铂催化硅氢加成反应研究进展

doi:10.16085/j.issn.1000-6613.2019-0958

摘要/Abstract

摘要：

硅氢加成反应是合成有机硅材料最重要的途径之一，铂催化剂作为其应用最广的催化剂，具有重要的意义。本文首先介绍了硅氢加成反应机理的研究现状；分析了聚合物长链段铂配合物、含多个铂原子铂簇化合物及N-杂环卡宾铂配合物均相铂催化剂的研究进展，致力于改善均相催化剂催化选择性差、催化活性难以控制等缺点；分别阐述了不同铂催化剂载体如无机二氧化硅、炭载体、金属氧化物、有机高分子、固载液等作为铂催化剂载体的优点，负载铂催化剂具有可回收、产物选择性好的优点，有效解决了工业上铂损失的问题；最后对铂催化硅氢加成反应的发展趋势进行了展望分析，铂负载能力的提高、铂负载催化剂的分离、硅氢加成反应的原理、催化范围的扩大等均是今后研究的重要方向。

关键词: 催化剂, 催化剂载体, 活性, 选择性, 铂, 硅氢加成反应

Abstract:

Hydrosilylation is one of the most important ways to synthesize organosilicon materials. Platinum catalyst is of great significance as it is the most widely used catalyst. In this review, the research status of hydrosilylation reaction mechanism was first presented. Secondly, this paper analyzed the progress in platinum complex catalysts with long polymer segments, platinum cluster catalysts containing multiple platinum atoms andN-heterocyclic carbene platinum complexes catalysts, which were mainly designed to improve the catalytic selectivity and control the catalytic reactivity. In addition, the advantages of the supports for platinum catalysts such as inorganic silica, carbon support, metal oxides, organic polymers, and solid carrier fluids were reported. The supported platinum catalysts have the advantages of being recyclable and having good product selectivity and thus could significantly reduce platinum loss in comparison to the homogeneous platinum catalyst. Meantime, the development of platinum-catalysed hydrosilylation reaction was prospected and analysed. The improvement of platinum loading capacity, the separation of platinum-supported catalysts, the mechanism of hydrosilylation reaction, and the expansion of catalytic range are the main directions for future research.

Key words: catalyst, catalyst support, reactivity, selectivity, platinum, hydrosilylation reaction

中图分类号:

TQ426.8

柯其宁,代志鹏,陈琛,陈绪煌. 铂催化硅氢加成反应研究进展[J]. 化工进展, 2020, 39(3): 992-999.

Qining KE,Zhipeng DAI,Chen CHEN,Xuhuang CHEN. Progress in platinum-catalyzed hydrosilylation reaction[J]. Chemical Industry and Engineering Progress, 2020, 39(3): 992-999.

图/表 12

图1 过渡金属催化硅氢加成Chalk-Harrod机理[10]

图2 胶体铂机理图[11]

图3 Pt3簇化合物催化剂[12]

图4 铂-乙炔基络合物的机械反应性聚合物的合成[17]

图5 Pt/AC催化硅氢加成反应[3]

图6 不同负载下硅氢加成反应转换率[28]

图7 GO-Karstedt催化剂的合成[33]

图8 Pt-GNP催化烯烃加成反应[34]

图9 Pt-ISA/NG催化剂的结构示意图[36]

图10 Pt1δ+/TiO2合成过程[42]

图11 交联聚硅氧烷负载Pt纳米催化剂的合成[44]

图12 纳米铂固载液催化剂的制备[49]

参考文献 53

1	SOMMER L H,PIETRUSZA E W,WHITMORE F C.Peroxide catalyzed addition of trichlorosilane to 1-octene[J].Journal of the American Chemical Society,1947,69:188-191.
2	SPEIER J L.Homogeneous catalysis of hydrosilation by transition metals[J].Advances in Organometallic Chemistry,1979,17:407-447.
3	WAGNER G H.Reaction of silanes with aliphatic unsaturated compounds:US2637738[P].1953-05-05.
4	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):574-580.
5	KARSTEDT B.Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes:US3775452[P].1973-11-27.
6	PANDARUS V,CIRIMINNA R,GINGRAS G,et al.Waste-free and efficient hydrosilylation of olefins[J].Green Chemistry,2019,21(1):129-140.
7	WENG Z H,ZAERA F.Sub-monolayer control of mixed-oxide support composition in catalystsvia atomic layer deposition: selective hydrogenation of cinnamaldehyde promoted by (SiO₂ALD)-Pt/Al₂O₃[J].ACS Catalysis,2018,8:8513-8524.
8	DARIUSZ B,MONIKA R,BEATA D.Regioselective formation ofβ-(E) andα-alkenylsilane moiety attached to silsesquioxane corevia Pt- and Ru-based hydrosilylation[J].Applied Organometallic Chemistry,2018,32(4):e4267.
9	CHEN Z,CHEN J,LI Y.Metal-organic-framework-based catalysts for hydrogenation reactions[J].Chinese Journal of Catalysis,2017,38(7):1108-1126.
10	CHALK A J,HARROD J F.Homogeneous catalysis Ⅱ. The mechanism of the hydrosilation of olefins catalyzed by group Ⅷ metal complexes[J].Journal of the American Chemical Society,1965,87:16-21.
11	SAKAKI S,MIZOE N,SUGIMOTO M.Theoretical study of platinum(0)-catalyzed hydrosilylation of ethylene. Chalk-Harrod mechanism or modified Chalk-Harrod mechanism[J].Organometallics,1998,17(12):2510-2523.
12	CORMA A,LEYVA A,RIVERO A M.A ligand-free Pt₃ cluster catalyses the markovnikov hydrosilylation of alkynes with up to 10⁶ turnover frequencies[J].Chemistry,2017,23(7):1702-1708.
13	ZAK P,BOLT M,PIETRASZUK C.Highly selective hydrosilylation of olefins and acetylenes by platinum(0) complexes bearing bulkyN-heterocyclic carbene ligands[J].Dalton transactions,2018,47(6):1903-1910.
14	鲁鸿,刘金宇,李红玉,等.氮杂环卡宾与过渡金属共催化反应研究进展[J].化学学报,2018,76(11):831-837.
	LU H,LIU J Y,LI H Y,et al.Recent developments inN-heterocyclic carbene and transition-metal cooperative catalysis[J].Acta Chimica Sinica,2018,76(11):831-837.
15	张凤香,白赢,杨晓玲,等.N-杂环卡宾铂配合物的合成及其在有机反应中的应用[J].化学进展,2017,29(4):412-425.
	ZHANG F X,BAI Y,YANG X L,et al.Synthesis ofN-heterocyclic carbene platinum complexes and application in the organic reaction[J].Progress in Chemistry,2017,29(4):412-425.
16	ZHANG F X,BAI Y,YANG X L,et al.N-heterocyclic carbene platinum complexes functionalized with a polyether chain and silyl group: synthesis and application as a catalyst for hydrosilylation[J].Phosphorus,Sulfur, andSilicon and the Related Elements,2017,192(12):1271-1278.
17	WEI K,GAO Z C,LIU H R,et al.Mechanical activation of platinum-acetylide complex for olefin hydrosilylation[J].ACS Macro Letters,2017,6(10):1146-1150.
18	邓锋杰,徐少华,温远庆,等.4A分子筛固载铂催化剂催化乙炔硅氢加成反应[J].化工进展,2008,27(1):112-115.
	DENG F J,XU S H,WEN Y Q,et al.4A zeolite supported platinum catalyst for hydrosilylation of acetylene[J].Chemical Industry and Engineering Progress,2008,27(1):112-115.
19	HOFMANN R J,VLATKOVI M,WIESBROCK F.Fifty years of hydrosilylation in polymer science: a review of current trends of low-cost transition-metal and metal-free catalysts, non-thermally triggered hydrosilylation reactions, and industrial applications[J].Polymers,2017,9(10):1-37.
20	邵冬云,李优鑫.催化硅氢加成反应负载型铂催化剂的研究进展[J].现代化工,2018,38(4):13-17.
	SHAO D Y,LI Y X.Research progress of supported platinum catalysts for hydrosilylation[J].Modern Chemistry Industry,2018,38(4):13-17.
21	XIE H L,YUE H B,ZHANG W X,et al.A chitosan modified Pt/SiO₂ catalyst for the synthesis of 3-poly(ethylene glycol) propyl ether-heptamethyltrisiloxane applied as agricultural synergistic agent[J].Catalysis Communications,2018,104:118-122.
22	SHAO D Y,LI Y X.Preparation of polycarboxylic acid-functionalized silica supported Pt catalysts and their applications in alkene hydrosilylation[J].RSC Advances,2018,8(36):20379-20393.
23	DUKE B J,AKEROYD E N,BHATT S V.Nano-dispersed platinum(0) in organically modified silicate matrices as sustainable catalysts for a regioselective hydrosilylation of alkenes and alkynes[J].New Journal of Chemistry,2018,42(14):11782-11795.
24	LI F T,LI Y X.Preparation of efficient and environment-friendly silica-supported EDTA platinum catalyst and its applications in hydrosilylation of olefins and methyldichlorosilane[J].Journal of Molecular Catalysis A: Chemical,2016,420:254-263.
25	BAI Y,PENG J J,LI J Y,et al.Functionalized silica immobilized platinum catalyst and its application in the catalytic hydrosilylation of alkenes[J].Current Catalysis,2012,1:180-185.
26	HU W B,XIE H L,PRINSEN P,et al.Super-microporous silica-supported platinum catalyst for highly regioselective hydrosilylation[J].Catalysis Communications,2017,97:51-55.
27	DONG C,YUAN Y,CUI Y M,et al.A pronounced ligand effect on platinum-catalyzed hydrosilylation of terminal alkynes[J].Applied Organometallic Chemistry,2018,32(2) :e4037.
28	DOROKHOV V G,DOROKHOVA G F,SAVCHENKO V I.Study of the products of platinum-catalyzed hydrogenation of chlorinatednitro and amino aromatic compounds at high degree of dehalogenation[J].Russian Chemical Bulletin,2018,67(8):1412-1418.
29	刘玉荣.碳材料在超级电容器中的应用[M].北京:国防工业出版社,2013:211-237.
	LIU Y R.Carbon materials for supercapacitor application[M].Beijing:National Defence Industry Press,2013:211-237.
30	ZHANG P,SUN D R,CHO A,et al.Modified carbon nitride nanozyme as bifunctional glucose oxidase-peroxidase for metal-free bioinspired cascade photocatalysis[J].Nature Communications,2019,10(1):940-953.
31	DONGIL A B,BACHILLER-BAEZA B,GUERRERO-RUIZ A,et al.Graphite oxide as support for the immobilization of Ru-BINAP: application in the enantioselective hydrogenation of methylacetoacetate[J].Catalysis Communications,2012,26:149-154.
32	ZHAO Y F,ZHANG H Y,HUANG C L,et al.Pd nanoparticles immobilized on graphite oxide modified with a base: highly efficient catalysts for selective hydrogenation of citral[J].China Chemistry,2013,56(2):203-209.
33	RAO F Y,DENG S J,CHEN C,et al.Graphite oxide-supported Karstedt catalyst for the hydrosilylation of olefins with triethoxysilane[J].Catalysis Communications,2014,46:1-5.
34	KONG C J,GILLILAND III S E,CLARK B R,et al.Highly-active, graphene-supported platinum catalyst for the solventless hydrosilylation of olefins[J].Chemical Communications,2018,54(95):13343-13346.
35	ZHU Y Q,CAO T,CAO C B,et al.A general synthetic strategy to monolayer graphene[J].Nano Research,2018,11(6):3088-3095.
36	ZHU Y Q,CAO T,CAO C B,et al.One-pot pyrolysis to N-doped graphene with high-density Pt single atomic sites as heterogeneous catalyst for alkene hydrosilylation[J].ACS Catalysis,2018,8(11):10004-10011.
37	CIRIMINNA R,PANDARUS V,GINGRAS G,et al.Closing the organosilicon synthetic cycle: efficient heterogeneous hydrosilylation of alkenes over siliacat Pt (0)[J].ACS Sustainable Chem. Eng.,2013,1(2):249-253.
38	CUI X,JUNGE K,DAI X,et al.Synthesis of single atom based heterogeneous platinum catalysts: high selectivity and activity for hydrosilylation reactions[J].ACS Central Science,2017,3(6):580-585.
39	TSUCHIDO Y,ABE R,KAMONO M,et al.Hydrosilylation of aromatic aldehydes and ketones catalyzed by mono- and tri-nuclear platinum(0) complexes[J].Bulletin of the Chemical Society of Japan,2018,91(5):858-864.
40	JENNIFER V O,PAUL J C.Earth-abundant transition metal catalysts for alkene hydrosilylation and hydroboration: opportunities and assessments[J].Nature Reviews: Chemistry,2018,2(5):15-34.
41	LU K,HU Z,XIANG Z,et al.Cation intercalation in manganese oxide nanosheets: effects on lithium and sodium storage[J].Angewandte Chemie,2016,55(35):10448-10452.
42	CHEN Y J,JI S F,SUN W M,et al.Discovering partially charged single-atom Pt for enhanced antimarkovnikov alkene hydrosilylation[J].Journal of the American Chemical Society,2018,140(24):7407-7410.
43	MICHALSKA Z M,STRZELEC K,SOBCZAK J W.Hydrosilylation of phenylacetylene catalyzed by metal complex catalysts supported on polyamides containing a pyridine moiety[J].Journal of Molecular Catalysis A: Chemical,2000,156(1):91-102.
44	CHAUHAN B P S,SARKAR A.Functionalized vinylsilanesviahighly efficient and recyclable Pt-nanoparticle catalysed hydrosilylation of alkynes[J].Dalton Transactions,2017,46(27):8709-8715.
45	谢志凯,陈秀莹,胡文斌,等.功能化金属有机骨架负载铂高效催化硅氢加成反应[J].分子催化,2018,32(6):520-529.
	XIE Z K,CHEN X Y,HU W B,et al.Functionalized metal-organic framework supported platinum highly efficient catalytic hydrosilylation[J].Journal of Molecular Catalysis,2018,32(6):520-529.
46	QIAO Y,MA W,THEYSSEN N,et al.Temperature-responsive ionic liquids: fundamental behaviors and catalytic applications[J].Chemical Reviews,2017,117(10):6881-6928.
47	WELTON T.Ionic liquids: a brief history[J].Biophysical Reviews,2018,10(3):691-706.
48	MAGDALENA J W,IZABELA D,RYSZARD F,et al.The effect of the morpholinium ionic liquid anion on the catalytic activity of Rh (or Pt) complex-ionic liquid systems in hydrosilylation processes[J].RSC Advances,2018,8(47):26922-26927.
49	FERNÁNDEZ G,PLEIXATS R.Soluble Pt nanoparticles stabilized by atris-imidazolium tetrafluoroborate as efficient and recyclable catalyst for the stereoselective hydrosilylation of alkynes[J].Chemistry Select,2018,3(41):11486-11493.
50	刘国旺.含氢硅烷的硅氢加成反应及其催化剂负载化研究[D].杭州：浙江大学,2010.
	LIU G W.Hydrosilylation of hydrosilanes and the synthesis of Pt catalyst supported on HNTs[D].Hangzhou:Zhejiang University,2010.
51	陈伟,闫婉婉,胡庆华.SBA-15微球负载Karstedt催化剂制备及对硅氢加成反应动力学[J].硅酸盐学报,2016,44(3):419-424.
	CHEN W,YAN W W,HU Q H.Preparation of SBA-15 supported Karstedt catalysts and catalytic kinetics on hydrosilylation[J].Journal of the Chinese Ceramic Society,2016,44(3):419-424.
52	ROSSI L M,COSTA N J S,SILVA F P,et al.Magnetic nanomaterials in catalysis: advanced catalysts for magnetic separation and beyond[J].Green Chemistry,2014,16(6):2906-2933.
53	ZAI H C,ZHAO Y Z,CHEN S Y.A novel hierachically-nanostructured Pt/SiO₂/Fe₃O₄ catalyst with high activity and recyclability towards hydrosilylation[J].RSC Advance,2016,6(100):98520-98527.

[1]	张明焱, 刘燕, 张雪婷, 刘亚科, 李从举, 张秀玲. 非贵金属双功能催化剂在锌空气电池研究进展[J]. 化工进展, 2023, 42(S1): 276-286.
[2]	时永兴, 林刚, 孙晓航, 蒋韦庚, 乔大伟, 颜彬航. 二氧化碳加氢制甲醇过程中铜基催化剂活性位点研究进展[J]. 化工进展, 2023, 42(S1): 287-298.
[3]	谢璐垚, 陈崧哲, 王来军, 张平. 用于SO₂去极化电解制氢的铂基催化剂[J]. 化工进展, 2023, 42(S1): 299-309.
[4]	杨霞珍, 彭伊凡, 刘化章, 霍超. 熔铁催化剂活性相的调控及其费托反应性能[J]. 化工进展, 2023, 42(S1): 310-318.
[5]	高雨飞, 鲁金凤. 非均相催化臭氧氧化作用机理研究进展[J]. 化工进展, 2023, 42(S1): 430-438.
[6]	王乐乐, 杨万荣, 姚燕, 刘涛, 何川, 刘逍, 苏胜, 孔凡海, 朱仓海, 向军. SCR脱硝催化剂掺废特性及性能影响[J]. 化工进展, 2023, 42(S1): 489-497.
[7]	赵景超, 谭明. 表面活性剂对电渗析减量化工业含盐废水的影响[J]. 化工进展, 2023, 42(S1): 529-535.
[8]	李化全, 王明华, 邱贵宝. 硫酸酸解钙钛矿相精矿的行为[J]. 化工进展, 2023, 42(S1): 536-541.
[9]	邓丽萍, 时好雨, 刘霄龙, 陈瑶姬, 严晶颖. 非贵金属改性钒钛基催化剂NH₃-SCR脱硝协同控制VOCs[J]. 化工进展, 2023, 42(S1): 542-548.
[10]	王谨航, 何勇, 史伶俐, 龙臻, 梁德青. 气体水合物阻聚剂研究进展[J]. 化工进展, 2023, 42(9): 4587-4602.
[11]	程涛, 崔瑞利, 宋俊男, 张天琪, 张耘赫, 梁世杰, 朴实. 渣油加氢装置杂质沉积规律与压降升高机理分析[J]. 化工进展, 2023, 42(9): 4616-4627.
[12]	王晋刚, 张剑波, 唐雪娇, 刘金鹏, 鞠美庭. 机动车尾气脱硝催化剂Cu-SSZ-13的改性研究进展[J]. 化工进展, 2023, 42(9): 4636-4648.
[13]	王鹏, 史会兵, 赵德明, 冯保林, 陈倩, 杨妲. 过渡金属催化氯代物的羰基化反应研究进展[J]. 化工进展, 2023, 42(9): 4649-4666.
[14]	张启, 赵红, 荣峻峰. 质子交换膜燃料电池中氧还原反应抗毒性电催化剂研究进展[J]. 化工进展, 2023, 42(9): 4677-4691.
[15]	王伟涛, 鲍婷玉, 姜旭禄, 何珍红, 王宽, 杨阳, 刘昭铁. 醛酮树脂基非金属催化剂催化氧气氧化苯制备苯酚[J]. 化工进展, 2023, 42(9): 4706-4715.