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Preparation method of lipase isomer Vc mixed fatty acid ester

A technology for mixing fatty acid esters and lipase, which is applied in the field of preparation of iso-Vc mixed fatty acid esters catalyzed by lipase, and can solve the problems of synthesizing iso-Vc mixed fatty acid esters, complicated synthesis, separation and purification processes, etc.

Active Publication Date: 2013-12-25
江西省德兴市百勤异VC钠有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, animal and vegetable oils have rich nutritional value to the human body. In the Chinese invention patent application number 201010224746.2 and "Process Conditions for Synthesizing L-Ascorbic Fatty Acid Ester from Lard Catalyzed by Lipase" (Food Science, Volume 31, No. 18, 2010) Issue pp. 134-138), "Synthesis of mixed esters of ascorbic acid using methyl esters of palm and soybean oils" (Preparative Biochemistry & Biotechnology, 2005, 35(2): 113-118) and other papers, published or reported Utilize lard, palm oil and soybean oil to synthesize the method for Vc mixed fatty acid ester under the catalysis of lipase, they involve first corresponding oil and methanol generation transesterification generation mixed fatty acid methyl ester, then utilize Vc and mixed fatty acid methyl ester Vc mixed fatty acid esters are prepared by transesterification, and the synthesis, separation and purification process is more complicated
So far, there is no relevant report on the direct utilization of animal and vegetable oils to synthesize iso-Vc mixed fatty acid esters

Method used

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  • Preparation method of lipase isomer Vc mixed fatty acid ester
  • Preparation method of lipase isomer Vc mixed fatty acid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In an Erlenmeyer flask with stopper, add 3.52 g (20 mmol) of iso-Vc, 24.0 g of fresh camellia oil, 0.70 g of Lipozyme 435 lipase, and 80 mL of tert-butanol. Place it in a constant temperature shaker, fix the reaction temperature at 55°C, shake The bed speed is 180 rpm, and the reaction time is 30 h.

[0021] At the end of the reaction, filter to remove lipase and unreacted iso-Vc, rotate to remove tert-butanol, add ethyl acetate (80 mL) and distilled water (80 mL), stir and mix thoroughly, separate the ethyl acetate layer. The ethyl acetate layer was continuously washed with distilled water to remove iso-Vc (washed until no iso-Vc exists in the water layer), then dried with anhydrous sodium sulfate, and then distilled under reduced pressure to remove ethyl acetate to obtain a crude product of 25.7 g.

[0022] Measure about 200 mL silica gel and pack the column with petroleum ether wet method. After the crude product is directly applied to the column, slowly elute the silica ...

Embodiment 2

[0027] In an Erlenmeyer flask with stopper, add 3.52 g (20 mmol) of iso-Vc, 7.1 g of fresh camellia oil, 0.18 g of Lipozyme 435 lipase, and 80 mL of tert-butanol. Place them in a constant temperature shaker, fix the reaction temperature at 20°C, shake The bed rotation speed was 180 rpm, and the reaction time was 5 hours.

[0028] At the end of the reaction, filter to remove lipase, rotary evaporation to remove tert-butanol, add ethyl acetate (80 mL) and distilled water (80 mL), stir and mix thoroughly, separate the ethyl acetate layer. The separated ethyl acetate layer was continuously washed with distilled water to remove iso-Vc (washed until no iso-Vc exists in the water layer), and then dried with anhydrous sodium sulfate. After ethyl acetate was distilled off under reduced pressure, 9.4 g of crude product was obtained.

[0029] Measure about 90 mL silica gel and pack the column with petroleum ether wet method. After the crude product is directly applied to the column, slowly e...

Embodiment 3

[0032] In an Erlenmeyer flask with stopper, add 1.76 g (10 mmol) of iso-Vc, 26.4 g of fresh camellia oil, 0.27 g of Lipozyme 435 lipase, and 40 mL of tert-amyl alcohol. Place them in a constant temperature shaker, fix the reaction temperature at 65°C, shake The bed speed was 180 rpm, and the reaction time was 36 h.

[0033] At the end of the reaction, filter to remove lipase and rotary evaporation to remove tert-amyl alcohol, add ethyl acetate (80 mL) and distilled water (40 mL), stir and mix thoroughly, separate the ethyl acetate layer. The separated ethyl acetate layer was continuously washed with distilled water to remove iso-Vc (washed until no iso-Vc exists in the water layer), and then dried with anhydrous sodium sulfate. After ethyl acetate was distilled off under reduced pressure, 25.8 g of a crude product was obtained.

[0034] Measure about 200 mL silica gel and pack the column with petroleum ether wet method. After the crude product is directly applied to the column, sl...

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Abstract

The invention provides a preparation method of lipase isomer Vc mixed fatty acid ester, and the preparation method comprises the following steps of: in the presence of lipozyme 435 lipase, enabling isomer Vc and animal and vegetable oil to have transesterification; filtering after the reaction, removing lipase and the isomer Vc which does not react; carrying out reduced pressure distillation on filtrate, removing an organic solvent, adding ethyl acetate and water into the filtrate, and further removing the isomer Vc which does not react; drying an ethyl acetate layer by anhydrous sodium sulfate, carrying out reduced pressure distillation, and removing the ethyl acetate; and finally, separating and purifying by column chromatography, thus obtaining waxy solid. The highest transformation rate of the isomer Vc is up to 48%, and the unreacted animal and vegetable oil can be recycled. The preparation method is simple and convenient in operation and accords with the requirements of environmental friendliness.

Description

technical field [0001] The invention relates to a preparation method of lipase-catalyzed iso-Vc mixed fatty acid ester, which belongs to the field of biocatalysis and fine chemical industry. Background technique [0002] Different Vc (D-isoascorbic acid) and Vc (L-ascorbic acid) are isomers. Because iso-Vc is oxidized faster than Vc, the market share of iso-Vc as an antioxidant is increasing. However, both iso-Vc and Vc are water-soluble, and it is difficult to be used as an antioxidant for the preservation of fat-soluble foods. In order to overcome this shortcoming and expand its application range as an antioxidant, many scholars have chemically modified iso-Vc and Vc to derivate them into higher fatty acid esters or higher fatty aldehyde acetals, especially higher fatty acid esters . [0003] The derivation of iso-Vc or Vc into higher fatty acid esters can be done by chemical synthesis or biological enzyme catalysis. The chemical synthesis method has many side reaction...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P7/64
Inventor 郑大贵周强余泗莲祝显红余彬彭化南
Owner 江西省德兴市百勤异VC钠有限公司