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Methods for the electrolytic production of erythrose or erythritol

A technology of erythritol and erythritol, which is applied in electrolytic organic production, electrolytic components, electrolytic process, etc., can solve problems such as foaming, expensive erythritol, and the amount of by-products

Active Publication Date: 2008-12-31
DFI USA LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Possible disadvantages of producing erythritol by fermentation include foaming during fermentation, undesirably low fermentation rate, amount of by-products ...

Method used

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  • Methods for the electrolytic production of erythrose or erythritol
  • Methods for the electrolytic production of erythrose or erythritol
  • Methods for the electrolytic production of erythrose or erythritol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Example 1: Electrolytic Decarboxylation of Ribose Acid

[0069] Sodium ribonate (15 mmol) was dissolved in 20 mL of water. Addition of cation exchange resin (Amberlite IRC747 H+ form) lowered the pH from 6.8 to 3.5 (or neutralized about 50% of the feedstock). The above solution was filtered to remove the cation resin, the ribose salt raw material was diluted to 30 mL, and 25 mL was transferred to a glass cell for electrolysis. The initial ribonate solution was analyzed by HPLC against standards and quantified at 9.54 millimolar (0.38M). Stir 25 mL of stock containing 9.54 mmol of ribonate in a glass cell while applying 0.5 A (100 mA / cm 2 ) constant current. The cell voltage averaged about 6.5 volts, and the pH of the substrate increased from 3.5 to 7.6 after a charge of 2 F / mole had passed. Samples were taken at 603, 1206 and 1809 coulombs. Samples containing erythritol product were reduced to erythritol using excess sodium borohydride, and HPLC-RI was used to ...

Embodiment 2

[0072] Example 2: Electrolytic Decarboxylation of Arabinonic Acid

[0073] Potassium arabinonate (15 mmol) was dissolved in 20 mL of water. Arabinonic acid was acidified to approximately 50% neutralization by adding cation exchange resin (Amberlite IRC747 H+ form) and lowering the pH from 8.4 to 3.5. The arabinonic acid salt was filtered to remove the resin, diluted to 30 mL, and transferred to a glass cell for electrolysis. Initial arabinonate was quantified by HPLC-RI relative to arabinonate standards and found to contain 9.2 millimolar (0.37M). There was a loss of 3.3 mmoles of arabinate to the cation exchange resin.

[0074] Stir 25 mL of stock containing 9.2 mmol arabinate in a glass cell while applying 0.5 amps (100 mA / cm 2 ) constant current. The cell voltage averaged about 5.5 volts, and the pH of the substrate increased from 3.5 to 7.7 after passing a 2F charge per mole of feedstock. Samples were taken at 603, 1206 and 1809 coulombs. Samples containing erythro...

Embodiment 2-5

[0081] Theoretical Examples 2-5: Oxidative decarboxylation and hydrogenation of glucose to arabitol

[0082] Elseviers et al. in U.S. Patent 5,831,078 filed July 23, 1997 and issued November 3, 1998 for the oxidative decarboxylation of glucose feedstock to arabinonate and the conversion of arabinonate to arabinitol Other suitable examples of are provided below as Theoretical Examples 2-5.

[0083] Theoretical Example 2: Oxidative Decarboxylation Using Oxygen at a Pressure of 2 Bars

[0084] Under stirring at 1000 rpm, the glucose solution (1.5 kg-10% w / w solution) feedstock was heated to 45° C. in a two-liter autoclave. The reactor containing the glucose solution was purged with oxygen twice for 0.5 min at a pressure of 1 bar. After purging, the oxygen pressure in the reactor was adjusted to 2 bar. The reaction was started by dosing potassium hydroxide solution (242 g - 50% w / w solution) to the glucose solution using a dosing burette at a dosing rate of 1.3 moles KOH / ...

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Abstract

The invention provides methods for the production of erythrose and/or erythritol. Preferably, the methods include the step of electrolytic decarboxylation of a ribonic acid or arabinonic acid reactant to produce erythrose. Optionally, the reactant can be obtained from a suitable hexose sugar, such as allose, altrose, glucose, fructose or mannose. The erythrose product can be hydrogenated to produce erythritol.

Description

technical field [0001] The present invention relates to a method for producing erythrose and / or erythritol. Background technique [0002] Erythritol is a naturally occurring polyol sweetener that can be used in place of sugar while maintaining sweetness. Erythritol is a four-carbon sugar polyol (tetraitol) with properties such as sweetness (about 60 to 80% of sucrose), good teeth, very low caloric value (0.2 kcal / g, 5%), is non-carcinogenic, and, unlike other polyols, causes very little, if any, gastrointestinal upset (Harald and Bruxelles (1993) Starch / Starke 45:400-405). In addition, erythritol has desirable processing properties such as thermal stability and minimal undesired reactivity with amino groups to resist browning in the presence of organic matter. Erythritol can be used as a sweetener, for example in beverages. For example, US Patent Nos. 4,902,525 and 6,066,345, JPA 7-274829 and EP 0 759 273 relate to the addition of erythritol to beverages for flavor enhanc...

Claims

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Application Information

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IPC IPC(8): C25B3/02C25B3/23C25B3/25
CPCC07C29/141C07H1/00C07H3/02Y02P20/582C25B3/23C07C31/24C25B11/065C25B15/02
Inventor 乔纳森·A·斯特普利大卫·J·亨德尔斯丹尼尔·M·阿瑟顿彼得·M·肯德尔
Owner DFI USA LLC
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