CN102863465A - Preparation method for methyl phenyl di-alkoxy silane - Google Patents
Preparation method for methyl phenyl di-alkoxy silane Download PDFInfo
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- CN102863465A CN102863465A CN2012103838276A CN201210383827A CN102863465A CN 102863465 A CN102863465 A CN 102863465A CN 2012103838276 A CN2012103838276 A CN 2012103838276A CN 201210383827 A CN201210383827 A CN 201210383827A CN 102863465 A CN102863465 A CN 102863465A
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- aminomethyl phenyl
- halobenzene
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- dialkoxy silicane
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Abstract
The invention discloses a preparation method for methyl phenyl di-alkoxy silane and relates to preparation methods of organosilicone monomers. The method includes: taking bromobenzene (or chlorobenzene, iodobenzene), MeSi(Y)3 (the Y in a formula can be methoxy group, chloroethoxy) as raw materials, taking tetrahydrofuran (or methyltetrahydrofuran, diethyl ester and toluene) as solvents and reacting with magnesium by the one-step method. The content of methylphenylsilane in reactant is about 90%, The draining method is adopted to directly distill to obtain a crude product, the methyl phenyl di-alkoxy silane with the purity higher than 99% is obtained by rectification, and the product yield is higher than 70%. The preparation method for methyl phenyl di-alkoxy silane is reduced in side reaction, simplified in process, improved in product yield, simple in extraction and purification mode processes, lowered in energy consumption, energy-saving and environment-friendly.
Description
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Technical field
The present invention relates to a kind of preparation method of organosilane monomer, say in detail it is the preparation method of the aminomethyl phenyl dialkoxy silicane that a kind of technique is simple, product yield is high, production cost is low.
Background technology
Phenyl ring is a kind of cyclic conjugated system, attack to thermooxidizing and ray has good tolerance, phenyl is introduced in the polysiloxane molecule, give high temperature resistant, the radiation hardness characteristic of organosilicon material excellence, the simultaneously introducing of phenyl ring, destroyed the molecular structure regularity, made polysiloxane have excellent resistance to low temperature, phenyl ring can improve the refractive index of organosilicon material in addition.Therefore the organosilicon material that contains the methylphenyl siloxane chain link has high temperature resistant, low temperature resistant, radiation hardness and has the series of characteristics such as high refractive index, is widely used in the high-tech areas such as space flight, aviation, photoelectricity.
The aminomethyl phenyl dialkoxy silicane is the important monomer of preparation methyl phenyl silicone oil, aminomethyl phenyl rubber, aminomethyl phenyl resin and LED glue, has good market outlook.
Synthetic direct method, pyrocondensation method, sodium contracting method, the Grignard etc. of mainly containing of present aminomethyl phenyl monomer.The patent CN101628917A of pyrocondensation method such as the application of novel material company limited of Jiangsu HTC, prepared by sodium condensation method such as Huaye Medicine Chemical Co., Ltd., Yancheng City apply for a patent CN101077877A, Grignard such as US 5596120, US7084206, do reactant with METHYL TRICHLORO SILANE, adopt Ge Shi, replace two-step approach.
Direct method, pyrocondensation method are because temperature of reaction is too high, can produce more polychlorobiphenyl in the reaction process, polychlorobiphenyl is very stable under field conditions (factors), can long-term existence be decomposed, and more fearful is, and it has very strong reproduction, teratogenesis, the carcinogenesis of affecting to organism.In addition, these two kinds of method by products give separation very difficult more.Sodium contracting rule sodium Metal 99.5, all there are certain risk in the transportation of sodium Metal 99.5, storage and use, especially in the sodium mediated condensated reaction process, usually have in the sodium salt that a small amount of sodium Metal 99.5 is wrapped in generation, accidentally just may initiation fire.The shortcoming of Grignard is will be with more solvent, but by contrast, Grignard relative environmental protection and security are good and yield is also higher.U.S. Dow Corning company is raw material with chlorosilane always, adopts the Grignard synthesis of phenyl chlorosilane.The Si-Cl key of chlorosilane very easily is hydrolyzed, and just can be hydrolyzed in air and generate HCl, and HCl has very strong water-retaining capacity, and suction just becomes hydrochloric acid, and the deep-etching effect is arranged.
Summary of the invention
The objective of the invention is to solve above-mentioned the deficiencies in the prior art, provide a kind of technique simple, the preparation method of the aminomethyl phenyl dialkoxy silicane that product yield is high, production cost is low.
Concrete synthetic route is as follows:
Wherein: X is a kind of among Cl, Br, the I; Y is OCH3 or OC2H5.
A kind of preparation method of aminomethyl phenyl dialkoxy silicane is characterized in that comprising the steps:
A, press reaction mass mole proportioning, halobenzene: Mg:MeSi(Y)
3=1:1-1.5:1-5 chooses reaction mass;
B, to stir, in the reactor of reflux, doubly solvent of the halobenzene, Mg quality 6-20 that adds whole Mg, 2%-3%, the iodine of Mg quality 0.01%-0.05% stir, are heated to 30-110 ℃ of initiation reactions;
C, in reactor, add MeSi(Y)
3, stir, be heated to 30-110 ℃;
D, with remaining halobenzene and Mg quality 3-16 solvent doubly, be added drop-wise in the reactor, keep 30-110 ℃ in the reactor, dripped then under 30-100 ℃ of temperature insulation reaction 1-5 hour in about 3-10 hour;
E, fully after the reaction, with decanting process steam crude product, rectifying obtains highly purified aminomethyl phenyl dialkoxy silicane again;
Wherein Me is CH3, and Y is OCH3 or OC2H5.
Halobenzene described in the present invention, Mg, MeSi(Y)
3The optimum molar proportioning is halobenzene: Mg:MeSi(Y)
3=1:1.1:1.5.
In b, c, the step, behind the adding reactant, be heated to 50-70 ℃ described in the present invention.Optimum temps is 60 ℃.
In the d step, remain on 50-70 ℃ in the reactor described in the present invention.
Halobenzene described in the present invention is a kind of in chlorobenzene, bromobenzene, the iodobenzene, preferred bromobenzene.
Solvent described in the present invention is one or more in the organic solvents such as the ethers such as tetrahydrofuran (THF), methyltetrahydrofuran, ether, toluene, benzene, preferred tetrahydrofuran (THF).
MeSi(Y described in the present invention)
3In, Y is OC2H5.
Decanting process: namely reaction product is without other any processing, direct heating, and distillation obtains thick product.
The present invention is by above-mentioned reactions steps, with halobenzene, MeSi(Y)
3Be raw material, take tetrahydrofuran (THF) etc. as solvent, carry out Ge Shi, one step of substitution reaction with MAGNESIUM METAL and finish reaction, after reaction finishes, with decanting process steam crude product, rectifying obtains product again.Ge Shi, one step of substitution reaction finish, and have reduced side reaction, have simplified technique, have improved product yield.Reaction product is extracted and is adopted decanting process, at first reclaims reaction solvent, then steams thick product, and rectifying obtains high purity product again, and this product extracts, purification mode technique is simple, has reduced energy consumption, energy-conserving and environment-protective.
Embodiment
Following examples are used for explanation the present invention, but are not used for limiting the scope of the invention.
A kind of preparation method of aminomethyl phenyl dialkoxy silicane is characterized in that comprising the steps:
A, press reaction mass mole proportioning, halobenzene: Mg:MeSi(Y)
3=1:1-1.5:1-5 chooses reaction mass;
B, to stir, in the reactor of reflux, doubly solvent of the halobenzene, Mg quality 6-20 that adds whole Mg, 2%-3%, the iodine of Mg quality 0.01%-0.05% stir, are heated to 30-110 ℃ of initiation reactions;
C, in reactor, add MeSi(Y)
3, stir, be heated to 30-110 ℃;
D, with remaining halobenzene and Mg quality 3-16 solvent doubly, be added drop-wise in the reactor, keep 30-110 ℃ in the reactor, dripped then under 30-100 ℃ of temperature insulation reaction 1-5 hour in about 3-10 hour;
E, fully after the reaction, with decanting process steam crude product, rectifying obtains highly purified aminomethyl phenyl dialkoxy silicane again;
Me is CH in the above-mentioned chemical formula
3, Y is OCH3 or OC2H5, the preferred OC2H5 of Y.
Embodiment 1
Choose by proportioning: 1.5 moles of 1 mole of bromobenzenes, Mg1.05 mole, Union carbide A-162; In the glass reaction bottle of the 1000ml of having stirring, reflux, add 1.05 moles of (25.2g) magnesium chips, 200gTHF, 0.02 mole of (3.1g) bromobenzene, 0.01g iodine stirs, is heated to 60 ℃ of initiation reactions; Add 1.5 moles of Union carbide A-162s (267g), stir, be heated to about 60 ℃; 400g toluene is mixed with 0.98 mole of (153.9g) bromobenzene, in 4 hours, at the uniform velocity be added drop-wise in the reactor, keep 60-70 ℃ in the reactor, be added dropwise to complete rear 70 ℃ of left and right sides insulation reaction 1 hour; The reaction finish after, with decanting process steam crude product, rectifying obtains highly purified aminomethyl phenyl diethoxy silane again.Reaction is when finishing, and the sampling gas phase analysis removes solvent peak, and bromobenzene content is below 0.5%, aminomethyl phenyl diethoxy silane content 90%.Steam solvent THF, toluene and excessive Union carbide A-162, then decompression steams aminomethyl phenyl diethoxy silane crude product 192g, and crude product rectifying obtains aminomethyl phenyl diethoxy silicon product 157g, purity 99.6%, yield 74%.
Embodiment 2
Choose by proportioning: 1.5 moles of halobenzene 1 mole of (wherein 0.02 mole of bromobenzene, 0.98 mole of chlorobenzene), Mg1.05 mole, Union carbide A-162s; In the glass reaction bottle of the 1000ml of having stirring, reflux, add 1.05 moles of (25.2g) magnesium chips, 200gTHF, 0.02 mole of (3.1g) bromobenzene, 0.006g iodine stirs, is heated to 60 ℃ of initiation reactions; Add 1.5 moles of Union carbide A-162s (267g), stir, be heated to about 60 ℃; 400gTHF is mixed with 0.98 mole of (110.3g) chlorobenzene, in 4 hours, at the uniform velocity be added drop-wise in the reactor, keep 60-70 ℃ in the reactor, be added dropwise to complete rear 70 ℃ of left and right sides insulation reaction 1 hour; The reaction finish after, with decanting process steam crude product, rectifying obtains highly purified aminomethyl phenyl diethoxy silane again.When reaction is finished, the sampling gas phase analysis, remove solvent peak, chlorobenzene content is below 0.5%, and product aminomethyl phenyl diethoxy silane content 85% steams solvent THF, toluene and Union carbide A-162, then decompression steams aminomethyl phenyl diethoxy silane crude product 194g, crude product rectifying obtains product 147g, purity 99.6%, yield 70%.
Embodiment 3
Choose by proportioning: 2 moles of 1 mole of bromobenzenes, Mg1.05 mole, Union carbide A-162; In the glass reaction bottle of the 1000ml of having stirring, reflux, add 1.05 moles of (25.2g) magnesium chips, 500gTHF, 0.02 mole of (3.1g) bromobenzene, 0.008g iodine stirs, is heated to 60 ℃ of initiation reactions; Add 2 moles of Union carbide A-162s (356.6g), stir, be heated to about 60 ℃; 100gTHF is mixed with 0.98 mole of (153.9g) bromobenzene, in 4 hours, at the uniform velocity be added drop-wise in the reactor, keep 60-65 ℃ in the reactor, be added dropwise to complete rear 65 ℃ of left and right sides insulation reaction 1 hour; The reaction finish after, with decanting process steam crude product, rectifying obtains highly purified aminomethyl phenyl diethoxy silane again.Sampling gas phase analysis when reaction is finished, remove solvent peak, bromobenzene content is below 0.5%, aminomethyl phenyl diethoxy silane content 91%, steam solvent THF, Union carbide A-162, then decompression steams aminomethyl phenyl diethoxy silane crude product 198g, and crude product rectifying obtains product 160g, purity 99.6%, yield 76%.
Embodiment 4
Choose by proportioning: 2 moles of 1 mole of bromobenzenes, Mg1.05 mole, methyltrimethoxy silane; In the glass reaction bottle of the 1000ml of having stirring, reflux, add 1.05 moles of (25.2g) magnesium chips, 500gTHF, 0.02 mole of (3.1g) bromobenzene, 0.012g iodine stirs, is heated to 60 ℃ of initiation reactions; Add 2.00 moles of methyltrimethoxy silanes (272g), stir, be heated to about 60 ℃; 100gTHF is mixed with 0.98 mole of (153.9g) bromobenzene, in 4 hours, at the uniform velocity be added drop-wise in the reactor, keep 60-65 ℃ in the reactor, be added dropwise to complete rear 65 ℃ of left and right sides insulation reaction 1 hour; The reaction finish after, with decanting process steam crude product, rectifying obtains highly purified aminomethyl phenyl diethoxy silane again.Sampling gas phase analysis when reaction is finished, remove solvent peak, bromobenzene content is below 0.5%, aminomethyl phenyl dimethoxy silane contents 85%, steam solvent THF, Union carbide A-162, then decompression steams aminomethyl phenyl dimethoxy silane crude product 168g, and crude product rectifying obtains product 118g, purity 99.6%, yield 65%.
Use the present invention to prepare the aminomethyl phenyl dialkoxy silicane, Ge Shi, one step of substitution reaction finish, in the reaction process, the phenyl-magnesium-halide Grignard reagent and the silane that generate carry out substitution reaction, halobenzene and Grignard reagent coupled reaction have been avoided, reduced side reaction, product purity is high, improved reaction yield.In the product leaching process, adopt decanting process, avoided numerous and diverse aftertreatment technologys such as filtration, product yield is high, technique is simple, environmental protection and energy saving.
Whipping appts among the present invention on the reactor can to the material stirring that adds, evenly mix interior each reactant of reactor; It is back flow reaction that reflux on the reactor makes whole reaction, has reduced the steam of reactant and solvent and has overflowed, and is conducive to save cost.
Claims (9)
1. the preparation method of an aminomethyl phenyl dialkoxy silicane is characterized in that comprising the steps:
A, press reaction mass mole proportioning, halobenzene: Mg:MeSi(Y)
3=1:1-1.5:1-5 chooses reaction mass;
B, to stir, in the reactor of reflux, doubly solvent of the halobenzene, Mg quality 6-20 that adds whole Mg, 2%-3%, the iodine of Mg quality 0.01%-0.05% stir, are heated to 30-110 ℃ of initiation reactions;
C, in reactor, add MeSi(Y)
3, stir, be heated to 30-110 ℃;
D, with remaining halobenzene and Mg quality 3-16 solvent doubly, be added drop-wise in the reactor, keep 30-110 ℃ in the reactor, dripped then under 30-100 ℃ of temperature insulation reaction 1-5 hour in about 3-10 hour;
E, fully after the reaction, with decanting process steam crude product, rectifying obtains highly purified aminomethyl phenyl dialkoxy silicane again;
Wherein Me is CH
3, Y is OCH3 or OC2H5.
2. the preparation method of aminomethyl phenyl dialkoxy silicane according to claim 1 is characterized in that described halobenzene, Mg, MeSi(Y) a mole proportioning is halobenzene: Mg:MeSi(Y)=1:1.1:1.5.
3. the preparation method of aminomethyl phenyl dialkoxy silicane according to claim 1 and 2 is characterized in that in described b, c, the step, behind the adding reactant, is heated to 50-70 ℃.
4. the preparation method of aminomethyl phenyl dialkoxy silicane according to claim 1 and 2 is characterized in that remaining on 50-70 ℃ in the reactor in the described d step.
5. the preparation method of aminomethyl phenyl dialkoxy silicane according to claim 1 is characterized in that described halobenzene is a kind of in chlorobenzene, bromobenzene, the iodobenzene.
6. the preparation method of aminomethyl phenyl dialkoxy silicane according to claim 1 or 5 is characterized in that described halobenzene is bromobenzene.
7. the preparation method of aminomethyl phenyl dialkoxy silicane according to claim 1 is characterized in that described solvent is one or more in the organic solvents such as the ethers such as tetrahydrofuran (THF), methyltetrahydrofuran, ether, toluene, benzene.
8. according to claim 1 or the preparation method of 7 described aminomethyl phenyl dialkoxy silicanes, it is characterized in that described solvent is tetrahydrofuran (THF).
9. the preparation method of aminomethyl phenyl dialkoxy silicane according to claim 1 and 2 is characterized in that described MeSi(Y)
3In, Me is CH
3, Y is OCH3 or OC2H5.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103113400A (en) * | 2013-03-12 | 2013-05-22 | 天津楷美肽生物科技有限公司 | Method for synthesizing phenyl methyl dialkoxyl silane with high selectivity |
| CN103524403A (en) * | 2013-09-30 | 2014-01-22 | 江苏礼华生物技术有限公司 | Preparation method of doxylamine succinate |
| CN104017017A (en) * | 2014-06-25 | 2014-09-03 | 四川科立鑫新材料有限公司 | Method for synthesizing phenyl-containing organosilicon monomers |
| CN104230977A (en) * | 2014-06-16 | 2014-12-24 | 杭州师范大学 | Ethyl phenyl dimethoxysilane and preparation method thereof |
| CN105732692A (en) * | 2016-03-30 | 2016-07-06 | 湖北省化学工业研究设计院 | Synthetic method of methyl phenyl dimethoxysilane |
| CN110964051A (en) * | 2019-12-04 | 2020-04-07 | 湖北华邦化学有限公司 | Method for industrially producing dialkyl dialkoxy silane |
| CN114605887A (en) * | 2022-04-19 | 2022-06-10 | 宁波宣威彩色世界涂料有限公司 | Smooth, clean and odor-free super-scrubbing water paint for skin |
| CN115448944A (en) * | 2022-08-09 | 2022-12-09 | 湖北兴瑞硅材料有限公司 | Synthesis method of methyl phenyl dimethoxy silane |
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Cited By (13)
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| CN103113400B (en) * | 2013-03-12 | 2016-04-27 | 天津楷美肽生物科技有限公司 | The method of synthesis of phenyl methyl dioxane TMOS |
| CN103113400A (en) * | 2013-03-12 | 2013-05-22 | 天津楷美肽生物科技有限公司 | Method for synthesizing phenyl methyl dialkoxyl silane with high selectivity |
| CN103524403A (en) * | 2013-09-30 | 2014-01-22 | 江苏礼华生物技术有限公司 | Preparation method of doxylamine succinate |
| CN103524403B (en) * | 2013-09-30 | 2016-05-04 | 江苏礼华生物技术有限公司 | A kind of preparation method of doxylamine succinate |
| CN104230977B (en) * | 2014-06-16 | 2016-09-07 | 杭州师范大学 | A kind of ethylphenyl dimethoxysilane and preparation method thereof |
| CN104230977A (en) * | 2014-06-16 | 2014-12-24 | 杭州师范大学 | Ethyl phenyl dimethoxysilane and preparation method thereof |
| CN104017017A (en) * | 2014-06-25 | 2014-09-03 | 四川科立鑫新材料有限公司 | Method for synthesizing phenyl-containing organosilicon monomers |
| CN105732692A (en) * | 2016-03-30 | 2016-07-06 | 湖北省化学工业研究设计院 | Synthetic method of methyl phenyl dimethoxysilane |
| CN105732692B (en) * | 2016-03-30 | 2018-09-18 | 湖北省化学工业研究设计院 | The synthetic method of aminomethyl phenyl dimethoxysilane |
| CN110964051A (en) * | 2019-12-04 | 2020-04-07 | 湖北华邦化学有限公司 | Method for industrially producing dialkyl dialkoxy silane |
| CN110964051B (en) * | 2019-12-04 | 2023-03-14 | 湖北华邦化学有限公司 | Method for industrially producing dialkyl dialkoxy silane |
| CN114605887A (en) * | 2022-04-19 | 2022-06-10 | 宁波宣威彩色世界涂料有限公司 | Smooth, clean and odor-free super-scrubbing water paint for skin |
| CN115448944A (en) * | 2022-08-09 | 2022-12-09 | 湖北兴瑞硅材料有限公司 | Synthesis method of methyl phenyl dimethoxy silane |
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