CN110964050A - Preparation method of methylvinyldi (N-ethylacetamido) silane - Google Patents
Preparation method of methylvinyldi (N-ethylacetamido) silane Download PDFInfo
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- CN110964050A CN110964050A CN201911319650.1A CN201911319650A CN110964050A CN 110964050 A CN110964050 A CN 110964050A CN 201911319650 A CN201911319650 A CN 201911319650A CN 110964050 A CN110964050 A CN 110964050A
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- silane
- methyl vinyl
- methylvinyldi
- ethylacetamido
- dropwise adding
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- IMPVGWPSUORTEQ-UHFFFAOYSA-N N-[[acetyl(ethyl)amino]-prop-1-enylsilyl]-N-ethylacetamide Chemical compound CC=C[SiH](N(C(C)=O)CC)N(C(C)=O)CC IMPVGWPSUORTEQ-UHFFFAOYSA-N 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title abstract description 5
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 claims abstract description 46
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 claims abstract description 42
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 34
- 238000001816 cooling Methods 0.000 claims abstract description 18
- 238000001914 filtration Methods 0.000 claims abstract description 18
- 238000003756 stirring Methods 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 11
- 239000011230 binding agent Substances 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 6
- VMNLXFJTVKFDIM-UHFFFAOYSA-N n-[[acetyl(ethyl)amino]-ethenyl-methylsilyl]-n-ethylacetamide Chemical compound CCN(C(C)=O)[Si](C)(C=C)N(CC)C(C)=O VMNLXFJTVKFDIM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- 239000000706 filtrate Substances 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 66
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 54
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 36
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 22
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 238000009776 industrial production Methods 0.000 abstract description 3
- 230000002349 favourable effect Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 description 30
- 239000000047 product Substances 0.000 description 16
- 239000012043 crude product Substances 0.000 description 15
- 238000005485 electric heating Methods 0.000 description 15
- 238000010907 mechanical stirring Methods 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000003566 sealing material Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000006240 deamidation Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 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
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention discloses a preparation method of methyl vinyl di (N-ethyl acetamido) silane, which comprises the steps of adding pyrrole as a catalyst, N-ethyl acetamide with the molar ratio of 2:1:2.05-2.15, methyl vinyl dichlorosilane and an acid-binding agent into an organic solvent to obtain a solution A; and slowly adding methyl vinyl dichlorosilane into the solution A under the stirring condition at 70-80 ℃, preserving the temperature of the reaction liquid at 85-95 ℃ for 2-4h after the addition of the methyl vinyl dichlorosilane is finished, cooling the reaction liquid to room temperature, filtering, and rectifying the filtrate to obtain the methyl vinyl di (N-ethyl acetamido) silane. The method has the advantages of mild reaction conditions, simple operation and higher yield, and is favorable for industrial production.
Description
Technical Field
The invention belongs to the field of organic silicon, and particularly relates to a preparation method of methylvinyl di (N-ethyl acetamido) silane.
Background
Methyl vinyl di (N-ethyl acetamido) silane is used as a chain extender, the molecular chain of the organic silicon sealing material is linearly lengthened while the organic silicon sealing material is crosslinked, crosslinking points are reduced, the network topological structure is changed, the regulation and control of modulus and other mechanical properties can be realized by changing the density and distribution of the crosslinking points, and the prepared deamidation sealing material has lower modulus and higher elongation at break. However, few methods for synthesizing methylvinyldi (N-ethylacetoamino) silane are reported, and in the prior art method for producing methylvinyldi (N-ethylacetoamino) silane from N-ethylacetamide and methylvinyldichlorosilane, the hydrogen chloride generated by the reaction may cause side reactions, resulting in low product yield.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides the preparation method of the methylvinyl di (N-ethyl acetamido) silane, which effectively reduces the occurrence of side reactions by utilizing the mixed acid-binding agent and the mixed solvent, and has the advantages of mild reaction conditions, less side reactions, easy process operation, higher yield and contribution to industrial production.
The structural formula of the methylvinyldi (N-ethylacetamido) silane prepared by the invention is shown as follows:
the technical scheme provided by the invention is as follows:
a method for preparing methylvinyldi (N-ethylacetamido) silane, comprising the steps of: adding pyrrole catalyst, N-ethyl acetamide with the molar ratio of 2:1:2.05-2.15, methyl vinyl dichlorosilane and an acid-binding agent into an organic solvent to obtain a solution A; and slowly adding methyl vinyl dichlorosilane into the solution A under the stirring condition at 70-80 ℃, preserving the temperature of the reaction liquid at 85-95 ℃ for 2-4h after the addition of the methyl vinyl dichlorosilane is finished, cooling the reaction liquid to room temperature, filtering, and rectifying the filtrate to obtain the methyl vinyl di (N-ethyl acetamido) silane.
On the basis of the technical scheme, the organic solvent is selected from one or more of toluene, xylene, petroleum ether and dioxane; preferably, the organic solvent is a mixed solution of toluene and dioxane; more preferably, the weight ratio of toluene to dioxane in the mixed solution of toluene and dioxane is 1: 1.
On the basis of the technical scheme, the acid-binding agent is selected from one or more of pyridine, triethylamine, 4-dimethylaminopyridine and triethanolamine; preferably, the acid-binding agent is a mixture of pyridine and triethylamine in a molar ratio of 1-1.05: 1-1.05.
On the basis of the technical scheme, the addition time of the methyl vinyl dichlorosilane is 1-3 h; preferably, the addition time of methylvinyldichlorosilane is 2 h.
On the basis of the technical scheme, the molar ratio of the N-ethyl acetamide to the methyl vinyl dichlorosilane to the acid-binding agent is 2:1: 2.1.
On the basis of the technical scheme, the pyrrole accounts for 1-3 per mill of the weight of the solution A.
The invention utilizes the mixed solvent and the mixed acid-binding agent, so that the reaction is carried out under mild conditions, the yield is higher, the process is simple, and the industrial production is convenient.
Detailed Description
The following is a further description of the technical solution of the present invention, and is not intended to limit the scope of the present invention.
Example 1
174 g of N-ethyl acetamide, 2 g of pyrrole, 82.95 g of pyridine, 106.05 g of triethylamine, 100 g of toluene and 100 g of dioxane are put into a 1000 ml four-neck flask, a thermometer, a condenser tube, a mechanical stirring device and a constant-pressure dropping funnel are inserted into the four-neck flask, and the flask is placed in an intelligent constant-temperature electric heating jacket; adding 141 g of methyl vinyl dichlorosilane into a constant-pressure dropping funnel, and starting a stirring and heating device; when the temperature in the flask rises to 70 ℃, dropwise adding methyl vinyl dichlorosilane, keeping the dropwise adding temperature at 70-80 ℃, and keeping the dropwise adding time at 2 hours; after the dropwise adding, heating to 90 ℃, and preserving heat for 3 hours; cooling to room temperature, filtering to obtain a crude product, and then rectifying and purifying to obtain 217 g of a product with the content of 97 percent, wherein the yield is 89.7 percent.
Example 2
174 g of N-ethyl acetamide, 2 g of pyrrole, 80.975 g of pyridine, 108.575 g of triethylamine, 100 g of toluene and 100 g of dioxane are put into a 1000 ml four-neck flask, a thermometer, a condenser tube, a mechanical stirring device and a constant-pressure dropping funnel are inserted into the four-neck flask, and the flask is placed in an intelligent constant-temperature electric heating jacket; adding 141 g of methyl vinyl dichlorosilane into a constant-pressure dropping funnel, and starting a stirring and heating device; when the temperature in the flask rises to 70 ℃, dropwise adding methyl vinyl dichlorosilane, keeping the dropwise adding temperature at 70-80 ℃, and keeping the dropwise adding time at 2 hours; after the dropwise adding, heating to 90 ℃, and preserving heat for 3 hours; cooling to room temperature, filtering to obtain a crude product, and then rectifying and purifying to obtain 216 g of a product with the content of 97 percent, wherein the yield is 89.3 percent.
Example 3
174 g of N-ethyl acetamide, 2 g of pyrrole, 84.925 g of pyridine, 103.525 g of triethylamine, 100 g of toluene and 100 g of dioxane are put into a 1000 ml four-neck flask, a thermometer, a condenser tube, a mechanical stirring device and a constant-pressure dropping funnel are inserted into the four-neck flask, and the flask is placed in an intelligent constant-temperature electric heating jacket; adding 141 g of methyl vinyl dichlorosilane into a constant-pressure dropping funnel, and starting a stirring and heating device; when the temperature in the flask rises to 70 ℃, dropwise adding methyl vinyl dichlorosilane, keeping the dropwise adding temperature at 70-80 ℃, and keeping the dropwise adding time at 2 hours; after the dropwise adding, heating to 90 ℃, and preserving heat for 3 hours; cooling to room temperature, filtering to obtain a crude product, and then rectifying and purifying to obtain 211 g of a product with the content of 97 percent, wherein the yield is 87.2 percent.
Example 4
174 g of N-ethyl acetamide, 2 g of pyrrole, 80.975 g of pyridine, 103.525 g of triethylamine, 100 g of toluene and 100 g of dioxane are put into a 1000 ml four-neck flask, a thermometer, a condenser tube, a mechanical stirring device and a constant-pressure dropping funnel are inserted into the four-neck flask, and the flask is placed in an intelligent constant-temperature electric heating jacket; adding 141 g of methyl vinyl dichlorosilane into a constant-pressure dropping funnel, and starting a stirring and heating device; when the temperature in the flask rises to 70 ℃, dropwise adding methyl vinyl dichlorosilane, keeping the dropwise adding temperature at 70-80 ℃, and keeping the dropwise adding time at 2 hours; after the dropwise adding, heating to 90 ℃, and preserving heat for 3 hours; cooling to room temperature, filtering to obtain crude product, then rectifying and purifying to obtain product 214 g with 97% content and 88.4% yield.
Example 5
174 g of N-ethyl acetamide, 2 g of pyrrole, 84.925 g of pyridine, 108.575 g of triethylamine, 100 g of toluene and 100 g of dioxane are put into a 1000 ml four-neck flask, a thermometer, a condenser tube, a mechanical stirring device and a constant-pressure dropping funnel are inserted into the four-neck flask, and the flask is placed in an intelligent constant-temperature electric heating jacket; adding 141 g of methyl vinyl dichlorosilane into a constant-pressure dropping funnel, and starting a stirring and heating device; when the temperature in the flask rises to 70 ℃, dropwise adding methyl vinyl dichlorosilane, keeping the dropwise adding temperature at 70-80 ℃, and keeping the dropwise adding time at 2 hours; after the dropwise adding, heating to 90 ℃, and preserving heat for 3 hours; cooling to room temperature, filtering to obtain a crude product, and then rectifying and purifying to obtain 212 g of a product with the content of 97 percent and the yield of 87.6 percent.
Example 6
174 g of N-ethyl acetamide, 2 g of pyrrole, 82.95 g of pyridine, 106.05 g of triethylamine, 100 g of toluene and 100 g of dioxane are put into a 1000 ml four-neck flask, a thermometer, a condenser tube, a mechanical stirring device and a constant-pressure dropping funnel are inserted into the four-neck flask, and the flask is placed in an intelligent constant-temperature electric heating jacket; adding 141 g of methyl vinyl dichlorosilane into a constant-pressure dropping funnel, and starting a stirring and heating device; when the temperature in the flask rises to 70 ℃, dropwise adding methyl vinyl dichlorosilane, keeping the dropwise adding temperature at 70-80 ℃, and keeping the dropwise adding time at 1 hour; after the dropwise adding, heating to 90 ℃, and preserving heat for 3 hours; cooling to room temperature, filtering to obtain a crude product, and then rectifying and purifying to obtain 200 g of a product with the content of 97 percent, wherein the yield is 82.6 percent.
Example 7
174 g of N-ethyl acetamide, 2 g of pyrrole, 82.95 g of pyridine, 106.05 g of triethylamine, 100 g of toluene and 100 g of dioxane are put into a 1000 ml four-neck flask, a thermometer, a condenser tube, a mechanical stirring device and a constant-pressure dropping funnel are inserted into the four-neck flask, and the flask is placed in an intelligent constant-temperature electric heating jacket; adding 141 g of methyl vinyl dichlorosilane into a constant-pressure dropping funnel, and starting a stirring and heating device; when the temperature in the flask rises to 70 ℃, dropwise adding methyl vinyl dichlorosilane, keeping the dropwise adding temperature at 70-80 ℃, and keeping the dropwise adding time at 3 hours; after the dropwise adding, heating to 90 ℃, and preserving heat for 3 hours; cooling to room temperature, filtering to obtain a crude product, and then rectifying and purifying to obtain 210 g of a product with the content of 97 percent and the yield of 86.8 percent.
Comparative example 1
174 g of N-ethyl acetamide, 2 g of pyrrole, 165.9 g of pyridine, 100 g of toluene and 100 g of dioxane are put into a 1000 ml four-neck flask, a thermometer, a condenser tube, a mechanical stirring device and a constant-pressure dropping funnel are inserted into the four-neck flask, and the flask is placed in an intelligent constant-temperature electric heating sleeve; adding 141 g of methyl vinyl dichlorosilane into a constant-pressure dropping funnel, and starting a stirring and heating device; when the temperature in the flask rises to 70 ℃, dropwise adding methyl vinyl dichlorosilane, keeping the dropwise adding temperature at 70-80 ℃, and keeping the dropwise adding time at 2 hours; after the dropwise adding, heating to 90 ℃, and preserving heat for 3 hours; cooling to room temperature, filtering to obtain a crude product, and then rectifying and purifying to obtain 180 g of a product with the content of 97 percent and the yield of 74.4 percent.
Comparative example 2
174 g of N-ethyl acetamide, 2 g of pyrrole, 86.9 g of pyridine, 111.1 g of triethylamine, 100 g of toluene and 100 g of dioxane are put into a 1000 ml four-neck flask, a thermometer, a condenser tube, a mechanical stirring device and a constant-pressure dropping funnel are inserted into the four-neck flask, and the flask is placed in an intelligent constant-temperature electric heating sleeve; adding 141 g of methyl vinyl dichlorosilane into a constant-pressure dropping funnel, and starting a stirring and heating device; when the temperature in the flask rises to 70 ℃, dropwise adding methyl vinyl dichlorosilane, keeping the dropwise adding temperature at 70-80 ℃, and keeping the dropwise adding time at 2 hours; after the dropwise adding, heating to 90 ℃, and preserving heat for 3 hours; cooling to room temperature, filtering to obtain a crude product, and then rectifying and purifying to obtain 150 g of a product with the content of 97 percent and the yield of 62 percent.
Comparative example 3
174 g of N-ethyl acetamide, 82.95 g of pyridine, 106.05 g of triethylamine, 100 g of toluene and 100 g of dioxane are put into a 1000 ml four-neck flask, a thermometer, a condenser tube, a mechanical stirring device and a constant-pressure dropping funnel are inserted into the four-neck flask, and the flask is placed in an intelligent constant-temperature electric heating sleeve; adding 141 g of methyl vinyl dichlorosilane into a constant-pressure dropping funnel, and starting a stirring and heating device; when the temperature in the flask rises to 70 ℃, dropwise adding methyl vinyl dichlorosilane, keeping the dropwise adding temperature at 70-80 ℃, and keeping the dropwise adding time at 2 hours; after the dropwise adding, heating to 90 ℃, and preserving heat for 3 hours; cooling to room temperature, filtering to obtain a crude product, and then rectifying and purifying to obtain 120 g of a product with the content of 97 percent and the yield of 49.6 percent.
Comparative example 4
174 g of N-ethyl acetamide, 2 g of pyrrole, 82.95 g of pyridine, 106.05 g of triethylamine and 200 g of toluene are put into a 1000 ml four-neck flask, a thermometer, a condenser tube, a mechanical stirring device and a constant pressure dropping funnel are inserted into the four-neck flask, and the flask is placed in an intelligent constant temperature electric heating sleeve; adding 141 g of methyl vinyl dichlorosilane into a constant-pressure dropping funnel, and starting a stirring and heating device; when the temperature in the flask rises to 70 ℃, dropwise adding methyl vinyl dichlorosilane, keeping the dropwise adding temperature at 70-80 ℃, and keeping the dropwise adding time at 2 hours; after the dropwise adding, heating to 90 ℃, and preserving heat for 3 hours; cooling to room temperature, filtering to obtain a crude product, and then rectifying and purifying to obtain 171 g of a product with the content of 97 percent and the yield of 70.7 percent.
Comparative example 5
174 g of N-ethyl acetamide, 2 g of pyrrole, 82.95 g of pyridine, 106.05 g of triethylamine and 200 g of dioxane are put into a 1000 ml four-neck flask, a thermometer, a condenser tube, a mechanical stirring device and a constant-pressure dropping funnel are inserted into the four-neck flask, and the flask is placed in an intelligent constant-temperature electric heating sleeve; adding 141 g of methyl vinyl dichlorosilane into a constant-pressure dropping funnel, and starting a stirring and heating device; when the temperature in the flask rises to 70 ℃, dropwise adding methyl vinyl dichlorosilane, keeping the dropwise adding temperature at 70-80 ℃, and keeping the dropwise adding time at 2 hours; after the dropwise adding, heating to 90 ℃, and preserving heat for 3 hours; cooling to room temperature, filtering to obtain a crude product, and then rectifying and purifying to obtain 163 g of a product with the content of 97 percent and the yield of 67.4 percent.
Comparative example 6
174 g of N-ethyl acetamide, 2 g of pyrrole, 212.1 g of triethylamine, 100 g of toluene and 100 g of dioxane are put into a 1000 ml four-neck flask, a thermometer, a condenser tube, a mechanical stirring device and a constant-pressure dropping funnel are inserted into the four-neck flask, and the flask is placed in an intelligent constant-temperature electric heating sleeve; adding 141 g of methyl vinyl dichlorosilane into a constant-pressure dropping funnel, and starting a stirring and heating device; when the temperature in the flask rises to 70 ℃, dropwise adding methyl vinyl dichlorosilane, keeping the dropwise adding temperature at 70-80 ℃, and keeping the dropwise adding time at 3 hours; after the dropwise adding, heating to 90 ℃, and preserving heat for 3 hours; cooling to room temperature, filtering to obtain a crude product, and then rectifying and purifying to obtain 170 g of a product with the content of 97 percent, wherein the yield is 70.3 percent.
Comparative example 7
174 g of N-ethyl acetamide, 2-N-butylamine, 82.95 g of pyridine, 106.05 g of triethylamine, 100 g of toluene and 100 g of dioxane are put into a 1000 ml four-neck flask, a thermometer, a condenser tube, a mechanical stirring device and a constant-pressure dropping funnel are inserted into the four-neck flask, and the flask is placed in an intelligent constant-temperature electric heating jacket; adding 141 g of methyl vinyl dichlorosilane into a constant-pressure dropping funnel, and starting a stirring and heating device; when the temperature in the flask rises to 70 ℃, dropwise adding methyl vinyl dichlorosilane, keeping the dropwise adding temperature at 70-80 ℃, and keeping the dropwise adding time at 2 hours; after the dropwise adding, heating to 90 ℃, and preserving heat for 3 hours; cooling to room temperature, filtering to obtain a crude product, and then rectifying and purifying to obtain 115 g of a product with the content of 97 percent, wherein the yield is 47.5 percent.
Comparative example 8
174 g of N-ethyl acetamide, 2 g of tert-butylamine, 82.95 g of pyridine, 106.05 g of triethylamine, 100 g of toluene and 100 g of dioxane are put into a 1000 ml four-neck flask, a thermometer, a condenser tube, a mechanical stirring device and a constant-pressure dropping funnel are inserted into the four-neck flask, and the flask is placed in an intelligent constant-temperature electric heating jacket; adding 141 g of methyl vinyl dichlorosilane into a constant-pressure dropping funnel, and starting a stirring and heating device; when the temperature in the flask rises to 70 ℃, dropwise adding methyl vinyl dichlorosilane, keeping the dropwise adding temperature at 70-80 ℃, and keeping the dropwise adding time at 2 hours; after the dropwise adding, heating to 90 ℃, and preserving heat for 3 hours; cooling to room temperature, filtering to obtain a crude product, and then rectifying and purifying to obtain 125 g of a product with the content of 97 percent and the yield of 51.7 percent.
The above embodiments are merely for clearly illustrating the embodiments and are not intended to limit the embodiments. Other variants and modifications of the invention, which are obvious to those skilled in the art and can be made on the basis of the above description, are not necessary or exhaustive for all embodiments, and are therefore within the scope of the invention.
Claims (10)
1. A method for preparing methylvinyldi (N-ethylacetamido) silane, which is characterized by comprising the following steps: adding pyrrole catalyst, N-ethyl acetamide with the molar ratio of 2:1:2.05-2.15, methyl vinyl dichlorosilane and an acid-binding agent into an organic solvent to obtain a solution A; and slowly adding methyl vinyl dichlorosilane into the solution A under the stirring condition at 70-80 ℃, preserving the temperature of the reaction liquid at 85-95 ℃ for 2-4h after the addition of the methyl vinyl dichlorosilane is finished, cooling the reaction liquid to room temperature, filtering, and rectifying the filtrate to obtain the methyl vinyl di (N-ethyl acetamido) silane.
2. The process for preparing methylvinyldi (N-ethylacetamido) silane as claimed in claim 1, wherein: the organic solvent is one or more of toluene, xylene, petroleum ether and dioxane.
3. The process for preparing methylvinyldi (N-ethylacetamido) silane as claimed in claim 2, wherein: the organic solvent is a mixed solution of toluene and dioxane.
4. The process for preparing methylvinyldi (N-ethylacetamido) silane as claimed in claim 3, wherein: in the mixed solution of toluene and dioxane, the weight ratio of toluene to dioxane is 1: 1.
5. The process for preparing methylvinyldi (N-ethylacetamido) silane as claimed in claim 1, wherein: the acid-binding agent is one or more of pyridine, triethylamine, 4-dimethylamino pyridine and triethanolamine.
6. The process for producing methylvinyldi (N-ethylacetamido) silane as claimed in claim 1 or 5, wherein: the acid-binding agent is a mixture of pyridine and triethylamine in a molar ratio of 1-1.05: 1-1.05.
7. The process for preparing methylvinyldi (N-ethylacetamido) silane as claimed in claim 1, wherein: the addition time of the methyl vinyl dichlorosilane is 1-3 h.
8. The process for producing methylvinyldi (N-ethylacetamido) silane as claimed in claim 1 or 7, wherein: the addition time of the methylvinyldichlorosilane is 2 h.
9. The process for preparing methylvinyldi (N-ethylacetamido) silane as claimed in claim 1, wherein: the molar ratio of the N-ethyl acetamide to the methyl vinyl dichlorosilane to the acid-binding agent is 2:1: 2.1.
10. The process for preparing methylvinyldi (N-ethylacetamido) silane as claimed in claim 1, wherein: the pyrrole accounts for 1-3 per mill of the weight of the solution A.
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| CN113501842A (en) * | 2021-08-17 | 2021-10-15 | 石家庄圣泰化工有限公司 | Preparation method of trimethylsilyl 2- (fluorosulfonyl) difluoroacetate |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4467037A (en) * | 1982-03-01 | 1984-08-21 | The Curators Of The University Of Missouri | Silylation of amino acids |
| US4683251A (en) * | 1986-06-20 | 1987-07-28 | Toray Silicone Co., Ltd. | Room temperature-curable organopolysiloxane composition containing a photosensitizer |
| JPH06329912A (en) * | 1993-05-25 | 1994-11-29 | Toray Dow Corning Silicone Co Ltd | Room-temperature-curable organopolysiloxane composition |
| CN1670098A (en) * | 2005-02-25 | 2005-09-21 | 华南理工大学 | Bicomponent normal temperature crosslinked aqueous organosilicon rubber waterproof paint and method for preparing same |
| CN103732598A (en) * | 2011-04-05 | 2014-04-16 | 佩普蒂辛塔公司 | Industrial process for the preparation of N-alkyl-N-trialkylsilylamides |
| CN104282940A (en) * | 2013-07-08 | 2015-01-14 | 三星Sdi株式会社 | Electrolyte for lithium secondary battery and lithium secondary battery including the same |
| CN105229056A (en) * | 2013-03-28 | 2016-01-06 | 道康宁公司 | Organosiloxane composition and coating, finished product, method and purposes |
-
2019
- 2019-12-19 CN CN201911319650.1A patent/CN110964050B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4467037A (en) * | 1982-03-01 | 1984-08-21 | The Curators Of The University Of Missouri | Silylation of amino acids |
| US4683251A (en) * | 1986-06-20 | 1987-07-28 | Toray Silicone Co., Ltd. | Room temperature-curable organopolysiloxane composition containing a photosensitizer |
| JPH06329912A (en) * | 1993-05-25 | 1994-11-29 | Toray Dow Corning Silicone Co Ltd | Room-temperature-curable organopolysiloxane composition |
| CN1670098A (en) * | 2005-02-25 | 2005-09-21 | 华南理工大学 | Bicomponent normal temperature crosslinked aqueous organosilicon rubber waterproof paint and method for preparing same |
| CN103732598A (en) * | 2011-04-05 | 2014-04-16 | 佩普蒂辛塔公司 | Industrial process for the preparation of N-alkyl-N-trialkylsilylamides |
| CN105229056A (en) * | 2013-03-28 | 2016-01-06 | 道康宁公司 | Organosiloxane composition and coating, finished product, method and purposes |
| CN104282940A (en) * | 2013-07-08 | 2015-01-14 | 三星Sdi株式会社 | Electrolyte for lithium secondary battery and lithium secondary battery including the same |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113501842A (en) * | 2021-08-17 | 2021-10-15 | 石家庄圣泰化工有限公司 | Preparation method of trimethylsilyl 2- (fluorosulfonyl) difluoroacetate |
| CN113501842B (en) * | 2021-08-17 | 2022-11-15 | 河北圣泰材料股份有限公司 | Preparation method of trimethylsilyl 2- (fluorosulfonyl) difluoroacetate |
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