US4053523A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the hydroxylation of phenol
Assignee: Bayer AG
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Filing: 1975-02-28
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Granted: 1977-10-11
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Expires: 1995-02-28
Abstract
Abstract A process for the production of pyrocatechol and hydroquinone by the hydroxylation of phenol in the nucleus with hydrogen peroxide, wherein phenol 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 04:44
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/60; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/582
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
130 words
A process for preparing pyrocatechol and hydroquinone, wherein phenol is reacted at the start of the reaction with substantially anhydrous hydrogen peroxide obtained by distilling off hydrogen peroxide which is in the form of non-aqueous solution whose solvent boils at a higher temperature than the phenol, together with the phenol from the higher boiling solvent, and reacting, before or after condensation, the vapors containing hydrogen peroxide which distill over, optionally following the addition of a stabilizer, wherein the reaction is carried out in the presence of a strong acid selected from the group consisting of sulfuric acid, perchloric acid, nitric acid, trifluoromethanesulfonic acid, perfluorobutanesulfonic acid, a fluorinated acid ion exchanger of a sulfonated polymeric fluorine-substituted hydrocarbon and fluorosulfonic acid at a temperature of 20°-150° C and recovering pyrocatechol and hydroquinone.
Claim 2
Dependent Claim
130 words
A process for preparing pyrocatechol and hydroquinone, wherein phenol is reacted at the start of the reaction with substantially anhydrous hydrogen peroxide obtained by distilling off hydrogen peroxide which is in the form of non-aqueous solution whose solvent boils at a higher temperature than the phenol, together with the phenol from the higher boiling solvent, and reacting, before or after condensation, the vapors containing hydrogen peroxide which distill over, optionally following the addition of a stabilizer, wherein the reaction is carried out in the presence of a strong acid selected from the group consisting of sulfuric acid, perchloric acid, nitric acid, trifluoromethanesulfonic acid, perfluorobutanesulfonic acid, a fluorinated acid ion exchanger of a sulfonated polymeric fluorine-substituted hydrocarbon and fluorosulfonic acid at a temperature of 20°-150° C and recovering pyrocatechol and hydroquinone.
Claim 3
Dependent Claim
23 words
A process as claimed in claim 1, wherein the substantially anhydrous hydrogen peroxide is reacted in solution in the phenol to be hydroxylated.
Claim 4
Dependent Claim
62 words
A process as claimed in claim 1, wherein the phenol to be hydroxylated is introduced as a vapour into a substantially anhydrous solution of hydrogen peroxide in an inert non-aqueous solvent which has a higher boiling point than the phenol, and the hydrogen peroxide and phenol vapours distilling over are reacted before or after condensation, optionally following the addition of a stabiliser.
Claim 5
Dependent Claim
30 words
A process as claimed in claim 1, wherein the higher-boiling solvent for hydrogen peroxide is an ester or N-alkyl amide of phosphoric acid, a phosphonic acid or a phosphinic acid.
Claim 6
Dependent Claim
22 words
A process as claimed in claim 1, wherein from 3 to 20 mols of phenol are used per mol of hydrogen peroxide.
Claim 7
Dependent Claim
22 words
A process as claimed in claim 5, wherein from 10 to 15 mols of phenol are used per mol of hydrogen peroxide.
Claim 8
Dependent Claim
33 words
A process as claimed in claim 1, wherein the strong acid is sulphuric acid in admixture with phosphoric acid, a fluorine-substituted sulphurized polymeric hydrocarbon, and a fluorosulphonic acid in admixture with antimony pentafluoride.
Claim 9
Dependent Claim
25 words
A process as claimed in claim 1, wherein from 0.001 mol to 2 mols of the strong acid are used per mol of hydrogen peroxide.
Claim 10
Dependent Claim
24 words
A process as claimed in claim 8, wherein from 0.1 to 0.5 mol of the strong acid are used per mol of hydrogen peroxide.
Claim 11
Dependent Claim
34 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 0.01 mol to 1 mol per mol of hydrogen peroxide.
Claim 12
Dependent Claim
26 words
A process as claimed in claim 10, wherein the stabiliser is used in a quantity of from 0.1 to 0.5 mol per mol of hydrogen peroxide.
Claim 13
Dependent Claim
26 words
A process as claimed in claim 10, wherein the stabiliser is an ester of N-alkyl amide of phosphoric acid, a phosphonic acid or a phosphinic acid.
Claim 14
Dependent Claim
16 words
A process as claimed in claim 1, wherein the temperature is from 30° to 100° C.
Claim 15
Dependent Claim
20 words
A process as claimed in claim 1, wherein the reaction is carried out continuously with recycling of the unreacted reactants.
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) | 1980-10-10 | 1981-04-11 | 1981-10-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-10-10 | 1985-04-11 | 1985-10-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-10-10 | 1989-04-11 | 1989-10-11 | $7700.00 | Window Closed / Lapsed |