Method for preparing 5-methylthienyl-2-thiol from levulinic acid

A technology of levulinic acid and methylthiophene, applied in the direction of organic chemistry, etc., to achieve the effects of mild reaction conditions, simple steps and high product yields

Active Publication Date: 2016-05-11
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology involves making certain chemical products called Levidone (levulenic acid) using different starting substances like Lignocelanum). These technical results include improved yields, ease of production, easy isolation/purification, use at lower costs compared to traditional methods involving expensive specialized equipment. Additionally, this new technique allows us to produce these important molecules directly on demand instead of being produced separately.

Problems solved by technology

The technical problem addressed in this patents relates to finding ways to make better use of biofuels like lactic acid due to their potential benefits over traditional sources (petrochemistry).

Method used

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  • Method for preparing 5-methylthienyl-2-thiol from levulinic acid
  • Method for preparing 5-methylthienyl-2-thiol from levulinic acid
  • Method for preparing 5-methylthienyl-2-thiol from levulinic acid

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Effect test

Embodiment 1

[0031] Add 0.23g of levulinic acid to 15mL of toluene, and add Lawson's reagent twice the amount of the raw material, and react at 100°C for 5h under 1bar nitrogen atmosphere to obtain a light yellow transparent liquid. The solution was washed with 2 times the volume of sodium carbonate solution with a mass concentration of 10%, and then separated by vacuum distillation to obtain 5-methylthiophene-2-thiol with a yield of 62%.

Embodiment 2

[0033] Add 0.06 g of levulinic acid to 10 mL of xylene, and add Lawson's reagent in an amount 1 times that of the raw material, and react for 1 h at 110° C. under a nitrogen atmosphere of 1 bar to obtain a light yellow transparent liquid. The solution was washed with 1 volume of sodium hydrogen carbonate solution with a mass concentration of 5%, and then separated by vacuum distillation to obtain 5-methylthiophene-2-thiol with a yield of 46%.

Embodiment 3

[0035] Add 0.6 g of levulinic acid to 20 mL of toluene, and add 1.5 times the amount of Lawson's reagent as the raw material, and react at 110 ° C for 4 h in an air atmosphere of 1 bar to obtain a light yellow transparent liquid. The liquid was washed with 3 times volume of sodium carbonate solution with a mass concentration of 7.5%, and then separated by vacuum distillation to obtain 5-methylthiophene-2-thiol with a yield of 64%.

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Abstract

The invention provides a method for preparing 5-methylthienyl-2-thiol from levulinic acid, relating to thiophene compounds. The method comprises the following steps: adding levulinic acid into a solvent, and adding a Lawesson reagent to react; washing the product with an alkali, neutralizing 4-methoxyphenylphosphonic acid to obtain a salt, and transferring the salt into a water phase, wherein the target product 5-methylthienyl-2-thiol is retained in an organic phase and separated from the 4-methoxyphenylphosphonic acid; and carrying out reduced pressure distillation on the organic phase to obtain the 5-methylthienyl-2-thiol. The raw material reacts with the Lawesson reagent, and the 5-methylthienyl-2-thiol can be prepared by a cascade thionation-cyclization-isomerization process in one reaction procedure, so the steps are simple. The sodium carbonate or sodium bicarbonate solution is used for washing, so that the Lawesson reagent residue 4-methoxyphenylphosphonic acid can be effectively removed on the premise of not influencing the target product 5-methylthienyl-2-thiol. The obtained product has abundant reaction sites, such as aromatic thiophene rings, mercapto groups and the like, and has high plasticity.

Description

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Claims

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Application Information

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Owner XIAMEN UNIV
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