US4713447A
Expired / Lapsed
US
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Process for preparing alkyl glycosides
Assignee: Procter and Gamble Co
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Filing: 1983-09-28
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Granted: 1987-12-15
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Expires: 2003-09-28
Abstract
Abstract Improvement in the acid catalyzed process for preparing alkyl glycosides by reaction of an alcohol with a monosaccharide or source of monosaccharide moiety, the improvement residing in the use of certain organic bases to neutralize the catalyst at the end of the reaction.
Inventors
- 👤 James C. Letton
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 15:49
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/04
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
158 words
An improved process for preparing alkyl glycosides having from about 1 to about 30 carbon atoms in the alkyl chain, comprising the steps of: (a) reacting a C 1 to C 30 monohydric alcohol with a source of reducing monosaccharide moiety, selected from the group consisting of reducing monosaccharides, corn syrup, molasses and the glycosides of C 1 to C 4 alcohols, in the presence of an acid catalyst; and (b) neutralizing the catalyst with a base to a pH of from about 6.6 to about 7; the improvement comprising neutralizing the catalyst with an organic base of the formula (RO) n M, wherein R is a substituted or unsubstituted alkyl or acyl of from 1 to about 30 carbon atoms, M is selected from the group consisting of alkali metal, alkaline earth metal and aluminum and n is 1 when M is alkali metal, 2 when M is alkaline earth metal, and 3 when M is aluminum.
Claim 2
Dependent Claim
158 words
An improved process for preparing alkyl glycosides having from about 1 to about 30 carbon atoms in the alkyl chain, comprising the steps of: (a) reacting a C 1 to C 30 monohydric alcohol with a source of reducing monosaccharide moiety, selected from the group consisting of reducing monosaccharides, corn syrup, molasses and the glycosides of C 1 to C 4 alcohols, in the presence of an acid catalyst; and (b) neutralizing the catalyst with a base to a pH of from about 6.6 to about 7; the improvement comprising neutralizing the catalyst with an organic base of the formula (RO) n M, wherein R is a substituted or unsubstituted alkyl or acyl of from 1 to about 30 carbon atoms, M is selected from the group consisting of alkali metal, alkaline earth metal and aluminum and n is 1 when M is alkali metal, 2 when M is alkaline earth metal, and 3 when M is aluminum.
Claim 3
Dependent Claim
27 words
The process of claim 1 wherein the R in the organic base is an unsubstituted alkyl or acyl radical of from 1 to about 4 carbon atoms.
Claim 4
Dependent Claim
17 words
The process of claim 2 wherein the monohydric alcohol contains from 8 to about 30 carbon atoms.
Claim 5
Dependent Claim
15 words
The process of claim 3 wherein the source of reducing monosaccharide moiety is a monosaccharide.
Claim 6
Dependent Claim
38 words
The process of claim 4 wherein the acid catalyst is selected from the group consisting of sulfuric acid, hydrochloric acid, phosphoric acid, phosphorous acid, p-toluene sulfonic acid, boron trifluoride, sulfonic acid ion exchange resins, and unneutralized anionic surfactants.
Claim 7
Dependent Claim
28 words
The process of claims 1, 2, 3 through 5 wherein R in the organic base is an unsubstituted alkyl radical of from 1 to about 4 carbon atoms.
Claim 8
Dependent Claim
92 words
The process of claim 6 wherein the acid catalyst is selected from the group consisting of: (a) Alkyl sulfates of the formula RO(C.sub.2 H.sub.4 O).sub.n SO.sub.3 H wherein R is an alkyl group of from about 8 to about 22 carbon atoms, and n is from 0 to about 6, (b) Alkylbenzene sulfonates of the formula ##STR2## wherein R is alkyl of from about 8 to about 15 carbon atoms, and (c) Alkyl sulfonates of the formula RSO.sub.3 H wherein R is alkyl of from about 8 to about 22 carbon atoms.
Claim 9
Dependent Claim
32 words
The process of claim 7 wherein the acid catalyst is an alkylbenzene sulfonic acid having from 12 to 14 carbon atoms in the alkyl chain and the neutralizing base is sodium ethoxide.
Claim 10
Dependent Claim
27 words
The process of claims 1, 2, 3 through 5 wherein R in the neutralizing base is an acyl radical of from 1 to about 4 carbon atoms.
Claim 11
Dependent Claim
92 words
The process of claim 9 wherein the acid catalyst is selected from the group consisting of: (a) Alkyl sulfates of the formula RO(C.sub.2 H.sub.4 O).sub.n SO.sub.3 H wherein R is an alkyl group of from about 8 to about 22 carbon atoms, and n is from 0 to about 6, (b) Alkylbenzene sulfonates of the formula ##STR3## wherein R is alkyl of from about 8 to about 15 carbon atoms, and (c) Alkyl sulfonates of the formula RSO.sub.3 H wherein R is alkyl of from about 8 to about 22 carbon atoms.
Claim 12
Dependent Claim
12 words
The process of claim 10 wherein the neutralizing base is sodium acetate.
Claim 13
Dependent Claim
13 words
The process of claim 4 wherein the source of reducing monosaccharide is glucose.
Claim 14
Dependent Claim
14 words
The process of claim 4 wherein the source of reducing monosaccharide is corn syrup.
References Cited (Backward Citations)
US3839318A
Cited
EP0132043A1
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-12-14 | 1991-06-15 | 1991-12-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-12-14 | 1995-06-15 | 1995-12-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-12-14 | 1999-06-15 | 1999-12-15 | $7700.00 | Window Closed / Lapsed |