Ether ester compound as well as preparation method and application thereof in olefin polymerization

Abstract

The invention relates to an ether ester compound, and particularly discloses an ether ester compound as well as a preparation method and application thereof in olefin polymerization. The ether ester compound is shown as a formula M, wherein R1 is selected from hydrogen or C1-C18 alkyl; r2 is selected from alkyl groups of C1 to C18; r is selected from C1-C18 alkyl groups, C6-C30 aryl groups containing or not containing substituent groups, C7-C30 aralkyl groups containing or not containing substituent groups, and C5-C30 cycloalkyl groups containing or not containing substituent groups. The ether ester compound can be applied to olefin polymerization reaction, for example, as an internal electron donor of an olefin polymerization catalyst. The ether ester compound provided by the invention can be prepared from cheap and easily available raw materials, and the preparation method is simple and mild in conditions. The catalyst using the ether ester compound shows higher activity in propylene polymerization reaction, and the obtained polymer has higher isotactic index. # imgabs0 #

Description

Technical Field

[0001] The invention relates to an ether ester compound, in particular to an ether ester compound and a preparation method thereof and application thereof in olefin polymerization. Background Art

[0002] The development of the polyolefin industry depends critically on the preparation technology of polymerization catalysts. In the 1950s, Italian professor Natta invented the Ziegler-Natta catalyst (ZN catalyst) for the production of isotactic polypropylene. At present, the polypropylene catalyst used in industrial production is still dominated by the efficient ZN catalyst system. During the catalyst preparation and polymerization reaction, an electron-rich Lewis base compound, i.e., an electron donor compound, needs to be added. The addition of electron donor compounds can improve the stereoselectivity and activity of the catalyst, control the relative molecular weight and distribution of the polymer, and optimize the various performance indicators of the catalyst, thereby ultimately achieving the effect of regulating the performance of the polymer. Depending on the different ways of addition during use, electron donor compounds can be divided into internal electron donor compounds and external electron donor compounds. The internal electron donor is added during the preparation of the solid component of the catalyst, and the external electron donor is added as one of the components of the catalyst system during the olefin polymerization process.

[0003] Since the discovery of ZN catalyst, polypropylene catalyst has developed from the first generation to the fifth generation. The progress and upgrading of catalyst technology are due to the use of new electron donor compounds. Therefore, finding an ideal electron donor compound has always been a hot topic in the research of polypropylene catalysts. Among them, internal electron donor compounds play a pivotal role in improving catalyst performance and increasing polymer stereoregularity. It can be said that internal electron donors are the core of polypropylene catalysts. At present, the fourth generation catalyst is the most widely used in the industrial production of polypropylene, and its internal electron donor is the aromatic diester compound phthalic acid diester. Usually di-n-butyl phthalate (DNBP) and diisobutyl phthalate (DIBP) are used. The catalyst containing phthalic acid diester compounds has low activity, and the molecular weight distribution of the obtained polymer is not wide. During polymerization, it needs to be used in conjunction with external electron donors to achieve high catalytic activity and obtain polymers with higher isotacticity.

[0004] In the 1990s, Himont Company disclosed a class of 1,3-diether electron donor compounds in Chinese patent CN1041752A. Using a catalyst containing 1,3-diether compounds, high isotactic polypropylene can be obtained with high catalytic activity without adding an external electron donor during the polymerization process, which reduces the complexity of the reaction system.

[0005] However, although the catalysts using 1,3-diether electron donors have high activity and good hydrogen sensitivity, the relative molecular weight distribution of the resulting polymer is narrow, which is not conducive to the processing of the polymer. In addition, 1,3-diether compounds are prepared by O-alkylation of the corresponding 1,3-diols. The synthesis process of the intermediate compound 1,3-diol involved in the preparation process is complex and has a low yield. The O-alkylation reaction conditions are harsh and require the use of strong bases such as potassium tert-butoxide or sodium hydride for dehydrogenation. At the same time, the O-alkylation agent methyl iodide used is a highly toxic chemical. Summary of the invention

[0006] In view of the above problems in the prior art, the present invention provides an ether ester compound, and uses it as an internal electron donor in an olefin polymerization catalyst component, and further applies it to an olefin polymerization reaction. The preparation method of the ether ester compound is simple, the reaction conditions are mild, the operation is simple, and the raw materials are cheap and easy to obtain.

[0007] The first object of the present invention is to provide an ether ester compound, the structural formula of the ether ester compound is shown in Formula M:

[0008]

[0009] Among them, R 1 R is selected from hydrogen or C1-C18 alkyl; 2 Selected from C1-C18 alkyl; R is selected from C1-C18 alkyl, C6-C30 aryl with or without substituent, C7-C30 aralkyl with or without substituent, C5-C30 cycloalkyl with or without substituent.

[0010] Preferably, R 1 is selected from hydrogen or C1-C6 alkyl; and / or, R 2 and / or, R is selected from C1-C6 alkyl, C6-C20 aryl with or without substituent, C7-C20 aralkyl with or without substituent, C5-C20 cycloalkyl with or without substituent.

[0011] More preferably, R 1 is selected from hydrogen or C1-C4 alkyl; and / or, R 2 selected from C1-C4 alkyl; and / or, R is selected from C1-C4 alkyl, C6-C10 aryl with or without substituent, C7-C10 aralkyl with or without substituent, C5-C10 cycloalkyl with or without substituent, that is, R is selected from one of C1-C4 alkyl, C6-C10 aryl with or without substituent, C7-C10 aralkyl with or without substituent, and C5-C10 cycloalkyl with or without substituent.

[0012] More preferably, R1 is selected from hydrogen or methyl or ethyl; and / or,

[0013] R 2 is selected from methyl or ethyl; and / or, R is selected from C1-C3 alkyl, phenyl with or without substituents, naphthyl with or without substituents, benzyl with or without substituents, phenethyl with or without substituents, cyclohexyl with or without substituents.

[0014] According to the present invention, in formula M, R 1 Selected from hydrogen or C1-C18 alkyl, preferably hydrogen or C1-C6 alkyl, more preferably hydrogen or C1-C4 alkyl, most preferably hydrogen or methyl or ethyl;

[0015] R 2 An alkyl group selected from C1-C18, preferably a C1-C6 alkyl group, more preferably a C1-C4 alkyl group, most preferably a methyl group or an ethyl group;

[0016] R is selected from C1-C18 alkyl, C6-C30 aryl which may be substituted, C7-C30 aralkyl which may be substituted, C5-C30 cycloalkyl which may be substituted, preferably C1-C6 alkyl, C6-C20 aryl which may be substituted, C7-C20 aralkyl which may be substituted, C5-C20 cycloalkyl which may be substituted, more preferably C1-C4 alkyl, C6-C10 aryl which may be substituted, C7-C10 aralkyl which may be substituted, C5-C10 cycloalkyl which may be substituted, most preferably C1-C3 alkyl, phenyl which may be substituted, naphthyl which may be substituted, benzyl which may be substituted, phenethyl which may be substituted, cyclohexyl which may be substituted.

[0017] In the present invention, it is preferred that the substituent is selected from one or more of C1-C18 alkyl, C1-C18 alkoxy, and halogen; preferably, the substituent is selected from one or more of C1-C6 alkyl, C1-C6 alkoxy, and halogen; more preferably, the substituent is selected from one or more of C1-C4 alkyl, C1-C4 alkoxy, chlorine, and bromine; further more preferably, the substituent is selected from one or more of methyl, ethyl, methoxy, ethoxy, and chlorine.

[0018] The ether ester compound according to the present invention can be preferably selected from the following compounds: The ether ester compound is selected from the following compounds: 2-methoxyphenyl acetate, 2-methoxyphenyl propionate, 2-methoxyphenyl n-butyrate, 2-methoxyphenyl isobutyrate, 2-methoxyphenyl benzoate, 2-methoxyphenyl 2-ethoxybenzoate, 2-methoxyphenyl 2-methoxybenzoate, 2-methoxyphenyl 2-ethylbenzoate, 2-methoxyphenyl 2-methylbenzoate, 2-methoxyphenyl 2-chlorobenzoate, 2-methoxyphenyl 4-ethoxybenzoate, 2-methoxyphenyl 4-methoxybenzoate, 2-methoxyphenyl 4-ethylbenzoate, 2-methoxyphenyl 4-methylbenzoate, 2-methoxyphenyl 4-chlorobenzoate, 2-Methoxyphenyl trimethylbenzoate, 2-methoxyphenyl 1-naphthoic acid, 2-methoxyphenyl 2-phenylacetate, 2-methoxyphenyl 2-(2-ethoxyphenyl)acetate, 2-methoxyphenyl 2-(2-methoxyphenyl)acetate, 2-methoxyphenyl 2-(2-ethylphenyl)acetate, 2-methoxyphenyl 2-(2-methylphenyl)acetate, 2-methoxyphenyl 2-(2-chlorophenyl)acetate, 2-methoxyphenyl 2-(4-ethoxyphenyl)acetate, 2-methoxyphenyl 2-(4-methoxyphenyl)acetate, 2-methoxyphenyl 2-(4-ethylphenyl)acetate, 2-methoxyphenyl 2-(4-methylphenyl)acetate, 2-methoxyphenyl 2-(4-chlorophenyl)acetate, 3-phenyl 2-Methoxyphenyl propionate, 2-methoxyphenyl 3-(2-ethoxyphenyl) propionate, 2-methoxyphenyl 3-(2-methoxyphenyl) propionate, 2-methoxyphenyl 3-(2-ethylphenyl) propionate, 2-methoxyphenyl 3-(2-methylphenyl) propionate, 2-methoxyphenyl 3-(2-chlorophenyl) propionate, 2-methoxyphenyl 3-(4-ethoxyphenyl) propionate, 2-methoxyphenyl 3-(4-methoxyphenyl) propionate, 2-methoxyphenyl 3-(4-ethylphenyl) propionate, 2-methoxyphenyl 3-(4-methylphenyl) propionate, 2-methoxyphenyl 3-(4-chlorophenyl) propionate, 2-methoxyphenyl cyclohexanecarboxylate, 2-ethoxyphenyl acetate, 2-ethoxyphenyl propionate, butyric acid 2 -ethoxyphenyl ester, 2-ethoxyphenyl isobutyrate, 2-ethoxyphenyl benzoate, 2-ethoxyphenyl 2-ethoxybenzoate, 2-ethoxyphenyl 2-methoxybenzoate, 2-ethoxyphenyl 2-ethylbenzoate, 2-ethoxyphenyl 2-methylbenzoate, 2-ethoxyphenyl 2-chlorobenzoate, 2-ethoxyphenyl 4-ethoxybenzoate, 2-ethoxyphenyl 4-methoxybenzoate, 2-ethoxyphenyl 4-ethylbenzoate, 2-ethoxyphenyl 4-methylbenzoate, 2-ethoxyphenyl 4-chlorobenzoate, 2-ethoxyphenyl 2,4,6-trimethylbenzoate, 2-ethoxyphenyl 1-naphthoic acid, 2-ethoxyphenyl 2-phenylacetate, 2-ethoxyphenyl 2-(2-ethoxyphenyl)acetate,2-ethoxyphenyl 2-(2-methoxyphenyl)acetate, 2-ethoxyphenyl 2-(2-ethylphenyl)acetate, 2-ethoxyphenyl 2-(2-methylphenyl)acetate, 2-ethoxyphenyl 2-(2-chlorophenyl)acetate, 2-ethoxyphenyl 2-(4-ethoxyphenyl)acetate, 2-ethoxyphenyl 2-(4-methoxyphenyl)acetate, 2-ethoxyphenyl 2-(4-ethylphenyl)acetate, 2-ethoxyphenyl 2-(4-methylphenyl)acetate, 2-ethoxyphenyl 2-(4-chlorophenyl)acetate, 2-ethoxyphenyl 3-phenylpropanoate, 2-ethoxyphenyl 3-(2-ethoxyphenyl)propanoate, 2-ethoxyphenyl 3-(2-methoxyphenyl)propanoate, 3-(2-ethyl 2-ethoxyphenyl 3-(2-methylphenyl)propionate, 2-ethoxyphenyl 3-(2-chlorophenyl)propionate, 2-ethoxyphenyl 3-(4-ethoxyphenyl)propionate, 2-ethoxyphenyl 3-(4-methoxyphenyl)propionate, 2-ethoxyphenyl 3-(4-ethylphenyl)propionate, 2-ethoxyphenyl 3-(4-methylphenyl)propionate, 2-ethoxyphenyl 3-(4-methylphenyl)propionate, 2-ethoxyphenyl 3-(4-chlorophenyl)propionate, 2-ethoxyphenyl cyclohexanecarboxylate, 2-methoxy-4-methylphenyl acetate, 2-methoxy-4-methylphenyl propionate, 2-methoxy-4-methylphenyl butyrate, 2-methoxy-4-methylphenyl isobutyrate, 2-methoxy-4-methylphenyl benzoate, 2-methoxy-4-methylphenyl benzoate, 2-Methoxy-4-methylphenyl ethoxybenzoate, 2-methoxy-4-methylphenyl 2-methoxybenzoate, 2-methoxy-4-methylphenyl 2-ethylbenzoate, 2-methoxy-4-methylphenyl 2-methylbenzoate, 2-methoxy-4-methylphenyl 2-chlorobenzoate, 2-methoxy-4-methylphenyl 4-ethoxybenzoate, 2-methoxy-4-methylphenyl 4-methoxybenzoate, 2-methoxy-4-methylphenyl 4-ethylbenzoate, 2-methoxy-4-methylphenyl 4-methylbenzoate, 2-methoxy-4-methylphenyl 4-chlorobenzoate, 2-methoxy-4-methylphenyl 2,4,6-trimethylbenzoate, 2-methoxy-4-methylphenyl 1-naphthoate, 2- 2-methoxy-4-methylphenyl phenylacetate, 2-methoxy-4-methylphenyl 2-(2-ethoxyphenyl)acetate, 2-methoxy-4-methylphenyl 2-(2-methoxyphenyl)acetate, 2-methoxy-4-methylphenyl 2-(2-ethylphenyl)acetate, 2-methoxy-4-methylphenyl 2-(2-methylphenyl)acetate, 2-methoxy-4-methylphenyl 2-(2-chlorophenyl)acetate, 2-methoxy-4-methylphenyl 2-(4-ethoxyphenyl)acetate, 2-methoxy-4-methylphenyl 2-(4-methoxyphenyl)acetate, 2-methoxy-4-methylphenyl 2-(4-ethylphenyl)acetate, 2-methoxy-4-methylphenyl 2-(4-methylphenyl)acetate,2-methoxy-4-methylphenyl 2-(4-chlorophenyl)acetate, 2-methoxy-4-methylphenyl 3-phenylpropionate, 2-methoxy-4-methylphenyl 3-(2-ethoxyphenyl)propionate, 2-methoxy-4-methylphenyl 3-(2-methoxyphenyl)propionate, 2-methoxy-4-methylphenyl 3-(2-ethylphenyl)propionate, 2-methoxy-4-methylphenyl 3-(2-methylphenyl)propionate, 2-methoxy-4-methylphenyl 3-(2-chlorophenyl)propionate, 2-methoxy-4-methylphenyl 3-(4-ethoxyphenyl)propionate, 2-methoxy-4-methylphenyl 3-(4-methoxyphenyl)propionate, 2-methoxy-4-methylphenyl 3-(4-ethylphenyl)propionate ester, 2-methoxy-4-methylphenyl 3-(4-methylphenyl)propionate, 2-methoxy-4-methylphenyl 3-(4-chlorophenyl)propionate, 2-methoxy-4-methylphenyl cyclohexanecarboxylate, 2-ethoxy-4-methylphenyl acetate, 2-ethoxy-4-methylphenyl propionate, 2-ethoxy-4-methylphenyl butyrate, 2-ethoxy-4-methylphenyl isobutyrate, 2-ethoxy-4-methylphenyl benzoate, 2-ethoxy-4-methylphenyl 2-ethoxybenzoate, 2-ethoxy-4-methylphenyl 2-methoxybenzoate, 2-ethoxy-4-methylphenyl 2-ethylbenzoate, 2-ethoxy-4-methylphenyl 2-methylbenzoate, 2-ethoxy-4-methylphenyl 2-chlorobenzoate phenyl ester, 2-ethoxy-4-methylphenyl 4-ethoxybenzoate, 2-ethoxy-4-methylphenyl 4-methoxybenzoate, 2-ethoxy-4-methylphenyl 4-ethylbenzoate, 2-ethoxy-4-methylphenyl 4-methylbenzoate, 2-ethoxy-4-methylphenyl 4-chlorobenzoate, 2-ethoxy-4-methylphenyl 2,4,6-trimethylbenzoate, 2-ethoxy-4-methylphenyl 1-naphthoic acid, 2-ethoxy-4-methylphenyl 2-phenylacetate, 2-ethoxy-4-methylphenyl 2-(2-ethoxyphenyl)acetate, 2-ethoxy-4-methylphenyl 2-(2-methoxyphenyl)acetate, 2-ethoxy-4-methylphenyl 2-(2-ethylphenyl)acetate, 2-ethoxy-4-methylphenyl-(2-methylphenyl)acetate, 2-ethoxy-4-methylphenyl-2-(2-chlorophenyl)acetate, 2-ethoxy-4-methylphenyl-2-(4-ethoxyphenyl)acetate, 2-ethoxy-4-methylphenyl-2-(4-methoxyphenyl)acetate, 2-ethoxy-4-methylphenyl-2-(4-ethylphenyl)acetate, 2-ethoxy-4-methylphenyl-2-(4-methylphenyl)acetate, 2-ethoxy-4-methylphenyl-2-(4-chlorophenyl)acetate, 2-ethoxy-4-methylphenyl-3-phenylpropanoate, 2-ethoxy-4-methylphenyl-3-(2-ethoxyphenyl)propanoate, 2-ethoxy-4-methylphenyl-3-(2-methoxyphenyl)propanoate,2-Ethoxy-4-methylphenyl 3-(2-ethylphenyl)propionate, 2-ethoxy-4-methylphenyl 3-(2-methylphenyl)propionate, 2-ethoxy-4-methylphenyl 3-(2-chlorophenyl)propionate, 2-ethoxy-4-methylphenyl 3-(4-ethoxyphenyl)propionate, 2-ethoxy-4-methylphenyl 3-(4-methoxyphenyl)propionate, 2-ethoxy-4-methylphenyl 3-(4-ethylphenyl)propionate, 2-ethoxy-4-methylphenyl 3-(4-methylphenyl)propionate, 2-ethoxy-4-methylphenyl 3-(4-chlorophenyl)propionate, 2-ethoxy-4-methylphenyl cyclohexanecarboxylate, 2-methoxy-4-ethylphenyl acetate, 2-methoxy-4-ethyl propionate phenyl ester, 2-methoxy-4-ethylphenyl butyrate, 2-methoxy-4-ethylphenyl isobutyrate, 2-methoxy-4-ethylphenyl benzoate, 2-methoxy-4-ethylphenyl 2-ethoxybenzoate, 2-methoxy-4-ethylphenyl 2-methoxybenzoate, 2-methoxy-4-ethylphenyl 2-ethylbenzoate, 2-methoxy-4-ethylphenyl 2-methylbenzoate, 2-methoxy-4-ethylphenyl 2-chlorobenzoate, 2-methoxy-4-ethylphenyl 4-ethoxybenzoate, 2-methoxy-4-ethylphenyl 4-methoxybenzoate, 2-methoxy-4-ethylphenyl 4-ethylbenzoate, 2-methoxy-4-ethylphenyl 4-methylbenzoate, 2-methoxy-4-ethylphenyl 4-chlorobenzoate 2-methoxy-4-ethylphenyl ester, 2-methoxy-4-ethylphenyl 2,4,6-trimethylbenzoate, 2-methoxy-4-ethylphenyl 1-naphthoate, 2-methoxy-4-ethylphenyl 2-phenylacetate, 2-methoxy-4-ethylphenyl 2-(2-ethoxyphenyl)acetate, 2-methoxy-4-ethylphenyl 2-(2-methoxyphenyl)acetate, 2-methoxy-4-ethylphenyl 2-(2-ethylphenyl)acetate, 2-methoxy-4-ethylphenyl 2-(2-methylphenyl)acetate, 2-methoxy-4-ethylphenyl 2-(2-chlorophenyl)acetate, 2-methoxy-4-ethylphenyl 2-(4-ethoxyphenyl)acetate, 2-methoxy-4-ethylphenyl 2-(4-methoxyphenyl)acetate , 2-methoxy-4-ethylphenyl 2-(4-ethylphenyl)acetate, 2-methoxy-4-ethylphenyl 2-(4-methylphenyl)acetate, 2-methoxy-4-ethylphenyl 2-(4-chlorophenyl)acetate, 2-methoxy-4-ethylphenyl 3-phenylpropionate, 2-methoxy-4-ethylphenyl 3-(2-ethoxyphenyl)propionate, 2-methoxy-4-ethylphenyl 3-(2-methoxyphenyl)propionate, 2-methoxy-4-ethylphenyl 3-(2-ethylphenyl)propionate, 2-methoxy-4-ethylphenyl 3-(2-methylphenyl)propionate, 2-methoxy-4-ethylphenyl 3-(2-chlorophenyl)propionate, 2-methoxy-4-ethylphenyl 3-(4-ethoxyphenyl)propionate,2-methoxy-4-ethylphenyl 3-(4-methoxyphenyl)propionate, 2-methoxy-4-ethylphenyl 3-(4-ethylphenyl)propionate, 2-methoxy-4-ethylphenyl 3-(4-methylphenyl)propionate, 2-methoxy-4-ethylphenyl 3-(4-chlorophenyl)propionate, 2-methoxy-4-ethylphenyl cyclohexanecarboxylate, 2-ethoxy-4-ethylphenyl acetate, 2-ethoxy-4-ethylphenyl propionate, 2-ethoxy-4-ethylphenyl butyrate, 2-ethoxy-4-ethylphenyl isobutyrate, 2-ethoxy-4-ethylphenyl benzoate, 2-ethoxy-4-ethylphenyl 2-ethoxybenzoate, 2-ethoxy-4-ethylphenyl 2-methoxybenzoate, 2-ethoxy-2-ethylbenzoate 4-ethylphenyl ester, 2-ethoxy-4-ethylphenyl 2-methylbenzoate, 2-ethoxy-4-ethylphenyl 2-chlorobenzoate, 2-ethoxy-4-ethylphenyl 4-ethoxybenzoate, 2-ethoxy-4-ethylphenyl 4-methoxybenzoate, 2-ethoxy-4-ethylphenyl 4-ethylbenzoate, 2-ethoxy-4-ethylphenyl 4-methylbenzoate, 2-ethoxy-4-ethylphenyl 4-chlorobenzoate, 2-ethoxy-4-ethylphenyl 2,4,6-trimethylbenzoate, 2-ethoxy-4-ethylphenyl 1-naphthoic acid, 2-ethoxy-4-ethylphenyl 2-phenylacetate, 2-ethoxy-4-ethylphenyl 2-(2-ethoxyphenyl)acetate, 2-(2-methoxyphenyl)acetate 2-ethoxy-4-ethylphenyl 2-(2-ethylphenyl)acetate, 2-ethoxy-4-ethylphenyl 2-(2-methylphenyl)acetate, 2-ethoxy-4-ethylphenyl 2-(2-chlorophenyl)acetate, 2-ethoxy-4-ethylphenyl 2-(4-ethoxyphenyl)acetate, 2-ethoxy-4-ethylphenyl 2-(4-methoxyphenyl)acetate, 2-ethoxy-4-ethylphenyl 2-(4-ethylphenyl)acetate, 2-ethoxy-4-ethylphenyl 2-(4-methylphenyl)acetate, 2-ethoxy-4-ethylphenyl 2-(4-chlorophenyl)acetate, 2-ethoxy-4-ethylphenyl 3-phenylpropanoate, 2-ethoxy-4-ethylphenyl 3-(2-ethoxyphenyl)propanoate -ethylphenyl ester, 2-ethoxy-4-ethylphenyl 3-(2-methoxyphenyl) propionate, 2-ethoxy-4-ethylphenyl 3-(2-ethylphenyl) propionate, 2-ethoxy-4-ethylphenyl 3-(2-methylphenyl) propionate, 2-ethoxy-4-ethylphenyl 3-(2-chlorophenyl) propionate, 2-ethoxy-4-ethylphenyl 3-(4-ethoxyphenyl) propionate, 2-ethoxy-4-ethylphenyl 3-(4-methoxyphenyl) propionate, 2-ethoxy-4-ethylphenyl 3-(4-ethylphenyl) propionate, 2-ethoxy-4-ethylphenyl 3-(4-methylphenyl) propionate, 2-ethoxy-4-ethylphenyl 3-(4-chlorophenyl) propionate, 2-ethoxy-4-ethylphenyl cyclohexanecarboxylate. ,

[0019] The second object of the present invention is to provide a method for preparing the ether ester compound, comprising:

[0020] The para-substituted or unsubstituted o-alkoxyphenol represented by formula N and the acyl halide represented by formula S are subjected to an esterification reaction in a solvent under the action of an acid binding agent to obtain an ether ester compound represented by formula M;

[0021] In formula S, X is a halogen.

[0022] As an example, the ether ester compound according to the present invention can be obtained by the following preparation method:

[0023] The para-substituted or unsubstituted o-alkoxyphenol (Formula N) and the acyl chloride (Formula S) are reacted in an acid-binding agent (such as Et 3 N) in a solvent (such as THF) to carry out esterification reaction to obtain an ether ester compound as shown in formula M:

[0024]

[0025] According to the present invention, X is halogen, preferably, X is Cl.

[0026] In the present invention, the acid binding agent includes but is not limited to triethylamine.

[0027] According to the present invention, the molar ratio of the acid binding agent to the o-alkoxyphenol can be selected within a wide range. In a preferred embodiment of the present invention, the molar ratio of the acid binding agent to the o-alkoxyphenol is (1.3-1.7):1.

[0028] According to the present invention, the solvent includes but is not limited to tetrahydrofuran.

[0029] According to the present invention, the amount of the solvent can be selected within a wide range. In a preferred embodiment of the present invention, the amount of the solvent is 1-5 ml relative to 1 mmol of o-alkoxyphenol.

[0030] According to the present invention, the molar ratio of the o-alkoxyphenol to the acyl halide can be selected within a wide range. In a preferred embodiment of the present invention, the molar ratio of the o-alkoxyphenol to the acyl halide is 1:(0.8-1.2).

[0031] In a preferred embodiment of the present invention, the conditions of the esterification reaction include: reacting at a temperature of 15-80° C. (preferably the reflux temperature of the solvent) for 7-24 hours under a protective atmosphere; preferably, the preparation method includes:

[0032] Under a protective atmosphere (such as nitrogen and / or inert gas), the o-alkoxyphenol, the acid binding agent and the solvent are mixed, the solution containing the acyl halide is added dropwise at 10-20° C., and then refluxed at the reflux temperature of the solvent for 7-24 hours.

[0033] The third object of the present invention is to provide an application of the ether ester compound or the product obtained by the preparation method of the ether ester compound described above in olefin polymerization reaction.

[0034] For example, in the application, the ether ester compound is used as a component of an olefin polymerization catalyst. In this case, the ether ester compound acts as an internal electron donor in the solid component of the olefin polymerization catalyst. The above-mentioned olefin is preferably propylene, that is, the present invention provides the use of the ether ester compound according to the present invention in propylene polymerization, for example, the ether ester compound is used as an internal electron donor of a propylene polymerization catalyst, such as a Ziegler-Natta catalyst.

[0035] The ether ester compound provided by the present invention has a simple structure and can be obtained by esterification reaction of cheap and readily available raw material acyl chloride with para-substituted or unsubstituted o-alkoxyphenol. The preparation process has mild conditions, simple and safe operation, and avoids the use of highly toxic chemicals.

[0036] The ether ester compound according to the present invention can be used as a novel internal electron donor in an olefin polymerization catalyst, and further in the polymerization reaction of olefins, especially propylene. The propylene polymerization catalyst using the ether ester compound of the present invention has high catalytic activity, and the polymer obtained by the polymerization reaction has high isotacticity. DETAILED DESCRIPTION

[0037] The present invention is described in detail below in conjunction with specific embodiments. It is necessary to point out that the following embodiments are only used to further illustrate the present invention and cannot be understood as limiting the scope of protection of the present invention. Some non-essential improvements and adjustments made to the present invention by those skilled in the art based on the contents of the present invention still fall within the scope of protection of the present invention.

[0038] The present invention will be further described below by means of specific examples, but the scope of the present invention is not limited thereto.

[0039] Test Method

[0040] Nuclear magnetic resonance measurement: measured using a Bruker DMX300 nuclear magnetic resonance instrument 1 H-NMR (300 MHz, solvent CDCl 3 , TMS as internal standard, measurement temperature 300K).

[0041] Isotactic index of polymer: It is determined by heptane extraction method (extraction with boiling heptane for 6 hours): 2 grams of dry polymer sample is placed in an extractor and extracted with boiling heptane for 6 hours. The residue is dried to constant weight. The ratio of the obtained polymer weight (g) to 2 is the isotactic index.

[0042] Example 1

[0043] Preparation of ether ester compound (1)

[0044] The structural formula of the ether ester compound (1) is as follows:

[0045]

[0046] Ether ester compound (1) structure

[0047] Under nitrogen protection, add 20mmol of 2-methoxyphenol, 30mmol of triethylamine, and 20ml of tetrahydrofuran (THF) to a 250ml three-necked flask and stir to mix. Cool to 10°C in an ice bath, and add 10ml of THF solution of 20mmol of acetyl chloride at 10-20°C. After the addition is complete, remove the ice bath and naturally warm to room temperature. Heat to the reflux temperature of THF and reflux for 7-24 hours, and monitor the reaction by TLC. After the reaction is complete, cool to room temperature. Add 30ml of water for washing, separate the liquids, extract the aqueous phase twice with 25ml*2 ether, and combine the organic phases. Wash with 30ml of 1N HCl, and then with 50ml of saturated NaHCO 3 The organic phase was washed with 10 g of anhydrous Na 2 SO 4 The residue was dried, concentrated in vacuo to remove the solvent, and purified by column chromatography to obtain the target ether ester compound (1).

[0048] Then, use 1 The structure of the synthesized ether ester compound (1) was confirmed by H NMR as follows:

[0049] 1 H NMR (300 MHz, CDCl 3 , TMS as internal standard, δ / ppm): 6.91-7.22 (m, 4H), 3.82 (s, 3H), 2.31 (s, 3H).

[0050] Example 2

[0051] Preparation of ether ester compound (2)

[0052] According to the method of Example 1, 2-methoxyphenol is reacted with benzoyl chloride to generate R 1 is hydrogen, R 2 is a methyl group, R is a phenyl group, and an ether ester compound (2) is used1 Its structure was confirmed by H NMR (see Table 1 for details).

[0053] Example 3

[0054] Preparation of ether ester compound (3)

[0055] According to the method of Example 1, 2-methoxy-4-ethylphenol was reacted with 2-ethoxybenzoyl chloride to generate R 1 Ethyl, R 2 is a methyl group, R is a 2-ethoxyphenyl ether ester compound (3), and 1 Its structure was confirmed by H NMR (see Table 1 for details).

[0056] Example 4

[0057] Preparation of ether ester compound (4)

[0058] According to the method of Example 1, 2-methoxy-4-methylphenol was reacted with 2-methoxybenzoyl chloride to generate R 1 Methyl, R 2 is a methyl group, R is a 2-methoxyphenyl ether ester compound (4), and 1 Its structure was confirmed by H NMR (see Table 1 for details).

[0059] Example 5

[0060] Preparation of ether ester compound (5)

[0061] According to the method of Example 1, 2-methoxyphenol was reacted with 3-phenylpropionyl chloride to generate R 1 is hydrogen, R 2 is a methyl group, R is a phenethyl group, and an ether ester compound (5) is used 1 Its structure was confirmed by H NMR (see Table 1 for details).

[0062] Example 6

[0063] Preparation of ether ester compound (6)

[0064] According to the method of Example 1, 2-ethoxy-4-methylphenol was reacted with 2,4,6-trimethylbenzoyl chloride to generate R 1 Methyl, R 2 is an ether ester compound (6) in which R is ethyl and R is 2,4,6-trimethylphenyl, and 1 Its structure was confirmed by H NMR (see Table 1 for details).

[0065] Example 7

[0066] Preparation of ether ester compound (7)

[0067] According to the method of Example 1, 2-methoxy-4-ethylphenol was reacted with 1-naphthoyl chloride to generate R 1 Ethyl, R 2 is a methyl group, R is a 1-naphthyl group, and an ether ester compound (7) is used 1 Its structure was confirmed by H NMR (see Table 1 for details).

[0068] Example 8

[0069] Preparation of ether ester compound (8)

[0070] According to the method of Example 1, 2-methoxyphenol is reacted with 2-chlorobenzoyl chloride to generate R 1 is hydrogen, R 2 is a methyl group, R is a 2-chlorophenyl group ether ester compound (8), and 1 Its structure was confirmed by H NMR (see Table 1 for details).

[0071] Example 9

[0072] Preparation of ether ester compound (9)

[0073] According to the method of Example 1, 2-methoxyphenol is reacted with isobutyryl chloride to generate R 1 is hydrogen, R 2 is a methyl group, R is an isopropyl group, and an ether ester compound (9) is used 1 Its structure was confirmed by H NMR (see Table 1 for details).

[0074] Example 10

[0075] Preparation of ether ester compound (10)

[0076] According to the method of Example 1, 2-methoxyphenol is reacted with cyclohexylcarbonyl chloride to generate R 1 is hydrogen, R 2 is a methyl group, R is a cyclohexyl group, and an ether ester compound (10) is used 1 Its structure was confirmed by H NMR (see Table 1 for details).

[0077] Embodiment 11

[0078] Preparation of ether ester compound (11)

[0079] According to the method of Example 1, 2-methoxyphenol is reacted with n-butyryl chloride to generate R as shown in Formula M 1 is hydrogen, R 2 is a methyl group, R is a n-propyl group, and an ether ester compound (11) is used 1 Its structure was confirmed by H NMR (see Table 1 for details).

[0080] Table 1 Ether ester compounds

[0081]

[0082]

[0083] Example 12

[0084] Preparation of solid catalyst components

[0085] In a reactor fully replaced with high-purity nitrogen, add 4.8 g of magnesium chloride, 95 mL of toluene, 4 mL of epichlorohydrin, and 12.5 mL of tributyl phosphate in sequence, raise the temperature to 50°C under stirring, and maintain for 2.5 hours. Add 1.4 g of phthalic anhydride and continue to maintain for 1 hour. Cool the solution to below -25°C and add TiCl 4 56mL, slowly heated to 80°C, solids gradually precipitated during the heating process, 6mmol of ether ester compound (2) benzoic acid 2-methoxyphenyl ester prepared in Example 2 was added as an internal electron donor, and the temperature was maintained for 1h. After filtering, the mixture was washed twice with 70mL of toluene to obtain a solid precipitate. Then 60mL of toluene and TiCl 4 40mL, heat to 110℃, maintain for 2h, drain the filtrate, repeat the same operation once, then wash three times with 70mL of toluene at 110℃, each time for 10min, then add 60mL of hexane, wash twice to obtain the catalyst solid component.

[0086] Embodiment 13

[0087] Propylene polymerization

[0088] After the dry 250 mL three-necked flask was fully replaced with nitrogen and propylene, 100 mL of heptane was added, and after heating to 70°C, 2.0 mmol of AlEt 3 and 0.1mmol methylcyclohexyldimethoxysilane (CHMMS) to make Al / Si=20 (molar ratio), add 10mg of the catalyst solid component prepared in Example 12 (containing 3wt% of Ti element) at this temperature, react for 2h, and then terminate the reaction with ethanol. The obtained polymer is washed with anhydrous ethanol and then dried in a vacuum. The calculated catalyst activity is 198gPP / (gCat·2h), and the isotactic index of the polymer is 97.6%. It can be seen that the ether ester compound of the present invention is used as a propylene polymerization catalyst component, and the propylene polymerization catalyst has a high catalytic activity, and the isotacticity of the polymer obtained by the polymerization reaction is high.

[0089] It has been verified that the ether ester compounds in Example 1 and Examples 3-11 of the present invention are used as catalyst components for propylene polymerization. The propylene polymerization catalyst has high catalytic activity, and the polymer obtained by the polymerization reaction has high isotacticity.

[0090] It should be noted that the embodiments described above are only used to explain the present invention and do not constitute any limitation to the present invention. The present invention has been described with reference to typical embodiments, but it should be understood that the words used therein are descriptive and explanatory words, rather than restrictive words. The present invention may be modified as specified within the scope of the claims of the present invention, and the present invention may be revised without departing from the scope and spirit of the present invention. Although the present invention described therein relates to specific methods, materials and embodiments, it does not mean that the present invention is limited to the specific examples disclosed therein, on the contrary, the present invention can be extended to all other methods and applications with the same functions.

[0091] All publications, patent applications, patents and other references mentioned in this specification are incorporated herein by reference. Unless otherwise defined, all technical and scientific terms used in this specification have the meanings conventionally understood by those skilled in the art. In the event of a conflict, the definition in this specification shall prevail.

[0092] When this specification uses the prefix "well-known to those skilled in the art", "prior art" or similar terms to introduce materials, substances, methods, steps, devices or components, etc., the objects introduced by the prefix cover those commonly used in the art when this application is filed, but also include those that are not commonly used at present but will become recognized in the art as being suitable for similar purposes.

[0093] The endpoints and any values ​​of the scope disclosed in the present application document are not limited to the precise scope or value, and these scopes or values ​​should be understood to include values ​​close to these scopes or values. For numerical ranges, between the endpoint values ​​of each scope, between the endpoint values ​​of each scope and a separate point value, and between separate point values, one or more new numerical ranges can be combined with each other, and these numerical ranges should be considered as specifically disclosed in this article. Hereinafter, in principle, each technical solution can be combined with each other to obtain a new technical solution, which should also be considered as specifically disclosed in this article.

[0094] In the context of the present specification, any matters or items not mentioned are directly applicable to those known in the art without any changes except those explicitly stated.

[0095] Moreover, any embodiment described in this document may be freely combined with one or more other embodiments described in this document, and the technical solutions or technical ideas formed thereby are deemed to be part of the original disclosure or original record of the present invention, and should not be regarded as new content that has not been disclosed or anticipated in this document, unless a person skilled in the art considers that the combination is obviously unreasonable.

Claims

1. An ether ester compound, the structural formula of the ether ester compound is shown in Formula M: in, R 1 R is selected from hydrogen or C1-C18 alkyl; 2 Selected from C1-C18 alkyl; R is selected from C1-C18 alkyl, C6-C30 aryl with or without substituent, C7-C30 aralkyl with or without substituent, C5-C30 cycloalkyl with or without substituent.

2. The ether ester compound according to claim 1, characterized in that R 1 is selected from hydrogen or C1-C6 alkyl; and / or, R 2 an alkyl group selected from C1-C6; and / or, R is selected from C1-C6 alkyl, C6-C20 aryl which may be substituted, C7-C20 aralkyl which may be substituted, and C5-C20 cycloalkyl which may be substituted.

3. The ether ester compound according to claim 1, characterized in that R 1 is selected from hydrogen or C1-C4 alkyl; and / or, R 2 an alkyl group selected from C1-C4; and / or, R is selected from C1-C4 alkyl, C6-C10 aryl which may be substituted, C7-C10 aralkyl which may be substituted, and C5-C10 cycloalkyl which may be substituted.

4. The ether ester compound according to claim 1, characterized in that R 1 is selected from hydrogen or methyl or ethyl; and / or, R 2 is selected from methyl or ethyl; and / or, R is selected from C1-C3 alkyl, phenyl which may be substituted, naphthyl which may be substituted, benzyl which may be substituted, phenethyl which may be substituted, and cyclohexyl which may be substituted.

5. The ether ester compound according to any one of claims 1 to 4, characterized in that The substituent is selected from one or more of C1-C18 alkyl, C1-C18 alkoxy, and halogen; preferably, The substituent is selected from one or more of C1-C6 alkyl, C1-C6 alkoxy, and halogen; more preferably, The substituent is selected from one or more of C1-C4 alkyl, C1-C4 alkoxy, chlorine, and bromine; more preferably, The substituent is selected from one or more of methyl, ethyl, methoxy, ethoxy and chlorine.

6. The ether ester compound according to claim 1, characterized in that The ether ester compound is selected from the following compounds: 2-methoxyphenyl acetate, 2-methoxyphenyl propionate, 2-methoxyphenyl n-butyrate, 2-methoxyphenyl isobutyrate, 2-methoxyphenyl benzoate, 2-methoxyphenyl 2-ethoxybenzoate, 2-methoxyphenyl 2-methoxybenzoate, 2-methoxyphenyl 2-ethylbenzoate, 2-methoxyphenyl 2-methylbenzoate, 2-methoxyphenyl 2-chlorobenzoate, 2-methoxyphenyl 4-ethoxybenzoate, 2-methoxyphenyl 4-methoxybenzoate, 2-methoxyphenyl 4-ethylbenzoate, 2-methoxyphenyl 4-methylbenzoate, 2-methoxyphenyl 4-chlorobenzoate, 2-methoxyphenyl 2,4,6-trimethylbenzoate, 2-methoxyphenyl 1-naphthoate, 2-Methoxyphenyl 2-phenylacetate, 2-methoxyphenyl 2-(2-ethoxyphenyl)acetate, 2-methoxyphenyl 2-(2-methoxyphenyl)acetate, 2-methoxyphenyl 2-(2-ethylphenyl)acetate, 2-methoxyphenyl 2-(2-methylphenyl)acetate, 2-methoxyphenyl 2-(2-chlorophenyl)acetate, 2-methoxyphenyl 2-(4-ethoxyphenyl)acetate, 2-methoxyphenyl 2-(4-methoxyphenyl)acetate, 2-methoxyphenyl 2-(4-ethylphenyl)acetate, 2-methoxyphenyl 2-(4-methylphenyl)acetate, 2-methoxyphenyl 2-(4-chlorophenyl)acetate, 2-methoxyphenyl 3-phenylpropanoate, 3-(2-ethoxyphenyl)propanoate 2-Methoxyphenyl 3-(2-methoxyphenyl)propionate, 2-methoxyphenyl 3-(2-ethylphenyl)propionate, 2-methoxyphenyl 3-(2-methylphenyl)propionate, 2-methoxyphenyl 3-(2-chlorophenyl)propionate, 2-methoxyphenyl 3-(4-ethoxyphenyl)propionate, 2-methoxyphenyl 3-(4-methoxyphenyl)propionate, 2-methoxyphenyl 3-(4-ethylphenyl)propionate, 2-methoxyphenyl 3-(4-methylphenyl)propionate, 2-methoxyphenyl 3-(4-chlorophenyl)propionate, 2-methoxyphenyl cyclohexanecarboxylate, 2-ethoxyphenyl acetate, 2-ethoxyphenyl propionate, 2-ethoxyphenyl butyrate, 2-ethoxyphenyl isobutyrate, 2-methoxyphenyl benzoate 2-ethoxyphenyl 2-ethoxybenzoate, 2-ethoxyphenyl 2-methoxybenzoate, 2-ethoxyphenyl 2-ethylbenzoate, 2-ethoxyphenyl 2-methylbenzoate, 2-ethoxyphenyl 2-chlorobenzoate, 2-ethoxyphenyl 4-ethoxybenzoate, 2-ethoxyphenyl 4-methoxybenzoate, 2-ethoxyphenyl 4-ethylbenzoate, 2-ethoxyphenyl 4-methylbenzoate, 2-ethoxyphenyl 4-chlorobenzoate, 2-ethoxyphenyl 2,4,6-trimethylbenzoate, 2-ethoxyphenyl 1-naphthoic acid, 2-ethoxyphenyl 2-phenylacetate, 2-ethoxyphenyl 2-(2-ethoxyphenyl)acetate, 2-ethoxyphenyl 2-(2-methoxyphenyl)acetate,2-ethoxyphenyl 2-(2-ethylphenyl)acetate, 2-ethoxyphenyl 2-(2-methylphenyl)acetate, 2-ethoxyphenyl 2-(2-chlorophenyl)acetate, 2-ethoxyphenyl 2-(4-ethoxyphenyl)acetate, 2-ethoxyphenyl 2-(4-methoxyphenyl)acetate, 2-ethoxyphenyl 2-(4-ethylphenyl)acetate, 2-ethoxyphenyl 2-(4-methylphenyl)acetate, 2-ethoxyphenyl 2-(4-chlorophenyl)acetate, 2-ethoxyphenyl 3-phenylpropanoate, 2-ethoxyphenyl 3-(2-ethoxyphenyl)propanoate, 2-ethoxyphenyl 3-(2-methoxyphenyl)propanoate, 2-ethoxyphenyl 3-(2-ethylphenyl)propanoate, 2-ethoxyphenyl 3-(2-methylphenyl)propanoate Ethoxyphenyl ester, 2-ethoxyphenyl 3-(2-chlorophenyl) propionate, 2-ethoxyphenyl 3-(4-ethoxyphenyl) propionate, 2-ethoxyphenyl 3-(4-methoxyphenyl) propionate, 2-ethoxyphenyl 3-(4-ethylphenyl) propionate, 2-ethoxyphenyl 3-(4-methylphenyl) propionate, 2-ethoxyphenyl 3-(4-chlorophenyl) propionate, 2-ethoxyphenyl cyclohexanecarboxylate, 2-methoxy-4-methylphenyl acetate, 2-methoxy-4-methylphenyl propionate, 2-methoxy-4-methylphenyl butyrate, 2-methoxy-4-methylphenyl isobutyrate, 2-methoxy-4-methylphenyl benzoate, 2-methoxy-4-methylphenyl 2-ethoxybenzoate, 2-methoxy-4-methylphenyl 2-methoxybenzoate 2-methoxy-4-methylphenyl 2-ethylbenzoate, 2-methoxy-4-methylphenyl 2-methylbenzoate, 2-methoxy-4-methylphenyl 2-chlorobenzoate, 2-methoxy-4-methylphenyl 4-ethoxybenzoate, 2-methoxy-4-methylphenyl 4-methoxybenzoate, 2-methoxy-4-methylphenyl 4-ethylbenzoate, 2-methoxy-4-methylphenyl 4-methylbenzoate, 2-methoxy-4-methylphenyl 4-chlorobenzoate, 2-methoxy-4-methylphenyl 2,4,6-trimethylbenzoate, 2-methoxy-4-methylphenyl 1-naphthoic acid, 2-methoxy-4-methylphenyl 2-phenylacetate, 2-methoxy-4-methylphenyl 2-(2-ethoxyphenyl)acetate 2-methoxy-4-methylphenyl 2-(2-methoxyphenyl)acetate, 2-methoxy-4-methylphenyl 2-(2-ethylphenyl)acetate, 2-methoxy-4-methylphenyl 2-(2-methylphenyl)acetate, 2-methoxy-4-methylphenyl 2-(2-chlorophenyl)acetate, 2-methoxy-4-methylphenyl 2-(4-ethoxyphenyl)acetate, 2-methoxy-4-methylphenyl 2-(4-methoxyphenyl)acetate, 2-methoxy-4-methylphenyl 2-(4-ethylphenyl)acetate, 2-methoxy-4-methylphenyl 2-(4-methylphenyl)acetate, 2-methoxy-4-methylphenyl 2-(4-chlorophenyl)acetate, 2-methoxy-4-methylphenyl 3-phenylpropanoate,2-Methoxy-4-methylphenyl 3-(2-ethoxyphenyl)propionate, 2-methoxy-4-methylphenyl 3-(2-methoxyphenyl)propionate, 2-methoxy-4-methylphenyl 3-(2-ethylphenyl)propionate, 2-methoxy-4-methylphenyl 3-(2-methylphenyl)propionate, 2-methoxy-4-methylphenyl 3-(2-chlorophenyl)propionate, 2-methoxy-4-methylphenyl 3-(4-ethoxyphenyl)propionate, 2-methoxy-4-methylphenyl 3-(4-methoxyphenyl)propionate, 2-methoxy-4-methylphenyl 3-(4-ethylphenyl)propionate, 2-methoxy-4-methylphenyl 3-(4-methylphenyl)propionate, 2-methoxy-4-methylphenyl 3-(4-chlorophenyl)propionate, 2-ethoxy-4-methylphenyl ester, cyclohexanecarboxylic acid 2-methoxy-4-methylphenyl ester, acetic acid 2-ethoxy-4-methylphenyl ester, propionic acid 2-ethoxy-4-methylphenyl ester, butyric acid 2-ethoxy-4-methylphenyl ester, isobutyric acid 2-ethoxy-4-methylphenyl benzoate, 2-ethoxy-4-methylphenyl 2-ethoxybenzoate, 2-methoxy-4-methylphenyl ester, 2-ethoxy-4-methylphenyl 2-ethylbenzoate, 2-ethoxy-4-methylphenyl 2-methylbenzoate, 2-ethoxy-4-methylphenyl 2-chlorobenzoate, 4-ethoxy-4-methylphenyl 2-ethoxybenzoate, 4-methoxybenzoic acid 2-ethoxy-4-methylphenyl ester, 2-Ethoxy-4-methylphenyl ethylbenzoate, 2-Ethoxy-4-methylphenyl 4-methylbenzoate, 2-Ethoxy-4-methylphenyl 4-chlorobenzoate, 2-Ethoxy-4-methylphenyl 2,4,6-trimethylbenzoate, 2-Ethoxy-4-methylphenyl 1-naphthoic acid, 2-Ethoxy-4-methylphenyl 2-phenylacetate, 2-Ethoxy-4-methylphenyl 2-(2-ethoxyphenyl)acetate, 2-Ethoxy-4-methylphenyl 2-(2-methoxyphenyl)acetate, 2-Ethoxy-4-methylphenyl 2-(2-ethylphenyl)acetate, 2-Ethoxy-4-methylphenyl 2-(2-methylphenyl)acetate, 2-Ethoxy-4-methylphenyl 2-(2-chlorophenyl)acetate, 2 2-ethoxy-4-methylphenyl-(4-ethoxyphenyl)acetate, 2-ethoxy-4-methylphenyl-2-(4-methoxyphenyl)acetate, 2-ethoxy-4-methylphenyl-2-(4-ethylphenyl)acetate, 2-ethoxy-4-methylphenyl-2-(4-methylphenyl)acetate, 2-ethoxy-4-methylphenyl-2-(4-chlorophenyl)acetate, 2-ethoxy-4-methylphenyl-3-phenylpropionate, 2-ethoxy-4-methylphenyl-3-(2-ethoxyphenyl)propionate, 2-ethoxy-4-methylphenyl-3-(2-methoxyphenyl)propionate, 2-ethoxy-4-methylphenyl-3-(2-ethylphenyl)propionate, 2-ethoxy-4-methylphenyl-3-(2-methylphenyl)propionate,2-ethoxy-4-methylphenyl 3-(2-chlorophenyl)propionate, 2-ethoxy-4-methylphenyl 3-(4-ethoxyphenyl)propionate, 2-ethoxy-4-methylphenyl 3-(4-methoxyphenyl)propionate, 2-ethoxy-4-methylphenyl 3-(4-ethylphenyl)propionate, 2-ethoxy-4-methylphenyl 3-(4-methylphenyl)propionate, 2-ethoxy-4-methylphenyl 3-(4-chlorophenyl)propionate, 2-ethoxy-4-methylphenyl cyclohexanecarboxylate, 2-methoxy-4-ethylphenyl acetate, 2-methoxy-4-ethylphenyl propionate, 2-methoxy-4-ethylphenyl butyrate, 2-methoxy-4-ethylphenyl isobutyrate, 2-methoxy-4-ethylphenyl benzoate, 2-Methoxy-4-ethylphenyl 2-ethoxybenzoate, 2-methoxy-4-ethylphenyl 2-methoxybenzoate, 2-methoxy-4-ethylphenyl 2-ethylbenzoate, 2-methoxy-4-ethylphenyl 2-methylbenzoate, 2-methoxy-4-ethylphenyl 2-chlorobenzoate, 2-methoxy-4-ethylphenyl 4-ethoxybenzoate, 2-methoxy-4-ethylphenyl 4-methoxybenzoate, 2-methoxy-4-ethylphenyl 4-ethylbenzoate, 2-methoxy-4-ethylphenyl 4-methylbenzoate, 2-methoxy-4-ethylphenyl 4-chlorobenzoate, 2-methoxy-4-ethylphenyl 2,4,6-trimethylbenzoate, 2-methoxy-4-ethylphenyl 1-naphthoate, 2 2-methoxy-4-ethylphenyl-2-phenylacetate, 2-methoxy-4-ethylphenyl-2-(2-ethoxyphenyl)acetate, 2-methoxy-4-ethylphenyl-2-(2-methoxyphenyl)acetate, 2-methoxy-4-ethylphenyl-2-(2-ethylphenyl)acetate, 2-methoxy-4-ethylphenyl-2-(2-methylphenyl)acetate, 2-methoxy-4-ethylphenyl-2-(2-chlorophenyl)acetate, 2-methoxy-4-ethylphenyl-2-(4-ethoxyphenyl)acetate, 2-methoxy-4-ethylphenyl-2-(4-methoxyphenyl)acetate, 2-methoxy-4-ethylphenyl-2-(4-ethylphenyl)acetate, 2-methoxy-4-ethylphenyl-2-(4-methylphenyl)acetate, 2-methoxy-4-ethylphenyl 2-(4-chlorophenyl)acetate, 2-methoxy-4-ethylphenyl 3-phenylpropionate, 2-methoxy-4-ethylphenyl 3-(2-ethoxyphenyl)propionate, 2-methoxy-4-ethylphenyl 3-(2-methoxyphenyl)propionate, 2-methoxy-4-ethylphenyl 3-(2-ethylphenyl)propionate, 2-methoxy-4-ethylphenyl 3-(2-methylphenyl)propionate, 2-methoxy-4-ethylphenyl 3-(2-chlorophenyl)propionate, 2-methoxy-4-ethylphenyl 3-(4-ethoxyphenyl)propionate, 2-methoxy-4-ethylphenyl 3-(4-methoxyphenyl)propionate, 2-methoxy-4-ethylphenyl 3-(4-ethylphenyl)propionate,2-Methoxy-4-ethylphenyl 3-(4-methylphenyl)propionate, 2-methoxy-4-ethylphenyl 3-(4-chlorophenyl)propionate, 2-methoxy-4-ethylphenyl cyclohexanecarboxylate, 2-ethoxy-4-ethylphenyl acetate, 2-ethoxy-4-ethylphenyl propionate, 2-ethoxy-4-ethylphenyl butyrate, 2-ethoxy-4-ethylphenyl isobutyrate, 2-ethoxy-4-ethylphenyl benzoate, 2-ethoxy-4-ethylphenyl 2-ethoxybenzoate, 2-ethoxy-4-ethylphenyl 2-methoxybenzoate, 2-ethoxy-4-ethylphenyl 2-ethylbenzoate, 2-ethoxy-4-ethylphenyl 2-methylbenzoate, 2-ethoxy-2-chlorobenzoate 4-ethylphenyl ester, 2-ethoxy-4-ethylphenyl 4-ethoxybenzoate, 2-ethoxy-4-ethylphenyl 4-methoxybenzoate, 2-ethoxy-4-ethylphenyl 4-ethylbenzoate, 2-ethoxy-4-ethylphenyl 4-methylbenzoate, 2-ethoxy-4-ethylphenyl 4-chlorobenzoate, 2-ethoxy-4-ethylphenyl 2,4,6-trimethylbenzoate, 2-ethoxy-4-ethylphenyl 1-naphthoic acid, 2-ethoxy-4-ethylphenyl 2-phenylacetate, 2-ethoxy-4-ethylphenyl 2-(2-ethoxyphenyl)acetate, 2-ethoxy-4-ethylphenyl 2-(2-methoxyphenyl)acetate, 2-ethoxy-4-ethylphenyl 2-(2-ethylphenyl)acetate 2-ethoxy-4-ethylphenyl 2-(2-methylphenyl)acetate, 2-ethoxy-4-ethylphenyl 2-(2-chlorophenyl)acetate, 2-ethoxy-4-ethylphenyl 2-(4-ethoxyphenyl)acetate, 2-ethoxy-4-ethylphenyl 2-(4-methoxyphenyl)acetate, 2-ethoxy-4-ethylphenyl 2-(4-ethylphenyl)acetate, 2-ethoxy-4-ethylphenyl 2-(4-methylphenyl)acetate, 2-ethoxy-4-ethylphenyl 2-(4-chlorophenyl)acetate, 2-ethoxy-4-ethylphenyl 3-phenylpropanoate, 2-ethoxy-4-ethylphenyl 3-(2-ethoxyphenyl)propanoate, 3-(2-methylphenyl)acetate 2-ethoxy-4-ethylphenyl 3-(2-ethylphenyl) propionate, 2-ethoxy-4-ethylphenyl 3-(2-methylphenyl) propionate, 2-ethoxy-4-ethylphenyl 3-(2-chlorophenyl) propionate, 2-ethoxy-4-ethylphenyl 3-(4-ethoxyphenyl) propionate, 2-ethoxy-4-ethylphenyl 3-(4-methoxyphenyl) propionate, 2-ethoxy-4-ethylphenyl 3-(4-ethylphenyl) propionate, 2-ethoxy-4-ethylphenyl 3-(4-methylphenyl) propionate, 2-ethoxy-4-ethylphenyl 3-(4-chlorophenyl) propionate, 2-ethoxy-4-ethylphenyl cyclohexanecarboxylate. , 7. A method for preparing the ether ester compound according to any one of claims 1 to 6, comprising: The para-substituted or unsubstituted o-alkoxyphenol represented by formula N and the acyl halide represented by formula S are subjected to an esterification reaction in a solvent under the action of an acid binding agent to obtain an ether ester compound represented by formula M; In formula S, X is a halogen.

8. The preparation method according to claim 7, characterized in that: X is Cl; and / or, The molar ratio of the acid binding agent to the o-alkoxyphenol is (1.3-1.7):1; and / or, The amount of the solvent used is 1-5 ml relative to 1 mmol of o-alkoxyphenol; and / or, The molar ratio of the o-alkoxyphenol to the acyl halide is 1:(0.8-1.2).

9. The preparation method according to claim 7 or 8, characterized in that: The conditions of the esterification reaction include: reacting at a temperature of 15-80° C. for 7-24 hours under a protective atmosphere; preferably, the preparation method includes: Under a protective atmosphere, the o-alkoxyphenol, the acid binding agent and the solvent are mixed, the solution containing the acyl halide is added dropwise at 10-20° C., and then refluxed at the reflux temperature of the solvent for 7-24 hours.

10. Use of the ether ester compound according to any one of claims 1 to 6 or the product obtained by the preparation method according to any one of claims 7 to 9 in olefin polymerization reaction.

11. The use according to claim 10, characterized in that: In said application, the ether ester compound is used as a component of an olefin polymerization catalyst; Preferably, the olefin is propylene.

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