US4174352A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for aqueous chromate ion oxidation of allylic halides and halomethylated aromatics to allylic and aromatic aldehydes
Assignee: Dow Chemical Co
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Filing: 1978-05-08
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Granted: 1979-11-13
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Expires: 1998-05-08
Abstract
Abstract A process for preparing an allylic or an aromatic aldehyde, such as acrolein or benzaldehyde, the process comprising contacting in a basic, liquid, biphasic mixture and at reactive conditions an allylic halide or a halomethylated aromatic, such as allyl or benzyl chloride, with a divalent chromate ion, is improved by contacting the allylic halide or halomethylated aromatic with the divalent chromate ion in the presence of a catalytic amount of a quaternary ammonium and/or phosphonium salt, such as tetra-n-butylammonium chloride. The improved process is faster, cleaner and more complete than the process of the prior art.
Inventors
- 👤 Thomas H. Fisher
- 👤 William Dowd
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 03:58
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/27
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
98 words
An improved process for preparing an aldehyde of the formula A--CHO).sub.n (I) wherein A is an allylic, aryl or an inertly-substituted allylic or aryl radical and n is an integer of at least 1, the process comprising contacting in a basic, liquid, biphasic mixture and at reactive conditions a compound of the formula A--CH.sub.2 X).sub.n (II) wherein X is chloride, bromide or iodide and A and n are as previously defined, with divalent chromate ion, the improvement comprising contacting II with the chromate ion in the presence of a catalytic amount of a quaternary ammonium and/or phosphonium salt.
Claim 2
Dependent Claim
98 words
An improved process for preparing an aldehyde of the formula A--CHO).sub.n (I) wherein A is an allylic, aryl or an inertly-substituted allylic or aryl radical and n is an integer of at least 1, the process comprising contacting in a basic, liquid, biphasic mixture and at reactive conditions a compound of the formula A--CH.sub.2 X).sub.n (II) wherein X is chloride, bromide or iodide and A and n are as previously defined, with divalent chromate ion, the improvement comprising contacting II with the chromate ion in the presence of a catalytic amount of a quaternary ammonium and/or phosphonium salt.
Claim 3
Dependent Claim
32 words
The process of claim 1 where the quaternary ammonium and/or phosphonium salt is present in an amount of from about 1 to about 30 mole percent based on the moles of II.
Claim 4
Dependent Claim
32 words
The process of claim 1 whre the quaternary ammonium and/or phosphonium salt is present in an amount of from about 2 to about 10 mole percent based on the moles of II.
Claim 5
Dependent Claim
58 words
The process of claim 1, 2 or 3 where the quaternary ammonium and/or phosphonium salt is of the formula R"R'"R.sup.IV R.sup.V Q.sup.⊕ An.sup.⊖ (III) where Q.sup.⊕ is a quaternized atom of nitrogen or phosphorus and R"-R V are hydrocarbyl groups of 1 to about 16 carbon atoms each with a combined minimum total of about 10 carbon atoms.
Claim 6
Dependent Claim
20 words
The process of claim 4 where the quaternary ammonium and/or phosphonium salt is benzyltrimethyl-, benzyltriethyl- or tetra-n-butylammonium chloride or bromide.
References Cited (Backward Citations)
US3992432A
Cited
US4061664A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-11-12 | 1983-05-14 | 1983-11-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-11-12 | 1987-05-14 | 1987-11-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-11-12 | 1991-05-14 | 1991-11-13 | $7700.00 | Window Closed / Lapsed |