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A kind of method for catalyzing oxidation of pyranoside to synthesize uronic acid

A pyranoside and catalytic oxidation technology, which is applied in chemical instruments and methods, sugar compounds with non-glycosyl groups, organic chemistry, etc., can solve problems such as complex operation, high processing difficulty, human interference, etc., to simplify the reaction process, The effect of improving reaction efficiency

Active Publication Date: 2022-07-22
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Aiming at the problems that the pH of the reaction system must be controlled to be 10 in the existing uronic acid synthesis process, which makes the operation complicated, the human interference is serious, and the product post-treatment is difficult, the present invention provides a method for catalyzing the oxidation of pyranoside to synthesize uronic acid

Method used

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  • A kind of method for catalyzing oxidation of pyranoside to synthesize uronic acid
  • A kind of method for catalyzing oxidation of pyranoside to synthesize uronic acid
  • A kind of method for catalyzing oxidation of pyranoside to synthesize uronic acid

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Embodiment 1

[0031] The embodiment of the present invention provides a kind of method for catalyzing oxidation methyl-α-D-glucopyranoside to obtain methyl-α-D-glucuronide, and its concrete reaction process is as follows:

[0032]

[0033] In a 50mL three-necked round bottom flask, add methyl-α-D-glucopyranoside 0.39g (2mmol), TEMPO 0.016g (0.1mmol) and water 10mL successively;

[0034] Under the condition that temperature is 0 DEG C, add calcium hypochlorite solid 0.31g (2.2mmol) in batches, feeding time is 10min, wait for feeding to end, carry out catalytic oxidation reaction, and reaction time is 4h;

[0035] After completion of the reaction, stand for layers, filter under reduced pressure, adjust the pH of the obtained filtrate to 2 with 4 mol / L HCl, concentrate under reduced pressure to remove solvent water, add 8 mL of methanol to the obtained concentrate, shake and filter to remove inorganic salts , the obtained filtrate was rotary evaporated to remove the solvent to obtain 0.388 ...

Embodiment 2

[0038] The embodiment of the present invention provides a method for catalyzing oxidation of methyl-α-D-galactopyranoside to obtain methyl-α-D-galacturonic acid, and its concrete reaction process is as follows:

[0039]

[0040]In a 50mL three-necked round-bottomed flask, add methyl-α-D-galactopyranoside 0.39g (2mmol), TEMPO 0.016g (0.1mmol) and water 40mL in turn;

[0041] Under the condition that temperature is 10 ℃, add calcium hypochlorite solid 0.43g (3mmol) in batches, feeding time is 10min, wait for feeding to end, carry out catalytic oxidation reaction, and the reaction time is 3h;

[0042] After completion of the reaction, stand for stratification, filter under reduced pressure, adjust the pH of the obtained filtrate to 3 with 3 mol / L HCl, concentrate under reduced pressure to remove solvent water, add 8 mL of ethanol to the obtained concentrate, shake and filter to remove inorganic salts , the obtained filtrate was rotary evaporated to remove the solvent to obtain...

Embodiment 3

[0045] The embodiment of the present invention provides a kind of method that catalytic oxidation methyl-α-D-mannopyranoside obtains methyl-α-D-mannopyranoic acid, and its concrete reaction process is as follows:

[0046]

[0047] In a 50mL three-necked round-bottomed flask, add methyl-α-D-mannopyranoside 0.39g (2mmol), TEMPO 0.032g (0.02mmol) and water 30mL successively;

[0048] Under the condition that temperature is 20 DEG C, add calcium hypochlorite solid 0.57g (4mmol) in batches, and the feeding time is 10min. When the feeding is finished, carry out catalytic oxidation reaction, and the reaction time is 1h;

[0049] After completion of the reaction, stand for stratification, filter under reduced pressure, adjust the pH of the obtained filtrate to 2 with 5 mol / L HCl, concentrate under reduced pressure to remove solvent water, add 8 mL of methanol to the obtained concentrate, shake and filter to remove inorganic salts , the obtained filtrate was rotary evaporated to rem...

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Abstract

The invention relates to the technical field of chemical synthesis, and specifically discloses a method for synthesizing uronic acid by catalytic oxidation of pyranoside. The method takes pyranoside as raw material, takes TEMPO as catalyst, and takes Ca(OCl) 2 Be an oxidizing agent, carry out catalytic oxidation reaction in water to obtain uronic acid, wherein the ratio of the amount of pyranoside to TEMPO is 1:0.01-0.1, pyranoside and Ca(OCl) 2 The ratio of the amount of substances is 1:1.1‑2. The invention does not need to add an additional acid-base regulator in the reaction process, reduces the types and amounts of reagents required by the reaction system, not only simplifies the reaction process, avoids human errors and interference, but also greatly reduces the inorganic salts produced by the reaction system. It is beneficial to the purification and separation of uronic acid, more in line with the concept of atomic economic chemistry, and more conducive to industrialization.

Description

technical field [0001] The present invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing uronic acid by catalytic oxidation of pyranoside. Background technique [0002] The key to the synthesis of uronic acid structure lies in the selective oxidation of the primary hydroxyl group in the glycoside molecule to a carboxylic acid. Currently, environmentally friendly 2,2,6,6-tetramethylpiperidine oxide (TEMPO) and hypochlorous acid are mainly used. Salts form a cyclic oxidation system that oxidizes glycoside molecules. Solid Ca(OCl) compared to NaClO in solution 2 It also has the advantages of stable properties, easy operation and good controllability, which are suitable for industrial scale production. Therefore, TEMPO and Ca(OCl) are mainly used. 2 A cyclic oxidation system is formed. But TEMPO-Ca(OCl) 2 The combination of catalytic oxidation must not only be carried out in an alkaline environment, but also need to contro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H1/00C07H1/06C07H7/033
CPCC07H1/00C07H1/06C07H7/033
Inventor 刘文清王亚军
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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