Process for the production of dihydrolipoic acid

A technology of dihydrolipoic acid and dichlorooctanoic acid, which is applied in the direction of mercaptan preparation and organic chemistry, and can solve problems such as low selectivity

Active Publication Date: 2019-05-21
ALZCHEM TROSTBERG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Disadvantages of this synthetic route are the low selectivity of the radical addition of cyclohexanone to vinyl derivatives, the appearance of product mixtures after the Baeyer-Villiger oxidation, and the consequent need for distillation purification of thermally unstable products

Method used

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  • Process for the production of dihydrolipoic acid
  • Process for the production of dihydrolipoic acid
  • Process for the production of dihydrolipoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] 123.0 g (500 mmol) of racemic 6,8-dichloroethyl octanoate and 14.4 g (450 mmol, 0.9 equivalent) of sulfur was pre-placed in 123.0 g of ethanol. The autoclave was closed and heated to an internal temperature of 110° C. with stirring. At this temperature, 50.7 g of Na 2 S (650mmol, 1.3 equivalents) of 412.5g aqueous sodium sulfide (12.3% by weight Na in water 2 S). Here, the pressure increased from the initial 0.33MPa to 0.43MPa. Stirring of the reaction mixture was continued at 110 °C for 120 min, then cooled to 50 °C and transferred to a 2000 ml four-necked flask with stirrer, metering pump, internal thermometer, reflux cooler and oil bath heater. A solution of 94.6 g of sodium borohydride (12% by weight) in sodium hydroxide solution (40% by weight) containing 11.4 g of NaBH was uniformly added dropwise within 30 min at 70°C 4 (300 mmol, 0.60 equiv). The ethanol contained was substantially distilled from the reaction mixture over a period of 60 min (up to a distil...

Embodiment 2

[0061] Example 2 (comparative example not according to the invention):

[0062] 123.0 g (500 mmol) of racemic 6,8-dichloroethyl octanoate and 14.4 g (450 mmol, 0.9 equivalents) of sulfur Preliminary in 123.0 g of ethanol and heated to an internal temperature of 75° C. under normal pressure. At this temperature, 50.7 g of Na 2 S (650mmol, 1.3 equivalents) of 412.5g aqueous sodium sulfide (12.3% by weight Na in water 2 S) and then continue to stir the reaction mixture at 75°C for 120 min. The reaction contents were cooled to a temperature of 70° C. and then a solution of 94.6 g of sodium borohydride (12% by weight) in sodium hydroxide solution (40% by weight) containing 11.4 g of NaBH was added dropwise uniformly within 30 min. 4 (300 mmol, 0.60 equiv). The ethanol contained was substantially distilled from the reaction mixture over a period of 60 min (up to a distillation head temperature of 98° C.). Then a further 47.3 g of a solution of sodium borohydride (12 wt %) in so...

Embodiment 3

[0065] 123.0 g (500 mmol) of racemic 6,8-dichloroethyl octanoate and 16.0 g (500 mmol, 1.0 equivalent) of sulfur was pre-placed in 123.0 g of ethanol. The autoclave was closed and heated to an internal temperature of 110° C. with stirring. At this temperature, 51.8 g of Na 2S (663 mmol, 1.33 equiv) in 421.0 g of aqueous sodium sulfide (12.3% by weight). Here, the pressure increased from an initial 0.29 MPa to 0.45 MPa. Stirring of the reaction mixture was continued at 110 °C for 120 min, then cooled to 50 °C and transferred to a 2000 ml four-necked flask with stirrer, metering pump, internal thermometer, reflux cooler and oil bath heater. A solution of 99.3 g of sodium borohydride (12% by weight) in sodium hydroxide solution (40% by weight) containing 11.9 g of NaBH was uniformly added dropwise within 30 min at 70°C 4 (315 mmol, 0.63 equiv). The ethanol contained was substantially distilled from the reaction mixture over a period of 60 min (up to a distillation head tempe...

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Abstract

The present invention relates to a multi-step process for the production of dihydrolipoic acid, which can particularly be carried out as a one-pot reaction and without isolation of intermediates.

Description

technical field [0001] The present invention relates to a multi-step process for the preparation of dihydrolipoic acid which can be carried out in particular in a one-pot format and without isolation of intermediate products. Background technique [0002] Dihydrolipoic acid (C 8 h 16 o 2 S 2 ; 6,8-Dimercaptooctanoic acid; CAS No. 462-20-4) [0003] [0004] is a sulfur-containing carboxylic acid that can be described as alpha-lipoic acid (C 8 h 14 o 2 S 2 ; 5-(1,2-dithiapentan-3-yl)-pentanoic acid; CAS No. 1077-28-7) and has two SH groups instead of one compared to alpha-lipoic acid S-S sulfur bridge. Both dihydrolipoic acid and alpha-lipoic acid can exist in two enantiomeric forms (see R-dihydrolipoic acid (Formula Ia) and S-dihydrolipoic acid (Formula Ib)). [0005] [0006] Dihydrolipoic acid is a compound present in human organs in physiological equilibrium with α-lipoic acid, a substance also long known as a growth factor in microorganisms (also known as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/52
CPCC07C323/52C07C319/06
Inventor I·施纳派莱勒S·温克勒J·桑斯F·塔尔哈麦尔
Owner ALZCHEM TROSTBERG
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