Claims
- 1. A primary aromatic diamine having the general formula: ##STR12## wherein X and Y are carbonyl or carbinol groups with the proviso that both X and Y can not be carbonyl groups; wherein the nitrogen may be independently attached to the benzene rings in the 2-, 3-, or 4-positions; and wherein isomerism is present when X, Y, or X and Y are said carbinol groups.
- 2. A primry aromatic diamine having the general formula: ##STR13## wherein X or Y may be a carbonyl or carbinol groups and X and Y may be the same or different; wherein the nitrogens may be independently attached to the benzene rings in the 2-, 3-, or 4-positions; and where isomerism is present when X, Y, or X and Y are said carbinol groups.
- 3. The diamine of claim 2, wherein said amine groups are both in the 3-position and X and Y are both carbonyl groups.
- 4. The diamine of claim 1, wherein said amine groups are both in the 3-positions and X and Y are both carbinol groups.
- 5. The diamine of claim 1, wherein said amine groups are both in the 4-position and said diamine is a mixture of amines containing carbonyl groups, carbinol groups, and carbonyl and carbinol groups.
- 6. The process for preparing the diamine of claim 4, which comprises the steps of:
- a. reacting a 3-nitrobenzoyl halide with diphenyl ether in the presence of aluminum chloride or other Lewis acid;
- b. catalytically hydrogenating the resultant 4,4'-bis(3-nitrobenzoyl)diphenyl ether;
- c. reducing the resultant 4,4'-bis(3-aminobenzoyl)diphenyl ether;
- and
- d. isolating the resultant 4,4'-bis[(3-aminophenyl)hydroxymethyl]diphenyl ether.
- 7. The process of claim 6, wherein said catalytic hydrogenation is carried out at 70.degree.-80.degree. C. using palladium on charcoal as the catalyst and wherein said reduction is carried out with sodium borohydride.
- 8. The process for preparing the diamine of claim 5, which comprises the steps of:
- a. reacting a 4-nitrobenzoyl halide with diphenyl ether in the presence of aluminum chloride or other Lewis acid;
- b. catalytically hydrogenating the resultant 4,4'-bis(4-nitrobenzoyl)diphenyl ether; and
- c. isolating the resultant mixture of 4,4'-bis(4-aminobenzoyl)diphenyl ether, 4-(4-aminobenzoyl)-4'-[4-aminophenyl)hydroxymethyl]diphenyl ether, 4-[4-aminophenyl)hydroxymethyl]-4'-(4-aminobenzoyl)diphenyl ether, and 4,4'-bis[(4-aminophenyl)hydroxymethyl]diphenyl ether.
- 9. The proces of claim 8, wherein said catalytic hydrogenation is carried out at 60.degree.-70.degree. C. using palladium on charcoal as the catalyst.
- 10. The process for preparing the diamine of claim 3, which comprises the steps of:
- a. reacting a 3-nitrobenzoyl halide with diphenyl sulfide in the presence of aluminum chloride or other Lewis acid;
- b. catalytically hydrogenating the resultant 4,4'-bis(3-nitrobenzoyl)diphenyl sulfide; and
- c. isolating the resultant 4,4'-bis(3-aminobenzoyl)diphenyl sulfide.
- 11. The process of claim 10, wherein said catalytic hydrogenation is carried out at 100.degree.-110.degree. C. using palladium on charcoal as the catalyst.
Parent Case Info
This application is a division of application Ser. No. 292,257, filed 8/12/81 now U.S. Pat. No. 4,405,770.
US Referenced Citations (12)
Non-Patent Literature Citations (1)
Entry |
W. Dilthey et al., "Die Wirkung der Nitrogruppe auf die Salzfarbe Positiver Ionen", Heteropolare Kohlenstoffverbindungen XIII, pp. 189-205, (Nov. 26, 1930). |
Divisions (1)
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Number |
Date |
Country |
Parent |
292257 |
Aug 1981 |
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