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Method for preparing glucuronic acid and lactone thereof by heterogenous catalytic oxidation

A technology of glucuronic acid and heterogeneous catalysis, which is applied in the field of catalyzing the oxidation of megluside to prepare glucuronic acid and its lactone, achieving the effects of saving resources, overcoming the production process, and simple operation

Inactive Publication Date: 2009-07-15
WUHAN INSTITUTE OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved by the present invention is to provide a method for preparing glucuronic acid or its lactone by a heterogeneous catalytic oxidation method for the deficiencies in the process of producing glucuronolactone by the traditional nitric acid oxidation method; the method prepares glucose Aldehydic acid or its lactone has high selectivity, less environmental pollution, and the catalyst is easy to separate

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  • Method for preparing glucuronic acid and lactone thereof by heterogenous catalytic oxidation
  • Method for preparing glucuronic acid and lactone thereof by heterogenous catalytic oxidation
  • Method for preparing glucuronic acid and lactone thereof by heterogenous catalytic oxidation

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preparation example Construction

[0017] The preparation method of the catalyst carrier used in the present invention is the citric acid complex method, promptly weighs the metal salt of the required metal component and citric acid according to the composition ratio of the carrier (the total molar ratio of citric acid and the metal ion used is 3:1) , add water to dissolve, mix, evaporate, and roast to obtain; the preparation method of the catalyst is the precipitation method, that is, the carrier obtained above is soaked in the active component solution, and the precipitant NaOH solution or ammonia water is added dropwise to deposit the active component on the carrier. , and then filtered, washed, dried and calcined to obtain the required catalyst. The preparation method of the above-mentioned carrier and catalyst can be carried out with reference to [Acta Catalytica Sinica 2002, 23(5): 413-416].

[0018] Weigh 6.0g of methyl glucoside (99.5%, industrial grade) into a reaction flask, add 50mL of distilled wate...

Embodiment 1

[0021] Weigh 6.0g of methyl glucoside into a three-necked flask, add 50mL of distilled water, dissolve and add 1.0g of Pd / La 0.5 Pb 0.5 MnO 3 Catalyst (the catalyst can be prepared according to the literature [Acta Catalytica Sinica 2002, 23(5): 413-416]), mechanically stirred and introduced with air. The reaction conditions are normal pressure and the temperature is 75°C. The pH value of the reaction mixture is maintained at 8-10 by dropping 1mol / L NaOH solution, and the pH value of the reaction solution is monitored with a pHs-25 digital display pH meter. After 4 hours Stop the reaction, filter the reaction mixture, adjust the pH value of the filtrate to 1-2 with dilute hydrochloric acid, and carry out hydrolysis reaction at 90°C for 3 hours. Leave standstill to cool down, take a sample and analyze the content of glucuronic acid and lactone with high performance liquid chromatography, glucuronic acid (retention time 2.809min) content reaches 29.5%, glucuronolactone (retent...

Embodiment 2

[0023] Take 6.0g methyl glucoside (99.5%, technical grade) in reaction bottle, add 50mL distilled water, add 1.0g Pd / La after dissolving 0.5 Pb 0.5 mn 0.9 sn 0.1 o 3 Catalyst (the catalyst can be prepared according to the literature [Acta Catalytica Sinica 2002, 23(5): 413-416]), mechanically stirred and introduced with air. Raise the temperature to 70°C, add 1mol / L NaOH solution dropwise to maintain the pH of the reaction mixture at 8-10, monitor the pH of the reaction solution with a pHS-25 digital display pH meter, and stop the reaction after about 5 hours. After filtering, the filtrate was adjusted to pH 1-3 with dilute hydrochloric acid, and hydrolyzed at 90°C for 3 hours. The content of glucuronic acid in the reaction process was monitored by the m-hydroxybiphenyl method. Leave it to cool, and take a sample to analyze the content of glucuronic acid and lactone by high performance liquid chromatography. The reaction result is that the content of glucuronic acid is 32....

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Abstract

The invention discloses a method for preparing glucuronic acid and lactone thereof by heterogeneous catalytic oxidation of methyl gluoside. The method comprises the following steps: taking a supported palladium / perovskite composite metal oxide as a catalyst, employing dioxygen to perform selective catalytic oxidation for 2-5h on primary hydroxyl of the methyl glucoside, controlling the pH value at 8-11 and the reaction temperature at 60-90 DEG C during the catalytic oxidation, then filtering to separate the catalyst, allowing the filtrate to a hydrolysis reaction for 1-3h with the pH value controlled at 1-3 and the reaction temperature at 60-90 DEG C to obtain the glucuronic acid, and under the condition, the glucuronic acid is partially converted to generate the glucuronic acid lactone. The method has high selectivity and little environmental pollution, helps easily separate the catalyst and meets the development requirements of green chemistry. In the method, the dioxygen is adopted for the selective catalytic oxidation at the normal pressure, which has no special requirements for equipment, ensures simple operation and can realize clean production. A reproducible glucose derivative is taken as a raw material, which ensures a high utilization rate of the raw materials, thus saving resources and lowering the production cost.

Description

technical field [0001] The invention relates to a method for preparing glucuronic acid and its lactone by catalytically oxidizing megluside. Background technique [0002] Glucuronolactone, referred to as glucuronolactone, the molecular formula is C 6 h 8 o 6 , whose chemical composition is D(+)-glucofuranurono-γ-lactone [D(+)-Glucofuranurono-6,3-lactone]. As a liver detoxifier and immune function regulator, glucuronolactone is a conventional liver-protecting medicine. Its mechanism of action is that the lactone is catalyzed by the enzyme into glucuronic acid, and glucuronic acid can combine with hydroxyl, Toxic substances such as carboxyl and mercapto groups combine to form glucuronic acid conjugates and are excreted in urine to protect the liver and detoxify. Additives have the functions of replenishing physical fitness, improving hypoxia, nourishing skin, and delaying aging. The market demand for them has exceeded that in the pharmaceutical field in recent years. [0...

Claims

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Application Information

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IPC IPC(8): C07H7/033C07D493/04C07H1/00
Inventor 袁华吴元欣陈启明孙炎彬邬茂熊小焱
Owner WUHAN INSTITUTE OF TECHNOLOGY
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