Effect of chloralkanes on the phenyltrichlorosilane synthesis by gas phase condensation

doi:10.1016/j.cjche.2014.11.003

Chinese Journal of Chemical Engineering ›› 2015, Vol. 23 ›› Issue (1): 71-75.DOI: 10.1016/j.cjche.2014.11.003

• 催化、动力学与反应工程 • 上一篇下一篇

Effect of chloralkanes on the phenyltrichlorosilane synthesis by gas phase condensation

Tong Liu, Yunlong Huang, Chao Wang, Qiang Tang, Jinfu Wang

Beijing Key Laboratory of Green Reaction Engineering and Technology, Department of Chemical Engineering, Tsinghua University, Beijing 100084, China

收稿日期:2013-07-26 修回日期:2013-11-14 出版日期:2015-01-28 发布日期:2015-01-24
通讯作者: Jinfu Wang

Effect of chloralkanes on the phenyltrichlorosilane synthesis by gas phase condensation

Tong Liu, Yunlong Huang, Chao Wang, Qiang Tang, Jinfu Wang

Beijing Key Laboratory of Green Reaction Engineering and Technology, Department of Chemical Engineering, Tsinghua University, Beijing 100084, China

Received:2013-07-26 Revised:2013-11-14 Online:2015-01-28 Published:2015-01-24
Contact: Jinfu Wang

摘要/Abstract

摘要： To enhance the process of phenyltrichlorosilane synthesis using gas phase condensation, a series of chloralkanes were introduced. The influence of temperature and chloralkane amount on the synthesis was studied based on the product distribution from a tubular reactor. The promoting effect of chloralkane addition was mainly caused by the chloralkane radicals generated by the dissociation of C-Cl bond. The promoting effect of the chloromethane withmore chlorine atomswas better than thosewith less chlorine atoms. Intermediates detected fromthe reactions with isoprene and bromobenzene demonstrated that both trichlorosilyl radical and dichlorosilylene existed in the reaction system in the presence of chloralkanes. A detailed reaction scheme was proposed.

关键词: Phenyltrichlorosilane, Gas phase condensation, Chloralkane, Reaction mechanism, Radical, Synthesis

Abstract: To enhance the process of phenyltrichlorosilane synthesis using gas phase condensation, a series of chloralkanes were introduced. The influence of temperature and chloralkane amount on the synthesis was studied based on the product distribution from a tubular reactor. The promoting effect of chloralkane addition was mainly caused by the chloralkane radicals generated by the dissociation of C-Cl bond. The promoting effect of the chloromethane withmore chlorine atomswas better than thosewith less chlorine atoms. Intermediates detected fromthe reactions with isoprene and bromobenzene demonstrated that both trichlorosilyl radical and dichlorosilylene existed in the reaction system in the presence of chloralkanes. A detailed reaction scheme was proposed.

Key words: Phenyltrichlorosilane, Gas phase condensation, Chloralkane, Reaction mechanism, Radical, Synthesis

Tong Liu, Yunlong Huang, Chao Wang, Qiang Tang, Jinfu Wang . Effect of chloralkanes on the phenyltrichlorosilane synthesis by gas phase condensation[J]. Chinese Journal of Chemical Engineering, 2015, 23(1): 71-75.

Tong Liu, Yunlong Huang, Chao Wang, Qiang Tang, Jinfu Wang . Effect of chloralkanes on the phenyltrichlorosilane synthesis by gas phase condensation[J]. Chin.J.Chem.Eng., 2015, 23(1): 71-75.

参考文献

[1] M.B. Smith, K. Efimenko, D.A. Fischer, S.E. Lappi, P.K. Kilpatrick, J. Genzer, Study of the packing density and molecular orientation of bimolecular self-assembled monolayers of aromatic and aliphatic organosilanes on silica, Langmuir 23 (2) (2006) 673-683.

[2] S. Yamamoto, N. Yasuda, A. Ueyama, H. Adachi, M. Ishikawa, Mechanism for the formation of poly(phenylsilsesquioxane), Macromolecules 37 (8) (2004) 2775-2778.

[3] M.D.K. Ingall, C.H. Honeyman, J.V. Mercure, P.A. Bianconi, R.R. Kunz, Surface functionalization and imaging using monolayers and surface-grafted polymer layers, J. Am. Chem. Soc. 121 (15) (1999) 3607-3613.

[4] L. Patrone, V. Gadenne, S. Desbief, Single and binary self-assembled monolayers of phenyl-and pentafluorophenyl-based silane species, and their phase separation with octadecyltrichlorosilane, Langmuir 26 (22) (2010) 17111-17118.

[5] J. Moineau, M. Granier, G.F. Lanneau, Organized self-assembled monolayers from organosilanes containing rigid π-conjugated aromatic segments, Langmuir 20 (8) (2004) 3202-3207.

[6] Z.F. Li, E. Ruckenstein, Patterned conductive polyaniline on Si(100) surface via selfassembly and graft polymerization, Macromolecules 35 (25) (2002) 9506-9512.

[7] Y. Ide, S. Iwasaki, M. Ogawa, Molecular recognition of 4-nonylphenol on a layered silicate modified with organic functionalities, Langmuir 27 (6) (2011) 2522-2527.

[8] A.D. Petrov, E.A. Chernyshev, K. Li, Mechanism of reaction of silicon hydrides with organic halides in the gas phase, Dokl. Akad. Nauk SSSR 137 (1961) 876-879.

[9] E.A. Chernyshev, G. Li, A.D. Petrov, A new method of synthesis of organosilicon aromatic monomers, Dokl. Akad. Nauk SSSR 127 (1959) 808-811.

[10] Goetze, U., Schmidt, E., Hansel, M., Zeller, N., Production of organosilane, e.g. phenyltrichlorosilane, involves reacting a hydrogen-silane with a halogenated hydrocarbon in presence of a radical initiator of the alkane, diazene or disilane type, e.g. 1,2-diphenylethane., U.S. Pat., 7211683 B2 (2007).

[11] T.L.Krasnova, E.S. Abramova,N.V.Alekseev, E.A. Chernyshev,Pyrolysisof trichlorosilane in the presence of chloroform, Izv. Akad. Nauk SSSR Senia Khim. 48 (10) (1999) 1960-1963.

[12] I.M.T. Davidson, C. Eaborn, C.J.Wood, Organosilicon compounds: XLI. A kinetic study of the gas-phase reaction between silicon hydrides and aryl chlorides, J. Organomet. Chem. 10 (3) (1967) 401-408.

[13] E.A. Chernyshev, T.L. Krasnova, E.S. Abramova, I.A. Abronin, A.B. Petrunin, A.P. Sergeev, Experimental and theoretical study of the pyrolysis of trichlorosilane, Izv. Akad. Nauk SSSR Senia Khim. 46 (9) (1997) 1582-1585.

[14] J. Heinicke, B. Gehrhus, Role of the trichlorosilyl radical and dichlorosilylene in gasphase reactions of trichlorosilane, J. Anal. Appl. Pyrolysis 28 (1) (1994) 81-92.

[15] E.A. Chernyshev, N.G. Komalenkova, G.N. Yakovleva, V.G. Bykovchenko, Gas-phase synthesis of phenyltrichlorogermane by reaction of tetrachlorogermane with chlorobenzene in the presence of initiators, Zh. Obshch. Khim. 65 (11) (1995) 1869-1872.

[16] D.R. Lide, CRC Handbook of Chemistry and Physics, 90th edition CRC Press, Boca Raton, 2010.

[17] C. Wang, G. Wang, J. Wang, A bi-component Cu catalyst for the direct synthesis of methylchlorosilane from silicon and methyl chloride, Chin. J. Chem. Eng. 22 (3) (2014) 299-304.

[18] K.A. Andrianov, V.M. Kotov, V.Y. Kovalenko, Pyrolysis ofmethylphenyldichlorosilane, Russ. Chem. Bull. 21 (2) (1972) 310.

[19] E.A. Chernyshev, N.G. Komalenkova, G.N. Yakovleva, V.G. Bykovenko, V.V.Shcherbinin, A.I. Belokon, Gas phase reaction of tetrachlorogermane with conjugated dienes in the presence of hexachlorodisilane initiator, Zh. Obshch. Khim. 71 (9) (2001) 1438-1442.

[20] E.A. Chernyshev, N.G.Komalenkova, V.G. Bykovchenko, Advances inthe gas-phase synthesis of organochloro derivatives of silicon, germanium, and tin via dichlorosilylene, Izv. Akad. Nauk SSSR Senia Khim. 47 (6) (1998) 1029-1036.

[21] E.A. Chernyshev, V.G. Bykovchenko, T.S. Kisileva, Reaction of trichlorosilane with aryl chlorides in the presence of cyclopentadiene. Mechanism of arylchlorosilane formation, Zh. Obshch. Khim. 62 (2) (1992) 364-366.

[22] E.A. Chernyshev, N.G. Komalenkova, S.A. Bashkirova, Gas phase reactions of dichlorosilylene, J. Organomet. Chem. 271 (1-3) (1984) 129-143.

Effect of chloralkanes on the phenyltrichlorosilane synthesis by gas phase condensation

Effect of chloralkanes on the phenyltrichlorosilane synthesis by gas phase condensation

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	Mingzhi Li, Zhikai Liu, Wang Yao, Chao Xu, Yangping Yu, Mei Yang, Guangwen Chen. Ultrasonic cavitation-enabled microfluidic approach toward the continuous synthesis of cesium lead halide perovskite nanocrystals[J]. 中国化学工程学报, 2023, 59(7): 32-41.
[2]	Haixiang Liu, Jun Zhang, Chunlei Dong, Gang Zhu, Guanben Du, Shuduan Deng. Synthesis, performance and structure characterization of glyoxal-monomethylolurea-melamine (G-MMU-M) co-condensed resin[J]. 中国化学工程学报, 2023, 59(7): 92-104.
[3]	Yi Wu, Pengfei Song, Ningyan Li, Yanan Jiang, Yuan Liu. Molybdenum tailored Co⁰/Co²⁺ active pairs on a perovskite-type oxide for direct ethanol synthesis from syngas[J]. 中国化学工程学报, 2023, 59(7): 279-289.
[4]	Bin Lin, Wenyao Chen, Nan Song, Zhihua Zhang, Qianhong Wang, Wei Du, Xinggui Zhou, Xuezhi Duan. Mechanistic insights into propylene oxidation to acrolein over gold catalysts[J]. 中国化学工程学报, 2023, 57(5): 39-49.
[5]	Yaqiao Liu, Shuozhen Hu, Xinsheng Zhang, Shigang Sun. Investigation of photoelectrocatalytic degradation mechanism of methylene blue by α-Fe₂O₃ nanorods array[J]. 中国化学工程学报, 2023, 57(5): 162-172.
[6]	Kai Xue, Yanchun Xue, Jing Wang, Shuya Zhang, Xingmei Guo, Xiangjun Zheng, Fu Cao, Qinghong Kong, Junhao Zhang, Zhong Jin. KOH-assisted aqueous synthesis of ZIF-67 with high-yield and its derived cobalt selenide/carbon composites for high-performance Li-ion batteries[J]. 中国化学工程学报, 2023, 57(5): 214-223.
[7]	Yuhan Zhu, Jia Wei, Jun Li. Decontamination of Cr(VI) from water using sewage sludge-derived biochar: Role of environmentally persistent free radicals[J]. 中国化学工程学报, 2023, 56(4): 97-103.
[8]	Shuang Qiu, Yonghou Xiao, Haoran Wu, Shengnan Lu, Qidong Zhao, Gaohong He. One-pot synthesis of bimetallic CeCu-SAPO-34 for high-efficiency selective catalytic reduction of nitrogen oxides with NH₃ at low temperature[J]. 中国化学工程学报, 2023, 56(4): 193-202.
[9]	Wufeng Wu, Xilu Hong, Jiang Fan, Yanying Wei, Haihui Wang. Research progress on the substrate for metal–organic framework (MOF) membrane growth for separation[J]. 中国化学工程学报, 2023, 56(4): 299-313.
[10]	Aiqin Gao, Xiang Luo, Huanghuang Chen, Aiqin Hou, Hongjuan Zhang, Kongliang Xie. Design of the reactive dyes containing large planar multi-conjugated systems and their application in non-aqueous dyeing[J]. 中国化学工程学报, 2023, 54(2): 264-271.
[11]	Tengjie Wang, Wenkai Li, Xuehui Ge, Ting Qiu, Xiaoda Wang. Kinetics measurement of ethylene-carbonate synthesis via a fast transesterification by microreactors[J]. 中国化学工程学报, 2023, 53(1): 243-250.
[12]	An Wang, Zhongyu Hou. Improving the energy efficiency of surface dielectric barrier discharge devices for plasma nitric oxide conversion utilizing active flow control[J]. 中国化学工程学报, 2023, 53(1): 270-279.
[13]	Xuan Gao, Zhihui Li, Dongsheng Zhang, Xinqiang Zhao, Yanji Wang. Synthesis and kinetics of 2,5-dicyanofuran in the presence of hydroxylamine ionic liquid salts[J]. 中国化学工程学报, 2023, 53(1): 310-316.
[14]	Min Lu, Mengxuan Liu, Chunli Xu, Yu Yin, Lei Shi, Hong Wu, Aihua Yuan, Xiao-Ming Ren, Shaobin Wang, Hongqi Sun. Location and size regulation of manganese oxides within mesoporous silica for enhanced antibiotic degradation[J]. 中国化学工程学报, 2022, 48(8): 36-43.
[15]	Yimin Zhang, Ruiming Zeng, Yun Zu, Linhua Zhu, Yi Mei, Yongming Luo, Dedong He. Low-temperature dry reforming of methane tuned by chemical speciations of active sites on the SiO₂ and γ-Al₂O₃ supported Ni and Ni-Ce catalysts[J]. 中国化学工程学报, 2022, 48(8): 76-90.