EP0341063A2
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EP
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Process for preparing 5-C-hydroxymethyl aldohexose-based compounds
Assignee: Procter and Gamble Co
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Filing: 1989-05-04
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Granted: —
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Expires: 2009-05-04
Abstract
Abstract Processes of the present invention provide economical methods for preparing derivatives 5-C-hydroxymethyl-D-aldohexose and their bicyclic anhydro tautomeric forms. The 5-C-hydroxymethylation process comprises an enzymic oxidation reaction followed by a condensation reaction with formaldehyde.
Inventors
- 👤 Adam Wieslaw Mazur
- 👤 George Douglas Ii Hiler
- 👤 Gordon Keith Stipp
- 👤 Bernard William Kluesener
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 22:25
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/04; C07H19/00; C07H19/01; C12; C12P; C12P19/00; C12P19/02; C12P19/44
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
162 words
A method of preparing 5-C-hydroxymethyl derivatives of D-galactose based compounds comprising the steps of: (a) reacting under agitation an aqueous solution, preferably having a pH of from 6 to 8 and a temperature of from 1 o C to about 50 o C, comprising: (i) from 1% to 50% D-aldohexose-based compound or a mixture of D-aldohexose-based compounds, and (ii) from 1,000 to 1,000,000 unit activity of the enzyme D-aldohexose:oxygen 6-oxidoreductase per mole of D-aldohexose-based compound preferably, wherein galactose oxidase is the enzyme; (b) reacting the solution produced by step (a) with from 1 to 40 molar equivalents of formaldehyde and from 1 to 13 molar equivalents of a base selected from the group consisting of sodium hydroxide, calcium hydroxide, and potassium hydroxide and mixtures thereof, at a temperature of from 15 o C to 40 o C and a pH of from 12 to 13; and (c) purifying the resulting aqueous 5-C-hydroxymethyl-D-aldohexose-based compound-containing solution, preferably by dewatering and then crystallizing the compound.
Claim 2
Independent Claim
162 words
A method of preparing 5-C-hydroxymethyl derivatives of D-galactose based compounds comprising the steps of: (a) reacting under agitation an aqueous solution, preferably having a pH of from 6 to 8 and a temperature of from 1 o C to about 50 o C, comprising: (i) from 1% to 50% D-aldohexose-based compound or a mixture of D-aldohexose-based compounds, and (ii) from 1,000 to 1,000,000 unit activity of the enzyme D-aldohexose:oxygen 6-oxidoreductase per mole of D-aldohexose-based compound preferably, wherein galactose oxidase is the enzyme; (b) reacting the solution produced by step (a) with from 1 to 40 molar equivalents of formaldehyde and from 1 to 13 molar equivalents of a base selected from the group consisting of sodium hydroxide, calcium hydroxide, and potassium hydroxide and mixtures thereof, at a temperature of from 15 o C to 40 o C and a pH of from 12 to 13; and (c) purifying the resulting aqueous 5-C-hydroxymethyl-D-aldohexose-based compound-containing solution, preferably by dewatering and then crystallizing the compound.
Claim 3
Dependent Claim
28 words
A method according to Claim 1 wherein the reaction solution of step (a) further comprises from 10,000 to 2,000,000 unit activity of catalase per mole of D-aldohexose-based compound.
Claim 4
Dependent Claim
37 words
A method according to Claim 1 or 2 wherein the enzyme used in step (a) is removed prior to step (b) by ultrafiltration using a membrane having a molecular weight cut off of from 1,000 to 30,000.
Claim 5
Dependent Claim
15 words
A method according to Claim 1, 2, or 3 wherein said galactose oxidase is immobilized.
Claim 6
Dependent Claim
53 words
A method according to Claim 1 to 4 wherein said reaction temperature of step (a) is from 3 o C to 25 o C and wherein the aqueous solution of step (a) comprises from 10% to 20% of a D-aldohexose-based compound which is a D-galactose based compound and is conducted under sterile conditions.
Claim 7
Dependent Claim
33 words
A method according to Claim 1-5 wherein the reaction solution of step (a) further comprises from 0.1 mM to 2 mM of copper cation or from 0.1 to 1 g/L of serum albumin.
Claim 8
Independent Claim
82 words
A method according to Claims 1 to 5 wherein step (a) is conducted in an oxygen saturated solution, preferably wherein the mixture is mixed at a tip speed of 100 to 400 feet/minute (30 m/min. to 120 m/min.) and contacted with 2 to 3 volumes of air per volume of reactant and wherein, in step (b), the formaldehyde and the base are prereacted at a temperature of from 0°C to about 35°C prior to combination with the solution produced by step (a).
Claim 9
Dependent Claim
48 words
A method according to Claim 1 to 7 wherein step (c) comprises: (i) deionizing the solution using a process selected from the group consisting of adsorption, dialysis, precipitation, and combinations of two or more such processes; (ii)removing excess formaldehyde by adsorption or by fractional distillation followed by absorption.
Claim 10
Dependent Claim
98 words
A method according to Claim 1 to 8 comprising the additional steps of: (d) hydrolyzing the condensation product of step (c) with from about 1 to about 10 molar equivalents of an acid selected from the group consisting of sulfuric acid, nitric acid, hydrochloric acid, perchloric acid, phosphoric acid, methanesulfonic acid, trifluoromethane sulfonic acid, and mixtures thereof, wherein the temperature of the reaction mixture is maintained at from about 20°C to about boiling; preferably from 80 o C to 100 o C, and (e) removing any residual acid from the reaction mixture. preferably by neutralization followed by precipitation.
Claim 11
Independent Claim
89 words
A method of preparing 5-C-hydroxymethyl derivatives of D-galactose based compounds according to Claims 1 to 9 wherein step (b) is conducted as follows: (b) reacting the solution produced by step (a) with from about 1 to about 40 molar equivalents of formaldehyde in the presence of a resin containing hydroxide ions at a pH of at least 11.5 and at a temperature of from 20 o C to 50 o C and (c) purifying the resulting aqueous 5-C-hydroxymethyl-D-aldohexose-based compound-containing solution, preferably by dewatering and crystallizing the compound from methanol.
References Cited (Backward Citations)
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