硅氢加成反应合成KH-540的研究
|
摘要
有机硅化学是一门研究有机硅化合物的合成、结构、性能和用途的科学。有机硅化合物是除含C、N、O、P化合物以外研究最多的一种化合物,由其制得的有机硅材料,品种众多,性能优异,并已在工农业生产、新兴技术、国防军工、医疗卫生、食品等各种工业部门,已成为化工新材料中发展最快的品种之一
硅烷偶联剂是有机硅产品的一种,几种基本单体可生产出上千种有机硅产品,因此其本身可获得广泛应用。合成有硅烷偶联剂的重要反应-硅氢加成反应是有机硅化学中应用最广、研究最多的一个反应。目前工业上广泛使用的催化体系为铂的配合物和负载体,但是这些催化剂存在一些缺点,比如催化剂不稳定、易产生凝胶化物质、烯烃异构化严重等。
本论文研究了Pt-三乙胺络合物对于3-氨基丙烯与三甲氧基硅烷(TMOS)的硅氢加成一步合成γ-氨基丙基三甲氧基硅烷的合成,结果发现此种催化剂催化活性高、选择性强、催化剂使用量很低,具有很高的工业价值。利用气质连用定性分析了主、副产物的结构,利用气相色谱内标法监控反应过程并进行定量分析。本论文考察了反应温度、时间、催化剂用量、原料配比和初始压力等因素对硅氢加成反应的影响,结果表明在优化条件下,3-氨基丙烯的转化率可达87.9%,KH-540的选择性可达81.7%,产品无色透明且不容易产生高聚物。
Organosilicon is one of the most versatile groups of chemicals on the world, they can share some common features that give them special advantages over other materials. Organosilicon materials become the important branch of chemicals industry and hold a very important status in our country's economy. They are widely used in aerospace, electrical and electronic, textile, light industry, and other industrial sectors.
The catalytic hydrosilylation of unsaturated compounds is one of the most elegant methods for the synthesis of organosilicon compounds. Although the hydrosilylation of olefins predominantly uses platinum catalyst in industry at present, the deficiencies are obvious. All the drawbacks often resulted in undesired side reactions. To overcome some of these undesired side reactions, there has been a marked interest in the development of newer and different catalysts for the hydrosilylation reaction.
In this paper, Pt-triethylamine complexes were studied as catalysts for the one-pot synthesis of y-aminopropyltrimethoxysilane(KH-540) by hydrosilylation of 3-aminopropene with trimethoxysilane(TMOS). Pt-triethylamine complexes were proved to be active and effective homogeneous catalyst for the hydrosilylation reaction. GC-MS was used to analyze the structures of products qualitatively. The reaction course was monitored by GC, and the products were quantitatively analyzed using internal standard method. Effects of reaction temperature, reaction time, the amount of catalyst, n(TMOS):n(3-aminopropene) ratio, initial pressure on the hydrosilylation were investigated. Under the optimal conditions, the conversion of 3-aminopropene is 87.9%, the selectivity of KH-540 reaches 81.7% and no polymer is found during the whole reaction course of the hydrosilylation.
硅烷偶联剂是有机硅产品的一种,几种基本单体可生产出上千种有机硅产品,因此其本身可获得广泛应用。合成有硅烷偶联剂的重要反应-硅氢加成反应是有机硅化学中应用最广、研究最多的一个反应。目前工业上广泛使用的催化体系为铂的配合物和负载体,但是这些催化剂存在一些缺点,比如催化剂不稳定、易产生凝胶化物质、烯烃异构化严重等。
本论文研究了Pt-三乙胺络合物对于3-氨基丙烯与三甲氧基硅烷(TMOS)的硅氢加成一步合成γ-氨基丙基三甲氧基硅烷的合成,结果发现此种催化剂催化活性高、选择性强、催化剂使用量很低,具有很高的工业价值。利用气质连用定性分析了主、副产物的结构,利用气相色谱内标法监控反应过程并进行定量分析。本论文考察了反应温度、时间、催化剂用量、原料配比和初始压力等因素对硅氢加成反应的影响,结果表明在优化条件下,3-氨基丙烯的转化率可达87.9%,KH-540的选择性可达81.7%,产品无色透明且不容易产生高聚物。
Organosilicon is one of the most versatile groups of chemicals on the world, they can share some common features that give them special advantages over other materials. Organosilicon materials become the important branch of chemicals industry and hold a very important status in our country's economy. They are widely used in aerospace, electrical and electronic, textile, light industry, and other industrial sectors.
The catalytic hydrosilylation of unsaturated compounds is one of the most elegant methods for the synthesis of organosilicon compounds. Although the hydrosilylation of olefins predominantly uses platinum catalyst in industry at present, the deficiencies are obvious. All the drawbacks often resulted in undesired side reactions. To overcome some of these undesired side reactions, there has been a marked interest in the development of newer and different catalysts for the hydrosilylation reaction.
In this paper, Pt-triethylamine complexes were studied as catalysts for the one-pot synthesis of y-aminopropyltrimethoxysilane(KH-540) by hydrosilylation of 3-aminopropene with trimethoxysilane(TMOS). Pt-triethylamine complexes were proved to be active and effective homogeneous catalyst for the hydrosilylation reaction. GC-MS was used to analyze the structures of products qualitatively. The reaction course was monitored by GC, and the products were quantitatively analyzed using internal standard method. Effects of reaction temperature, reaction time, the amount of catalyst, n(TMOS):n(3-aminopropene) ratio, initial pressure on the hydrosilylation were investigated. Under the optimal conditions, the conversion of 3-aminopropene is 87.9%, the selectivity of KH-540 reaches 81.7% and no polymer is found during the whole reaction course of the hydrosilylation.
引文
[1]高红云,张招贵.硅烷偶联剂的偶联机理及研究现状[J].江西化工,2003,2：30-35.
[2]郭云亮,张涑戎,李立平,偶联剂的种类和特点及应用[J].橡胶工业,2003,50：692-697.
[3]幸松民,王一璐.有机硅合成工艺及产品应用[M].化学工业出版社,2000.
[4]CAPORUSSO A M, PANZIERA N, PERTICI P, et al. Hydrosilylation of aromatic nitriles promoted by solvated rhodium atom-derived catalysts [J]. Journal of Molecular Catalysis A:Chemical,1999,150(1-2):275-285.
[5]Marcin JANKOWIAK, Hieronim MACIEJEWSKI, Jacek GULINSKI. Catalytic reactions of hydrosiloxanes with ally chloride [J]. Journal of Organomethallic Chemistry, 2005,690:4478-4487.
[6]王晓会,马永欢,石万利等.缩水甘油醚氧三甲氧基硅烷的合成[J].石油化工,2008,37(6)：559-562.
[7]曾小剑,王传虎,葛金龙.γ-氯丙基二甲基氯硅烷的合成催化[J].有机硅材料,2009,23(2)：95-97.
[8]SOMMER L H, PIETRUSZA E W, WHITMORE F C. Peroxide-catalyzed addition of trichlorosilane to 1-octene [J]. Journal of the American Chemical Society,1947,69(1):188-188.
[9]MARCINIEC B. Catalysis of hydrosilylation of carbon-carbon multiple bonds:Recent progress [J]. Silicon Chemistry,2002,1:155-175.
[10]黄光佛,李盛彪,孙争光等.硅氢加成反应催化剂的研究进展[J].有机硅材料,2000,14(3)：11-14.
[11]萧斌,李凤仪,戴延凤.硅氢加成反应催化剂的研究进展[J].化工新型材料,2005,33(10)49-53.
[12]Larry N LEWIS, Richard J URIARTE. Hydrosilylation catalyzed by metal colloids:a relative activity study [J]. Organometallics,1990,9:621-625.
[13]HAMAO W, MASAFUMI A, NORITAKA S, et al. Selective synthesis of mono-alkyldichlorosilanes via the reaction of olefins eith dichlorosilane catalyzed by group Ⅷ metal phosphine complexes [J]. Journal of Organometallic Chemistry, 1978,160 (2):C1-C7.
[14]Constantinos A TSIPIS. Investigation of the factors controlling the regioselectivity of the hydrosilylation of alkynes catalysed by trans-di-μ-hydridobis(tricylcohexylphosphine)bis(silyl)diplatinum complexes [J]. Journal of Organometallic Chemistry,1980,187(3):427.
[15]SKVORTSOV N K, SPEVAK V N, PASHNOVA L V, et al. Synthesis of hydrosilylation platinium catalyst containing phosphine sulfide ligand [J]. Russian Journal of General Chemistry (Zhurnal Obshchei Khimii),1997,67(3):487-487.
[16]MIGNANI G, OSBORN J, STEFFANUT 0. Use of platinum complexes as homogeneous and heat-activable catalysts for hydrosilylation:WO,1998/000463[P].1998,08,01.
[17]FILIPKOWSKI M A. HERBERT P E. SCHILLING C L. et al. High purity organofunctional alkyldialkoxysilanes:US,6166238[P].2000,12,20.
[18]胡旭波,田珍桥,卢雪然等.1,3-双硫醚杯[4]芳烃铂络合物：一种新颖的硅氢加成催化剂[J].催化学报,1997,18(3)：187.
[19]CHEN Y Y, SHENG R S, LIU Y. (η-C60)Pt(PPh3)2 as the catalyst for the hydrosilylation of olefins [J]. Chemical Research in Chinese Universities,1994,10(4):338.
[20]YAO J Z. TIAN B S. CHEN Y Y.1,1-Bis (benzylseleno) ferrocene platinum complex as hydrosilylation catalyst for oledins [J]. Chinese Chemical Letters,1993, 4(7):601-602.
[21]张墩明,张宇峰.烯丙基硅(氧)烷铂配合物硅氢加成催化剂的研究[J].精细化工,2000，17(2)：82.
[22]MARKO I E, STERIN S, BUISINE 0, et al. Selective and efficient platinium(0)-carbene complexes as hydrosilylation catalysts [J]. Science,2002,298(5591):204-207.
[23]MARKO I E, STERIN S, BUISINE 0, et al. Highly active and selective platinum(0)-carbene complexes. Efficient, catalytic hydrosilylation of functionalised olefins [J]. Advanced Synthesis & Catalysis,2004,346(12):1429-1434.
[24]GUILLAUME B G, BUISINE 0, BRIERE J F. et al. Synthetic and structural studies of NHC-Pt(dvtms) complexes and their application as alkene hydrosilylation catalysts (NHC=N-heterocyclic carbine, dvtms=divinyltetramethylsiloxane) [J]. Journal of Organometallic Chemistry,2005,690(24-25),6156-6168.
[25]Olivier BUISINE, Guillaume Berthon GELLOZ, Jean Francois BRIERE, et al. Second generation N-heterocyclic carbene-Pt(0) complexes as efficient catalysts for the hydrosilylation of alkenes [J]. Chemical Communications,2005, (30),3856-3858.
[26]SPRENGERS J W, MARS M J, DUIN M A, et al. Selective hydrosilylation of styrene using an in situ formed platinum(1,3-dimesityl-dihydroimdazol-2-ylidene) catalyst [J]. Journal of Organometallic Chemistry,2003,697(2),149-152.
[27]王晓会,马永欢,侯洁等.Pt络合物催化合成γ-缩水甘油醚氧丙基三甲氧基硅烷[J].分子催化,2007,21(增刊)：201-202.
[28]龚小伦,曹威,罗成等.β-(3,4-环氧环己基)乙基三甲氧基硅烷的合成[J].有机硅材料,2010,24(1)：23-26.
[29]BAI Ying, PENG Jiajian, HU Yingqian, et al. Effect of Aminoaromatic Acids as Additives on the Activity and Selectivity of the Platinum-catalyzed Hydrosilylation of Alkenes [J].Chinese Journal of Chemical Engineering,2009,17(6)1038-1042.
[30]OJIMA I, FUCHIKMAI T, YATBAE M. The reactionsb of hydrosilanes with trifluoropropene And pentafluorostyrene catalyzed by ruthenium, rhodium and palladium complexes [J]. Journal of Orgnaometallic Chemistry,1984,260:335.
[31]CHALK A J. The hydrosilation of olefins eatalyzed by some rhodium and cobalt complexes [J]. Journal of Orgnaometallic Chemistry,1970,21:207.
[32]HAYASHI T, HAYASHI C, UOZUMI Y. Catalytic asymmetric hydrosilylation of ketones with new chiral ferrocenylphosphine-imine ligand [J]. Tetrahedron:Asymmetry,1995,6(10): 253-256.
[33]Tomasz GANICZA, Urszula MIZERSKA, Monika MOSZNER, et al. The effectiveness of rhodium (I), (II) and (III) complexes as catalysts in hydrosilylation of model olefin and polyether with triethoxysilane and poly(dimethylsiloxane-co-methylsiloxane) [J]. Applied Catalysis A:General,2004(259):49-55.
[34]Jia Jian PENG, Jia Yun LI, Ying BAI, et al. Rh(PPh3)3Cl/ionic liquid (molten salt) as a themoregulated and recyclable catalytic system for hydrosilylation [J]. Journal of Molecular Catalysis A:Chemical,2007(278):97-101.
[35]Chuan Wu, Jiajian PENG, Jiayun LI, et al. Synthesis of poly(ethylene glycol) (PEG) functionalized ionic liquids and the application to hydrosilylation [J]. Catalysis Communications,2008,10:248-250.
[36]厉嘉云,彭家建,胡应乾等.离子液体对Rh(PPh3)3Cl催化烯烃硅氢加成反应的影响[J].化学试剂,2009,31(7)：535-537.
[37]KITAYAMA K, UOZUMI Y, HAYASHI T. Palladium-catalyzed asymmetric hydrosilylation of styrenes with a new chiral monodentate phosphine ligand [J]. Chemical Communications, 1995, (15):1533-1534.
[38]WIDEENNHOEFER R A, DECARLI M A. Tandem cyclization/hydrosilylation of functionalized 1,6-dienes catalyzed by a cationic palladium complex [J]. Journal of the American Chemical Society,1998,120(15):3805-3806.
[39]KAWANMAI Y, YAMAMOTO K. Pd-catalyzed hydrosilylation of 1-alkynes with Concomitant dimerization to form 1,3-dienylsilanes [J]. Synlett,1995,12:1232.
[40]MAREINIEC B, GULINSKI J. Catalysis of Hydrosilylation Ⅶ Catalysis of hydorsilylation of C=C bonds by ruthenium phoshine complexes [J]. Journal of Organometallic Chemistry, 1983,253:349.
[41]TANAKA M, HAYASHI T, MI Z Y. Ruthenium complex-catalyzed hydrosilylation of allyl chloride with trimethoxysilane [J]. Journal of Molecular Catalysis,1993,81 (2):207-214.
[42]YOUNPIM N, SUKBOK C. Highly stereoselective and efficient hydrosilylation of terminal alkynes catalyzed by [RuCl2(p-cymene)]2 [J]. Organic Letters,2000,2(13):1887-1889.
[43]BARRY M T, ZACHARY T B. Markovnikov alkyne hydrosilylation catalyzed by ruthenium complexes [J]. Journal of the American Chemical Society,2001,123(50):12726-12727.
[44]KAWANAMI Y, SONODA Y, MORI T, et al. Ruthenium-catalyzed hydrosilylation of 1-alkynes with novel regioselectivity [J]. Organic Letters,2002,4(17):2825-2827.
[45]KUMADA M, KISO Y, UMENO M. Nickel(Ⅱ) complexes as catalysts in the hydrosilylation of olefins [J]. Chemical Communications,1970,10:611-616.
[46]YOSHIHISA K, MAKOTO K, KOHEI M, et al. Silicon hydrides and nickel complexes(I), Phosphine-nickel(Ⅱ) complexes as hydrosilylation catalysts [J]. Journal of Organometallic Chemistry,1973,50(1):297-310.
[47]娄兆文,张伦.单环戊二烯基镍化合物催化α-硅氢加成反应.分子催化[J],1994,8(6)：468-471.
[48]黄世强,孙争光,李盛彪等.铁系金属催化硅氢加成反应研究进展[J].化学通报1993,3：19-22.
[49]RANDOLPH C L, WRIGHTON M S. Photochemical reactions of (η5-pentamethylcyclopenta-dienyl) dicarbonyliron-alkyl and silyl complexes:Reversible ethylene insertion into an iron-silicon bond and implications for the mechanism of transition-metal-catalyzed hydrosilylation of alkenes [J]. Journal of the American Chemical Society,1986,108(12): 3366-3374.
[50]SUZANNE C B, EMIL L, CHIRIK P J. Preparation and molecular and electronic structure of iron(0) dinitrogen and silane complexes and their application to catalytic hydrogenation and hydrosilylation [J]. Journal of the American Chemical Society,2004, 126(42):13794-13807.
[51]MAGOMEDOV G K I, ANDRINAOV K A, SHKOLNIK 0 V, et al. Hydrosilylation of olefins in the presence of metal carbonyls [J]. Journal of orgnaometallic Chemistry,1978,149:29.
[52]WILEZEK L. Hydrosilation of fluorinated olefins with Cobalt Catalysts: US,5233071 [P].1993,08,03.
[53]ORO L A, FERNANDEZ M J, ESTERUELAS M A, et al. Hydrosilylation of alken by iridium complexes [J]. Jounral of Molecular Catalysis,1986,37:151.
[54]QUIRK J M, KANNER B. Novel proeess of the preparation of halopropyltrialkoxysilnaes and halopropyalkylalkoxysianes:US,4658050[P].1987,04,14.
[55]APPLE D C, BRADY K A, CHANCE J M, et al. Iridiun complexes as hydrosilylation catalysts [J]. Journal of Molecular Catalysis,1985,29:55.
[56]POLIZZI C, CAPORUSSO A M, VITULLI G, et al. Supported platinum atoms derived catalysts in the hydrosilylation of unsaturated substrates [J]. Journal of Molecular catalysis, 1994,91(1):83-90.
[57]CHAUHAN M, HAUCK B J, KELLER L P, et al. Hydrosilylation of alkynes catalyzed by platinum on carbon [J]. Journal of Organometallic Chemistry,2002,645(1-2):1-13.
[58]白赢,彭家建,厉嘉云等.Pt／C催化剂制备工艺对硅氢加成催化性能的影响[J].有机硅材料,2008,22(4)：194-197.
[59]MIAO Q J, FANG Z P, CAI G P. Silica-supported karstedt-type catalyst for hydrosilylation reactions [J]. Catalysis Communication,2003,4(12):637-639.
[60]DRAKE R, DUNN R, SHERRINGTON D C, et al. Remarkable activity, selectivity and stablility of polymer-supported Pt catalysts in room temperature, solvent-less, alkene hydrosilylations [J]. Chemical Communications,2000, (19):1931.
[61]陈远荫,卢雪然,王忠雨等.有机硅聚合物负载膦铂、膦锗络合物的合成及催化硅氢化性能[J].应用化学,1989,6(3)：1.
[62]刘京镐,史天义,胡春野等.应用高分子铂络合物催化合成硅烷偶联剂[J].高分子学报,1988,(4)：290.
[63]熊竹君,李凤仪,邓锋杰.硅氢加成反应催化机理的研究进展[J].有机硅材料,2006,20(6)：312-318.
[64]SPEIER J L, WEBSTER J A, BARNES G H. The addition of silicon hydrides to olefinic double bonds. part II. The use of group Ⅷ metal catalysts [J]. Journal of the American Chemical Society,1957,79(4):974-979.
[65]Marciniec B GULINSK. Recent advances in catalytic hydrosilylation [J]. Journal of Organometallic Chemistry,1993,446(1-2):15-23.
[66]SONG Y S, Y00 B R, LEE G H, et al. Lewis acid catalyzed region and stereoselective hydrosilylation of alkenes with trialkylsilanes [J]. Organometallics,1999,18(16): 3109-3115.
[67]HARROD J F, CHALK A J. Homogeneous catalysis. III. Isomerization of deuterio olefins by group Ⅷ metal complexes [J]. Journal of the American Chemical Society,1966,88(15): 3491-3497.
[68]SCHROEDER M A, WRIGHTON M S. Pentacarbonyliron(0) photocatalyzed reactions of trialkylsilanes with alkenes [J]. Journal of Organometallic Chemistry,1977,128(3): 345-358.
[69]LEWIS N. Platinum-catalyzed hydrosilation-colloid formation as the essential step [J]. Journal of the American Chemical Society,1986,108(23):7228-7231.
[70]LEWIS L N. On the mechanism of metal colloid catalyzed hydrosilation:proposed explanations for electronic effects and oxygen cocatalysis [J]. Journal of the American Chemical Society,1990,112(16):5998-6004.
[71]李瑞琦.氨基硅烷偶联剂[J].辽宁化工,2002,(314)：159-160.
[72]黄汉生.硅烷偶联剂及其应用技术动向[J].化工新材料,1995,11：23-27.
[73]John L SPEIER, C A ROTH, John W RYAN. Syntheses of (3-Aminoalkyl)silicon Compounds [J]. The Journal of Organic Chemistry,1971,36(21):3120-3126.
[74]Fritz Robert KAPPLER, Claus Dietrich SEILER, Hans Joachim VAHLENSIECK, et al. Method of preparing gamma aminopropylalkoxysilanes:US,4234503[P].1980,12,18.
[75]Toreten BALDUF, Stefan WIELAND, Wolfgang LORTZ. Continuous Method of Producing y-Aminopropyltrialkoxysilanes:US,5808123[P].1998,09,15.
[76]Roland KLEINSTUCK. Preparation of Aminoalkylsilanes:US,4045460[P].1977,08,30.
[77]Paul C DINH, Kenneeth P KAUFMAN. Process for Preparation of Primary Aminoorganosilanes: US,5117024[P].1992,05,26.
[78]Steven GEDON, Williamstown, Melinda HALE, et al. Process for Preparing Primary Aminoorganosilanes:US,6242627[P].2001,06,05.
[79]胡春野,赵东宇,江英彦.氯铂酸-三苯基膦体系催化硅氢加成反应的研究[J].催化学报,1989,10(2)：214-216.
[80]胡春野,杨荣华,江英彦.氯铂酸-三苯基膦体系催化硅氢加成反应的研究[J].分子催化,1988,2(1)：38-42.
[81]Nicolas SABOURAULT, Gerard MIGNANI, Alain WAGNER, et al. Platinum Oxide (PtO2):A Potent Hydrosilylation Catalyst [J]. Organic letters,2002,4(13):2117-2119.
[2]郭云亮,张涑戎,李立平,偶联剂的种类和特点及应用[J].橡胶工业,2003,50：692-697.
[3]幸松民,王一璐.有机硅合成工艺及产品应用[M].化学工业出版社,2000.
[4]CAPORUSSO A M, PANZIERA N, PERTICI P, et al. Hydrosilylation of aromatic nitriles promoted by solvated rhodium atom-derived catalysts [J]. Journal of Molecular Catalysis A:Chemical,1999,150(1-2):275-285.
[5]Marcin JANKOWIAK, Hieronim MACIEJEWSKI, Jacek GULINSKI. Catalytic reactions of hydrosiloxanes with ally chloride [J]. Journal of Organomethallic Chemistry, 2005,690:4478-4487.
[6]王晓会,马永欢,石万利等.缩水甘油醚氧三甲氧基硅烷的合成[J].石油化工,2008,37(6)：559-562.
[7]曾小剑,王传虎,葛金龙.γ-氯丙基二甲基氯硅烷的合成催化[J].有机硅材料,2009,23(2)：95-97.
[8]SOMMER L H, PIETRUSZA E W, WHITMORE F C. Peroxide-catalyzed addition of trichlorosilane to 1-octene [J]. Journal of the American Chemical Society,1947,69(1):188-188.
[9]MARCINIEC B. Catalysis of hydrosilylation of carbon-carbon multiple bonds:Recent progress [J]. Silicon Chemistry,2002,1:155-175.
[10]黄光佛,李盛彪,孙争光等.硅氢加成反应催化剂的研究进展[J].有机硅材料,2000,14(3)：11-14.
[11]萧斌,李凤仪,戴延凤.硅氢加成反应催化剂的研究进展[J].化工新型材料,2005,33(10)49-53.
[12]Larry N LEWIS, Richard J URIARTE. Hydrosilylation catalyzed by metal colloids:a relative activity study [J]. Organometallics,1990,9:621-625.
[13]HAMAO W, MASAFUMI A, NORITAKA S, et al. Selective synthesis of mono-alkyldichlorosilanes via the reaction of olefins eith dichlorosilane catalyzed by group Ⅷ metal phosphine complexes [J]. Journal of Organometallic Chemistry, 1978,160 (2):C1-C7.
[14]Constantinos A TSIPIS. Investigation of the factors controlling the regioselectivity of the hydrosilylation of alkynes catalysed by trans-di-μ-hydridobis(tricylcohexylphosphine)bis(silyl)diplatinum complexes [J]. Journal of Organometallic Chemistry,1980,187(3):427.
[15]SKVORTSOV N K, SPEVAK V N, PASHNOVA L V, et al. Synthesis of hydrosilylation platinium catalyst containing phosphine sulfide ligand [J]. Russian Journal of General Chemistry (Zhurnal Obshchei Khimii),1997,67(3):487-487.
[16]MIGNANI G, OSBORN J, STEFFANUT 0. Use of platinum complexes as homogeneous and heat-activable catalysts for hydrosilylation:WO,1998/000463[P].1998,08,01.
[17]FILIPKOWSKI M A. HERBERT P E. SCHILLING C L. et al. High purity organofunctional alkyldialkoxysilanes:US,6166238[P].2000,12,20.
[18]胡旭波,田珍桥,卢雪然等.1,3-双硫醚杯[4]芳烃铂络合物：一种新颖的硅氢加成催化剂[J].催化学报,1997,18(3)：187.
[19]CHEN Y Y, SHENG R S, LIU Y. (η-C60)Pt(PPh3)2 as the catalyst for the hydrosilylation of olefins [J]. Chemical Research in Chinese Universities,1994,10(4):338.
[20]YAO J Z. TIAN B S. CHEN Y Y.1,1-Bis (benzylseleno) ferrocene platinum complex as hydrosilylation catalyst for oledins [J]. Chinese Chemical Letters,1993, 4(7):601-602.
[21]张墩明,张宇峰.烯丙基硅(氧)烷铂配合物硅氢加成催化剂的研究[J].精细化工,2000，17(2)：82.
[22]MARKO I E, STERIN S, BUISINE 0, et al. Selective and efficient platinium(0)-carbene complexes as hydrosilylation catalysts [J]. Science,2002,298(5591):204-207.
[23]MARKO I E, STERIN S, BUISINE 0, et al. Highly active and selective platinum(0)-carbene complexes. Efficient, catalytic hydrosilylation of functionalised olefins [J]. Advanced Synthesis & Catalysis,2004,346(12):1429-1434.
[24]GUILLAUME B G, BUISINE 0, BRIERE J F. et al. Synthetic and structural studies of NHC-Pt(dvtms) complexes and their application as alkene hydrosilylation catalysts (NHC=N-heterocyclic carbine, dvtms=divinyltetramethylsiloxane) [J]. Journal of Organometallic Chemistry,2005,690(24-25),6156-6168.
[25]Olivier BUISINE, Guillaume Berthon GELLOZ, Jean Francois BRIERE, et al. Second generation N-heterocyclic carbene-Pt(0) complexes as efficient catalysts for the hydrosilylation of alkenes [J]. Chemical Communications,2005, (30),3856-3858.
[26]SPRENGERS J W, MARS M J, DUIN M A, et al. Selective hydrosilylation of styrene using an in situ formed platinum(1,3-dimesityl-dihydroimdazol-2-ylidene) catalyst [J]. Journal of Organometallic Chemistry,2003,697(2),149-152.
[27]王晓会,马永欢,侯洁等.Pt络合物催化合成γ-缩水甘油醚氧丙基三甲氧基硅烷[J].分子催化,2007,21(增刊)：201-202.
[28]龚小伦,曹威,罗成等.β-(3,4-环氧环己基)乙基三甲氧基硅烷的合成[J].有机硅材料,2010,24(1)：23-26.
[29]BAI Ying, PENG Jiajian, HU Yingqian, et al. Effect of Aminoaromatic Acids as Additives on the Activity and Selectivity of the Platinum-catalyzed Hydrosilylation of Alkenes [J].Chinese Journal of Chemical Engineering,2009,17(6)1038-1042.
[30]OJIMA I, FUCHIKMAI T, YATBAE M. The reactionsb of hydrosilanes with trifluoropropene And pentafluorostyrene catalyzed by ruthenium, rhodium and palladium complexes [J]. Journal of Orgnaometallic Chemistry,1984,260:335.
[31]CHALK A J. The hydrosilation of olefins eatalyzed by some rhodium and cobalt complexes [J]. Journal of Orgnaometallic Chemistry,1970,21:207.
[32]HAYASHI T, HAYASHI C, UOZUMI Y. Catalytic asymmetric hydrosilylation of ketones with new chiral ferrocenylphosphine-imine ligand [J]. Tetrahedron:Asymmetry,1995,6(10): 253-256.
[33]Tomasz GANICZA, Urszula MIZERSKA, Monika MOSZNER, et al. The effectiveness of rhodium (I), (II) and (III) complexes as catalysts in hydrosilylation of model olefin and polyether with triethoxysilane and poly(dimethylsiloxane-co-methylsiloxane) [J]. Applied Catalysis A:General,2004(259):49-55.
[34]Jia Jian PENG, Jia Yun LI, Ying BAI, et al. Rh(PPh3)3Cl/ionic liquid (molten salt) as a themoregulated and recyclable catalytic system for hydrosilylation [J]. Journal of Molecular Catalysis A:Chemical,2007(278):97-101.
[35]Chuan Wu, Jiajian PENG, Jiayun LI, et al. Synthesis of poly(ethylene glycol) (PEG) functionalized ionic liquids and the application to hydrosilylation [J]. Catalysis Communications,2008,10:248-250.
[36]厉嘉云,彭家建,胡应乾等.离子液体对Rh(PPh3)3Cl催化烯烃硅氢加成反应的影响[J].化学试剂,2009,31(7)：535-537.
[37]KITAYAMA K, UOZUMI Y, HAYASHI T. Palladium-catalyzed asymmetric hydrosilylation of styrenes with a new chiral monodentate phosphine ligand [J]. Chemical Communications, 1995, (15):1533-1534.
[38]WIDEENNHOEFER R A, DECARLI M A. Tandem cyclization/hydrosilylation of functionalized 1,6-dienes catalyzed by a cationic palladium complex [J]. Journal of the American Chemical Society,1998,120(15):3805-3806.
[39]KAWANMAI Y, YAMAMOTO K. Pd-catalyzed hydrosilylation of 1-alkynes with Concomitant dimerization to form 1,3-dienylsilanes [J]. Synlett,1995,12:1232.
[40]MAREINIEC B, GULINSKI J. Catalysis of Hydrosilylation Ⅶ Catalysis of hydorsilylation of C=C bonds by ruthenium phoshine complexes [J]. Journal of Organometallic Chemistry, 1983,253:349.
[41]TANAKA M, HAYASHI T, MI Z Y. Ruthenium complex-catalyzed hydrosilylation of allyl chloride with trimethoxysilane [J]. Journal of Molecular Catalysis,1993,81 (2):207-214.
[42]YOUNPIM N, SUKBOK C. Highly stereoselective and efficient hydrosilylation of terminal alkynes catalyzed by [RuCl2(p-cymene)]2 [J]. Organic Letters,2000,2(13):1887-1889.
[43]BARRY M T, ZACHARY T B. Markovnikov alkyne hydrosilylation catalyzed by ruthenium complexes [J]. Journal of the American Chemical Society,2001,123(50):12726-12727.
[44]KAWANAMI Y, SONODA Y, MORI T, et al. Ruthenium-catalyzed hydrosilylation of 1-alkynes with novel regioselectivity [J]. Organic Letters,2002,4(17):2825-2827.
[45]KUMADA M, KISO Y, UMENO M. Nickel(Ⅱ) complexes as catalysts in the hydrosilylation of olefins [J]. Chemical Communications,1970,10:611-616.
[46]YOSHIHISA K, MAKOTO K, KOHEI M, et al. Silicon hydrides and nickel complexes(I), Phosphine-nickel(Ⅱ) complexes as hydrosilylation catalysts [J]. Journal of Organometallic Chemistry,1973,50(1):297-310.
[47]娄兆文,张伦.单环戊二烯基镍化合物催化α-硅氢加成反应.分子催化[J],1994,8(6)：468-471.
[48]黄世强,孙争光,李盛彪等.铁系金属催化硅氢加成反应研究进展[J].化学通报1993,3：19-22.
[49]RANDOLPH C L, WRIGHTON M S. Photochemical reactions of (η5-pentamethylcyclopenta-dienyl) dicarbonyliron-alkyl and silyl complexes:Reversible ethylene insertion into an iron-silicon bond and implications for the mechanism of transition-metal-catalyzed hydrosilylation of alkenes [J]. Journal of the American Chemical Society,1986,108(12): 3366-3374.
[50]SUZANNE C B, EMIL L, CHIRIK P J. Preparation and molecular and electronic structure of iron(0) dinitrogen and silane complexes and their application to catalytic hydrogenation and hydrosilylation [J]. Journal of the American Chemical Society,2004, 126(42):13794-13807.
[51]MAGOMEDOV G K I, ANDRINAOV K A, SHKOLNIK 0 V, et al. Hydrosilylation of olefins in the presence of metal carbonyls [J]. Journal of orgnaometallic Chemistry,1978,149:29.
[52]WILEZEK L. Hydrosilation of fluorinated olefins with Cobalt Catalysts: US,5233071 [P].1993,08,03.
[53]ORO L A, FERNANDEZ M J, ESTERUELAS M A, et al. Hydrosilylation of alken by iridium complexes [J]. Jounral of Molecular Catalysis,1986,37:151.
[54]QUIRK J M, KANNER B. Novel proeess of the preparation of halopropyltrialkoxysilnaes and halopropyalkylalkoxysianes:US,4658050[P].1987,04,14.
[55]APPLE D C, BRADY K A, CHANCE J M, et al. Iridiun complexes as hydrosilylation catalysts [J]. Journal of Molecular Catalysis,1985,29:55.
[56]POLIZZI C, CAPORUSSO A M, VITULLI G, et al. Supported platinum atoms derived catalysts in the hydrosilylation of unsaturated substrates [J]. Journal of Molecular catalysis, 1994,91(1):83-90.
[57]CHAUHAN M, HAUCK B J, KELLER L P, et al. Hydrosilylation of alkynes catalyzed by platinum on carbon [J]. Journal of Organometallic Chemistry,2002,645(1-2):1-13.
[58]白赢,彭家建,厉嘉云等.Pt／C催化剂制备工艺对硅氢加成催化性能的影响[J].有机硅材料,2008,22(4)：194-197.
[59]MIAO Q J, FANG Z P, CAI G P. Silica-supported karstedt-type catalyst for hydrosilylation reactions [J]. Catalysis Communication,2003,4(12):637-639.
[60]DRAKE R, DUNN R, SHERRINGTON D C, et al. Remarkable activity, selectivity and stablility of polymer-supported Pt catalysts in room temperature, solvent-less, alkene hydrosilylations [J]. Chemical Communications,2000, (19):1931.
[61]陈远荫,卢雪然,王忠雨等.有机硅聚合物负载膦铂、膦锗络合物的合成及催化硅氢化性能[J].应用化学,1989,6(3)：1.
[62]刘京镐,史天义,胡春野等.应用高分子铂络合物催化合成硅烷偶联剂[J].高分子学报,1988,(4)：290.
[63]熊竹君,李凤仪,邓锋杰.硅氢加成反应催化机理的研究进展[J].有机硅材料,2006,20(6)：312-318.
[64]SPEIER J L, WEBSTER J A, BARNES G H. The addition of silicon hydrides to olefinic double bonds. part II. The use of group Ⅷ metal catalysts [J]. Journal of the American Chemical Society,1957,79(4):974-979.
[65]Marciniec B GULINSK. Recent advances in catalytic hydrosilylation [J]. Journal of Organometallic Chemistry,1993,446(1-2):15-23.
[66]SONG Y S, Y00 B R, LEE G H, et al. Lewis acid catalyzed region and stereoselective hydrosilylation of alkenes with trialkylsilanes [J]. Organometallics,1999,18(16): 3109-3115.
[67]HARROD J F, CHALK A J. Homogeneous catalysis. III. Isomerization of deuterio olefins by group Ⅷ metal complexes [J]. Journal of the American Chemical Society,1966,88(15): 3491-3497.
[68]SCHROEDER M A, WRIGHTON M S. Pentacarbonyliron(0) photocatalyzed reactions of trialkylsilanes with alkenes [J]. Journal of Organometallic Chemistry,1977,128(3): 345-358.
[69]LEWIS N. Platinum-catalyzed hydrosilation-colloid formation as the essential step [J]. Journal of the American Chemical Society,1986,108(23):7228-7231.
[70]LEWIS L N. On the mechanism of metal colloid catalyzed hydrosilation:proposed explanations for electronic effects and oxygen cocatalysis [J]. Journal of the American Chemical Society,1990,112(16):5998-6004.
[71]李瑞琦.氨基硅烷偶联剂[J].辽宁化工,2002,(314)：159-160.
[72]黄汉生.硅烷偶联剂及其应用技术动向[J].化工新材料,1995,11：23-27.
[73]John L SPEIER, C A ROTH, John W RYAN. Syntheses of (3-Aminoalkyl)silicon Compounds [J]. The Journal of Organic Chemistry,1971,36(21):3120-3126.
[74]Fritz Robert KAPPLER, Claus Dietrich SEILER, Hans Joachim VAHLENSIECK, et al. Method of preparing gamma aminopropylalkoxysilanes:US,4234503[P].1980,12,18.
[75]Toreten BALDUF, Stefan WIELAND, Wolfgang LORTZ. Continuous Method of Producing y-Aminopropyltrialkoxysilanes:US,5808123[P].1998,09,15.
[76]Roland KLEINSTUCK. Preparation of Aminoalkylsilanes:US,4045460[P].1977,08,30.
[77]Paul C DINH, Kenneeth P KAUFMAN. Process for Preparation of Primary Aminoorganosilanes: US,5117024[P].1992,05,26.
[78]Steven GEDON, Williamstown, Melinda HALE, et al. Process for Preparing Primary Aminoorganosilanes:US,6242627[P].2001,06,05.
[79]胡春野,赵东宇,江英彦.氯铂酸-三苯基膦体系催化硅氢加成反应的研究[J].催化学报,1989,10(2)：214-216.
[80]胡春野,杨荣华,江英彦.氯铂酸-三苯基膦体系催化硅氢加成反应的研究[J].分子催化,1988,2(1)：38-42.
[81]Nicolas SABOURAULT, Gerard MIGNANI, Alain WAGNER, et al. Platinum Oxide (PtO2):A Potent Hydrosilylation Catalyst [J]. Organic letters,2002,4(13):2117-2119.