Environment-friendly synthesis method of D-calcium pantothenate intermediate D, L-pantoyl lactone

A pantolactone and lactonization technology, applied in organic chemistry and other directions, can solve problems such as large amount of formaldehyde and sodium hydroxide used, high COD in wastewater, unfavorable environmental protection, etc., and achieves high raw material atom economy and separation. Fewer processes and lower energy consumption

Active Publication Date: 2016-10-12
XINFA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Although the method improves the yield, 30% formaldehyde and sodium hydroxide are used in a large amount in the disproportionation reaction, and the reaction temperature is higher. After the disproportionation reaction

Method used

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  • Environment-friendly synthesis method of D-calcium pantothenate intermediate D, L-pantoyl lactone
  • Environment-friendly synthesis method of D-calcium pantothenate intermediate D, L-pantoyl lactone
  • Environment-friendly synthesis method of D-calcium pantothenate intermediate D, L-pantoyl lactone

Examples

Experimental program
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Effect test

Embodiment 1

[0044] Embodiment 1: the preparation of D, L-pantolactone

[0045] Add 19.0 grams (0.1 moles) of 40 wt% glyoxylic acid and 0.5 grams of triethylamine to a 250 milliliter four-necked flask, and add 7.0 grams (0.1 moles) of isobutyraldehyde dropwise between 20 and 25 ° C. React at 30°C for 3 hours. Transfer the resulting reaction liquid to a 250 ml stainless steel pressure vessel, add 30 g of 1,2-dichloroethane, 0.2 g of 5% palladium carbon catalyst, pass in hydrogen, keep at 2-3 atmospheric pressure, stir and catalyze at 20-25°C The hydrogenation reaction was carried out for 4 hours. Filter and recover the catalyst. Add 0.3 g of 75% sulfuric acid (accounting for 5.71% of isobutyraldehyde after conversion) to the filtrate, and react at 80-85°C for 3 hours; Dichloroethane extraction, 20 grams each time, combined organic phases, washed with 10 grams of 1.0% sodium carbonate aqueous solution, washed with 10 grams of saturated sodium chloride aqueous solution, recovered 1,2-dichl...

Embodiment 2

[0046] Embodiment 2: the preparation of D, L-pantolactone

[0047] Add 19.6 grams (0.11 moles) of 40% glyoxylic acid and 0.4 grams of piperidine to a 250 ml four-neck flask, add 7.0 grams (0.1 moles) of isobutyraldehyde dropwise between 15 and 20 °C, after the drop is completed, set the temperature at 20 to 25 °C React for 3 hours. Transfer the resulting reaction liquid to a 250 ml stainless steel pressure vessel, add 40 g of n-butyl acetate, 0.2 g of 5% palladium carbon catalyst, feed hydrogen, keep at 2-3 atmospheric pressure, and stir at 20-25 ° C for catalytic hydrogenation reaction 4 Hour. Filter and recover the catalyst. Add 0.3 g of 85% sulfuric acid (accounting for 5.04% of isobutyraldehyde after conversion) to the filtrate, and react at 90-95°C for 3 hours; after the reaction is completed, cool to 15-20°C, separate layers, and use n-butyl acetate for the water layer Extraction, 20 grams each time, combined organic phases, washed with 10 grams of 1.0% aqueous sodium...

Embodiment 3

[0048]Embodiment 3: D, the preparation of L-pantolactone

[0049] Add 19.6 grams (0.11 moles) of 40% glyoxylic acid and 0.4 grams of tri-n-butylamine to a 250 milliliter four-necked flask, and add 7.0 grams (0.1 moles) of isobutyraldehyde dropwise between 20 and 25°C. React at 30°C for 3 hours. Transfer the resulting reaction liquid to a 250ml stainless steel pressure vessel, add 40g of 1,2-dichloroethane, 0.5g of 50% Raney nickel catalyst, feed hydrogen, keep stirring at 30-35°C under 3-4 atmosphere pressure The catalytic hydrogenation reaction was carried out for 4 hours. Filter and recover the catalyst. Add 0.3 g of 75% sulfuric acid to the filtrate, react at 80-85°C for 3 hours; after the reaction is complete, cool to 15-20°C, separate layers, extract the water layer with 1,2-dichloroethane, 20 g each time, combine The organic phase was washed with 10 g of 1.0% sodium carbonate aqueous solution and 10 g of saturated sodium chloride aqueous solution. After the organic ph...

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Abstract

The invention relates to an environment-friendly synthesis method of a D-calcium pantothenate intermediate D, L-pantoyl lactone. According to the method, isobutyraldehyde and glyoxylic acid are utilized to prepare 2-hydroxy-3-methyl-3-formyl butyric acid (II) under the catalytic action of organic alkali in an aldol condensation mode, then catalytic hydrogenation is conducted, 2,4-dyhydroxy-3,3-dimethyl butyric acid (III) is obtained, after the catalyst is filtered out, the filtrate is subjected to lactonization under the acidic condition, and the D, L-pantoyl lactone is obtained. The raw materials used for the method are cheap and easy to obtain, the technological process is short, product cost is low, less wastewater is generated, and treatment is easy to conduct; highly toxic raw materials are avoided, and operation is safe.

Description

technical field [0001] The invention relates to an environment-friendly synthesis method of D, L-pantolactone, an intermediate of calcium D-pantothenate, and belongs to the technical field of vitamin production. Background technique [0002] Calcium D-pantothenate, or calcium D-pantothenate, vitamin B5, its chemical name is D-(+)-N-(2,4-dihydroxy-3,3-dimethylbutyryl)-β-aminopropyl Calcium acid, white or yellowish crystalline powder, is an important food and feed additive. The main way to prepare calcium D-pantothenate is to obtain D-pantoate lactone through biological or chemical resolution of D,L-pantoate lactone, and then react with β-alanine to obtain D-pantoate. Calcification to prepare calcium D-pantothenate. [0003] U.S. Patent No. 4200582 uses isobutyraldehyde and formaldehyde as raw materials, first carries out methylolation, and then performs addition reaction with sodium cyanide, and hydrolyzes the cyano group under acidification conditions to obtain 2,4-dihydro...

Claims

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Application Information

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IPC IPC(8): C07D307/33
CPCC07D307/33
Inventor 戚聿新王涛王海涛鞠立柱李新发
Owner XINFA PHARMA
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