Process for preparing APG's
First Claim
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1. A process for preparing an alkylpolyglycoside of the formula (I);
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space="preserve" listing-type="equation">H--(G).sub.n --OR (I)wherein R is a linear or branched, saturated or unsaturated alkyl radical having from 8 to 20 carbon atoms;
G is a pyranoside or furanoside;
n is an integer from 1 to 5;
said process comprising reacting an alcohol with a monosaccharide, an alkylglycoside, or a compound capable of generating in situ a monosaccharide, in the presence of a sulfonic acid catalyst, wherein the molar ratio of sulfonic acid catalyst and monosaccharide is 0.001 to 0.1 and the molar ratio alcohol to monosaccharide is 1.5 to 3.3;
wherein said sulfonic acid catalyst is of the formula (II);
##STR3## wherein R1 and R2, the same or different can be;
an alkyl radical having from 1 to 4 carbon atoms;
a halogen selected from the group consisting of Cl, Br and I;
a residue selected from the group consisting of --OR6, --SR7, --COOR8 moieties, wherein R6, R7 and R8 are alkyl residues having from 1 to 4 carbon atoms;
end in which R3, R4 and R5, the same or different, can be hydrogen or any of the meanings as defined above for R1 and R2 ;
or said sulfonic acid catalyst is of the formula (III);
##STR4## wherein R9, R10, R11 and R13, the same or different, can bean alkyl radical having from 1 to 4 carbon atoms;
a halogen selected from the group consisting of Cl, Br and I;
a residue selected from the group consisting of --OR6, --SR7, --COOR8 moieties, wherein R6, R7 and R8 are alkyl residues having from 1 to 4 carbon atoms;
and, optionally, R11 and R12 form, when taken together, a substituted or unsubstituted alkylenic residue having from 2 to 4 carbons.
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Abstract
An improved method for synthesizing alkylpolyglucosides comprising reacting a glycoside with a long-chain alcohol in the presence of a novel type of catalyst, constituted by an alkali or aryl sulfonic acid, wherein the sulfonic group is sterically hindered. Using these catalysts, a raw product is obtained which is practically free from byproducts. The resulting alkyl polyglucosides are completely biodegradable surfactants and can be used to formulate detergents.
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12 Claims
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1. A process for preparing an alkylpolyglycoside of the formula (I);
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space="preserve" listing-type="equation">H--(G).sub.n --OR (I)wherein R is a linear or branched, saturated or unsaturated alkyl radical having from 8 to 20 carbon atoms; G is a pyranoside or furanoside; n is an integer from 1 to 5; said process comprising reacting an alcohol with a monosaccharide, an alkylglycoside, or a compound capable of generating in situ a monosaccharide, in the presence of a sulfonic acid catalyst, wherein the molar ratio of sulfonic acid catalyst and monosaccharide is 0.001 to 0.1 and the molar ratio alcohol to monosaccharide is 1.5 to 3.3; wherein said sulfonic acid catalyst is of the formula (II);
##STR3## wherein R1 and R2, the same or different can be;
an alkyl radical having from 1 to 4 carbon atoms;a halogen selected from the group consisting of Cl, Br and I; a residue selected from the group consisting of --OR6, --SR7, --COOR8 moieties, wherein R6, R7 and R8 are alkyl residues having from 1 to 4 carbon atoms; end in which R3, R4 and R5, the same or different, can be hydrogen or any of the meanings as defined above for R1 and R2 ; or said sulfonic acid catalyst is of the formula (III);
##STR4## wherein R9, R10, R11 and R13, the same or different, can bean alkyl radical having from 1 to 4 carbon atoms; a halogen selected from the group consisting of Cl, Br and I; a residue selected from the group consisting of --OR6, --SR7, --COOR8 moieties, wherein R6, R7 and R8 are alkyl residues having from 1 to 4 carbon atoms; and, optionally, R11 and R12 form, when taken together, a substituted or unsubstituted alkylenic residue having from 2 to 4 carbons. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12)
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Current AssigneeEniChem S.p.A., Eniricerche S.P.A.
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Original AssigneeEniChem S.p.A., Eniricerche S.P.A.
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InventorsPellizzon, Tullio, Borsotti, Giampiero
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Primary Examiner(s)Robinson, Douglas W.
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Assistant Examiner(s)Lee, Howard C.
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Application NumberUS08/213,702Time in Patent Office825 DaysField of Search536/18.6, 536/124, 536/126, 536/127, 424/70, 252/174.17, 252/DIG. 5, 252/DIG. 13, 252/DIG. 14US Class Current536/18.6CPC Class CodesC07H 15/04 attached to an oxygen atom ...
