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Recovery treatment method and application of levonorgestrel mother liquor

A technology for recovery and treatment of levonorgestrel, which is applied in the field of recovery and treatment of levonorgestrel mother liquor, can solve the problems of resource waste, high treatment cost, and low recycling rate, and achieve reduced impact and high material utilization rate , High recovery effect

Active Publication Date: 2020-04-24
HUBEI GEDIAN HUMANWELL PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Because the two-step synthesis is not completely converted in production, the mother liquor composition of the refined levonorgestrel is complex, mainly containing ethyl Woshi hydrolyzate, levonorgestrel, ethyl lithium ammonia hydrolyzate, ethyl lithium ammonia hydrolyzate, The main components such as worstite and ethyllithium ammonium, therefore, it is difficult to separate and recover the mother liquor of levonorgestrel
At present, the treatment method of levonorgestrel mother liquor is to carry out multiple solvent refining and purification to obtain a small amount of ethyl Woshi hydrolyzate, but the recycling rate is low and the treatment cost is high. Most manufacturers use levonorgestrel mother liquor Dispose of it directly as waste liquid, causing a waste of resources and polluting the environment

Method used

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  • Recovery treatment method and application of levonorgestrel mother liquor
  • Recovery treatment method and application of levonorgestrel mother liquor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] A kind of recovery treatment method of levonorgestrel mother liquor, comprises the steps:

[0030] (1) Take the obtained mother liquor in the process of synthesizing levonorgestrel with the ethyl Woshi thing as raw material (contain solvent acetone, except solvent, by mass percentage, ethyl Woshi hydrolyzate 50%, levonorgestrel 30% of ketone, 10% of ethyllithium ammonia hydrolyzate, 10% of ethyllithium ammonium and ethyl Wormwood and other impurities) 1L in reaction flask 1, add 10mL of concentrated hydrochloric acid, heat to reflux, and monitor the reaction by HPLC. After the reaction was completed, 10 mL of ammonia water was finally added to stop the reaction, filtered, and the solvent was concentrated to dryness to obtain 50 g of the crude product.

[0031] (2) Add 50g of crude product 1 into reaction bottle 2, add 500mL of chloroform and stir to reflux with water, then add 10g of aluminum isopropoxide and 50g of cyclohexanone to reflux, and monitor the reaction by H...

Embodiment 2

[0034] A kind of recovery treatment method of levonorgestrel mother liquor, comprises the steps:

[0035] (1) Take the obtained mother liquor in the process of synthesizing levonorgestrel with the ethyl Woshi thing as raw material (containing solvent acetone, except the solvent, in mass percent, ethyl Woshi hydrolyzate 40%, levonorgestrel 20% of ketone, 5% of ethyllithium ammonia hydrolyzate, 35% of ethyllithium ammonium and ethyl Wormwood and other impurities) 1L in reaction flask 1, add 10mL of concentrated hydrochloric acid, heat to reflux, and monitor the reaction by HPLC. After the reaction was completed, 10 mL of ammonia water was finally added to stop the reaction, filtered, and the solvent was concentrated to dryness to obtain 55 g of the crude product.

[0036] (2) Add 55g of crude product 1 into reaction bottle 2, add 550mL of chloroform and stir to reflux with water, then add 11g of aluminum isopropoxide and 55g of cyclohexanone to reflux, and monitor the reaction b...

Embodiment 3

[0039] A method for synthesizing levonorgestrel, using the recovered product of levonorgestrel mother liquor in Example 1 as raw material, prepared by acetylenation reaction, the specific steps are as follows:

[0040] (1) Preparation of potassium alkyne: slowly add acetone (10 mL) to 200 mL THF, 60 g KOH at room temperature, and heat at 35-40 ° C for 2 h with acetylene gas.

[0041] (2) Alkynylation reaction: After the potassium alkyne reaction is completed, the temperature is lowered to 0-5 ° C, and 20 g of the THF solution prepared by the mixture of ethyl Woshi hydrolyzate and levonorgestrel recovered in Example 1 is added dropwise. After the dropwise addition, continue Pass acetylene gas and keep warm at 0-5°C for 3h.

[0042] (3) Hydrolysis reaction: After the alkynylation reaction is completed, stop passing acetylene gas to replace the nitrogen gas, add 150 mL concentrated hydrochloric acid to the reaction solution, and then reflux for 1 h.

[0043](4) Post-treatment: A...

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Abstract

The invention discloses a recovery treatment method and an application of a levonorgestrel mother liquor. The method comprises the following steps: adding concentrated hydrochloric acid into the levonorgestrel mother liquor, performing heating refluxing for acid hydrolysis, adding aluminum isopropoxide, carrying out Oppenauer oxidation to convert ethyl lithium ammonia hydrolysate, ethyl lithium ammonia and ethyl methoxydienone into ethyl Oppenauer hydrolysate, and obtaining the recovered product which is a mixture of the ethyl Oppenauer hydrolysate and levonorgestrel. The recovery method is simple to operate and high in recovery rate, and the recovered product can be used for preparing the levonorgestrel through return alkynylation, so that the utilization rate of each component of the mother liquor is improved.

Description

technical field [0001] The invention relates to the recovery and utilization of steroid drug mother liquor, in particular to a method for recycling and processing the mother liquor of levonorgestrel and its application. Background technique [0002] Levonorgestrel is an emergency contraceptive, which can inhibit ovulation and can be used in combination with estrogen. It belongs to short-acting and long-acting oral contraceptives, and is currently widely used in China. In addition, levonorgestrel can also be used to treat irregular menstruation, endometriosis, uterine dysfunctional bleeding, etc. [0003] The synthesis route of levonorgestrel is relatively long, and the last two steps of the process are generally from the intermediate ethyllithium ammonium through Woxfield oxidation and acetylenic hydrolysis to finally obtain levonorgestrel: [0004] [0005] Because the two-step synthesis is not completely converted in production, the mother liquor composition of the ref...

Claims

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Application Information

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IPC IPC(8): C07J1/00
CPCC07J1/0051C07J1/0066
Inventor 左权刘林徐仙凤杨艳青汪钧杜晓东倪文飞
Owner HUBEI GEDIAN HUMANWELL PHARMACEUTICAL CO LTD
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