Patent US4649225A successfully refreshed from Google Patents.
US4649225A
Expired / Lapsed
US
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Hydrogenolysis of polyalkylene glycols to produce monoethylene glycol monoalkyl ethers, monoethylene glycol and ethanol
Assignee: Union Carbide Corp
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Filing: 1985-05-21
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Granted: 1987-03-10
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Expires: 2005-05-21
Abstract
Abstract This invention relates to a process for selectively cleaving a polyalkylene glycol, e.g., diethylene glycol, containing at least one ether group therein at a carbon-to-oxygen covalent bond and independently at a carbon-to-carbon covalent bond by heating the polyalkylene glycol with molecular hydrogen in the presence of a hydrogenation catalyst containing iridium to produce at least one of monoethylene glycol monoethyl ether, monoethylene glycol monomethyl ether, monoethylene glycol and ethanol. Monoethylene glycol monoethyl ether can be produced in significant amounts by employing the process of this invention.
Inventors
- 👤 William J. Bartley
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 23:23
CPC Classifications
C; C07; C07C; C07C29/00; C07C29/09; C07C29/10; C07C29/60; C07C41/00; C07C41/01; C07C41/18; C07C41/26
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
45 words
A process for making monoethylene glycol monoethyl ether from polyethylene glycol comprising providing said polyethylene glycol with molecular hydrogen under hydrogenolysis conditions including elevated temperature and the presence of hydrogenation catalyst comprising iridium, sufficient to cleave said polyethylene glycol at a carbon-to-oxygen terminal hydroxy bond.
Claim 2
Dependent Claim
45 words
A process for making monoethylene glycol monoethyl ether from polyethylene glycol comprising providing said polyethylene glycol with molecular hydrogen under hydrogenolysis conditions including elevated temperature and the presence of hydrogenation catalyst comprising iridium, sufficient to cleave said polyethylene glycol at a carbon-to-oxygen terminal hydroxy bond.
Claim 3
Dependent Claim
28 words
The process of claim 1 wherein the hydrogenolysis conditions include superatomspheric pressure and provide a selectivity to monoethylene glycol monoethyl ether of at least about 35 molar percent.
Claim 4
Dependent Claim
11 words
The process of claim 1 wherein polyethylene glycol is diethylene glycol.
Claim 5
Dependent Claim
19 words
The process of claim 1 wherein the hydrogenation catalyst is a composition comprising about 5 percent by weight iridium.
Claim 6
Dependent Claim
31 words
The process of claim 1 wherein the polyethylene glycol and molecular hydrogen are present in a molar ratio of molecular hydrogen to polyethylene glycol of from about 1:20 to about 2000:1.
Claim 7
Dependent Claim
34 words
The process of claim 1 wherein the hydrogenation catalyst is present in an amount of from about 0.01 weight percent to about 50 weight percent based on the total weight of the reaction mixture.
Claim 8
Dependent Claim
18 words
The process of claim 1 wherein the reaction temperature is from about 150° C. to about 350° C.
Claim 9
Dependent Claim
22 words
The process of claim 1 wherein the initial pressure resulting from molecular hydrogen is from about 100 psig to about 4000 psig.
Claim 10
Dependent Claim
77 words
A process for making monoethylene glycol monoethyl ether and at least one of monoethylene glycol monoethyl ether and ethanol, from polyethylene glycol comprising providing said polyethylene glycol with molecular hydrogen under hydrogenolysis conditions including elevated temperature and the presence of hydrogenation catalyst comprising iridium, sufficient to cleave said polyethylene glycol at a carbon-to-oxygen covalent bond to provide at least one of monoethylene glycol monoethyl ether and ethanol and a carbon-to-carbon bond to provide monoethylene glycol monoethyl ether.
Claim 11
Dependent Claim
77 words
A process for making monoethylene glycol monoethyl ether and at least one of monoethylene glycol monoethyl ether and ethanol, from polyethylene glycol comprising providing said polyethylene glycol with molecular hydrogen under hydrogenolysis conditions including elevated temperature and the presence of hydrogenation catalyst comprising iridium, sufficient to cleave said polyethylene glycol at a carbon-to-oxygen covalent bond to provide at least one of monoethylene glycol monoethyl ether and ethanol and a carbon-to-carbon bond to provide monoethylene glycol monoethyl ether.
Claim 12
Dependent Claim
22 words
The process of claim 9 wherein monoethylene glycol monoethyl ether is produced at a selectivity of at least about 35 molar percent.
References Cited (Backward Citations)
US1953548A
Cited
US2497812A
Cited
US2658081A
Cited
US2768978A
Cited
US3833634A
Cited
DE2434057A1
Cited
US3975449A
Cited
US4088700A
Cited
DE2716690A1
Cited
US4091041A
Cited
DE2900279A1
Cited
FR2447363A1
Cited
JPH109908A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-03-09 | 1990-09-08 | 1991-03-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-03-09 | 1994-09-08 | 1995-03-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-03-09 | 1998-09-08 | 1999-03-10 | $7700.00 | Window Closed / Lapsed |