US4596680A
Expired / Lapsed
US
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Process for manufacturing aryl ethers having different substituents on the two aromatic rings
Assignee: Centre National de la Recherche Scientifique
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Filing: 1983-04-08
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Granted: 1986-06-24
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Expires: 2003-04-08
Abstract
Abstract A asymmetrical aryl ether of the formula X-Ar-O-Ar'-Y, wherein Ar and Ar' are each a divalent aromatic radical, X and Y are electron attracting atoms or groups which differ from each other or have different positions on the corresponding aromatic radicals, is produced by heating together, in the presence of a basic catalyst, equimolecular amounts of two aryl carbonates of the formulas: X-Ar-O-CO-O-Ar-X, and Y-Ar'-O-CO-O-Ar'-Y
Inventors
- 👤 Philippe Jost
- 👤 Pierre Le Perchec
- 👤 Bernard Sillion
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 05:32
CPC Classifications
C; C07; C07C; C07C201/00; C07C201/06; C07C201/12; C07C213/00; C07C213/02; C07C231/00; C07C231/12; C07C253/00; C07C253/30; C07C315/00; C07C315/04
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
166 words
A process for the manufacture of an asymmetrical aryl ether of the general formula: X--Ar--O--Ar'--Y wherein Ar and Ar' are each a divalent aromatic radical having one or more rings, X and Y, as incorporated in said ether, are each an atom or group having electron-attracting properties, insensitive to the action of bases, and differing from each other by their nature and/or by their respective positions in radicals Ar or Ar', at least one of the X and Y substituents being, on the Ar or Ar' radical, in ortho, pera or peri position with respect to the oxygen atom bond and wherein neither X nor Y is chlorine, said process being characterized by heating sufficiently together, in the presence of a basic catalyst, substantially equal amounts of two aryl carbonates complying with the general formulas: X--Ar--O--CO--O--Ar--X, and Y--Ar'--O--CO--O--Ar'--Y wherein Ar, Ar', X and Y are defined as above to obtain a higher than statistical proportion of said assymetrical ether and separating the formed asymmetrical aryl ether.
Claim 2
Dependent Claim
166 words
A process for the manufacture of an asymmetrical aryl ether of the general formula: X--Ar--O--Ar'--Y wherein Ar and Ar' are each a divalent aromatic radical having one or more rings, X and Y, as incorporated in said ether, are each an atom or group having electron-attracting properties, insensitive to the action of bases, and differing from each other by their nature and/or by their respective positions in radicals Ar or Ar', at least one of the X and Y substituents being, on the Ar or Ar' radical, in ortho, pera or peri position with respect to the oxygen atom bond and wherein neither X nor Y is chlorine, said process being characterized by heating sufficiently together, in the presence of a basic catalyst, substantially equal amounts of two aryl carbonates complying with the general formulas: X--Ar--O--CO--O--Ar--X, and Y--Ar'--O--CO--O--Ar'--Y wherein Ar, Ar', X and Y are defined as above to obtain a higher than statistical proportion of said assymetrical ether and separating the formed asymmetrical aryl ether.
Claim 3
Dependent Claim
44 words
A process according to claim 1, wherein the Ar and Ar' radicals are phenylene radicals and at least one of the X and Y substituents on the Ar or Ar' radical is in ortho or para position with respect to the oxygen atom bond.
Claim 4
Dependent Claim
61 words
A process according to claim 1, characterized by the selection of X and Y from the groups consisting of --NO 2 , --CN, --COOAr", --SO 2 Ar", wherein Ar" is a monovalent aromatic radical, and --CONR 1 R 2 , wherein R 1 and R 2 are each a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
Claim 5
Dependent Claim
66 words
A process according to claim 1, characterized in that X is a --NO 2 group and Y is selected from the groups consisting of --NO 2 , --CN, --COOAr", --SO 2 Ar", wherein Ar" is a monovalent aromatic radical, and --CONR 1 R 2 wherein R 1 and R 2 are each a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms.
Claim 6
Dependent Claim
26 words
A process according to claim 1, characterized in that the two starting carbonates are heated, in molten state, at a temperature from 190° to 280° C.
Claim 7
Dependent Claim
25 words
A process according to claim 1, characterized in that the two starting carbonates are heated, as solution, at a temperature from 190° to 280° C.
Claim 8
Dependent Claim
25 words
A process according to claims 1 to 6, characterized in that the basic catalyst is selected from the alkali metal carbonates, phenates, acetates and alcoholates.
Claim 9
Dependent Claim
30 words
A process according to one of claim 1, characterized in that the catalyst is used in an amount of 0.1 to 5 moles per 100 moles of the starting carbonate.
Claim 10
Dependent Claim
19 words
A process according to claim 1, wherein the aryl ether is obtained with a yield of at least 75%.
Claim 11
Dependent Claim
25 words
A process according to claim 1, characterized in that the two aryl carbonates are different and selected from: bis-(4-nitrophenyl)carbonate, bis-(3-nitrophenyl)carbonate, bis-(4-cyanophenyl)carbonate, bis-(2-phenoxy-carboxyphenyl)carbonate, bis-(4-phenylsulfonylphenyl)carbonate, and bis-(2-N,N-dimethylcarbamoyl-phenyl)carbonate.
Claim 12
Dependent Claim
37 words
A process according to claim 10, characterized in that one of the two aryl carbonates is bis-(4-nitrophenyl)carbonate, and the other is selected from: bis-(3-nitrophenyl)carbonate, bis-(4-cyanophenyl)carbonate, bis-(2-phenoxy-carboxyphenyl)carbonate, and bis-(4-phenylsulfonylphenyl)carbonate and in that the basic catalyst is potassium carbonate.
Claim 13
Dependent Claim
51 words
A process according to claim 1, characterized by the preparation of a dissymmetrical aryl ether of the formula X--Ar--O--Ar'--Y wherein at least one of the X and Y substituents is a --NO 2 group and the subsequent hydrogenation of said aryl ether, converting the --NO 2 groups to primary amine groups.
References Cited (Backward Citations)
DE1290148B
Cited
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