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Preparation method of trimethylphenylammonium tribromide and recycling method of trimethylphenylammonium tribromide in naproxen production

A technology of trimethylphenylammonium tribromide and methylphenylammonium tribromide, which is applied to the preparation of amino compounds from amines, the preparation of functional groups replaced by amino groups, the purification/separation of amino compounds, etc., which can solve the problems of losing market competition, Naproxen industrialization cost increase and other problems, to achieve the effect of reducing production cost, low cost and high yield

Inactive Publication Date: 2019-09-13
CHONGQING MEDICAL & PHARMA COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Trimethylphenylammonium tribromide is an important raw material in the production of naproxen. However, the market price of about 2,000 yuan per kilogram increases the industrialization cost of naproxen sharply and loses market competition.

Method used

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  • Preparation method of trimethylphenylammonium tribromide and recycling method of trimethylphenylammonium tribromide in naproxen production
  • Preparation method of trimethylphenylammonium tribromide and recycling method of trimethylphenylammonium tribromide in naproxen production
  • Preparation method of trimethylphenylammonium tribromide and recycling method of trimethylphenylammonium tribromide in naproxen production

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The preparation of PTT, reaction formula is:

[0027]

[0028] In an Erlenmeyer flask equipped with a thermometer and a magnetic stirrer, a solution of 248 g (260 mL, 2 moles) of freshly distilled xylidine and 1000 mL of toluene was added. Stir to dissolve and heat to 35°C with stirring. The heating was stopped and 190 ml (2 moles) of freshly distilled dimethyl sulfate were added over 20 minutes via the dropping funnel. After a few minutes, the colorless ammonium methyl sulfate salt began to crystallize. During the dropwise addition, the temperature changed slightly, and after 1 hour after the dropwise addition, the temperature rose slowly to 50° C. due to the exothermic reaction. It was then reacted for an additional 1.5 hours at room temperature (i.e. without heating the reaction), followed by heating on a steam bath for 1 hour. After cooling, the ammonium phenyltrimethylmethylsulfate was filtered, washed with 200 ml of dry toluene and dried under vacuum. Obtai...

Embodiment 2

[0032] Preparation of PTT

[0033] In an Erlenmeyer flask equipped with a thermometer and a magnetic stirrer, a solution of 248 g (260 mL, 2 moles) of freshly distilled xylidine and 1000 mL of toluene was added. Stir to dissolve and heat to 45°C with stirring. The heating was stopped and 228 ml (2.4 moles) of freshly distilled dimethyl sulfate were added over 20 minutes via the dropping funnel. After a few minutes, the colorless ammonium methyl sulfate salt began to crystallize. During the dropwise addition, the temperature changed slightly, and one hour after the dropwise addition, the temperature rose slowly to 55°C. It was then reacted for a further 1.5 hours at room temperature and then heated on a steam bath for 1 hour. After cooling, ammonium phenyltrimethylmethylsulfate was filtered, washed with 200 ml of dry toluene, and dried under vacuum. Obtain 465 grams of phenyl trimethyl ammonium methyl sulfate, yield 94%.

[0034] In an Erlenmeyer flask, 100 g (0.4 mol) of ...

Embodiment 3

[0037] Preparation of PTT

[0038] In an Erlenmeyer flask equipped with a thermometer and a magnetic stirrer, a solution of 248 g (260 mL, 2 moles) of freshly distilled xylidine and 1000 mL of toluene was added. Stir to dissolve and heat to 40°C with stirring. The heating was stopped and 209 ml (2.2 moles) of freshly distilled dimethyl sulfate were added over 20 minutes via the dropping funnel. After a few minutes, the colorless ammonium methyl sulfate salt began to crystallize. During the dropwise addition, the temperature changed slightly, and one hour after the dropwise addition was completed, the temperature rose slowly to 45°C. It was then reacted for a further 1.5 hours at room temperature and then heated on a steam bath for 1 hour. After cooling, ammonium phenyltrimethylmethylsulfate was filtered, washed with 200 ml of dry toluene, and dried under vacuum. Obtain 440 grams of phenyl trimethyl ammonium methyl sulfate, yield 89%.

[0039] In an Erlenmeyer flask, 100 g...

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Abstract

The invention provides a preparation method of trimethylphenylammonium tribromide, comprising the following steps: using xylidine as a starting material and performing a reaction between xylidine anddimethyl sulfate to generate phenyltrimethylammonium methyl sulfate, dissolving phenyltrimethylammonium methyl sulfate in a hydrobromic acid solution, dropwise adding bromine and reacting, filtering,washing with water to obtain a crude product, and recrystallizing the crude product to obtain the product. The invention also discloses a recycling method of trimethylphenylammonium tribromide in thenaproxen production, and the recycling method is characterized by comprising the following steps: adding a hydrobromic acid solution into an aqueous solution obtained after a bromination reaction of trimethylphenylammonium tribromide in the naproxen production, dropwise adding bromine, stirring and reacting at room temperature after dropwise addition, filtering after the reaction, washing with water, and drying to obtain the product. The yield is high, cost is low, and the operation is simple.

Description

technical field [0001] The present invention relates to a kind of preparation method of trimethylphenylammonium tribromide and the recycling method of trimethylphenylammonium tribromide in the production of naproxen, belonging to the field of organic synthesis. Background technique [0002] Naproxen, as an important drug in the field of anti-inflammatory and antibacterial, plays an important role in the fields of anti-inflammatory, antipyretic and analgesic. Various types of rheumatic tendonitis, periarthritis of the shoulder, etc. [0003] Naproxen is a large-tonnage product, and the cost is very important under the fierce market competition. Trimethylphenyltriammonium tribromide is called for short PTT, is good selective bromination reagent, is the excellent raw material of selective bromination in the naproxen synthesis technique. The reaction formula of PTT bromination production naproxen is: [0004] [0005] The operation of bromination reaction is: [0006] Put...

Claims

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Application Information

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IPC IPC(8): C07C209/68C07C211/64C07C209/86
CPCC07C209/22C07C209/68C07C209/86C07C211/64
Inventor 刘殿卿何东贤王琨郭胜超吕君江王光明
Owner CHONGQING MEDICAL & PHARMA COLLEGE
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