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Method for producing L-(R) propylidene glycerin

A technology of propylidene glycerol and its production method, which is applied in the direction of organic chemistry, can solve the problems of complicated process, unsuitable for large-scale production, and low production efficiency, and achieve the effect of reducing costs

Active Publication Date: 2006-04-05
PORTON FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, L-mannitol is a non-natural product with limited sources, which is not suitable for large-scale production of L-(R)-propylidene glycerol
[0010] ②Preparation from L-serine: Japanese Patent Publication BNo.6-62492 discloses a method for preparing L-(R)-propylidene glycerol by bio-fermentation using serine as raw material, which has been industrialized , this method requires specific enzymes and huge reaction equipment, with low production efficiency and limited output
This method is easier to control than the aforementioned method, and the resulting product has a higher purity, but it requires a special electrolytic cell and strict control of the current density, which is not convenient for industrial production
[0020] In summary, the methods for preparing L-(R)-propylidene glycerol in the prior art have the problems of high cost, complex process and low yield, and are difficult to industrialized production. Therefore, it is necessary to develop a low-cost and capable of industrialized production The process of L-(R)-propylidene glycerol is of great significance

Method used

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  • Method for producing L-(R) propylidene glycerin
  • Method for producing L-(R) propylidene glycerin
  • Method for producing L-(R) propylidene glycerin

Examples

Experimental program
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Embodiment 1

[0032] Synthesis of L-gulonic acid-1,4-lactone

[0033] Dissolve 23.1 grams of vitamin C in 170 milliliters of water, add 2.2 grams of 5% palladium / carbon catalyst, at 50 ° C and 5.05 × 10 5 Catalyzed hydrogenation under Pa for 24 hours, filtered to remove the catalyst, and evaporated the water under reduced pressure to obtain L-gulonic acid-1,4-lactone, which was recrystallized with a mixed solvent of methanol and ethanol to obtain 22 grams of the product with a yield of 95%. , melting point 182-183.5℃; [α] D 20 is +55.2° (c=1, H 2 O);

[0034] IR(KBr)1770cm -1 ;

[0035] 1 H-NMR (Me 2 SO-d 6 ):

[0036] δ=5.80 (d, 1, OH), 5.30 (d, 1, OH), 4.95 (d, 1, OH) 4.45-4.07 (m, 3), 4.00-3.35 (m, 3), 4.00-3.35 ( m, 3).

[0037] Synthesis of 5,6-O-isopropylidene-L-gulonic acid-1,4-lactone

[0038]Dissolve 221.6 grams of L-gulonic acid-1,4-lactone in 2000 milliliters of N,N-dimethylformamide, cool to 10°C, add 1.8 grams of p-toluenesulfonic acid while stirring, keep the tempe...

Embodiment 2

[0046] Synthesis of L-gulonic acid-1,4-lactone

[0047] Dissolve 200 kg of vitamin C in 1000 liters of water, add 20 kg of 10% palladium / carbon catalyst, at 50 ° C and 5.05 × 10 5 Catalyzed hydrogenation under Pa for 24 hours, filtered to remove the catalyst, and evaporated the water under reduced pressure to obtain a white solid of L-gulonic acid-1,4-lactone, which was recrystallized with a mixed solvent of methanol and ethanol to obtain 196 kg of white cubic crystals , yield 98%, melting point 183-183.5°C, [α] 25 is +55.5° (c=1, H 2 O).

[0048] Synthesis of 5,6-O-isopropylidene-L-gulonic acid-1,4-lactone

[0049] Dissolve 190 kg of L-gulonic acid-1,4-lactone in 1500 liters of N,N-dimethylformamide, cool to 10°C, add 1.8 kg of p-toluenesulfonic acid while stirring, keep the temperature below 10°C and drop Add 150 kg of 2,2-dimethoxypropane, continue stirring at room temperature for 24 hours, then add 220 kg of sodium carbonate decahydrate, filter after 2 hours, and disti...

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Abstract

The present invention produces L-(R)-propylidene glycerin with vitamin C as material and through the following steps: high pressure catalytic hydrogenation, 5, 6-hydroxy protection, oxidation with sodium periodate in oxidation system and reduction with reductant. The present invention features that mixed organic solvent and water as oxidation system and potassium borohydride and sodium borohydride as reductant are used to complete the oxidation and reduction steps in one reactor. The present invention has total L-(R)-propylidene glycerin yield up to 50 %, low cost, chemical product purity higher than 99.5 % and optical product purity higher than 99.9 %, and may be industrial used.

Description

technical field [0001] The invention relates to a production method of propylene glycol, in particular to a production method of L-(R)-propylidene glycerol (L-(R)-Glycerol Acetonide). Background technique [0002] Propylglycerol is an important intermediate in organic synthesis, which plays an important role in the synthesis of medicine and agricultural chemicals. Since propylglycerol has a chiral carbon atom and has a pair of enantiomers, the so-called propylglycerol is a racemate, which is the enantiomer L-(S)-propylidene glycerol, L-( R)-A mixture of propylidene glycerol, which can be easily prepared with glycerol and acetone under the catalysis of thionyl chloride. [0003] [0004] L-(R)-Propylglycerol L-(S)-Propylglycerol [0005] Optically pure propylene glycol can be used as a chiral source for asymmetric synthesis in organic synthesis, which is of great significance in the development of chiral drugs. Although optically pure propylidene glycerol can be obtai...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/20
Inventor 冰青
Owner PORTON FINE CHEM