1,1,1,2,2,3,3,4,4-Nonafluoro-6-iodohexane

Red liquid

Liquid

A 400 mL shaker tube was charged with perfluorobutylethyl iodide (PFBEI) (75 g) and VAZO 64 (1.5 g) as in Example 1. After cool evacuation, ethylene (6 g) and tetrafluoroethylene (25 g) were added. The resulting mixture was heated to 80° C. for 20 hours. Reaction mixtures from 10 identical runs were combined and the unreacted perfluorobutylethyl iodide was recovered by vacuum distillation at room temperature. The remaining solid (648 g) was extracted with CH3CN (10.x.300 mL). The combined CH3CN extracts were concentrated and distilled at reduced pressure to give iodide 1, 1, 2, 2, 5, 5, 6, 6-octahydroperfluoro-1-iododecane. The solid remaining after CH3CN extraction was mainly 1, 1, 2, 2, 5, 5, 6, 6, 9, 9, 10, 10-dodecahydroperfluoro-1-iodotetradecane and higher oligomers. The product 1, 1, 2, 2, 5, 5, 6, 6-octahydroperfluoro-1-iododecane was characterized by H NMR and F NMR as shown below.1, 1, 2, 2, 5, 5, 6, 6-Octahydroperfluoro-1-iododecane: mp 72-74° C.:H NMR (CDCl3) 2.36 (m, 4H), 2.69 (m, 2H), 3.25 (m, 2H) ppm.F NMR (CDCl3) -81.5 (tt, J=10, 3 Hz, 3F), -115.3 (m, 2F), -115.7 (m, 4F), -124.7 (m, 2F), -126.4 (m, 2F) ppm.A mixture of 1, 1, 2, 2, 5, 5, 6, 6-octahydroperfluoro-1-iododecane (12 g) prepared as described above, and oleum (15percent SO3, 21 5 mL) was heated to 60° C. for 2 h. A Na2SO3 solution (4 g, in water 100 mL) was slowly added to the reaction mixture at 60° C. bath between 65° C. to 90° C. internal temperatures. The resulting mixture was heated to 90° C. for 30min. After being cooled to room temperature, a solid was precipitated. The liquid was decanted and the solid was dissolved in ether (150 mL) and washed with Na2SO3 (1 M, 20 mL), water (2.x.20 mL), NaCl (sat. 20 mL), dried over anhydrous Na2SO4, concentrated and dried on vacuum to give to give a residue which was further purified by distillation to give an off-white solid 6.2 g, bp, 65-79° C. at 2 torr (267 Pa) as 1, 1, 2, 2, 5, 5, 6, 6-octahydroperfluoro-1-decanol. The product was characterized by MS, H NMR and F NMR as shown below.MS (m/e) 392 (M+, 0.16percent), 372 (3.3percent), 342 (60percent), 323 (53percent), 223 (29percent), 95 (100percent). H NMR (CDCl3) 1.58 (s, 1 H), 2.36 (m, 6H), 3.97 (t, J=7 Hz, 2H) ppm. F NMR (CDCl3) -81.5 (it, J=9.5, 3 Hz, 3F), -114.1 (m, 2F), -115.4 (m, 2F), -116.0 (m, 2F), -124.8 (m, 2F), -126.4 (m, 2F) ppm.In a 100 mL flask equipped with a stir bar, condenser and nitrogen blanket, charged under nitrogen 1, 1, 2, 2, 5, 5, 6, 6-octahydroperfluoro-1-decanol (3 g) prepared as described above, and phosphorus pentoxide (0.56 g). The mixture was heated to 100° C. for 18 hours. The reaction mixture was cooled to 86° C. and warm water (80° C., 16.5 g) was added. The resulting mixture was stirred for 1 hour and ammonium hydroxide (ammonia 28percent, 2.19 g) was added. The mixture was stirred for another hour and transferred to a jar when it was still hot. The product was calculated to contain 19.2 w/w percent solids. Surface tension was-measured using Test Method 2. The results are in Table 5.Production Example 85; 7.0 g of l-iodo-3, 3, 4 , 4 , 5, 5, 6, 6, 6-nonafluorohexane and 4.4 g of methyl (3, 3, 3-trifluoropropylsulfonyl) acetate

Intermediates

Molecular Weight:373.99
XLogP3:4.8
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:4
Exact Mass:373.92140
Monoisotopic Mass:373.92140
Heavy Atom Count:16
Complexity:243
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes