The Research Progress of Hexafluorobutadiene Synthesis
Affiliation(s)
Research and Development Center of Petrochemical Technology, Tianjin University, Tianjin, China.
Research and Development Center of Petrochemical Technology, Tianjin University, Tianjin, China.
ABSTRACT
Hexafluorobutadiene is a new plasma etching gas for semiconductor molectron which has perfect properties and also is a preceding monomer that can be used for synthesizing many fluorinated compounds. This paper described the different synthesis methods of perflurobutadiene from different materials, and contrasted the characteristic of each synthetic method. The route from tetrafluoroethylene has more industrialization prospects.
Hexafluorobutadiene is a new plasma etching gas for semiconductor molectron which has perfect properties and also is a preceding monomer that can be used for synthesizing many fluorinated compounds. This paper described the different synthesis methods of perflurobutadiene from different materials, and contrasted the characteristic of each synthetic method. The route from tetrafluoroethylene has more industrialization prospects.
KEYWORDS
Perfluorobutadiene, Synthesis, Diiodoperfluoroalkanes, Trifluoromonochloroethylene, Tetrafluoroethylene, 1, 2-Difluoro-1’, 2’-dichloroethylene
Perfluorobutadiene, Synthesis, Diiodoperfluoroalkanes, Trifluoromonochloroethylene, Tetrafluoroethylene, 1, 2-Difluoro-1’, 2’-dichloroethylene
Cite this paper
Zhu, J. , Chen, S. , Wang, B. and Zhang, X. (2014) The Research Progress of Hexafluorobutadiene Synthesis. International Journal of Organic Chemistry, 4, 331-338. doi: 10.4236/ijoc.2014.45036.
Zhu, J. , Chen, S. , Wang, B. and Zhang, X. (2014) The Research Progress of Hexafluorobutadiene Synthesis. International Journal of Organic Chemistry, 4, 331-338. doi: 10.4236/ijoc.2014.45036.
References
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http://dx.doi.org/10.1016/S0022-1139(98)00295-4 [4] Sun, W. and Wang, X. (2010) Soldering-Pan and Forming Method Thereof. CN101645408-A. [5] Park, S., Cheong, J. and Park, S.S. (2008) Method for Fabricating Capacitor in Semiconductor Device. US200808- 1429-A1. [6] Jun, M., Hitoshi, Y. and Hirozaku, A. (2003) Process for Production of Perfluoroalkadienes. US6610896. [7] Hung, H., Caulfield, J.P and Shan, H. (2003) Process for Etching Oxide Using Heafluorobutadiene or Related Fluorocarbons and Manifesting a Wide Process Window. US6602434. [8] Rensmo, H., Keis, K., Lindstrom, H., et al. (1997) High Light-to-Energy Conversion Efficiencies for Solar Cells Based on Nanostructured ZnO Electrodes. Journal of Physical Chemistry B, 101, 2598-2601.
http://dx.doi.org/10.1021/jp962918b [9] Yagupolskii, L.M., Chernega, О.I., Kondratenko, N.V., et al. (2010) Synthesis of the First Representative of Dicarbonthiacyanine Dyes with Completely Fluorinated Polymethine Chain. Journal of Fluorine Chemistry, 131, 165-171 [10] Hung, R., Caulfield, J.P., Shan, H., et al. (2003) Highly Selective Oxide Etching Process Using Hexafluorobutadiene. US 6613691. [11] Hung, H., Caulfield, J.P., Shan, H.Q., et al. (2003) Highly Selective Process for Etching Oxide over Nitride Using Hexafluorobutadiene. US 2003/0000913. [12] Palmer, R.R. and Ralph, D. (1958) Preparation of Hexafluorobutadiene. GB798407. [13] Miller, W.T. (1950) Polyunsaturated Fluoroolefins. US2668182. [14] Haszeldine, R.N. (1962) Coupling of Halogenated Organic Compounds. US3046304. [15] Harmon, J. (1943) Polyfluorocyclobutenes. US2436142. [16] Young, D. (1960) Improvements in or Relating to the Preparation of 1,2,3,4-tetrahydroperfluorobutane and Perfluorobutadiene. GB839756. [17] Veeraraghavan Ramachandran, P. and Venkat Reddy, G. (2008) Preparative-Scale One-Pot Syntheses of Hexafluoro-1,3-Butadiene. Journal of Fluorine Chemistry, 129, 443-446.
http://dx.doi.org/10.1016/j.jfluchem.2008.01.015 [18] Robertovich, M.O. (2008) Method of Obtaining Hexafluorobutadiene. RU2340588. [19] Wang, Y., Wang, Q.M., Shen, D.X., et al. (2012) Method for Preparing Hexafluorobutadiene-1,3. CN102399128. [20] Tortelli, V., Millefanti, S. and Carella, S. (2010) Process for the Synthesis of Perfluorobutadiene. US2010/0280291. [21] Haszeldine, R.N. (1951) Synthesis of Fluorocarbons, Perfluoroalkyl Iodides, Bromides and Chlorides, and Perfluoroalkyl Grignard Reagnts. Nature, 167, 139-140.
http://dx.doi.org/10.1038/167139a0 [22] Dindi, H. and Hagedorn, J.J. (2004) Process for Manufacturing Diiodoperfluoroalkanes. US 006825389. [23] Thiokol Chemical Corporation (US) (1973) Method of Making Alpha-Omega-Diiodoperfluoroalkanes. GB1301617. [24] Zhang, Z.L., Zhu, J., Jing, X., et al. (2005) Method for Preparing Alpha, Omega Diiodoperfluo-Alkane. CN1686985. [25] Tortelli, V. and Tonelit, C. (1990) Telomerization of Tetrafluoroethylene and Hexafluoropropene: Synthesis of Diiodoperfluoroalkanes. Journal of Fluorine Chemistry, 47, 199-217.
http://dx.doi.org/10.1016/S0022-1139(00)82373-8 [26] Suzuki, K., Uchijima, Y., Munakata, S., et al. (1978) Preparation of 1, 4-diiodoperfluorobutane. JP53144507 (A). [27] Jun, M. and Htoshi, Y. (2002) Process for Production of Perfluoroalkadienes. EP1247791. [28] Bargigia, G. and Tortelli, V. (1987) Process for the Synthesis of Hexafluorobutadiene and of Higher Perfluoronated dienes. US4654448. [29] Bargigia, G., Tortelli, V. and Tonelli, C. (1987) Process for the Synthesis of Perfluoroalkandiene. EP 0270956. [30] Ji, H.S., Cho, O.J. and Ahn, Y.H. (2009) Method for Preparing Perfluoroalkandiene. US7504547. [31] Zhu, J., Wang, B.H. and Liu, D.Z. (2013) Synthesis of 1,2-diiodotetrafluoroethane with Pyrolysis Gas of Waste Polyterafluoroethylene as Raw Material. Green Chemistry, 15, 1042-1047.
http://dx.doi.org/10.1039/c3gc36880g [32] Zhu, J., Liu, C., Wang, B.H., et al. (2010) Preparation Method of Hexafluorobutadiene. CN101774884.