CN113754687B - Preparation method of bis (N-methylbenzamide) ethoxymethylsilane - Google Patents
Preparation method of bis (N-methylbenzamide) ethoxymethylsilane Download PDFInfo
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- CN113754687B CN113754687B CN202111116305.5A CN202111116305A CN113754687B CN 113754687 B CN113754687 B CN 113754687B CN 202111116305 A CN202111116305 A CN 202111116305A CN 113754687 B CN113754687 B CN 113754687B
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- methylbenzamide
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- methyldichlorosilane
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- BLEJWUIEUACHKH-UHFFFAOYSA-N n-[[benzoyl(methyl)amino]-ethoxy-methylsilyl]-n-methylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(C)[Si](C)(OCC)N(C)C(=O)C1=CC=CC=C1 BLEJWUIEUACHKH-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 28
- NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 claims abstract description 25
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000005048 methyldichlorosilane Substances 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 16
- 238000000926 separation method Methods 0.000 claims abstract description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 239000013067 intermediate product Substances 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 16
- 229910021529 ammonia Inorganic materials 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims description 8
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 claims description 2
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 claims description 2
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000003431 cross linking reagent Substances 0.000 abstract description 7
- 238000005265 energy consumption Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 229910000077 silane Inorganic materials 0.000 abstract description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract description 4
- 230000007547 defect Effects 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 4
- 150000003863 ammonium salts Chemical class 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 3
- 238000005580 one pot reaction Methods 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000004945 silicone rubber Substances 0.000 description 8
- AXTPGQHJFRSSQJ-UHFFFAOYSA-N dichloro-ethoxy-methylsilane Chemical compound CCO[Si](C)(Cl)Cl AXTPGQHJFRSSQJ-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 229920002379 silicone rubber Polymers 0.000 description 7
- 239000012295 chemical reaction liquid Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 3
- -1 acyloxy silane Chemical compound 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000005055 methyl trichlorosilane Substances 0.000 description 2
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 2
- 229910007991 Si-N Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910006294 Si—N Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- PELBZXLLQLEQAU-UHFFFAOYSA-N chloro-diethoxy-methylsilane Chemical compound CCO[Si](C)(Cl)OCC PELBZXLLQLEQAU-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical class [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- IVHXEBVFCNBWED-UHFFFAOYSA-N prop-1-en-2-yloxysilane Chemical compound CC(=C)O[SiH3] IVHXEBVFCNBWED-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229920002631 room-temperature vulcanizate silicone Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention relates to the technical field of silane crosslinking agents, and provides a preparation method of bis (N-methylbenzamide) ethoxymethylsilane, which aims to overcome the defects of more byproducts, low yield, difficult separation and purification and higher production energy consumption of the existing preparation method of bis (N-methylbenzamide) ethoxymethylsilane. The bis (N-methylbenzamide) ethoxymethylsilane is obtained by using methyl dichlorosilane as a starting material and sequentially reacting with N-methylbenzamide and ethanol by a one-pot method, the obtained bis (N-methylbenzamide) ethoxymethylsilane is high in purity, high in yield, easy to separate and purify, low in production energy consumption, the obtained ammonium salt can be recycled, the generated three wastes are few, and the atomic utilization rate is high.
Description
Technical Field
The invention relates to the technical field of silane crosslinking agents, in particular to a preparation method of bis (N-methylbenzamide) ethoxymethylsilane.
Background
The room temperature vulcanized silicone rubber belongs to a new material, and has the most remarkable characteristics of being capable of being cured in situ at room temperature without heating, and being extremely convenient to use. Therefore, the organic silicon compound is rapidly becoming an important component part of the whole organic silicon product, is widely applied to various industries such as building, decoration, automobiles, electronics, solar energy and the like, and continuously develops new applications. Room temperature vulcanized silicone rubber has a plurality of systems. There are generally ketoxime-removing systems using ketoxime silane as a crosslinking agent, acid-removing systems using acyloxy silane as a crosslinking agent, alcohol-removing systems using alkoxysilane as a crosslinking agent, and acetone-removing systems using isopropenyloxy silane as a crosslinking agent. The above systems are characterized by various application ranges.
The low modulus silicone rubber is applied to large deformation places and wide joint places due to low stress and high elongation, and is applied to airfield runways, subway station joints, roof large joints, container assembly, daily necessities and the like. In recent years, with the development of fabricated structures, the demand for low modulus silicone rubber has increased more rapidly.
The low modulus silicone rubber is prepared on the market by using high viscosity 107 base rubber, difunctional ketoxime cross-linking agent, phenyltributylketoxime silane, methyl vinyl di (N-methylacetamide) silane and the like as raw materials. The silicone rubber prepared by the method has the defects of low viscosity, poor cohesiveness, insufficient modulus, insufficient relative elongation and the like.
The RTV silicone rubber prepared by adopting the bis (N-methylbenzamide) ethoxymethyl silane has the advantages of quick solidification, low modulus, very high elongation, good adhesion with various base materials (including various metals, coating surfaces and the like), good high and low temperature resistance, good water resistance and the like, and is the silicone rubber with very excellent comprehensive performance. The development of a preparation method of high-quality bis (N-methylbenzamide) ethoxymethylsilane has important research significance.
In the prior art, methyl trichlorosilane and ethanol are often adopted to carry out incomplete esterification reaction to obtain a mixture of methyl ethoxy dichlorosilane, methyl diethoxy chlorosilane and methyl triethoxy silane, then the mixture is purified to obtain methyl ethoxy dichlorosilane, and then the methyl ethoxy dichlorosilane and N-methylbenzamide are used to carry out reaction to obtain bis (N-methylbenzamide) ethoxy methylsilane.
Chinese patent publication No. CN202010037461.1 discloses a method for preparing bis (N-methylbenzamide) ethoxymethylsilane, comprising the steps of: (1) Methyl trichlorosilane and methyl triethoxysilane are used as raw materials, a catalyst is added, and under the protection of inert gas, heating reaction, filtration and rectification are carried out to obtain methyl ethoxy dichlorosilane; (2) Uniformly mixing N-methylbenzamide and an organic solvent, reacting under heating, introducing ammonia gas, adding the methyl ethoxy dichlorosilane obtained in the step (1), continuously reacting, filtering, and distilling to obtain the bis (N-methylbenzamide) ethoxy methylsilane. The method has the defects that the process intermediate needs to be purified and separated, the reaction steps are increased, the reaction temperature of the two steps is higher, and the energy consumption is higher.
Disclosure of Invention
The invention aims to overcome the defects of more byproducts, low yield, difficult separation and purification and higher production energy consumption of the existing bis (N-methylbenzamide) ethoxymethylsilane preparation method, and provides the preparation method of the bis (N-methylbenzamide) ethoxymethylsilane, which has the advantages of less byproducts, high yield, easy separation and purification and lower production energy consumption.
In order to achieve the above object, the present invention adopts the following technical scheme:
a method for preparing bis (N-methylbenzamide) ethoxymethylsilane, comprising the steps of:
A. dropwise adding N-methylbenzamide into a methyldichlorosilane solution, heating, adding an acid binding agent, and reacting to obtain an intermediate product bis (N-methylbenzamide) methylhydrosilane;
B. and (3) adding a catalyst and ethanol into the intermediate product system in the step (A) to continue the reaction, and separating to obtain the bis (N-methylbenzamide) ethoxymethylsilane.
The method of the invention completes the preparation of bis (N-methylbenzamide) ethoxymethylsilane by a one-pot method without separating and purifying intermediate products, firstly forms Si-N bond with N-methylbenzamide and methyldichlorosilane to obtain intermediate product bis (N-methylbenzamide) methylhydrosilane, and then completes the substitution of ethoxy on Si atom H by ethanol under the action of a catalyst.
Preferably, in the step A, the molar ratio of the N-methylbenzamide to the methyldichlorosilane is 2-2.3:1.
Preferably, in the step A, the solvent of the methyl dichlorosilane solution is at least one of toluene, xylene and petroleum ether; the acid binding agent is ammonia.
Ammonia is selected as an acid binding agent, so that the ammonium salt after the reaction is finished is easy to separate, can be reused as a fertilizer raw material, and does not generate wastewater.
Preferably, in the step A, the molar ratio of ammonia to methyl dichlorosilane is 2-2.4:1.
Preferably, in the step A, the reaction temperature is 60-120 ℃ and the reaction time is 1-3 h.
Preferably, in the step B, the catalyst is a metal or molecular sieve catalyst with dehydrogenation function, the active component comprises at least one of nickel nitrate, nickel sulfate and nickel chloride, and the molar ratio of the catalyst to methyl dichlorosilane is 0.005-0.1%.
Preferably, in the step B, the molar ratio of the ethanol to the methyl dichlorosilane is 0.95-1.05:1.
Preferably, in the step B, the reaction temperature is 50-80 ℃ and the reaction time is 3-5 h.
By adopting the technical scheme, the invention has the following beneficial effects: according to the invention, methyl dichlorosilane is used as a starting material, and is reacted with N-methylbenzamide and ethanol successively to obtain bis (N-methylbenzamide) ethoxymethylsilane, so that the obtained bis (N-methylbenzamide) ethoxymethylsilane has high purity, high yield, easy separation and purification, low production energy consumption, recycling of the obtained ammonium salt, less three wastes and high atom utilization rate.
Drawings
FIG. 1 is a reaction equation of the present invention.
FIG. 2 is a gas chromatogram of bis (N-methylbenzamide) ethoxymethylsilane of example 1 of the present invention.
Description of the embodiments
The invention is further described below in connection with the following detailed description.
A preparation method of bis (N-methylbenzamide) ethoxymethylsilane, the reaction equation of which is shown in figure 1, comprises the following steps:
A. adding N-methylbenzamide solution with 2-2.3 times of the molar weight of methyl dichlorosilane into a glass lining kettle, heating to 60-120 ℃, introducing ammonia gas with 2-2.4 times of the molar weight of methyl dichlorosilane for circulation, dropwise adding methyl dichlorosilane for reaction, and reacting for 1-3 hours to obtain an intermediate product bis (N-methylbenzamide) methylhydrosilane;
B. and C, controlling the temperature in the kettle to be 40-80 ℃, closing ammonia circulation, evacuating tail gas, adding nickel chloride catalyst into the intermediate product system in the step A, adding ethanol with the same molar weight as methyl dichlorosilane for continuous reaction, keeping the constant pressure in the kettle, continuously reacting for 3-5 h, filtering the reaction liquid, and vacuum distilling the filtrate to separate the solvent to obtain bis (N-methylbenzamide) ethoxymethylsilane.
Example 1
A. Adding 1000kg of N-methylbenzamide into a 3000L glass lining kettle, adding 1000L of toluene, replacing nitrogen, stirring and heating to 60 ℃, introducing 120kg of ammonia gas at a speed of 12.2kg/hr, starting an ammonia gas circulator for circulation, dropwise adding 380kg of methyldichlorosilane at a speed of 40 kg/hr for reaction, and obtaining an intermediate product bis (N-methylbenzamide) methylhydrosilane after the dropwise addition is completed for 3 hours;
B. the temperature in the kettle is controlled at 50 ℃, ammonia circulation is closed, tail gas is emptied, 100g of nickel chloride catalyst is added into the intermediate product system in the step A, 153kg of ethanol is dripped for continuous reaction, the constant pressure in the kettle is kept, the reaction liquid is filtered after the continuous reaction is carried out for 5 hours, filter residues are transported outwards, the filtrate is distilled in vacuum to separate toluene, 1130kg of bis (N-methylbenzamide) ethoxymethylsilane is obtained, the integral ratio of the peak area of the product is 94.9%, the yield is 91.5%, and the peak height and the peak area of impurity peaks are relatively smaller except the solvent peak.
Example 2
A. Adding 1000kg of N-methylbenzamide into a 3000L glass lining kettle, adding 1000L of 120# petroleum ether, replacing nitrogen, stirring and heating to 120 ℃, introducing 120kg of ammonia gas at a speed of 12.2kg/hr, starting an ammonia gas circulator to circulate, dropwise adding 380kg of methyl dichlorosilane at a speed of 40 kg/hr for reaction, and reacting for 1h after the dropwise adding is finished to obtain an intermediate product bis (N-methylbenzamide) methylhydrosilane;
B. and (3) controlling the temperature in the kettle to be 80 ℃, closing ammonia circulation, evacuating tail gas, adding 100g of nickel chloride catalyst into the intermediate product system in the step A, dropwise adding 153kg of ethanol for continuous reaction, keeping the constant pressure in the kettle, filtering the reaction liquid after the continuous reaction for 3 hours, transporting filter residues outwards, and vacuum distilling the filtrate to separate petroleum ether to obtain 1135kg of bis (N-methylbenzamide) ethoxymethylsilane, wherein the product peak area percentage is 94.8%, and the yield is 91.5%.
Example 3
A. Adding 1000kg of N-methylbenzamide into a 3000L glass lining kettle, adding 1000L of dimethylbenzene, replacing nitrogen, stirring and heating to 90 ℃, introducing 120kg of ammonia gas at a speed of 12.2kg/hr, starting an ammonia gas circulator for circulation, dropwise adding 380kg of methyldichlorosilane at a speed of 40 kg/hr for reaction, and reacting for 2 hours after the dropwise adding is finished to obtain an intermediate product bis (N-methylbenzamide) methylhydrosilane;
B. and (3) controlling the temperature in the kettle to be 80 ℃, closing ammonia circulation, evacuating tail gas, adding 100g of nickel chloride catalyst into the intermediate product system in the step A, dropwise adding 153kg of ethanol for continuous reaction, keeping the constant pressure in the kettle, filtering the reaction liquid after the continuous reaction for 4 hours, transporting filter residues outwards, and vacuum distilling the filtrate to separate dimethylbenzene to obtain 1140kg of bis (N-methylbenzamide) ethoxymethylsilane, wherein the product peak area percentage is 95.5%, and the yield is 92.5%.
Comparative example 1
The reaction temperature in step B of comparative example 1 was stabilized at 40 ℃ as compared with example 1.
A. Adding 1000kg of N-methylbenzamide into a 3000L glass lining kettle, adding 1000L of toluene, replacing nitrogen, stirring and heating to 60 ℃, introducing 120kg of ammonia gas at a speed of 12.2kg/hr, starting an ammonia gas circulator for circulation, dropwise adding 380kg of methyldichlorosilane at a speed of 40 kg/hr for reaction, and obtaining an intermediate product bis (N-methylbenzamide) methylhydrosilane after the dropwise addition is completed for 3 hours;
B. and (3) controlling the temperature in the kettle to 40 ℃, closing ammonia circulation, evacuating tail gas, adding 100g of nickel chloride catalyst into the intermediate product system in the step A, dropwise adding 153kg of ethanol for continuous reaction, keeping the constant pressure in the kettle, filtering the reaction liquid after the continuous reaction for 5 hours, transporting filter residues outwards, and separating toluene from filtrate by vacuum distillation to obtain 1100kg of bis (N-methylbenzamide) ethoxymethylsilane crude product, wherein 16.3% of the crude product is bis (N-methylbenzamide) methylhydrosilane, the peak area percentage of the target product is 78.9%, and the yield is 73.6%.
Comparative example 2
In comparison with example 1, the reaction temperature in step A of comparative example 2 was controlled to 40 DEG C
A. Adding 1000kg of N-methylbenzamide into a 3000L glass lining kettle, adding 1000L of toluene, replacing nitrogen, stirring and heating to 40 ℃, introducing 120kg of ammonia gas at a speed of 12.2kg/hr, starting an ammonia gas circulator for circulation, dropwise adding 380kg of methyldichlorosilane at a speed of 40 kg/hr for reaction, and obtaining an intermediate product bis (N-methylbenzamide) methylhydrosilane after the dropwise addition is completed for 3 hours;
B. and (3) controlling the temperature in the kettle to be 50 ℃, closing ammonia circulation, evacuating tail gas, adding 100g of nickel chloride catalyst into the intermediate product system in the step A, dropwise adding 153kg of ethanol for continuous reaction, keeping the constant pressure in the kettle, filtering the reaction liquid after the continuous reaction for 5 hours, transporting filter residues outwards, vacuum distilling filtrate to separate toluene to obtain 1130kg of crude bis (N-methylbenzamide) ethoxymethylsilane, wherein the product peak area percentage is 58.7%, and the yield is 56.6%.
The above description is only of the preferred embodiments of the present invention, and is not intended to limit the invention in any way, but other variations and modifications are possible without departing from the technical solution described in the claims.
Claims (8)
1. A method for preparing bis (N-methylbenzamide) ethoxymethylsilane, comprising the steps of:
A. dropwise adding N-methylbenzamide into a methyl dichlorosilane solution, heating, adding an acid-binding agent, and reacting to obtain an intermediate product bis (N-methylbenzamide) methylhydrosilane, wherein the reaction temperature is 60-120 ℃, and the acid-binding agent is ammonia;
B. and C, adding a catalyst and ethanol into the intermediate product system in the step A for continuous reaction, wherein the reaction temperature is 50-80 ℃, the catalyst is a metal or molecular sieve catalyst with dehydrogenation function, and the active ingredients comprise at least one of nickel nitrate, nickel sulfate and nickel chloride, and the bis (N-methylbenzamide) ethoxymethylsilane is obtained by separation.
2. The method for preparing bis (N-methylbenzamide) ethoxymethylsilane according to claim 1, wherein in the step A, the molar ratio of N-methylbenzamide to methyldichlorosilane is 2.1-2.3:1.
3. The method for preparing bis (N-methylbenzamide) ethoxymethylsilane according to claim 1, wherein in the step a, the solvent of the methyldichlorosilane solution is at least one of toluene, xylene and petroleum ether.
4. The method for preparing bis (N-methylbenzamide) ethoxymethylsilane according to claim 1, wherein in the step A, the molar ratio of ammonia to methyldichlorosilane is 2-2.4:1.
5. The method for preparing bis (N-methylbenzamide) ethoxymethylsilane according to claim 1, wherein in the step A, the reaction time is 1-3 hours.
6. The method for preparing bis (N-methylbenzamide) ethoxymethylsilane according to claim 1, wherein in the step B, the molar ratio of the catalyst to methyldichlorosilane is 0.005-0.1%.
7. The method for preparing bis (N-methylbenzamide) ethoxymethylsilane according to claim 1, wherein in the step B, the molar ratio of ethanol to methyldichlorosilane is 0.95-1.05:1.
8. The method for preparing bis (N-methylbenzamide) ethoxymethylsilane according to claim 1, wherein in the step B, the reaction time is 3-5 hours.
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| CN102199169A (en) * | 2011-04-11 | 2011-09-28 | 南京工业大学 | Novel preparation method of organic amido silane |
| CN105131028A (en) * | 2015-09-06 | 2015-12-09 | 浙江衢州硅宝化工有限公司 | Preparation method of methyl triethoxysilane |
| CN111285896A (en) * | 2020-01-14 | 2020-06-16 | 浙江衢州硅宝化工有限公司 | Preparation method of bis (N-methylbenzamide) ethoxymethylsilane |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102199169A (en) * | 2011-04-11 | 2011-09-28 | 南京工业大学 | Novel preparation method of organic amido silane |
| CN105131028A (en) * | 2015-09-06 | 2015-12-09 | 浙江衢州硅宝化工有限公司 | Preparation method of methyl triethoxysilane |
| CN111285896A (en) * | 2020-01-14 | 2020-06-16 | 浙江衢州硅宝化工有限公司 | Preparation method of bis (N-methylbenzamide) ethoxymethylsilane |
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