磷酸型化合物设计合成方法研究进展
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摘要
磷元素作为"生命活动的调控中心"而备受关注,磷化合物凭借优异的性能及在众多领域的广泛应用,吸引着许多科学家在磷化合物设计、合成与性能方面开展了大量、深入和系统的研究工作,在高端日化、医药卫生以及生命科学等理论与应用方面取得丰硕的成果。但原子经济性、产业化应用、环境友好性以及绿色产业化方面有待进一步提高。在近年来研究基础上,系统地综述了设计合成磷化合物的Kabachnik-Fields反应、Atherton-Todd反应、Abramov反应等及反应机理,为构筑新型磷酸酯型化合物、开发该类化合物的新功能提供重要参考,同时对含磷化合物在三次采油、航空航天等应用领域的发展趋势进行了展望。
Phosphorus has attracted much attention as a "regulatory center for life activities". The excellent performance of phosphorus compounds and its wide application in many fields have attracted many scientists to carry out extensive, in-depth and systematic research work on the design, synthesis and performance of phosphorus compounds.High-end daily, medical and health sciences and life sciences have achieved fruitful results in theory and application. However, the aspects of atomic economy, industrial application, environmental friendliness and green industrialization need to be further improved. Based on recent studies, this paper systematically reviews the Kabachnik-Fields reaction, Atherton-Todd reaction and other reaction mechanisms for the design and synthesis of phosphorus compounds. Provide an important reference for constructing new phosphate ester compounds and developing new functions for such compounds. At the same time, the development trend of phosphorus-containing compounds in tertiary oil recovery, aerospace and other application fields is prospective.
Phosphorus has attracted much attention as a "regulatory center for life activities". The excellent performance of phosphorus compounds and its wide application in many fields have attracted many scientists to carry out extensive, in-depth and systematic research work on the design, synthesis and performance of phosphorus compounds.High-end daily, medical and health sciences and life sciences have achieved fruitful results in theory and application. However, the aspects of atomic economy, industrial application, environmental friendliness and green industrialization need to be further improved. Based on recent studies, this paper systematically reviews the Kabachnik-Fields reaction, Atherton-Todd reaction and other reaction mechanisms for the design and synthesis of phosphorus compounds. Provide an important reference for constructing new phosphate ester compounds and developing new functions for such compounds. At the same time, the development trend of phosphorus-containing compounds in tertiary oil recovery, aerospace and other application fields is prospective.
引文
[1]Huang Xiaoli(黄晓丽). Study in the synthesis and transformation ofα-carbamatemethylphosphonateandoxaziridine[D].Zunyi:Zunyi Medical University(遵义医学院), 2017.
[2]Liu Shuang(刘双), Li Yuming(李玉明), Wang Dian(王典), et al.Researchprogressofasymmetricsynthesisofopticallyactive P-stereogenic organophosphoryl compounds by chiral induction[J].Chinese Journal Organic Chemistry(有机化学), 2018, 38:341-349.
[3]Mahesh R S, Mukunda P K, Dibya S S. et al. Outcome of low dose cyclophosphamide for induction phase treatment of lupus nephritis, a single center study[J]. BMC Nephrology, 2016, 17:104.
[4]Han Guosheng(韩国胜), He Cheng(何成), Zhao Junfeng(赵军峰),etal.Synthesisandcharacterizationofphosphorylderivativesof dihydroxy anthraquinones[J]. Chinese Journal Organic Chemistry(有机化学), 2011, 31(11):1848-1851.
[5]Zheng Yi(郑毅), Yang Yifeng(杨艺峰), Li Hua(李华), et al. New typecoatingchooseforPCBAofspaceingmodelproducts[J].ElectronicsProcessTechnology(电子工艺技术),2015,36(2):89-93.
[6]Wu Wangbo(吴望波), Zhao Li(赵莉), Zhang Huatao(张华涛), et al. Performance and applications of surfactants(ⅩⅩⅥ)applications ofsurfactantsincosmetics[J].ChinaSurfactantDetergent&Cosmetics(日用化学工业), 2016, 46(2):75-79.
[7]YangJia(杨佳),XiaoJing(肖晶),ZhouYongbo(周永波),etal.Recentadvancesinthesynthesisoforganophosphoruscompounds viacrosscouplingbetweenreadilyavailablematerialsandP-H compounds[J].ChineseJournalOrganicChemistry(有机化学),2017, 37:1055-1068.
[8]ChengYuqiao(程玉桥),LiangShuqin(梁书芹),ZhangXiansong(张贤松), et al. Research progress of gemini type oil displacement agentintermediatesdoubleend-cappingagentv[J].FineChemicals(精细化工), 2017, 34(12):1321-1328.
[9]Peng Zhongli(彭忠利), Duan Xianjian(段先建), Huang Guoshu(黄国书). Surface modification of nano-silica by organic phophorus and its application in polypropylene[J]. China Plastics(中国塑料), 2016,30(2):59-63.
[10]Cui Xuyuan(崔旭元), Gao Wanxian(高万贤). Research status and development prospect of biomimetic superhydrophobic materials[J].Knitting Industries(针织工业), 2018,(1):63-67.
[11]Stéphanie L C, Mathieu B, Hélène C G, et al. Atherton-Todd reaction:Mechanism,scopeandapplications[J].BeilsteinJournalOrganic Chemistry, 2014, 10:1166-1196.
[12]CherkasovRA,GalkinVI.TheKabachnik-Fieldsreaction:Syntheticpotentialandtheproblemofthemechanism[J].Russian Chemical Reviews, 1998, 67(10):857-882.
[13]GuinJ,WangQ,ManuelVG,etal.Thecatalyticasymmetric Abramovreaction[J].AngewandteChemieInternationalEdition,2014, 54(1):355-358.
[14]Qu Zhibo(屈智博). Applications of H-phosphonates in synthesis of phosphorus-containingfunctionalcompounds[D].Zhengzhou:Zhengzhou University(郑州大学), 2012.
[15]Gy?rgy K, Erika B. The Kabachnik-Fields reaction:Mechanism and synthetic use[J]. Molecules,2012, 17:12821-12835.
[16]Wan Dehui(万德惠). Chiral BINOL-amino acid schiff bases and its metalliccomplexesascatalystsforasymmertricKabachnik-Fields reaction[D].Haikou:HainanNormalUniversity(海南师范大学),2013.
[17]Liang Jing(梁静). Study on the synthesis of P, N-heterocycles[D].Xuzhou:China University of Mining and Technology(中国矿业大学), 2015.
[18]Wang Yufeng(王玉凤), Yang Yajie(杨雅杰), Huang Ling(黄玲), et al. Iodine catalyzed Kabachnik-Fields reaction of trialkyl phosphites:Facileaccesstobenzoxazinecontainingphosphorus[J].Chinese Journal Organic Chemistry(有机化学), 2017, 37(12):3220-3228.
[19]ErikaB,EszterF,PéterP,etal.N-BenzylandN-aryl bis(phospha-Mannich adducts):Synthesis and catalytic activity of the related bidentate chelate platinum complexes in hydroformylation[J].Journal of Organometallic Chemistry, 2012, 717:75-82.
[20]FangYilin(方毅林).Synthesisandbiologicalactivitiesof quinolin-2(1H)-one derivatives[D]. Changsha:Hunan University(湖南大学), 2016.
[21]GaoPeng(高鹏).StudyontheCO2insertionreactionand mechanismsofchiralbisaminohydrospirosphoraneswithsecond amines[D]. Zhengzhou:Zhengzhou University(郑州大学), 2014.
[22]You Xiaohui(游晓辉). The Investigation of the stereochemistry of the Atherton-Todd-type reactions of bis(aminoacyl)spirophosphoranes containing a chiral phosphorus center with phenols[D]. Zhengzhou:Zhengzhou University(郑州大学), 2015.
[23]DaiWang(代旺).Researchesonthereactionsandmechanismsof bisamino hydrospirophosphoranes with allylic halides[D]. Zhengzhou:Zhengzhou University(郑州大学), 2016.
[24]WangWY,JinHA,YanZH,etal.Perfluoroalkanosulfonyl fluoride-assistedAtherton–Todd-likereactionofdiphenylphosphine oxidewithalcoholsunderairgeneratingdiphenylphosphinate esters[J]. Tetrahedron Letters, 2017, 58(36):3489-3492.
[25]Xu Kai(许凯). Palladium-catalyzed the coupling reaction involving dialkylH-phosphonateorterminalalkynes[D].Zhengzhou:Zhengzhou University(郑州大学), 2013.
[26]LuoSha(罗莎).ApplicationsofmetalcatalyzedC—Hbonds activation in the synthesis of pharmaceutically active units[D]. Wuxi:Jiangnan University(江南大学), 2014.
[27]Min Zehui(闵泽辉). Synthesis ofα-indole phosphonate ester based on CDC reaction[D]. Changsha:Hunan University(湖南大学), 2015.
[28]ZhangYun(张云).Studiesofcopper-catalyzeddecarboxylative coupling reaction ofα,β-unsaturated carboxylic acids with CF3CH2I Or HP(O)(OiPr)2[D]. Zhengzhou:Zhengzhou University(郑州大学),2017.
[29]YoshihiroS,NatsukoH,RikaT,etal.Enantioselectivephosphamichael reaction of diphenyl phosphonate with nitroolefins utilizing conformationallyflexibleguanidinium/bisthioureaorganocatalyst:assembly-state tunability inasymmetric organocatalysis[J].Advanced Synthesis&Catalysis, 2011, 353(14/15):2631-2636.
[30]Li G Y, Wang L, Yao Z G, et al. Chiral ytterbium silylamide catalyzed enantioselectivephospha-Michaeladditionofdiethylphosphiteto chalcones[J]. Tetrahedron:Asymmetry, 2014, 25(13/14):989-996.
[31]LuoYongyang(罗永阳).Directcatalyticasymmetricmichael addition reaction of dialkyl phosphites to 2-benzylidene-1-indanones byachiraldinuclearzinccatalyst[D].Zhengzhou:Zhengzhou University(郑州大学), 2017.
[32]KolodyazhnaAO;GrishkunEV,KolodyazhnyiOI.Synthesisof chiralphosphonobenzaldehydesandphosphonotyrosine[J].Russian Journal of General Chemistry,2017, 87:5.
[33]ZhaoYalei(赵亚磊).StudiesonthetransformationofP(O)—H bonds and its application in organic synthesis[D]. Changsha:Hunan University(湖南大学), 2015.
[34]LiuMingyu(刘明玉).Evaluationoftwoanimalmodelsof hyperuricemiabasedonlipidmetabolomics[D].Beijing:Beijing Univesity of Chinese Medicixe(北京中医药大学), 2018.
[35]Xie Xinqiang(谢新强). Phosphorothioate DNA as an antioxidant in bacteria[D].Shanghai:ShanghaiJiaoTongUniversity(上海交通大学), 2012.
[36]Zhao Yufen(赵玉芬), Li Yanmei(李艳梅). Phosphor chemistry and process of life chemistry[J]. Science and Technology Review(科技导报), 1994,(3):6-8.
[37]Dai Zhengqing(戴政清), Wang Yuen(王宇恩), Liu Jian(刘剑), et al. Progress on the synthesis of phosphopeptides by the Fmoc solidphasestrategy[J]. Chinese Journal of Medicinal Chemistry(中国药物化学杂志), 2011, 21(1):70-76.
[38]Wang Jingyan(王镜岩), Zhu Shenggeng(朱圣庚), Xu Changfa(徐长法).Biochemistry[M].Thirdedition.Beijing:HigherEducation Press(高等教育出版社), 2002:548.
[39]Mei Fangyi(梅方义), Cao Dong(曹栋). Preparation of a new kind ofmixedmicellebasedonphosphatidylcholineandnonionic surfactant[J]. Science and Technology of Food Industry(食品工业科技), 2011, 33(6):336-339.
[40]ZhangJun(张军),ZhanJiefang(詹结钫).Theperformanceand mechanismofemulsifieranditsapplicationincosmetic formulations[J]. Scientific and Technological Innovation(科学技术创新), 2018,(21):26-27.
[41]Zhang Wei(张玮), Wang Aijun(王爱军), Kou Yinke(寇寅客). On the synthesis of the vitamin C derivatives in cosmetic[J]. Journal of Shijiazhuang Vocational Technology Institute(石家庄职业技术学院学报), 2008, 20(2):11-13.
[42]Zhai Shaohua(翟少华), Jia Qinrui(贾钦瑞), Li Shuxian(李淑娴), et al. Microscopy and ultrastructure morphological study on skin tissue ofbullfrog[J].ChineseJournalofWildlife(野生动物学报),2018,39(1):105-109.
[43]ZhaoJuan(赵娟).Theapplicationresearchofautologousskin fibroblasts in medical cosmetology[D]. Changchun:Jilin University(吉林大学), 2007.
[44]Gu Renwan(顾仁碗), Zhang Hongzhi(张宏志). Aircraft corrosion and protection[J]. Science and Technology&Innovation(科技与创新), 2018,(12):68-70.
[45]An Haiming(安海明). Special-shaped tube cleaning and cleanliness testingtechnologyresearch[D].Shenyang:ShenyangAerospace University(沈阳航空航天大学), 2018.
[46]ZhangHongrui(张洪瑞).Designandsimulationofahigh cleanlinesscleaningeruipmentforairafttubes[D].Shenyang:Shenyang Aerospace University(沈阳航空航天大学), 2016.
[47]Shang Hufeng(商虎峰), Shi Baojun(师保俊), Zhang Huzhen(张祜珍),etal.Thedesignofaircraftpartscleaningproductionline automaticcontrolsystembasedonPLC[J].Manufacturing Automation(制造业自动化), 2018, 40(7):94-98.
[48]Liu Gengxin(刘庚鑫). A new material to improve the effectiveness andlongevityofmaterialcivilization—Ontheapplicationofnew technology of nano coating[J]. Total Corrosion Control(全面腐蚀控制), 2018, 32(7):1-5.
[49]Yang Yang(杨洋), Zhao Kui(赵奎), Zhu Hongbo(朱鸿博). Green chemistry-Anewconceptofchemistry[J].ChemicalEnterprise Management(化工管理), 2018,(14):17-18.
[50]Chen Xiaoping(陈小萍), Liu Junkang(刘俊康), Chen Yepu(陈烨璞),etal.Propertiesofnano-CaCO3modifiedbyaseriousof phosphatesurfactantsandtheirapplicationinPVC[J].Journalof Southern Yangtze University(Natural Science Edition)(江南大学学报:自然科学版), 2002,(3):266-268.
[51]Li Naishi(李乃师), Zhao Xudong(赵旭东), Fu Yanli(付彦丽), et al.Researchstatusandfuturedevelopmentoftertiaryoilrecovery technology[J]. Chemical Enterprise Management(化工管理), 2018,(18):121-122.
[52]LiYuan(李原).Studyonapplicationofaluminananofluidsin surfactantflooding[D].Chengdu:SouthwestPetroleumUniversity(西南石油大学), 2017.
[2]Liu Shuang(刘双), Li Yuming(李玉明), Wang Dian(王典), et al.Researchprogressofasymmetricsynthesisofopticallyactive P-stereogenic organophosphoryl compounds by chiral induction[J].Chinese Journal Organic Chemistry(有机化学), 2018, 38:341-349.
[3]Mahesh R S, Mukunda P K, Dibya S S. et al. Outcome of low dose cyclophosphamide for induction phase treatment of lupus nephritis, a single center study[J]. BMC Nephrology, 2016, 17:104.
[4]Han Guosheng(韩国胜), He Cheng(何成), Zhao Junfeng(赵军峰),etal.Synthesisandcharacterizationofphosphorylderivativesof dihydroxy anthraquinones[J]. Chinese Journal Organic Chemistry(有机化学), 2011, 31(11):1848-1851.
[5]Zheng Yi(郑毅), Yang Yifeng(杨艺峰), Li Hua(李华), et al. New typecoatingchooseforPCBAofspaceingmodelproducts[J].ElectronicsProcessTechnology(电子工艺技术),2015,36(2):89-93.
[6]Wu Wangbo(吴望波), Zhao Li(赵莉), Zhang Huatao(张华涛), et al. Performance and applications of surfactants(ⅩⅩⅥ)applications ofsurfactantsincosmetics[J].ChinaSurfactantDetergent&Cosmetics(日用化学工业), 2016, 46(2):75-79.
[7]YangJia(杨佳),XiaoJing(肖晶),ZhouYongbo(周永波),etal.Recentadvancesinthesynthesisoforganophosphoruscompounds viacrosscouplingbetweenreadilyavailablematerialsandP-H compounds[J].ChineseJournalOrganicChemistry(有机化学),2017, 37:1055-1068.
[8]ChengYuqiao(程玉桥),LiangShuqin(梁书芹),ZhangXiansong(张贤松), et al. Research progress of gemini type oil displacement agentintermediatesdoubleend-cappingagentv[J].FineChemicals(精细化工), 2017, 34(12):1321-1328.
[9]Peng Zhongli(彭忠利), Duan Xianjian(段先建), Huang Guoshu(黄国书). Surface modification of nano-silica by organic phophorus and its application in polypropylene[J]. China Plastics(中国塑料), 2016,30(2):59-63.
[10]Cui Xuyuan(崔旭元), Gao Wanxian(高万贤). Research status and development prospect of biomimetic superhydrophobic materials[J].Knitting Industries(针织工业), 2018,(1):63-67.
[11]Stéphanie L C, Mathieu B, Hélène C G, et al. Atherton-Todd reaction:Mechanism,scopeandapplications[J].BeilsteinJournalOrganic Chemistry, 2014, 10:1166-1196.
[12]CherkasovRA,GalkinVI.TheKabachnik-Fieldsreaction:Syntheticpotentialandtheproblemofthemechanism[J].Russian Chemical Reviews, 1998, 67(10):857-882.
[13]GuinJ,WangQ,ManuelVG,etal.Thecatalyticasymmetric Abramovreaction[J].AngewandteChemieInternationalEdition,2014, 54(1):355-358.
[14]Qu Zhibo(屈智博). Applications of H-phosphonates in synthesis of phosphorus-containingfunctionalcompounds[D].Zhengzhou:Zhengzhou University(郑州大学), 2012.
[15]Gy?rgy K, Erika B. The Kabachnik-Fields reaction:Mechanism and synthetic use[J]. Molecules,2012, 17:12821-12835.
[16]Wan Dehui(万德惠). Chiral BINOL-amino acid schiff bases and its metalliccomplexesascatalystsforasymmertricKabachnik-Fields reaction[D].Haikou:HainanNormalUniversity(海南师范大学),2013.
[17]Liang Jing(梁静). Study on the synthesis of P, N-heterocycles[D].Xuzhou:China University of Mining and Technology(中国矿业大学), 2015.
[18]Wang Yufeng(王玉凤), Yang Yajie(杨雅杰), Huang Ling(黄玲), et al. Iodine catalyzed Kabachnik-Fields reaction of trialkyl phosphites:Facileaccesstobenzoxazinecontainingphosphorus[J].Chinese Journal Organic Chemistry(有机化学), 2017, 37(12):3220-3228.
[19]ErikaB,EszterF,PéterP,etal.N-BenzylandN-aryl bis(phospha-Mannich adducts):Synthesis and catalytic activity of the related bidentate chelate platinum complexes in hydroformylation[J].Journal of Organometallic Chemistry, 2012, 717:75-82.
[20]FangYilin(方毅林).Synthesisandbiologicalactivitiesof quinolin-2(1H)-one derivatives[D]. Changsha:Hunan University(湖南大学), 2016.
[21]GaoPeng(高鹏).StudyontheCO2insertionreactionand mechanismsofchiralbisaminohydrospirosphoraneswithsecond amines[D]. Zhengzhou:Zhengzhou University(郑州大学), 2014.
[22]You Xiaohui(游晓辉). The Investigation of the stereochemistry of the Atherton-Todd-type reactions of bis(aminoacyl)spirophosphoranes containing a chiral phosphorus center with phenols[D]. Zhengzhou:Zhengzhou University(郑州大学), 2015.
[23]DaiWang(代旺).Researchesonthereactionsandmechanismsof bisamino hydrospirophosphoranes with allylic halides[D]. Zhengzhou:Zhengzhou University(郑州大学), 2016.
[24]WangWY,JinHA,YanZH,etal.Perfluoroalkanosulfonyl fluoride-assistedAtherton–Todd-likereactionofdiphenylphosphine oxidewithalcoholsunderairgeneratingdiphenylphosphinate esters[J]. Tetrahedron Letters, 2017, 58(36):3489-3492.
[25]Xu Kai(许凯). Palladium-catalyzed the coupling reaction involving dialkylH-phosphonateorterminalalkynes[D].Zhengzhou:Zhengzhou University(郑州大学), 2013.
[26]LuoSha(罗莎).ApplicationsofmetalcatalyzedC—Hbonds activation in the synthesis of pharmaceutically active units[D]. Wuxi:Jiangnan University(江南大学), 2014.
[27]Min Zehui(闵泽辉). Synthesis ofα-indole phosphonate ester based on CDC reaction[D]. Changsha:Hunan University(湖南大学), 2015.
[28]ZhangYun(张云).Studiesofcopper-catalyzeddecarboxylative coupling reaction ofα,β-unsaturated carboxylic acids with CF3CH2I Or HP(O)(OiPr)2[D]. Zhengzhou:Zhengzhou University(郑州大学),2017.
[29]YoshihiroS,NatsukoH,RikaT,etal.Enantioselectivephosphamichael reaction of diphenyl phosphonate with nitroolefins utilizing conformationallyflexibleguanidinium/bisthioureaorganocatalyst:assembly-state tunability inasymmetric organocatalysis[J].Advanced Synthesis&Catalysis, 2011, 353(14/15):2631-2636.
[30]Li G Y, Wang L, Yao Z G, et al. Chiral ytterbium silylamide catalyzed enantioselectivephospha-Michaeladditionofdiethylphosphiteto chalcones[J]. Tetrahedron:Asymmetry, 2014, 25(13/14):989-996.
[31]LuoYongyang(罗永阳).Directcatalyticasymmetricmichael addition reaction of dialkyl phosphites to 2-benzylidene-1-indanones byachiraldinuclearzinccatalyst[D].Zhengzhou:Zhengzhou University(郑州大学), 2017.
[32]KolodyazhnaAO;GrishkunEV,KolodyazhnyiOI.Synthesisof chiralphosphonobenzaldehydesandphosphonotyrosine[J].Russian Journal of General Chemistry,2017, 87:5.
[33]ZhaoYalei(赵亚磊).StudiesonthetransformationofP(O)—H bonds and its application in organic synthesis[D]. Changsha:Hunan University(湖南大学), 2015.
[34]LiuMingyu(刘明玉).Evaluationoftwoanimalmodelsof hyperuricemiabasedonlipidmetabolomics[D].Beijing:Beijing Univesity of Chinese Medicixe(北京中医药大学), 2018.
[35]Xie Xinqiang(谢新强). Phosphorothioate DNA as an antioxidant in bacteria[D].Shanghai:ShanghaiJiaoTongUniversity(上海交通大学), 2012.
[36]Zhao Yufen(赵玉芬), Li Yanmei(李艳梅). Phosphor chemistry and process of life chemistry[J]. Science and Technology Review(科技导报), 1994,(3):6-8.
[37]Dai Zhengqing(戴政清), Wang Yuen(王宇恩), Liu Jian(刘剑), et al. Progress on the synthesis of phosphopeptides by the Fmoc solidphasestrategy[J]. Chinese Journal of Medicinal Chemistry(中国药物化学杂志), 2011, 21(1):70-76.
[38]Wang Jingyan(王镜岩), Zhu Shenggeng(朱圣庚), Xu Changfa(徐长法).Biochemistry[M].Thirdedition.Beijing:HigherEducation Press(高等教育出版社), 2002:548.
[39]Mei Fangyi(梅方义), Cao Dong(曹栋). Preparation of a new kind ofmixedmicellebasedonphosphatidylcholineandnonionic surfactant[J]. Science and Technology of Food Industry(食品工业科技), 2011, 33(6):336-339.
[40]ZhangJun(张军),ZhanJiefang(詹结钫).Theperformanceand mechanismofemulsifieranditsapplicationincosmetic formulations[J]. Scientific and Technological Innovation(科学技术创新), 2018,(21):26-27.
[41]Zhang Wei(张玮), Wang Aijun(王爱军), Kou Yinke(寇寅客). On the synthesis of the vitamin C derivatives in cosmetic[J]. Journal of Shijiazhuang Vocational Technology Institute(石家庄职业技术学院学报), 2008, 20(2):11-13.
[42]Zhai Shaohua(翟少华), Jia Qinrui(贾钦瑞), Li Shuxian(李淑娴), et al. Microscopy and ultrastructure morphological study on skin tissue ofbullfrog[J].ChineseJournalofWildlife(野生动物学报),2018,39(1):105-109.
[43]ZhaoJuan(赵娟).Theapplicationresearchofautologousskin fibroblasts in medical cosmetology[D]. Changchun:Jilin University(吉林大学), 2007.
[44]Gu Renwan(顾仁碗), Zhang Hongzhi(张宏志). Aircraft corrosion and protection[J]. Science and Technology&Innovation(科技与创新), 2018,(12):68-70.
[45]An Haiming(安海明). Special-shaped tube cleaning and cleanliness testingtechnologyresearch[D].Shenyang:ShenyangAerospace University(沈阳航空航天大学), 2018.
[46]ZhangHongrui(张洪瑞).Designandsimulationofahigh cleanlinesscleaningeruipmentforairafttubes[D].Shenyang:Shenyang Aerospace University(沈阳航空航天大学), 2016.
[47]Shang Hufeng(商虎峰), Shi Baojun(师保俊), Zhang Huzhen(张祜珍),etal.Thedesignofaircraftpartscleaningproductionline automaticcontrolsystembasedonPLC[J].Manufacturing Automation(制造业自动化), 2018, 40(7):94-98.
[48]Liu Gengxin(刘庚鑫). A new material to improve the effectiveness andlongevityofmaterialcivilization—Ontheapplicationofnew technology of nano coating[J]. Total Corrosion Control(全面腐蚀控制), 2018, 32(7):1-5.
[49]Yang Yang(杨洋), Zhao Kui(赵奎), Zhu Hongbo(朱鸿博). Green chemistry-Anewconceptofchemistry[J].ChemicalEnterprise Management(化工管理), 2018,(14):17-18.
[50]Chen Xiaoping(陈小萍), Liu Junkang(刘俊康), Chen Yepu(陈烨璞),etal.Propertiesofnano-CaCO3modifiedbyaseriousof phosphatesurfactantsandtheirapplicationinPVC[J].Journalof Southern Yangtze University(Natural Science Edition)(江南大学学报:自然科学版), 2002,(3):266-268.
[51]Li Naishi(李乃师), Zhao Xudong(赵旭东), Fu Yanli(付彦丽), et al.Researchstatusandfuturedevelopmentoftertiaryoilrecovery technology[J]. Chemical Enterprise Management(化工管理), 2018,(18):121-122.
[52]LiYuan(李原).Studyonapplicationofaluminananofluidsin surfactantflooding[D].Chengdu:SouthwestPetroleumUniversity(西南石油大学), 2017.