CN114478611A - Synthesis method of tetraethylene silane - Google Patents
Synthesis method of tetraethylene silane Download PDFInfo
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- CN114478611A CN114478611A CN202210138027.1A CN202210138027A CN114478611A CN 114478611 A CN114478611 A CN 114478611A CN 202210138027 A CN202210138027 A CN 202210138027A CN 114478611 A CN114478611 A CN 114478611A
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- reaction
- silane
- magnesium chloride
- chloride solution
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- 238000001308 synthesis method Methods 0.000 title abstract description 11
- ACNASVKDYHUAHH-UHFFFAOYSA-N ethene silane Chemical compound [SiH4].C=C.C=C.C=C.C=C ACNASVKDYHUAHH-UHFFFAOYSA-N 0.000 title description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910000077 silane Inorganic materials 0.000 claims abstract description 19
- 150000005672 tetraenes Chemical class 0.000 claims abstract description 18
- IJMWREDHKRHWQI-UHFFFAOYSA-M magnesium;ethene;chloride Chemical compound [Mg+2].[Cl-].[CH-]=C IJMWREDHKRHWQI-UHFFFAOYSA-M 0.000 claims description 24
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 21
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 14
- 229910052749 magnesium Inorganic materials 0.000 claims description 14
- 239000011777 magnesium Substances 0.000 claims description 14
- 238000003747 Grignard reaction Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 claims description 8
- 229910001641 magnesium iodide Inorganic materials 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- 238000010791 quenching Methods 0.000 claims description 8
- 230000000171 quenching effect Effects 0.000 claims description 8
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 7
- 238000005191 phase separation Methods 0.000 claims description 7
- 230000002194 synthesizing effect Effects 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 4
- UFHILTCGAOPTOV-UHFFFAOYSA-N tetrakis(ethenyl)silane Chemical compound C=C[Si](C=C)(C=C)C=C UFHILTCGAOPTOV-UHFFFAOYSA-N 0.000 claims 3
- 239000002000 Electrolyte additive Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000007789 gas Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 2
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/0827—Syntheses with formation of a Si-C bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention discloses a synthesis method of tetraene silane, which relates to the technical field of battery electrolyte additives. The synthesis method disclosed by the invention is simple to operate, few in reaction steps and easy to purify, the maximization of the product yield and the product purity in the production process is ensured by controlling the reaction conditions in each stage, and the product yield is further improved by reasonably controlling the consumption of reaction raw materials and the reaction process.
Description
Technical Field
The invention relates to the technical field of battery electrolyte additives, in particular to a method for synthesizing tetraene silane.
Background
The tetraethylene silane is used as an important silane additive in the lithium battery electrolyte, has an important effect on improving the stability of the lithium battery, can improve the consistency of voltage during shipment screening of the lithium battery, reduces self-discharge and the like.
The preparation of tetraene silane is mainly carried out by reacting vinyl magnesium chloride and silicon tetrachloride in a tetrahydrofuran solvent at present, but the reaction has the problems of incomplete substitution caused by difficult later-stage substitution reaction, difficult subsequent purification and the like.
Therefore, the current methods for preparing and purifying tetraene silane are not perfect enough, and the yield and purity are low.
Disclosure of Invention
The present invention is directed to a method for synthesizing tetraene silane, so as to solve the problems mentioned in the background art.
In order to achieve the purpose, the invention provides the following technical scheme:
a synthetic method of tetraene silane comprises the steps of taking tetrachlorosilane to dissolve in methyl tertiary butyl ether under the protection of inactive gas, adding a catalyst magnesium iodide, slowly dropwise adding a vinyl magnesium chloride solution into an obtained system, carrying out Grignard reaction, adding water for quenching after the reaction is finished, carrying out phase separation, and carrying out reduced pressure concentration on an obtained organic phase to obtain the tetraene silane, wherein the specific chemical reaction formula is as follows:
further, the weight volume ratio of tetrachlorosilane to methyl tert-butyl ether is 1 g: 7-8 mL.
Further, the molar ratio of tetrachlorosilane to vinyl magnesium chloride is 1: 4 to 4.2.
Further, when the vinyl magnesium chloride solution is dripped, the temperature of the system is 20-25 ℃; the temperature of the Grignard reaction is 20-25 ℃.
Further, the vinyl magnesium chloride solution is prepared by adding magnesium into tetrahydrofuran under the protection of inactive gas, introducing excessive chloroethylene, and heating for reaction.
Further, the weight ratio of magnesium to tetrahydrofuran is 1: 15 to 16.
Further, the heating reaction temperature is 60-70 ℃.
Compared with the prior art, the invention has the beneficial effects that:
according to the invention, methyl tert-butyl ether and tetrahydrofuran are used as solvents of the Grignard reaction together, so that the Grignard reaction can be promoted to be more complete; after the Grignard reaction is finished, adding water for quenching, dissolving the generated magnesium salt in water, directly layering with water because the methyl tert-butyl ether is not mutually soluble with the water, and directly concentrating the obtained organic phase to obtain the tetraene silane;
according to the invention, magnesium iodide is added as a catalyst, so that the Grignard reaction can be further promoted to be carried out, and the reaction is more complete;
the synthesis method disclosed by the invention is simple to operate, few in reaction steps and easy to purify, the maximization of the product yield and the product purity in the production process is ensured by controlling the reaction conditions in each stage, and the product yield is further improved by reasonably controlling the consumption of reaction raw materials and the reaction process.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without making any creative effort based on the embodiments in the present invention, belong to the protection scope of the present invention.
The first embodiment is as follows:
the synthesis method of the tetraethylene silane comprises the following steps:
1) preparation of vinyl magnesium chloride solution
Under the protection of nitrogen, 9.724g (0.4mol) of magnesium chips are added into 145.86mL of tetrahydrofuran, stirred and heated to 65 ℃, excess chloroethylene gas is introduced, and the mixture is stirred and reacted at 65 ℃ until the magnesium chips completely disappear, so that the vinyl magnesium chloride solution is obtained.
2) Preparation of tetraethylene silane
Dissolving 16.7g (0.1mol) of tetrachlorosilane in 130mL of methyl tert-butyl ether, adding 0.1g of catalyst magnesium iodide, controlling the temperature of the obtained system at 20 ℃, slowly dropwise adding all the vinyl magnesium chloride solution (the dropwise adding time is 2 hours) under the stirring state at 20 ℃, after the dropwise adding is finished, keeping the temperature at 20 ℃, continuously stirring for carrying out Grignard reaction for 2 hours, then slowly dropwise adding 75mL of water, carrying out quenching reaction, directly carrying out phase separation after the reaction is finished, drying the obtained organic phase by anhydrous magnesium sulfate, and concentrating under reduced pressure to obtain 9.28g of tetraene silane, wherein the yield is 68.10%, the purity is 99.6%, and the specific chemical reaction formula is as follows:
example two:
the synthesis method of the tetraethylene silane comprises the following steps:
1) preparation of vinyl magnesium chloride solution
Under the protection of nitrogen, 9.724g (0.4mol) of magnesium chips are added into 155.58mL of tetrahydrofuran, stirred and heated to 68 ℃, excess chloroethylene gas is introduced, and the mixture is stirred and reacted at 68 ℃ until the magnesium chips completely disappear, so that the vinyl magnesium chloride solution is obtained.
2) Preparation of tetraethylene silane
Dissolving 16.7g (0.1mol) of tetrachlorosilane in 133.6mL of methyl tert-butyl ether, adding 0.05g of magnesium iodide serving as a catalyst, controlling the temperature of the obtained system to be 24 ℃, slowly dropwise adding all the vinyl magnesium chloride solution (the dropwise adding time is 2.5 hours) at 24 ℃ under a stirring state, after the dropwise adding is finished, maintaining the temperature at 24 ℃, continuously stirring for carrying out a Grignard reaction for 3 hours, then slowly dropwise adding 80mL of water for carrying out a quenching reaction, directly carrying out phase separation after the reaction is finished, drying the obtained organic phase by anhydrous magnesium sulfate, and concentrating under reduced pressure to obtain 9.17g of tetraene silane, wherein the yield is 67.29%, and the purity is 99.5%.
Example three:
the synthesis method of the tetraethylene silane comprises the following steps:
1) preparation of vinyl magnesium chloride solution
Under the protection of nitrogen, 10.21g (0.42mol) of magnesium chips are added into 158.26mL of tetrahydrofuran, stirred and heated to 70 ℃, excess chloroethylene gas is introduced, and the mixture is stirred and reacted at 70 ℃ until the magnesium chips completely disappear, thus obtaining the vinyl magnesium chloride solution.
2) Preparation of tetraethylene silane
Dissolving 16.7g (0.1mol) of tetrachlorosilane in 116.9mL of methyl tert-butyl ether, adding 0.08g of magnesium iodide serving as a catalyst, controlling the temperature of the obtained system at 25 ℃, slowly dropwise adding all the vinyl magnesium chloride solution (the dropwise adding time is 2.3h) at 25 ℃ under a stirring state, after the dropwise adding is finished, maintaining the temperature at 25 ℃, continuously stirring for carrying out a Grignard reaction for 2.5h, then slowly dropwise adding 78mL of water, carrying out a quenching reaction, directly carrying out phase separation after the reaction is finished, drying the obtained organic phase by anhydrous magnesium sulfate, and concentrating under reduced pressure to obtain 9.11g of tetraene silane, wherein the yield is 66.85%, and the purity is 99.6%.
Example four:
the synthesis method of the tetraethylene silane comprises the following steps:
1) preparation of vinyl magnesium chloride solution
Under the protection of nitrogen, 9.724g (0.4mol) of magnesium chips are added into 150mL tetrahydrofuran, stirred and heated to 63 ℃, excess chloroethylene gas is introduced, and the mixture is stirred and reacted at 63 ℃ until the magnesium chips completely disappear, thus obtaining the vinyl magnesium chloride solution.
2) Preparation of tetraethylene silane
Dissolving 16.7g (0.1mol) of tetrachlorosilane in 125mL of methyl tert-butyl ether, adding 0.09g of catalyst magnesium iodide, controlling the temperature of the obtained system at 20 ℃, slowly dripping all the vinyl magnesium chloride solution (the dripping time is 2.1h) at 20 ℃ under the stirring state, after the dripping is finished, continuously stirring at 20 ℃ to carry out Grignard reaction for 2.5h, then slowly dripping 76mL of water to carry out quenching reaction, directly carrying out phase separation after the reaction is finished, drying the obtained organic phase by anhydrous magnesium sulfate, and concentrating under reduced pressure to obtain 9.24g of tetraene silane, wherein the yield is 67.81% and the purity is 99.4%.
Example five:
the synthesis method of the tetraethylene silane comprises the following steps:
1) preparation of vinyl magnesium chloride solution
Under the protection of nitrogen, 9.967g (0.41mol) of magnesium chips are added into 150mL tetrahydrofuran, stirred and heated to 60 ℃, excess chloroethylene gas is introduced, and the mixture is stirred and reacted at 60 ℃ until the magnesium chips completely disappear, thus obtaining the vinyl magnesium chloride solution.
2) Preparation of tetraethylene silane
Dissolving 16.7g (0.1mol) of tetrachlorosilane in 120mL of methyl tert-butyl ether, adding 0.07g of catalyst magnesium iodide, controlling the temperature of the obtained system at 23 ℃, slowly dropwise adding all the vinyl magnesium chloride solution (the dropwise adding time is 2 hours) under the stirring state at 23 ℃, after the dropwise adding is finished, keeping the 23 ℃, continuously stirring for carrying out Grignard reaction for 3 hours, then slowly dropwise adding 77mL of water, carrying out quenching reaction, directly carrying out phase separation after the reaction is finished, drying the obtained organic phase by anhydrous magnesium sulfate, and carrying out reduced pressure concentration to obtain 9.16g of tetraene silane, wherein the yield is 67.21%, and the purity is 99.5%.
Comparative example:
the finished product of tetraene silane is ordered on the market, and the product yield is 55.9 percent and the purity is 98.1 percent.
The yields and purities of the finished products of examples one to five were compared with those of the comparative example, and the comparison results are shown in table 1:
as can be seen from Table 1, the yield and purity of the tetraene silane produced by the synthesis method of the tetraene silane of the present invention are higher than those of the products sold on the market.
TABLE 1
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (7)
1. A method for synthesizing tetraene silane is characterized in that: under the protection of inactive gas, dissolving tetrachlorosilane in methyl tert-butyl ether, adding a catalyst magnesium iodide, slowly dropwise adding a vinyl magnesium chloride solution into the obtained system, carrying out Grignard reaction, adding water for quenching after the reaction is finished, carrying out phase separation, and carrying out reduced pressure concentration on the obtained organic phase to obtain the tetraene silane, wherein the specific chemical reaction formula is as follows:
2. the method of claim 1, wherein the method comprises: the weight volume ratio of tetrachlorosilane to methyl tert-butyl ether is 1 g: 7-8 mL.
3. The method of synthesizing tetraethenylsilane according to claim 1 or 2, wherein: the molar ratio of tetrachlorosilane to vinyl magnesium chloride is 1: 4 to 4.2.
4. The method of synthesizing tetraethenylsilane according to claim 1 or 2, wherein: when the vinyl magnesium chloride solution is dripped, the temperature of the system is 20-25 ℃; the temperature of the Grignard reaction is 20-25 ℃.
5. The method of synthesizing tetraethenylsilane according to claim 1 or 2, wherein: the vinyl magnesium chloride solution is prepared by adding magnesium into tetrahydrofuran under the protection of inactive gas, introducing excessive chloroethylene, and heating for reaction.
6. The method of claim 5, wherein: the weight ratio of magnesium to tetrahydrofuran is 1: 15 to 16.
7. The method of claim 5, wherein: the heating reaction temperature is 60-70 ℃.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020079219A (en) * | 2018-11-14 | 2020-05-28 | 信越化学工業株式会社 | Method for producing tetraalkenylsilane |
| CN111718366A (en) * | 2020-07-16 | 2020-09-29 | 苏州矽索新材料有限公司 | Preparation method of tetravinylsilane |
| CN113683634A (en) * | 2020-05-19 | 2021-11-23 | 张家港市国泰华荣化工新材料有限公司 | Synthetic method of tetravinylsilane |
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2022
- 2022-02-15 CN CN202210138027.1A patent/CN114478611B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020079219A (en) * | 2018-11-14 | 2020-05-28 | 信越化学工業株式会社 | Method for producing tetraalkenylsilane |
| CN113683634A (en) * | 2020-05-19 | 2021-11-23 | 张家港市国泰华荣化工新材料有限公司 | Synthetic method of tetravinylsilane |
| CN111718366A (en) * | 2020-07-16 | 2020-09-29 | 苏州矽索新材料有限公司 | Preparation method of tetravinylsilane |
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