US4797478A
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Process for producing color-stable, industrial-grade methyl glucoside
Assignee: Unilever Bestfoods North America
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Filing: 1987-03-23
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Granted: 1989-01-10
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Expires: 2007-03-23
Abstract
Abstract A process for producing an industrial-grade methyl glucoside with improved color stability. Glucose is reacted in two steps with methanol and a higher-boiling alcohol at elevated temperatures in the presence of an acidic, preferably heterogeneous catalyst, under as dry as possible conditions.
Inventors
- 👤 Rolf Lebuhn
- 👤 John Feldmann
- 👤 Hubert Koebernick
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 14:14
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/04
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
128 words
A process for producing a color-stable, industrial-grade methyl glucoside which comprises: (a) first heating a mixture of glucose and excess methanol in the presence of an acidic catalyst under conditions which exclude water until the reaction product mixture contains less than about 20% glucose on a dry weight basis; (b) then heating the reaction product mixture with an excess of a higher-boiling alcohol in the presence of an acidic catalyst under conditions for the continuous azeotropic removal of water until the glucose content of the mixture is about 0.3% or less on a dry substance basis, said higher-boiling alcohol being one that boils above 80° C. at atmospheric pressure and forms an azeotrope with water; and (c) separating unreacted higher-boiling alcohol from the mixture obtained in Step (b).
Claim 2
Dependent Claim
128 words
A process for producing a color-stable, industrial-grade methyl glucoside which comprises: (a) first heating a mixture of glucose and excess methanol in the presence of an acidic catalyst under conditions which exclude water until the reaction product mixture contains less than about 20% glucose on a dry weight basis; (b) then heating the reaction product mixture with an excess of a higher-boiling alcohol in the presence of an acidic catalyst under conditions for the continuous azeotropic removal of water until the glucose content of the mixture is about 0.3% or less on a dry substance basis, said higher-boiling alcohol being one that boils above 80° C. at atmospheric pressure and forms an azeotrope with water; and (c) separating unreacted higher-boiling alcohol from the mixture obtained in Step (b).
Claim 3
Dependent Claim
14 words
The process of claim 1 wherein the acidic catalyst is a heterogeneous acidic catalyst.
Claim 4
Dependent Claim
16 words
The process of claim 2 wherein the heterogeneous acidic catalyst is a strongly acidic cation-exchange resin.
Claim 5
Dependent Claim
33 words
The process of claim 3 wherein the strongly acidic cation-exchange resin is selected from the group consisting of: a highly cross-linked macroporous resin, a slightly cross-linked gel resin, and an acidic molecular sieve.
Claim 6
Dependent Claim
15 words
The process of claim 4 wherein the acidic molecular sieve is an inorganic molecular sieve.
Claim 7
Dependent Claim
15 words
The process of claim 2 wherein the heterogeneous acidic catalyst is solid under reaction conditions.
Claim 8
Dependent Claim
21 words
The process of claim 1 wherein the methanol is used at a molar ratio to glucose of from 3:1 to 20:1.
Claim 9
Dependent Claim
24 words
The process of claim 1 wherein, during the reaction with the higher-boiling alcohol, an inert entrainer is used which forms an azeotrope with water.
Claim 10
Dependent Claim
21 words
The process of claim 1 wherein the higher-boiling alcohol is selected from the group consisting of: propanol, ethylene glycol, and butanol.
Claim 11
Dependent Claim
27 words
The process of claim 1 wherein the unreacted methanol and water is removed from the reaction product mixture of Step (a) before Step (b) is carried out.
Claim 12
Dependent Claim
26 words
The process of claim 1 wherein a water-absorbing agent, which is practically insoluble in the reaction mixture, is used in the reaction between glucose and methanol.
Claim 13
Dependent Claim
39 words
The process of claim 11 wherein the water-absorbing agent is added to the reaction mixture in the final phase of Step (a) when a methyl glucoside content of at least 65%, on a dry weight basis, has been reached.
Claim 14
Dependent Claim
39 words
The process of claim 12 wherein the water-absorbing agent is added to the reaction mixture in the final phase of Step (a) when a methyl glucoside content of at least 75%, on a dry weight basis, has been reached.
Claim 15
Dependent Claim
39 words
The process of claim 12 wherein the water-adsorbing agent is added to the reaction mixture in the final phase of Step (a) when a methyl glucoside content of at least 80%, on a dry weight basis, has been reached.
Claim 16
Dependent Claim
132 words
A process for producing a color-stable, industrial-grade methyl glucoside which comprises: (a) heating a mixture of glucose and excess of a higher-boiling alcohol in the presence of an acidic catalyst under conditions for the continuous azeotropic removal of water until the glucose content of the reaction product mixture measured as a D.E. value is below about 0.2% on a dry weight basis, said higher-boiling alcohol being one that boils above 80° C. at atmospheric pressure and forms an azeotrope with water; (b) separating unreacted alcohol from the reaction product mixture of Step (a); and (c) reacting the mixture obtained in Step (b) with an excess of methanol in the presence of an acidic catalyst until the methyl glucoside content of the resulting product is at least 60% on a dry weight basis.
Claim 17
Dependent Claim
132 words
A process for producing a color-stable, industrial-grade methyl glucoside which comprises: (a) heating a mixture of glucose and excess of a higher-boiling alcohol in the presence of an acidic catalyst under conditions for the continuous azeotropic removal of water until the glucose content of the reaction product mixture measured as a D.E. value is below about 0.2% on a dry weight basis, said higher-boiling alcohol being one that boils above 80° C. at atmospheric pressure and forms an azeotrope with water; (b) separating unreacted alcohol from the reaction product mixture of Step (a); and (c) reacting the mixture obtained in Step (b) with an excess of methanol in the presence of an acidic catalyst until the methyl glucoside content of the resulting product is at least 60% on a dry weight basis.
Claim 18
Dependent Claim
14 words
The process of claim 15 wherein the acidic catalyst is a heterogeneous acidic catalyst.
Claim 19
Dependent Claim
16 words
The process of claim 16 wherein the heterogeneous acidic catalyst is a strongly acidic cation-exchange resin.
Claim 20
Dependent Claim
33 words
The process of claim 17 wherein the strongly acidic cation-exchange resin is selected from the group consisting of: a highly cross-linked macroporous resin, a slightly cross-linked gel resin, and an acidic molecular sieve.
Claim 21
Dependent Claim
15 words
The process of claim 18 wherein the acidic molecular sieve is an inorganic molecular sieve.
Claim 22
Dependent Claim
15 words
The process of claim 16 wherein the heterogeneous acidic catalyst is solid under reaction conditions.
Claim 23
Dependent Claim
24 words
The process of claim 15 wherein, during the reaction with the higher-boiling alcohol, an inert entrainer is used which forms an azeotrope with water.
Claim 24
Dependent Claim
21 words
The process of claim 15 wherein the higher-boiling alcohol is selected from the group consisting of: propanol, ethylene glycol, and butanol.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-01-10 | 1992-07-11 | 1993-01-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-01-10 | 1996-07-11 | 1997-01-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-01-10 | 2000-07-11 | 2001-01-10 | $7700.00 | Window Closed / Lapsed |