A method for synthesizing long-chain diene-based dichlorosilane

Abstract

The application relates to a synthesis method of long-chain diene-based dichlorosilane and relates to the technical field of organic synthesis. The synthesis method comprises the following steps: preparing an alkylating agent by heating reaction of a halogenated alkene and magnesium metal in the presence of a catalyst and a solvent; in an inert gas atmosphere, dissolving silicon tetrachloride and dicyclopentadiene-based titanium dichloride in an organic solvent, adding the alkylating agent to react, and obtaining a product long-chain diene-based dichlorosilane after the reaction is completed. The product synthesized by the synthesis method of the application has a relatively uniform structure, tends to generate an end product, is not easy to cause a serious influence on rectification of a main product, and the end-chain alkene-based chlorosilane product is more conducive to preparation of a modified polyolefin resin, and the melt processing performance and mechanical properties of the polyolefin resin are improved.

Description

Technical Field

[0001] This invention relates to the field of organic synthesis technology, and specifically to a method for synthesizing long-chain dienyl dichlorosilane. Background Technology

[0002] Long-chain dienyl dichlorosilanes are increasingly widely used in the field of polyolefins and their resins due to their excellent crosslinking and coupling modification characteristics. They are mostly synthesized by Grignard method, hydrosilylation method or a combination of both.

[0003] Currently, publicly available Grignard methods for synthesizing alkenylchlorosilanes mostly involve the direct reaction of haloalkenyl Grignard reagents with chlorosilanes. While this method meets the requirements for yield, product separation, and production cost for short-chain alkenylsilanes, research has revealed that the decomposition, self-polymerization, and coupling of the Grignard reagent during the reaction significantly impact long-chain olefins, resulting in unsatisfactory synthesis and difficulties in product separation. Furthermore, high-purity long-chain haloalkenes, especially chloroalkenes, are difficult to obtain as raw materials, often containing numerous isomeric impurities, further complicating the separation of the target product after the reaction. Summary of the Invention

[0004] To address the aforementioned technical problems, the present invention aims to provide a method for synthesizing long-chain dienyl dichlorosilanes. The product synthesized using the method of the present invention has a more uniform structure, tends to generate end-group products, is less likely to severely affect the distillation of the main product, and the end-chain alkenyl chlorosilane products are more conducive to the preparation of modified polyolefin resins, improving the melt processing performance and mechanical properties of polyolefin resins.

[0005] The technical solution of the present invention to solve the above-mentioned technical problems is as follows: The purpose of this invention is to provide a method for synthesizing long-chain dienyl dichlorosilanes, comprising the following steps: In the presence of a catalyst and solvent, alkylating agents are prepared by heating alkylating agents with metallic magnesium. In an inert gas atmosphere, silicon tetrachloride and dicyclopentadienyl titanium dichloride are dissolved in an organic solvent, and the alkylating agent is added to react. The mixture is then filtered and distilled under reduced pressure to obtain long-chain dienyl dichlorosilane.

[0006] This invention first involves heating a haloalkene with metallic magnesium to produce an alkylating agent, such as a chloroalkene or brominated alkene reacting with metallic magnesium. The reaction formula is shown below, where R... 1 C8~C 10 Straight-chain alkenyl groups, including terminal monoolefins and mixtures containing partially non-terminal isomers, R 1 Preferably, the terminal octenyl group is used. Subsequently, the Grignard alkylating agent reduces tetravalent Ti(IV) to trivalent Ti(III) active titanium, accompanied by transmetallization to generate alkenyl titanium intermediates: Cp2Ti(III)R 1 A single electron transfer to the Si–Cl bond generates Si radical cations and Cp2Ti(IV)R. 1 Cl: R 1 The free radical combines with the Si free radical to ultimately generate the target product R. 1 2SiCl2, the catalyst can also be regenerated and recycled: Catalyst regeneration cycle: The entire reaction process is usually accompanied by partial alkenyl isomerization, which tends to generate end-group products.

[0007] The beneficial effects of the present invention are: the product synthesized by the synthesis method of the present invention has a more uniform structure, tends to generate end-group products, is less likely to have a serious impact on the distillation of the main product, and the end-chain alkenyl chlorosilane products are more conducive to the preparation of modified polyolefin resins, thereby improving the melt processing performance and mechanical properties of polyolefin resins.

[0008] Based on the above technical solution, the present invention can be further improved as follows.

[0009] Furthermore, the molar ratio of the catalyst to the magnesium metal is (0.0001~0.01):1.

[0010] Preferably, the molar ratio of the catalyst to the magnesium metal is (0.0003~0.008):1.

[0011] The beneficial effect of adopting the above-mentioned further scheme is that the catalytic initiation effect is obvious.

[0012] Furthermore, the molar ratio of the solvent to the haloolefin is (1.5~10):1.

[0013] Preferably, the molar ratio of the solvent to the haloolefin is (3~5):1.

[0014] The beneficial effect of adopting the above-mentioned further scheme is that the solvent system has good dispersibility and meets the reaction requirements.

[0015] Furthermore, the molar ratio of the haloolefin and the metallic magnesium is 1:1 to 1.2.

[0016] Furthermore, the catalyst is at least one selected from iodine, iodomethane, bromomethane, bromoethane, bromopropane, and bromobenzene; the solvent is at least one selected from tetrahydrofuran, methyltetrahydrofuran, and diethyl ether, and the molar ratio of the solvent to the magnesium metal is 2 to 6:1.

[0017] The beneficial effect of adopting the above-mentioned further scheme is that it can quickly and effectively start the reaction.

[0018] Furthermore, the organic solvent is at least one of tetrahydrofuran, methyltetrahydrofuran, and diethyl ether.

[0019] Further, the haloolefin is 8-chloro-1-octene, 8-chloro-(E)-2-octene, 8-chloro-(Z)-2-octene, 8-chloro-(E)-3-octene, 8-chloro-(Z)-3-octene, 8-bromo-1-octene, 8-bromo-(E)-2-octene, 8-bromo-(Z)-2-octene, 8-bromo-(E)-3-octene, 8-bromo-(Z)-3-octene, 9-chloro-1-nonene, (E / Z)-9- At least one of chloro-2-nonene, (E / Z)-9-chloro-3-nonene, 9-bromo-1-nonene, (E / Z)-9-bromo-2-nonene, (E / Z)-9-bromo-3-nonene, 10-chloro-1-decene, (E / Z)-10-chloro-2-decene, (E / Z)-10-chloro-3-decene, 10-bromo-1-decene, (E / Z)-10-bromo-2-decene, and (E / Z)-10-bromo-3-decene.

[0020] The beneficial effects of adopting the above-mentioned further solutions are: broadening the sources of raw materials and reducing preparation costs.

[0021] Furthermore, the molar ratio of silicon tetrachloride to dicyclopentadienyl titanium dichloride is 10~80:1.

[0022] Preferably, the molar ratio of silicon tetrachloride to dicyclopentadienyl titanium dichloride is 16~50:1.

[0023] The beneficial effect of adopting the above-mentioned further scheme is that, at this feed ratio, the reaction activity and selectivity are better.

[0024] Furthermore, the molar ratio of the dicyclopentadienyl titanium dichloride to the alkylating agent is 1:20~150, the reaction temperature is -60℃~40℃, and the reaction time is 1h~12h.

[0025] Preferably, the molar ratio of the dicyclopentadienyl titanium dichloride to the alkylating agent is 1:32~100, the reaction temperature is -40℃~20℃, and the reaction time is 1h~8h.

[0026] The advantages of adopting the above-mentioned further scheme are: higher reaction selectivity and product yield.

[0027] Furthermore, the long-chain dienyl dichlorosilane is one of the compounds bis(7-octenyl)dichlorosilane, bis(8-nonenyl)dichlorosilane, and bis(9-decenyl)dichlorosilane.

[0028] The advantages of adopting the above-mentioned further solutions are that the raw materials for specific alkenyl products are readily available, and the products have greater market application value. Detailed Implementation

[0029] The principles and features of the present invention are described below. The examples given are only for explaining the present invention and are not intended to limit the scope of the present invention.

[0030] Example 1: Synthesis of long-chain dienyl dichlorosilanes In an inert gas atmosphere, 2.25 mol of magnesium shavings, 0.17 mol of chlorooctene (containing ≥62% 8-chloro-1-octene, ≤13% 8-chloro-(Z)-2-octene, and 17~20% 8-chloro-(E)-3-octene as determined by NMR internal standard), 0.008 mol of iodine, and 1.0 mol of tetrahydrofuran were added to a reaction flask. After the reaction was initiated, a mixture of 1.85 mol of chlorooctene (containing ≥62% 8-chloro-1-octene, ≤13% 8-chloro-(Z)-2-octene, and 17~20% 8-chloro-(E)-3-octene as determined by NMR internal standard) and 2.4 mol of tetrahydrofuran was added dropwise. After the addition was complete, the mixture was refluxed at 65~70℃ for 1 hour, cooled to 20℃, and filtered to remove unreacted magnesium shavings, yielding octenyl magnesium chloride alkylating agent. In a low-temperature circulating cold liquid inert gas atmosphere reaction flask, 1.0 mol of silicon tetrachloride, 0.018 mol of dicyclopentadienyl titanium dichloride, and 3.1 mol of tetrahydrofuran were mixed evenly. The previously synthesized octenyl magnesium chloride alkylating agent was slowly added at -35°C. After the addition was completed in 2 hours, the mixture was stirred for 4 hours. After the reaction was completed, the mixture was filtered and distilled under reduced pressure. The fraction collected at 158°C~161°C (10 mmHg) was used to obtain 0.719 mol of a fraction containing di(7-octenyl)dichlorosilane with a purity ≥98% and a yield of 71.2% (synthesis yield = 2 × (moles of product di(7-octenyl)dichlorosilane / moles of halogenated octene)%).

[0031] NMR data of the target product: 1 H-NMR (400MHz, CDCl3, ppm): δ: 1.00~1.04(t, 4H, Si-CH2), 1.29~ 1.30(m, 12H, CH2), 2.16~2.20(m, 4H, CH2), 5.02~5.07(q, 4H, =CH2),5.80~5.83(m, 2H, CH=).

[0032] Example 2: Synthesis of long-chain dienyl dichlorosilanes In an inert gas atmosphere, 1.86 mol of magnesium shavings, 0.16 mol of 8-bromo-1-octene (containing ≥97% 8-bromo-1-octene and ≤1% 8-bromo-(E)-3-octene as determined by NMR internal standard), 0.007 mol of iodine, and 0.8 mol of tetrahydrofuran were added to a reaction flask. After the reaction was initiated, a mixture of 1.52 mol of 8-bromo-1-octene (containing ≥97% 8-bromo-1-octene and ≤1% 8-bromo-(E)-3-octene as determined by NMR internal standard) and 1.91 mol of tetrahydrofuran was added dropwise. After the addition was complete, the mixture was refluxed at 65-70°C for 1.5 hours, cooled to 20°C, and filtered to remove unreacted magnesium shavings, yielding octenyl magnesium bromide alkylating agent.

[0033] In a low-temperature circulating cold liquid inert gas atmosphere reaction flask, 0.82 mol of silicon tetrachloride, 0.015 mol of dicyclopentadienyl titanium dichloride, and 2.6 mol of tetrahydrofuran were mixed evenly. The previously prepared octenyl magnesium bromide alkylating agent was slowly added at -20℃. After the addition was completed in 1.5 hours, the mixture was stirred for 4 hours. After the reaction was completed, the mixture was filtered and distilled under reduced pressure. The fraction collected at 158℃~161℃ (10 mmHg) was used to obtain 0.507 mol of a fraction containing di(7-octenyl)dichlorosilane with a purity ≥98% and a yield of 60.4% (synthesis yield = 2 × (moles of product di(7-octenyl)dichlorosilane / moles of octene bromide)%).

[0034] NMR data of the target product: 1 H-NMR (400MHz, CDCl3, ppm): δ: 1.00~1.04(t, 4H, Si-CH2), 1.29~ 1.30(m, 12H, CH2), 2.16~2.20(m, 4H, CH2), 5.02~5.07(q, 4H, =CH2),5.80~5.83(m, 2H, CH=).

[0035] Example 3: Synthesis of Long-Chain Dienyl Dichlorosilanes In an inert gas atmosphere, 1.14 mol of magnesium shavings, 0.18 mol of decene chloride (containing ≥55% 10-chloro-1-decene, ≤5% 10-chloro-(Z)-2-decene, and 30-35% 10-chloro-(E)-3-decene as determined by NMR internal standard), 0.009 mol of iodine, and 0.52 mol of tetrahydrofuran were added to a reaction flask. After the reaction was initiated, a mixture of 0.86 mol of decene chloride (containing ≥55% 10-chloro-1-decene, ≤5% 10-chloro-(Z)-2-decene, and 30-35% 10-chloro-(E)-3-decene as determined by NMR internal standard) and 1.1 mol of tetrahydrofuran was added dropwise. After the addition was complete, the mixture was refluxed at 65-70°C for 2 hours, cooled to 20°C, and filtered to remove unreacted magnesium shavings, yielding decenyl magnesium chloride alkylating agent.

[0036] In a low-temperature circulating cold liquid inert gas atmosphere reaction flask, 0.5 mol of silicon tetrachloride, 0.009 mol of dicyclopentadienyl titanium dichloride, and 1.6 mol of tetrahydrofuran were mixed evenly. The previously prepared decenyl magnesium chloride alkylating agent was slowly added at -40℃. After the addition was completed in 3 hours, the mixture was stirred for 5 hours. After the reaction was completed, the mixture was filtered and distilled under reduced pressure. The fraction collected at 201℃~203℃ (12 mmHg) was used to obtain 0.358 mol of a fraction containing di(9-decenyl)dichlorosilane with a purity ≥98% and a yield of 68.8% (synthesis yield = 2 × (moles of product di(9-decenyl)dichlorosilane / moles of halooctene)%).

[0037] NMR data of the target product: 1 H-NMR (400MHz, CDCl3, ppm): δ: 1.00~1.04(t, 4H, Si-CH2), 1.29~ 1.30(m, 16H, CH2), 2.16~2.20(m, 4H, CH2), 5.02~5.07(q, 4H, =CH2),5.80~5.83(m, 2H, CH=).

[0038] Example 4: Synthesis of Long-Chain Dienyl Dichlorosilanes In an inert gas atmosphere, 1.17 mol of magnesium shavings, 0.15 mol of 8-bromo-1-octene (containing ≥98% 8-bromo-1-octene and ≤1% 8-bromo-(E)-3-octene as determined by NMR internal standard), 0.007 mol of iodine, and 0.5 mol of tetrahydrofuran were added to a reaction flask. After the reaction was initiated, a mixture of 0.9 mol of 8-bromo-1-octene (containing ≥98% 8-bromo-1-octene and ≤1% 8-bromo-(E)-3-octene as determined by NMR internal standard) and 1.2 mol of tetrahydrofuran was added dropwise. After the addition was complete, the mixture was refluxed at 65℃~70℃ for 2 hours, cooled to 20℃, and filtered to remove unreacted magnesium shavings, yielding octenyl magnesium bromide alkylating agent. In a low-temperature circulating cold liquid inert gas atmosphere reaction flask, 0.51 mol of silicon tetrachloride, 0.013 mol of dicyclopentadienyl titanium dichloride, and 1.64 mol of tetrahydrofuran were mixed evenly. The octenyl magnesium bromide alkylating agent prepared above was slowly added at -40℃. After the addition was completed in 4 hours, the mixture was stirred for 8 hours. After the reaction was completed, the mixture was filtered and distilled under reduced pressure. The fraction collected at 158℃~161℃ (10 mmHg) was used to obtain 0.358 mol of a fraction containing di(7-octenyl)dichlorosilane with a purity ≥98% and a yield of 68.1% (synthesis yield = 2 × (moles of product di(7-octenyl)dichlorosilane / moles of octene bromide)%).

[0039] NMR data of the target product: 1 H-NMR (400MHz, CDCl3, ppm): δ: 1.00~1.04(t, 4H, Si-CH2), 1.29~ 1.30(m, 12H, CH2), 2.16~2.20(m, 4H, CH2), 5.02~5.07(q, 4H, =CH2),5.80~5.83(m, 2H, CH=).

[0040] Example 5: Synthesis of Long-Chain Dienyl Dichlorosilane In an inert gas atmosphere, 2.28 mol of magnesium shavings, 0.2 mol of nonene chloro (containing ≥59% 9-chloro-1-nonene, ≤10% 9-chloro-(Z)-2-nonene, and 20-25% 9-chloro-(E)-3-nonene as determined by NMR internal standard), 0.009 mol of iodine, and 0.52 mol of tetrahydrofuran were added to a reaction flask. After the reaction was initiated, a mixture of 1.72 mol of decene chloro (containing ≥59% 9-chloro-1-nonene, ≤10% 9-chloro-(Z)-2-nonene, and 20-25% 9-chloro-(E)-3-nonene as determined by NMR internal standard) and 2 mol of tetrahydrofuran was added dropwise. After the addition was complete, the mixture was refluxed at 65-70°C for 1.1 hours, cooled to 20°C, and filtered to remove unreacted magnesium shavings, yielding a nonenyl magnesium chloride alkylating agent. In a low-temperature circulating cold liquid inert gas atmosphere reaction flask, 1.08 mol of silicon tetrachloride, 0.016 mol of dicyclopentadienyl titanium dichloride, and 3 mol of tetrahydrofuran were mixed evenly. The nonenyl magnesium chloride alkylating agent prepared above was slowly added at -10℃. After the addition was completed in 1.5 hours, the mixture was stirred for 4 hours. After the reaction was completed, the mixture was filtered and distilled under reduced pressure. The fraction collected at 179℃~181℃ (10 mmHg) was used to obtain 0.648 mol of a fraction containing di(8-nonenyl)dichlorosilane with a purity ≥98% and a yield of 67.5% (synthesis yield = 2 × (moles of product di(8-nonenyl)dichlorosilane / moles of halooctene)%).

[0041] NMR data of the target product: 1H-NMR (400MHz, CDCl3, ppm): δ: 1.00~1.04(t, 4H, Si-CH2), 1.29~ 1.30(m, 14H, CH2), 2.16~2.20(m, 4H, CH2), 5.02~5.07(q, 4H, =CH2),5.80~5.83(m, 2H, CH=).

[0042] Comparative Example 1: In an inert gas atmosphere, 0.75 mol of magnesium shavings, 0.12 mol of 8-bromo-1-octene (containing ≥98% 8-bromo-1-octene and ≤1% 8-bromo-(E)-3-octene as determined by NMR internal standard), 0.005 mol of iodine, and 0.4 mol of tetrahydrofuran were added to a reaction flask. After the reaction was initiated, a mixture of 0.6 mol of 8-bromo-1-octene (containing ≥98% 8-bromo-1-octene and ≤1% 8-bromo-(E)-3-octene as determined by NMR internal standard) and 1.3 mol of tetrahydrofuran was added dropwise. After the addition was complete, the mixture was refluxed at 65℃~70℃ for 1 hour, cooled to 20℃, and filtered to remove unreacted magnesium shavings, yielding octenyl magnesium chloride alkylating agent. In a reaction flask under a low-temperature circulating cold liquid inert gas atmosphere, 0.34 mol of silicon tetrachloride and 1.8 mol of tetrahydrofuran were mixed evenly. The octenyl magnesium chloride alkylating agent prepared above was added at -35°C. After the addition was completed in 1.5 hours, the mixture was stirred for 5 hours. The solid residue was small after filtration, and the mixture was distilled under reduced pressure. No stable fraction at 150~165°C (10 mmHg) was collected.

[0043] Comparative Example 2: In an inert gas atmosphere, 2.25 mol of magnesium shavings, 0.17 mol of chlorooctene (containing ≥67% 8-chloro-1-octene, ≤9% 8-chloro-(Z)-2-octene, and 18~21% 8-chloro-(E)-3-octene as determined by NMR internal standard), 0.008 mol of iodine, and 1.0 mol of tetrahydrofuran were added to a reaction flask. After the reaction was initiated, a mixture of 1.93 mol of chlorooctene (containing ≥67% 8-chloro-1-octene, ≤9% 8-chloro-(Z)-2-octene, and 18~21% 8-chloro-(E)-3-octene as determined by NMR internal standard) and 2.2 mol of tetrahydrofuran was added dropwise. After the addition was complete, the mixture was refluxed at 65~70℃ for 1 hour, cooled to 20℃, and filtered to remove unreacted magnesium shavings, yielding octenyl magnesium chloride alkylating agent. In an inert gas atmosphere reaction flask, 1.0 mol of silicon tetrachloride and 3 mol of tetrahydrofuran were mixed evenly, and the octenyl magnesium chloride alkylating agent prepared above was added at 65℃~72℃. During the reaction, the addition rate was adjusted but no significant temperature increase was observed. After the addition was completed in 2 hours, the mixture was stirred for 6 hours. After the reaction was completed, the solid residue was filtered out and the product was distilled under reduced pressure. The fraction collected at 118℃~121℃ (10 mmHg) was suspected to be a monosubstituted product.

[0044] The NMR data for the monosubstituted products are as follows: 1 H-NMR (400MHz, CDCl3, ppm): δ: 1.00~1.04(t, 2H, Si-CH2), 1.29~ 1.30(m, 8H, CH2), 2.16~2.20(m, 2H, CH2), 5.02~5.07(q, 2H, =CH2).

[0045] The fraction collected at 158℃~161℃ (10mmHg) yielded 0.152 mol of a fraction containing di(7-octenyl)dichlorosilane, with a purity ≥95% and a yield of 14.5% (synthesis yield = 2 × (moles of di(7-octenyl)dichlorosilane / moles of halogenated octene)%). NMR data: 1 H-NMR (400MHz, CDCl3, ppm): δ: 1.00~1.04(t, 4H, Si-CH2), 1.29~1.30(m, 12H, CH2), 2.16~2.20(m, 4H, CH2), 5.02~5.07(q, 4H, =CH2), 5.80~5.83(m, 2H, CH=).

[0046] Comparative Example 3: In an inert gas atmosphere, 1.15 mol of magnesium shavings, 0.17 mol of decene chloride (containing ≥73% 10-chloro-1-decene, ≤5% 10-chloro-(Z)-2-decene, and 10-17% 10-chloro-(E)-3-decene as determined by NMR internal standard), 0.004 mol of iodine, and 0.55 mol of tetrahydrofuran were added to a reaction flask. After the reaction was initiated, a mixture of 0.88 mol of decene chloride (containing ≥73% 10-chloro-1-decene, ≤5% 10-chloro-(Z)-2-decene, and 10-17% 10-chloro-(E)-3-decene as determined by NMR internal standard) and 1.05 mol of tetrahydrofuran was added dropwise. After the addition was complete, the mixture was refluxed at 65-70°C for 2 hours, cooled to 20°C, and filtered to remove unreacted magnesium shavings, yielding decenyl magnesium chloride alkylating agent. In an inert gas atmosphere reaction flask, 0.52 mol of silicon tetrachloride and 1.7 mol of tetrahydrofuran were mixed evenly. The previously prepared decenyl magnesium chloride alkylating agent was added dropwise at 66℃~68℃. After the addition was completed in 1 hour, the mixture was stirred for 3.5 hours. After the reaction was completed, the mixture was filtered and distilled under reduced pressure. The fraction collected at 201℃~203℃ (10 mmHg) was used to obtain 0.178 mol of a fraction containing di(9-decenyl)dichlorosilane with a purity ≥96% and a yield of 33.9% (synthesis yield = 2 × (moles of product di(9-decenyl)dichlorosilane / moles of halooctene)%).

[0047] NMR data of the target product: 1 H-NMR (400MHz, CDCl3, ppm): δ: 1.00~1.04(t, 4H, Si-CH2), 1.29~ 1.30(m, 16H, CH2), 2.16~2.20(m, 4H, CH2), 5.02~5.07(q, 4H, =CH2),5.80~5.83(m, 2H, CH=).

[0048] Although embodiments of the present invention have been shown and described above, it is understood that the above embodiments are exemplary and should not be construed as limiting the present invention. Those skilled in the art can make changes, modifications, substitutions and variations to the above embodiments within the scope of the present invention.

Claims

1. A method for synthesizing long-chain dienyl dichlorosilane, characterized in that, Includes the following steps: In the presence of a catalyst and solvent, alkylating agents are prepared by heating alkylating agents with metallic magnesium. In an inert gas atmosphere, silicon tetrachloride and dicyclopentadienyl titanium dichloride are dissolved in an organic solvent, and the alkylating agent is added to react. After the reaction is completed, the product long-chain dienyl dichlorosilane is obtained.

2. The method for synthesizing a long-chain dienyl dichlorosilane according to claim 1, characterized in that, The molar ratio of the catalyst to the magnesium metal is (0.0001~0.01):

1.

3. The method for synthesizing a long-chain dienyl dichlorosilane according to claim 1, characterized in that, The molar ratio of the solvent to the haloolefin is (1.5~10):

1.

4. The method for synthesizing a long-chain dienyl dichlorosilane according to claim 1, characterized in that, The molar ratio of the haloolefin and the magnesium metal is 1:1 to 1.

2.

5. The method for synthesizing a long-chain dienyl dichlorosilane according to claim 1, characterized in that, The catalyst is at least one selected from iodine, iodomethane, bromomethane, bromoethane, bromopropane, and bromobenzene; the solvent is at least one selected from tetrahydrofuran, methyltetrahydrofuran, and diethyl ether, and the molar ratio of the solvent to the magnesium metal is 2~6:

1.

6. The method for synthesizing a long-chain dienyl dichlorosilane according to claim 1, characterized in that, The organic solvent is at least one of tetrahydrofuran, methyltetrahydrofuran, and diethyl ether.

7. The method for synthesizing a long-chain dienyl dichlorosilane according to claim 1, characterized in that, The haloalkene is 8-chloro-1-octene, 8-chloro-(E)-2-octene, 8-chloro-(Z)-2-octene, 8-chloro-(E)-3-octene, 8-chloro-(Z)-3-octene, 8-bromo-1-octene, 8-bromo-(E)-2-octene, 8-bromo-(Z)-2-octene, 8-bromo-(E)-3-octene, 8-bromo-(Z)-3-octene, 9-chloro-1-nonene, (E / Z)-9-chloro- At least one of 2-nonene, (E / Z)-9-chloro-3-nonene, 9-bromo-1-nonene, (E / Z)-9-bromo-2-nonene, (E / Z)-9-bromo-3-nonene, 10-chloro-1-decene, (E / Z)-10-chloro-2-decene, (E / Z)-10-chloro-3-decene, 10-bromo-1-decene, (E / Z)-10-bromo-2-decene, and (E / Z)-10-bromo-3-decene.

8. The method for synthesizing a long-chain dienyl dichlorosilane according to claim 1, characterized in that, The molar ratio of silicon tetrachloride to dicyclopentadienyl titanium dichloride is 10~80:

1.

9. The method for synthesizing a long-chain dienyl dichlorosilane according to claim 1, characterized in that, The molar ratio of the dicyclopentadienyl titanium dichloride to the alkylating agent is 1:20~150, the reaction temperature is -60℃~40℃, and the reaction time is 1h~12h.

10. A method for synthesizing a long-chain dienyl dichlorosilane according to any one of claims 1 to 9, characterized in that, The long-chain dienyl dichlorosilane is one of the compounds bis(7-octenyl)dichlorosilane, bis(8-nonenyl)dichlorosilane, and bis(9-decenyl)dichlorosilane.

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