Effect of Aminoaromatic Acids as Additives on the Activity and Selectivity of the Platinum-catalyzed Hydrosilylation of Alkenes

Abstract

Abstract: A series of aromatic acids has been tested as additives for the platinum-catalyzed hydrosilylation of styrene with triethoxysilane.Both excellent conversion of styrene and selectivity in favor of the β-adduct were achieved using aminobenzoic acids as additive.Moreover,the use of 4-aminobenzoic acid led to significantly superior enhancement in both catalytic activity and selectivity among the tested aminobenzoic acids.Indeed,100% conversion of styrene and 98.4% selectivity in favor of the β-adduct were obtained.Additionally,hydrosilylations of various alkenes with a variety of platinum catalysts have also been tested,and in each case the conversion of substrate and the selectivity of the β-adduct were promoted by using 4-aminobenzoic acid as additive.

Key words: hydrosilylation, platinum catalyst, aminoaromatic acid, additive

摘要： A series of aromatic acids has been tested as additives for the platinum-catalyzed hydrosilylation of styrene with triethoxysilane.Both excellent conversion of styrene and selectivity in favor of the β-adduct were achieved using aminobenzoic acids as additive.Moreover,the use of 4-aminobenzoic acid led to significantly superior enhancement in both catalytic activity and selectivity among the tested aminobenzoic acids.Indeed,100% conversion of styrene and 98.4% selectivity in favor of the β-adduct were obtained.Additionally,hydrosilylations of various alkenes with a variety of platinum catalysts have also been tested,and in each case the conversion of substrate and the selectivity of the β-adduct were promoted by using 4-aminobenzoic acid as additive.

关键词: hydrosilylation, platinum catalyst, aminoaromatic acid, additive

BAI Ying, PENG Jiajian, HU Yingqian, LI Jiayun, QIU Huayu, LAI Guoqiao. Effect of Aminoaromatic Acids as Additives on the Activity and Selectivity of the Platinum-catalyzed Hydrosilylation of Alkenes[J]. , 2009, 17(6): 1038-1042.

白赢, 彭家建, 胡应乾, 厉嘉云, 邱化玉, 来国桥. Effect of Aminoaromatic Acids as Additives on the Activity and Selectivity of the Platinum-catalyzed Hydrosilylation of Alkenes[J]. , 2009, 17(6): 1038-1042.

References

1 Marciniec, B., Guliński, J., Urbaniak, W., Kornetka, Z.W., Comprehensive Handbook on Hydrosilylation, Pergamon Press, London(1992).
2 Sommer, L., Pietrusza, H.E.W., Whitmore, F.C., “Peroxide-catalyzed addition of trichlorosilane to 1-octene”, J. Am. Chem. Soc., 69(1), 188-189(1947).
3 Speier, J.L., Machay, F.P., Steward, Q.W., Campbell, P.G., “The addition of silicon hydrides to alkeneic double bonds(II) The use of group VIII metal catalysts”, J. Am. Chem. Soc., 79(4), 974-979(1957).
4 Ryan, J.W., Speier, J.L., “Notes-addition of silicon hydrides to alkeneic double bonds(IV) The addition to styrene and α-methylstyrene”, J.Org. Chem., 24(12), 2052-2053(1959).
5 Karstedt, B.D., Scotia, N.Y., “Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes”, US Pat., 3775452(1973).
6 Marciniec, B., Kornetka, Z.M., Urbaniak, W., “Platinum and rhodium complexes supported on aminated silica as hydrosilylation catalysts”, J. Mol. Catal., 12(2), 221-230(1981).
7 Wang, L.Z., Jiang, Y.Y., “Catalytic activity and selectivity of poly-γ-aminopropylsiloxane-Pt complex in hydrosilylation of unsaturated compounds”, Chin. J. Catal., 2(3), 236-238(1981).(in Chinese)
8 Wang, L.Z., Jiang, Y.Y., “An active and stable hydrosilylation catalyst, silica-poly-γ-mercaptopropyl-siloxane-platinum complex”, Macromol. Comm., 78-82(1983).(in Chinese)
9 Hu, C.Y., Han, X.M., Jiang, Y.Y., “Hydrosilylation of acetylene catalyzed by a sulfur-containing polysiloxane platinum complex”, J. Mol. Catal., 35(3), 329-333(1986).
10 Chen, Y.M., Lu, X.R., Zhong, Z.L., “Synthesis of poly-4,7dithianonylsesquisiloxane platinum complex and its catalyst activity on hydrosilylation of olefins with triethoxysilane”, Appl. Chem., 9(3), 26-30(1992).(in Chinese)
11 Liedtke, J., Loss, S., Widauer, C., Grützmacher, H., “Phosphiranes as ligands for platinum catalysed hydrosilylations”, Tetrahedron, 56, 143-156(2000).
12 Prignano, A.L., Trogler, W.C., “Silica-supported bis(trialkylphosphine) platinum oxalates. Photogenerated catalysts for hydrosilylation of alkenes”, J. Am. Chem. Soc., 109(12), 3586-3595(1987).
13 Yamamoto, K., Hayashi, T., Zembayashi, M., Kumada, M., “Catalytic asymmetric hydrosilylation of alkenes(II) chiral phosphine-platinum(II) complexes as hydrosilylation catalysts”, J. Organomet. Chem., 118(2), 161-181(1976).
14 Marciniec, B., Foltynowicz, Z., Urbaniak, W., “Catalysis of hydrosilylation(XV) A poly(phosphino-organosiloxanyl)silicate-supported rhodium(I) catalyst for gas-phase hydrosilylation of acetylene”, Appl. Organomet. Chem., 1(5), 459-463(1987).
15 Markó, I.E., Stérin, S., Buisine, O., Mignani, G., Branlard, P., Tinant, B., Declercq, J.P., “Selective and efficient platinum(0)-carbene complexes as hydrosilylation catalysts”, Science, 298, 204-206(2002).
16 Bo, D.G., Berthon-Gelloz, G., Tinant, B., “Hydrosilylation of alkynes mediated by N-heterocyclic carbene platinum(0) complexes”, Organometallics, 25(8), 1881-1890(2006).
17 Markó, I.E., Stérin, S., Buisine, O., Berthon, G., Michaud, G., Tinant, B., Declercq, J.P., “Highly active and selective platinum(0)-carbene complexes:Efficient, catalytic hydrosilylation of functionalised alkenes”, Adv. Synth. Catal., 346(12), 1429-1434(2004).
18 Berthon-Gelloz, G., Buisine, O., Brière, J. F., Michaud, G., Stérin, S., Mignani, G., Tinant, B., Declercq, J.P., Chapon, D., Markó, I.E., “Synthetic and structural studies of NHC-Pt(dvtms) complexes and their application as alkene hydrosilylation catalysts(NHC=N-heterocyclic carbene, dvtms=divinyltetramethylsiloxane)”, J. Organomet. Chem., 690(24/25), 6156-6168(2005).
19 Poyatos, M., Maisse-Francüois, A., Bellemin-Laponnaz, S., Gade, L.H., “Coordination chemistry of a modular N,C-chelating oxazole-carbene ligand and its applications in hydrosilylation catalysis”, Organometallics, 25(10), 2634-2641(2006).
20 Mehta, K.R., “Process for the preparation of siloxane-oxyalkylene copolymers”, US Pat., 4847398(1989).
21 Curtis, L., Schilling, Jr., “Method of highly efficient hydrosilylation”, CN 99122127.3(1999).
22 Hamze, A., Provot, O., Brion, J.D., Alami, M., “Xphos ligand and platinum catalysts:A versatile catalyst for the synthesis of functionalized β-(E)-vinylsilanes from terminal alkynes”, J. Organomet. Chem., 693(16), 2789-2797(2008).
23 Hamze, A., Provot, O., Brion, J.D., Alami, M., “Platinum chloride/Xphos-catalyzed regioselective hydrosilylation of functionalized terminal arylalkynes”, Tetrahedron Lett., 49, 2429-2431(2008).
24 Arsenyan, P., Oberte, K., Rubina, K., Belyakov, S., “Synthesis and application of a new selenoplatinum catalyst”, Tetrahedron Lett., 46, 1001-1003(2005).

[1]	Shaojun Niu, Guobin Zhu, Kai Wu, Honghe Zheng. The feasibility for natural graphite to replace artificial graphite in organic electrolyte with different film-forming additives [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 58-69.
[2]	Hengyu Shen, Run Zou, Yangtao Zhou, Xing Guo, Yanan Guan, Duo Na, Jinsong Zhang, Xiaolei Fan, Yilai Jiao. Additive manufacturing of sodalite monolith for continuous heavy metal removal from water sources [J]. Chinese Journal of Chemical Engineering, 2022, 42(2): 82-90.
[3]	Tong Luo, Shaolong Liu, Cong Luo, Xiaolei Qi, Bowen Lu, Liqi Zhang. Effect of different organic compounds on the preparation of CaO-based CO₂ sorbents derived from wet mixing combustion synthesis [J]. Chinese Journal of Chemical Engineering, 2021, 36(8): 157-169.
[4]	Xiaofei Qin, Sen Lei, Xubin Zhang, Chen Cao, Feng Xin, Honglin Chen, Xiaoming Zhang, Yachen Yin, Guilian Wu. Formation kinetics of polyoxymethylene dimethyl ethers from methylal and trioxane with little water [J]. Chinese Journal of Chemical Engineering, 2021, 33(5): 139-146.
[5]	Chaofeng Zhang, Tonglu Zhang, Jing Zhang, Jiandong Zhang, Ruifeng Li. Controllable synthesis of polyoxymethylene dimethyl ethers by ionic liquids encapsulated in mesoporous SBA-16 [J]. Chinese Journal of Chemical Engineering, 2021, 32(4): 175-182.
[6]	Mojtaba Masdarian, Asghar Azizi, Zahra Bahri. Mechanochemical sulfidization of a mixed oxide-sulphide copper ore by co-grinding with sulfur and its effect on the flotation efficiency [J]. Chinese Journal of Chemical Engineering, 2020, 28(3): 743-748.
[7]	Pengcheng Hu, Jingwei Zheng, Wei Jiang, Lijuan Zhong, Shufeng Zhou. Isomerization of n-pentane catalyzed by amide-AlCl₃-based ionic liquid analogs with various additives [J]. Chinese Journal of Chemical Engineering, 2020, 28(1): 152-157.
[8]	M. A. Asidin, E. Suali, T. Jusnukin, F. A. Lahin. Review on the applications and developments of drag reducing polymer in turbulent pipe flow [J]. Chinese Journal of Chemical Engineering, 2019, 27(8): 1921-1932.
[9]	Lingyu Wang, Xiaona Li, Yumin Liu, Dandan Han, Shiyuan Liu, Teng Zhang, Bo Yu, Junbo Gong. Insight into the degradation mechanism of cefixime under crystallization condition [J]. Chin.J.Chem.Eng., 2018, 26(7): 1458-1467.
[10]	Kibrom Alebel Gebru, Chandan Das. Effects of solubility parameter differences among PEG,PVP and CA on the preparation of ultrafiltration membranes:Impacts of solvents and additives on morphology,permeability and fouling performances [J]. , 2017, 25(7): 911-923.
[11]	Zhuan Yi, Fa-dong Wu, Yong Zhou, Cong-jie Gao. Novel nanofiltration membranes with tunable permselectivity by polymer mediated phase separation in polyamide selective layer [J]. Chin.J.Chem.Eng., 2016, 24(11): 1533-1540.
[12]	Hui Li, Kuihua Han, Hongtao Liu, Chunmei Lu. Experimental and Modeling Study on de-NO_x Characteristics of Selective Non-catalytic Reduction in O₂/CO₂ Atmosphere [J]. Chin.J.Chem.Eng., 2014, 22(8): 943-949.
[13]	Sulekh Chandra, Deepshikha Singh, Anjana Sarkar. PVC Membrane Selective Electrode for Determination of Cadmium(Ⅱ) Ion in Chocolate Samples [J]. Chin.J.Chem.Eng., 2014, 22(4): 480-488.
[14]	BAI Ying, PENG Jiajian, YANG Hu, LI Jiayun, LAI Guoqiao, LI Xiaonian. Functional Polyethylene Glycol with Carboxyl-supported Platinum as an Efficient Catalysis System for the Hydrosilylation of Alkenes [J]. Chin.J.Chem.Eng., 2012, 20(2): 246-253.
[15]	LIU Haiyan, CAO Liyuan, WEI Baoying, FAN Yu, SHI Gang, BAO Xaojun. In-situ Synthesis and Catalytic Properties of ZSM-5/Rectorite Composites as Propylene Boosting Additive in Fluid Catalytic Cracking Process [J]. Chin.J.Chem.Eng., 2012, 20(1): 158-166.