CN111187165B - Method for continuously preparing allyl ester by using microchannel reaction device - Google Patents
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- C07—ORGANIC CHEMISTRY
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
- C07C67/40—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester by oxidation of primary alcohols
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- B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
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- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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Abstract
The invention provides a method for continuously preparing allyl ester by using a microchannel reaction device, which uses benzylTaking alcohol I and cyclohexene II as reaction raw materials, continuously reacting in a microchannel reaction device in the presence of a catalyst, an oxidant and a solvent, and obtaining allyl ester III through free radical cross-coupling reaction; wherein the reaction process is shown as the reaction formula:
the method for preparing the allyl ester by the reaction has the advantages of simple, convenient, safe and efficient process operation and mild reaction conditions.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a method for continuously preparing allyl ester by using a microchannel reaction device.
Background
Allyl esters are multifunctional building blocks, have wide application in synthesis, and are important ubiquitous core frameworks in many natural products, pharmaceutical molecules and fine chemicals, thus attracting attention of many researchers.
Currently, allyl esters are prepared mainly by: (1) the allyl esters are synthesized by copper-catalyzed oxidative coupling of acids, cycloalkanes, as described in the literature (chem.commun.,2015,51, 2361); (2) the acid and the cycloolefine are subjected to catalytic oxidative coupling by copper-aluminum composite metal to synthesize allyl ester, which can be seen in the literature (org.Lett.2014,16, 1598-1601); (3) the allyl ester is prepared by the reaction of perester and cyclohexene under the catalysis of copper, which can be seen in the literature (adv.synth.Catal.2008, 350, 2639-; (4) the allyl ester is synthesized by the aldehyde and the cycloalkane through the catalytic oxidation coupling of copper, which can be seen in the literature (org. Lett.2014,16, 2530-2533). Although the existing routes for preparing allyl esters are numerous, most of the methods use transition metals, and the reaction conditions are complex, the reaction time is long, and the industrial application of the allyl esters is limited.
Disclosure of Invention
In order to overcome the problems of long reaction flow period and metal catalysis requirement of the traditional oxidation system, the invention provides a method for continuously preparing allyl ester by using a microchannel reaction device, wherein benzyl alcohol I and cyclohexene II are used as reaction raw materials and are continuously reacted in the microchannel reaction device to obtain allyl ester III; the reaction comprises the following steps:
(1) dissolving a compound I and a catalyst in a solvent to obtain a homogeneous solution A; dissolving a compound II and an oxidant in a solvent to obtain a homogeneous phase solution B;
(2) pumping the homogeneous solutions A and B obtained in the step (1) into a micro mixer in a micro-channel reaction device respectively, mixing, and injecting into a micro-channel reactor for reaction, wherein the reaction equation is as follows:
(3) and collecting the reaction liquid flowing out of the microchannel reactor to obtain the compound III.
Preferably, in the step (1), the catalyst is any one or more of iodine, N-iodosuccinimide, tetraethylammonium iodide, tetrabutylammonium iodide and tetrabutylammonium bromide.
Preferably, in the step (1), the oxidant is any one or more of tert-butyl hydroperoxide, hydrogen peroxide, tert-butyl peroxybenzoate, potassium persulfate and di-tert-butyl peroxide; the solvent is one or more of acetonitrile, dimethyl sulfoxide, dioxane, N, N-dimethylformamide and dichloroethane.
Preferably, in the step (1), the concentration of the compound I in the homogeneous solution A is 0.05 mmol/mL-0.2 mmol/mL; the concentration of the catalyst in the homogeneous solution A is 0.01 mmol/mL-0.04 mmol/mL; the concentration of the compound II in the homogeneous solution B is 0.1 mmol/mL-0.4 mmol/mL; the concentration of the oxidant in the homogeneous solution B is 0.1 mmol/mL-0.6 mmol/mL.
Preferably, in the step (2), the molar ratio of the compound I, the catalyst, the compound II and the oxidant in the homogeneous solutions a and B in the micromixer is 1: (0.1-0.4): (1-4): (1-6).
Preferably, in the step (2), the flow rate of the homogeneous solutions A and B pumped into the microchannel reaction device is 0.2 ml/min-0.8 ml/min; the temperature of the reaction is 60-120 ℃.
Preferably, the microchannel reaction device comprises a pump A, a pump B, a micromixer, a microchannel reactor and a receiver, wherein the pump A and the pump B are connected to the micromixer in a parallel manner, and the micromixer, the microchannel reactor and the receiver are connected in a series manner, and the connection is realized through a pipeline.
Preferably, the reaction volume of the microchannel reactor is 5ml to 10ml, and the inner diameter of the coil of the microchannel reactor is 0.5mm to 1 mm.
The microchannel reactor technology has gradually become a research hotspot in the technical field of international fine chemical engineering. A microchannel reactor is a three-dimensional structural element that can be used for chemical reactions, fabricated with a fixed matrix by means of special microfabrication techniques. Microchannel reactors typically contain very small channel sizes (equivalent diameters less than 500 μm) and channel diversity in which fluids flow, mix, and react. And therefore have a very large specific surface area (surface area/volume) in such a micro-structured chemical device. The advantages brought by this are the great mass and heat transfer efficiency, i.e. the precise control of the reaction temperature and the instantaneous mixing of the reaction mass in a precise ratio can be realized. These are all key to improving yield, selectivity, safety, and product quality.
The microchannel reactor used in the invention is a microchannel reactor with small channel diameter and high heat transfer efficiency. The allyl ester is quickly synthesized by using the microchannel reactor, so that the yield is greatly improved, side reactions are reduced, amplification reaction is facilitated, and the reaction process is safe, efficient and simple.
Has the advantages that: the invention adopts a microchannel reaction device, shortens the reaction time from the traditional dozens of hours to dozens of minutes, has higher product yield and obviously improves the reaction efficiency; the method does not need to add a metal catalyst, is simple and convenient to operate and has low cost; the invention continuously reacts through the injection pump and the microchannel reaction device, the preparation process is easy to operate and control, the safety is high, the reaction condition is mild, and the invention has better industrial amplification potential.
Drawings
FIG. 1 is a schematic structural diagram of a microchannel reactor apparatus according to the present invention.
Detailed Description
The invention will be better understood by reference to the following examples in conjunction with the accompanying drawings. However, those skilled in the art will readily appreciate that the description of the embodiments is only for illustrating the present invention and should not be taken as limiting the invention as detailed in the claims.
Using the apparatus diagram of fig. 1, the following steps are followed: (1) respectively adding the solution A and the solution B which are prepared in proportion into injection pumps a and B; (2) injecting the mixture into a microchannel reaction device by an injection pump according to a certain proportion for mixing and reacting; (3) the reaction temperature of the microchannel reactor is controlled by an oil bath pan; (4) collecting the effluent reaction liquid, adding saturated sodium thiosulfate for quenching, adding ethyl acetate for extraction and separation, and calculating the product yield by an HPLC method; and measuring the product yield by a high performance liquid chromatography, and separating by column chromatography to obtain the target product.
Example 1 synthesis of compound III:
dissolving 1mmol (0.108g) of benzyl alcohol and 0.2mmol (0.051g) of iodine in 10mL of acetonitrile to obtain a homogeneous solution A, and adding the homogeneous solution A into a syringe pump a; 2mmol (0.164g) cyclohexene and 3mmol TBHP (70%, 0.386g) (tert-butyl hydroperoxide) were dissolved in 10mL acetonitrile to give a homogeneous solution B which was added to syringe pump B; the injection flow rates of the injection pumps a and b are both 0.4 ml/min; the reaction volume V of the microchannel reactor is 10ml, and the reaction time is 12.5 min; the inner diameter of the micro-channel reactor is 0.5 mm; the temperature of the microchannel reactor is 100 ℃; after one period of reaction in the microchannel reactor, collecting reaction liquid, calculating the product yield to be 78% by an HPLC method, and obtaining the product III after column chromatography separation.
1H NMR(400MHz,CDCl3)δ8.01(d,J＝8.0Hz,2H),6.91(d,J＝8.0Hz,2H),5.99(t,J＝10.0Hz,1H),5.83(d,J＝10.0Hz,1H),5.48(s,1H),3.38(s,3H),2.16-1.70(m,6H)；13C NMR(100MHz,CDCl3)δ166.0,163.2,132.6,131.6,125.9,123.1,113.4,68.2,55.4,28.2,24.9,19.0.HRMS(TOF)m/z[M+H]+Calcd for C13H15O2 203.1067found 203.1064.
Example 2 synthesis of compound III:
dissolving 1mmol (0.108g) of benzyl alcohol and 0.2mmol (0.051g) of iodine in 10mL of dimethyl sulfoxide to obtain a homogeneous solution A, and adding the homogeneous solution A into a syringe pump a; 2mmol (0.164g) cyclohexene and 3mmol TBHP (70%, 0.386g) (tert-butyl hydroperoxide) were dissolved in 10mL dimethyl sulfoxide to give a homogeneous solution B which was added to syringe pump B; the injection flow rates of the injection pumps a and b are both 0.4 ml/min; the reaction volume V of the microchannel reactor is 10ml, and the reaction time is 12.5 min; the inner diameter of the micro-channel reactor is 0.5 mm; the temperature of the microchannel reactor is 100 ℃; after one period of reaction in the microchannel reactor, collecting reaction liquid, calculating the product yield to be 76% by an HPLC method, and obtaining the product III after column chromatography separation.
Example 3 synthesis of compound III:
dissolving 1mmol (0.108g) of benzyl alcohol and 0.2mmol (0.051g) of iodine in 10mL of N, N-dimethylformamide to obtain a homogeneous solution A, and adding the homogeneous solution A into a syringe pump a; 2mmol (0.164g) cyclohexene and 3mmol TBHP (70%, 0.386g) (tert-butyl hydroperoxide) were dissolved in 10mL N, N dimethylformamide to give a homogeneous solution B which was added to syringe pump B; the injection flow rates of the injection pumps a and b are both 0.4 ml/min; the reaction volume V of the microchannel reactor is 10ml, and the reaction time is 12.5 min; the inner diameter of the micro-channel reactor is 0.5 mm; the temperature of the microchannel reactor is 100 ℃; after one period of reaction in the microchannel reactor, collecting reaction liquid, calculating the product yield to be 85% by an HPLC method, and obtaining the product III after column chromatography separation.
Example 4 synthesis of compound III:
dissolving 1mmol (0.108g) of benzyl alcohol and 0.1mmol (0.025g) of iodine in 10mL of N, N-dimethylformamide to obtain a homogeneous solution A, and adding the homogeneous solution A into a syringe pump a; 2mmol (0.164g) cyclohexene and 3mmol TBHP (70%, 0.386g) (tert-butyl hydroperoxide) were dissolved in 10mL N, N dimethylformamide to give a homogeneous solution B which was added to syringe pump B; the injection flow rates of the injection pumps a and b are both 0.4 ml/min; the reaction volume V of the microchannel reactor is 10ml, and the reaction time is 12.5 min; the inner diameter of the micro-channel reactor is 0.5 mm; the temperature of the microchannel reactor is 100 ℃; after one period of reaction in the microchannel reactor, collecting reaction liquid, calculating the product yield to 73% by an HPLC method, and obtaining the product III after column chromatography separation.
Example 5 synthesis of compound III:
dissolving 1mmol (0.108g) of benzyl alcohol and 0.2mmol (0.051g) of iodine in 10mL of N, N-dimethylformamide to obtain a homogeneous solution A, and adding the homogeneous solution A into a syringe pump a; 3mmol (0.246g) cyclohexene and 3mmol TBHP (70%, 0.386g) (tert-butyl hydroperoxide) were dissolved in 10mL N, N dimethylformamide to give a homogeneous solution B which was added to syringe pump B; the injection flow rates of the injection pumps a and b are both 0.4 ml/min; the reaction volume V of the microchannel reactor is 10ml, and the reaction time is 12.5 min; the inner diameter of the micro-channel reactor is 0.5 mm; the temperature of the microchannel reactor is 100 ℃; after one period of reaction in the microchannel reactor, collecting reaction liquid, calculating the product yield by an HPLC method to be 83%, and obtaining the product III after column chromatography separation.
Example 6 synthesis of compound III:
dissolving 1mmol (0.108g) of benzyl alcohol and 0.2mmol (0.051g) of iodine in 10mL of N, N-dimethylformamide to obtain a homogeneous solution A, and adding the homogeneous solution A into a syringe pump a; 1mmol (0.082g) cyclohexene and 3mmol TBHP (70%, 0.386g) (tert-butyl hydroperoxide) were dissolved in 10mL N, N dimethylformamide to give a homogeneous solution B, which was added to syringe pump B; the injection flow rates of the injection pumps a and b are both 0.4 ml/min; the reaction volume V of the microchannel reactor is 10ml, and the reaction time is 12.5 min; the inner diameter of the micro-channel reactor is 0.5 mm; the temperature of the microchannel reactor is 100 ℃; after one period of reaction in the microchannel reactor, collecting reaction liquid, calculating the product yield to be 69% by an HPLC method, and obtaining the product III after column chromatography separation.
Example 7 synthesis of compound III:
dissolving 1mmol (0.108g) of benzyl alcohol and 0.2mmol (0.051g) of iodine in 10mL of N, N-dimethylformamide to obtain a homogeneous solution A, and adding the homogeneous solution A into a syringe pump a; 2mmol (0.164g) cyclohexene and 4mmol TBHP (70%, 0.514g) (tert-butyl hydroperoxide) were dissolved in 10mL N, N dimethylformamide to give a homogeneous solution B which was added to syringe pump B; the injection flow rates of the injection pumps a and b are both 0.4 ml/min; the reaction volume V of the microchannel reactor is 10ml, and the reaction time is 12.5 min; the inner diameter of the micro-channel reactor is 0.5 mm; the temperature of the microchannel reactor is 100 ℃; after one period of reaction in the microchannel reactor, collecting reaction liquid, calculating the product yield by an HPLC method to be 84%, and obtaining the product III after column chromatography separation.
Example 8 synthesis of compound III:
dissolving 1mmol (0.108g) of benzyl alcohol and 0.2mmol (0.051g) of iodine in 10mL of N, N-dimethylformamide to obtain a homogeneous solution A, and adding the homogeneous solution A into a syringe pump a; 2mmol (0.164g) cyclohexene and 2mmol TBHP (70%, 0.267g) (tert-butyl hydroperoxide) were dissolved in 10mL N, N dimethylformamide to give a homogeneous solution B which was added to syringe pump B; the injection flow rates of the injection pumps a and b are both 0.4 ml/min; the reaction volume V of the microchannel reactor is 10ml, and the reaction time is 12.5 min; the inner diameter of the micro-channel reactor is 0.5 mm; the temperature of the microchannel reactor is 100 ℃; after one period of reaction in the microchannel reactor, collecting reaction liquid, calculating the product yield to 73% by an HPLC method, and obtaining the product III after column chromatography separation.
Example 9 synthesis of compound III:
dissolving 1mmol (0.108g) of benzyl alcohol and 0.2mmol (0.051g) of iodine in 10mL of N, N-dimethylformamide to obtain a homogeneous solution A, and adding the homogeneous solution A into a syringe pump a; 2mmol (0.164g) cyclohexene and 3mmol TBHP (70%, 0.386g) (tert-butyl hydroperoxide) were dissolved in 10mL N, N dimethylformamide to give a homogeneous solution B which was added to syringe pump B; the injection flow rates of the injection pumps a and b are both 0.6 ml/min; the reaction volume V of the microchannel reactor is 10ml, and the reaction time is 8.3 min; the inner diameter of the micro-channel reactor is 0.5 mm; the temperature of the microchannel reactor is 100 ℃; after one period of reaction in the microchannel reactor, collecting reaction liquid, calculating the product yield to be 80% by an HPLC method, and obtaining the product III after column chromatography separation.
Example 10 synthesis of compound III:
dissolving 1mmol (0.108g) of benzyl alcohol and 0.2mmol (0.051g) of iodine in 10mL of N, N-dimethylformamide to obtain a homogeneous solution A, and adding the homogeneous solution A into a syringe pump a; 2mmol (0.164g) cyclohexene and 3mmol TBHP (70%, 0.386g) (tert-butyl hydroperoxide) were dissolved in 10mL N, N dimethylformamide to give a homogeneous solution B which was added to syringe pump B; the injection flow rates of the injection pumps a and b are both 0.4 ml/min; the reaction volume V of the microchannel reactor is 10ml, and the reaction time is 12.5 min; the inner diameter of the micro-channel reactor is 0.5 mm; the temperature of the microchannel reactor is 80 ℃; after one period of reaction in the microchannel reactor, collecting reaction liquid, calculating the product yield to be 77% by an HPLC method, and obtaining the product III after column chromatography separation.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent should be subject to the appended claims.
Claims (7)
1. A method for continuously preparing allyl ester by using a microchannel reaction device is characterized by comprising the following steps: taking benzyl alcohol I and cyclohexene II as reaction raw materials, and continuously reacting in a microchannel reaction device to obtain allyl ester III; the reaction comprises the following steps:
(1) dissolving a compound I and a catalyst in a solvent to obtain a homogeneous solution A; dissolving a compound II and an oxidant in a solvent to obtain a homogeneous phase solution B;
wherein the content of the first and second substances,
the catalyst is one or more of iodine, N-iodosuccinimide, tetraethylammonium iodide, tetrabutylammonium iodide and tetrabutylammonium bromide;
the oxidant is any one or more of tert-butyl hydroperoxide, hydrogen peroxide, tert-butyl peroxybenzoate, potassium persulfate and di-tert-butyl peroxide;
(2) respectively pumping the homogeneous solutions A and B obtained in the step (1) into a micro mixer in a micro-channel reaction device, mixing, and injecting into a micro-channel reactor for reaction, wherein the reaction equation is as follows:
(3) and collecting the reaction liquid flowing out of the microchannel reactor to obtain the compound III.
2. The process for continuously producing allyl esters using a microchannel reaction apparatus as set forth in claim 1, characterized in that: in the step (1), the solvent is one or more of acetonitrile, dimethyl sulfoxide, dioxane, N, N-dimethylformamide and dichloroethane.
3. The process for continuously producing allyl esters using a microchannel reaction apparatus as set forth in claim 1, characterized in that: in the step (1), the concentration of the compound I in the homogeneous solution A is 0.05 mmol/mL-0.2 mmol/mL; the concentration of the catalyst in the homogeneous solution A is 0.01 mmol/mL-0.04 mmol/mL; the concentration of the compound II in the homogeneous solution B is 0.1 mmol/mL-0.4 mmol/mL; the concentration of the oxidant in the homogeneous solution B is 0.1 mmol/mL-0.6 mmol/mL.
4. The process for continuously producing allyl esters using a microchannel reaction apparatus as set forth in claim 1, characterized in that: in the step (2), in the homogeneous solutions a and B in the micromixer, the molar ratio of the compound I, the catalyst, the compound II, and the oxidant is 1: (0.1-0.4): (1-4): (1-6).
5. The process for continuously producing allyl esters using a microchannel reaction apparatus as set forth in claim 1, characterized in that: in the step (2), the flow rate of the homogeneous solutions A and B pumped into the microchannel reaction device is 0.2 ml/min-0.8 ml/min; the reaction temperature is 60-120 ℃.
6. The process for continuously producing allyl esters using a microchannel reaction apparatus as set forth in any one of claims 1 to 5, wherein: the microchannel reaction device comprises a pump A, a pump B, a micromixer, a microchannel reactor and a receiver, wherein the pump A and the pump B are connected to the micromixer in a parallel mode, the micromixer, the microchannel reactor and the receiver are connected in a series mode, and the connection is realized through a pipeline.
7. The process of claim 6 wherein the microchannel reactor has a reaction volume of 5ml to 10ml and a coil internal diameter of 0.5mm to 1 mm.
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| DE69510731T2 (en) * | 1994-06-01 | 2000-02-03 | Firmenich & Cie | Process for the preparation of allyl alcohol derived carboxylic acid esters |
| WO2002072644A1 (en) * | 2001-03-12 | 2002-09-19 | Zeria Pharmaceutical Co., Ltd. | Solid-phase-supported transition metal catalysts |
| CN102603523A (en) * | 2012-03-23 | 2012-07-25 | 苏州大学 | Preparation method of allyl esters |
| CN103819341A (en) * | 2014-01-26 | 2014-05-28 | 台州学院 | Method for preparing allyl ester and benzyl ester compounds |
| CN107266311B (en) * | 2017-03-24 | 2020-07-28 | 南京工业大学 | Method for continuously preparing α -keto ester by using microfluid chip reactor |
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