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Method for synthesizing achiral glycidol

A glycidol and achiral technology, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., can solve the problems not mentioned in the synthesis and application of achiral Salen catalysts, etc. Achieve the effect of no optical activity, easy operation and high yield

Inactive Publication Date: 2012-06-27
CHENGDA PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the relevant literature, there is no mention of the synthesis of achiral Salen catalysts and the application of Salen catalysts in the production of achiral monochloroglycerin

Method used

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  • Method for synthesizing achiral glycidol
  • Method for synthesizing achiral glycidol
  • Method for synthesizing achiral glycidol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Add 4.0g (0.035mol) trans-1,2-cyclohexanediamine, 16.8g (0.071mol) 2-hydroxy-3,5-di-tert-butylbenzaldehyde and 600mL methanol into a 2L four-necked flask , heated to 60°C, vigorously stirred and reacted for 3 hours, cooled to 40°C, added 17.0g (0.068mol) cobalt acetate tetrahydrate, heated to 60°C and stirred for 2 hours, then added 4.2g (0.070mol) to the reaction system mol) acetic acid, and oxidized by passing air into it, stirred and reacted at 60°C for 1 hour, concentrated by distillation, added 150mL of water, cooled to 10°C, stirred and crystallized, filtered, and the solid was washed with water to obtain 18.1g (0.027mol) of Salen-Co catalyst with a yield of 78%.

[0037] (2) Add 1.9g (0.0028mol) of achiral Salen-Co catalyst to 130g (1.4mol) of racemic epichlorohydrin, cool to 10°C, add 38g (1.5mol) of water dropwise, and maintain at React at 10-20°C for 20 hours. After completion of the reaction, add 0.5 g vitamin C, stir for 30 minutes, filter, and carry o...

Embodiment 2

[0040] (1) Mix 5.7g (0.050mol) of 1,2-cyclohexanediamine (trans:cis=70:30), 17.8g (0.10mol) of 2-hydroxyl-4-tert-butylbenzaldehyde Add 700mL of toluene into a 2L four-necked flask, heat to 60°C, stir vigorously for 3 hours, cool to 40°C, add 17.0g (0.068mol) cobalt acetate tetrahydrate, heat to 60°C and stir for 2 hours, Concentrate by distillation, add 150 mL of water, cool to 10°C, stir to crystallize, filter, and wash the solid with water to obtain 15.6 g (0.028 mol) of achiral Salen-Co catalyst precursor with a yield of 57%.

[0041] (2) Add 1.8g (0.0028mol) of achiral Salen-Co catalyst precursor to 130g (1.4mol) of racemic epichlorohydrin, add 0.3mL of acetic acid, oxidize with air for 30 minutes, and cool to At 5°C, 45g (2.5mol) of water was added dropwise, and the reaction was maintained at 5-10°C for 12 hours. After completion of the reaction, add 0.5 g vitamin C, stir for 30 minutes, filter, and carry out vacuum distillation on the filtrate, collect 80-84 ° C / 1 mmHg ...

Embodiment 3

[0043] (1) Add 3.0g (0.050mol) of 1,2-ethylenediamine, 16.8g (0.071mol) of 2-hydroxy-3,5-di-tert-butylbenzaldehyde and 500mL of ethanol into a 1L four-necked flask, heat to 60°C, vigorously stirred and reacted for 3 hours, cooled to 40°C, added 16.7g (0.068mol) manganese acetate tetrahydrate, heated to 60°C, stirred and reacted for 2 hours, concentrated by distillation, added 150mL of water, cooled to 10°C, Stir to crystallize, filter, and wash the solid with water to obtain 27.7 g (0.042 mol) of achiral Salen-Mn catalyst precursor with a yield of 84%.

[0044] (2) Join 1.8g (0.0028mol) achiral Salen-Mn catalyst precursor into 130g (1.4mol) racemized epichlorohydrin, add 0.3mL acetic acid, oxidize with air for 30 minutes, cool to At 5°C, 45g (2.5mol) of water was added dropwise, and the reaction was maintained at 5-10°C for 12 hours. After completion of the reaction, add 0.5 g vitamin C, stir for 30 minutes, filter, and carry out vacuum distillation on the filtrate, collect 8...

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Abstract

The invention discloses a method for synthesizing achiral glycidol, aims to provide a new method suitable for industrialized production, being environment-friendly and being higher in yield, and belongs to the field of chemical synthesis. The method comprises the following steps of: taking achiral vicinal diamine and ortho-hydroxybenzaldehyde as raw materials, and continuously performing multistep reaction of condensation, transition metal coordination, oxidization and the like, according to the one-pot method, thereby efficiently synthesizing a plurality of achiral Salen catalysts. Under the action of the achiral Salen catalysts, the hydrolysis of racemized epoxy chloropropane is realized; the obtained glycerin chlorohydrin is subjected to alkaline cyclizing reaction, thereby synthesizing the achiral glycidol with high yield; and in the whole process flow, the operation is convenient, the products are completely racemized and no optical activity exists.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a method for synthesizing achiral glycidol by using racemic epichlorohydrin as a starting material, in particular to a method for epichlorohydrin to be synthesized under the action of an achiral Salen catalyst. Hydrolysis to generate chloroglycerol, and then cyclization to obtain achiral glycidol. Background technique [0002] Glycidol is also called glycidol, its chemical name is 2,3-epoxy-1-propanol, and its chemical structure is: [0003] [0004] 2,3-Epoxy-1-propanol [0005] Glycidol is an important chemical raw material. It can be used as an intermediate in the synthesis of surfactants, resins, plastics, elastomers, paints, dyes, etc., and can also be used in the extraction and separation of various solvents. Its derivatives are widely used Used in industries such as resin, plastic, medicine, pesticide and auxiliaries. In the chemical structural formula of glycidol, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/14C07D301/26B01J31/22
Inventor 彭智勇李继超葛建利
Owner CHENGDA PHARM CO LTD
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