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Sandwich-type microreactor and application thereof in enzymatic synthesis of caffeic acid phenethyl ester

A technology of phenethyl caffeate and microreactor, which is applied in chemical instruments and methods, chemical/physical/physicochemical processes, chemical/physical processes, etc., can solve the problem of unreported phenethyl caffeate and reactor volume Large, complex product components and other issues, to achieve good industrial application prospects, enhance mass transfer, improve the effect of reaction efficiency

Active Publication Date: 2013-12-18
JIANGSU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The continuous reaction replaces the batch reaction, the reaction conditions are easy to control, and it helps to overcome and solve the problems of large reactor volume, low catalytic selectivity and complex product components in traditional synthesis (Angew.Chem.Int.Edit, 2012, 51 ,1706-1709)
Up to now, the enzymatic synthesis of phenethyl caffeate using microreactors has not been reported

Method used

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  • Sandwich-type microreactor and application thereof in enzymatic synthesis of caffeic acid phenethyl ester
  • Sandwich-type microreactor and application thereof in enzymatic synthesis of caffeic acid phenethyl ester
  • Sandwich-type microreactor and application thereof in enzymatic synthesis of caffeic acid phenethyl ester

Examples

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Effect test

Embodiment 1

[0032]A sandwich microreactor, including a syringe pump 1 and a reactor body, the material of the reactor body is polydimethylsiloxane (polydimethylsiloxane), and is composed of a reaction plate 2 and a cover plate 3. load area 4. A fixing clip is arranged between the reaction plate and the cover plate.

[0033] The dimensions of the immobilized area were 1 cm wide, 500 μm deep, and 50 mm long, and Novozym 435 (60 mg) was filled into the microchannel. Dissolve 0.1 mg of methyl caffeate in 1 mL of [Hmim][PF 6 ] In the ionic liquid, a reaction system was formed according to the molar ratio of methyl caffeate and phenylethyl alcohol at 1:1. The prepared reaction system was injected into the microreactor through a micro-injection pump at a flow rate of 100 μL / min (retention time of 3 min), and the temperature was controlled at 30°C. The export material was collected, and the yield of phenethyl caffeate synthesized by enzymatic transesterification was detected by HPLC to be 1.5%...

Embodiment 2

[0035] The structure of the device was as in Example 1, wherein the size of the immobilized region was 1 cm wide, 500 μm deep, and 200 mm long, and Novozym435 (240 mg) was filled into the microchannel. Take 40 mg of methyl caffeate and dissolve it in 1 mL of [Omim][Cl] ionic liquid, and form a reaction system according to the molar ratio of methyl caffeate to phenylethyl alcohol of 1:100. The prepared reaction system was injected into the microreactor through a microsyringe pump at a flow rate of 2 μL / min (retention time of 2.5 h), and the temperature was controlled at 80° C. The export material was collected, and the yield of caffeic acid phenethyl ester by enzymatic transesterification was detected by HPLC to be 21.3%.

Embodiment 3

[0037] The structure of the device was as in Example 1, wherein the size of the immobilized region was 1 cm wide, 500 μm deep, and 100 mm long, and Novozym435 (120 mg) was filled into the microchannel. Dissolve 10 mg of methyl caffeate in 1 mL of [TOMA][CF 3 SO 3 ] In the ionic liquid, the reaction system was formulated according to the molar ratio of methyl caffeate and phenylethyl alcohol of 1:50. The prepared reaction system was injected into the microreactor through a micro-injection pump, the flow rate was 20 μL / min (retention time was 15 min), and the temperature was controlled at 60°C. The export material was collected, and the yield of phenethyl caffeate synthesized by enzymatic transesterification was detected by HPLC as 32.8%.

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Abstract

The invention discloses a sandwich-type microreactor and an application thereof in enzymatic synthesis of caffeic acid phenethyl ester. According to the sandwich-type microreactor disclosed by the invention, lipase Novozym435 is filled into the sandwich-type microreactor and ionic liquid containing caffeic acid methyl ester and phenethyl alcohol as substrates is injected into the microreactor through a micro-injection pump so as to carry out transesterification to prepare caffeic acid phenethyl ester (at 60 DEG C, a flow velocity is 2mu l / min, and when retention time is 2.5 hours, yield is up to 99.5%). The method for preparing the caffeic acid phenethyl ester is simple and convenient to operate, moderate in reaction condition, high in product yield and environment-friendly. According to the sandwich-type microreactor and the application thereof, the shortcomings of a conventional batch reactor which is long in reaction duration, low in synthesis efficiency and the like are overcome, and large-scale preparation of the caffeic acid phenethyl ester is facilitated.

Description

technical field [0001] The invention relates to the field of biochemical pharmacy, in particular to a sandwich microreactor and its application in enzymatically synthesizing phenethyl caffeate. Background technique [0002] Caffeic acid phenethyl ester, English name: Caffeic acid phenethyl ester (CAPE), chemical name: 2-phenylethyl-3-(3,4-dihydroxyphenyl)-2-acrylate, molecular formula: C 17 h 16 o 4 , molecular weight: 284.31. Caffeic acid phenethyl ester is the main functional ingredient in natural products such as propolis and rhodiola rosea. It has been proved by pharmacological experiments that it can block the production of active oxidative substances in neutrophils, block the xanthine oxidase system, and inhibit the The increase of internal NO can also inhibit the proliferation of tumor cells (Biol.Pharm.Bull, 2003, 26(4):487-491), and it is an auxiliary drug or active ingredient of drugs that major international pharmaceutical companies are competing to develop. ...

Claims

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Application Information

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IPC IPC(8): B01J19/00C12P7/62
Inventor 王俊顾双双崔红生魏贤彬吴福安
Owner JIANGSU UNIV OF SCI & TECH
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