Patent US4390732A successfully refreshed from Google Patents.
US4390732A
Expired / Lapsed
US
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Process for the production of guaiacol glycerine ether
Assignee: Evonik Operations GmbH
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Filing: 1982-02-10
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Granted: 1983-06-28
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Expires: 2002-02-10
Abstract
Abstract Guaiacol glycerine ether is obtained in very good yield and in very high purity by reacting glycidol with o-methyoxyphenol in the presence of an alkali hydroxide, an alkali alcoholate, an alkali cyanate or an alkali thiocyanate at 80° to 150° C. An especially effective purification of the crude product can be obtained by adding hydrogen peroxide, preferably prior to cooling.
Inventors
- 👤 Wolfgang Merk
- 👤 Rudolf M. Wagner
- 👤 Peter Werle
- 👤 Robert S. Nygren
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 14:33
CPC Classifications
C; C07; C07C; C07C41/00; C07C41/01; C07C41/02; C07C41/03
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
41 words
A process for the production of guaiacol glycerine ether comprising reacting o-methoxyphenol with glycidol in the presence of a catalyst selected from the group consisting of alkali metal hydroxides, alkali metal alcoholates, alkali metal cyanates, alkali metal thiocyanates and mixture thereof.
Claim 2
Dependent Claim
41 words
A process for the production of guaiacol glycerine ether comprising reacting o-methoxyphenol with glycidol in the presence of a catalyst selected from the group consisting of alkali metal hydroxides, alkali metal alcoholates, alkali metal cyanates, alkali metal thiocyanates and mixture thereof.
Claim 3
Dependent Claim
14 words
A process according to claim 1 carried out in the absence of a solvent.
Claim 4
Dependent Claim
23 words
A process according to claim 1 wherein the catalyst is employed in an amount of 0.0003 to 0.05 mole per mole of guaiacol.
Claim 5
Dependent Claim
13 words
A process according to claim 3 carried out in the absence of solvent.
Claim 6
Dependent Claim
23 words
A process according to claim 3 wherein the catalyst is employed in an amount of 0.0003 to 0.1 mole per mole of guaiacol.
Claim 7
Dependent Claim
18 words
A process according to claim 5 wherein there is used as the catalyst sodium hydroxide in powdered form.
Claim 8
Dependent Claim
18 words
A process according to claim 3 wherein there is used as the catalyst sodium hydroxide in powdered form.
Claim 9
Dependent Claim
18 words
A process according to claim 1 wherein there is used as the catalyst sodium hydroxide in powdered form.
Claim 10
Dependent Claim
18 words
A process according to claim 5 wherein there is used as the catalyst potassium cyanate in powdered form.
Claim 11
Dependent Claim
18 words
A process according to claim 3 wherein there is used as the catalyst potassium cyanate in powdered form.
Claim 12
Dependent Claim
18 words
A process according to claim 1 wherein there is used as the catalyst potassium cyanate in powdered form.
Claim 13
Dependent Claim
81 words
A process according to claim 3 carried out in the absence of a solvent and including the step of adding aqueous hydrogen peroxide in an amount of 0.05 to 0.1 mole (calculated as 100 weight % H 2 O 2 ) per mole of guaiacol employed to the melt obtained after the reaction at the temperature present at the end of the reaction, subsequently adding a solvent for the guaiacol glycerine ether and crystallizing the guaiacol glycerine ether from said solvent.
Claim 14
Dependent Claim
81 words
A process according to claim 7 carried out in the absence of a solvent and including the step of adding aqueous hydrogen peroxide in an amount of 0.05 to 0.1 mole (calculated as 100 weight % H 2 O 2 ) per mole of guaiacol employed to the melt obtained after the reaction at the temperature present at the end of the reaction, subsequently adding a solvent for the guaiacol glycerine ether and crystallizing the guaiacol glycerine ether from said solvent.
Claim 15
Dependent Claim
81 words
A process according to claim 10 carried out in the absence of a solvent and including the step of adding aqueous hydrogen peroxide in an amount of 0.05 to 0.1 mole (calculated as 100 weight % H 2 O 2 ) per mole of guaiacol employed to the melt obtained after the reaction at the temperature present at the end of the reaction, subsequently adding a solvent for the guaiacol glycerine ether and crystallizing the guaiacol glycerine ether from said solvent.
Claim 16
Dependent Claim
81 words
A process according to claim 1 carried out in the absence of a solvent and including the step of adding aqueous hydrogen peroxide in an amount of 0.05 to 0.1 mole (calculated as 100 weight % H 2 O 2 ) per mole of guaiacol employed to the melt obtained after the reaction at the temperature present at the end of the reaction, subsequently adding a solvent for the guaiacol glycerine ether and crystallizing the guaiacol glycerine ether from said solvent.
Claim 17
Dependent Claim
17 words
A process according to claim 12 wherein the aqueous hydrogen peroxide contains 30-70 weight % hydrogen peroxide.
Claim 18
Dependent Claim
39 words
A process according to claim 3 wherein there is added 0.05 to 0.1 mole of aqueous hydrogen peroxide (calculated as 100 weight % H 2 O 2 ) per mole of guaiacol after the reaction to destroy color-forming impurities.
Claim 19
Dependent Claim
39 words
A process according to claim 1 wherein there is added 0.05 to 0.1 mole of aqueous hydrogen peroxide (calculated as 100 weight % H 2 O 2 ) per mole of guaiacol after the reaction to destroy color-forming impurities.
Claim 20
Dependent Claim
24 words
A process according to claim 1 wherein there is added aqueous hydrogen peroxide after the reaction in an amount sufficient to destroy color-forming impurities.
Claim 21
Dependent Claim
24 words
A process according to claim 2 comprising introducing glycidol into molten catalyst containing guaiacol so that glycidol is instantaneously reacted to guaiacol glycerine ether.
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) | 1986-06-27 | 1986-12-27 | 1987-06-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-06-27 | 1990-12-27 | 1991-06-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-06-27 | 1994-12-27 | 1995-06-28 | $7700.00 | Window Closed / Lapsed |