Compounds, processes for their preparation and their use

Abstract

The present application relates to the field of organic synthesis, disclose a compound and its preparation method and application, the compound has the structure shown in formula (I), wherein, in formula (I), R1 and R2 Same or different, each independently selected from C1-C 14 Alkyl group;R3 is selected from C1-C 10 Alkylene group, C3-C 10 Cycloalkylene group or C7-C 20 Aryl group;R4 is selected from C1-C 10 Alkyl group, C3-C 10 Cycloalkyl group or C7-C 20 Aryl group. When the catalyst component comprising the compound shown in formula (I) of the present application is used to carry out olefin (especially propylene) polymerization, the hydrogen sensitivity of the catalyst is very good, and the molecular weight distribution is relatively wide, which has great industrial application prospect.

Description

Technical Field

[0001] The present invention relates to the field of organic synthesis, and in particular to a compound, a preparation method of the compound, a compound prepared according to the preparation method, and application of the compound in olefin polymerization. Background Art

[0002] It is well known that Ziegler-Natta catalysts used in propylene polymerization consist of at least three components: a magnesium chloride support, an internal electron donor compound, and a titanium compound. The electron donor compound not only enhances catalyst activity but also strengthens the catalyst's stereospecificity. Without the internal electron donor compound, catalyst activity is low, and the resulting polymer is unusable due to its low isotactic index.

[0003] Internal electron donor compounds include aromatic monoesters or diesters such as diisobutyl phthalate or ethyl benzoate used in US Pat. No. 4,784,983, glycol esters such as used in CN 1,453,298A, succinates such as used in CN 1,313,869A, and diethers such as used in EP 361,494. In industrial production, each of these internal electron donor compounds has certain drawbacks in practical application: for example, catalysts using aromatic diesters have low catalytic activity; while catalysts using diethers have high catalytic activity and good hydrogen sensitivity, the resulting polymers have a narrow molecular weight distribution.

[0004] Because of the importance of internal electron donor compounds in catalysts and the shortcomings of current internal electron donor compounds in practical applications, the improvement of internal electron donor compounds remains a research hotspot in this field. Therefore, the development of new internal electron donor compounds for olefin polymerization catalysts that can overcome these shortcomings is of great significance. Summary of the Invention

[0005] The inventors of the present invention have found during research that when the compound of the present invention is used as a catalyst for synthesizing an internal electron donor compound for olefin polymerization, especially propylene polymerization, the catalyst has good hydrogen sensitivity and the resulting polymer has a wide molecular weight distribution.

[0006] The first aspect of the present invention provides a compound having a structure shown in formula (I):

[0007]

[0008] Wherein, in formula (I), R1 and R2 are the same or different and are independently selected from C1-C 14 R3 is selected from C1-C10 Alkylene, C3-C 10 Cycloalkylene or C7-C 20 Arylene; R4 is selected from C1-C 10 Alkyl, C3-C 10 Cycloalkyl or C7-C 20 Aryl.

[0009] A second aspect of the present invention provides a method for preparing a compound, the method comprising the following steps:

[0010] In the presence of a catalyst, reacting the compound represented by formula (II) with the compound represented by formula (III) to obtain the compound represented by formula (I);

[0011]

[0012]

[0013] Wherein, R1 and R2 are the same or different and are independently selected from C1-C 14 R3 is selected from C1-C 10 Alkylene, C3-C 10 Cycloalkylene or C7-C 20 Arylene; R4 is selected from C1-C 10 Alkyl, C3-C 10 Cycloalkyl or C7-C 20 Aryl; R5 and R6 are the same or different, each independently selected from C1-C 20 Alkyl, C3-C 20 Cycloalkyl and C6-C 20 One of the aromatic groups.

[0014] A third aspect of the present invention provides a method for preparing a compound, the method comprising the following steps:

[0015] (i) contacting the compound of formula (IV) with a metal alkoxide in a first aprotic solvent to obtain a reaction mixture,

[0016]

[0017] (ii) contacting the reaction mixture obtained in step (i) with the compound of formula (V) in a second aprotic solvent to obtain a compound of formula (II),

[0018]

[0019] (iii) reacting the compound represented by formula (II) with the compound represented by formula (III) in the presence of a catalyst to obtain the compound represented by formula (I);

[0020]

[0021] wherein R1 and R2 are the same or different, each independently selected from C1-C 14 alkyl; R3 is selected from C1-C 10 alkylene, C3-C 10 cycloalkylene or C7-C 20 arylene; R4 is selected from C1-C 10 alkyl, C3-C 10 cycloalkyl or C7-C 20 aryl; R5 and R6 are the same or different, each independently selected from one of C1-C 20 alkyl, C3-C 20 cycloalkyl and C6-C 20 aryl; X is halogen.

[0022] The fourth aspect of the present application provides a compound prepared according to the preparation method as described above.

[0023] The fifth aspect of the present application provides the use of the compound as described above in olefin polymerization.

[0024] When the compound of the present application is used as an internal electron donor compound, the synthesized catalyst is used in olefin polymerization, especially propylene polymerization, and the catalyst has good activity and hydrogen sensitivity, and can obtain a polymer with a wide molecular weight distribution. The molecular weight distribution has a significant influence on the performance of the polymer, and the widening of the molecular weight distribution can improve the mechanical properties and gloss of the polypropylene, and improve the processing performance, so the wide molecular weight distribution polypropylene has a better balance between mechanical properties and processing performance, which means that the compound of the present application and the catalyst prepared based thereon have a good industrial application prospect. DETAILED DESCRIPTION

[0025] The endpoints of the ranges and any values disclosed herein are not limited to the precise values stated. The endpoints of the ranges and any values are understood to be approximate values. The exact numerical values of the endpoints of the ranges and any values are approximations which are provided to convey the significance as precisely as possible. It is also understood that the endpoints of the ranges and any values are understood and are to be construed as specifically disclosed endpoints. Moreover, all ranges and values disclosed herein are multiplicative unless expressly indicated otherwise.

[0026] The first aspect of the present application provides a compound, which has a structure shown in formula (I):

[0027]

[0028] wherein in formula (I), R1 and R2 are the same or different, each independently selected from C1-C 14 alkyl; R3 is selected from C1-C10 Alkylene, C3-C 10 Cycloalkylene or C7-C 20 Arylene; R4 is selected from C1-C 10 Alkyl, C3-C 10 Cycloalkyl or C7-C 20 Aryl.

[0029] The alkyl group or alkylene group may be a branched or linear alkyl group or alkylene group.

[0030] Preferably, R1 and R2 are each independently selected from a C1-C5 alkyl group, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, or neopentyl. More preferably, they are each independently selected from a C3-C5 branched alkyl group, further preferably isopropyl, sec-butyl, or isobutyl. In this preferred embodiment, the catalyst prepared as an internal electron donor can further improve the catalyst's sensitivity to hydrogen modulation during olefin (especially propylene) polymerization, resulting in a wider molecular weight distribution of the obtained product.

[0031] Preferably, R3 is selected from C1-C5 alkylene groups, such as methylene, ethylene, n-propylene, isopropylene, n-butylene, sec-butylene, isobutylene, tert-butylene, n-pentylene, isopentylene, tert-pentylene or neopentylene, etc., more preferably selected from C1-C5 straight-chain alkylene groups, further preferably methylene, ethylene or n-propylene.

[0032] Preferably, R4 is selected from C1-C5 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl or neopentyl, preferably selected from C1-C5 straight-chain alkyl, more preferably methyl, ethyl or n-propyl.

[0033] In a preferred embodiment of the present invention, the compound represented by formula (I) is 2,3-diisopropyl-2-cyanosuccinic acid-1,4-bis-(2-methoxyethyl) ester, 2,3-diisopropyl-2-cyanosuccinic acid-1,4-bis-(2-ethoxyethyl) ester, 2,3-diisobutyl-2-cyanosuccinic acid-1,4-bis-(2-methoxyethyl) ester, 2,3-diisobutyl-2-cyanosuccinic acid-1,4-bis-(2-ethoxyethyl) ester, 2,3-di-sec-butyl-2-cyanosuccinic acid-1,4-bis-(2-methoxyethyl) ester or 2,3-di-sec-butyl-2-cyanosuccinic acid-1,4-bis-(2-ethoxyethyl) ester.

[0034] A second aspect of the present invention provides a method for preparing a compound, the method comprising the following steps:

[0035] In the presence of a catalyst, reacting the compound represented by formula (II) with the compound represented by formula (III) to obtain the compound represented by formula (I);

[0036]

[0037] Wherein, R1 and R2 are the same or different and are independently selected from C1-C 14 R3 is selected from C1-C 10 Alkylene, C3-C 10 Cycloalkylene or C7-C 20 Arylene; R4 is selected from C1-C 10 Alkyl, C3-C 10 Cycloalkyl or C7-C 20 Aryl; R5 and R6 are the same or different, each independently selected from C1-C 20 Alkyl, C3-C 20 Cycloalkyl and C6-C 20 One of the aromatic groups.

[0038] Among them, the types of R1 to R4 refer to the first aspect and will not be repeated here.

[0039] Preferably, R5 and R6 are the same or different and are independently selected from C1-C 10 Alkyl, C3-C 10 Cycloalkyl and C6-C 10 One of the aryl groups, more preferably a C1-C4 alkyl group, further preferably a methyl group, an ethyl group, an n-butyl group or a 2-methylpropyl group.

[0040] The compound represented by formula (II) can be, for example, dimethyl 2,3-diisopropyl-2-dicyanosuccinate, diethyl 2,3-diisopropyl-2-dicyanosuccinate, 1-methyl-4-ethyl 2,3-diisopropyl-2-cyanosuccinate; 1-ethyl-4-methyl 2,3-diisopropyl-2-cyanosuccinate; di-n-butyl 2,3-diisopropyl-2-cyanosuccinate; diisobutyl 2,3-diisopropyl-2-cyanosuccinate, etc.

[0041] The compound represented by formula (III) may be, for example, 2-methoxyethanol or 2-ethoxyethanol.

[0042] Preferably, the catalyst is an alkali metal salt or an alkali metal hydroxide. The alkali metal may be sodium or potassium. The catalyst may be sodium carbonate, potassium carbonate, sodium ethoxide, potassium ethoxide, sodium methoxide, potassium methoxide, potassium hydroxide, sodium hydroxide, etc.

[0043] Preferably, the catalyst is at least one of potassium carbonate, potassium hydroxide and sodium methoxide, more preferably potassium carbonate.

[0044] Preferably, the reaction conditions include: the reaction pressure is 0.01-0.15 MPa, more preferably 0.02-0.1 MPa; the reaction temperature is 40-160℃, more preferably 90-130℃; and the reaction time is 4-24h, more preferably 10-15h.

[0045] Preferably, the molar ratio of the compound of formula (II) to the compound of formula (III) is 1:0.5-20, such as 1:0.5, 1:1, 1:2, 1:4, 1:6, 1:8, 1:10, 1:12, 1:14, 1:16, 1:18, 1:20, and any range between any two of the values, more preferably 1:2-8.

[0046] Preferably, the molar ratio of the compound of formula (II) to the catalyst is 1:0.01-0.5, such as 1:0.01, 1:0.05, 1:0.1, 1:0.2, 1:0.3, 1:0.4, 1:0.5, and any range between any two of the values, preferably 1:0.08-0.3.

[0047] It should be understood that the reaction can be carried out under stirring or other mixing conditions.

[0048] Preferably, the method further comprises distillation during the reaction.

[0049] After the reaction is completed, the reaction product can be separated and purified. For example, after the reaction is completed, the reaction can be cooled, and the catalyst can be separated by filtration or centrifugation, and then the filtrate can be subjected to vacuum distillation (for example, the pressure is 10-50 Pa, and the temperature is 160-200℃, preferably 180-190℃) to remove unreacted raw materials and other by-products.

[0050] The purification method can be column chromatography, and the conditions of column chromatography can be selected by those skilled in the art as needed.

[0051] The preparation method of the compound of formula (II) can refer to CN104418770A, and the contents of CN104418770A can be incorporated herein in its entirety.

[0052] The third aspect of the present application provides a preparation method of a compound, which comprises the following steps:

[0053] (i) contacting the compound of formula (IV) with a metal alkoxide in a first aprotic solvent to obtain a reaction mixture,

[0054]

[0055] (ii) contacting the reaction mixture obtained in step (i) with a compound of formula (V) in a second aprotic solvent to obtain a compound of formula (II),

[0056]

[0057] (iii) reacting the compound of formula (II) with a compound of formula (III) in the presence of a catalyst to obtain a compound of formula (I);

[0058]

[0059] wherein R1and R2are the same or different, each independently selected from one of C1-C 14 alkyl; R3is selected from one of C1-C 10 alkylene, C3-C 10 cycloalkylene or C7-C 20 arylene; R4is selected from one of C1-C 10 alkyl, C3-C 10 cycloalkyl or C7-C 20 aryl; R5and R6are the same or different, each independently selected from one of C1-C 20 alkyl, C3-C 20 cycloalkyl and C6-C 20 aryl; and X is halogen.

[0060] wherein the nature of R1to R6is as described in the first and second aspect, which is not repeated here.

[0061] X is halogen, preferably Br or I.

[0062] Preferably, the metal alkoxide is selected from one or more of potassium methoxide, potassium ethoxide, potassium n-propoxide, potassium isopropoxide, potassium n-butoxide, potassium isobutoxide, potassium sec-butoxide, potassium tert-butoxide, sodium methoxide, sodium ethoxide, sodium n-propoxide, sodium isopropoxide, sodium n-butoxide, sodium isobutoxide, sodium sec-butoxide and sodium tert-butoxide, preferably from one or more of potassium methoxide, potassium ethoxide, potassium tert-butoxide, sodium methoxide, sodium ethoxide and sodium tert-butoxide; further preferably potassium methoxide, potassium ethoxide or potassium tert-butoxide.

[0063] Preferably, the molar ratio of the compound of formula (IV) to the metal alkoxide is 1 : 0.8-1.2, more preferably 1 : 1-1.2, most preferably 1 : 1-1.1.

[0064] Preferably, the first aprotic solvent contains one or more of oxygen, nitrogen and sulfur in its molecular formula, more preferably from one or more of tetrahydrofuran, dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and acetonitrile; further preferably N-methylpyrrolidone.

[0065] Preferably, the amount of the first aprotic solvent is 1-50 mL, more preferably 1.2-5 mL, and further preferably 1.5-5 mL, per gram of the compound represented by formula (IV).

[0066] Preferably, in step (i), the temperature of the contacting is -10°C to 120°C, more preferably 0-100°C, and further preferably 0-80°C.

[0067] Preferably, in step (i), the pressure of the contacting is under normal pressure.

[0068] Preferably, in step (ii), the second aprotic solvent contains one or more of oxygen, nitrogen and sulfur in its molecular formula, and is preferably one or more selected from the group consisting of tetrahydrofuran, dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and acetonitrile; and is further preferably N-methylpyrrolidone.

[0069] Preferably, the amount of the second aprotic solvent is 1-50 mL, more preferably 1.2-5 mL, and further preferably 1.5-5 mL, per gram of the compound represented by formula (IV).

[0070] Preferably, the molar ratio of the compound represented by formula (IV) to the compound represented by formula (V) is 1:0.8-1.2, and more preferably 1:0.9-1.1.

[0071] Preferably, in step (ii), the temperature of the contacting is 25°C to 150°C, and more preferably 65-120°C.

[0072] Preferably, in step (ii), the pressure of the contacting is 0.1 MPa to 2 MPa, and more preferably 1 MPa to 1.2 MPa.

[0073] In step (iii), the kind of the catalyst, the molar ratio of the compound represented by formula (II) to the catalyst, the molar ratio of the compound represented by formula (II) to the compound represented by formula (III), and the conditions of the reaction are as described in the second aspect, and will not be described here again.

[0074] In a preferred embodiment of the present application, the compound represented by formula (II) is diethyl 2,3-diisopropyl-2-cyanosuccinate, the compound represented by formula (III) is 2-methoxyethanol, and the compound represented by formula (I) produced is di(2-methoxyethyl) 2,3-diisopropyl-2-cyanosuccinate.

[0075] In a preferred embodiment of the present invention, the compound represented by formula (II) is diethyl 2,3-diisopropyl-2-cyanosuccinate, the compound represented by formula (III) is 2-ethoxyethanol, and the prepared compound represented by formula (I) is 1,4-bis(2-ethoxyethyl)-2,3-diisopropyl-2-cyanosuccinate.

[0076] The fourth aspect of the present invention provides a compound prepared according to the preparation method described above.

[0077] The compound has been described in detail in the first aspect and will not be repeated here.

[0078] A fifth aspect of the present invention provides use of the compound described above in olefin polymerization.

[0079] The compound can be used as an internal electron donor compound to prepare a catalyst for olefin polymerization (especially propylene polymerization).

[0080] The compound may be first prepared as a catalyst component, wherein the catalyst component comprises an internal electron donor compound, wherein the internal electron donor compound comprises the compound described above.

[0081] Preferably, the catalyst further comprises a magnesium-containing compound and a titanium-containing compound.

[0082] The magnesium-containing compound can be prepared by conventional methods in the art.

[0083] In a preferred embodiment of the present invention, the magnesium-containing compound is obtained by reacting a system comprising a magnesium halide, an alcohol compound and an ethylene oxide compound.

[0084] According to the present invention, the general formula of the magnesium halide can be MgYZ, wherein Y is chlorine or bromine, and Z is chlorine, bromine, C1-C 14 Alkyl, C6-C 14 Aryl, C1-C 14 Alkoxy, C6-C 14 Aryl or C6-C 14 of aryloxy.

[0085] Preferably, Z is chlorine, bromine, C1-C5 alkyl, C1-C5 alkoxy, C6-C 10 Aryl or C6-C 10 of aryloxy.

[0086] In the present invention, the C1-C5 alkoxy group includes but is not limited to methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentoxy, isopentoxy; the C6-C 10Aryl groups include, but are not limited to, phenyl, methylphenyl, ethylphenyl, dimethylphenyl, trimethylphenyl; C6-C 10 Aryloxy groups include, but are not limited to, phenoxy, methylphenoxy, ethylphenoxy, dimethylphenoxy, trimethylphenoxy.

[0087] Preferably, the magnesium halide is selected from at least one of magnesium chloride, magnesium bromide, phenoxymagnesium chloride, isopropoxymagnesium chloride and n-butoxymagnesium chloride; more preferably, the magnesium halide is magnesium dichloride.

[0088] In the present application, the alcohol compound comprises a first alcohol compound and an optional second alcohol compound, preferably, the first alcohol compound is a C1-C8 aliphatic alcohol, and the second alcohol compound is a C 16 -C 20 aliphatic alcohol or aromatic alcohol.

[0089] Preferably, the first alcohol compound is selected from at least one of ethanol, propanol, isopropanol, n-butanol, isobutanol, pentanol, isopentanol, n-hexanol, n-octanol and 2-ethylhexanol.

[0090] Preferably, the second alcohol compound is cetyl alcohol and / or stearyl alcohol.

[0091] According to the present application, the oxirane compound is shown as formula (VI):

[0092]

[0093] In formula (VI), R7and R8are the same or different, each independently selected from hydrogen, C1-C3 alkyl or halogenated alkyl.

[0094] Preferably, the oxirane compound is selected from at least one of oxirane, oxetane, butylene oxide, epichlorohydrin, epichlorobutane, epibromohydrin and epibromobutane.

[0095] Preferably, the weight ratio of titanium element in the titanium compound, magnesium element in the magnesium-containing carrier and the internal electron donor compound is 1:5-15:2-15; more preferably, 1:6-13:3-12.

[0096] Specifically, the preparation method can be implemented according to patent document CN103788247A, the content of which is incorporated herein by reference.

[0097] In a more preferred embodiment of the present application, the preparation method of the magnesium-containing compound comprises:

[0098] (1) mixing the magnesium halide, the first alcohol compound, the second alcohol compound, the optional dihydroxyalkyl compound and the optional inert liquid medium and heating to obtain a liquid mixture;

[0099] (2) emulsifying the liquid mixture obtained in step (1), and subjecting the emulsified product to a contact reaction with an oxirane compound to obtain a magnesium-containing compound.

[0100] Specific examples of the dihydrocarbyloxyhydrocarbon compound can include, but are not limited to, one or more of 2,2-dimethoxypropane, 2,2-dimethoxybutane, 2,2-dimethoxypentane, 3,3-dimethoxy pentane, 2,2-diethoxypropane, and 2,2-diphenoxypropane.

[0101] In step (1), the mixing of the respective substances is carried out at a temperature of not lower than 60°C so that the magnesium halide and the alcohol compound are allowed to react sufficiently. Preferably, the conditions for the mixing include a temperature of 60 to 120°C, more preferably 60 to 90°C, and a mixing time of 0.5 to 5 hours, more preferably 0.5 to 3 hours.

[0102] The amounts of the respective components can be appropriately selected depending on the intended composition, and the first alcohol compound is used in an amount of 4 to 30 mol, preferably 6 to 20 mol, per 1 mol of the magnesium halide, the oxirane compound is used in an amount of 1 to 10 mol, preferably 2 to 6 mol, the second alcohol compound is used in an amount of 0.001 to 1.5 mol, preferably 0.01 to 1 mol, and the dihydrocarbyloxyhydrocarbon compound is used in an amount of 0.001 to 1.5 mol, preferably 0.01 to 1 mol.

[0103] In step (2), the conditions for the contact reaction include a temperature of 80 to 120°C, preferably 80 to 100°C, and a time of 20 to 60 minutes, preferably 20 to 50 minutes.

[0104] The inert liquid medium involved in the present application can be various liquid media that are not chemically interacted with the reactants and the reaction products, such as silicone oil and / or hydrocarbon-based solvent, which are commonly used in the art. Specifically, the inert liquid medium can be one or two or more of kerosene, paraffin oil, vaseline oil, white oil, methyl silicone oil, ethyl silicone oil, methyl ethyl silicone oil, phenyl silicone oil, and methyl phenyl silicone oil.

[0105] The amount of the inert liquid medium can be selected depending on the specific amount of the magnesium halide. Generally, the amount of the inert liquid medium is 0.8 to 10 L, preferably 2 to 8 L, per 1 mol of magnesium element in the magnesium halide.

[0106] The magnesium-containing compound can also be prepared according to Patent Document CN1289542C, the entire contents of which are incorporated herein by reference.

[0107] In a preferred embodiment of the present application, the method for producing a magnesium-containing compound comprises:

[0108] 1) mixing the magnesium halide with a first alcohol compound and reacting at 110-130°C for 1-3 hours to obtain a magnesium halide / alcohol adduct melt;

[0109] 2) emulsifying the magnesium halide / alcohol adduct melt in the presence of an inert liquid medium and rapidly forming the emulsified product, and then drying to obtain the magnesium-containing compound.

[0110] The amount of the first alcohol compound is preferably 4-30 mol, more preferably 6-20 mol, per 1 mol of the magnesium halide.

[0111] The amount of the inert liquid medium is preferably 0.2-13 L, more preferably 0.6-6.5 L, per 1 mol of magnesium. The inert liquid medium can be added in step 1) and / or step 2), for example, only in step 2), i.e. the magnesium halide / alcohol adduct melt is mixed with the inert liquid medium, and the resulting mixture is emulsified to form an emulsion. The inert liquid medium can be added in both step 1) and step 2), i.e. the inert liquid medium is added as a reaction medium in step 1) to obtain a magnesium halide / alcohol adduct melt containing the inert liquid medium, and then the mixture is mixed with the inert liquid medium and emulsified to form an emulsion. The inert liquid medium in step 1) and step 2) can be the same or different, for example, the inert liquid medium in step 1) can be white oil, and the inert liquid medium in step 2) can be methyl silicone oil. In step 2), the inert liquid medium needs to be preheated to the same temperature as the magnesium halide / alcohol adduct melt containing the inert liquid medium. The inert liquid medium can also be added only in step 1) as a reaction medium to obtain a magnesium halide / alcohol adduct melt containing the inert liquid medium, which is emulsified to form an emulsion.

[0112] The emulsification can be carried out by various methods known to those skilled in the art, for example, the halogenated magnesium / alcoholic adduct melt can be subjected to high-speed shearing in the presence of an inert liquid medium to achieve emulsification. The method of high-speed shearing is known to those skilled in the art, for example, the emulsification can be carried out according to the high-speed stirring method disclosed in CN1151183C (i.e., the halogenated magnesium / alcoholic adduct melt is stirred in the inert liquid medium at a speed of 2000-5000 rpm), the method of dispersing the mixture of the halogenated magnesium / alcoholic adduct melt and the inert liquid medium in a high-gravity bed at a speed of 100-3000 rpm disclosed in CN1267508C, the method of emulsifying the mixture of the halogenated magnesium / alcoholic adduct melt, silicone oil and white oil in an emulsifying machine at a speed of 1500-8000 rpm disclosed in CN1463990A, and the method of emulsifying the mixture containing the halogenated magnesium / alcoholic adduct melt by spraying disclosed in US6020279.

[0113] The emulsified product can be quenched and shaped by methods known to those skilled in the art, for example, the emulsified product can be quenched and shaped by transferring the emulsified product into a liquid cooling medium.

[0114] The liquid cooling medium can be various liquid media commonly used in the art which do not chemically interact with the halogenated magnesium adduct. For example, the liquid cooling medium can be an inert hydrocarbon solvent. Specific examples of the liquid cooling medium can include, but are not limited to, n-pentane, n-hexane, n-heptane, gasoline and petroleum ether. Water in the liquid cooling medium can participate in the reaction or be removed by treatment to control the water content in the liquid cooling medium used to a range that does not affect the test results. Generally, the water content of the liquid cooling medium is controlled to be not higher than 5 ppm by weight. The method of controlling or reducing the water content in the liquid cooling medium is well known in the art, for example, the liquid material can be distilled and / or contacted with a water absorbent (e.g., molecular sieve), and a high-purity inert gas stream, such as a high-purity nitrogen stream, can be continuously introduced into the heated liquid material.

[0115] The temperature of the liquid cooling medium is appropriate to cool and shape the emulsified product. Generally, the temperature of the liquid cooling medium can be -50°C to 0°C, preferably -40°C to -20°C. The amount of the liquid cooling medium is not particularly limited as long as the amount of the liquid cooling medium is sufficient to cool and shape the emulsified product. Specifically, the volume ratio of the liquid cooling medium to the emulsified product is 1-15:1, preferably 2-9:1.

[0116] Preferably, the average particle diameter of the magnesium-containing compound is 1 to 100 μm, and the particle size distribution is less than 1.2. More preferably, the average particle diameter of the magnesium-containing compound is 10 to 70 μm, and the particle size distribution is less than or equal to 1.1.

[0117] In the case where the magnesium-containing compound is an alkoxy magnesium compound, the magnesium-containing compound can be prepared by mixing and reacting elemental magnesium such as magnesium metal powder with an alcohol compound and, optionally, an inert liquid medium to form an alkoxy magnesium compound, i.e., the magnesium-containing compound.

[0118] It should be understood that, regardless of the method of preparing the magnesium-containing compound, the method of preparing the magnesium-containing compound can further include a post-treatment, such as a solid-liquid separation, washing of the solid product, and drying. The solid-liquid separation can be any of various methods that can achieve separation of a solid phase from a liquid phase, such as suction filtration, pressure filtration, or centrifugal separation. Preferably, the method of solid-liquid separation is pressure filtration. The conditions of pressure filtration are not particularly limited in the present application, and can be determined so as to achieve separation of the solid phase from the liquid phase as fully as possible. The obtained magnesium-containing compound can be washed with an inert hydrocarbon solvent (e.g., n-pentane, n-hexane, n-heptane, petroleum ether, and gasoline) known to those skilled in the art. The conditions of drying are not particularly limited in the present application, and can be, for example, a drying temperature of 20 to 70°C, a drying time of 0.5 to 10 hours, and drying under normal pressure or reduced pressure.

[0119] In the present application, the titanium compound can be any of various titanium compounds conventionally used in the preparation of catalysts for the polymerization of olefins. The general formula of the titanium compound can be Ti(OR n ) 4-m X’ m wherein R n is a C1-C 14 aliphatic hydrocarbon group, X’ is F, Cl, or Br, and m is an integer of 1 to 4. Preferably, the titanium compound is at least one of titanium tetrachloride, titanium tetrabromide, titanium tetrafluoride, tributoxy titanium chloride, dibutoxy titanium dichloride, butoxy titanium chloride, triethoxy titanium chloride, diethoxy titanium dichloride, and ethoxy titanium chloride.

[0120] In the present application, the internal electron donor compound can further include an internal electron donor compound b, which is used in combination with the internal electron donor compound a. The internal electron donor compound b can be any of various internal electron donor compounds conventionally used in the preparation of catalysts for the polymerization of olefins.

[0121] Preferably, the internal electron donor compound b is at least one of carboxylic acid ester, alcohol ester, ether, ketone, nitrile, amine and silane, more preferably at least one of mono- or poly- aliphatic carboxylic acid ester, mono- or poly- aromatic carboxylic acid ester, diol ester and diether. In the present application, the specific compounds of mono- or poly- aliphatic carboxylic acid ester, mono- or poly- aromatic carboxylic acid ester, diol ester and diether can be selected according to the prior art, which will not be described in detail herein.

[0122] The catalyst component can be prepared using the conventional preparation method in the art, for example, the preparation method of the catalyst component can comprise: reacting the titanium-containing compound and the magnesium-containing compound in the presence of the internal electron donor compound to obtain the catalyst component.

[0123] In the present application, the conditions for the reaction of the magnesium-containing carrier with the titanium compound and the internal electron donor compound are not particularly limited, and preferably, the conditions for the reaction can comprise: the reaction temperature is 80-130°C, and the reaction time is 0.1-10 hours.

[0124] Preferably, the titanium-containing compound and the magnesium-containing compound are first contacted and mixed at low temperature (preferably -30°C to -15°C) (the time is preferably 20-40 min), and then slowly warmed to the above-mentioned reaction temperature. The internal electron donor can be added at one or more time periods before, during and after the reaction of the magnesium-containing compound with the titanium-containing compound.

[0125] The preparation method of the catalyst component can further comprise washing and drying the solid phase product. The solid-liquid separation can be various methods capable of realizing the separation of solid phase and liquid phase, for example, suction filtration, pressure filtration or centrifugal separation. In the present application, the obtained catalyst component can be sequentially washed with the titanium-containing compound and the inert hydrocarbon solvent known to those skilled in the art (for example: n-pentane, n-hexane, n-heptane, petroleum ether and gasoline). The conditions for drying in the present application are not particularly limited, for example: the drying temperature can be 20-70°C, the drying time can be 0.5-10 hours, and the drying can be carried out under normal pressure or reduced pressure.

[0126] Those skilled in the art can operate according to the conventional knowledge in the art after understanding the technical solutions of the present application, which will not be described in detail herein.

[0127] The other parameters not limited in the preparation method of the present application can be selected according to the prior art.

[0128] The present application further provides a catalyst comprising the catalyst component as described above.

[0129] Preferably, the catalyst further comprises an aluminum alkyl compound.

[0130] Preferably, the catalyst further comprises an external electron donor compound.

[0131] The catalyst is not particularly limited in terms of the kind and amount of the alkylaluminum compound and the external electron donor compound.

[0132] The alkylaluminum compound can have a general formula of AlR9R 10 R 11 In the general formula, R9, R 10 and R 11 may each be one of chlorine and a C1-C8 alkyl group, and at least one of R9, R 10 and R 11 is a C1-C8 alkyl group.

[0133] Preferably, the alkylaluminum compound is at least one of triethylaluminum, triisobutylaluminum, tri-n-butylaluminum, tri-n-hexylaluminum, tri-n-octylaluminum, chlorodiethylaluminum, chlorodiisobutylaluminum, chlorodi-n-butylaluminum, chlorodi-n-hexylaluminum, dichloroethylaluminum, dichloroisobutylaluminum, dichloro-n-butylaluminum, dichloro-n-hexylaluminum, and trichlorotriethylaluminum.

[0134] Preferably, the molar ratio of aluminum in the alkylaluminum compound to titanium in the catalyst component is 1-2000:1, and more preferably 20-500:1.

[0135] In the present application, the external electron donor compound can be various external electron donor compounds commonly used in the art, for example, the external electron donor compound can be one or two or more of a carboxylic acid, an anhydride, an ester, a ketone, an ether, an alcohol, an organophosphorus compound, and an organosilicon compound. Preferably, the external electron donor has a general formula of R 1’ a R 2’ b Si(OR 3’ ) c In the general formula, R 1’ , R 2’ and R 3’ are each a C1-C 18 hydrocarbon group or a C1-C 18 hydrocarbon group containing a heteroatom; a and b are each an integer of 0-2, c is an integer of 1-3, and a+b+c=4. More preferably, R 1’ , R 2’ , R 3’ are each independently a C1-C 18 substituted or unsubstituted hydrocarbon group; more preferably, a and b are each 1, c is 2, R 1’ , R 2’ are each independently a C3-C 10substituted or unsubstituted hydrocarbyl group, R 3’ substituted or unsubstituted hydrocarbyl group. 10 substituted or unsubstituted hydrocarbyl group.

[0136] In the present application, examples of the external electron donor compound can be, but are not limited to, cyclohexylmethyldimethoxysilane, diisopropyldimethoxysilane, di-n-butyldimethoxysilane, diisobutyldimethoxysilane, diphenyldimethoxysilane, methyl-tert-butyldimethoxysilane, dicyclopentyldimethoxysilane, 2-ethylpiperidinyl-2-tert-butyldimethoxysilane, (1,1,1-trifluoro-2-propyl)-2-ethylpiperidinyl dimethoxysilane, (1,1,1-trifluoro-2-propyl)-methyldimethoxysilane.

[0137] According to the present application, the molar ratio of the external electron donor compound to aluminum in the aluminum alkyl compound is 0.005-0.5:1, preferably 0.01-0.4:1.

[0138] The components in the catalyst can be simultaneously or sequentially added into the reactor during use, and there is no particular limitation, which can be selected as needed by those skilled in the art.

[0139] The seventh application of the present application provides the use of the compound as described above or the catalyst component as described above or the catalyst as described above in the polymerization of olefins.

[0140] The olefin polymerization method preferably comprises: contacting one or more olefins with the catalyst described above under olefin polymerization reaction conditions.

[0141] The olefin polymerization method of the present application is not particularly limited for the olefin polymerization conditions and the olefin used. The olefin can be at least one of ethylene, propylene, 1-butene, 2-butene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, 1-pentene, 2-pentene, 1-hexene and styrene. Preferably, it is at least one of ethylene, propylene, 1-butene, 2-butene and styrene, more preferably propylene.

[0142] The olefin polymerization method of the present application can be carried out according to conventional methods in the art. For example, the olefin polymerization can be bulk polymerization, gas phase polymerization or slurry polymerization. The olefin polymerization reaction conditions in the present application can be conventional conditions in the art, for example, the polymerization temperature can be 0-150℃, preferably 60-90℃; the polymerization pressure can be atmospheric pressure or pressurized. The medium used in liquid phase polymerization can be selected from inert solvents such as saturated aliphatic hydrocarbons or aromatic hydrocarbons such as isobutane, hexane, heptane, cyclohexane, naphtha, raffinate oil, hydrogenated gasoline, kerosene, benzene, toluene, xylene, etc., preferably toluene, n-hexane or cyclohexane.

[0143] In addition, hydrogen is used as a molecular weight regulator to adjust the molecular weight of the final polymer.

[0144] The olefin polymerization parameters not defined in the present application are all conventional techniques in the art.

[0145] The present application will be described in detail below by way of examples and application examples.

[0146] Unless otherwise specified, the various raw materials used are commercially available.

[0147] 1. The average particle diameter and particle size distribution of the magnesium-containing support were measured using a Masters Sizer 2000 particle size analyzer (manufactured by Malvern Instruments Ltd.).

[0148] 2. The apparent morphology of the magnesium-containing support was observed using an optical microscope (model Eclipse E200, commercially available from Nikon Corporation).

[0149] 3. The melt flow rate index of the polyolefin powder was measured according to ISO 1133 at 230°C under a load of 2.16 kg.

[0150] 4. The isotacticity of the polymer was determined using a heptane extraction method (heptane boiling extraction for 6 hours), i.e., 2 g of a dried polymer sample was placed in an extractor and extracted with boiling heptane for 6 hours. After that, the remaining material was dried to a constant weight, and the ratio of the weight of the resulting polymer (g) to 2 was the isotacticity.

[0151] Example 1

[0152] This example is used to illustrate a method for preparing 2,3-diisopropyl-2-cyanosuccinic acid 1,4-di-(2-methoxyethyl) ester.

[0153] In a 500 ml round bottom flask with condenser, liquid separator, stirrer, 100 g (0.353 mol) of 2,3-diisopropyl-2-cyanosuccinic acid diethyl ester, 107.3 g (1.412 mol) of 2-methoxyethanol, 4.87 g (0.0353 mol) of anhydrous potassium carbonate were added, the stirring was started, and the temperature of the reaction liquid was controlled at 105-110°C, the reaction was carried out at 0.1 MPa for 12 h, and the generated ethanol was distilled into the liquid separator and removed at the same time. After the reaction was completed, the reaction liquid was cooled, the anhydrous potassium carbonate was separated by filtration or centrifugation, and the unreacted 2,3-diisopropyl-2-cyanosuccinic acid diethyl ester, 2-methoxyethanol and other by-products were removed by distillation at 30 Pa and 182-190°C in the kettle under reduced pressure to obtain 84 g of the target compound 2,3-diisopropyl-2-cyanosuccinic acid-1,4-bis-(2-methoxyethyl) ester with a purity of 87%, and further separation and purification by column chromatography to obtain the product 2,3-diisopropyl-2-cyanosuccinic acid-1,4-bis-(2-methoxyethyl) ester with a purity of 98%.

[0154] Spectrum data of the product:

[0155] High-resolution electrospray mass spectrum (ESI): 366.0 with the molecular formula C 15 H 25 The ion peak mass number of the compound M+Na (theoretical value 366.17) is consistent.

[0156] IR: 2973, 2939, 2883, 2248, 1735, 1469, 1454, 1392, 1376, 1297, 1130

[0157] 1 H NMR (CDCI3 / TMS, 300 MHZ) (δ ppm): 1.01-1.05 (m, 6H, CH(CH3)2); 1.14-1.16 (d, 6H, CH(CH3)2); 2.14-2.24 (m, 1H, CH(CH3)2); 2.31-2.38 (m, 1H, CH(CH3)2); 3.05-3.07 (d, 1H, CHCH(CH3)2); 3.37-3.38 (2S, 6H, 2OCH3); 3.62-3.66 (m, 4H, 2CH2CH2OCH3); 4.28-4.42 (m, 4H, 2OCH2CH2OCH3)

[0158] Example 2 This example is used to illustrate the preparation method of 2,3-diisopropyl-2-cyanosuccinic acid-1,4-bis-(2-methoxyethyl) ester.

[0159] The feeding amount and test device in Example 1 were repeated, but the reaction was carried out under reduced pressure, the temperature of the reaction liquid was controlled at 94 to 101°C, and the reaction was carried out under reduced pressure at a pressure of 0.025 MPa, and the generated ethanol fraction was removed through a condenser and a liquid separator. The product 2,3-diisopropyl-2-cyanosuccinic acid-1,4-di-(2-methoxyethyl) ester was obtained by the same purification method using reduced pressure distillation and column chromatography, and the structure and spectrum of the product were identical to those of Example 1.

[0160] Examples 1 to 8 are used to illustrate the catalyst component for olefin polymerization, the preparation method thereof, the catalyst, and the olefin polymerization method according to the present application.

[0161] Example 1

[0162] (1) Preparation of the catalyst component for olefin polymerization

[0163] In a 0.6 L reaction kettle, 200 mL of white oil, 0.08 mol of magnesium chloride, 0.96 mol of ethanol, 0.015 mol of octadecanol, and 0.01 mol of 2,2-dimethoxypropane were added, and stirred and heated to 90°C. After 1 hour of reaction, 0.48 mol of epichlorohydrin was added, and after half an hour of reaction, pressure filtration was performed, and the product was washed with hexane 5 times. Vacuum drying was performed to obtain a magnesium-containing carrier Z1.

[0164] The average particle diameter (D50) of the magnesium-containing carrier Z1 was 50 microns, and the particle size distribution ((D90-D10) / D50) was 0.9. The particle morphology observed using an optical microscope was relatively regular, the surface was smooth, and the particles were basically spherical, the particle size distribution was relatively concentrated, and there were basically no irregular particles.

[0165] In a 300 mL glass reaction bottle, 100 mL of titanium tetrachloride was added and cooled to -20°C, 8 g of the magnesium-containing carrier Z1 was added, and stirred at -20°C for 30 min. Thereafter, slow heating to 110°C was started, 1.5 mmol of 2,3-diisopropyl-2-cyanosuccinic acid-1,4-di-(2-methoxyethyl) ester (prepared in Example 1) was added during the heating process, and after maintaining at 110°C for 30 min, the liquid was filtered off. Then, titanium tetrachloride was added for washing 2 times, and finally, hexane was added for washing 3 times, and after drying, an olefin polymerization catalyst component C1 was obtained.

[0166] (2) Propylene polymerization reaction

[0167] In a 5L autoclave, purged with nitrogen gas flow, then introduced 1mmol of triethylaluminum in hexane solution (the concentration of triethylaluminum is 0.5mmol / mL), 0.05mmol of methylcyclohexyldimethoxysilane, 10mL of anhydrous hexane and 10mg of catalyst component C1 for olefin polymerization, 1.5L (standard volume) of hydrogen gas and 2.5L of liquid propylene. The temperature was raised to 70°C, and reacted for 1 hour at this temperature, cooled, depressurized, and discharged to dry to obtain polypropylene powder, the specific properties of which are shown in Table 1.

[0168] Application Example 2

[0169] The amount of hydrogen added during the polymerization of propylene was changed to 6.5L (standard volume), and the other conditions were the same as in Application Example 1. The specific properties of the obtained polypropylene powder are shown in Table 1.

[0170] Application Example 3

[0171] In the preparation of the catalyst component, the internal electron donor compound was changed to the compound obtained in Example 2, and the other conditions were the same as in Application Example 1. The catalyst component C2 for olefin polymerization was obtained, and the specific properties of the obtained polypropylene powder are shown in Table 1.

[0172] Application Example 4

[0173] The amount of hydrogen added during the polymerization of propylene was changed to 6.5L (standard volume), and the other conditions were the same as in Application Example 3. The specific properties of the obtained polypropylene powder are shown in Table 1.

[0174] Application Example 5

[0175] (1) Preparation of catalyst component for olefin polymerization

[0176] The magnesium-containing carrier was prepared according to the method disclosed in Application Example 1 of CN1289542C, as follows:

[0177] In a 150 L reactor with stirring, 10 kg of anhydrous magnesium chloride and 12.6 kg of ethanol were added to 60 L of white oil with a viscosity of 30 centipoises (20°C) and reacted at 125°C for 2 hours. The resulting molten adduct was then transferred to a methyl silicone oil medium, which had been preheated to 125°C; the methyl silicone oil had a viscosity of 300 centipoises (20°C) and was used in an amount of 120 L; the mixture was stirred at a rate of 200 rpm for 10-30 minutes to obtain a mixture. The mixture was introduced into a high gravity rotating bed for dispersion, and the dispersed mixture was introduced into a hexane medium, which had been pre-cooled to -35°C, under stirring conditions; the hexane was used in an amount of 1200 L, and the molten magnesium chloride / ethanol adduct dispersed into small droplets was solidified by cooling to form spherical solid particles. The solid particles were filtered from the suspension obtained after the quenching, and the particles were washed with hexane at room temperature; the hexane was used in an amount of 100 L per time, and the washing was repeated 5 times; the magnesium-containing support Z2 was obtained by vacuuming at 30-50°C.

[0178] The average particle diameter (D50) of the magnesium-containing support Z2 was 52 microns, and the particle size distribution ((D90-D10) / D50) was 1.1. The morphology of the particles was observed using an optical microscope, and it was found that the particles of the magnesium-containing support Z2 were relatively regular in shape, the surface was relatively smooth, a small amount of irregular particles were present, and the particle size distribution was relatively concentrated.

[0179] In a 300 mL glass reaction bottle, 100 mL of titanium tetrachloride was cooled to -20°C, 8 grams of the magnesium-containing support Z2 was added, and stirring was performed at -20°C for 30 min. Then, the temperature was slowly increased to 110°C, 1 mmol of 2,3-diisopropyl-2-cyanobutane diacid-1,4-bis-(2-methoxyethyl) ester (prepared in Example 1) and 0.5 mmol of 2-isopropyl-2-isopentyl-1,3-dimethoxypropane were added during the temperature increase, and the liquid was filtered after the temperature was maintained at 110°C for 30 min. Then, the catalyst component C3 for olefin polymerization was obtained by washing with titanium tetrachloride 2 times and hexane 3 times, and drying.

[0180] (3) The catalyst component C3 obtained in step (2) was used to perform a propylene polymerization reaction according to the method described in Application Example 1, and a polypropylene powder was obtained; the specific properties are shown in Table 1.

[0181] Application Example 6

[0182] The amount of hydrogen added during the propylene polymerization reaction was changed to 6.5 L (standard volume), and the other conditions were the same as in Application Example 5. The specific properties of the obtained polypropylene powder are shown in Table 1.

[0183] Application Example 7

[0184] (1) In a 0.6L reactor, 0.08 mol of magnesium chloride, 1.7 mol of ethanol (first alcohol compound) were added, and the mixture was heated to 90°C under stirring, and then reacted for 1 hour to form a first product;

[0185] (2) The first product was subjected to a second contact with 0.48 mol of epichlorohydrin to form a second product, and the second contact was carried out at a temperature of 90°C for 30 minutes;

[0186] (3) The second product was filtered, and then subjected to a third contact with 2.5 mol of ethanol (second alcohol compound) and 0.35 mol of 1,3-dichloropropanol (halogenated alcohol) to form a fluid, and a third product was obtained;

[0187] (4) The third product was subjected to spray drying by using a spray machine B-290 having a nozzle head and a material conduit, and the third product was sprayed into a spray machine tower containing circulating nitrogen at 100°C, and the temperature of the third product in the material conduit was 15°C, and the temperature of the third product in the nozzle head was 120°C, and a spherical carrier Z3 was obtained.

[0188] The structure and composition of the obtained catalyst spherical carrier Z3 were tested as follows:

[0189]

[0190] The average particle diameter (D50) of the catalyst spherical carrier Z3 was 4 microns, and the particle size distribution ((D90-D10) / D50) was 0.9.

[0191] It was observed that the particle morphology of the catalyst spherical carrier Z3 was relatively regular, the surface was smooth, and the particles were basically spherical, the particle size distribution was relatively concentrated, and there were basically no abnormal particles.

[0192] In the process of preparing the catalyst spherical carrier Z3, no clogging occurred at the nozzle head of the spray machine, and a total of 11.8 g of the carrier Z3 was obtained. The preparation and application of the catalyst component were the same as in Application Example 5. The obtained catalyst component was C4, and the specific properties of the prepared polypropylene powder were as shown in Table 1.

[0193] Application Example 8

[0194] The amount of hydrogen added during the polymerization of propylene was changed to 6.5 L (standard volume), and the other conditions were the same as in Application Example 7. The specific properties of the obtained polypropylene powder were as shown in Table 1.

[0195] Application Comparative Example 1

[0196] The catalyst component was prepared by adding 1.5 mL of diisobutyl phthalate instead of the internal electron donor compound, and the obtained catalyst component was D-C1. The catalyst component D-C1 was added during the polymerization of propylene, and the other conditions were the same as those in Application Example 5. The specific properties of the obtained polypropylene powder are shown in Table 1.

[0197] Application Comparative Example 2

[0198] The hydrogen addition amount during the polymerization of propylene was changed to 6.5 L (standard volume), and the other conditions were the same as those in Application Comparative Example 1. The specific properties of the obtained polypropylene powder are shown in Table 1.

[0199] Table 1

[0200]

[0201] From the performance results of Application Examples 1-8 and Application Comparative Examples 1-2, it can be seen that the catalyst component containing the internal electron donor compound represented by formula (I) according to the present application has very good hydrogen sensitivity during the polymerization of olefins (especially propylene), and the molecular weight distribution is relatively wide, which has great industrial application prospects.

[0202] The preferred embodiments of the present application are described in detail above, but the present application is not limited thereto. Within the technical concept of the present application, various simple modifications can be made to the technical solutions of the present application, including the combination of various technical features in any other suitable manner, and these simple modifications and combinations should also be considered as disclosed by the present application and fall within the protection scope of the present application.

Claims

1. Use of a compound in olefin polymerization, characterized in that, The compound is 2,3-diisopropyl-2-cyanosuccinate-1,4-bis-(2-methoxyethyl) ester, 2,3-diisopropyl-2-cyanosuccinate-1,4-bis-(2-ethoxyethyl) ester, 2,3-diisobutyl-2-cyanosuccinate-1,4-bis-(2-methoxyethyl) ester, 2,3-diisobutyl-2-cyanosuccinate-1,4-bis-(2-ethoxyethyl) ester, 2,3-di-sec-butyl-2-cyanosuccinate-1,4-bis-(2-methoxyethyl) ester or 2,3-di-sec-butyl-2-cyanosuccinate-1,4-bis-(2-ethoxyethyl) ester; The olefin polymerization method comprises: contacting one or more olefins with a catalyst and hydrogen under olefin polymerization reaction conditions; The catalyst is composed of the compound, an external electron donor compound, a magnesium-containing compound, a titanium-containing compound and an alkyl aluminum compound; The external electron donor is selected from cyclohexylmethyldimethoxysilane, diisopropyldimethoxysilane, di-n-butyldimethoxysilane, diisobutyldimethoxysilane, diphenyldimethoxysilane, methyl-tert-butyldimethoxysilane, dicyclopentyldimethoxysilane, 2-ethylpiperidinyl-2-tert-butyldimethoxysilane, (1,1,1-trifluoro-2-propyl)-2-ethylpiperidinyldimethoxysilane or (1,1,1-trifluoro-2-propyl)-methyldimethoxysilane; The molar ratio of the titanium element in the titanium-containing compound, the magnesium element in the magnesium-containing compound, and the compound serving as the internal electron donor is 1:5-15:2-15; The molar ratio of aluminum in the alkyl aluminum compound to titanium in the titanium-containing compound is 1-2000:1; The molar ratio of the external electron donor compound to the aluminum in the alkyl aluminum compound is 0.005-0.5:1; The polymerization temperature is 0-150° C., and the pressure is normal pressure or pressurized pressure.

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