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US4684734A Expired / Lapsed US ⏱️ 0.0 years remaining

Method for manufacture or organic fluorine compounds

Assignee: Nippon Shokubai Co Ltd
•
Filing: 1985-09-13
•
Granted: 1987-08-04
•
Expires: 2005-09-13
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Abstract

Abstract Organic fluorine compounds such as pentafluorobenzonitrile, tetrafluorophthalonitriles, and pentafluoropyridine are produced by a method which comprises causing a chloro- or bromo-organic compound to react with a fluorinating agent such as an alkali metal fluoride in benzonitrile as a solvent at temperatures in the range of 190° to 400° C. under at least spontaneously generated pressure.

Inventors

  • 👤 Osamu Kaieda
  • 👤 Masaru Awashima
  • 👤 Isao Okitaka
  • 👤 Toshiaki Nakamura

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 13:08
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/84; C07B; C07B39/00; C07C; C07C17/00; C07C17/093; C07C17/20; C07C17/202; C07C17/208; C07C201/00; C07C201/06; C07C201/12; C07C253/00; C07C253/30; C07D213/61

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 209 words
A method for the manufacture of an organic fluorine compound represented by the general formula VIII: ##STR15## wherein V denotes N, CW, or CF where W is Cl, Br, CN or NO 2 , p denotes an integer of the value of 0 to 4, and q denotes an integer of the value of 1 to 5, providing that the sum of p and q is an integer of the value of not more than 5, which comprises causing a chloro- or bromo-organic compound represented by the general forumla I: ##STR16## wherein X denotes N, --CY or --CZ where Y is Cl or Br and Z is F, CN or NO 2 , m denotes an integer of the value of 1 to 5, and n an integer of the value of 0 to 4, providing that the sum of m and n is an integer of the value of not more than 5 to react with at least one fluorinating agent selected from the group consisting of alkali metal fluorides and alkaline earth metal fluorides in benzonitrile as a solvent at temperatures in the range of 190° to 400° C. under at least spontaneously generated pressure whereby at least one of said Y halogens is replaced by F.
Claim 2
Independent Claim 209 words
A method for the manufacture of an organic fluorine compound represented by the general formula VIII: ##STR15## wherein V denotes N, CW, or CF where W is Cl, Br, CN or NO 2 , p denotes an integer of the value of 0 to 4, and q denotes an integer of the value of 1 to 5, providing that the sum of p and q is an integer of the value of not more than 5, which comprises causing a chloro- or bromo-organic compound represented by the general forumla I: ##STR16## wherein X denotes N, --CY or --CZ where Y is Cl or Br and Z is F, CN or NO 2 , m denotes an integer of the value of 1 to 5, and n an integer of the value of 0 to 4, providing that the sum of m and n is an integer of the value of not more than 5 to react with at least one fluorinating agent selected from the group consisting of alkali metal fluorides and alkaline earth metal fluorides in benzonitrile as a solvent at temperatures in the range of 190° to 400° C. under at least spontaneously generated pressure whereby at least one of said Y halogens is replaced by F.
Claim 3
Dependent Claim 15 words
A method according to claim 1 wherein said fluorinating agent is an alkali metal fluoride.
Claim 4
Dependent Claim 40 words
A method according to claim 1 wherein said chloro- or bromo-organic compound represented by the general formula I is used in an amount of about 5 to about 50 parts by weight based on 100 parts by weight of benzonitrile.
Claim 5
Dependent Claim 43 words
A method according to claim 1 wherein said fluorinating agent is used in an amount at least equivalent to the chlorine or bromine atom in said chloro- or bromo-organic compound represented by the general formula I to be substituted by a fluorine atom.
Claim 6
Dependent Claim 47 words
A method according to claim 1 wherein said alkali metal fluoride is used in an amount of 1 to 2 mols relative to the chlorine or bromine atom in said chloro- or bromo-organic compound represented by the general formula I to be substituted by a fluorine atom.
Claim 7
Dependent Claim 14 words
A method according to claim 2 wherein said alkali metal fluoride is potassium fluoride.
Claim 8
Dependent Claim 140 words
A method according to claim 1 wherein said compound represented by the general formula I is a compound represented by the general formula IV: ##STR17## wherein Y denotes Cl or Br, m denotes an integer of the value of 1 to 5, and n denotes an integer of the value of 0 to 4, providing that the sum of m and n is an integer of the value of not more than 5, and said compound represented by the general formula VIII is a compound represented by the general formula XI: ##STR18## wherein Y denotes Cl or Br, p denotes an integer of the value of 0 to 4, and q denotes an integer of the value of 1 to 5, providing that the sum of p and q is an integer of the value of not more than 5.
Claim 9
Dependent Claim 38 words
A method for the manufacture of pentafluorobenzonitrile according to claim 7 wherein said compound represented by the general formula XI is pentachlorobenzonitrile and the reaction is carried out at temperatures in the range of 270° to 400° C.
Claim 10
Dependent Claim 139 words
A method according to claim 1 wherein said compound represented by the general formula I is a compound represented by the general formula V: ##STR19## wherein Y denotes Cl or Br, m" denotes an integer of the value of 1to 4, and n" denotes an integer of the value of 0 to 3, providing that the sum of m" and n" is an integer of the value of not more than 4, and said compound represented by the general formula VIII is a compound represented by the general formula XII: ##STR20## wherein Y denotes Cl or Br, p" denotes an integer of the value of 0 to 3, and q" denotes an integer of the value of 1 to 4, providing that the sum of p" and q" is an integer of the value of not more than 4.
Claim 11
Dependent Claim 38 words
A method for the manufacture of tetrafluorophthalonitrile according to claim 9 wherein said compound represented by the general formula V is tetrachlorophthalonitrile and the reaction is carried out at temperatures in the range of 190° to 300° C.
Claim 12
Dependent Claim 38 words
A method for the manufacture of tetrafluoroisophthalonitrile according to claim 9 wherein said compound represented by the general formula V is tetrachloroisophthalonitrile and the reaction is carried out at temperatures in the range of 250° to 350° C.
Claim 13
Dependent Claim 38 words
A method for the manufacture of tetrafluoroterephthalonitrile according to claim 9 wherein said compound represented by the general formula V is tetrachloroterephthalonitrile and the reaction is carried out at temperatures in the range of 210° to 330° C.
Claim 14
Dependent Claim 102 words
A method according to claim 1 wherein said compound reperesented by the general formula I is a compound represented by the general formula VI: ##STR21## wherein Y denotes Cl or Br, m denotes an integer of the value of 1 to 5, and n denotes an integer of the value of 0 to 4, providing that the sum of m and n is an integer of the value of not more than 5, and said compound represented by the general formula VIII is a compound represented by the general formula XIII: ##STR22## wherein Y, p and q are as defined claim 1.
Claim 15
Dependent Claim 38 words
A method for the manufacture of pentafluoropyridine according to claim 33 wherein said compound represented by the general formula VI is pentachloropyridine and the reaction is carried out at temperatures in the range of 300° to 400° C.
Claim 16
Dependent Claim 116 words
A method according to claim 1 wherein said compound represented by the general formula V is a compound represented by the general formula VII: ##STR23## wherein Y denotes Cl or Br, m" denotes an integer of the value of 1 to 4, and n" denotes an integer of the value of 0 to 3, providing that the sum of m" and n" is an integer of the value of not more than 4, and said compound represented by the general formula VIII is a compound represented by the general formula XIV: ##STR24## wherein p" denotes an integer of the value of 0 to 4, and q" denotes an integer of the value of 1 to 5.
Claim 17
Dependent Claim 20 words
A method according to claim 1 wherein said reaction is carried out in the presence of a phase transfer catalyst.
Claim 18
Dependent Claim 31 words
A method according to claim 16 wherein said phase transfer catalyst is used in an amount of 0.01 to 0.25 mol based on 1 mol of said chloro- or bromo-organic compound.

References Cited (Backward Citations)

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GB1256082A Cited
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FR2096028A5 Cited
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EP0003344A1 Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-08-03 1991-02-02 1991-08-04 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-08-03 1995-02-02 1995-08-04 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-08-03 1999-02-02 1999-08-04 $7700.00 Window Closed / Lapsed

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