Method for ether formation
AssigneeOccidental Chemical Corporation
InventorsRobert Buchanan, Jeffrey Stults, Henry C. Lin
Life of this patent
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Abstract
A process for the preparation of 4,4'-dinitro-2,2'-di(trifluoromethyl)diphenyl ether according to the equation ##STR1## where X is F, Cl, Br or I, where the inorganic base is selected from the group consisting of alkali metal hydroxides, alkali metal carbonates, and alkali metal bicarbonates, in the presence of a catalytic quantity of a benzoate catalyst. 2,8-Dinitro-6,6,12,12,-tetrafluoro-6H,12H-dibenzo[b,f][1,5]dioxocin, the corresponding diamine and polyimides formed from the diamine are also disclosed.
Claims28
A process for the preparation of 4,4'-dinitro-2,2'-bis(trifluoromethyl)diphenyl ether comprising reacting a compound of the formula ##STR9## where X is F, Cl, Br, or I with approximately one equivalent of an inorganic base selected from the group consisting of alkali metal hydroxides, alkali metal carbonates, and alkali metal bicarbonates, in the presence of at least about 0.1 mole % of a benzoate catalyst selected from the group consisting of 4-chlorobenzoic acid, 3-nitrobenzoic acid, 4-nitrobenzoic acid, 3,5-dinitrobenzoic acid, and 3,5-dichlorobenzoic acid, and a small amount of water.
A process for the preparation of 4,4'-dinitro-2,2'-bis(trifluoromethyl)diphenyl ether comprising reacting in a non-polar solvent in the presence of a phase transfer catalyst a compound of the formula ##STR10## where X is F, Cl, Br, or I with approximately one equivalent of an inorganic base selected from the group consisting of alkali metal hydroxides, alkali metal carbonates, and alkali metal bicarbonates, in the presence of at least about 0.1 mole % of a benzoate catalyst and a small amount of water.
A process for the preparation of 4,4'-dinitro-2,2'-bis(trifluoromethyl)diphenyl ether comprising reacting in a polar aprotic solvent a compound of the formula ##STR11## where X is F, Cl, Br, or I, with approximately one equivalent of an inorganic base selected from the group consisting of sodium carbonate and potassium carbonate in the presence of at least about 0.1 mole % of a benzoate catalyst selected from the group consisting of 4-chlorobenzoic acid, 3-nitrobenzoic acid, 4-nitrobenzoic acid, 3,5-dinitrobenzoic acid, and 3,5-dichlorobenzoic acid, and a small amount of water.
A process for the preparation of 4,4'-dinitro-2,2'-bis(trifluoromethyl)diphenyl ether comprising reacting in the absence of a solvent a compound of the formula ##STR12## where X is F, Cl, Br, or I with approximately one equivalent of an inorganic base selected from the group consisting of alkali metal hydroxides, alkali metal carbonates, and alkali metal bicarbonates, in the presence of at least about 0.1 mole % of a benzoate catalyst and a small amount of water.
A method of making 4,4'-dinitro-2,2'-bis(trifluoromethyl)diphenyl ether comprising
- (A) preparing a mixture of
- (1) a compound having the formula ##STR13## where X is F or Cl;
- (2) approximately one equivalent of sodium carbonate;
- (3) a small amount of water;
- and
- (4) at least about 0.1 mole % of a benzoate catalyst selected from the group consisting of 4-chlorobenzoic acid, 3-nitrobenzoic acid, 4-nitrobenzoic acid, 3,5-dinitrobenzoic acid, and 3,5-dichlorobenzoic acid;
- and
- (B) heating said mixture to about 140.degree. to about 220.degree. C.
A method of preferentially reacting 4-nitro-2-(trifluoromethyl)-chlorobenzene in a mixture with 2-nitro-6-(trifluoromethyl)-chlorobenzene to form 4,4'-dinitro-2,2'-bis(trifluoromethyl)diphenyl ether comprising
- (a) adding to said mixture
- (1) ##STR14## where X is F or Cl;
- approximately one equivalent of a base selected from the group consisting of sodium hydroxide, sodium carbonate, and sodium bicarbonate;
- and
- (2) at least about 0.1 mole % of a benzoate catalyst selected from the group consisting of 4-chlorobenzoic acid, 3-nitrobenzoic acid, 4-nitrobenzoic acid, 3,5-dinitrobenzoic acid, and 3,5-dichlorobenzoic acid;
- and
- (b) heating said mixture to about 140.degree. to about 220.degree. C.
Dependencies are inferred from the claim text.