US5496960A
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Process for production of bis-(pentafluorophenyl) borane and use thereof for producition of base free zwitterionic homogeneous Ziegler-Natta olefin polymerization catalysts
Assignee: University of Guelph
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Filing: 1995-01-20
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Granted: 1996-03-05
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Expires: 2015-01-20
Abstract
Abstract There is disclosed a new boron-containing compounds such as bis-(pentafluorophenyl)borane, (C6F5)2BH and related compounds and a method for producing the compounds. The new borane is suitable for use as a hydroboration reagent for the rapid hydroboration of alkenes and alkynes. The borane is also suitable for use as a hydroboration reagent to produce useful boron reagents that can be used in Ziegler-Natta homogeneous olefin polymerization catalyst systems. Specifically, the borane reagent can be used to produce Cp2Zr{ eta 3-CH(C6H5)[( mu -H)B(C6F5)2]}, which exhibits an efficacy for polymerization of ethylene.
Inventors
- 👤 Warren E. Piers
- 👤 Rupert E. von Haken Spence
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 22:10
CPC Classifications
C; C07; C07F; C07F17/00; C07F5/00; C07F5/02; C07F5/027; C08; C08F; C08F10/00; C08F4/00; C08F4/42; C08F4/44; C08F4/60; C08F4/62; C08F4/64; C08F4/659; C08F4/65908; C08F4/6592; C08F4/65922; C08F4/65925
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
54 words
A compound having the formula [(C 6 R 5 ) 2 BH] n , wherein n is selected from the group consisting of 1 and 2, and wherein R is selected from the group consisting of fluorine (F), hydrogen (H), (trifluoromethyl) (CF 3 ) groups, and combinations thereof but not consisting entirely of H.
Claim 2
Dependent Claim
54 words
A compound having the formula [(C 6 R 5 ) 2 BH] n , wherein n is selected from the group consisting of 1 and 2, and wherein R is selected from the group consisting of fluorine (F), hydrogen (H), (trifluoromethyl) (CF 3 ) groups, and combinations thereof but not consisting entirely of H.
Claim 3
Dependent Claim
10 words
The compound according to claim 1 wherein R is F.
Claim 4
Dependent Claim
23 words
The compound according to claim 2 characterized by infrared absorption bands at about 1395 cm -1 and at about 1550 cm -1 .
Claim 5
Dependent Claim
43 words
The compound according to claim 2 characterized by 19 F NMR major peaks at -134.8 (2F), -148.0 (1 F) due to a dimer species, n=2, and minor peaks at -160.7 (2F), -130.5 (2F), -143.4 (1F) and -161.7 (2F) due to monomer species, n=1.
Claim 6
Dependent Claim
43 words
The compound according to claim 1 wherein [(C 6 R 5 ) 2 BH] n is [[3,5-(CR' 3 ) 2 C 6 R" 3 ] 2 BH] n , and R' and R" are selected from the group consisting of F and H.
Claim 7
Dependent Claim
14 words
The compound according to claim 5 wherein R' is F and R" is H.
Claim 8
Independent Claim
86 words
A method of producing [(C 6 F 5 ) 2 BH] 2 , of the steps of: providing an amount of ClB(C 6 F 5 ) 2 ; mixing said ClB(C 6 F 5 ) 2 with a source of hydride in a temperature range from about -78° C. to about room temperature to produce a solution in which a precipitate comprising [(C 6 F 5 ) 2 BH] 2 is formed; and isolating said [(C 6 F 5 ) 2 BH] 2 from said solution.
Claim 9
Independent Claim
86 words
A method of producing [(C 6 F 5 ) 2 BH] 2 , of the steps of: providing an amount of ClB(C 6 F 5 ) 2 ; mixing said ClB(C 6 F 5 ) 2 with a source of hydride in a temperature range from about -78° C. to about room temperature to produce a solution in which a precipitate comprising [(C 6 F 5 ) 2 BH] 2 is formed; and isolating said [(C 6 F 5 ) 2 BH] 2 from said solution.
Claim 10
Dependent Claim
52 words
The method according to claim 7 wherein said source of hydride is selected from the group consisting of R 3 MH and R 2 (Cl)MH, wherein R is selected from the group consisting of alkyl and aryl functional groups and M is selected from the group consisting of Si, Ge and Sn.
Claim 11
Dependent Claim
43 words
The method according to claim 7 wherein said source of hydride is selected from the group consisting of Cp 2 MH 2 and Cp 2 M(Cl)H, wherein Cp is cyclopentadienyl and M is selected from the group consisting of Ti, Zr and Hf.
Claim 12
Dependent Claim
28 words
The method according to claim 7 wherein said source of hydride is a metal hydride selected from the group consisting of Group 4 and Group 14 metal hydrides.
Claim 13
Dependent Claim
29 words
The method according to claim 7 wherein said source of hydride is selected from the group consisting of (Cl)HSiMe 2 , [Cp 2 Zr(Cl)H] n and Bu 3 SnH.
Claim 14
Independent Claim
103 words
A method of hydroborating alkenes by reaction with (C 6 F 5 ) 2 BH, comprising: providing a quantity of [(C 6 F 5 ) 2 BH] 2 and a quantity of an alkene; and mixing said quantity of [(C 6 F 5 ) 2 BH] 2 with a dry aromatic organic solvent to produce a suspension comprising an equilibrium mixture of [(C 6 F 5 ) 2 BH] 2 and (C 6 F 5 ) 2 BH and mixing therewith said quantity of said alkene, such that said alkene reacts with said (C 6 F 5 ) 2 BH to undergo hydroboration.
Claim 15
Independent Claim
103 words
A method of hydroborating alkenes by reaction with (C 6 F 5 ) 2 BH, comprising: providing a quantity of [(C 6 F 5 ) 2 BH] 2 and a quantity of an alkene; and mixing said quantity of [(C 6 F 5 ) 2 BH] 2 with a dry aromatic organic solvent to produce a suspension comprising an equilibrium mixture of [(C 6 F 5 ) 2 BH] 2 and (C 6 F 5 ) 2 BH and mixing therewith said quantity of said alkene, such that said alkene reacts with said (C 6 F 5 ) 2 BH to undergo hydroboration.
Claim 16
Dependent Claim
29 words
The method according to claim 12 wherein said alkene and said dry organic solvent are reacted together in the temperature range from about -78° C. to about room temperature.
Claim 17
Dependent Claim
45 words
The method according to claim 13 wherein said alkene is R 1 R 2 C=CR 3 R 4 , wherein R 1 , R 2 , R 3 and R 4 are selected from the group consisting of H, and alkyl and aryl functional groups.
Claim 18
Independent Claim
104 words
A method of hydroborating alkynes by reaction with (C 6 F 5 ) 2 BH, comprising: providing a quantity of [(C 6 F 5 ) 2 BH] 2 and a quantity of an alkyne; and mixing said quantity of [(C 6 F 5 ) 2 BH] 2 with a dry aromatic organic solvent to produce a suspension comprising an equilibrium mixture of [(C 6 F 5 ) 2 BH ] 2 and (C 6 F 5 ) 2 BH and mixing therewith said quantity of said alkyne, such that said alkyne reacts with said (C 6 F 5 ) 2 BH to undergo hydroboration.
Claim 19
Independent Claim
104 words
A method of hydroborating alkynes by reaction with (C 6 F 5 ) 2 BH, comprising: providing a quantity of [(C 6 F 5 ) 2 BH] 2 and a quantity of an alkyne; and mixing said quantity of [(C 6 F 5 ) 2 BH] 2 with a dry aromatic organic solvent to produce a suspension comprising an equilibrium mixture of [(C 6 F 5 ) 2 BH ] 2 and (C 6 F 5 ) 2 BH and mixing therewith said quantity of said alkyne, such that said alkyne reacts with said (C 6 F 5 ) 2 BH to undergo hydroboration.
Claim 20
Dependent Claim
38 words
The method according to claim 15 wherein said alkyne is dried, and said alkyne and said dry organic solvent are reacted together in a temperature range from about -78° C. to about room temperature under an inert atmosphere.
Claim 21
Dependent Claim
35 words
The method according to claim 15 wherein said alkyne is R 1 CCR 2 , wherein R 1 and R 2 are selected from the group consisting of H, and alkyl and aryl functional groups.
Claim 22
Dependent Claim
37 words
A compound having the formula Cp 2 Zr{R'"[(μ-H)B(C 6 F 5 ) 2 ]} wherein Cp is cyclopentadienyl and R'" is selected from the group consisting of CH 2 and (η 3 -CH(C 6 H 5 )).
Claim 23
Dependent Claim
37 words
A compound having the formula Cp 2 Zr{R'"[(μ-H)B(C 6 F 5 ) 2 ]} wherein Cp is cyclopentadienyl and R'" is selected from the group consisting of CH 2 and (η 3 -CH(C 6 H 5 )).
Claim 24
Independent Claim
98 words
A method of producing chelating bis borane co-catalysts by hydroboration of terminal alkynes by reaction with (C 6 F 5 ) 2 BH, comprising: providing an amount of a terminal alkyne having a formula RC≡CH wherein R is selected from the group consisting of tertiary butyl, and phenyl and alkyl organic functional groups; and reacting said terminal alkyne with an effective amount of (C 6 F 5 ) 2 BH to cause said terminal alkyne to undergo hydroboration to produce chelating bis borane co-catalysts having a formula RCH 2 CH[B(C 6 F 5 ) 2 ] 2 .
Claim 25
Independent Claim
98 words
A method of producing chelating bis borane co-catalysts by hydroboration of terminal alkynes by reaction with (C 6 F 5 ) 2 BH, comprising: providing an amount of a terminal alkyne having a formula RC≡CH wherein R is selected from the group consisting of tertiary butyl, and phenyl and alkyl organic functional groups; and reacting said terminal alkyne with an effective amount of (C 6 F 5 ) 2 BH to cause said terminal alkyne to undergo hydroboration to produce chelating bis borane co-catalysts having a formula RCH 2 CH[B(C 6 F 5 ) 2 ] 2 .
References Cited (Backward Citations)
No citation records indexed.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1999-03-05 | 1999-09-04 | 2000-03-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-03-05 | 2003-09-04 | 2004-03-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-03-05 | 2007-09-04 | 2008-03-05 | $7700.00 | Window Closed / Lapsed |