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US4139542A
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Process for the preparation of 2-alkoxytetrahydrofurans via hydroformylation of allylic alcohols
Assignee: General Electric Co
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Filing: 1977-11-07
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Granted: 1979-02-13
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Expires: 1997-11-07
Abstract
Abstract 2-Alkoxytetrahydrofurans are prepared in higher yields when an allylic alcohol is hydroformylated in the presence of an alkanol and a rhodium/tertiaryphosphine-complex if an acid co-catalyst is used. The products are useful, inter alia, as intermediates in the preparation of butanediols and substituted derivatives thereof.
Inventors
- 👤 William E. Smith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 17:26
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/04; C07D307/18; C07D307/20; C07C; C07C45/00; C07C45/49
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
73 words
In a process for preparing a 2-alkoxytetrahydrofuran or 2-alkoxy-substituted tetrahydrofuran by contacting an allylic alcohol, carbon monoxide, hydrogen and a corresponding alkanol with a rhodium/tertiaryphosphine complex hydroformylation catalyst, the improvement which comprises using an acid co-catalyst with such rhodium complex catalyst, said acid co-catalyst being both (i) strong enough to promote the desired conversion yet not so strong as to significantly decompose initial oxo products and (ii) inert with respect to the reactants.
Claim 2
Dependent Claim
73 words
In a process for preparing a 2-alkoxytetrahydrofuran or 2-alkoxy-substituted tetrahydrofuran by contacting an allylic alcohol, carbon monoxide, hydrogen and a corresponding alkanol with a rhodium/tertiaryphosphine complex hydroformylation catalyst, the improvement which comprises using an acid co-catalyst with such rhodium complex catalyst, said acid co-catalyst being both (i) strong enough to promote the desired conversion yet not so strong as to significantly decompose initial oxo products and (ii) inert with respect to the reactants.
Claim 3
Dependent Claim
24 words
A process as defined in claim 1 wherein said co-catalyst has a pK a of from about 1.5 to about 3.5 in aqueous solution.
Claim 4
Dependent Claim
18 words
A process as defined in claim 1 carried out at a pressure in the range of 100-5000 psi.
Claim 5
Dependent Claim
18 words
A process as defined in claim 3 carried out at a pressure in the range of 300-1200 psi.
Claim 6
Dependent Claim
19 words
A process as defined in claim 1 carried out at a temperature between about 25° C. and 200° C.
Claim 7
Dependent Claim
18 words
A process as defined in claim 5 carried out at a temperature in the range of 70-150° C.
Claim 8
Dependent Claim
12 words
A process as defined in claim 1 wherein said triarylphosphine is triphenylphosphine.
Claim 9
Dependent Claim
18 words
A process as defined in claim 1 wherein said allylic alcohol comprises allyl alcohol, methallyl alcohol or 2-methyl-3-buten-2-ol.
Claim 10
Dependent Claim
15 words
A process as defined in claim 1 wherein said alkanol comprises methanol, n-propanol or isobutanol.
Claim 11
Dependent Claim
65 words
A process as defined in claim 1 wherein said allylic alcohol is selected from those of the formula: ##STR4## wherein R is hydrogen or alkyl from 1 to 8 carbon atoms and said alkanol is selected from among those of the formula: R.sup.1 OH wherein R 1 is alkyl of from 1 to 8 carbon atoms or hydroxyalkyl of from 2 to 8 carbon atoms.
Claim 12
Dependent Claim
42 words
In a process for preparing a 2-alkoxytetrahydrofuran or 2-alkoxy-substituted tetrahydrofuran by contacting an allylic alcohol, carbon monoxide, hydrogen and a corresponding alkanol with a rhodium/tertiaryphosphine complex hydroformylation catalyst, the improvement which comprises using an o-phthalic acid co-catalyst with such rhodium complex catalyst.
Claim 13
Dependent Claim
42 words
In a process for preparing a 2-alkoxytetrahydrofuran or 2-alkoxy-substituted tetrahydrofuran by contacting an allylic alcohol, carbon monoxide, hydrogen and a corresponding alkanol with a rhodium/tertiaryphosphine complex hydroformylation catalyst, the improvement which comprises using an o-phthalic acid co-catalyst with such rhodium complex catalyst.
Claim 14
Dependent Claim
42 words
In a process for preparing a 2-alkoxytetrahydrofuran or 2-alkoxy-substituted tetrahydrofuran by contacting an allylic alcohol, carbon monoxide, hydrogen and a corresponding alkanol with a rhodium/tertriaryphosphine complex hydroformylation catalyst, the improvement which comprises using a 4,5-dichlorophthalic acid co-catalyst with such rhodium complex catalyst.
Claim 15
Dependent Claim
42 words
In a process for preparing a 2-alkoxytetrahydrofuran or 2-alkoxy-substituted tetrahydrofuran by contacting an allylic alcohol, carbon monoxide, hydrogen and a corresponding alkanol with a rhodium/tertriaryphosphine complex hydroformylation catalyst, the improvement which comprises using a 4,5-dichlorophthalic acid co-catalyst with such rhodium complex catalyst.
Claim 16
Dependent Claim
42 words
In a process for preparing a 2-alkoxytetrahydrofuran or 2-alkoxy-substituted tetrahydrofuran by contacting an allylic alcohol, carbon monoxide, hydrogen and a corresponding alkanol with a rhodium/tertiaryphosphine complex hydroformylation catalyst, the improvement which comprises using a phosphoric acid co-catalyst with such rhodium complex catalyst.
Claim 17
Dependent Claim
42 words
In a process for preparing a 2-alkoxytetrahydrofuran or 2-alkoxy-substituted tetrahydrofuran by contacting an allylic alcohol, carbon monoxide, hydrogen and a corresponding alkanol with a rhodium/tertiaryphosphine complex hydroformylation catalyst, the improvement which comprises using a phosphoric acid co-catalyst with such rhodium complex catalyst.
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) | 1982-02-12 | 1982-08-14 | 1983-02-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-02-12 | 1986-08-14 | 1987-02-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-02-12 | 1990-08-14 | 1991-02-13 | $7700.00 | Window Closed / Lapsed |