Method of making an olefin polymerization catalyst activator
A method for preparing ammonium tetrakis(pentafluorophenyl)borate salt comprising reacting a secondary amine with an aldehyde to form an iminium ion; hydrogenating the iminium ion by reaction with a reducing agent to form a tertiary amine; reacting the tertiary amine with a mineral acid to form an amine salt; and reacting the amine salt with K[B(C 6 F 5 ) 4 ], Li[B(C 6 F 5 ) 4 ], or combinations thereof to form an ammonium tetrakis(pentafluorophenyl)borate salt, wherein the secondary amine is derived from a non-animal source and the aldehyde has seven or more carbon atoms; wherein the ammonium tetrakis(pentafluorophenyl)borate salt is characterized by a solubility at 25° C. in hexane, cyclohexane or methylcyclohexane of at least 10 weight percent; and wherein the tertiary amine has a molecular weight of at least 450 g/mole is provided.
1. A method for preparing ammonium tetrakis(pentafluorophenyl)borate salt comprising:
reacting a secondary amine with an aldehyde to form an iminium ion;
hydrogenating the iminium ion by reaction with a reducing agent to form a tertiary amine; reacting the tertiary amine with mineral acid to form an amine salt; and
reacting the amine salt with K[B(C 6 F 5 ) 4 ], Li[B(C 6 F 5 ) 4 ], or a combination thereof, to form an ammonium tetrakis(pentafluorophenyl)borate salt,
wherein the secondary amine is derived from a non-animal source and the aldehyde has seven or more carbon atoms;
wherein the ammonium tetrakis(pentafluorophenyl)borate salt is characterized by a solubility at 25° C. in hexane, cyclohexane or methylcyclohexane of at least 10 weight percent; and
wherein the tertiary amine has a molecular weight of at least 450 g/mole.
2. The method according to claim 1 , wherein the reacting a secondary amine with an aldehyde occurs under conditions to drive the reaction to completion.
3. The method according to claim 2 , wherein the reacting a secondary amine with an aldehyde occurs in the presence of a dehydrating agent selected from the group consisting of MgSO 4 , Na 2 SO 4 , CaCl 2 , molecular sieves, activated alumina, silica gel, and combinations thereof.
4. The method according to claim 1 , wherein the reducing agent is selected from the group consisting of sodium triacetoxyborohydride. NaBH 4 , NaBH 3 CN, Zn(BH 4 )2, ((C 6 H 5 ) 3 P) 2 Cu(BH 4 ), NR 4 BH 4 , BH 3 , and combinations thereof.
5. The method according to claim 1 , wherein the reducing agent is sodium triacetoxyborohydride.
6. The method according to claim 1 , wherein the aldehyde is C 7 H 14 0.
7. The method according to claim 1 , wherein the aldehyde is C 12 H 24 0.
8. The method according to claim 6 , wherein the reacting the amine salt with K[B(C 6 F 5 ) 4 ], Li[B(C 6 F 5 ) 4 ], or a combination thereof to form the ammonium tetrakis(pentafluorophenyl)borate salt has at least an 80% yield based on the weight of potassium tetrakis(pentafluorophenyl)borate (K[B(C 6 F 5 ) 4 ]).
9. The method according to claim 7 , wherein the reacting the amine salt with K[B(C 6 F 5 ) 4 ], Li[B(C 6 F 5 ) 4 ], or a combination thereof to form the ammonium tetrakis(pentafluorophenyl)borate salt has at least an 80% yield based on the weight of potassium tetrakis(pentafluorophenyl)borate (K[B(C 6 F 5 ) 4 ]).
10. The method according to claim 6 , wherein the ammonium tetrakis(pentafluorophenyl)borate salt is soluble in methylcyclohexane at levels greater than 25 wt %.
11. The method according to claim 7 , wherein the ammonium tetrakis(pentafluorophenyl)borate salt is soluble in methylcyclohexane at levels greater than 25 wt %.