Patent US3670029A successfully refreshed from Google Patents.
US3670029A
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Preparation of unsaturated ethers
Assignee: ExxonMobil Technology and Engineering Co
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Filing: 1969-03-19
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Granted: 1972-06-13
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Expires: 1989-03-19
Abstract
Abstract Unsaturated ethers are prepared through the reaction of C4 to C6 aliphatic conjugated diolefins with a monohydroxy alcohol in the presence of a catalyst system based upon zero valent nickel. The preferred catalyst system is made up of a zero valent nickel material, a phosphine or isonitrile activator and further, if desired, an inorganic or organic base cocatalyst. The reaction is conducted at moderate temperature and pressure conditions. The unsaturated ethers can be catalytically hydrogenated to useful ether solvent media.
Inventors
- 👤 Michael G Romanelli
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 14:32
CPC Classifications
B; B01; B01J; B01J31/00; B01J31/16; B01J31/24; B01J31/2404; B01J31/18; B01J31/1805; C; C10; C10M; C10M3/00; B01J2231/00; B01J2231/30; B01J2231/32; B01J2231/323; B01J2531/00; B01J2531/80; B01J2531/84; B01J2531/847; B01J31/22; B01J31/2282; B01J31/2291; B01J31/2295; C10M2207/00; C10M2207/28; C10M2207/281; C10M2207/282; C10M2207/283; C10M2207/286; C10N; C10N2040/00; C10N2040/08
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
32 words
The process of claim 1 wherein said zero valent nickel material is employed in amounts ranging from about 0.001 to 1 mole per liter of alcohol reagent present within the reaction zone.
Claim 2
Dependent Claim
10 words
The process of claim 1 wherein said diolefin is butadiene.
Claim 3
Dependent Claim
34 words
The process of claim 1 wherein said process is conducted in the further presence of a basic cocatalyst material selected from the group consisting of quaternary hydrocarbyl ammonium hydroxides, and quaternary hydrocarbyl ammonium alkoxides.
Claim 4
Dependent Claim
27 words
The process of claim 4 wherein said basic cocatalyst material is employed in amounts ranging from about 0.001 to 1 mole of base per liter of alcohol.
Claim 5
Dependent Claim
127 words
A process for the formation of unsaturated ethers which comprises contacting in the liquid phase said liquid phase being free of oxygen, a solution of a C4 to C6 acyclic conjugated diolefin and a monohydroxy coreactant selected from the group consisting of phenol and lower alkanols having from one to eight carbon atoms in the presence of a zero valent nickel material, said zero valent nickel material selected from the group consisting of bis(1,5-cyclooctadiene)nickel, bis(pi-allyl)nickel, bis(cyclopentadienyl)nickel and tetrakis(triphenylphosphine)nickel, and a molar excess, relative to said zero valent nickel material, of a triorganophosphine compound selected from the group consisting of triphenylphosphine, tribenzylphosphine, tributylphosphine, tricyclohexylphosphine, diethylphenylphosphine, and phenyldibutylphosphine, said contacting conducted at a temperature ranging from about 0* to 125* C. and thereafter recovering a yield of said products.
Claim 6
Dependent Claim
18 words
The process of claim 6, wherein said zero valent nickel material is combined with said activator as tetrakis(triphenylphosphine)nickel.
Claim 7
Dependent Claim
37 words
The process of claim 6 wherein said contacting is conducted in the further presence of a basic cocatalyst selected from the group consisting of quaternary hydrocarbyl ammonium hydroxides and alkoxides having from four to 12 carbon atoms.
Claim 8
Dependent Claim
15 words
The process of claim 6 wherein said alkanol has from one to five carbon atoms.
Claim 9
Dependent Claim
19 words
The process of claim 6 wherein said process is conducted at a temperature ranging from 50* to 100* C.
Claim 10
Dependent Claim
23 words
The process of claim 6 wherein at least about 10 moles of phosphine compound is employed per mole of zero valent nickel compound.
Claim 11
Dependent Claim
10 words
The process of claim 8 wherein said diolefin is butadiene.
Claim 12
Dependent Claim
28 words
The process of claim 11 wherein said zero valent nickel material is bis(1,5-cyclooctadiene)nickel, said triorganophosphine compound is triphenylphosphine, and said basic cocatalyst is a quaternary hydrocarbyl ammonium hydroxide.
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) | 1975-06-13 | 1975-12-13 | 1976-06-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-06-13 | 1979-12-13 | 1980-06-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-06-13 | 1983-12-13 | 1984-06-13 | $7700.00 | Window Closed / Lapsed |