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US4180386A Expired / Lapsed US ⏱️ 0.0 years remaining

Hexacoordinated transition metal compounds containing at least one polyfluoroalkyl substituent

Assignee: Octel America Inc
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Filing: 1978-05-19
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Granted: 1979-12-25
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Expires: 1998-05-19
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Abstract

Abstract Hexacoordinated transition metal compounds, useful as antiknocks, having the structure ##STR1## wherein M is a divalent metal selected from the group Mn, Fe, Co and Ni, L 1 and L 2 are the same or different chelate-forming β-diketone groups having from 5 to 20 carbon atoms, one or both of L 1 and L 2 having at least one polyfluoroalkyl group, --CF 2 X, adjacent to the carbonyl group, X is selected from the group H, F, Cl, phenyl, C 1 -C 6 alkyl and C n F 2n Y, n is 1 to 6, Y is H, F, or Cl, L 3 is a ligand having the structure A-Z-B, wherein A and B are the same or different members of the group --NH 2 , --NHR 5 , --NR 5 R 6 , OH, OR 5 , SH, SR 5 and PR 5 R 6 , R 5 and R 6 are the same or different members of the group C 1 to C 4 alkyl, and Z is a divalent hydrocarbyl group having 2 to 10 carbon atoms selected from a member of the group alkylene, phenylene and cycloalkylene, each member providing 2 or 3 carbon atoms between A and B, with the proviso that when Z is phenylene, the number of carbon atoms between A and B is 2.

Inventors

  • 👤 William B. McCormack
  • 👤 Charles A. Sandy

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 03:42
CPC Classifications
C; C07; C07F; C07F15/00; C07F15/06; C07F15/065; C07F13/00; C07F13/005; C07F15/02; C07F15/025; C07F15/04; C07F15/045

Claims Analysis

Total Claims: 31
Claim 1
Independent Claim 217 words
A compound having the structure ##STR6## wherein M is a divalent metal selected from the group Mn, Fe, Co and Ni, L 1 and L 2 are the same or different chelate-forming β-diketone groups having from 5 to 20 carbon atoms, one or both of L 1 and L 2 having at least one polyfluoroalkyl group, --CF 2 X, adjacent to the carbonyl group, X is selected from the group H, F, Cl, phenyl, C 1 -C 6 alkyl and C n F 2n Y, n is 1 to 6, Y is H, F, or Cl, L 3 is a ligand having the structure, A-Z-B, wherein A and B are the same or different members of the group --NH 2 , --NHR 5 , --NR 5 R 6 , OH, OR 5 , SH, SR 5 and PR 5 R 6 , R 5 and R 6 are the same or different members of the group C 1 to C 4 alkyl, and Z is a divalent hydrocarbyl group having 2 to 10 carbon atoms selected from a member of the group alkylene, phenylene and cycloalkylene, each member providing 2 or 3 carbon atoms between A and B, with the proviso that when Z is phenylene, the number of carbon atoms between A and B is 2.
Claim 2
Dependent Claim 217 words
A compound having the structure ##STR6## wherein M is a divalent metal selected from the group Mn, Fe, Co and Ni, L 1 and L 2 are the same or different chelate-forming β-diketone groups having from 5 to 20 carbon atoms, one or both of L 1 and L 2 having at least one polyfluoroalkyl group, --CF 2 X, adjacent to the carbonyl group, X is selected from the group H, F, Cl, phenyl, C 1 -C 6 alkyl and C n F 2n Y, n is 1 to 6, Y is H, F, or Cl, L 3 is a ligand having the structure, A-Z-B, wherein A and B are the same or different members of the group --NH 2 , --NHR 5 , --NR 5 R 6 , OH, OR 5 , SH, SR 5 and PR 5 R 6 , R 5 and R 6 are the same or different members of the group C 1 to C 4 alkyl, and Z is a divalent hydrocarbyl group having 2 to 10 carbon atoms selected from a member of the group alkylene, phenylene and cycloalkylene, each member providing 2 or 3 carbon atoms between A and B, with the proviso that when Z is phenylene, the number of carbon atoms between A and B is 2.
Claim 3
Dependent Claim 19 words
A compound according to claim 1 wherein each of L 1 and L 2 is the difluoroacetylacetonyl β-diketone group.
Claim 4
Dependent Claim 19 words
A compound according to claim 1 wherein each of L 1 and L 2 is the chlorodifluoroacetylacetonyl β-diketone group.
Claim 5
Dependent Claim 34 words
A compound according to claim 1 wherein each of L 1 and L 2 is ##STR7## Z is CH 2 CH 2 and each of A and B is N(CH 3 ) 2 .
Claim 6
Dependent Claim 19 words
A compound according to claim 1 wherein each of L 1 and L 2 is a hexafluoroacetylacetonyl β-diketone group.
Claim 7
Dependent Claim 14 words
A compound according to claim 5 wherein Z is CH 2 CH 2 .
Claim 8
Dependent Claim 16 words
A compound according to claim 6 wherein each of A and B is CH 3 O.
Claim 9
Dependent Claim 20 words
A compound according to claim 6 wherein A is CH 3 O and B is N(CH 3 ) 2 .
Claim 10
Dependent Claim 20 words
A compound according to claim 6 wherein A is CH 3 S and B is N(CH 3 ) 2 .
Claim 11
Dependent Claim 18 words
A compound according to claim 6 wherein each of A and B is SC 2 H 5 .
Claim 12
Dependent Claim 27 words
A compound according to claim 6 wherein Z is C(CH 3 ) 2 C(CH 3 ) 2 and each of A and B is NH 2 .
Claim 13
Dependent Claim 79 words
A compound according to claim 1 having the structure ##STR8## wherein: R 1 , R 2 , R 3 , and R 4 are each individually selected from C 1 to C 3 perfluoroalkyl and C 1 to C 6 alkyl with at least one of R 1 , R 2 , R 3 , and R 4 being a perfluoroalkyl group, and R 5 and R 6 are selected from hydrogen and C 1 to C 4 alkyl.
Claim 14
Dependent Claim 14 words
A compound according to claim 12 wherein M is selected from Co and Ni.
Claim 15
Dependent Claim 10 words
A compound according to claim 13 wherein M is Co.
Claim 16
Dependent Claim 10 words
A compound according to claim 13 wherein M is Ni.
Claim 17
Dependent Claim 24 words
A compound according to claim 12 wherein R 1 , R 2 , R 3 , and R 4 are each CF 3 .
Claim 18
Dependent Claim 17 words
A compound according to claim 12 wherein R 5 and R 6 are each CH 3 .
Claim 19
Dependent Claim 14 words
A compound according to claim 12 wherein Z is --C 2 H 4 --.
Claim 20
Dependent Claim 24 words
A compound according to claim 16 wherein R 5 and R 6 are each CH 3 and Z is --C 2 H 4 --.
Claim 21
Dependent Claim 42 words
A compound according to claim 14 wherein each of R 1 , R 2 , R 3 , and R 4 is CF 3 , R 5 and R 6 are each CH 3 and Z is C 2 H 4 .
Claim 22
Dependent Claim 41 words
A compound according to claim 15 wherein each of R 1 , R 2 , R 3 and R 4 is CF 3 , R 5 and R 6 are each CH 3 and Z is C 2 H 4 .
Claim 23
Dependent Claim 46 words
A compound according to claim 14 wherein R 1 and R 3 are each (CH 3 ) 3 C, R 2 and R 4 are each CF 3 , R 5 and R 6 are each CH 3 and Z is C 2 H 4 .
Claim 24
Dependent Claim 44 words
A compound according to claim 14 wherein R 1 and R 3 are each CF 3 , R 2 and R 4 are each CH 3 , R 5 and R 6 are each CH 3 and Z is C 2 H 4 .
Claim 25
Dependent Claim 46 words
A compound according to claim 14 wherein each of R 1 , R 2 , R 3 , and R 4 is CF 3 , R 5 and R 6 are each CH 3 and Z is CH 2 C(CH 3 ) 2 CH 2 .
Claim 26
Dependent Claim 44 words
A compound according to claim 14 wherein R 1 and R 2 are each CH 3 , R 3 and R 4 are each CF 3 , R 5 and R 6 are each CH 3 and Z is C 2 H 4 .
Claim 27
Dependent Claim 50 words
A compound according to claim 14 wherein R 1 and R 3 are each CH 3 , R 2 is CH 3 CH(CH 3 )CH 2 , R 4 is CF 3 , R 5 and R 6 are each CH 3 and Z is C 2 H 4 .
Claim 28
Dependent Claim 44 words
A compound according to claim 15 wherein R 1 and R 3 are each CH 3 , R 2 and R 4 are each CF 3 , R 5 and R 6 are each CH 3 and Z is C 2 H 4 .
Claim 29
Dependent Claim 45 words
A compound according to claim 15 wherein each of R 1 , R 2 , R 3 and R 4 is CF 3 , R 5 and R 6 are each CH 3 and Z is CH 2 C(CH 3 ) 2 CH 2 .
Claim 30
Dependent Claim 20 words
A concentrate comprising about 5% to 50% by weight of the compound of claim 1 in an organic solvent therefor.
Claim 31
Dependent Claim 35 words
A fuel composition comprising a fuel boiling in the gasoline boiling range containing an amount of a compound of claim 1 to provide at least about 0.01 gram of metal per gallon of fuel composition.

References Cited (Backward Citations)

GB287192A Cited
US2144654A Cited
US2156918A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-12-24 1983-06-25 1983-12-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-12-24 1987-06-25 1987-12-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-12-24 1991-06-25 1991-12-25 $7700.00 Window Closed / Lapsed

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