Azeotrope-like compositions of pentafluoropropene and water

Abstract

Provided are azeotropic and azeotrope-like compositions of 1,2,3,3,3-pentafluoropropene (HFO-1225ye) and water. Such azeotropic and azeotrope-like compositions are useful in isolating 1,2,3,3,3-pentafluoropropene from impurities during production. Azeotropes of the instant invention are similarly useful in final compositions or manufacturing final compositions, such as blowing agent, propellants, refrigerants, diluents for gaseous sterilization and the like.

We claim: 
     
       1. An azeotropic or azeotrope-like composition consisting essentially of 1,2,3,3,3-pentafluoropropene (HFO-1225ye) and water wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent. 
     
     
       2. The composition of  claim 1 , consisting of water and 1,2,3,3,3-pentafluoropropene. 
     
     
       3. The composition of  claim 1 , having a boiling point of about −20° C.±0.5° C. at a pressure of about 14.3 psia±2 psia. 
     
     
       4. The composition of  claim 1 , having a boiling point of about −20° C. at a pressure of about 14.3 psia. 
     
     
       5. The composition of  claim 1 , having a boiling point of about −20.3° C. at a pressure of about 14.39 psia. 
     
     
       6. A method of forming an azeotropic or azeotrope-like composition comprising forming a blend consisting essentially of effective amounts of water and 1,2,3,3,3-pentafluoropropene, wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent. 
     
     
       7. The method of  claim 6 , wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent. The method of claim  9  6, wherein the azeotropic or azeotrope-like composition consists of water and 1,2,3,3,3-pentafluoropropene. 
     
     
       8. The method of  claim 6 , having wherein the azeotropic or azeotrope-like composition has a boiling point of about −20° C.±0.5° C. at a pressure of about 14.3 psia±2 psia. 
     
     
       9. The method of  claim 6 , having wherein the azeotropic or azeotrope-like composition has a boiling point of about −20° C. at a pressure of about 14.3 psia. 
     
     
       10. The method of  claim 6 , having wherein the azeotropic or azeotrope-like composition has a boiling point of about −20.3° C. at a pressure of about 14.39 psia. 
     
     
       11. A method for removing 1,2,3,3,3-pentafluoropropene from a mixture containing 1,2,3,3,3-pentafluoropropene and at least one impurity, comprising adding water to the mixture in an effective amount to form an azeotropic or azeotrope-like composition of the 1,2,3,3,3-pentafluoropropene and the water, and separating the azeotropic composition from the impurity, wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent. 
     
     
       12. The method of  claim 11 , wherein the impurity does not form an azeotropic mixture with 1,2,3,3,3-pentafluoropropene, water or a mixture of 1,2,3,3,3-pentafluoropropene and water. 
     
     
       13. The method of  claim 11 , wherein the impurity does form an azeotropic mixture with 1,2,3,3,3-pentafluoropropene, water or a mixture of 1,2,3,3,3-pentafluoropropene and water. 
     
     
       14. The method of  claim 11 , wherein the impurity comprises a halocarbon. 
     
     
       15. The method of  claim 11 , wherein the impurity is miscible with 1,2,3,3,3-pentafluoropropene. 
     
     
       16. The method of  claim 11 , wherein the impurity is selected from the group consisting of hydrogen fluoride; 1,1,1,2,3,3-hexafluoropropane (HFC-236ea); 1,1,1,2,3-pentafluoropropane (HFC-245eb); hexafluoropropylene (HFP); 1,1,1,2-tetrafluoropropene (HFO-1234yf); and combinations thereof. 
     
     
       17. The method of  claim 11 , wherein the step of separating the azeotropic composition from the impurity is conducted by distillation. 
     
     
       18. The method of  claim 11 , wherein the azeotropic composition consists essentially of from about 0.1 to about 50 weight percent water and from about 50 to about 99.9 weight percent 1,2,3,3,3-pentafluoropropene. 
     
     
       19. A method for isolating 1,2,3,3,3-pentafluoropropene from an azeotropic mixture containing 1,2,3,3,3-pentafluoropropene and water, comprising separating 1,2,3,3,3-pentafluoropropene from the water, wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent. 
     
     
       20. The method of  claim 19 , wherein 1,2,3,3,3-pentafluoropropene is separated from water using a liquid-liquid phase separation. 
     
     
       21. The method of  claim 19 , wherein 1,2,3,3,3-pentafluoropropene is separated from water using distillation. 
     
     
       22. The method of  claim 19 , wherein 1,2,3,3,3-pentafluoropropene is separated from water using at least one drying media. 
     
     
       23. The method of claim  19  22, wherein the drying media is selected from the group consisting of a molecular sieve, silica alumina, and combinations thereof. 
     
     
       24. The method of  claim 19 , wherein water is removed first by liquid-liquid phase separation, then by a second method selected from the group consisting of distillation, one or more drying media, and combinations thereof. 
     
     
       25. The method of claim 6, further comprising:
 producing 2,3,3,3-tetrafluoro-1-propene from the 1,2,3,3,3-pentafluoropropene.    
     
     
       26. The method of claim 11, further comprising:
 producing 2,3,3,3-tetrafluoro-1-propene from the 1,2,3,3,3-pentafluoropropene.    
     
     
       27. The method of claim 11, wherein the mixture consists of water, 1,2,3,3,3-pentafluoropropene, and the impurity.  
     
     
       28. The method of claim 11, wherein the azeotropic or azeotrope-like composition has a boiling point of about −20° C.±0.5° C. at a pressure of about 14.3 psia±2 psia.  
     
     
       29. The method of claim 11, wherein the azeotropic or azeotrope-like composition has a boiling point of about −20° C. at a pressure of about 14.3 psia.  
     
     
       30. The method of claim 11, wherein the azeotropic or azeotrope-like composition has a boiling point of about −20.3° C. at a pressure of about 14.39 psia.  
     
     
       31. The method of claim 11,
 wherein the impurity comprises hydrogen fluoride.    
     
     
       32. The method of claim 11,
 wherein the impurity comprises 1,1,1,2,3,3-hexafluoropropane (HFC-236ea).    
     
     
       33. The method of claim 11,
 wherein the impurity comprises 1,1,1,2,3-pentafluoropropane (HFC-245eb).    
     
     
       34. The method of claim 11,
 wherein the impurity comprises hexafluoropropylene (HFP).    
     
     
       35. The method of claim 11,
 wherein the impurity comprises 1,1,1,2-tetrafluoropropene (HFO-1234yf).    
     
     
       36. The method of claim 19, further comprising:
 producing 2,3,3,3-tetrafluoro-1-propene from the 1,2,3,3,3-pentafluoropropene.    
     
     
       37. The method of claim 19, wherein the azeotropic mixture consists of water and 1,2,3,3,3-pentafluoropropene.  
     
     
       38. The method of claim 19, wherein the azeotropic mixture has a boiling point of about −20° C.±0.5° C. at a pressure of about 14.3 psia±2 psia.  
     
     
       39. The method of claim 19, wherein the azeotropic mixture has a boiling point of about −20° C. at a pressure of about 14.3 psia.  
     
     
       40. The method of claim 19, wherein the azeotropic mixture has a boiling point of about −20.3° C. at a pressure of about 14.39 psia.  
     
     
       41. A method, comprising:
 forming a blend consisting essentially of effective amounts of water and 1,2,3,3,3-pentafluoropropene;   wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent; and   producing 2,3,3,3-tetrafluoro-1-propene from the 1,2,3,3,3-pentafluoropropene.    
     
     
       42. The method of claim 41, wherein the blend consists of water and 1,2,3,3,3-pentafluoropropene.  
     
     
       43. The method of claim 41, wherein the blend has a boiling point of about −20° C.±0.5° C. at a pressure of about 14.3 psia±2 psia.  
     
     
       44. The method of claim 41, wherein the blend has a boiling point of about −20° C. at a pressure of about 14.3 psia.  
     
     
       45. The method of claim 41, wherein the blend has a boiling point of about −20.3° C. at a pressure of about 14.39 psia.  
     
     
       46. A method, comprising:
 removing 1,2,3,3,3-pentafluoropropene from a mixture containing 1,2,3,3,3-pentafluoropropene and at least one impurity, comprising:   adding water to the mixture in an effective amount to form an azeotropic or azeotrope-like composition of the 1,2,3,3,3-pentafluoropropene and the water;   wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent; and   separating the azeotropic composition from the impurity; and   producing 2,3,3,3-tetrafluoro-1-propene from the 1,2,3,3,3-pentafluoropropene.    
     
     
       47. The method of claim 46, wherein the azeotropic or azeotrope-like composition consists of water and 1,2,3,3,3-pentafluoropropene.  
     
     
       48. The method of claim 46, wherein the azeotropic or azeotrope-like composition has a boiling point of about −20° C.±0.5° C. at a pressure of about 14.3 psia±2 psia.  
     
     
       49. The method of claim 46, wherein the azeotropic or azeotrope-like composition has a boiling point of about −20° C. at a pressure of about 14.3 psia.  
     
     
       50. The method of claim 46, wherein the azeotropic or azeotrope-like composition has a boiling point of about −20.3° C. at a pressure of about 14.39 psia.  
     
     
       51. The method of claim 46, wherein the impurity is selected from the group consisting of hydrogen fluoride; 1,1,1,2,3,3-hexafluoropropane (HFC-236ea); 1,1,1,2,3-pentafluoropropane (HFC-245eb); hexafluoropropylene (HFP); 1,1,1,2-tetrafluoropropene (HFO-1234yf); and combinations thereof.  
     
     
       52. The method of claim 46,
 wherein the impurity comprises hydrogen fluoride.    
     
     
       53. The method of claim 46,
 wherein the impurity comprises 1,1,1,2,3,3-hexafluoropropane (HFC-236ea).    
     
     
       54. The method of claim 46,
 wherein the impurity comprises 1,1,1,2,3-pentafluoropropane (HFC-245eb).    
     
     
       55. The method of claim 46,
 wherein the impurity comprises hexafluoropropylene (HFP).    
     
     
       56. The method of claim 46,
 wherein the impurity comprises 1,1,1,2-tetrafluoropropene (HFO-1234yf).    
     
     
       57. A method, comprising:
 providing an azeotropic mixture containing 1,2,3,3,3-pentafluoropropene and water;   separating 1,2,3,3,3-pentafluoropropene from the water in the azeotropic mixture;   wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent; and   producing 2,3,3,3-tetrafluoro-1-propene from the 1,2,3,3,3-pentafluoropropene.    
     
     
       58. The method of claim 57, wherein the azeotropic mixture consists of water and 1,2,3,3,3-pentafluoropropene.  
     
     
       59. The method of claim 57, wherein the azeotropic mixture has a boiling point of about −20° C.±0.5° C. at a pressure of about 14.3 psia±2 psia.  
     
     
       60. The method of claim 57, wherein the azeotropic mixture has a boiling point of about −20° C. at a pressure of about 14.3 psia.  
     
     
       61. The method of claim 57, wherein the azeotropic mixture has a boiling point of about −20.3° C. at a pressure of about 14.39 psia.  
     
     
       62. The method of claim 57, wherein 1,2,3,3,3-pentafluoropropene is separated from water using a liquid-liquid phase separation.  
     
     
       63. The method of claim 57, wherein 1,2,3,3,3-pentafluoropropene is separated from water using distillation.  
     
     
       64. The method of claim 57, wherein 1,2,3,3,3-pentafluoropropene is separated from water using at least one drying media.  
     
     
       65. The method of claim 64, wherein the drying media is selected from the group consisting of a molecular sieve, silica alumina, and combinations thereof.  
     
     
       66. The method of claim 57, wherein water is removed first by liquid-liquid phase separation, then by a second method selected from the group consisting of distillation, one or more drying media, and combinations thereof.  
     
     
       67. A method, comprising:
 hydrogenating hexafluoropropylene to produce 1,1,1,2,3,3-hexafluoropropane;   dehydrofluorinating the 1,1,1,2,3,3-hexafluoropropane to produce an azeotropic mixture of 1,2,3,3,3-pentafluoropropene and water;   wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent;   separating 1,2,3,3,3-pentafluoropropene from the water in the azeotropic mixture; and   producing 2,3,3,3-tetrafluoro-1-propene from the 1,2,3,3,3-pentafluoropropene.    
     
     
       68. The method of claim 67, wherein the azeotropic mixture consists of water and 1,2,3,3,3-pentafluoropropene.  
     
     
       69. The method of claim 67, wherein the azeotropic mixture has a boiling point of about −20° C.±0.5° C. at a pressure of about 14.3 psia±2 psia.  
     
     
       70. The method of claim 67, wherein the azeotropic mixture has a boiling point of about −20° C. at a pressure of about 14.3 psia.  
     
     
       71. The method of claim 67, wherein the azeotropic mixture has a boiling point of about −20.3° C. at a pressure of about 14.39 psia.  
     
     
       72. A method, comprising:
 hydrogenating hexafluoropropylene to produce 1,1,1,2,3,3-hexafluoropropane;   dehydrofluorinating the 1,1,1,2,3,3-hexafluoropropane to produce 1,2,3,3,3-pentafluoropropene and water;   providing an azeotropic mixture containing 1,2,3,3,3-pentafluoropropene and water;   wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent; separating 1,2,3,3,3-pentafluoropropene from the water in the azeotropic mixture; and   producing 2,3,3,3-tetrafluoro-1-propene from the 1,2,3,3,3-pentafluoropropene.    
     
     
       73. The method of claim 72, wherein the azeotropic mixture consists of water and 1,2,3,3,3-pentafluoropropene.  
     
     
       74. The method of claim 72, wherein the azeotropic mixture has a boiling point of about −20° C.±0.5° C. at a pressure of about 14.3 psia±2 psia.  
     
     
       75. The method of claim 72, wherein the azeotropic mixture has a boiling point of about −20° C. at a pressure of about 14.3 psia.  
     
     
       76. The method of claim 72, wherein the azeotropic mixture has a boiling point of about −20.3° C. at a pressure of about 14.39 psia.  
     
     
       77. A method, comprising:
 hydrogenating hexafluoropropylene to produce 1,1,1,2,3,3-hexafluoropropane;   dehydrofluorinating the 1,1,1,2,3,3-hexafluoropropane to produce 1,2,3,3,3-pentafluoropropene and water;   removing an azeotropic mixture of 1,2,3,3,3-pentafluoropropene and water;   wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent   separating the 1,2,3,3,3-pentafluoropropene from the water in the azeotropic mixture; and   producing 2,3,3,3-tetrafluoro-1-propene from the 1,2,3,3,3-pentafluoropropene.    
     
     
       78. The method of claim 77, wherein the azeotropic mixture consists of water and 1,2,3,3,3-pentafluoropropene.  
     
     
       79. The method of claim 77, wherein the azeotropic mixture has a boiling point of about −20° C.±0.5° C. at a pressure of about 14.3 psia±2 psia.  
     
     
       80. The method of claim 77, wherein the azeotropic mixture has a boiling point of about −20° C. at a pressure of about 14.3 psia.  
     
     
       81. The method of claim 77, wherein the azeotropic mixture has a boiling point of about −20.3° C. at a pressure of about 14.39 psia.  
     
     
       82. A method, comprising:
 dehydrofluorinating 1,1,1,2,3,3-hexafluoropropane to produce 1,2,3,3,3-pentafluoropropene and water;   removing an azeotropic mixture of 1,2,3,3,3-pentafluoropropene and water;   wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent;   separating the 1,2,3,3,3-pentafluoropropene from the water in the azeotropic mixture; and   producing 2,3,3,3-tetrafluoro-1-propene from the 1,2,3,3,3-pentafluoropropene.    
     
     
       83. The method of claim 82, wherein the azeotropic mixture consists of water and 1,2,3,3,3-pentafluoropropene.  
     
     
       84. The method of claim 82, wherein the azeotropic mixture has a boiling point of about −20° C.±0.5° C. at a pressure of about 14.3 psia±2 psia.  
     
     
       85. The method of claim 82, wherein the azeotropic mixture has a boiling point of about −20° C. at a pressure of about 14.3 psia.  
     
     
       86. The method of claim 82, wherein the azeotropic mixture has a boiling point of about −20.3° C. at a pressure of about 14.39 psia.  
     
     
       87. A method, comprising:
 forming an azeotropic composition consisting essentially of effective amounts of water and 1,2,3,3,3-pentafluoropropene;   producing 2,3,3,3-tetrafluoro-1-propene from the 1,2,3,3,3-pentafluoropropene.    
     
     
       88. A method of claim 87, wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent.  
     
     
       89. A method, comprising:
 hydrogenating hexafluoropropylene to produce 1,1,1,2,3,3-hexafluoropropane;   dehydrofluorinating the 1,1,1,2,3,3-hexafluoropropane to produce 1,2,3,3,3-pentafluoropropene and water;   providing an azeotropic mixture containing 1,2,3,3,3-pentafluoropropene and water; and   producing 2,3,3,3-tetrafluoro-1-propene from the 1,2,3,3,3-pentafluoropropene.    
     
     
       90. A method of claim 89, wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent in the azeotropic mixture.  
     
     
       91. The method of claim 89, wherein the azeotropic mixture consists of water and 1,2,3,3,3-pentafluoropropene.  
     
     
       92. The method of claim 89, wherein the azeotropic mixture has a boiling point of about −20° C.±0.5° C. at a pressure of about 14.3 psia±2 psia.  
     
     
       93. The method of claim 89, wherein the azeotropic mixture has a boiling point of about −20° C. at a pressure of about 14.3 psia.  
     
     
       94. The method of claim 89, wherein the azeotropic mixture has a boiling point of about −20.3° C. at a pressure of about 14.39 psia.  
     
     
       95. A method, comprising:
 hydrogenating hexafluoropropylene to produce 1,1,1,2,3,3-hexafluoropropane;   dehydrofluorinating the 1,1,1,2,3,3-hexafluoropropane to produce 1,2,3,3,3-pentafluoropropene and water;   removing an azeotropic mixture of 1,2,3,3,3-pentafluoropropene and water;   separating the 1,2,3,3,3-pentafluoropropene from the water in the azeotropic mixture; and   producing 2,3,3,3-tetrafluoro-1-propene from the 1,2,3,3,3-pentafluoropropene.    
     
     
       96. A method of claim 95, wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent in the azeotropic mixture.  
     
     
       97. The method of claim 95, wherein the azeotropic mixture consists of water and 1,2,3,3,3-pentafluoropropene.  
     
     
       98. The method of claim 95, wherein the azeotropic mixture has a boiling point of about −20° C.±0.5° C. at a pressure of about 14.3 psia±2 psia.  
     
     
       99. The method of claim 95, wherein the azeotropic mixture has a boiling point of about −20° C. at a pressure of about 14.3 psia.  
     
     
       100. The method of claim 95, wherein the azeotropic mixture has a boiling point of about −20.3° C. at a pressure of about 14.39 psia.  
     
     
       101. A method, comprising:
 dehydrofluorinating 1,1,1,2,3,3-hexafluoropropane to produce 1,2,3,3,3-pentafluoropropene and water;   removing an azeotropic mixture of 1,2,3,3,3-pentafluoropropene and water;   separating the 1,2,3,3,3-pentafluoropropene from the water in the azeotropic mixture; and   producing 2,3,3,3-tetrafluoro-1-propene from the 1,2,3,3,3-pentafluoropropene.    
     
     
       102. A method of claim 101, wherein water is provided in an amount from about 0.25 to about 11 weight percent and 1,2,3,3,3-pentafluoropropene is provided in an amount from about 89 to about 99.75 weight percent.  
     
     
       103. The method of claim 101, wherein the azeotropic mixture consists of water and 1,2,3,3,3-pentafluoropropene.  
     
     
       104. The method of claim 101, wherein the azeotropic mixture has a boiling point of about −20° C.±0.5° C. at a pressure of about 14.3 psia±2 psia.  
     
     
       105. The method of claim 101, wherein the azeotropic mixture has a boiling point of about −20° C. at a pressure of about 14.3 psia.  
     
     
       106. The method of claim 101, wherein the azeotropic mixture has a boiling point of about −20.3° C. at a pressure of about 14.39 psia.  
     
     
       107. A method, comprising:
 dehydrofluorinating 1,1,1,2,3,3-hexafluoropropane to produce 1,2,3,3,3-pentafluoropropene and water;   removing an azeotropic mixture of 1,2,3,3,3-pentafluoropropene and water;   separating the 1,2,3,3,3-pentafluoropropene from the water in the azeotropic mixture; and   producing a hydrofluoroolefin from the 1,2,3,3,3-pentafluoropropene.    
     
     
       108. The method of claim 107,
 wherein the hydrofluoroolefin is 2,3,3,3-tetrafluoro-1-propene.