Synthesis method of L-carnitine

A synthesis method and technology of L-carnitine, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of high ammonia nitrogen value in wastewater and high equipment requirements, achieve high reaction yield, short reaction time, The effect of mild reaction conditions

Inactive Publication Date: 2011-04-20
ZHEJIANG UNIV OF TECH +1
View PDF4 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The hydrolysis method of the intermediate nitrile compound (L-(-)-3-cyano-2-hydroxypropyltrimethylammonium halide) mostly adopts concentrated hydrochloric acid hydrolysis method, and the disadvantage is that the requirements for equipment are relatively high
Ion exchange often adopts cation exchange resin, which is eluted with a large amount of ammonia water, and the ammonia nitrogen value of waste water is high, which brings great environmental pressure. Therefore, it is of great significance to develop an environmentally friendly and easy-to-industrial production of L-carnitine. Synthesis method

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesis method of L-carnitine
  • Synthesis method of L-carnitine
  • Synthesis method of L-carnitine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The ratio of the amount of feed material L-(-)-3-cyano-2-hydroxypropyltrimethylammonium chloride:hydrogen peroxide:basic compound is 1:10:2.

[0021] In a 250mL three-neck flask equipped with a thermometer, reflux condenser and mechanical stirring, add 17.8g (100mmol) of L-(-)-3-cyano-2-hydroxypropyltrimethylammonium chloride, slowly add 30% peroxide 120g (1000mmol) of hydrogen and 8g (200mmol) of sodium hydroxide, heat up to 70°C and react for 1.5h. After the reaction, cool down, add sodium sulfite until no bubbles are formed, concentrate the reaction solution, adjust the pH to about 5 with acid, pass through Amberlite IRA -400 anion resin exchange column, elute with distilled water, collect the eluent containing product, concentrate, then obtain L-carnitine 12.1g with ethanol-acetone (volume ratio 2: 1) recrystallization, product yield 75.1%, mp 196~197℃, [α] D 20 -32° (c 10, H 2 O).

Embodiment 2

[0023] The ratio of the amount of feed material L-(-)-3-cyano-2-hydroxypropyltrimethylammonium chloride:hydrogen peroxide:basic compound is 1:10:4.

[0024] In a 250mL three-neck flask equipped with a thermometer, reflux condenser and mechanical stirring, add 17.8g (100mmol) of L-(-)-3-cyano-2-hydroxypropyltrimethylammonium chloride, slowly add 30% peroxide 120g (1000mmol) of hydrogen and 16g (400mmol) of sodium hydroxide, heat up to 70°C and react for 1.5h. After the reaction, cool down, add sodium sulfite until no bubbles are formed, concentrate the reaction solution, adjust the pH to about 5 with acid, pass through Amberlite IRA -400 anion resin exchange column, elute with distilled water, collect the eluate containing product, concentrate, then obtain L-carnitine 12.8g with ethanol-acetone (volume ratio 2: 1) recrystallization, product yield 79.5%, mp 196~197℃, [α] D 20 -31.7° (c 10, H 2 O).

Embodiment 3

[0026] The ratio of the amount of feed material L-(-)-3-cyano-2-hydroxypropyltrimethylammonium chloride:hydrogen peroxide:basic compound is 1:10:6.

[0027] In a 250mL three-neck flask equipped with a thermometer, reflux condenser and mechanical stirring, add 17.8g (100mmol) of L-(-)-3-cyano-2-hydroxypropyltrimethylammonium chloride, and slowly add 40% peroxide Hydrogen 90g (1000mmol) and potassium hydroxide 33.6g (600mmol), heat up to 65°C and react for 1.0h, after the reaction, cool down, add sodium sulfite until no bubbles are formed, concentrate the reaction solution, adjust the pH to about 7 with acid, pass through Amberlite IRA-400 anion resin exchange column, eluting with distilled water, collecting the eluate containing product, concentrating, then recrystallizing with isopropanol-acetone (volume ratio 2: 1) to obtain L-carnitine 13.9g, product yield 86.3 %, mp 196~198℃, [α] D 20 -31.5° (c 10, H 2 O).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a synthesis method of L-carnitine with a structure shown in a formula (1), which adopts L-(-)-3-cyan-2-hydroxyl propyl trimethylamine halide as a raw material and is prepared by hydrolysis and ion exchange; the hydrolysis is carried out in the following steps: in alkaline solution, hydrogen peroxide is used for hydrolyzing the L-(-)-3-cyan-2-hydroxyl propyl trimethylamine halide, and after full reaction, the hydrolysis reaction liquid is obtained. In the technique disclosed in the invention, the reaction condition is mild, the reaction time is short, the reaction yield is high, three wastes are less, and the implementation value and social and economic benefits are larger.

Description

(1) Technical field [0001] The invention relates to a synthesis method of L-carnitine. (2) Background technology [0002] L-carnitine also known as vitamin B T , whose chemical name is (3R)-(-)-3-hydroxy-4-(trimethylamino)butyric acid, has a wide range of physiological activities. In 1985, the International Nutrition Academic Conference listed L-carnitine as an essential nutrient under certain conditions. In recent years, L-carnitine has been widely used in health care, weight loss and other fields. Its products are in short supply at home and abroad, and have high practical value. [0003] Before the present invention was made, what the original synthetic method of domestic production L-carnitine enterprise adopts more is that 1988 Japanese patent (JP63185947) reports with (S)-(+)-epichlorohydrin as starting raw material, and Trimethylamine is converted into quaternary ammonium salt to produce 3-chloro-2-hydroxypropyl trimethylamine halide, which is then cyanated to 3-cy...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/22C07C227/26
Inventor 陈志卫苏为科毕建豪张春雷陈炯明徐灿闯
Owner ZHEJIANG UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap