-347.ZHANG Zhi,LIU Zhiwei,XIE Yuhong,et al.Influence of shaft load-corrosion coupling on the service life of carbon steel casing pipe[J].Acta Petrolei Sinica,2017,38(3):342-347.
[7] POPOVA A,CHRISTOV M,VASILEV A,et al.Mono-and dicationic benzothiazolic quaternary ammonium bromides as mild steel corrosion inhibitors.Part I:Gravimetric and voltammetric results[J].Corrosion Science,2011,53(2):679-686.
[8] ZHANG Xiaoyun,ZHENG Yunxiang,WANG Xiangpeng,et al.Corrosion inhibition of N80 steel using novel diquaternary ammonium salts in 15%hydrochloric acid[J].Industrial&Engineering Chemistry Research,2014,53(37):14199-14207.
[9] FRENIER W W.Low hazard corrosion inhibitors and cleaning solutions using quaternary ammonium salts:U.S.Patent6521028[P].2003-02-18.
[10]战风涛,杨震,吕志凤,等.高效缓蚀性氯化苄基喹啉衍生物制备与表征[J].石油学报,2015,36(9):1116-1121.ZHAN Fengtao,YANG Zhen,LZhifeng,et al.Preparation and characterization of N-Benzylquinolinium Chloride Derivative(BQD)with effective corrosion inhibition[J].Acta Petrolei Sinica,2015,36(9):1116-1121.
[11] YANG Zhen,ZHAN Fengtao,PAN Yuan,et al.Structure of a novel Benzyl Quinolinium Chloride derivative and its effective corrosion inhibition in 15 wt.%hydrochloric acid[J].Corrosion Science,2015,99:281-294.
[12]杨震.氯化苄基喹啉衍生物的高效缓蚀性能研究[C]∥中国腐蚀与防护学会缓蚀剂专业委员会.第十八届全国缓蚀剂学术讨论会论文集.湖北:中国腐蚀与防护学会缓蚀剂专业委员会:2014.YANG Zhen.Research on N-benzylquinolinium chloride derivatives and its effective anti-corrosion performance[C]∥Professional Committee of Corrosion Inhibitors of Chinese Society of Corrosion and Protection.Papers of the 18th National Symposium on Corrosion Inhibitors.Hubei:Professional Committee of Corrosion Inhibitors of Chinese Society of Corrosion and Protection:2014.
[13]吕志凤,战风涛,王晓娜,等.氯乙酸乙酯喹啉季铵盐衍生物的合成及其酸化缓蚀性能[J].材料保护,2018,51(5):25-29.LYU Zhifeng,ZHAN Feng-tao,WANG Xiao-na,et al.Synthesis of Ethyl Chloroacetate Quinolinium Salt Derivatives and Evaluation of Its Acidification Inhibition Corrosion Properties[J].Materials Protection,2018,51(5):25-29.
[14] WANG Yefei,YANG Zhen,ZHAN Fengtao et al.Indolizine quaternary ammonium salt inhibitors part II:a reinvestigation of an old-fashioned strong acid corrosion inhibitor phenacyl quinolinium bromide and its indolizine derivative,New Journal of Chemistry,2018,42:12977-12989.
[15] LIU Yan,HU Huayou,ZHOU Junyu,et al.Application of primary halogenated hydrocarbons for the synthesis of 3-aryl and3-alkyl indolizines[J].Organic&Biomolecular Chemistry,2017,15(23):5016-5024.
[16] SHI Fei,ZHANG Yu,LU Zhaole.et al.Transition-metal-free synthesis of indolizines from electron-deficient alkenes via one-pot reaction using TEMPO as an oxidant[J].Synthesis,2016,48(3):413-420.
[17]王炳祥,胡家欣,胡跃飞,等.由吡啶叶立德和Mannich碱一步合成1-酰基中氮茚衍生物[J].高等学校化学学报,1999,20(3):418-420.WANG Bingxiang,HU Jiaxin,HU Yuefei,et al.A facile one-step synthesis of 1-acylindolizines by the reaction of Pyridinium salts with Mannich bases in the presence of TPCD[J].Chemical Journal of Chinese Universities,1999,20(3):418-420.
[18] SHIPMAN M.Product class 16:indolizines[J].Science of Synthesis,2001,10:745-787.
[19] YURCHENKO R I,DOLINA A V,YURCHENKO A G.Inhibiting action of 1-Phenacylmethyl-2-R-Quinolinium Bromides at steel acid corrosion[J].Russian Journal of Applied Chemistry,2011,84(11):2011-2012.
[20] YURCHENKO R I,DOLINA A V,YURCHENKO A G.Intermolecular synergy effect on the inhibiting action of N-Phenacylmethylquinolinium halides[J].Russian Journal of Applied Chemistry,2011,84(11):2013-2014.
[21] TIWARI L.Mono and bis-ester derivatives of pyridinium and quinolinium compounds as environmentally friendly corrosion inhibitors:WO Patent 20080308770[P].2007-06-14.
[22] BAKSHI D,SINGH A.Transition-metal-free synthesis of nitrogen containing heterocycles with fully substituted N-fused pyrrole rings[J].Asian Journal of Organic Chemistry,2016,5(1):70-73.
[23] ALLGEUER D S,MAYER P,MARY H.Nucleophilicity parameters of pyridinium ylides and their use in mechanistic analyses[J].Journal of the American Chemical Society,2013,135(40):15216-15224.
[24] KRHNKE F,ZECHER W,CURTZE J,et al.Syntheses using the michael adddition of phridinium salts[J].Angewandte Chemie International Edition in English,1962,1(12):626-632.
[25]中国石油天然气总公司.酸化用缓蚀剂性能试验方法及评价指标:SY/T5405—1996[S].北京:石油工业出版社,1996.China National Petroleum Corporation.Experimental instruction and standards for inhibitive performance of inhibitors in acidizing:SY/T5405—1996[S].Beijing:Petroleum Industry Press,1996.
[26] GEORGESCU E,DRAGHICI C,IUHAS P C,et al.A new approach for the synthesis of benzo[f]pyrrolo[1,2-a]-quinolines[J].Arkivoc,2005,2005(10):95-104.
[27] QUAST H,GELLRI A.Heterocyclische Ylide,IV.decarboxylierung von 1-methylchinolinium-2-carboxylat in abwesenheit elektrophiler reagenzien[J].Justus Liebigs Annalen der Chemie,1975,1975(5):929-938.
[28] MAITY A,CHAKRABORTY D,HAZRA A,et al.Novel betaines/mesoionic compounds via a simple and convenient MCR in aqueous micellar system:synthesis of thiazolo[2,3-a]isoquinolin-4-ium derivatives[J].Tetrahedron Letters,2014,55(19):3059-3063.
[29] KANEMASA S,TAKENAKA S,WATANABE H,et al.Tandem1,3-dipolar cycloadditions of pyridinium or isoquinolinium methylides with olefinic dipolarophiles leading to cycl[3.2.2]azines.Enamine route as a new generation method of azomethine ylides[J].Journal of Organic Chemistry,1989,54(2):420-424.
[30]中华人民共和国国家标准.水质化学需氧量的测定重铬酸盐法:GB11914—1989[S].北京:中国标准出版社,1989.National standards of P.R.China.Water quality—Determination of the chemical oxygen demand—Dichromate method:GB11914—1989[S].Beijing:Standards Press of China,1989.
[31] FINGAR M,JACKSON J.Application of corrosion inhibitors for steels in acidic media for the oil and gas industry:a review[J].Corroion Science,2014,86:17-41.
[32] PAN Yuan,ZHAN Fengtao,LV Zhifeng,et al.A Mannich base 1-p henyl-3-(1-pyrrolidinyl)-1-propanone:synthesis and performance study on corrosion inhibition for N80 steel in 15%hydrochloric acid[J].Anti-Corrosion Methods and Materials,2016,63(2):153-159.
[33]宗鹏.季铵盐型酸化缓蚀剂的合成及其缓蚀机理研究[D].青岛:中国石油大学,2008.ZONG Peng.Synthetise and corrosion inhibition mechanism investigation of quaternary ammonium corrosion inhibitors for acidification[D].Qingdao:China University of Petroleum,2008.
[34] HOU Baofeng,WANG Yefei,HUANG Yong.Mechanistic study of wettability alteration of oil-wet sandstone surface using different surfactants[J].Applied Surface Science,2015,330:56-64.
[35] POPOVA A,CHRISTOV M,VASILEV A.Mono-and dicationic benzothiazolic quaternary ammonium bromides as mild steel corrosion inhibitors.Part II:Electrochemical impedance and polarisation resistance results[J].Corrosion Science,2011,53(5):1770-1777.