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US5138046A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing alkylglucoside compounds from oligo- and/or polysaccharides

Assignee: Henkel AG and Co KGaA
•
Filing: 1989-08-04
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Granted: 1992-08-11
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Expires: 2009-08-04
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Abstract

Abstract Surface active alkylglucosides are prepared in a 2-step process from starch or starch degradation products such as polyglucose or glucose syrup, the first step consisting of reaction with a short chained alcohol, particularly butanol, while the second step comprises transacetalization with the longer chained C 8-22 , more particularly C 12-18 , alcohol, with fatty alcohols of natural origin preferably being used.

Inventors

  • 👤 Willi Wuest
  • 👤 Rainer Eskuchen
  • 👤 Josef Wollman
  • 👤 Karlheinz Hill
  • 👤 Manfred Biermann

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 01:03
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/04; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/582

Claims Analysis

Total Claims: 26
Claim 1
Independent Claim 249 words
A process for preparing a reaction product containing surface active alkylglucoside compounds comprising a predominate content of alkyl monoglucoside from long chain monohydroxyl alcohols and a saccharide source selected from the group consisting of starch, polysaccharides other than starch, starch partial degradation products, and oligosaccharides other than starch partial degradation products, comprising formation of lower alkyl glucosides and transacetalization thereof with long chain monohydroxyl alcohols, which process comprises: a) reacting the saccharide source under acidic catalysis with a sufficient amount of a mixture of water and lower alkanol, which mixture is in a single phase at the reaction conditions of a temperature above 100° C. and elevated pressure, to provide throughout the entire reaction a stoichiomeric excess of lower alkanol and a stirable and flowable reaction mixture and continuing the reaction until a liquid, virtually clear single-phase first reaction product is obtained; b) admixing and reacting the first reaction product with a stoichiometric excess of the long chain alcohol heated to a reaction temperature above about 100° C., to form a second reaction mixture which is a single-phase at the operating temperature of the second reaction mixture throughout the entire reaction, under reaction conditions of pressure, temperature and rate of admixing that the water in the first reaction product is vaporized virtually immediately as it is admixed with the second reaction mixture; and c) evaporating the lower alkanol present in the first reaction product and formed by transacetalization to form a reaction product containing the surface active alkylglucoside compounds.
Claim 2
Dependent Claim 249 words
A process for preparing a reaction product containing surface active alkylglucoside compounds comprising a predominate content of alkyl monoglucoside from long chain monohydroxyl alcohols and a saccharide source selected from the group consisting of starch, polysaccharides other than starch, starch partial degradation products, and oligosaccharides other than starch partial degradation products, comprising formation of lower alkyl glucosides and transacetalization thereof with long chain monohydroxyl alcohols, which process comprises: a) reacting the saccharide source under acidic catalysis with a sufficient amount of a mixture of water and lower alkanol, which mixture is in a single phase at the reaction conditions of a temperature above 100° C. and elevated pressure, to provide throughout the entire reaction a stoichiomeric excess of lower alkanol and a stirable and flowable reaction mixture and continuing the reaction until a liquid, virtually clear single-phase first reaction product is obtained; b) admixing and reacting the first reaction product with a stoichiometric excess of the long chain alcohol heated to a reaction temperature above about 100° C., to form a second reaction mixture which is a single-phase at the operating temperature of the second reaction mixture throughout the entire reaction, under reaction conditions of pressure, temperature and rate of admixing that the water in the first reaction product is vaporized virtually immediately as it is admixed with the second reaction mixture; and c) evaporating the lower alkanol present in the first reaction product and formed by transacetalization to form a reaction product containing the surface active alkylglucoside compounds.
Claim 3
Dependent Claim 41 words
A process of claim 1, wherein the temperature of the second reaction mixture is maintained by indirect heat transfer with a heating medium at a temperature difference ΔT not greater than 30° C., wherein ΔT=T heating medium -T second reaction mixture.
Claim 4
Dependent Claim 41 words
A process of claim 1, wherein at least a major portion of the heat energy required in the second reaction mixture is supplied by indirect heat transfer of a stream of the second reaction mixture circulated outside a main reaction zone.
Claim 5
Dependent Claim 30 words
A process of claim 1, wherein the first reaction mixture is heated by indirect heat transfer of a stream of the first reaction mixture outside of a main reaction zone.
Claim 6
Dependent Claim 15 words
A process of claim 1, wherein the lower alkanol comprises a C 3-5 monohydroxyl alcohol.
Claim 7
Dependent Claim 27 words
A process of claim 1, wherein the saccharide source comprises at least one member selected from the group consisting of powdered native starch, polyglucose and glucose syrup.
Claim 8
Dependent Claim 32 words
A process of claim 1, wherein step a) is carried out at a temperature above 125° C. and under a pressure of about 4 to 10 bar in a closed reaction zone.
Claim 9
Dependent Claim 26 words
A process of claim 1, wherein the second reaction step b) is carried out at temperatures below the temperature of reaction step a) under reduced pressure.
Claim 10
Dependent Claim 14 words
A process of claim 1, wherein transacetalization is carried out under an increasing vacuum.
Claim 11
Dependent Claim 19 words
A process of claim 1, wherein a further amount of acid catalyst is added to the second reaction mixture.
Claim 12
Dependent Claim 19 words
A process of claim 1, wherein the single phase mixture comprises water and butanol is substantially equal molar amounts.
Claim 13
Dependent Claim 26 words
A process of claim 1, wherein in step a) the molar ratio of saccharide source to water is in the range from about 1:5 to 1:12.
Claim 14
Dependent Claim 29 words
A process of claim 1, wherein in the second reaction mixture the molar ratio of starch, calculated as anhydroglucose, to the long chain alcohol ranges from 1:1.5 to 1:7.
Claim 15
Dependent Claim 75 words
A process of claim 1, wherein at the end of the reaction the acid catalyst is neutralized by addition of at least one basic compound selected from the group consisting of basic organic alkali metal compounds, basic organic alkaline earth metal compounds, basic organic aluminum compounds, basic inorganic alkali metal compounds, basic inorganic alkaline earth metal compounds and basic inorganic aluminum compounds to the second reaction mixture to a pH value of at least 8.
Claim 16
Dependent Claim 14 words
A process of claim 14, wherein the neutralized second reaction product is oxidatively bleached.
Claim 17
Dependent Claim 28 words
A process of claim 1, wherein the long chain monohydroxyl alcohol comprises compounds of natural or synthetic organic with chain lengths in the range from C 12-18 .
Claim 18
Dependent Claim 13 words
A process of claim 2, wherein ΔT is not larger than 20° C..
Claim 19
Dependent Claim 11 words
A process of claim 5, wherein the monohydroxyl alkanol is n-butanol.
Claim 20
Dependent Claim 17 words
A process of claim 8, wherein the temperature is in the range of from 110° to 120°.
Claim 21
Dependent Claim 14 words
A process of claim 9, wherein the final pressure is about 10 m bar.
Claim 22
Dependent Claim 12 words
A process of claim 10, wherein the catalyst is a sulphonic acid.
Claim 23
Dependent Claim 24 words
A process of claim 13, wherein the molar ratio of starch, calculated as anhydroglucose, to the long chain alcohol is from 1:2.5 to 1:7.
Claim 24
Dependent Claim 24 words
A process of claim 21, wherein the molar ratio of starch, calculated as anhydroglucose, to the long chain alcohol is from 1:3 to 1:5.
Claim 25
Dependent Claim 17 words
A process of claim 15, wherein the neutralized second reaction product is oxidatively bleached with hydrogen peroxide.
Claim 26
Dependent Claim 29 words
A process of claim 15, wherein the neutralized second reaction mixture is oxidatively bleached with at least one member selected from the group consisting of peracids and peracid salts.

References Cited (Backward Citations)

US2390507A Cited
US3219656A Cited
FR2017240A1 Cited
EP0035589A1 Cited
EP0099183A1 Cited
US4721780A Cited
US4889925A Cited
US4990605A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1995-08-11 1996-02-10 1996-08-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1999-08-11 2000-02-10 2000-08-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2003-08-11 2004-02-10 2004-08-11 $7700.00 Window Closed / Lapsed

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