Patent US4045496A successfully refreshed from Google Patents.
US4045496A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the hydroxylation of phenols and phenol ethers in the nucleus
Assignee: Bayer AG
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Filing: 1975-02-28
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Granted: 1977-08-30
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Expires: 1995-02-28
Abstract
Abstract A process for the hydroxylation of phenols and phenol ethers in the nucleus with hydrogen peroxide wherein a phenol or a phenol ether is reacted at the start of the reaction with substantially anhydrous hydrogen peroxide and wherein the reaction is carried out in the presence of a strong acid.
Inventors
- 👤 Hermann Seifert
- 👤 Helmut Waldmann
- 👤 Wulf Schwerdtel
- 👤 Wolfgang Swodenk
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 05:01
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/60; C07C41/00; C07C41/01; C07C41/18; C07C41/26; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/582
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
140 words
In a catalytic process for the hydroxylation of the nucleus of a phenol or phenol ether wherein a phenol or phenol ether is contacted with hydrogen peroxide at a temperature of 20°-150° C and at a pressure of 0.1 to 500 Torr employing 3 to 20 moles of said phenol or phenol ether per mole of hydrogen peroxide and the resulting hydroxylated phenol or phenol ether is recovered, the improvement which comprises employing a substantially anhydrous hydrogen peroxide obtained by distilling off said hydrogen peroxide together with the phenol or phenol ether to be hydroxylated from a nonaqueous solution whose solvent boils at a temperature higher than said phenol or phenol ether to be hydroxylated and affecting the hydroxylation in the presence of a strong acid either before or after condensing the vapor mixture which forms during the said distillation.
Claim 2
Dependent Claim
140 words
In a catalytic process for the hydroxylation of the nucleus of a phenol or phenol ether wherein a phenol or phenol ether is contacted with hydrogen peroxide at a temperature of 20°-150° C and at a pressure of 0.1 to 500 Torr employing 3 to 20 moles of said phenol or phenol ether per mole of hydrogen peroxide and the resulting hydroxylated phenol or phenol ether is recovered, the improvement which comprises employing a substantially anhydrous hydrogen peroxide obtained by distilling off said hydrogen peroxide together with the phenol or phenol ether to be hydroxylated from a nonaqueous solution whose solvent boils at a temperature higher than said phenol or phenol ether to be hydroxylated and affecting the hydroxylation in the presence of a strong acid either before or after condensing the vapor mixture which forms during the said distillation.
Claim 3
Dependent Claim
20 words
A process as claimed in claim 1, wherein at least one stabiliser is used in conjunction with the hydrogen peroxide.
Claim 4
Dependent Claim
31 words
A process as claimed in claim 1, wherein an ester or N-alkyl amide of phosphoric acid, phosphonic acid or phosphinic acid is used as the higher boiling solvent for hydrogen peroxide.
Claim 5
Dependent Claim
26 words
A process as claimed in claim 1, wherein from 10 to 15 mols of the phenol or phenol ether are used per mol of hydrogen peroxide.
Claim 6
Dependent Claim
41 words
A process as claimed in claim 1, wherein the strong acid is sulphuric acid, sulphuric acid in admixture with phosphoric acid, a fluorine-substituted polymeric sulphonic acid, fluorosulphonic acid, a perfluorinated alkyl sulphonic acids or fluorosulphonic acid in admixture with antimony pentafluoride.
Claim 7
Dependent Claim
27 words
A process as claimed in claim 1, wherein from 0.01 to 2.0 mols of the strong acid is present in reaction mixture per mol of hydrogen peroxide.
Claim 8
Dependent Claim
27 words
A process as claimed in claim 6, wherein from 0.1 to 1.5 mols of the strong acid is present in reaction mixture per mol of hydrogen peroxide.
Claim 9
Dependent Claim
33 words
A process as claimed in claim 1, wherein the reaction is carried out in the presence of a stabiliser in a quantity of from 0.001 to 1 mol per mol of hydrogen peroxide.
Claim 10
Dependent Claim
28 words
A process as claimed in claim 8, wherein the reaction is carried out in the presence of 0.1 to 0.5 mol of stabiliser per mol of hydrogen peroxide.
Claim 11
Dependent Claim
25 words
A process as claimed in claim 8 wherein the stabiliser is an ester or an N-alkyl amide of phosphoric acid, phosphoric acid or phosphinic acid.
Claim 12
Dependent Claim
26 words
A process as claimed in claim 1, wherein the reaction is carried out at a temperature in the range of from 30° C to 100° C.
Claim 13
Dependent Claim
20 words
A process as claimed in claim 1, wherein the reaction is carried out continuously with recycling of the unreacted reactants.
Claim 14
Dependent Claim
40 words
A process according to claim 1, wherein the solvent of said hydrogen peroxide is selected from the group consisting of tri-n-butyl phosphate, tri-n-octyl phosphate, tri-[(2-ethyl)-hexyl]-phosphate, hexamethyl phosphoric acid triamide, β-carbomethoxy ethanophosphonic acid methyl ester and β-carbohydroxy ethanophosphonic acid methyl ester.
Claim 15
Dependent Claim
20 words
A process according to claim 13 wherein a 5-30% solution of hydrogen peroxide in an anhydrous organic solvent is used.
Claim 16
Dependent Claim
20 words
A process according to claim 14 wherein a 10-25% solution of hydrogen peroxide in an anhydrous organic solvent is used.
Claim 17
Dependent Claim
67 words
A process according to claim 1 wherein vapors of distilled off hydrogen peroxide are introduced into an anhydrous solvent thereof thereby forming an anhydrous hydrogen peroxide solution and to said anhydrous hydrogen peroxide solution there is added said phenol or phenol ether and said phenol or phenol ether is reacted therein with said hydrogen peroxide in the presence of said strong acid at said temperature and pressure.
Claim 18
Dependent Claim
23 words
A process according to claim 16 wherein vapors of said phenol or phenol ether are added to said hydrogen peroxide solution so formed.
Claim 19
Dependent Claim
22 words
A process according to claim 16 wherein said solvent into which said hydrogen peroxide is introduced is a phenol or phenol ether.
Claim 20
Dependent Claim
49 words
A process according to claim 1 wherein hydrogen peroxide is distilled over from a solution together with a phenol or phenol ether and is reacted with said phenol or phenol ether in the presence of a strong acid while said phenol or phenol ether is in the liquid phase.
Claim 21
Dependent Claim
46 words
A process according to claim 1 wherein said hydrogen peroxide is distilled over together with phenol or phenol ether and is reacted with said phenol or phenol ether in the presence of said strong acid while said phenol or phenol ether is in the vapor phase.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-08-29 | 1981-02-28 | 1981-08-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-08-29 | 1985-02-28 | 1985-08-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-08-29 | 1989-02-28 | 1989-08-30 | $7700.00 | Window Closed / Lapsed |