CN111217769B - A kind of method utilizing nano-alumina to catalyze olefin epoxidation to synthesize epoxy compound - Google Patents

Abstract

The invention belongs to the field of organic synthesis and catalysis, and discloses a method for synthesizing epoxy compounds by catalyzing epoxidation of olefins with nano-alumina. The method comprises the following steps: adding solvent, olefin, nano-alumina and aliphatic aldehyde into a reactor to obtain a mixed liquid, in which the olefin is used as a raw material, the nano-alumina is used as a catalyst, and the aliphatic aldehyde is used as a reducing agent, and the reaction vessel is evacuated Afterwards, oxygen is introduced, heated and stirred for reaction, and a reaction solution is obtained after the reaction is completed, and the reaction solution is separated and purified to obtain the epoxy compound. The catalyst used in the method of the invention is cheap and easy to obtain, has mild reaction conditions, wide applicability to substrates, safe and simple operation, and has potential industrial application prospects.

Description

A kind of method utilizing nano-alumina to catalyze olefin epoxidation to synthesize epoxy compound

technical field

The invention belongs to the field of organic synthesis and catalysis, and in particular relates to a method for synthesizing epoxy compounds by catalyzing epoxidation of olefins with nano-alumina.

Background technique

The epoxidation of olefins is a very important oxidation reaction because the resulting epoxy compounds are widely used in the production of chemicals such as epoxy resins, coatings, and surfactants. In addition, epoxy compounds are also an important class of organic synthesis intermediates. For example, a series of functional molecules can be obtained through the nucleophilic ring-opening reaction of epoxy compounds, which can be used to further synthesize chemicals such as pharmaceutical molecules, pesticides, and spices. Therefore, it is of great significance to develop efficient catalysts to realize selective epoxidation of olefins (Q.H.Xia, H.Q.Ge, C.P.Ye, Z.M.Liu, K.X.Su, Chem.Rev.2005, 105, 1603–1662; O.A.Wong , Y.Shi, Chem.Rev.2008, 108, 3958–3987; K.P.Bryliakov, Chem.Rev.2017, 117, 11406-11459; W.Yan, G.Zhang, H.Yan, Y.Liu, X. Chen, X. Feng, X. Jin, C. Yang, ACS Sustainable Chem. Eng. 2018, 6, 4423-4452; Y. Zhu, Q. Wang, R. G. Cornwall, Y. Shi, Chem. Rev. 2014, 114 , 8199-8256).

A.B.

O.A.Kholdeeva,J.Catal.2007,246,241–248)、铜(Y.Qi,Y.Luan,J.Yu,X.Peng,G.Wang,Chem.Eur.J.2015,21,1589–1597；G.Yang,H.Du,J.Liu,Z.Zhou,X.Hu,Z.Zhang,Green Chem.,2017,19,675-681)、钯(X.He,L.Chen,X.Zhou,H.Ji,Catal.Commun.2016,83,78–81)、钌(P.Mekrattanachai,J.Liu,Z.Li,C.Cao,W.Song,Chem.Commun.2018,54,1433–1436)等等被报道用于烯烃的氧气环氧化反应。而为了便于催化剂与产物的分离以及催化剂的回收再利用，发展高效的非均相催化剂尤其重要。例如，Wang等人发现利用铜金属有机框架材料作为非均相催化剂，可以在温和条件下实现烯烃的环氧化反应，催化剂循环使用15次活性仍然保持(Y.Qi,Y.Luan,J.Yu,X.Peng,G.Wang,Chem.Eur.J.2015,21,1589–1597)。Hosseini-Monfared等人则报道了利用手性酒石酸稳定的磁性纳米四氧化三铁在室温条件下催化烯烃的不对称环氧化反应合成手性环氧化合物，催化剂回收使用5次活性保持不变(L.Hadian-Dehkordi,H.Hosseini-Monfared,GreenChem.2016,18,497–507)。Pereira等人利用纳米四氧化三铁负载的锰卟啉配合物催化烯烃的环氧化反应(L.D.Dias,R.M.B.Carrilho,C.A.Henriques,M.J.F.Calvete,A.M.Masdeu-Bultj,C.Claver,L.M.Rossi,M.M.Pereira,ChemCatChem 2018,10,2792–2803)。The oxidants currently reported for the epoxidation of olefins include peroxyacids (AJJensen, K.Luthman, Tetrahedron Lett.1998, 39, 3213-3214), iodosobenzene (S.Mukerjee, A.Stassinopoulos, JPCaradonna, J.Am.Chem.Soc.1997,119,8097-8098; Y.Murakami, K.Konishi, J.Am.Chem.Soc.2007,129,14401-14407), hydrogen peroxide (BSLane, K.Burgess, Chem . Rev. 2003, 103, 2457-2473; O. Cussó, X. Ribas, J. Lloret-Fillol, M. Costas, Angew. Chem. Int. Ed. 2015, 54, 2729–2733; Y. Nakagawa, K . Kamata, M. Kotani, K. Yamaguchi, N. Mizuno, Angew. Chem. Int. Ed. 2005, 44, 5136–5141; N. Mizuno, S. Uchida, K. Kamata, R. Ishimoto, S. Nojima , K.Yonehara, Y.Sumida, Angew.Chem.Int.Ed.2010,49,9972–9976), tert-butyl hydroperoxide (D.Banerjee, RV Jagadeesh, K.Junge, M.-M.Pohl, J. Radnik, A. Brückner, M. Beller, Angew. Chem. Int. Ed. 2014, 53, 4359–4363; M. Shokouhimehr, Y. Piao, J. Kim, Y. Jang, T. Hyeon, Angew. Chem. Int. Ed. 2007, 46, 7039–7043) and oxygen (T. Mukaiyama, T. Yamada, Bull. Chem. Soc. Jpn. 1995, 68, 13-35). Oxygen as an oxidant has attracted more and more attention from chemists and industrialists due to its cheap, easy to handle and non-toxic properties. Over the past few decades, many transition metal catalysts including manganese (L.Hadian-Dehkordi, H.Hosseini-Monfared, P.Aleshkevych, Inorg.Chim.Acta 2017, 462, 142-151; S.Mohebbi, F. , J.Mol.Catal.A2006,256,265–268), cobalt (NVMaksimchuk, MS Melgunov, YA Chesalov, J.

AB

OAKholdeeva, J.Catal.2007,246,241–248), copper (Y.Qi, Y.Luan, J.Yu, X.Peng, G.Wang, Chem.Eur.J.2015,21,1589–1597; G .Yang,H.Du,J.Liu,Z.Zhou,X.Hu,Z.Zhang,Green Chem.,2017,19,675-681), palladium(X.He,L.Chen,X.Zhou,H. Ji, Catal.Commun.2016,83,78–81), ruthenium (P.Mekrattanachai,J.Liu,Z.Li,C.Cao,W.Song,Chem.Commun.2018,54,1433–1436), etc. have been reported for the oxygen epoxidation of alkenes. In order to facilitate the separation of catalysts and products and the recovery and reuse of catalysts, it is particularly important to develop efficient heterogeneous catalysts. For example, Wang et al. found that using copper metal-organic framework materials as heterogeneous catalysts can realize the epoxidation reaction of olefins under mild conditions, and the activity of the catalyst is still maintained after 15 cycles (Y. Qi, Y. Luan, J. Yu, X. Peng, G. Wang, Chem. Eur. J. 2015, 21, 1589–1597). Hosseini-Monfared et al. reported the use of chiral tartaric acid-stabilized magnetic nanometer ferric oxide to catalyze the asymmetric epoxidation reaction of olefins to synthesize chiral epoxy compounds at room temperature, and the activity of the catalyst remained unchanged after five times of recycling ( L. Hadian-Dehkordi, H. Hosseini-Monfared, Green Chem. 2016, 18, 497–507). Pereira et al. Catalyzed the epoxidation reaction of alkenes by manganese porphyrin complex supported by ferric ferric oxide nanometer (LDDias, RMBCarrilho, CA Henriques, MJFCalvete, AMMasdeu-Bultj, C.Claver, LM Rossi, MMPereira, ChemCatChem 2018, 10, 2792 –2803).

Although great progress has been made in the development of olefin epoxidation catalysts, many catalysts still have problems such as low catalytic activity, high price, difficult synthesis, and unfriendly environment. Therefore, it is still of great significance to develop inexpensive, readily available, environmentally friendly, recyclable, high-activity and high-selectivity catalyst systems.

Contents of the invention

In order to overcome the above-mentioned deficiencies in the prior art, the object of the present invention is to provide a method for synthesizing epoxy compounds by catalyzing epoxidation of olefins with nano-alumina.

The invention provides a method for synthesizing epoxy compounds by catalyzing olefin epoxidation with nano-alumina. In the method, olefin is used as raw material, and the epoxy compound is obtained by epoxidation in the next step under the conditions of nano-alumina as a catalyst, aliphatic aldehyde as a reducing agent and oxygen as an oxidizing agent.

The object of the present invention is achieved at least by one of the following technical solutions.

In the method provided by the invention, solvent, olefin, nano-alumina and aliphatic aldehyde are added into a reactor to obtain a mixed solution, in which olefin is used as a raw material, nano-alumina is used as a catalyst, and aliphatic aldehyde is used as a reducing agent, and the reaction vessel is evacuated Afterwards, oxygen is introduced, heated and stirred for reaction, and a reaction solution is obtained after the reaction is completed, and the reaction solution is separated and purified to obtain the epoxy compound.

A kind of method that utilizes nano-alumina to catalyze epoxidation of olefin to synthesize epoxy compound provided by the present invention, its chemical reaction equation is:

为1-苯基-1-环己烯、1-辛烯、正葵烯、四环十二碳烯、环十二烯、苯乙烯、顺-1-苯基丙烯、反-1-苯基丙烯、1-烯丙基-2-甲苯、4-苯基-1-丁烯、3-溴苯乙烯、3-氯苯乙烯、4-溴苯乙烯、4-氯苯乙烯、反-1,2-二苯乙烯、1-乙酰基-1-环己烯、反-4-苯基-3-丁烯-2-酮、苯乙酸烯丙酯、反-查耳酮、2-苯亚甲基环己酮、反-3-己烯酸乙酯、肉桂酸甲酯、肉桂酸肉桂酯、乙酸肉桂酯、丙酸肉桂酯、丁酸肉桂酯、异丁酸肉桂酯、1,4-环氧-1,4-二氢萘中的一种；In the formula,

1-phenyl-1-cyclohexene, 1-octene, n-decene, tetracyclododecene, cyclododecene, styrene, cis-1-phenylpropene, trans-1-phenyl Propylene, 1-allyl-2-toluene, 4-phenyl-1-butene, 3-bromostyrene, 3-chlorostyrene, 4-bromostyrene, 4-chlorostyrene, trans-1, 2-Stilbene, 1-acetyl-1-cyclohexene, trans-4-phenyl-3-buten-2-one, allyl phenylacetate, trans-chalcone, 2-benzylidene Cyclohexanone, ethyl trans-3-hexenoate, methyl cinnamate, cinnamyl cinnamate, cinnamyl acetate, cinnamyl propionate, cinnamyl butyrate, cinnamyl isobutyrate, 1,4-cyclo One of oxy-1,4-dihydronaphthalene;

为1-苯基-7-氧杂-双环[4.1.0]庚烷、1,2-环氧辛烷、1,2-环氧葵烷、2R,2aR,3S,6R,6aS,7S)-十氢-2:,7:3,6-二甲桥八氢萘,四环[2,3-b]环氧乙烯、1,3-氧杂双环[10.1.0]十三烷、苯基环氧乙烷、顺-2-甲基-3-苯基环氧乙烷、反-2-甲基-3-苯基环氧乙烷、2-甲基-1,2-环氧苯丙烷、1,2-环氧-4-苯基-丁烷、3-溴苯基环氧乙烷、3-氯苯基环氧乙烷、4-溴苯基环氧乙烷、4-氯苯基环氧乙烷、反-1,2-二苯基环氧乙烷、1-(7-氧杂双环[4.1.0]庚-1-基)乙酮、1-(3-苯基环氧乙烷基)-乙酮、苯乙酸(环氧乙烷基甲基)酯、(3-苯基环氧乙烷基)苯基甲酮、2-苯基-1-氧杂螺[2.5]辛烷-4-酮、2-(3-乙基环氧乙烷基)乙酸乙酯、2-苯基环氧乙烷-1-羧酸甲酯、乙酸(3-苯基环氧乙烷基甲基)酯、丙酸(3-苯基环氧乙烷基甲基)酯、丁酸(3-苯基环氧乙烷基甲基)酯、异丁酸(3-苯基环氧乙烷基甲基)酯、肉桂酸(3-苯基环氧乙烷基甲基)酯、1a,2,7,7a-四氢-2,7-环氧萘并[2,3-b]环氧乙烷中的一种。In the formula,

1-phenyl-7-oxa-bicyclo[4.1.0]heptane, 1,2-epoxyoctane, 1,2-epoxydecane, 2R, 2aR, 3S, 6R, 6aS, 7S) -Decahydro-2:,7:3,6-Dimethyloctahydronaphthalene, tetracyclo[2,3-b]oxirane, 1,3-oxabicyclo[10.1.0]tridecane, benzene oxirane, cis-2-methyl-3-phenyloxirane, trans-2-methyl-3-phenyloxirane, 2-methyl-1,2-epoxybenzene Propane, 1,2-epoxy-4-phenyl-butane, 3-bromophenyloxirane, 3-chlorophenyloxirane, 4-bromophenyloxirane, 4-chloro Phenyloxirane, trans-1,2-diphenyloxirane, 1-(7-oxabicyclo[4.1.0]hept-1-yl)ethanone, 1-(3-phenyl Oxiranyl)-ethanone, (oxiranylmethyl) phenylacetate, (3-phenyloxiranyl) phenyl ketone, 2-phenyl-1-oxaspiro[ 2.5] Octane-4-one, 2-(3-ethyloxiranyl) ethyl acetate, 2-phenyloxirane-1-carboxylate methyl ester, acetic acid (3-phenylepoxy Ethyl Methyl) Ester, (3-Phenyl Oxiranyl Methyl) Propionate, (3-Phenyl Oxiranyl Methyl) Butyrate, (3-Phenyl Isobutyrate Oxiranylmethyl) ester, (3-phenyloxiranylmethyl) cinnamate, 1a,2,7,7a-tetrahydro-2,7-epoxynaphtho[2,3 -b] one of ethylene oxide.

A kind of method that utilizes nano-alumina to catalyze epoxidation of olefin to synthesize epoxy compound provided by the invention comprises the following steps:

(1) Add organic solvent, olefin, nano-alumina and aliphatic aldehyde into the reaction vessel, mix uniformly to obtain a mixed solution, vacuumize the reaction vessel and feed oxygen into it, heat to carry out stirring reaction, and cool to room temperature to obtain a reaction solution;

(2) Separating and purifying the reaction solution in step (1) to obtain the epoxy compound.

Further, the organic solvent in step (1) is one of acetonitrile and ethyl acetate.

Further, the alkene described in step (1) is 1-phenyl-1-cyclohexene, 1-octene, n-decene, tetracyclododecene, cyclododecene, styrene, cis-1 -Phenylpropene, trans-1-phenylpropene, 1-allyl-2-toluene, 4-phenyl-1-butene, 3-bromostyrene, 3-chlorostyrene, 4-bromostyrene , 4-chlorostyrene, trans-1,2-stilbene, 1-acetyl-1-cyclohexene, trans-4-phenyl-3-buten-2-one, allyl phenylacetate, trans-chalcone, 2-benzylidene cyclohexanone, trans-3-hexenoic acid ethyl ester, methyl cinnamate, cinnamyl cinnamate, cinnamyl acetate, cinnamyl propionate, cinnamyl butyrate, Cinnamyl isobutyrate, 1,4-epoxy-1,4-dihydronaphthalene.

Further, the particle size of the nano-alumina in step (1) is 20-100 nanometers; the molar ratio of the nano-alumina to olefin is (0.05-0.15):1.

Further, the fatty aldehyde described in step (1) is butyraldehyde, isobutyraldehyde, isovaleraldehyde, valeraldehyde, nonanal, 3,5,5-trimethylhexanal, cyclohexanal, benzaldehyde or 3 - methylbenzaldehyde; the molar ratio of the fatty aldehyde to the olefin is (2-3):1.

Further, the molar volume ratio of the olefin to the organic solvent in step (1) is 0.1-0.5 mmol/mL.

Further, after the oxygen is introduced in step (1), the gas pressure in the reaction vessel is 1-2 atmospheres.

Further, the heating temperature in step (1) is 50-60° C., the stirring rate of the stirring reaction is 400-800 rpm, and the stirring reaction time is 12-36 hours.

Further, the separation and purification described in step (2) includes:

The reaction solution described in step (1) is filtered and concentrated under reduced pressure to obtain a crude product, and then purified by column chromatography to obtain an epoxy compound; the eluent of the column chromatography is a mixed solvent of petroleum ether and ethyl acetate, The volume ratio of petroleum ether and ethyl acetate is (10-50):1.

Compared with the prior art, the present invention has the following advantages and beneficial effects:

The present invention provides a method for synthesizing epoxy compounds by catalyzing olefin epoxidation with nano-alumina, which is different from the traditional epoxy compound synthesis method, and has the advantages of cheap and easy-to-obtain catalysts, mild reaction conditions, and applicability to substrates Wide, safe and simple to operate, has potential industrial application prospects.

Description of drawings

Fig. 1 and Fig. 2 are respectively the hydrogen spectrogram and the carbon spectrogram of embodiment 1～12 obtained target product;

Fig. 3 and Fig. 4 are respectively the hydrogen spectrogram and the carbon spectrogram of the target product obtained in embodiment 13;

Fig. 5 and Fig. 6 are respectively the hydrogen spectrogram and the carbon spectrogram of the obtained target product of embodiment 14;

Fig. 7 and Fig. 8 are respectively the hydrogen spectrogram and the carbon spectrogram of the target product obtained in embodiment 15;

Fig. 9 and Fig. 10 are respectively the hydrogen spectrogram and the carbon spectrogram of the target product obtained in embodiment 16;

Fig. 11 and Fig. 12 are respectively the hydrogen spectrogram and the carbon spectrogram of the target product obtained in embodiment 17;

Fig. 13 and Fig. 14 are respectively the hydrogen spectrogram and the carbon spectrogram of the target product obtained in embodiment 18;

Fig. 15 and Fig. 16 are respectively the hydrogen spectrogram and the carbon spectrogram of the target product obtained in embodiment 19;

Fig. 17 and Fig. 18 are respectively the hydrogen spectrogram and the carbon spectrogram of the target product obtained in embodiment 20;

Fig. 19 and Fig. 20 are respectively the hydrogen spectrogram and the carbon spectrogram of the target product obtained in Example 21.

Detailed ways

The specific implementation of the present invention will be further described below in conjunction with the accompanying drawings and examples, but the implementation and protection of the present invention are not limited thereto. It should be pointed out that, if there are any processes in the following that are not specifically described in detail, those skilled in the art can realize or understand with reference to the prior art. The reagents or instruments used were not indicated by the manufacturer, and they were regarded as conventional products that can be purchased from the market.

Example 1

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 ml of acetonitrile, 1 mmol of 1-phenyl-1-cyclohexene, 3 mmol of 3,5,5-trimethylhexanal, 0.1 mmol of nano-alumina (particle size 20nm) into the reaction tube, After vacuumizing the reaction tube, fill it with oxygen, the gas pressure of the reaction tube after filling the oxygen is 1 atmosphere, stir and react at 60°C for 24 hours, the stirring rate is 700rpm, stop heating and stirring, cool to room temperature, The reaction solution was filtered, concentrated under reduced pressure, and separated and purified by column chromatography. The developer used in column chromatography was a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 50:1 to obtain the target product with a yield of 75%.

Example 2

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 ml of acetonitrile, 1 mmol of 1-phenyl-1-cyclohexene, 3 mmol of 3,5,5-trimethylhexanal, 0.1 mmol of nano-alumina (particle size 50nm) into the reaction tube, After vacuumizing the reaction tube, fill it with oxygen, the gas pressure of the reaction tube after filling the oxygen is 1 atmosphere, stir and react at 60°C for 24 hours, the stirring rate is 700rpm, stop heating and stirring, cool to room temperature, The reaction solution was filtered, concentrated under reduced pressure, and separated and purified by column chromatography. The developer used in column chromatography was a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 50:1 to obtain the target product with a yield of 88%.

Example 3

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 ml of acetonitrile, 1 mmol of 1-phenyl-1-cyclohexene, 3 mmol of 3,5,5-trimethylhexanal, 0.1 mmol of nano-alumina (particle size 100nm) into the reaction tube, After vacuumizing the reaction tube, fill it with oxygen, the gas pressure of the reaction tube after filling the oxygen is 1 atmosphere, stir and react at 60°C for 24 hours, the stirring rate is 700rpm, stop heating and stirring, cool to room temperature, The reaction solution was filtered, concentrated under reduced pressure, and separated and purified by column chromatography. The developer used in column chromatography was a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 50:1 to obtain the target product with a yield of 72%.

Example 4

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 ml of acetonitrile, 1 mmol of 1-phenyl-1-cyclohexene, 3 mmol of 3,5,5-trimethylhexanal, 0.05 mmol of nano-alumina (particle size 50nm) into the reaction tube, After vacuumizing the reaction tube, fill it with oxygen, the gas pressure of the reaction tube after filling the oxygen is 1 atmosphere, stir and react at 60°C for 24 hours, the stirring rate is 700rpm, stop heating and stirring, cool to room temperature, The reaction solution was filtered, concentrated under reduced pressure, and separated and purified by column chromatography. The developer used in column chromatography was a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 50:1 to obtain the target product with a yield of 57%.

Example 5

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 milliliters of acetonitrile, 1 mmol 1-phenyl-1-cyclohexene, 3 mmol 3,5,5-trimethylhexanal, 0.15 mmol nano-alumina (particle size 50nm) into the reaction tube, After vacuumizing the reaction tube, fill it with oxygen, the gas pressure of the reaction tube after filling the oxygen is 1 atmosphere, stir and react at 60°C for 24 hours, the stirring rate is 700rpm, stop heating and stirring, cool to room temperature, The reaction solution was filtered, concentrated under reduced pressure, and separated and purified by column chromatography. The developer used in column chromatography was a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 50:1 to obtain the target product with a yield of 70%.

Example 6

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 ml of acetonitrile, 1 mmol of 1-phenyl-1-cyclohexene, 3 mmol of 3,5,5-trimethylhexanal, 0.1 mmol of nano-alumina (particle size 50nm) into the reaction tube, After vacuumizing the reaction tube, fill it with oxygen, the gas pressure of the reaction tube after filling the oxygen is 1 atmosphere, stir and react at 50°C for 24 hours, the stirring rate is 700rpm, stop heating and stirring, cool to room temperature, The reaction solution was filtered, concentrated under reduced pressure, and separated and purified by column chromatography. The developer used in column chromatography was a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 50:1 to obtain the target product with a yield of 20%.

Example 7

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 milliliters of acetonitrile, 1 mmol of 1-phenyl-1-cyclohexene, 3 mmol of isobutyraldehyde, 0.1 mmol of nano-alumina (50 nm in particle size) in the reaction tube, vacuumize the reaction tube, and fill Oxygen is charged, the gas pressure of the reaction tube is 1 atmosphere after the oxygen is charged, the reaction is stirred at 60°C for 24 hours, the stirring rate is 700rpm, the heating and stirring are stopped, cooled to room temperature, the reaction solution is filtered, concentrated under reduced pressure, Separation and purification by column chromatography, the developer used in column chromatography is a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 50:1, to obtain the target product with a yield of 54%.

Example 8

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 2 ml of acetonitrile, 1 mmol of 1-phenyl-1-cyclohexene, 3 mmol of butyraldehyde, 0.1 mmol of nano-alumina (particle size 50nm) into the reaction tube, vacuumize the reaction tube, and fill it with Oxygen, after filling the oxygen, the gas pressure of the reaction tube is 1 atmosphere, stir and react at 60°C for 24 hours, the stirring rate is 700rpm, stop heating and stirring, cool to room temperature, filter the reaction solution, concentrate under reduced pressure, and then Separation and purification by column chromatography, the used column chromatography developer is a mixed solvent of petroleum ether: ethyl acetate with a volume ratio of 50:1, to obtain the target product with a yield of 24%.

Example 9

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 10 ml of acetonitrile, 1 mmol of 1-phenyl-1-cyclohexene, 3 mmol of 3,5,5-trimethylhexanal, 0.1 mmol of nano-alumina (particle size 50nm) into the reaction tube, After vacuumizing the reaction tube, fill it with oxygen, the gas pressure of the reaction tube after filling the oxygen is 1 atmosphere, stir and react at 60°C for 24 hours, the stirring rate is 700rpm, stop heating and stirring, cool to room temperature, The reaction solution was filtered, concentrated under reduced pressure, and separated and purified by column chromatography. The developer used in column chromatography was a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 50:1 to obtain the target product with a yield of 83%.

Example 10

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 ml of ethyl acetate, 1 mmol of 1-phenyl-1-cyclohexene, 3 mmol of 3,5,5-trimethylhexanal, 0.1 mmol of nano-alumina (particle size 50nm) into the reaction tube ), after the reaction tube was evacuated, filled with oxygen, the gas pressure of the reaction tube after filling the oxygen was 1 atmosphere, stirred and reacted at 60°C for 24 hours, the stirring rate was 700rpm, stopped heating and stirring, and cooled to At room temperature, the reaction solution was filtered, concentrated under reduced pressure, and then separated and purified by column chromatography. The column chromatography developer used was a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 50:1 to obtain the target product with a yield of 56%.

Example 11

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 ml of acetonitrile, 1 mmol of 1-phenyl-1-cyclohexene, 2 mmol of 3,5,5-trimethylhexanal, 0.1 mmol of nano-alumina (particle size 50nm) into the reaction tube, After vacuumizing the reaction tube, fill it with oxygen, the gas pressure of the reaction tube after filling the oxygen is 1 atmosphere, stir and react at 60°C for 24 hours, the stirring rate is 700rpm, stop heating and stirring, cool to room temperature, The reaction solution was filtered, concentrated under reduced pressure, and separated and purified by column chromatography. The developer used in column chromatography was a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 50:1 to obtain the target product with a yield of 65%.

Example 12

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 ml of acetonitrile, 1 mmol of 1-phenyl-1-cyclohexene, 3 mmol of 3,5,5-trimethylhexanal, 0.1 mmol of nano-alumina (particle size 50nm) into the reaction tube, After vacuumizing the reaction tube, fill it with oxygen, the gas pressure of the reaction tube after filling the oxygen is 2 atmospheres, stir and react at 60°C for 12 hours, the stirring rate is 400rpm, stop heating and stirring, cool to room temperature, The reaction solution was filtered, concentrated under reduced pressure, and then separated and purified by column chromatography. The developer used in column chromatography was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 50:1 to obtain the target product with a yield of 37%.

The hydrogen spectrum and carbon spectrum of the products obtained in Examples 1 to 12 are shown in Figure 1 and Figure 2 respectively, and the structural characterization data are as follows:

¹ H NMR (500MHz, CDCl ₃ ): δ=7.27–7.11(m,5H), 2.95(d, J=3.5Hz, 1H), 2.19–2.13(m,1H), 2.02-1.97(m,1H) ,1.92–1.81(m,2H),1.53–1.47(m,2H),1.38-1.31(m,1H),1.24-1.15(m,1H);

¹³ C NMR (126MHz, CDCl ₃ ): δ=142.6, 128.3, 127.2, 125.3, 77.4, 77.1, 76.9, 61.9, 60.2, 28.9, 24.8, 20.2, 19.8;

IR (KBr): 3060, 2933, 1450, 966, 859, 749, ^{543 cm -1} .

According to the above data, the structure of the target product is deduced as follows:

Example 13

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 milliliters of acetonitrile, 1 mmol of 1-octene, 3 mmol of 3,5,5-trimethylhexanal, 0.1 mmol of nano-alumina (particle size 50nm) into the reaction tube, and vacuumize the reaction tube , filled with oxygen, the gas pressure of the reaction tube after filling the oxygen was 1 atmosphere, stirred and reacted at 60°C for 12 hours, the stirring rate was 800rpm, stopped heating and stirring, cooled to room temperature, filtered the reaction solution, and decompressed Concentrate, then separate and purify by column chromatography, the developer used in column chromatography is a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 50:1, to obtain the target product with a yield of 63%.

The hydrogen spectrum and carbon spectrum of the obtained target product are shown in Figure 3 and Figure 4 respectively, and the structural characterization data are as follows:

¹ H NMR (400MHz, CDCl ₃ ): δ=2.82–2.77(m,1H), 2.64–2.62(m,1H), 2.36–2.34(m,1H), 1.46–1.21(m,10H), 0.80( t,J=6.8Hz,3H);

¹³ C NMR (100MHz, CDCl ₃ ): δ=77.4, 77.1, 76.8, 52.2, 46.8, 32.4, 31.7, 29.0, 25.9, 22.5, 13.9;

IR (KBr): 2934, 1462, 836 cm ^-1 .

The structure of the target product is deduced from the above data as follows:

Example 14

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 milliliters of acetonitrile, 1 mmol of n-decene, 3 mmol of 3,5,5-trimethylhexanal, 0.1 mmol of nano-alumina (particle size 50nm) in the reaction tube, and vacuumize the reaction tube, Fill with oxygen, the gas pressure of the reaction tube after filling the oxygen is 1 atmosphere, stir and react at 60°C for 24 hours, the stirring rate is 700rpm, stop heating and stirring, cool to room temperature, filter the reaction solution, concentrate under reduced pressure , and then separated and purified by column chromatography, the column chromatography developer used was petroleum ether: ethyl acetate mixed solvent with a volume ratio of 50:1, to obtain the target product with a yield of 75%.

The hydrogen spectrum and carbon spectrum of the obtained target product are shown in Figure 5 and Figure 6 respectively, and the structural characterization data are as follows:

¹ H NMR (500MHz, CDCl ₃ ): δ=2.88(s,1H),2.73-2.71(m,1H),2.44–2.43(m,1H),1.53–1.26(m,14H),0.86(t, J = 6.5Hz, 3H);

¹³ C NMR (126MHz, CDCl ₃ ): δ=77.3, 77.0, 76.8, 52.4, 47.1, 32.5, 31.8, 29.5, 29.4, 29.2, 26.0, 22.6, 14.0;

IR (KBr): 2932, 1461, 836 cm ^-1 .

The structure of the target product is deduced from the above data as follows:

Example 15

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 milliliters of acetonitrile, 1 mmol of tetracyclododecene, 3 mmol of 3,5,5-trimethylhexanal, and 0.1 mmol of nano-alumina (particle size 50 nm) into the reaction tube, and pump the reaction tube After vacuuming, fill with oxygen, the gas pressure of the reaction tube after filling the oxygen is 1 atmosphere, stir and react at 60°C for 24 hours, the stirring rate is 700rpm, stop heating and stirring, cool to room temperature, filter the reaction solution, Concentrate under reduced pressure, and then separate and purify by column chromatography. The developer used in column chromatography is petroleum ether: ethyl acetate mixed solvent with a volume ratio of 50:1 to obtain the target product with a yield of 90%.

The hydrogen spectrum and carbon spectrum of the obtained target product are shown in Figure 7 and Figure 8 respectively, and the structural characterization data are as follows:

¹ H NMR (500MHz, CDCl ₃ ): δ=3.07(s,2H),2.53(s,2H),2.21(s,2H),1.80(d,J=11.0Hz,1H),1.75(t,J =9.5Hz,2H),1.42(d,J=7.5Hz,2H),1.32(d,J=9.5Hz,1H),0.97–0.93(m,2H),0.89(d,J=11.0Hz,1H ),0.55(d,J=9.5Hz,1H);

¹³ C NMR (126MHz, CDCl ₃ ): δ=77.4, 77.1, 76.9, 51.4, 50.0, 41.5, 36.9, 36.6, 31.1, 28.2;

IR(KBr):2908,1469,851cm ^-1 ;

HRMS (ESI) Calcd for C ₁₂ H ₁₆ O [M+H] ⁺ : 199.1093, Found 199.1089.

The structure of the target product is deduced from the above data as follows:

Example 16

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 ml of acetonitrile, 1 mmol of styrene, 3 mmol of 3,5,5-trimethylhexanal, and 0.1 mmol of nano-alumina (particle size 50 nm) into the reaction tube, vacuumize the reaction tube, and fill Oxygen is charged, the gas pressure of the reaction tube is 1 atmosphere after the oxygen is filled, the reaction is stirred and reacted at 60°C for 36 hours, the stirring rate is 700rpm, the heating and stirring are stopped, cooled to room temperature, the reaction solution is filtered, concentrated under reduced pressure, Separation and purification by column chromatography, the developer used in column chromatography is a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 50:1, to obtain the target product with a yield of 69%.

The hydrogen spectrum and carbon spectrum of the obtained target product are shown in Figure 9 and Figure 10 respectively, and the structural characterization data are as follows:

¹ H NMR (500MHz, CDCl ₃ ): δ=7.31–7.22(m, 5H), 3.78(t, J=3.0Hz, 1H), 3.05(t, J=5.0Hz, 1H), 2.72(dd, J =5.5Hz,2.5Hz,1H);

¹³ C NMR (126MHz, CDCl ₃ ): δ＝137.8, 128.6, 128.2, 125.6, 77.5, 77.3, 77.0, 52.4, 51.2;

IR (KBr): 3676, 3042, 1708, 1582, 1480, 1385, 984, 877, 757, 692, 540 cm ^-1 .

The structure of the target product is deduced from the above data as follows:

Example 17

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 milliliters of acetonitrile, 1 mmol of trans-1,2-stilbene, 3 mmol of 3,5,5-trimethylhexanal, and 0.1 mmol of nano-alumina (particle size 50nm) into the reaction tube. After the reaction tube is evacuated, it is filled with oxygen, and the gas pressure of the reaction tube after filling the oxygen is 1 atmosphere. Stir and react at 60°C for 24 hours at a stirring rate of 700rpm. Stop heating and stirring, cool to room temperature, and react Liquid was filtered, concentrated under reduced pressure, and then separated and purified by column chromatography. The developing solvent used in column chromatography was petroleum ether: ethyl acetate mixed solvent with a volume ratio of 50:1 to obtain the target product with a yield of 95%.

The hydrogen spectrum and carbon spectrum of the obtained target product are shown in Figure 11 and Figure 12 respectively, and the structural characterization data are as follows:

¹ H NMR (400MHz, CDCl ₃ ): δ=7.51–7.42 (m, 10H), 3.98 (s, 2H);

¹³ C NMR (100MHz, CDCl ₃ ): δ＝137.3, 128.7, 128.5, 125.7, 77.6, 77.3, 76.9, 63.0;

IR (KBr): 3692, 3029, 1724, 1578, 1485, 1289, 1004, 863, 704 ^{cm -1} .

The structure of the target product is deduced from the above data as follows:

Example 18

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 milliliters of acetonitrile, 1 mmol of cinnamyl acetate, 3 mmol of 3,5,5-trimethylhexanal, and 0.1 mmol of nano-alumina (particle size 50nm) into the reaction tube, and vacuumize the reaction tube. Fill with oxygen, the gas pressure of the reaction tube after filling the oxygen is 1 atmosphere, stir and react at 60°C for 24 hours, the stirring rate is 700rpm, stop heating and stirring, cool to room temperature, filter the reaction solution, concentrate under reduced pressure , and then separated and purified by column chromatography, the column chromatography developer used was petroleum ether: ethyl acetate mixed solvent with a volume ratio of 20:1, to obtain the target product with a yield of 76%.

The hydrogen spectrum and carbon spectrum of the obtained target product are shown in Figure 13 and Figure 14 respectively, and the structural characterization data are as follows:

¹ H NMR (500MHz, CDCl ₃ ): δ=7.34–7.21(m,5H), 4.42(dd,J=12.5Hz,3.0Hz,1H), 4.05–4.01(m,1H), 3.75(s,1H ),3.21–3.20(m,1H),2.06–2.05(m,3H);

¹³ C NMR (126MHz, CDCl ₃ ): δ=170.7, 136.3, 128.6, 128.5, 125.7, 77.5, 77.3, 77.0, 64.2, 59.3, 56.4, 20.7;

IR (KBr): 3694, 3483, 3144, 1729, 1572, 987 ^{cm -1} .

The structure of the target product is deduced from the above data as follows:

Example 19

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 milliliters of acetonitrile, 1 mmol of cinnamyl propionate, 3 mmol of 3,5,5-trimethylhexanal, 0.1 mmol of nano-alumina (particle size 50nm) into the reaction tube, and vacuumize the reaction tube , filled with oxygen, the gas pressure of the reaction tube after filling the oxygen was 1 atmosphere, stirred and reacted at 60°C for 24 hours, the stirring rate was 700rpm, stopped heating and stirring, cooled to room temperature, filtered the reaction solution, and decompressed Concentrate, then separate and purify by column chromatography, the column chromatography developer used is petroleum ether: ethyl acetate mixed solvent with a volume ratio of 20:1, to obtain the target product with a yield of 86%.

The hydrogen spectrum and carbon spectrum of the obtained target product are shown in Figure 15 and Figure 16 respectively, and the structural characterization data are as follows:

¹ H NMR (500MHz, CDCl ₃ ): δ=7.28–7.18(m, 5H), 4.40(dd, J=12.5Hz, 3.5Hz, 1H), 4.01(dd, J=12.5Hz, 6.0Hz, 1H) ,3.72(d,J=2.0Hz,1H),3.19-3.16(m,1H),2.31(q,J=7.5Hz,2H),1.08(t,J=7.5Hz,3H);

¹³ C NMR (126MHz, CDCl ₃ ): δ=174.1, 136.3, 128.6, 128.5, 125.7, 77.5, 77.2, 77.0, 64.1, 59.3, 56.4, 27.3, 9.0;

IR(KBr):3665,3495,3282,3130,2975,1722,1583cm ^-1 ;

HRMS (ESI) Calcd for C ₁₂ H ₁₄ O ₃ [M+H] ⁺ : 229.0835, Found 229.0840.

The structure of the target product is deduced from the above data as follows:

Example 20

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 milliliters of acetonitrile, 1 mmol of cinnamyl butyrate, 3 mmol of 3,5,5-trimethylhexanal, 0.1 mmol of nano-alumina (particle size 50nm) into the reaction tube, and vacuumize the reaction tube , filled with oxygen, the gas pressure of the reaction tube after filling the oxygen was 1 atmosphere, stirred and reacted at 60°C for 24 hours, the stirring rate was 700rpm, stopped heating and stirring, cooled to room temperature, filtered the reaction solution, and decompressed Concentrate, then separate and purify by column chromatography, the column chromatography developer used is petroleum ether:ethyl acetate mixed solvent with a volume ratio of 20:1, to obtain the target product with a yield of 82%.

The hydrogen spectrum and carbon spectrum of the obtained target product are shown in Figure 17 and Figure 18 respectively, and the structural characterization data are as follows:

¹ H NMR (500MHz, CDCl ₃ ): δ=7.28–7.18 (m, 5H), 4.40 (dd, J=12.5, 3.5, 1H), 4.02 (dd, J=12.5Hz, 6.0Hz, 1H), 3.71 (d, J=2.0Hz, 1H), 3.18–3.16(m, 1H), 2.27(t, J=7.5Hz, 2H), 1.64-1.56(m, 2H), 0.88(t, J=7.5Hz, 3H);

¹³ C NMR (126MHz, CDCl ₃ ): δ=173.3, 136.3, 128.6, 128.5, 125.7, 77.4, 77.1, 76.8, 63.9, 59.4, 56.4, 35.9, 18.4, 13.7;

IR(KBr):3680,3477,2959,1735,1583,1460,1175,993,880,690cm ^-1 ;

HRMS (ESI) Calcd for C ₁₃ H ₁₆ O ₃ [M+H] ⁺ : 243.0992, Found 243.0996.

The structure of the target product is deduced from the above data as follows:

Example 21

A method utilizing nano-alumina to catalyze epoxidation of olefins to synthesize epoxy compounds, comprising the steps of:

Add 5 ml of acetonitrile, 1 mmol of cinnamyl isobutyrate, 3 mmol of 3,5,5-trimethylhexanal, 0.1 mmol of nano-alumina (particle size 50 nm) into the reaction tube, and vacuumize the reaction tube Then, fill with oxygen, the gas pressure of the reaction tube after filling the oxygen is 1 atmosphere, stir and react at 60°C for 24 hours, the stirring rate is 700rpm, stop heating and stirring, cool to room temperature, filter the reaction solution, reduce Concentrate under reduced pressure, and then separate and purify by column chromatography, the column chromatography developer used is petroleum ether:ethyl acetate mixed solvent with a volume ratio of 20:1, to obtain the target product with a yield of 88%.

The hydrogen spectrum and carbon spectrum of the obtained target product are shown in Figure 19 and Figure 20 respectively, and the structural characterization data are as follows:

¹ H NMR (500MHz, CDCl ₃ ): δ=7.32–7.21 (m, 5H), 4.44 (dd, J=12.0Hz, 3.0Hz, 1H), 4.05 (dd, J=12.5Hz, 6.0Hz, 1H) ,3.75(d,J=2.0Hz,1H),3.22-3.20(m,1H),2.62-2.53(m,1H),1.16(d,J=7.5Hz,6H);

¹³ C NMR (126MHz, CDCl ₃ ): δ=176.8, 136.3, 128.6, 128.5, 125.7, 77.4, 77.1, 76.9, 64.0, 59.4, 56.3, 33.9, 19.0;

IR(KBr):3680,2961,1737,1589,1463,1373,1163,990,881,758,695cm ^-1 ;

HRMS (ESI) Calcd for C ₁₃ H ₁₆ O ₃ [M+H] ⁺ : 243.0992, Found 243.0996.

The structure of the target product is deduced from the above data as follows:

The above examples are only preferred implementations of the present invention, and are only used to explain the present invention, rather than limit the present invention. Changes, replacements, modifications, etc. made by those skilled in the art without departing from the spirit of the present invention shall belong to the present invention. protection scope of the invention.

Claims (5)

1. A method for synthesizing an epoxy compound by catalyzing olefin epoxy by using nano alumina is characterized in that a chemical reaction equation is that

In the method, in the process of the invention,

is one of 1-phenyl-1-cyclohexene, 1-octene, n-decene, tetracyclododecene, cyclododecene, styrene, cis-1-phenylpropene, trans-1-phenylpropene, 1-allyl-2-toluene, 4-phenyl-1-butene, 3-bromostyrene, 3-chlorostyrene, 4-bromostyrene, 4-chlorostyrene, trans-1, 2-stilbene, 1-acetyl-1-cyclohexene, trans-4-phenyl-3-buten-2-one, allyl phenylacetate, trans-chalcone, 2-benzylidene cyclohexanone, trans-3-hexenoate ethyl ester, methyl cinnamate, cinnamyl acetate, cinnamyl propionate, cinnamyl butyrate, cinnamyl isobutyrate, 1, 4-epoxy-1, 4-dihydronaphthalene;

in the middle of，

1-phenyl-7-oxa-bicyclo [4.1.0]Heptane, 1, 2-epoxyoctane, 1, 2-epoxysunflower-alkylene, tetracyclo [6.2.1.1 ] ^3,6 .0 ^2,7 ]Twelve-4, 5-epoxy alkane, 1, 3-oxabicyclo [10.1.0 ]]Tridecane, phenyloxirane, cis-2-methyl-3-phenyloxirane, trans-2-methyl-3-phenyloxirane, 2-methyl-1, 2-phenylpropanolene, 1, 2-epoxy-4-phenyl-butane, 3-bromophenyloxirane, 3-chlorophenyl oxirane, 4-bromophenyloxirane, 4-chlorophenyl oxirane, trans-1, 2-diphenyloxirane, 1- (7-oxabicyclo [4.1.0 ]]Hept-1-yl) ethanone, 1- (3-phenyloxiranyl) -ethanone, (oxiranylmethyl) phenylacetate, (3-phenyloxiranyl) phenylmethanone, 2-phenyl-1-oxaspiro [2.5 ]]Octane-4-one, ethyl 2- (3-ethyloxiranyl) acetate, methyl 2-phenyloxirane-1-carboxylate, 3-phenyloxiranylmethyl acetate, 3-phenyloxiranylmethyl propionate, 3-phenyloxiranylmethyl butyrate, 3-phenyloxiranylmethyl isobutyrate, 3-phenyloxiranylmethyl cinnamate, 1a,2,7 a-tetrahydro-2, 7-epoxynaphtho [2,3-b ]]One of ethylene oxide;

the method for synthesizing the epoxy compound by catalyzing olefin epoxy by using nano alumina comprises the following steps:

(1) Adding an organic solvent, olefin, nano aluminum oxide and fatty aldehyde into a reaction vessel, uniformly mixing to obtain a mixed solution, vacuumizing the reaction vessel, introducing oxygen, heating, stirring for reaction, and cooling to obtain a reaction solution, wherein the particle size of the nano aluminum oxide is 20-100 nanometers, and the molar ratio of the nano aluminum oxide to the olefin is (0.05-0.15): 1, the organic solvent is one of acetonitrile and ethyl acetate, the fatty aldehyde is 3, 5-trimethyl hexanal, the gas pressure of the reaction vessel after oxygen is introduced is 1-2 atmospheres, and the heating temperature is 50-60 ℃;

(2) And (3) separating and purifying the reaction liquid in the step (1) to obtain the epoxy compound.

2. The method for synthesizing an epoxy compound by catalyzing olefin epoxidation with nano alumina according to claim 1, wherein the molar volume ratio of the olefin to the organic solvent in the step (1) is 0.1-0.5:1mmol/mL.

3. The method for synthesizing an epoxy compound by catalyzing the epoxidation of an olefin with nano alumina according to claim 1, wherein the molar ratio of the fatty aldehyde to the olefin in the step (1) is (2-3): 1.

4. the method for synthesizing an epoxy compound by catalyzing an olefin epoxidation with nano alumina according to claim 1, wherein in the step (1), the stirring rate of the stirring reaction is 400 to 800rpm; the stirring reaction time is 12-36h.

5. The method for synthesizing an epoxy compound by catalyzing an olefin epoxidation with nano alumina according to claim 1, wherein said separating and purifying in the step (2) comprises:

filtering and concentrating the reaction liquid obtained in the step (1) under reduced pressure to obtain a crude product, and purifying the crude product by column chromatography to obtain an epoxy compound; the eluent of the column chromatography is a mixed solvent of petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is (10-50): 1.

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