New method for preparing neta-thia-alpha-alkyl fatty acid

A technology of alkyl fatty acid and a new method, applied in the direction of sulfide preparation, organic chemistry, etc., can solve the problems of high production cost, many steps in the reaction process, and easy oxidation, etc., and achieve simple and stable production process, easy to obtain materials on site, The effect of little environmental pollution

Inactive Publication Date: 2008-07-23
SHANGHAI PUYI CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] But the smell of long-chain mercaptans is very smelly, which causes great pollution to the environment, and is prone to oxidation, causing problems such as low reaction yield and difficult product purification, which makes the product purity low, and because long-chain mercaptans have no industrial commodities supply, it is necessary to increase the process steps of synthesizing mercaptans, so that the whole reaction process has many steps, is more complicated, time-consuming and labor-intensive
high production cost

Method used

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  • New method for preparing neta-thia-alpha-alkyl fatty acid
  • New method for preparing neta-thia-alpha-alkyl fatty acid
  • New method for preparing neta-thia-alpha-alkyl fatty acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The preparation of embodiment 1.3-thia-2-methyltridecanoic acid

[0035] At room temperature, add 15.94g of sodium hydroxide (excessive) into 200ml of methanol, stir to dissolve it, add dropwise 18.3ml (21.88g, 0.206mol) of 2-mercaptopropionic acid, then dropwise add 22.1g (0.1mol) of 1- Bromodecane, react for 1.5-2 hours, a large amount of white solid precipitates, continue to stir until the reaction is complete, then add water and hydrochloric acid to the system to acidify, stir and mix well, filter the separated precipitate with suction, wash with water, and recrystallize from ethanol , 17.2g of crystals were obtained, the yield was 75%, mp.38.1-38.3°C, and the purity by GC analysis was 97.0%.

[0036] The obtained product is analyzed as follows:

[0037] White scaly crystals;

[0038] mp.38.1-38.3°C (recrystallized from EtOH);

[0039] IR(KBr)ν max : 2960, 2920, 2870, 1700, 1470, 1250cm -1 .

[0040] 1 H NMR (300MHz, CDCl 3 ): δ10.13 (bs, OH), 3.43 (q, 1H, J...

Embodiment 2

[0043] The preparation of embodiment 2.3-thia-2-methylpentadecanoic acid

[0044] At room temperature, add 17.4g of sodium hydroxide (excessive) into 200ml of methanol, stir to dissolve it, add dropwise 18.3ml (21.88g, 0.206mol) of 2-mercaptopropionic acid, and then add 24.9g (0.1mol) of decabromide Dioxane, reacted for 1.5-2 hours, a large amount of white solid precipitated, continued to stir until the reaction was complete, then added water and hydrochloric acid to the system, stirred, suction filtered the precipitate, washed with water, recrystallized from ethanol, filtered to obtain 20.6 g crystallization, yield 75.4%, mp. 51-52°C, GC analysis purity 97.0%.

[0045] The obtained product is analyzed as follows:

[0046] White scaly crystals;

[0047] mp.51-52°C (recrystallized from EtOH);

[0048] IR(KBr)ν max : 2960, 2920, 2870, 1700, 1470, 1250cm -1 ;

[0049] 1 H NMR (300MHz, CDCl 3 ): δ10.13 (bs, OH), 3.43 (q, 1H, J=6.6Hz, -SC H COOH), 2.59-2.69 (m, 2H, -C H 2 ...

Embodiment 3

[0052] The preparation of embodiment 3.3-thia-2-methylheptadecanoic acid

[0053] At room temperature, add 17.4g of sodium hydroxide (excess) into 200ml of methanol, stir to dissolve it, add dropwise 18.3ml (21.88g, 0.206mol) of 2-mercaptopropionic acid, and then add 25ml (27.7g, 0.1mol) of bromine Tetradecane, reacted for 1.5-2 hours, a large amount of white solids were precipitated, continued to stir until the reaction was complete, then added water and hydrochloric acid to the system, stirred, suction filtered the separated precipitates, washed with water, and recrystallized from ethanol to obtain 24.1 g crystallization, yield 79.8%, mp. 51.8-52.2°C, GC analysis purity 97.5%.

[0054] The obtained product is analyzed as follows:

[0055] White scaly crystals;

[0056] mp.51.8-52.2°C (recrystallized from EtOH);

[0057] IR(KBr)ν max : 2960, 2920, 2870, 1700, 1470, 1250cm -1 ;

[0058] 1 H NMR (300MHz, CDCl 3 ): δ10.13 (bs, OH), 3.41 (q, 1H, J=7.2Hz, -SC H COOH), 2.7...

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Abstract

The invention relates to a new preparation method of Beta-thia- Alpha -alkyl fatty acid, using alkyl halides and 2- mercapto carboxylic acid as materials. The alkyl halides and the 2- mercapto carboxylic acid are condensed, and then the Beta-thia- Alpha -alkyl fatty acid is obtained by one-step method. Beta-thia- Alpha -alkyl fatty acid with high purity is obtained by salting out, pumping filtration and recrystallization. The new preparation method of Beta-thia- Alpha -alkyl fatty acid has the advantages of little environmental pollution, high efficiency and stabilization, simple and easy operation, high purity of products, low production cost and adaptation of mass production.

Description

technical field [0001] The present invention relates to the field of compound synthesis, more specifically, to a new method for preparing β-thia-α-alkyl fatty acids. Background technique [0002] Long-chain thia fatty acids, also known as 3-thia-2-alkyl fatty acids, have chemical properties similar to ordinary fatty acids, but their metabolic mechanisms and effects are quite different. It was recently discovered that β-thia-α-alkyl fatty acids, also known as 3-thia-2-alkyl fatty acids, can change the fatty acid composition of phospholipids in heart and liver cells, activate the oxidation of fatty acids to reduce blood lipids, and inhibit Fatty acid and cholesterol in liver cells are synthesized, so it is more and more widely used in the field of medicine and health products. [0003] The molecular formula of β-thia-α-alkyl fatty acids is shown in the following formula: [0004] [0005] where R1 is C 10 -C 30 Saturated or unsaturated alkyl or aryl, the carbon atom of ...

Claims

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Application Information

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IPC IPC(8): C07C323/52C07C319/14
Inventor 郭廷翘王博
Owner SHANGHAI PUYI CHEM CO LTD
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