Patent US3929907A successfully refreshed from Google Patents.
US3929907A
Expired / Lapsed
US
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Halogenation of phenolic compounds
Assignee: Evonik Operations GmbH
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Filing: 1973-06-01
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Granted: 1975-12-30
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Expires: 1993-06-01
Abstract
Abstract Aromatic and heterocyclic compounds are halogenated by a combination of chlorine, bromine or iodine and hydrogen peroxide, preferably in a two-phase system containing water and an organic liquid.
Inventors
- 👤 Karl Heinz Janzon
- 👤 Wolfgang Weigert
- 👤 Hilmar Hein
- 👤 Helmut Mechler
- 👤 Eugen Meyer-Simon
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 04:24
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/61; C07C45/63; C07B; C07B39/00; C07C17/00; C07C17/093; C07C17/10; C07C17/12; C07C37/00; C07C37/62; C07C47/00; C07C47/52; C07C47/56; C07C47/565; C07C51/00; C07C51/347; C07C51/363
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
94 words
IN A PROCESS OF HALOGENATING A PHENOL SELECTED FROM THE GROUP CONSISTING OF (1) A PHENOL HAVING 1 TO 2 PHENOLIC HYDROXYL GROUPS AS THE SOLE SUBSTITUENTS, (2) BENZENE HAVING ONE HYDROXYL SUBSTITUENT AND ONE ALDEHYDO. CARBOXYLIC ACID OR SULFONIC ACID SUBSTITUENT AS THE SOLE SUBSTITUENTS, (3) P-AMINOPHENOL, (4) P-NITROPHENOL, (5) O-NITROPHENOL, (6) P-FLUOROPHENOL, (7) P:CHLOROPHENOL AND (8) O-BROMOPHENOL WITH CHLORINE OR BROMINE IN THE LIQUID PHASE THE IMPROVEMENT COMPRISING CARRYING OUT SAID HALOGENATION IN THE PRESENCE OF AQUEOUS HYDROGEN PEROXIDE AT A TEMPERATURE OF 0* TO 100*C. AND RECOVERING THE HALOGENATED PHENOL FORMED.
Claim 2
Dependent Claim
94 words
IN A PROCESS OF HALOGENATING A PHENOL SELECTED FROM THE GROUP CONSISTING OF (1) A PHENOL HAVING 1 TO 2 PHENOLIC HYDROXYL GROUPS AS THE SOLE SUBSTITUENTS, (2) BENZENE HAVING ONE HYDROXYL SUBSTITUENT AND ONE ALDEHYDO. CARBOXYLIC ACID OR SULFONIC ACID SUBSTITUENT AS THE SOLE SUBSTITUENTS, (3) P-AMINOPHENOL, (4) P-NITROPHENOL, (5) O-NITROPHENOL, (6) P-FLUOROPHENOL, (7) P:CHLOROPHENOL AND (8) O-BROMOPHENOL WITH CHLORINE OR BROMINE IN THE LIQUID PHASE THE IMPROVEMENT COMPRISING CARRYING OUT SAID HALOGENATION IN THE PRESENCE OF AQUEOUS HYDROGEN PEROXIDE AT A TEMPERATURE OF 0* TO 100*C. AND RECOVERING THE HALOGENATED PHENOL FORMED.
Claim 3
Dependent Claim
20 words
A process according to claim 1, wherein the compound has 1 to 2 phenolic hydroxyl groups as the sole substituents.
Claim 4
Dependent Claim
5 words
a water immiscible organic liquid.
Claim 5
Dependent Claim
5 words
a water immiscible organic liquid.
Claim 6
Dependent Claim
5 words
a water immiscible organic liquid.
Claim 7
Dependent Claim
5 words
a water immiscible organic liquid.
Claim 8
Dependent Claim
21 words
A process according to claim 1 wherein the phenol is a phenol having 2 phenolic hydroxyl groups as the sole substituents.
Claim 9
Dependent Claim
13 words
A process according to claim 3 wherein the phenol is an alkylidene diphenol.
Claim 10
Dependent Claim
13 words
A process according to claim 2, wherein the compounds is 4, 41-isopropylidene diphenol.
Claim 11
Dependent Claim
11 words
A process according to claim 5, wherein the halogen is bromine.
Claim 12
Dependent Claim
43 words
A process according to claim 6, wherein the bromine is used in an amount of 0.50 to 0.55 moles and the hydrogen peroxide in an amount of 0.40 to 0.45 moles per mole of the diphenol and the product is 4,41-isopropylidene bis (2,6-dibromo-phenol).
Claim 13
Dependent Claim
24 words
A process according to claim 1, wherein the phenol is benzene having one hydroxyl substituent and one aldehydo, carboxylic acid or sulfonic acid substituent.
Claim 14
Dependent Claim
11 words
A process according to claim 8, wherein the halogen is bromine.
Claim 15
Dependent Claim
18 words
A process according to claim 1, wherein the process is carried out in a two phase system of:
Claim 16
Dependent Claim
11 words
A process according to claim 1 wherein the halogen is bromine.
Claim 17
Dependent Claim
54 words
A process according to claim 1 wherein the phenol is selected from the group consisting of phenol per se, hydroquinone, salicylaldehyde, salicylic acid, p-aminophenol, m-cresol, o-cresol, p-cresol, 1,2,4-xylenol, resorcinol, p-t-butylphenol, p-dodecylphenol, m-octylphenol- o-butylphenol, p-octadecylphenol, alpha naphthol, beta naphthol, p-phenylphenol, p-nitrophenol, o-nitrophenol, anthrahydroquinone, p-fluorophenol, p-chlorophenol, o-bromophenol, 4,4''-isopropylidene diphenol, 2,2''-isopropylidene diphenol, 4,4''-methylenebisphenol, 4,4''-butylidene diphenol, and 4,4''-dihydroxydiphenyl.
Claim 18
Dependent Claim
30 words
A process according to claim 1, wherein the proportions of halogen to hydrogen peroxide range from an excess of 10% of halogen to an excess of 50% of hydrogen peroxide.
Claim 19
Dependent Claim
11 words
A process according to claim 5 wherein the halogen is chlorine.
Claim 20
Dependent Claim
11 words
A process according to claim 8 wherein the halogen is chlorine.
Claim 21
Dependent Claim
11 words
A process according to claim 1 wherein the halogen is chlorine.
Claim 22
Dependent Claim
11 words
A process according to claim 12 wherein the halogen is bromine.
Claim 23
Dependent Claim
11 words
A process according to claim 13 wherein the halogen is bromine.
Claim 24
Dependent Claim
11 words
A process according to claim 10 wherein the halogen is bromine.
Claim 25
Dependent Claim
12 words
A process according to claim 19 wherein the phenol is 4,4''-isopropylidene diphenol.
Claim 26
Dependent Claim
18 words
A process according to claim 12 wherein the process is carried out in a two phase system of:
Claim 27
Dependent Claim
25 words
A process according to claim 10 wherein there is employed 1 to 5 parts by volume or organic solvent per part by volume of water.
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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) | 1978-12-29 | 1979-06-30 | 1979-12-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-12-29 | 1983-06-30 | 1983-12-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-12-29 | 1987-06-30 | 1987-12-30 | $7700.00 | Window Closed / Lapsed |