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US3839318A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparation of alkyl glucosides and alkyl oligosaccharides

Assignee: Rohm and Haas Co
•
Filing: 1970-09-27
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Granted: 1974-10-01
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Expires: 1990-09-27
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Abstract

Abstract A process for the preparation of higher alkyl monosaccharides and oligosaccharides which are surface active. It involves the direct glucosidation of higher alkanols, omitting the double alcohol interchange by careful adjustment of the reaction conditions primarily by limiting the rate of formation of the water of reaction and the rate of oligomerization.

Inventors

  • 👤 R Mansfield

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 23:55
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/04; C11; C11D; C11D1/00; C11D1/66; C11D1/662

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 181 words
IN A PROCESS FOR THE PREPARATION OF A MIXTURE COMPRISED OF HIGH MOLECULAR WEIGHT ALKYL GLUCOSIDES, HIGH MOLECULAR WEIGHT ALKYL OLIGOSACCHARIDES, AND A STARTING HIGHER ALCOHOL, THE IMPROVEMENT CONSISTS ESSENTIALLY OF: A. REACTING A MONOSACCHARIDE SELECTED FROM THE GROUP CONSISTING OF GLYCOSE AND A SOURCE OF GLYCOSE WITH A HIGH MOLECULAR WEIGHT MONOHYDRIC STRAIGHT OR BRANCHED PRIMARY ALCOHOL HAVING FROM 6 TO 18 CARBON ATOMS IN THE PRESENCE OF AN ACID CATALYST WHEREIN SAID CATALYST IS SULFURIC ACID, HYDROCHLORIC ACID, SULFONIC ION EXCHANGE RESINS, OR NITRIC ACID, AT ELEVATED TEMPERATURES RANGING FROM ABOUT 80*C TO ABOUT 130*C; B. REMOVING FROM THE REACTION MIXTURE THE WATER OF REACTION SUBSTANTIALLY AS FAST AS IT IS FORMED BY EITHER VACUUM DISTILLATION OR AXEOTROPIC DISTILLATION; C. CONTROLLING THE CATALYST CONCENTRATION AND TEMPERATURE SO THAT SOLUBILIZATION OF SAID MONOSACCHARIDE AND FORMATION OF THE DESIRED PRODUCTS OCCUR, WHILE OLIGOMERIZATION AND DEGRADATION OF SAID MONOSACCHARIDES IS SUBSTANTIALLY AVOIDED; AND D. EMPLOYING A MOLAR RATIO OF SAID ALCOHOL TO SAID MONOSACCHARIDE SUCH THAT DECREASING GLYCOSE SOLUBILITY WITH RISING ALCOHOL MOLECULAR WEIGHT IS COMPENSATED FOR BY INCREASING SAID MOLAR RATIO.
Claim 2
Dependent Claim 181 words
IN A PROCESS FOR THE PREPARATION OF A MIXTURE COMPRISED OF HIGH MOLECULAR WEIGHT ALKYL GLUCOSIDES, HIGH MOLECULAR WEIGHT ALKYL OLIGOSACCHARIDES, AND A STARTING HIGHER ALCOHOL, THE IMPROVEMENT CONSISTS ESSENTIALLY OF: A. REACTING A MONOSACCHARIDE SELECTED FROM THE GROUP CONSISTING OF GLYCOSE AND A SOURCE OF GLYCOSE WITH A HIGH MOLECULAR WEIGHT MONOHYDRIC STRAIGHT OR BRANCHED PRIMARY ALCOHOL HAVING FROM 6 TO 18 CARBON ATOMS IN THE PRESENCE OF AN ACID CATALYST WHEREIN SAID CATALYST IS SULFURIC ACID, HYDROCHLORIC ACID, SULFONIC ION EXCHANGE RESINS, OR NITRIC ACID, AT ELEVATED TEMPERATURES RANGING FROM ABOUT 80*C TO ABOUT 130*C; B. REMOVING FROM THE REACTION MIXTURE THE WATER OF REACTION SUBSTANTIALLY AS FAST AS IT IS FORMED BY EITHER VACUUM DISTILLATION OR AXEOTROPIC DISTILLATION; C. CONTROLLING THE CATALYST CONCENTRATION AND TEMPERATURE SO THAT SOLUBILIZATION OF SAID MONOSACCHARIDE AND FORMATION OF THE DESIRED PRODUCTS OCCUR, WHILE OLIGOMERIZATION AND DEGRADATION OF SAID MONOSACCHARIDES IS SUBSTANTIALLY AVOIDED; AND D. EMPLOYING A MOLAR RATIO OF SAID ALCOHOL TO SAID MONOSACCHARIDE SUCH THAT DECREASING GLYCOSE SOLUBILITY WITH RISING ALCOHOL MOLECULAR WEIGHT IS COMPENSATED FOR BY INCREASING SAID MOLAR RATIO.
Claim 3
Dependent Claim 13 words
The process as set forth in claim 1 wherein said monosaccharide is glucose.
Claim 4
Dependent Claim 18 words
The process as set forth in claim 1 wherein said alcohol ranges from eight to fourteen carbon atoms.
Claim 5
Dependent Claim 30 words
The process as set forth in claim 1 wherein said molar ratio of alcohol to monosaccharide ranges from 1:1 up to 6:1, provided sufficient solubility of the reaction mixture remains.
Claim 6
Dependent Claim 35 words
The process as set forth in claim 1 wherein the concentration of said acid catalyst ranges from about 0.03 percent to about 10 percent by weight, based on the aldose charge to the reaction vessel.
Claim 7
Dependent Claim 39 words
The process as set forth in claim 1 wherein there is further provision for removing substantially all of said alcohol remaining unreacted after the reaction goes to completion, whereby said product is substantially free of said alcohol starting material.

References Cited (Backward Citations)

US3598865A Cited
US3547828A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1977-09-30 1978-04-01 1978-10-01 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1981-09-30 1982-04-01 1982-10-01 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1985-09-30 1986-04-01 1986-10-01 $7700.00 Window Closed / Lapsed

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