Process for producing highly pure chlorinated alkane

Abstract

Disclosed is a process for producing highly pure chlorinated alkane in which a chlorinated alkene is contacted with chlorine in a reaction zone to produce a reaction mixture containing the chlorinated alkane and the chlorinated alkene, and extracting a portion of the reaction mixture from the reaction zone, wherein the molar ratio of chlorinated alkane:chlorinated alkene in the reaction mixture extracted from the reaction zone does not exceed 95:5.

1 . A process for producing highly pure chlorinated alkane in which a chlorinated alkene is contacted with chlorine in a reaction zone to produce a reaction mixture containing the chlorinated alkane and the chlorinated alkene, and extracting a portion of the reaction mixture from the reaction zone, wherein the molar ratio of chlorinated alkane:chlorinated alkene in the reaction mixture extracted from the reaction zone does not exceed 95:5. 
     
     
         2 . The process of  claim 1 , wherein the chlorinated alkene is 1,1,3-trichloropropene and the chlorinated alkane is 1,1,1,2,3-pentachloropropane. 
     
     
         3 . The process of  claim 1 , wherein the process is continuous. 
     
     
         4 . The process of  claim 1 , wherein the reaction zone is a primary reaction zone. 
     
     
         5 . The process of  claim 4 , wherein the molar ratio of chlorinated alkane:chlorinated alkene in the reaction mixture extracted from the primary reaction zone does not exceed 50:50. 
     
     
         6 . The process of  claim 4 , wherein the operating temperature in the primary reaction zone is about −10° C. to about 50° C. 
     
     
         7 . The process of  claim 4 , wherein the reaction mixture extracted from the primary reaction zone is subjected to a principal conversion step in a principal reaction zone to produce a chlorinated alkane rich product, which is extracted from the principal reaction zone. 
     
     
         8 . The process of  claim 7 , wherein the molar ratio of chlorinated alkane:chlorinated alkene in both i) the reaction mixture extracted from the primary reaction zone and ii) the chlorinated alkane rich product extracted from the principal reaction zone does not exceed 95:5. 
     
     
         9 . The process of  claim 8 , wherein the molar ratio of chlorinated alkane:chlorinated alkene in the chlorinated alkane rich product extracted from the principal reaction zone is higher than the molar ratio of chlorinated alkane:chlorinated alkene in the reaction mixture extracted from the primary reaction zone. 
     
     
         10 . The process of  claim 7 , wherein the reaction mixture extracted from the primary reaction zone and/or the chlorinated alkane rich product extracted from the principal reaction zone has a chlorine level of about 1% or less, about 0.5% or less, about 0.1% or less, about 0.05% or less or about 0.01% or less. 
     
     
         11 . The process of  claim 7 , wherein the principal conversion step comprises a reduced temperature conversion step in which the reaction mixture extracted from the primary reaction is fed into a principal reaction zone operated at a reduced temperature and the chlorinated alkane rich product is extracted from the principal reaction zone. 
     
     
         12 . The process of  claim 11 , wherein the reduced temperature is about −30° C. to about 30° C. 
     
     
         13 . A process for producing highly pure chlorinated alkane comprising a reduced temperature conversion step in which a reaction mixture comprising chlorinated alkene and chlorinated alkane is fed into a principal reaction zone operated at a temperature of about −30° C. to about 30° C., about −25° C. to about 10° C., or more preferably about −20° C. to about −10° C., and extracting a chlorinated alkane rich product from the principal reaction zone. 
     
     
         14 . The process according to  claim 1 , wherein the primary and/or the principal reaction zone is exposed to visible light and/or ultraviolet light. 
     
     
         15 . The process according to  claim 7  wherein a plurality of principal reaction zones are employed in sequence and the reaction mixture in the downstream principal reaction zones is exposed to ultraviolet light and/or heating. 
     
     
         16 . The process according to  claim 15 , wherein the reaction mixture in the downstream-most principal reaction zone is exposed to ultraviolet light and/or heating. 
     
     
         17 . The process according to  claim 1 , wherein the level of chlorine present in the primary and/or principal reaction zone/s is controlled such that there is no excess of chlorine present in the reaction mixture present in the primary and/or principal reaction zone/s. 
     
     
         18 . The process according to  claim 1 , wherein the reaction mixture/chlorinated alkane rich product is subjected to a hydrolysis step. 
     
     
         19 . The process according to  claim 18 , wherein the hydrolysis step comprises contacting the reaction mixture/chlorinated alkane rich product with an aqueous medium in an aqueous treatment zone. 
     
     
         20 . The process according to  claim 19 , wherein the aqueous medium forms a mixture with the reaction mixture/chlorinated alkane rich product, the process further comprising the step of extracting i) an organic phase from the mixture and/or ii) a chlorinated alkane stream from that mixture. 
     
     
         21 . A process for removing oxygenated organic compounds from a chlorinated alkane rich product comprising a chlorinated alkane, a chlorinated alkene and oxygenated organic compounds, comprising feeding the chlorinated alkane rich product into an aqueous treatment zone, contacting the chlorinated alkane rich product with an aqueous medium to produce a mixture and extracting i) an organic phase from that mixture or ii) a chlorinated alkane stream from that mixture, the organic phase/chlorinated alkane stream comprising reduced levels of oxygenated organic compounds as compared to the chlorinated alkane rich product fed into the aqueous treatment zone. 
     
     
         22 . The process of  claim 20  wherein the organic phase and/or the chlorinated alkane stream extracted from the mixture formed in the aqueous treatment zone comprises oxygenated organic compounds in amounts of about 1000 ppm or less, about 500 ppm or less, about 100 ppm or less, about 50 ppm or less, or about 10 ppm or less. 
     
     
         23 . The process of  claim 18 , wherein the reaction mixture/chlorinated alkane rich product fed into the aqueous treatment zone comprises less than about 0.1%, less than about 0.05% or less than about 0.01% chlorine. 
     
     
         24 . The process of  claim 1 , wherein the reaction mixture/chlorinated alkane rich product/organic phase extracted from the mixture formed in the aqueous treatment zone is subjected to one or more distillation steps. 
     
     
         25 . The process of  claim 24 , wherein a distillation step is performed before and/or after the hydrolysis step. 
     
     
         26 . The process of  claim 24 , wherein the distillation step is performed in a distillation column including a rectification section and a purified stream of the chlorinated alkane is extracted as a liquid phase side product from the rectification section of the distillation column. 
     
     
         27 . A method of distilling a chlorinated alkane rich product, in which distillation apparatus is employed, the distillation apparatus being free of components which, in use of the distillation apparatus, come into contact with the process fluid and comprise about 20% or more, about 10% or more, about 5% or more, about 2% or more or about 1% or more of iron. 
     
     
         28 . The method of  claim 27 , wherein the distillation apparatus is configured such that all of its components which, in use of the distillation apparatus, would come into contact with the distillate or process liquid are produced from fluoropolymers, fluorochloropolymers, glass, enamel, phenolic resin impregnated graphite, silicium carbide and/or fluoropolymer impregnated graphite. 
     
     
         29 . A composition obtainable from the process of  claim 1 . 
     
     
         30 . The composition of  claim 29 , comprising:
 The chlorinated alkane product in amounts of at least about 99.7%, at least about 99.8%, at least about 99.9%, or at least about 99.95%, and one or more of the following:   Oxygenated organic compounds in amounts of less than about 500 ppm, about 250 ppm or less, about 100 ppm or less, about 50 ppm or less, or about 10 ppm or less,   Isomers of the chlorinated alkane of interest in amounts of less than about 500 ppm or less, about 250 ppm or less, or about 100 ppm or less,   Non-isomeric alkane impurities in amounts of less than about 500 ppm, about 250 ppm or less, or about 100 ppm or less,   Chlorinated alkenes in amounts of less than about 500 ppm, about 250 ppm or less, about 100 ppm or less, or about 50 ppm or less,   Water in amounts of less than about 500 ppm, about 250 ppm or less, about 100 ppm or less or about 50 ppm or less,   Inorganic compounds of chlorine in amounts of about 100 ppm or less, about 50 ppm or less, about 20 ppm or less, or about 10 ppm or less,   Brominated organic compounds in amounts of about 100 ppm or less, about 50 ppm or less, about 20 ppm or less or about 10 ppm or less, and/or   Iron in amounts of about 100 ppm or less, about 50 ppm or less, about 20 ppm or less, about 10 ppm or less or about 5 ppm or less   
     
     
         31 . A composition comprising:
 The chlorinated alkane product in amounts of at least about 99.7%, at least about 99.8%, at least about 99.9%, or at least about 99.95%, and one or more of the following:   Oxygenated organic compounds in amounts of less than about 500 ppm, about 250 ppm or less, about 100 ppm or less, about 50 ppm or less, or about 10 ppm or less,   Isomers of the chlorinated alkane of interest in amounts of less than about 500 ppm or less, about 250 ppm or less, or about 100 ppm or less,   Non-isomeric alkane impurities in amounts of less than about 500 ppm, about 250 ppm or less, or about 100 ppm or less,   Chlorinated alkenes in amounts of less than about 500 ppm, about 250 ppm or less, about 100 ppm or less, or about 50 ppm or less,   Water in amounts of less than about 500 ppm, about 250 ppm or less, about 100 ppm or less or about 50 ppm or less,   Inorganic compounds of chlorine in amounts of about 100 ppm or less, about 50 ppm or less, about 20 ppm or less or about 10 ppm or less,   Brominated organic compounds in amounts of about 100 ppm or less, about 50 ppm or less, about 20 ppm or less or about 10 ppm or less, and/or   Iron in amounts of about 100 ppm or less, about 50 ppm or less, about 20 ppm or less, about 10 ppm or less or about 5 ppm or less.   
     
     
         32 . The composition of  claim 29 , wherein the chlorinated alkane is 1,1,1,2,3-pentachloropropane. 
     
     
         33 . The composition of  claim 32 , wherein the composition comprises less than about 1000 ppm, less than about 500 ppm, less than about 200 ppm, or less than about 100 ppm of organic compounds other than 1,1,1,2,3-pentachloropropane. 
     
     
         34 . The composition of  claim 32 , wherein the composition comprises less than about 1000 ppm, less than about 500 ppm, less than about 200 ppm, or less than about 100 ppm of 1,1,3,3-Tetrachloropropene, 1,1,1,2,3,3-Hexachloropropane, and/or 1,1,1,2,2,3-Hexachloropropane. 
     
     
         35 . The composition of  claim 32 , wherein said composition is free of stabilising agents. 
     
     
         36 . Use of the composition of  claim 29  as a feedstock for use in the synthesis of a fluorinated alkane or fluorinated alkene or chlorofluorinated alkene. 
     
     
         37 . The use of  claim 36  wherein the fluorinated alkene is 2,3,3,3-tetrafluoropropene. 
     
     
         38 . The use of  claim 36 , wherein the chlorofluorinated alkene is 2-chloro-3,3,3-trifluoropropene. 
     
     
         39 . Use of the composition of  claim 31  as a feedstock for use in the synthesis of a fluorinated alkane or fluorinated alkene or chlorofluorinated alkene. 
     
     
         40 . The use of  claim 39  wherein the fluorinated alkene is 2,3,3,3-tetrafluoropropene. 
     
     
         41 . The use of  claim 39 , wherein the chlorofluorinated alkene is 2-chloro-3,3,3-trifluoropropene. 
     
     
         42 . The composition of  claim 31 , wherein the chlorinated alkane is 1,1,1,2,3-pentachloropropane. 
     
     
         43 . The composition of  claim 42 , wherein the composition comprises less than about 1000 ppm, less than about 500 ppm, less than about 200 ppm, or less than about 100 ppm of organic compounds other than 1,1,1,2,3-pentachloropropane. 
     
     
         44 . The composition of  claim 42 , wherein the composition comprises less than about 1000 ppm, less than about 500 ppm, less than about 200 ppm, or less than about 100 ppm of 1,1,3,3-Tetrachloropropene, 1,1,1,2,3,3-Hexachloropropane, and/or 1,1,1,2,2,3-Hexachloropropane. 
     
     
         45 . Use of the composition of  claim 32  as a feedstock for use in the synthesis of 1,1,2,3-tetrachloropropane. 
     
     
         46 . Use of the composition of  claim 42  as a feedstock for use in the synthesis of 1,1,2,3-tetrachloropropane. 
     
     
         47 . The process of  claim 21 , wherein the reaction mixture/chlorinated alkane rich product fed into the aqueous treatment zone comprises less than about 0.1%, less than about 0.05% or less than about 0.01% chlorine. 
     
     
         48 . The process of  claim 47 , wherein a distillation step is performed before and/or after the hydrolysis step. 
     
     
         49 . The process of  claim 48 , wherein the distillation step is performed in a distillation column including a rectification section and a purified stream of the chlorinated alkane is extracted as a liquid phase side product from the rectification section of the distillation column.