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Method for synthesizing dimeric acid by lipoxygenase one-step process

A technology of lipoxygenase and dimer acid, which is applied in the field of synthesis of dimer acid, can solve the problems of affecting product quality and yield, increasing the difficulty of separation, prone to side reactions such as oxidation and polymerization, and achieving low cost Control and improve the effect of preparation conditions

Inactive Publication Date: 2013-07-31
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unsaturated fatty acids become very unstable at high temperature for a long time, prone to side reactions such as oxidation and polymerization, which affect the quality and yield of products, and also increase the difficulty of separation

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] At 15 °C, add 500 mg linoleic acid and 30 mg lipoxygenase (enzyme activity: 8000 U / mg) into 500 mL, pH 8, 0.02 M sodium borate aqueous solution in turn, stir and mix thoroughly, and pass through 30 μM O 2 Keep it for 2 min, then pass N 2 until the oxygen concentration is 0. After the reaction continued for 1.5 h, the pH of the reaction solution was adjusted to 3.5 with 2 M hydrochloric acid solution, and the crude product was extracted 3 times with diethyl ether immediately, the combined extracts were washed with saturated brine, anhydrous magnesium sulfate was added to remove water, and finally 2 The extractant ether was removed from the stream to obtain dimer acid, and the yield of dimer acid was 41.3%.

Embodiment 2

[0014] At 30 °C, add 500 μM methyl linoleate and 15 mg lipoxygenase (enzyme activity: 8000 U / mg) into 250 mL, pH 6.6, 0.02 M sodium hydrogen phosphate buffer, stir well After that, 25 mL of oxygen was passed through for 15 min, and then N 2 until the oxygen concentration is 0. After the reaction continued for 2.5 h, the pH of the reaction solution was adjusted to 3.5 with 2 M sulfuric acid, and immediately washed with n-hexane / ether ( V : V =7:2) extract the crude product 3 times, combine the extracts and wash with saturated brine, add anhydrous magnesium sulfate to remove water, and finally in N 2 The extractant was removed from the stream to obtain dimer acid, and the yield of dimer acid was 36.8%.

Embodiment 3

[0016] At 25 °C, 200 μM arachidonic acid and 15 mg lipoxygenase were sequentially added to 300 mL, pH 9, 0.02 M sodium borate buffer, stirred thoroughly and then passed through 65 μM O 2 Keep for 5 min, then pass N 2 until the oxygen concentration is 0. After the reaction continued for 2 h, the pH of the reaction solution was adjusted to 3.5 with 1 M hydrochloric acid, and immediately washed with n-hexane / diethyl ether ( V : V =7:5) extract the crude product 3 times, combine the extracts and wash with saturated brine, add magnesium sulfate to remove water, and finally in N 2 The extractant was removed from the stream to obtain dimer acid, and the yield of dimer acid was 39.2%.

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Abstract

The invention discloses a method for synthesizing dimeric acid by a lipoxygenase one-step process. The method provided by the invention comprises the following steps: adding unsaturated fatty acid or its ester and lipoxygenase with stirring into a buffer system with pH 6-10 at the temperature of 0-35 DEG C, allowing oxygen to enter after uniform stirring so as to trigger an hydroperoxidation reaction, keeping for 1-15 min, allowing N2 to enter so as to make the oxygen concentration to be reduced to 0, reacting for 1-2.5 hours, using sulfuric acid or hydrochloric acid solution to adjust pH of a reaction solution to 3.5 so as to end the reaction, using an extractant to make a mixture react, merging extracts and washing by the use of saturated salt water, adding anhydrous magnesium sulfate to remove moisture, and finally removing the extractant in the flow of N2 so as to obtain dimeric acid. Under a green mild condition, dimeric acid is synthesized in an aqueous phase by a one-step enzymic method. Thus, preparation conditions of dimeric acid are improved, and a new idea is also provided for the preparation of dimeric acid.

Description

technical field [0001] The invention relates to a method for synthesizing dimer acid. Background technique [0002] Dimer acid is a compound formed by intermolecular polymerization of octadecadienoic acid and its esters. Dimer acid is a chemical with special physical and chemical properties and a wide range of industrial uses. In the production of inks, coatings, adhesives, lubricants, and surfactants, it plays an increasingly important role. At present, the relatively mature and commonly used methods for producing dimer acid are thermal dimerization method and clay method, both of which require high temperature and high pressure, and the reaction conditions are relatively harsh. Unsaturated fatty acids become very unstable at high temperature for a long time, and are prone to side reactions such as oxidation and polymerization, which affect the quality and yield of products and increase the difficulty of separation. Contents of the invention [0003] The purpose of the...

Claims

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Application Information

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IPC IPC(8): C12P7/64
Inventor 蔡燕沈洁周红波朱金丽
Owner NANTONG UNIVERSITY
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