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US4922019A
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Derivatives of 2,2-bis-(3-aminophenyl)hexafluoropropane and process for the preparation of 2,2-bis-(3,4-diaminophenyl)hexafluoropropane
Assignee: Hoechst AG
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Filing: 1988-06-29
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Granted: 1990-05-01
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Expires: 2008-06-29
Abstract
Abstract The invention relates to compounds of the formula ##STR1## wherein R 1 is hydrogen or an acyl group in which a non-aromatic hydrocarbon group of 1 to 6 carbon atoms is attached to the CO-group and R 2 is H or NO 2 , if R 1 is an acyl group, or is NO 2 , if R 1 is hydrogen. The invention further relates to a process for the production of 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane of the formula ##STR2## which comprises (a) acylating 2,2-bis-(3-aminophenyl)-hexafluoropropane, under conditions conventional for acylations, to yield a 2,2-bis-(3-acylamidophenyl)-hexafluoropropane, the acyl group of which is free from aromatic groups, (b) nitrating the 2,2-bis-(3-acylamidophenly)-hexafluoropropane, under conditions conventional for nitrations, to yield 2,2-bis-(3-acylamido-4-nitrophenyl)-hexafluoropropane, (c) deacylating the 2,2-bis-(3-acylamido-4-nitrophenyl)-hexafluoropropane, under conditions conventional for deacylations, to yield 2,2-bis-(3-amino-4-nitrophenyl)-hexafluoropropane, (d) reducing this compound, under conditions conventional for the reduction of nitro compounds, to yield 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane, and (e) isolating this compound or subjecting it to a purificaton by converting it into a solution of one of its salts, adsorbing contaminations at an adsorption agent and recipitating the 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane by addition of a base.
Inventors
- 👤 Jurgen Lau
- 👤 Gunter Siegemund
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 14:44
CPC Classifications
C; C07; C07C; C07C211/00; C07C211/43; C07C211/44; C07C211/52
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
57 words
A compound of the formula ##STR5## wherein R 1 is hydrogen or an acyl group in which a nonaromatic hydrocarbon group of 1 to 6 carbon atoms is attached to the CO-group and R 2 is H or NO 2 if R 1 is an acyl group, and is NO 2 , if R 1 is hydrogen.
Claim 2
Dependent Claim
57 words
A compound of the formula ##STR5## wherein R 1 is hydrogen or an acyl group in which a nonaromatic hydrocarbon group of 1 to 6 carbon atoms is attached to the CO-group and R 2 is H or NO 2 if R 1 is an acyl group, and is NO 2 , if R 1 is hydrogen.
Claim 3
Dependent Claim
27 words
The compound as claimed in claim 1, wherein R 1 as an acyl group is an acetyl group and R 2 is hydrogen or NO 2 .
Claim 4
Dependent Claim
19 words
The compound as claimed in claim 1, wherein R 1 is hydrogen and R 2 is NO 2 .
Claim 5
Dependent Claim
111 words
A process for the production of 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane of the formula ##STR6## which comprises (a) acylating 2,2-bis-(3-aminophenyl)-hexafluoropropane, under conditions conventional for acylations, to yield a 2,2-bis-(3-acylamidophenyl)-hexafluoropropane, the acyl group of which is free from aromatic groups, (b) nitrating the 2,2-bis-(3-acylamidophenyl)-hexafluoropropane, under conditions conventional for nitrations, to yield 2,2-bis-(3-acylamido-4-nitrophenyl)-hexafluoropropane, (c) deacylating the 2,2-bis-(3-acylamido-4-nitrophenyl)-hexafluoropropane, under conditions conventional for deacylations, to yield 2,2-bis-(3-amino-4-nitrophenyl)-hexafluoropropane, (d) reducing this compound, under conditions conventional for the reduction of nitro compounds, to yield 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane, and (e) isolating 2,2-bis-(3,4,-diaminophenyl)-hexafluoropropane or subjecting it to a purification by converting it into a solution of one of its salts, adsorbing contaminations at an adsorption agent and precipitating the 2,2-bis-(3,4-diaminophenyl)hexafluoropropane by addition of a base.
Claim 6
Dependent Claim
111 words
A process for the production of 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane of the formula ##STR6## which comprises (a) acylating 2,2-bis-(3-aminophenyl)-hexafluoropropane, under conditions conventional for acylations, to yield a 2,2-bis-(3-acylamidophenyl)-hexafluoropropane, the acyl group of which is free from aromatic groups, (b) nitrating the 2,2-bis-(3-acylamidophenyl)-hexafluoropropane, under conditions conventional for nitrations, to yield 2,2-bis-(3-acylamido-4-nitrophenyl)-hexafluoropropane, (c) deacylating the 2,2-bis-(3-acylamido-4-nitrophenyl)-hexafluoropropane, under conditions conventional for deacylations, to yield 2,2-bis-(3-amino-4-nitrophenyl)-hexafluoropropane, (d) reducing this compound, under conditions conventional for the reduction of nitro compounds, to yield 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane, and (e) isolating 2,2-bis-(3,4,-diaminophenyl)-hexafluoropropane or subjecting it to a purification by converting it into a solution of one of its salts, adsorbing contaminations at an adsorption agent and precipitating the 2,2-bis-(3,4-diaminophenyl)hexafluoropropane by addition of a base.
Claim 7
Dependent Claim
21 words
The process as claimed in claim 4, wherein the acylation is carried out with an acid halide or an acid anhydride.
Claim 8
Dependent Claim
26 words
The process as claimed in claim 5, wherein in the acylating compound a hydrocarbon group of 1 to 6 carbon atoms is attached to the CO-group.
Claim 9
Dependent Claim
13 words
The process as claimed in claim 6, wherein the acylation is an acetylation.
Claim 10
Dependent Claim
15 words
The process as claimed in claim 7, wherein the acetylation is carried out with acetanhydride.
Claim 11
Dependent Claim
23 words
The process as claimed in claim 4, wherein the reduction in step (d) is carried out catalytically with hydrogen at a transition metal.
Claim 12
Dependent Claim
225 words
The process as claimed in claim 4, wherein at least one condition selected from the group consisting of (a) the acylation is carried out at a temperature in the range of from 0° to 50° C., (b 1 ) the nitration is carried out with a nitric acid of 85 to 95 % strength by weight, (b 2 ) the acylated compound obtained in step (a) is introduced into the nitric acid-water-mixture, (c 1 ) the deacylation is carried out in a solution of the acylated compound in water or a solvent miscible with water, or a combination thereof, which solution contains from 5 to 50 % by weight of a base, (c 2 ) the deacylation is effected at a temperature in the range of from 0° to 100° C., (d) the reduction is carried out catalytically with hydrogen and a transition metal of group VIII of the Periodic System, (e 1 ) the 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane is converted into a solution of one of its salts while excluding oxygen, (e 2 ) the said 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane is converted into a hydrohalide, (e 3 ) the adsorption agent is activated charcoal, (e 4 ) the 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane is precipitated by an aqueous solution of ammonia and (e 5 ) the precipitation of the 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane by addition of the base is effected under exclusion of oxygen is applied therein.
Claim 13
Dependent Claim
90 words
The process as claimed in claim 10, wherein at least one condition selected from the group consisting of (a) the acylation is carried out at a temperature in the range of from 5° to 20° C., (b 2 ) the acylated compound is introduced into the nitric acid-water-mixture at a temperature in the range of from 0° to 40° C., (c 1 ) the deacylation is effected in a solution of an alcohol, and (e 2 ) the 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane is converted into a solution of the hydrochloride is applied therein.
Claim 14
Dependent Claim
34 words
The process as claimed in claim 4, wherein the conversion of the 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane into one of its salts and the precipitation of the 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane with a base is carried out under exclusion of oxygen.
Claim 15
Dependent Claim
139 words
A process for the production of 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane of the formula ##STR7## which comprises (a) acylating 2,2-bis-(3-aminophenyl)-hexafluoropropane with an acid halide or an acid anhydride at a temperature in the range of from 0° to 50° C. to yield a 2,2-bis-(3-acyl- amidophenyl)-hexafluoropropane, the acyl group of which is free from aromatic groups, (b) nitrating the 2,2-bis-(3-acylamidophenyl)-hexafluoropropane with a nitric acid of 85 to 95% strength by weight to yield 2, 2-bis-(3-acylamido-4-nitrophenyl)-hexafluoropropane, (c) deacylating the 2,2-bis-(3-acylamido-4-nitrophenyl)-hexafluoropropane at a temperature in the range of from 0° to 100° C. in a solution of the acylated compound in water, a solvent miscible with water, or a combination thereof, which solution comprises from 5 to 50% by weight of a base, to yield 2,2-bis-(3-amino-4-nitrophenyl)-hexafluoropropane, (d) reducing 2,2-bis(3-amino-4-nitrophenyl)-hexfluoropropane catalytically with hydrogen and a transition metal of group vIII of the periodic system to yield 2,2-(bis-(3,4-diaminophenyl)-hexafluoropropane.
Claim 16
Dependent Claim
139 words
A process for the production of 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane of the formula ##STR7## which comprises (a) acylating 2,2-bis-(3-aminophenyl)-hexafluoropropane with an acid halide or an acid anhydride at a temperature in the range of from 0° to 50° C. to yield a 2,2-bis-(3-acyl- amidophenyl)-hexafluoropropane, the acyl group of which is free from aromatic groups, (b) nitrating the 2,2-bis-(3-acylamidophenyl)-hexafluoropropane with a nitric acid of 85 to 95% strength by weight to yield 2, 2-bis-(3-acylamido-4-nitrophenyl)-hexafluoropropane, (c) deacylating the 2,2-bis-(3-acylamido-4-nitrophenyl)-hexafluoropropane at a temperature in the range of from 0° to 100° C. in a solution of the acylated compound in water, a solvent miscible with water, or a combination thereof, which solution comprises from 5 to 50% by weight of a base, to yield 2,2-bis-(3-amino-4-nitrophenyl)-hexafluoropropane, (d) reducing 2,2-bis(3-amino-4-nitrophenyl)-hexfluoropropane catalytically with hydrogen and a transition metal of group vIII of the periodic system to yield 2,2-(bis-(3,4-diaminophenyl)-hexafluoropropane.
Claim 17
Dependent Claim
176 words
A process for the production of 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane of the formula ##STR8## which comprises (a) acylating 2,2-bis-(3-aminophenyl)-hexafluoropropane with an acid halide or an acid anhydride at a temperature in the range of from 0° to 50° C. to yield a 2,2-bis-(3-acyl- amidophenyl)-hexafluoropropane, the acyl group of which is free from aromatic groups, (b) nitrating the 2,2-bis-(3-acylamidophenyl)-hexafluoropropane with an effective amount of nitric acid of 85 to 95% strength by weight to yield 2,2-bis-(3-acylamido-4-nitrophenyl)hexafluoropropane, (c) deacylating the 2,2-bis-(3-acylamido-4-nitrophenyl)-hexafluoropropane at a temperature in the range of from 0° to 100° C. in a solution of the acylated compound in water, a solvent miscible with water, or a combination thereof, which solution comprises from 5 to 50% by weight of a base, to yield 2,2-bis-(3-amino-4-nitrophenyl)-hexafluoropropane, (d) reducing this compound catalytically with hydrogen and a transition metal of group VIII of the periodic system to yield 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane, and (e) subjecting this compound to purification by converting it into a solution of one of its salts, adsorbing the contaminants on an adsorption agent and precipitating the 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane by addition of a base.
Claim 18
Dependent Claim
176 words
A process for the production of 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane of the formula ##STR8## which comprises (a) acylating 2,2-bis-(3-aminophenyl)-hexafluoropropane with an acid halide or an acid anhydride at a temperature in the range of from 0° to 50° C. to yield a 2,2-bis-(3-acyl- amidophenyl)-hexafluoropropane, the acyl group of which is free from aromatic groups, (b) nitrating the 2,2-bis-(3-acylamidophenyl)-hexafluoropropane with an effective amount of nitric acid of 85 to 95% strength by weight to yield 2,2-bis-(3-acylamido-4-nitrophenyl)hexafluoropropane, (c) deacylating the 2,2-bis-(3-acylamido-4-nitrophenyl)-hexafluoropropane at a temperature in the range of from 0° to 100° C. in a solution of the acylated compound in water, a solvent miscible with water, or a combination thereof, which solution comprises from 5 to 50% by weight of a base, to yield 2,2-bis-(3-amino-4-nitrophenyl)-hexafluoropropane, (d) reducing this compound catalytically with hydrogen and a transition metal of group VIII of the periodic system to yield 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane, and (e) subjecting this compound to purification by converting it into a solution of one of its salts, adsorbing the contaminants on an adsorption agent and precipitating the 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane by addition of a base.
Claim 19
Dependent Claim
46 words
The process as claimed in claim 14, wherein step (e) further comprises: (e 1 ) converting the 2,2-bis-(3,4-diammophenyl)-hexafluoropropane in a solution of a hydrohalide, (e 2 ) absorbing the contaminants on activated charcoal, and (e 3 ) precipitating the 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane with an aqueous solution of ammonia.
Claim 20
Dependent Claim
37 words
The process of claim 14, wherein, in said step (e), the conversion of the 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane into one of its salts and the precipitation of the 2,2-bis-(3,4-diaminophenyl)-hexafluoropropane with a base is carried out under the exclusion of oxygen.
References Cited (Backward Citations)
US3310573A
Cited
US4370501A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-04-30 | 1993-10-30 | 1994-05-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-04-30 | 1997-10-30 | 1998-05-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-04-30 | 2001-10-30 | 2002-05-01 | $7700.00 | Window Closed / Lapsed |