US4246203A
Expired / Lapsed
US
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Process for the production of a phenol and a carbonyl compound by the catalyzed decomposition of an aromatic hydroperoxide
Assignee: BP Chemicals Ltd
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Filing: 1979-08-09
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Granted: 1981-01-20
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Expires: 1999-08-09
Abstract
Abstract The invention relates to a process in which an aromatic hydroperoxide of formula: <IMAGE> wherein independently R1 is methyl or ethyl, R2 is hydrogen, methyl or ethyl, or where R1 and R2 together form an alicyclic ring of 5 or 6 carbon atoms, R3 is hydrogen or alkyl and R4 and R5 are hydrogen, alkyl or together form an automatic ring, n is 0, 1 or 2 and n1 is 1 or 2, is converted to a phenol and a carbonyl compound in a catalyzed cleavage decomposition reaction. In particular cumene hydroperoxide is converted to phenol and acetone. Instead of removing the decomposition products from the reactor in the liquid phase and dissipating the reaction heat as in prior art processes the heat is used to remove the phenol and the carbonyl compound in the vapor phase leaving a liquid residue of higher-boiling compounds and catalyst in the case where a liquid cleavage catalyst is employed. Although a wide range of both solid and liquid cleavage catalysts may be used sulphuric acid is preferred. Various additives, including the hydrocarbon from which the hydroperoxide is derived and polar reaction products may be added. Typical reaction conditions are temperatures in the range 120 DEG to 200 DEG C. and either atmospheric or sub-atmospheric pressure. The process of the invention avoids the conventional catalyst neutralization and removal steps.
Inventors
- 👤 Max M. Wirth
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 19:18
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/08; C07C45/00; C07C45/51; C07C45/53
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
176 words
A process in which a hydroperoxide of an aromatic compound of formula: ##STR4## wherein independently R 1 is methyl or ethyl, R 2 hydrogen, methyl or ethyl, or where R 1 and R 2 together form an alicyclic ring of 5 or 6 carbon atoms, R 3 is hydrogen or alkyl and R 4 and R 5 are hydrogen, alkyl or together form an aromatic ring, n is 0, 1 or 2 and n 1 is 1 or 2, is converted to a volatile phenol and a carbonyl compound in a cleavage decomposition reaction which process comprises continuously feeding said hydroperoxide to a reactor in which it is contacted with a cleavage decomposition catalyst at an elevated temperature and at a pressure such that cleavage decomposition of the hydroperoxide occurs, said reactor being capable of separating the vapourised relatively low-boiling components from higher-boiling liquid products and catalyst and continuously removing from said reactor a mixture in the vapour phase containing said phenol and said carbonyl compound cleavage decomposition products and in the liquid phase higher-boiling residues.
Claim 2
Dependent Claim
176 words
A process in which a hydroperoxide of an aromatic compound of formula: ##STR4## wherein independently R 1 is methyl or ethyl, R 2 hydrogen, methyl or ethyl, or where R 1 and R 2 together form an alicyclic ring of 5 or 6 carbon atoms, R 3 is hydrogen or alkyl and R 4 and R 5 are hydrogen, alkyl or together form an aromatic ring, n is 0, 1 or 2 and n 1 is 1 or 2, is converted to a volatile phenol and a carbonyl compound in a cleavage decomposition reaction which process comprises continuously feeding said hydroperoxide to a reactor in which it is contacted with a cleavage decomposition catalyst at an elevated temperature and at a pressure such that cleavage decomposition of the hydroperoxide occurs, said reactor being capable of separating the vapourised relatively low-boiling components from higher-boiling liquid products and catalyst and continuously removing from said reactor a mixture in the vapour phase containing said phenol and said carbonyl compound cleavage decomposition products and in the liquid phase higher-boiling residues.
Claim 3
Dependent Claim
33 words
A process according to claim 1 wherein a liquid cleavage decomposition catalyst is fed continuously to said reactor and is removed continuously from said reactor in said liquid phase with said higher-boiling residues.
Claim 4
Dependent Claim
19 words
A process according to claim 1 wherein said reactor contains a fixed bed of a solid cleavage decomposition catalyst.
Claim 5
Dependent Claim
67 words
A process according to claim 1 wherein said hydroperoxide has the formula: ##STR5## wherein independently R 1 is methyl or ethyl, R 2 is hydrogen, methyl or ethyl or where R 1 and R 2 together form an alicyclic ring of 5 or 6 carbon atoms and wherein R 3 is hydrogen or alkyl, n is 0, 1 or 2 and n 1 is 1 or 2.
Claim 6
Dependent Claim
21 words
A process according to claim 4 wherein said hydroperoxide of formula (II) is cumene-, cymene-, cyclohexylbenzene-, diisopropylbenzene-, ethylbenzene-, or sec-butylbenzene hydroperoxide.
Claim 7
Dependent Claim
15 words
A process according to claim 1 wherein said hydroperoxide is fed together with a diluent.
Claim 8
Dependent Claim
19 words
A process according to claim 6 wherein said diluent is the aromatic hydrocarbon from which said hydroperoxide is derived.
Claim 9
Dependent Claim
23 words
A process according to claim 1 wherein there is added a reaction modifier which is one or more polar hydroperoxide cleavage decomposition products.
Claim 10
Dependent Claim
62 words
A process according to claim 1 wherein said hydroperoxide concentration is such that the heat evolved during decomposition is the amount required to remove from said reactor at said cleavage decomposition temperature and pressure said mixture in said vapour phase containing said phenol and said carbonyl compound and in said liquid phase higher-boiling residues, without providing additional heat or removing surplus heat.
Claim 11
Dependent Claim
14 words
A process according to claim 1 wherein said cleavage decomposition catalyst is sulphuric acid.
Claim 12
Dependent Claim
13 words
A process according to claim 1 wherein said pressure is atmospheric or sub-atmospheric.
Claim 13
Dependent Claim
17 words
A process according to claim 1 wherein said reactor is a short column provided with a reboiler.
Claim 14
Dependent Claim
110 words
A process in which cumene hydroperoxide is converted to phenol and acetone in a cleavage decomposition reaction which process comprises continuously feeding said hydroperoxide to a reactor in which it is contacted with a cleavage decomposition catalyst at an elevated temperature and at a pressure such that cleavage decomposition of said hydroperoxide occurs, said reactor being capable of separating vapourised relatively low-boiling components from higher-boiling liquid products and catalyst, and continuously removing from said reactor a mixture in the vapour phase containing compounds having a boiling point at standard temperature and pressure of less than 200° C., including said phenol and said acetone, and in the liquid phase higher-boiling residues.
Claim 15
Dependent Claim
110 words
A process in which cumene hydroperoxide is converted to phenol and acetone in a cleavage decomposition reaction which process comprises continuously feeding said hydroperoxide to a reactor in which it is contacted with a cleavage decomposition catalyst at an elevated temperature and at a pressure such that cleavage decomposition of said hydroperoxide occurs, said reactor being capable of separating vapourised relatively low-boiling components from higher-boiling liquid products and catalyst, and continuously removing from said reactor a mixture in the vapour phase containing compounds having a boiling point at standard temperature and pressure of less than 200° C., including said phenol and said acetone, and in the liquid phase higher-boiling residues.
Claim 16
Dependent Claim
21 words
A process according to claim 13 wherein said cumene hydroperoxide feed to said reactor contains as impurities phenyldimethyl carbinol and/or acetophenone.
Claim 17
Dependent Claim
15 words
A process according to claim 13 wherein said cumene hydroperoxide feed contains cumene as diluent.
Claim 18
Dependent Claim
17 words
A process according to claim 13 wherein said cumene hydroperoxide feed contains acetone as a reaction modifier.
Claim 19
Dependent Claim
41 words
A process according to claim 13 wherein said cumene hydroperoxide is fed as a solution in a solvent selected from acetone, acetophenone cumene and mixtures thereof, the concentration of said cumene hydroperoxide being in the range 40 to 50% by weight.
Claim 20
Dependent Claim
65 words
A process according to claim 13 wherein said catalyst is sulphuric acid which is fed to said reactor as a dilute solution in a solvent selected from acetone, acetophenone, cumene and mixtures thereofin an amount of from 50 to 2000 ppm of free acid based on the weight of said feed and is removed from said reactor in the liquid phase with said higher-boiling residues.
Claim 21
Dependent Claim
21 words
A process according claim 13 said temperature is in the range 120° to 200° l C. and said pressure is atmospheric.
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) | 1984-01-20 | 1984-07-21 | 1985-01-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-01-20 | 1988-07-21 | 1989-01-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-01-20 | 1992-07-21 | 1993-01-20 | $7700.00 | Window Closed / Lapsed |