US4120761A
Expired / Lapsed
US
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Electrochemical process for the preparation of acetals of 2-haloaldehydes
Assignee: Monsanto Co
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Filing: 1977-12-15
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Granted: 1978-10-17
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Expires: 1997-12-15
Abstract
Abstract Electrolysis of a substantially anhydrous electrolysis medium comprising a primary alcohol having at least one beta-hydrogen atom and anhydrous hydrogen halide selected from the group consisting of hydrogen chloride and hydrogen bromide yields acetals of 2-haloaldehydes corresponding to the primary alcohol.
Inventors
- 👤 Donald A. White
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 17:05
CPC Classifications
C; C25; C25B; C25B3/00; C25B3/20; C25B3/23; C25B3/01; C25B3/07
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
63 words
A process for the preparation of acetals of 2-haloaldehydes which comprises subjecting a substantially anhydrous liquid electrolysis medium comprising a primary alcohol having at least one beta hydrogen atom and an anhydrous hydrogen halide selected from the group consisting of hydrogen chloride and hydrogen bromide to electrolysis in an electrolytic cell to yield the acetal of the 2-haloaldehyde corresponding to the primary alcohol.
Claim 2
Dependent Claim
63 words
A process for the preparation of acetals of 2-haloaldehydes which comprises subjecting a substantially anhydrous liquid electrolysis medium comprising a primary alcohol having at least one beta hydrogen atom and an anhydrous hydrogen halide selected from the group consisting of hydrogen chloride and hydrogen bromide to electrolysis in an electrolytic cell to yield the acetal of the 2-haloaldehyde corresponding to the primary alcohol.
Claim 3
Dependent Claim
11 words
The process of claim 1 wherein the primary alcohol is ethanol.
Claim 4
Dependent Claim
12 words
The process of claim 1 wherein the primary alcohol is n-butyl alcohol.
Claim 5
Dependent Claim
12 words
The process of claim 1 wherein the primary alcohol is isobutyl alcohol.
Claim 6
Dependent Claim
28 words
The process of claim 1 wherein the primary alcohol is ethanol, the anhydrous hydrogen halide is hydrogen chloride, and the acetal of the 2-haloaldehyde is chloroacetaldehyde diethyl acetal.
Claim 7
Dependent Claim
29 words
The process of claim 1 wherein the primary alcohol is n-butyl alcohol, the anhydrous hydrogen halide is hydrogen chloride, and the acetal of the 2-haloaldehyde is 2-chloro-n-butyraldehyde di-n-butyl acetal.
Claim 8
Dependent Claim
29 words
The process of claim 1 wherein the primary alcohol is n-butyl alcohol, the anhydrous hydrogen halide is hydrogen bromide, and the acetal of the 2-haloaldehyde is 2-bromo-n-butyraldehyde di-n-butyl acetal.
Claim 9
Dependent Claim
24 words
The process of claim 1 wherein the molar ratio of anhydrous hydrogen halide to the primary alcohol is between about 1:0.1 and about 1:10.
Claim 10
Dependent Claim
18 words
The process of claim 1 wherein the reaction temperature is between about 0° C. and about 100° C.
Claim 11
Dependent Claim
15 words
The process of claim 1 wherein a graphite anode and a graphite cathode are used.
Claim 12
Dependent Claim
13 words
The process of claim 1 wherein the electrolytic cell is an undivided cell.
Claim 13
Dependent Claim
14 words
The process of claim 1 wherein the liquid electrolysis medium contains an added solvent.
Claim 14
Dependent Claim
20 words
The process of claim 12 wherein the added solvent is selected from the group consisting of methanol and methylene chloride.
Claim 15
Dependent Claim
65 words
A process for the preparation of dimethyl acetals of 2-haloaldehydes which comprises subjecting a substantially anhydrous liquid electrolysis medium comprising a primary alcohol having at least one beta hydrogen atom, anhydrous hydrogen halide selected from the group consisting of hydrogen chloride and hydrogen bromide, and methanol to electrolysis in an electrolytic cell to yield the dimethyl acetal of the 2-haloaldehyde corresponding to the primary alcohol.
Claim 16
Dependent Claim
65 words
A process for the preparation of dimethyl acetals of 2-haloaldehydes which comprises subjecting a substantially anhydrous liquid electrolysis medium comprising a primary alcohol having at least one beta hydrogen atom, anhydrous hydrogen halide selected from the group consisting of hydrogen chloride and hydrogen bromide, and methanol to electrolysis in an electrolytic cell to yield the dimethyl acetal of the 2-haloaldehyde corresponding to the primary alcohol.
Claim 17
Dependent Claim
54 words
The process of claim 14 wherein the concentration of the primary alcohol in methanol is between about 1.0 molar and about 6.0 molar; the molar ratio of the hydrogen halide to the primary alcohol is between about 1:0.1 and about 1:10, and the reaction temperature is between about 0° C. and about 100° C.
Claim 18
Dependent Claim
30 words
The process of claim 14 wherein the primary alcohol is isobutyl alcohol, the anhydrous hydrogen halide is hydrogen chloride, and the dimethyl acetal of the 2-haloaldehyde is 2-chloroisobutyraldehyde dimethyl acetal.
References Cited (Backward Citations)
US3257298A
Cited
US4046652A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-10-16 | 1982-04-17 | 1982-10-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-16 | 1986-04-17 | 1986-10-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-16 | 1990-04-17 | 1990-10-17 | $7700.00 | Window Closed / Lapsed |